Succinyladenosine (CHEM003240)

Record Information
Version1.0
Creation Date2014-08-29 06:13:18 UTC
Update Date2026-04-06 13:22:15 UTC
Accession NumberCHEM003240
Identification
Common NameSuccinyladenosine
ClassSmall Molecule
Description
Succinyladenosine (SAdo) is one of the dephosphorylated enzyme substrate that accumulates in body fluids of patients with adenylosuccinate lyase (ADSL) deficiency, the other being 5-amino-4-imidazole-N-succinocarboxamide riboside (SAICAr). ADSL is an inherited metabolic disease characterized by various degrees of psychomotor retardation. The severity of the clinical presentation correlates with a low S-Ado/SAICAr ratio in body fluids. Normally Succinyladenosine is not found in blood or CSF but may be detected in trace amounts in urine. (OMIM 103050). (1, 2).
Contaminant Sources
  • FooDB Chemicals
  • HMDB Contaminants - Urine
  • T3DB toxins
Contaminant Type
  • Amine
  • Animal Toxin
  • Ether
  • Food Toxin
  • Metabolite
  • Natural Compound
  • Organic Compound
Chemical Structure
MOLSDF3D SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
(S)-N-(1,2-Dicarboxyethyl)-adenosineChEBI
6-(1,2-Dicarboxyethylamino)-9-beta-D-ribofuranosylpurineChEBI
N-(9-beta-D-Ribofuranosyl-9H-purin-6-yl)-L-aspartic acidChEBI
N-9-Ribofuranosyl-9H-purin-6-yl-aspartic acidChEBI
SuccinoadenosineChEBI
6-(1,2-Dicarboxyethylamino)-9-b-D-ribofuranosylpurineGenerator
6-(1,2-Dicarboxyethylamino)-9-β-D-ribofuranosylpurineGenerator
N-(9-b-D-Ribofuranosyl-9H-purin-6-yl)-L-aspartateGenerator
N-(9-b-D-Ribofuranosyl-9H-purin-6-yl)-L-aspartic acidGenerator
N-(9-beta-D-Ribofuranosyl-9H-purin-6-yl)-L-aspartateGenerator
N-(9-Β-D-ribofuranosyl-9H-purin-6-yl)-L-aspartateGenerator
N-(9-Β-D-ribofuranosyl-9H-purin-6-yl)-L-aspartic acidGenerator
N-9-Ribofuranosyl-9H-purin-6-yl-aspartateGenerator
6-(1,2-Dicarboxyethylamino)-9-beta-delta-ribofuranosylpurineHMDB
N-(9-beta-delta-Ribofuranosyl-9H-purin-6-yl)-L-aspartateHMDB
N-(9-beta-delta-Ribofuranosyl-9H-purin-6-yl)-L-aspartic acidHMDB
Chemical FormulaC14H17N5O8
Average Molecular Mass383.314 g/mol
Monoisotopic Mass383.108 g/mol
CAS Registry Number4542-23-8
IUPAC Name(2S)-2-({9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-9H-purin-6-yl}amino)butanedioic acid
Traditional Nameatp - adenosine triphosphate
SMILESOC[C@H]1O[C@H]([C@H](O)[C@@H]1O)N1C=NC2=C(N[C@@H](CC(O)=O)C(O)=O)N=CN=C12
InChI IdentifierInChI=1S/C14H17N5O8/c20-2-6-9(23)10(24)13(27-6)19-4-17-8-11(15-3-16-12(8)19)18-5(14(25)26)1-7(21)22/h3-6,9-10,13,20,23-24H,1-2H2,(H,21,22)(H,25,26)(H,15,16,18)/t5-,6+,9+,10+,13+/m0/s1
InChI KeyVKGZCEJTCKHMRL-VWJPMABRSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as purine nucleosides. Purine nucleosides are compounds comprising a purine base attached to a ribosyl or deoxyribosyl moiety.
KingdomOrganic compounds
Super ClassNucleosides, nucleotides, and analogues
ClassPurine nucleosides
Sub ClassNot Available
Direct ParentPurine nucleosides
Alternative Parents
Substituents
  • Purine nucleoside
  • Aspartic acid or derivatives
  • Glycosyl compound
  • N-glycosyl compound
  • 6-alkylaminopurine
  • 6-aminopurine
  • Alpha-amino acid or derivatives
  • Pentose monosaccharide
  • L-alpha-amino acid
  • Imidazopyrimidine
  • Purine
  • Aminopyrimidine
  • Secondary aliphatic/aromatic amine
  • N-substituted imidazole
  • Monosaccharide
  • Pyrimidine
  • Dicarboxylic acid or derivatives
  • Imidolactam
  • Heteroaromatic compound
  • Imidazole
  • Tetrahydrofuran
  • Azole
  • Amino acid or derivatives
  • Secondary alcohol
  • Amino acid
  • Carboxylic acid derivative
  • Carboxylic acid
  • Oxacycle
  • Azacycle
  • Organoheterocyclic compound
  • Secondary amine
  • Organic oxygen compound
  • Alcohol
  • Organic nitrogen compound
  • Carbonyl group
  • Hydrocarbon derivative
  • Amine
  • Organopnictogen compound
  • Organic oxide
  • Primary alcohol
  • Organooxygen compound
  • Organonitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginEndogenous
Cellular Locations
  • Cytoplasm
  • Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
Pathways
NameSMPDB LinkKEGG Link
Adenylosuccinate Lyase DeficiencySMP00167 Not Available
ApplicationsNot Available
Biological Roles
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting Point233 - 238°C
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility7.62 g/LALOGPS
logP-1.3ALOGPS
logP-3.9ChemAxon
logS-1.7ALOGPS
pKa (Strongest Acidic)3.14ChemAxon
pKa (Strongest Basic)4.58ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count12ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area200.15 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity85.3 m³·mol⁻¹ChemAxon
Polarizability34.83 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
External Links
DrugBank IDNot Available
HMDB IDHMDB0000912
FooDB IDFDB022314
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN ID5867
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID17216022
ChEBI ID71169
PubChem Compound ID20849086
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceBuck, Ildiko; Reese, Colin B. An unambiguous synthesis of adenylosuccinic acid and its constituent nucleoside. Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999) (1990), (11), 2937-42.
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=22770225
2. Buck, Ildiko; Reese, Colin B. An unambiguous synthesis of adenylosuccinic acid and its constituent nucleoside. Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999) (1990), (11), 2937-42.
3. Marinaki AM, Champion M, Kurian MA, Simmonds HA, Marie S, Vincent MF, van den Berghe G, Duley JA, Fairbanks LD: Adenylosuccinate lyase deficiency--first British case. Nucleosides Nucleotides Nucleic Acids. