<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <version>1.0</version>
  <creation_date>2016-05-22 04:27:14 UTC</creation_date>
  <update_date>2026-08-17 23:40:49 UTC</update_date>
  <accession/>
  <common_name>cAMP</common_name>
  <class>SmallMolecule</class>
  <description>cAMP is an organic compound with the formula C10H12N5O6P and an average molecular weight of 329.21 g/mol. cAMP belongs to the cyclic purine nucleotides, a subclass of purine nucleotides within the organic compounds. This compound is categorized under the superclass of nucleosides, nucleotides, and analogues.

In industrial applications, cAMP is utilized as a softener and conditioner. It has been identified in 12 recorded sources. Within the category of electrical and electronic equipment, it is found in amplifiers, antennas, communication cables or conductors, discharge lamps, and conductors or conductive bodies characterised by the conductive materials, among two other sources. It is also associated with food, food processing and cookware, specifically in food preservation, the preparation of vinegar, the preparation of wine or sparkling wine, and fermentation processes for beer. Additionally, it is found in household cleaning and consumer products, specifically in tobacco smoke filters.

cAMP interacts with six recorded protein targets. These include the cAMP-dependent protein kinase type I-alpha regulatory subunit (PRKAR1A), the cAMP-dependent protein kinase type II-beta regulatory subunit (PRKAR2B), the potassium/sodium hyperpolarization-activated cyclic nucleotide-gated channel 2 (HCN2), and the DNA-binding transcriptional dual regulator CRP (crp), as well as two other proteins.</description>
  <categories/>
  <types/>
  <synonyms>
    <synonym>3' 5'-cyclic AMP</synonym>
    <synonym>Cyclic AMP</synonym>
    <synonym>cyclic-AMP</synonym>
  </synonyms>
  <chemical_formula>C10H12N5O6P</chemical_formula>
  <average_molecular_weight>329.2059</average_molecular_weight>
  <monisotopic_moleculate_weight>329.052519653</monisotopic_moleculate_weight>
  <iupac_name>(4aR,6R,7R,7aS)-6-(6-amino-9H-purin-9-yl)-2,7-dihydroxy-hexahydro-2lambda5-furo[3,2-d][1,3,2]dioxaphosphinin-2-one</iupac_name>
  <traditional_iupac>(4aR,6R,7R,7aS)-6-(6-aminopurin-9-yl)-2,7-dihydroxy-tetrahydro-4H-2lambda5-furo[3,2-d][1,3,2]dioxaphosphinin-2-one</traditional_iupac>
  <cas_registry_number>60-92-4</cas_registry_number>
  <smiles>NC1=NC=NC2=C1N=CN2[C@@H]1O[C@@H]2COP(O)(=O)O[C@H]2[C@H]1O</smiles>
  <inchi>InChI=1S/C10H12N5O6P/c11-8-5-9(13-2-12-8)15(3-14-5)10-6(16)7-4(20-10)1-19-22(17,18)21-7/h2-4,6-7,10,16H,1H2,(H,17,18)(H2,11,12,13)/t4-,6-,7-,10-/m1/s1</inchi>
  <inchikey>IVOMOUWHDPKRLL-KQYNXXCUSA-N</inchikey>
  <taxonomy>
    <kingdom>Organic compounds</kingdom>
    <super_class>Nucleosides, nucleotides, and analogues</super_class>
    <class>Purine nucleotides</class>
    <sub_class>Cyclic purine nucleotides</sub_class>
    <direct_parent>3',5'-cyclic purine nucleotides</direct_parent>
    <alternate_parents>
      <alternative_parent>6-aminopurines</alternative_parent>
      <alternative_parent>Aminopyrimidines and derivatives</alternative_parent>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Glycosylamines</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Imidolactams</alternative_parent>
      <alternative_parent>Monosaccharide phosphates</alternative_parent>
      <alternative_parent>N-substituted imidazoles</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organic phosphoric acids and derivatives</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Pentose phosphates</alternative_parent>
      <alternative_parent>Primary amines</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Tetrahydrofurans</alternative_parent>
    </alternate_parents>
    <substituents>
      <substituent>3',5'-cyclic purine ribonucleotide</substituent>
      <substituent>6-aminopurine</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Amine</substituent>
      <substituent>Aminopyrimidine</substituent>
      <substituent>Aromatic heteropolycyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Azole</substituent>
      <substituent>Glycosyl compound</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Imidazole</substituent>
      <substituent>Imidazopyrimidine</substituent>
      <substituent>Imidolactam</substituent>
      <substituent>Monosaccharide</substituent>
      <substituent>Monosaccharide phosphate</substituent>
      <substituent>N-glycosyl compound</substituent>
      <substituent>N-substituted imidazole</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organic phosphoric acid derivative</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Pentose phosphate</substituent>
      <substituent>Primary amine</substituent>
      <substituent>Purine</substituent>
      <substituent>Pyrimidine</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Tetrahydrofuran</substituent>
    </substituents>
    <molecular_framework>Aromatic heteropolycyclic compounds</molecular_framework>
    <descriptors>
      <descriptor>3',5'-Cyclic nuclcleotides</descriptor>
      <descriptor>3',5'-cyclic purine nucleotide</descriptor>
      <descriptor>adenyl ribonucleotide</descriptor>
    </descriptors>
  </taxonomy>
  <status>Detected and Not Quantified</status>
  <origin/>
  <cellular_locations/>
  <biofluid_locations/>
  <tissue_locations/>
  <pathways>
    <pathway>
      <name>Purine Metabolism</name>
      <smpdb_id>SMP0000050</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Adenosine Deaminase Deficiency</name>
      <smpdb_id>SMP0000144</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Adenylosuccinate Lyase Deficiency</name>
      <smpdb_id>SMP0000167</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Gout or Kelley-Seegmiller Syndrome</name>
      <smpdb_id>SMP0000365</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Lesch-Nyhan Syndrome (LNS)</name>
      <smpdb_id>SMP0000364</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Molybdenum Cofactor Deficiency</name>
      <smpdb_id>SMP0000203</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Xanthine Dehydrogenase Deficiency (Xanthinuria)</name>
      <smpdb_id>SMP0000220</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Purine Nucleoside Phosphorylase Deficiency</name>
      <smpdb_id>SMP0000210</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>AICA-Ribosiduria</name>
      <smpdb_id>SMP0000168</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Azathioprine Action Pathway</name>
      <smpdb_id>SMP0000427</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Mercaptopurine Action Pathway</name>
      <smpdb_id>SMP0000428</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cilostazol Action Pathway</name>
      <smpdb_id>SMP0000263</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Thioguanine Action Pathway (old)</name>
      <smpdb_id>SMP0000430</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Dopamine Activation of Neurological Reward System</name>
      <smpdb_id>SMP0000308</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Excitatory Neural Signalling Through 5-HTR 4 and Serotonin</name>
      <smpdb_id>SMP0000309</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Corticotropin Activation of Cortisol Production</name>
      <smpdb_id>SMP0000310</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Excitatory Neural Signalling Through 5-HTR 7 and Serotonin</name>
      <smpdb_id>SMP0000311</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Excitatory Neural Signalling Through 5-HTR 6 and Serotonin</name>
      <smpdb_id>SMP0000312</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Intracellular Signalling Through Adenosine Receptor A2a and Adenosine</name>
      <smpdb_id>SMP0000320</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Intracellular Signalling Through Adenosine Receptor A2b and Adenosine</name>
      <smpdb_id>SMP0000321</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Vasopressin Regulation of Water Homeostasis</name>
      <smpdb_id>SMP0000322</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Intracellular Signalling Through FSH Receptor and Follicle Stimulating Hormone</name>
      <smpdb_id>SMP0000333</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Intracellular Signalling Through Histamine H2 Receptor and Histamine</name>
      <smpdb_id>SMP0000335</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Intracellular Signalling Through LHCGR Receptor and Luteinizing Hormone/Choriogonadotropin</name>
      <smpdb_id>SMP0000338</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Intracellular Signalling Through PGD2 receptor and Prostaglandin D2</name>
      <smpdb_id>SMP0000343</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Intracellular Signalling Through Prostacyclin Receptor and Prostacyclin</name>
      <smpdb_id>SMP0000354</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Xanthinuria Type I</name>
      <smpdb_id>SMP0000512</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Xanthinuria Type II</name>
      <smpdb_id>SMP0000513</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Adenine Phosphoribosyltransferase Deficiency (APRT)</name>
      <smpdb_id>SMP0000535</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Mitochondrial DNA Depletion Syndrome-3</name>
      <smpdb_id>SMP0000536</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Myoadenylate Deaminase Deficiency</name>
      <smpdb_id>SMP0000537</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Amiodarone Action Pathway</name>
      <smpdb_id>SMP0000665</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Lysophosphatidic Acid LPA1 Signalling</name>
      <smpdb_id>SMP0063746</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Lysophosphatidic Acid LPA2 Signalling</name>
      <smpdb_id>SMP0063753</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Lysophosphatidic Acid LPA3 Signalling</name>
      <smpdb_id>SMP0063755</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Lysophosphatidic Acid LPA4 Signalling</name>
      <smpdb_id>SMP0063756</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Lysophosphatidic Acid LPA5 Signalling</name>
      <smpdb_id>SMP0063757</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Lysophosphatidic Acid LPA6 Signalling</name>
      <smpdb_id>SMP0063759</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Activation of cAMP-dependent protein kinase, PKA</name>
      <smpdb_id>SMP0063764</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Ion Channels and Their Functional Role in Vascular Endothelium</name>
      <smpdb_id>SMP0063778</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>GnRH Signaling Pathway</name>
      <smpdb_id>SMP0063811</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Pancreas Function - Beta Cell</name>
      <smpdb_id>SMP0121018</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cangrelor Action Pathway</name>
      <smpdb_id>SMP0121141</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Amiodarone Action Pathway (New)</name>
      <smpdb_id>SMP0122646</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cilostazol Action Pathway (new)</name>
      <smpdb_id>SMP0122708</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Ranitidine H2 Anti-Histamine Action Pathway</name>
      <smpdb_id>SMP0122729</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Dipyridamole Action Pathway</name>
      <smpdb_id>SMP0122804</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Codeine Opioid Action Pathway</name>
      <smpdb_id>SMP0122959</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Diphenoxylate Opioid Agonist Action Pathway</name>
      <smpdb_id>SMP0123027</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cimetidine H2 Anti-Histamine Action Pathway</name>
      <smpdb_id>SMP0123152</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Metiamide H2 Anti-Histamine Action Pathway</name>
      <smpdb_id>SMP0123167</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Roxatidine Acetate H2 Anti-Histamine Action Pathway</name>
      <smpdb_id>SMP0123168</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Epinephrine B2-Adrenergic Bronchodilation Action Pathway</name>
      <smpdb_id>SMP0124452</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Diazepam Action Pathway</name>
      <smpdb_id>SMP0124471</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Timolol Action Pathway (New)</name>
      <smpdb_id>SMP0124552</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Atropine M2 Cardiac Muscle Contraction Action Pathway</name>
      <smpdb_id>SMP0124615</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Methadone Opioid Agonist Action Pathway</name>
      <smpdb_id>SMP0124670</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Levodopa Pahway</name>
      <smpdb_id>SMP0124684</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Misoprostol Action Pathway</name>
      <smpdb_id>SMP0124718</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Sitagliptin Action Pathway</name>
      <smpdb_id>SMP0124724</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Desmopressin Action Pathway</name>
      <smpdb_id>SMP0124889</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Alfentanil Opioid Agonist Action Pathway</name>
      <smpdb_id>SMP0124996</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Dihydrocodeine Opioid Agonist Action Pathway</name>
      <smpdb_id>SMP0124998</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Dihydromorphine Opioid Agonist Action Pathway</name>
      <smpdb_id>SMP0124999</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Carfentanil Opioid Agonist Action Pathway</name>
      <smpdb_id>SMP0125010</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>3-Methylthiofentanyl Opioid Agonist Action Pathway</name>
      <smpdb_id>SMP0125012</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Dezocine Kappa Opioid Antagonism Action Pathway</name>
      <smpdb_id>SMP0125013</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Ethylmorphine Opioid Action Pathway</name>
      <smpdb_id>SMP0125015</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Hydrocodone Opioid Agonist Action Pathway</name>
      <smpdb_id>SMP0125016</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Hydromorphone Opioid Agonist Action Pathway</name>
      <smpdb_id>SMP0125017</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Morphine Opioid Agonist Action Pathway</name>
      <smpdb_id>SMP0125018</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Sufentanil Opioid Agonist Action Pathway</name>
      <smpdb_id>SMP0125019</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Oxymorphone Opioid Agonist Action Pathway</name>
      <smpdb_id>SMP0125021</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Remifentanil Opioid Anasthetic Action Pathway</name>
      <smpdb_id>SMP0125022</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Oxycodone Opioid Agonist Action Pathway</name>
      <smpdb_id>SMP0125024</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Tramadol Opioid Agonist Action Pathway</name>
      <smpdb_id>SMP0125025</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Levorphanol Opioid Agonist Action Pathway</name>
      <smpdb_id>SMP0125026</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Lorazepam Action Pathway</name>
      <smpdb_id>SMP0125053</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Clonazepam Action Pathway</name>
      <smpdb_id>SMP0125054</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Midazolam Action Pathway</name>
      <smpdb_id>SMP0125055</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Alprazolam Action Pathway</name>
      <smpdb_id>SMP0125056</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Etizolam Action Pathway</name>
      <smpdb_id>SMP0125057</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Temazepam Action Pathway</name>
      <smpdb_id>SMP0125058</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Bromazepam Action Pathway</name>
      <smpdb_id>SMP0125070</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Thiocolchicoside Action Pathway (New)</name>
      <smpdb_id>SMP0125071</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Zolpidem Action Pathway (New)</name>
      <smpdb_id>SMP0125072</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Gamma-Aminobutyric Acid Biosynthesis</name>
      <smpdb_id>SMP0125090</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Clotrimazole Action Pathway</name>
      <smpdb_id>SMP0125104</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Tizanidine</name>
      <smpdb_id>SMP0125127</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Ethanol GABA Agonist Action Pathway</name>
      <smpdb_id>SMP0125151</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Diamorphine Action Pathway</name>
      <smpdb_id>SMP0125174</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Loperamide Action Pathway</name>
      <smpdb_id>SMP0125189</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Meperidine opioid agonist Action Pathway</name>
      <smpdb_id>SMP0125199</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Fentanyl Opioid Agonist Action Pathway</name>
      <smpdb_id>SMP0125203</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Methylphenidate Dopamine Reuptake Inhibitor Action Pathway</name>
      <smpdb_id>SMP0125204</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Drotaverine Action Pathway</name>
      <smpdb_id>SMP0125240</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Bupropion Action Pathway</name>
      <smpdb_id>SMP0125268</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Naltrexone Opioid Antagonist Action Pathway</name>
      <smpdb_id>SMP0125274</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Levonorgestrel Action Pathway</name>
      <smpdb_id>SMP0125332</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Levallorphan Action Pathway (New)</name>
      <smpdb_id>SMP0125336</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Adenosine Deaminase Deficiency</name>
      <smpdb_id>SMP0125721</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Adenylosuccinate Lyase Deficiency</name>
      <smpdb_id>SMP0125722</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Gout or Kelley-Seegmiller Syndrome</name>
      <smpdb_id>SMP0125723</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Molybdenum Cofactor Deficiency</name>
      <smpdb_id>SMP0125725</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Xanthinuria Type I</name>
      <smpdb_id>SMP0125727</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Purine Nucleoside Phosphorylase Deficiency</name>
      <smpdb_id>SMP0125728</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Xanthinuria Type II</name>
      <smpdb_id>SMP0125731</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Adenine Phosphoribosyltransferase Deficiency (APRT)</name>
      <smpdb_id>SMP0125732</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Mitochondrial DNA Depletion Syndrome-3</name>
      <smpdb_id>SMP0125734</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Myoadenylate Deaminase Deficiency</name>
      <smpdb_id>SMP0125735</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Ritodrine B2-Adrenergic Myometrial Smooth Muscle Relaxation Action Pathway</name>
      <smpdb_id>SMP0126043</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Orciprenaline Action Pathway</name>
      <smpdb_id>SMP0126083</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Salmeterol Action Pathway</name>
      <smpdb_id>SMP0126085</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Formoterol Action Pathway</name>
      <smpdb_id>SMP0126086</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Arformoterol Action Pathway</name>
      <smpdb_id>SMP0126088</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Indacaterol Action Pathway</name>
      <smpdb_id>SMP0126090</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Olodaterol Action Pathway</name>
      <smpdb_id>SMP0126091</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Levosalbutamol Action Pathway</name>
      <smpdb_id>SMP0126092</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Terbutaline Action Pathway</name>
      <smpdb_id>SMP0126093</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Procaterol Action Pathway</name>
      <smpdb_id>SMP0126094</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Celiprolol B2-Adrenergic Vasodilation Action Pathway</name>
      <smpdb_id>SMP0126095</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Clenbuterol Action Pathway</name>
      <smpdb_id>SMP0126097</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Dipivefrin A2-Adrenergic Vasocontriction Action Pathway</name>
      <smpdb_id>SMP0126098</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Fenoterol Action Pathway</name>
      <smpdb_id>SMP0126100</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Isoetharine Action Pathway</name>
      <smpdb_id>SMP0126101</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Pirbuterol Action Pathway</name>
      <smpdb_id>SMP0126102</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Vilanterol Action Pathway</name>
      <smpdb_id>SMP0126103</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Mirabegron Action Pathway</name>
      <smpdb_id>SMP0126105</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Racepinephrine B2-Adrenergic Bronchodilation Action Pathway</name>
      <smpdb_id>SMP0126107</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Vibegron Action Pathway</name>
      <smpdb_id>SMP0126109</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Ephedrine B2-Adrenergic Bronchodilation Action Pathway</name>
      <smpdb_id>SMP0126111</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Etafedrine Action Pathway</name>
      <smpdb_id>SMP0126114</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Triazolam Action Pathway</name>
      <smpdb_id>SMP0126116</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Butabarbital Action Pathway</name>
      <smpdb_id>SMP0126119</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Chlordiazepoxide Action Pathway</name>
      <smpdb_id>SMP0126120</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Clobazam Action Pathway</name>
      <smpdb_id>SMP0126121</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Clorazepic Acid Action Pathway</name>
      <smpdb_id>SMP0126122</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Clotiazepam Action Pathway</name>
      <smpdb_id>SMP0126124</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Estazolam Action Pathway</name>
      <smpdb_id>SMP0126125</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Etomidate Action Pathway</name>
      <smpdb_id>SMP0126127</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Flunitrazepam Action Pathway</name>
      <smpdb_id>SMP0126128</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Flurazepam Action Pathway</name>
      <smpdb_id>SMP0126129</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Glutethimide Action Pathway</name>
      <smpdb_id>SMP0126131</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Ketazolam Action Pathway</name>
      <smpdb_id>SMP0126132</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Lormetazepam Action Pathway</name>
      <smpdb_id>SMP0126133</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Meprobamate Action Pathway</name>
      <smpdb_id>SMP0126134</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Oxazepam Action Pathway</name>
      <smpdb_id>SMP0126135</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Prazepam Action Pathway</name>
      <smpdb_id>SMP0126137</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Quazepam Action Pathway</name>
      <smpdb_id>SMP0126138</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Remimazolam Action Pathway</name>
      <smpdb_id>SMP0126145</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Talbutal Action Pathway</name>
      <smpdb_id>SMP0126147</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Brexanolone Action Pathway</name>
      <smpdb_id>SMP0126148</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Butalbital Action Pathway</name>
      <smpdb_id>SMP0126149</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Eszopiclone Action Pathway</name>
      <smpdb_id>SMP0126150</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Desflurane GABA(A) Anesthetic Action Pathway</name>
      <smpdb_id>SMP0126151</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Flumazenil Action Pathway</name>
      <smpdb_id>SMP0126152</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Ganaxolone Action Pathway</name>
      <smpdb_id>SMP0126153</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Halothane GABA(A) Anesthetic Action Pathway</name>
      <smpdb_id>SMP0126161</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Isoflurane GABA(A) Anesthetic Action Pathway</name>
      <smpdb_id>SMP0126162</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Nitrazepam Action Pathway</name>
      <smpdb_id>SMP0126164</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Pentobarbital Action Pathway</name>
      <smpdb_id>SMP0126165</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Primidone Action Pathway</name>
      <smpdb_id>SMP0126166</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Stiripentol GABA(A) Antiepileptic Action Pathway</name>
      <smpdb_id>SMP0126168</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Sevoflurane GABA(A) Anesthetic Action Pathway</name>
      <smpdb_id>SMP0126170</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Carteolol B2-Adrenergic Ciliary Muscle Contraction Action Pathway</name>
      <smpdb_id>SMP0126201</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Metipranolol Action Pathway (New)</name>
      <smpdb_id>SMP0126208</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Timolol B2-Adrenergic Ciliary Muscle Contraction Action Pathway</name>
      <smpdb_id>SMP0126232</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Disopyramide Cardiac Action Pathway</name>
      <smpdb_id>SMP0126247</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Mexiletine Action Pathway (New)</name>
      <smpdb_id>SMP0126263</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Procainamide Action Pathway (New)</name>
      <smpdb_id>SMP0126265</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Ajmaline Action Pathway</name>
      <smpdb_id>SMP0126271</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Propafenone Action Pathway</name>
      <smpdb_id>SMP0126275</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Ranolazine Action Pathway</name>
      <smpdb_id>SMP0126279</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Quinidine Action Pathway (New)</name>
      <smpdb_id>SMP0126282</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Diltiazem Calcium Channel Cardiac Muscle Relaxation Action Pathway</name>
      <smpdb_id>SMP0126292</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Methylnaltrexone Opioid Antagonist Action Pathway</name>
      <smpdb_id>SMP0126308</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Nalmefene Opioid Antagonist Action Pathway</name>
      <smpdb_id>SMP0126315</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Ethosuximide Action Pathway</name>
      <smpdb_id>SMP0126318</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Butorphanol Opioid Antagonist Action Pathway</name>
      <smpdb_id>SMP0126319</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Samidorphan Action Pathway</name>
      <smpdb_id>SMP0126322</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Pentazocine Opioid Antagonist Action Pathway</name>
      <smpdb_id>SMP0126325</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Nalbuphine Opioid Antagonist Action Pathway</name>
      <smpdb_id>SMP0126326</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Naloxone Opioid Antagonist Action Pathway</name>
      <smpdb_id>SMP0126328</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Methsuximide Action Pathway</name>
      <smpdb_id>SMP0126331</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Naloxegol Action Pathway</name>
      <smpdb_id>SMP0126335</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Naldemedine Opioid Antagonist Action Pathway</name>
      <smpdb_id>SMP0126337</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Trimebutine M3 Receptor Intestine Relaxation Action Pathway</name>
      <smpdb_id>SMP0126338</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Alvimopan Opioid Antagonist Action Pathway</name>
      <smpdb_id>SMP0126339</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Trimethadione Action Pathway</name>
      <smpdb_id>SMP0126340</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Diprenorphine Action Pathway</name>
      <smpdb_id>SMP0126341</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Solriamfetol Action Pathway</name>
      <smpdb_id>SMP0126346</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Magnesium Sulfate Action Pathway</name>
      <smpdb_id>SMP0126350</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Flavoxate Action Pathway</name>
      <smpdb_id>SMP0126385</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Propiverine Action Pathway</name>
      <smpdb_id>SMP0126388</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Amifampridine Action Pathway</name>
      <smpdb_id>SMP0126393</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Dalfampridine Action Pathway</name>
      <smpdb_id>SMP0126397</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Hyoscyamine M2 Smooth Muscle Relaxation Action Pathway</name>
      <smpdb_id>SMP0126402</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Anisotropine Methylbromide M2 GI Tract Relaxation Action Pathway</name>
      <smpdb_id>SMP0126403</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Verapamil Calcium Channel Cardiac Muscle Relaxation Action Pathway</name>
      <smpdb_id>SMP0126428</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Duloxetine SNRI - Dopamine Norepinephrine Inhibition Action Pathway</name>
      <smpdb_id>SMP0126450</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Pramipexole Mechanism of Action Action Pathway</name>
      <smpdb_id>SMP0126459</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Clopidogrel Action Pathway (new)</name>
      <smpdb_id>SMP0126460</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Prasugrel Action Pathway</name>
      <smpdb_id>SMP0126463</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Ticagrelor Action Pathway</name>
      <smpdb_id>SMP0126465</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Ticlopidine Action Pathway (new)</name>
      <smpdb_id>SMP0126467</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Dipyridamole Phosphodiesterase Action Pathway</name>
      <smpdb_id>SMP0126489</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Epoprostenol Action Pathway</name>
      <smpdb_id>SMP0126492</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Droxidopa B2-Adrenergic Artery Dilation Action Pathway</name>
      <smpdb_id>SMP0126493</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Ephedrine B2-Adrenergic Vasodilation Action Pathway</name>
      <smpdb_id>SMP0126499</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Amoxapine SSRI Action Pathway</name>
      <smpdb_id>SMP0126502</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Lidocaine Sodium Channel Cardiac Muscle Relaxation Action Pathway</name>
      <smpdb_id>SMP0126504</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Iloprost Action Pathway</name>
      <smpdb_id>SMP0126507</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Selexipag Action Pathway</name>
      <smpdb_id>SMP0126508</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Treprostinil Action Pathway</name>
      <smpdb_id>SMP0126517</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Tocainide Sodium Channel Cardiac Muscle Relaxation Action Pathway</name>
      <smpdb_id>SMP0126519</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Norgestrel Action Pathway</name>
      <smpdb_id>SMP0126522</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Etonogestrel Action Pathway</name>
      <smpdb_id>SMP0126525</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Megestrol acetate Action Pathway</name>
      <smpdb_id>SMP0126528</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Progesterone Action Pathway</name>
      <smpdb_id>SMP0126529</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Norethisterone Action Pathway</name>
      <smpdb_id>SMP0126536</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Caffeine Adrenergic A1 vasoconstriction Action Pathway</name>
      <smpdb_id>SMP0126537</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Drospirenone Action Pathway</name>
      <smpdb_id>SMP0126538</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Norelgestromin Action Pathway</name>
      <smpdb_id>SMP0126539</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Dienogest Action Pathway</name>
      <smpdb_id>SMP0126541</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Segesterone acetate Action Pathway</name>
      <smpdb_id>SMP0126542</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cocaine Dopamine-reuptake Inhibitor Action Pathway</name>
      <smpdb_id>SMP0126543</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Triflusal Action Pathway (new)</name>
      <smpdb_id>SMP0126547</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Triflusal Action Pathway</name>
      <smpdb_id>SMP0126548</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Dipivefrin B2-Adrenergic Ciliary Muscle Relaxation Action Pathway</name>
      <smpdb_id>SMP0126568</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Methylphenidate Norepinephrine Reuptake Inhibitor Action Pathway</name>
      <smpdb_id>SMP0126572</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Norepinephrine B2-Adrenergic Artery Dilation Action Pathway</name>
      <smpdb_id>SMP0126573</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Salbutamol Action Pathway</name>
      <smpdb_id>SMP0126574</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Nylidrin Action Pathway</name>
      <smpdb_id>SMP0126575</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Oxprenolol B2-Adrenergic Vasoconstriction Action Pathway</name>
      <smpdb_id>SMP0126584</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Domperidone Mechanism of Action Action Pathway</name>
      <smpdb_id>SMP0126605</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Dezocine Mu Opioid Agonism Action Pathway</name>
      <smpdb_id>SMP0126631</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Apomorphine Mechanism of Action Action Pathway</name>
      <smpdb_id>SMP0126633</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Pergolide Mechanism of Action Action Pathway</name>
      <smpdb_id>SMP0126635</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Fenoldopam Mechanism of Action Action Pathway</name>
      <smpdb_id>SMP0126645</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Carteolol B1-Adrenergic Ciliary Muscle Contraction Action Pathway</name>
      <smpdb_id>SMP0126647</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Nadolol B2-Adrenergic Vasoconstriction Action Pathway</name>
      <smpdb_id>SMP0126648</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Propranolol B2-Adrenergic Vasoconstriction Action Pathway</name>
      <smpdb_id>SMP0126650</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Pindolol B2-Adrenergic Vasodilation Action Pathway</name>
      <smpdb_id>SMP0126653</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Epicriptine Mechanism of Action Action Pathway</name>
      <smpdb_id>SMP0126655</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Ergoloid mesylate Mechanism of Action Action Pathway</name>
      <smpdb_id>SMP0126658</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Dihydroergocryptine Mechanism of Action Action Pathway</name>
      <smpdb_id>SMP0126659</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cabergoline Mechanism of Action Action Pathway</name>
      <smpdb_id>SMP0126670</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Quinagolide Mechanism of Action Action Pathway</name>
      <smpdb_id>SMP0126673</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Bromocriptine Mechanism of Action Action Pathway</name>
      <smpdb_id>SMP0126674</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Paramethadione Action Pathway</name>
      <smpdb_id>SMP0126675</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Pilocarpine M2 Ciliary Muscle Contraction Action Pathway</name>
      <smpdb_id>SMP0126679</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Methacholine M2 Bronchoconstriction Action Pathway</name>
      <smpdb_id>SMP0126683</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Safinamide Action Pathway</name>
      <smpdb_id>SMP0126696</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Rasagiline Action Pathway</name>
      <smpdb_id>SMP0126709</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Selegiline Action Pathway</name>
      <smpdb_id>SMP0126719</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Alverine Serotonin Antagonist Action Pathway</name>
      <smpdb_id>SMP0126727</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Asenapine Dopamine Antagonist Action Pathway</name>
      <smpdb_id>SMP0126736</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Difelikefalin Opioid Agonist Action Pathway</name>
      <smpdb_id>SMP0126764</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Nizatidine H2 Anti-Histamine Action Pathway</name>
      <smpdb_id>SMP0126776</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Famotidine H2 Anti-Histamine Action Pathway</name>
      <smpdb_id>SMP0126789</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Lavoltidine H2 Anti-histamine Action Pathway</name>
      <smpdb_id>SMP0126790</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Morphine Opioid Agonist Brain Action Pathway</name>
      <smpdb_id>SMP0126791</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Methadyl acetate Opioid Agonist Action Pathway</name>
      <smpdb_id>SMP0126792</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Ketobemidone Opioid Agonist Action Pathway</name>
      <smpdb_id>SMP0126793</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Anileridineb Opioid Agonist Action Pathway</name>
      <smpdb_id>SMP0126794</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Etorphine Opioid Agonist Action Pathway</name>
      <smpdb_id>SMP0126797</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Lofentanil Opioid Agonist Action Pathway</name>
      <smpdb_id>SMP0126798</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Bezitramide Opioid Agonist Action Pathway</name>
      <smpdb_id>SMP0126801</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Tapentadol Opioid Agonist Action Pathway</name>
      <smpdb_id>SMP0126806</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Desomorphine Opioid Agonist Action Pathway</name>
      <smpdb_id>SMP0126807</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Secobarbital Action Pathway</name>
      <smpdb_id>SMP0126809</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Thiopental Action Pathway</name>
      <smpdb_id>SMP0126813</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Dextropropoxyphene Opioid Agonist Action Pathway</name>
      <smpdb_id>SMP0126814</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Dextromoramide Opioid Agonist Action Pathway</name>
      <smpdb_id>SMP0126815</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Piritramide Opioid Agonist Action Pathway</name>
      <smpdb_id>SMP0126816</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Methylphenobarbital Action Pathway</name>
      <smpdb_id>SMP0126819</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Dihydroetorphine Opioid Agonist Action Pathway</name>
      <smpdb_id>SMP0126823</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Oliceridine Opioid Agonist Action Pathway</name>
      <smpdb_id>SMP0126824</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Benzhydrocodone Opioid Agonist Action Pathway</name>
      <smpdb_id>SMP0126825</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Levacetylmethadol Opioid Agonist Action Pathway</name>
      <smpdb_id>SMP0126826</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Remifentanil Opioid Analgesic Action Pathway</name>
      <smpdb_id>SMP0126828</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Normethadone Action Pathway</name>
      <smpdb_id>SMP0126829</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Zaleplon Action Pathway</name>
      <smpdb_id>SMP0126830</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phenobarbital Action Pathway</name>
      <smpdb_id>SMP0126831</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Zopiclone Action Pathway</name>
      <smpdb_id>SMP0126832</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Quinidine barbiturate Action Pathway</name>
      <smpdb_id>SMP0126833</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Amobarbital Action Pathway</name>
      <smpdb_id>SMP0126834</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Butobarbital Action Pathway</name>
      <smpdb_id>SMP0126835</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Fospropofol Action Pathway</name>
      <smpdb_id>SMP0126836</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Trimebutine Opioid Action Pathway</name>
      <smpdb_id>SMP0126837</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Eluxadoline Action Pathway</name>
      <smpdb_id>SMP0126838</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Gi Adrenergic Smooth Muscle Contraction</name>
      <smpdb_id>SMP0126894</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Gs Adrenergic Smooth Muscle Relaxation</name>
      <smpdb_id>SMP0126934</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Moricizine Action Pathway</name>
      <smpdb_id>SMP0126950</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Gi Muscarinic Cardiac Muscle Contraction</name>
      <smpdb_id>SMP0126951</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Neuronal Dopamine Gs Cascade</name>
      <smpdb_id>SMP0126952</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Gs Histaminic Smooth Muscle Relaxation</name>
      <smpdb_id>SMP0126967</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Muscular Gi Protein Cascade</name>
      <smpdb_id>SMP0126972</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Muscular Gs Protein Cascade</name>
      <smpdb_id>SMP0126976</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Sumatriptan Mechanism of Action Action Pathway</name>
      <smpdb_id>SMP0126984</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Benzatropine Dopamine Reuptake Inhibitor Action Pathway</name>
      <smpdb_id>SMP0126985</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Gi Serotonergic Smooth Muscle Relaxation</name>
      <smpdb_id>SMP0126986</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Mazindol Dopamine Reuptake Inhibitor Action Pathway</name>
      <smpdb_id>SMP0126988</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Benzphetamine Dopamine Reuptake Inhibitor Action Pathway</name>
      <smpdb_id>SMP0126989</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Lisdexamfetamine Dopamine Reuptake Inhibitor Action Pathway</name>
      <smpdb_id>SMP0126990</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Naratriptan Mechanism of Action Action Pathway</name>
      <smpdb_id>SMP0126991</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Gi Serotonergic Vasoconstriction</name>
      <smpdb_id>SMP0126992</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Dextroamphetamine Dopamine Reuptake Inhibitor Action Pathway</name>
      <smpdb_id>SMP0126994</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Zolmitriptan Mechanism of Action Action Pathway</name>
      <smpdb_id>SMP0126995</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Eletriptan Mechanism of Action Action Pathway</name>
      <smpdb_id>SMP0126996</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Vanoxerine Dopamine Reuptake Inhibitor Action Pathway</name>
      <smpdb_id>SMP0126997</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Rizatriptan Mechanism of Action Action Pathway</name>
      <smpdb_id>SMP0126998</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Frovatriptan Mechanism of Action Action Pathway</name>
      <smpdb_id>SMP0126999</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Ergotamine Mechanism of Action Action Pathway</name>
      <smpdb_id>SMP0127000</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Dihydroergotamine Mechanism of Action Action Pathway</name>
      <smpdb_id>SMP0127001</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Nomifensine Dopamine Reuptake Inhibitor Action Pathway</name>
      <smpdb_id>SMP0127002</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Serdexmethylphenidate Dopamine Reuptake Inhibitor Action Pathway</name>
      <smpdb_id>SMP0127003</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Dexmethylphenidate Dopamine Reuptake Inhibitor Action Pathway</name>
      <smpdb_id>SMP0127004</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Sibutramine Dopamine Reuptake Inhibitor Action Pathway</name>
      <smpdb_id>SMP0127006</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Carboprost tromethamine Action Pathway</name>
      <smpdb_id>SMP0127007</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Alprostadil Action Pathway</name>
      <smpdb_id>SMP0127008</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Bimatoprost Action Pathway</name>
      <smpdb_id>SMP0127009</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Dinoprostone Action Pathway</name>
      <smpdb_id>SMP0127013</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>GABA</name>
      <smpdb_id>SMP0127038</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Metoclopramide Serotonergic Smooth Muscle Contraction</name>
      <smpdb_id>SMP0127039</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Prucalopride Action Pathway</name>
      <smpdb_id>SMP0127044</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Gs Serotonergic Smooth Muscle Contraction</name>
      <smpdb_id>SMP0127045</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Incretins - Insulin release Pathway</name>
      <smpdb_id>SMP0127692</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Castor Oil Action Pathway</name>
      <smpdb_id>SMP0174887</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Tafluprost Action Pathway</name>
      <smpdb_id>SMP0175201</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Latanoprostene bunod Action Pathway</name>
      <smpdb_id>SMP0175202</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Travoprost Action Pathway</name>
      <smpdb_id>SMP0175203</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Latanoprost Action Pathway</name>
      <smpdb_id>SMP0175204</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Dinoprost tromethamine Action Pathway</name>
      <smpdb_id>SMP0175205</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Regulation of Lipolysis</name>
      <smpdb_id>SMP0573273</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Apelin Signaling</name>
      <smpdb_id>SMP0642520</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Calcium signaling</name>
      <smpdb_id>SMP0652462</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Chemokines binding chemokine receptors</name>
      <smpdb_id>SMP0681884</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Relaxin III Signaling Pathway</name>
      <smpdb_id>SMP0683421</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Relaxin II Signaling Pathway</name>
      <smpdb_id>SMP0683511</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Relaxin IV Signaling Pathway</name>
      <smpdb_id>SMP0688465</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Relaxin I Signaling Pathway</name>
      <smpdb_id>SMP0689895</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Olfactory Transduction OR9Q2</name>
      <smpdb_id>SMP0693491</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>ADORA2B mediated anti-inflammatory cytokine production</name>
      <smpdb_id>SMP0713406</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Surfactant Metabolism</name>
      <smpdb_id>SMP0713855</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Olfactory Transduction OR5AC2</name>
      <smpdb_id>SMP0713863</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Olfactory Transduction OR1A1</name>
      <smpdb_id>SMP0713864</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Olfactory Transduction OR2W1</name>
      <smpdb_id>SMP0713865</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Olfactory Transduction OR2AG1</name>
      <smpdb_id>SMP0713866</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Olfactory Transduction OR2J3</name>
      <smpdb_id>SMP0713867</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Olfactory Transduction OR5A1</name>
      <smpdb_id>SMP0713868</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Olfactory Transduction OR1E3</name>
      <smpdb_id>SMP0713869</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Olfactory Transduction OR1C1</name>
      <smpdb_id>SMP0713870</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Olfactory Transduction OR1L3</name>
      <smpdb_id>SMP0713871</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Glucagon signaling pathway</name>
      <smpdb_id>SMP0728339</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Ovarian Steroidogenesis</name>
      <smpdb_id>SMP0728344</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <state/>
  <appearance/>
  <experimental_properties>
    <property>
      <kind>logp</kind>
      <value>-3.4</value>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-2.29</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.96</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>solubility</kind>
      <value>3.58e+00 g/l</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-3.4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>1.83</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>3.92</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(4aR,6R,7R,7aS)-6-(6-amino-9H-purin-9-yl)-2,7-dihydroxy-hexahydro-2lambda5-furo[3,2-d][1,3,2]dioxaphosphinin-2-one</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>329.2059</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>329.052519653</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>NC1=NC=NC2=C1N=CN2[C@@H]1O[C@@H]2COP(O)(=O)O[C@H]2[C@H]1O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C10H12N5O6P</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C10H12N5O6P/c11-8-5-9(13-2-12-8)15(3-14-5)10-6(16)7-4(20-10)1-19-22(17,18)21-7/h2-4,6-7,10,16H,1H2,(H,17,18)(H2,11,12,13)/t4-,6-,7-,10-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>IVOMOUWHDPKRLL-KQYNXXCUSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>154.84</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>70.29</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>28.42</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <route_of_exposure/>
  <mechanism_of_toxicity/>
  <metabolism/>
  <toxicity/>
  <lethaldose/>
  <carcinogenicity/>
  <use_source/>
  <min_risk_level/>
  <health_effects>#&lt;HealthEffect::ActiveRecord_Associations_CollectionProxy:0x00007f3baf90d840&gt;</health_effects>
  <symptoms/>
  <treatment/>
  <drugbank_id>DB02527</drugbank_id>
  <hmdb_id/>
  <pubchem_compound_id>6076</pubchem_compound_id>
  <chembl_id/>
  <chemspider_id/>
  <kegg_id/>
  <uniprot_id/>
  <omim_id/>
  <chebi_id/>
  <biocyc_id/>
  <ctd_id/>
  <stitch_id/>
  <actor_id/>
  <pdb_id/>
  <wikipidia/>
  <general_references/>
  <targets>
    <target>
      <target_id/>
      <mechanism_of_action/>
      <constants/>
      <references/>
    </target>
    <target>
      <target_id/>
      <mechanism_of_action/>
      <constants/>
      <references/>
    </target>
    <target>
      <target_id/>
      <mechanism_of_action/>
      <constants/>
      <references/>
    </target>
    <target>
      <target_id/>
      <mechanism_of_action/>
      <constants/>
      <references/>
    </target>
    <target>
      <target_id/>
      <mechanism_of_action/>
      <constants/>
      <references/>
    </target>
    <target>
      <target_id/>
      <mechanism_of_action/>
      <constants/>
      <references/>
    </target>
    <target>
      <target_id/>
      <mechanism_of_action/>
      <constants/>
      <references/>
    </target>
    <target>
      <target_id/>
      <mechanism_of_action/>
      <constants/>
      <references/>
    </target>
    <target>
      <target_id/>
      <mechanism_of_action/>
      <constants/>
      <references/>
    </target>
    <target>
      <target_id/>
      <mechanism_of_action/>
      <constants/>
      <references/>
    </target>
    <target>
      <target_id/>
      <mechanism_of_action/>
      <constants/>
      <references/>
    </target>
    <target>
      <target_id/>
      <mechanism_of_action/>
      <constants/>
      <references/>
    </target>
    <target>
      <target_id/>
      <mechanism_of_action/>
      <constants/>
      <references/>
    </target>
    <target>
      <target_id/>
      <mechanism_of_action/>
      <constants/>
      <references/>
    </target>
    <target>
      <target_id/>
      <mechanism_of_action/>
      <constants/>
      <references/>
    </target>
    <target>
      <target_id/>
      <mechanism_of_action/>
      <constants/>
      <references/>
    </target>
    <target>
      <target_id/>
      <mechanism_of_action/>
      <constants/>
      <references/>
    </target>
    <target>
      <target_id/>
      <mechanism_of_action/>
      <constants/>
      <references/>
    </target>
    <target>
      <target_id/>
      <mechanism_of_action/>
      <constants/>
      <references/>
    </target>
    <target>
      <target_id/>
      <mechanism_of_action/>
      <constants/>
      <references/>
    </target>
    <target>
      <target_id/>
      <mechanism_of_action/>
      <constants/>
      <references/>
    </target>
    <target>
      <target_id/>
      <mechanism_of_action/>
      <constants/>
      <references/>
    </target>
    <target>
      <target_id/>
      <mechanism_of_action/>
      <constants/>
      <references/>
    </target>
    <target>
      <target_id/>
      <mechanism_of_action/>
      <constants/>
      <references/>
    </target>
    <target>
      <target_id/>
      <mechanism_of_action/>
      <constants/>
      <references/>
    </target>
    <target>
      <target_id>BE0004631</target_id>
      <mechanism_of_action/>
      <constants/>
      <references/>
    </target>
    <target>
      <target_id>BE0003425</target_id>
      <mechanism_of_action/>
      <constants/>
      <references/>
    </target>
    <target>
      <target_id>BE0004497</target_id>
      <mechanism_of_action/>
      <constants/>
      <references/>
    </target>
    <target>
      <target_id>BE0002013</target_id>
      <mechanism_of_action/>
      <constants/>
      <references/>
    </target>
    <target>
      <target_id>BE0002794</target_id>
      <mechanism_of_action/>
      <constants/>
      <references/>
    </target>
    <target>
      <target_id>BE0002795</target_id>
      <mechanism_of_action/>
      <constants/>
      <references/>
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  </targets>
</compound>
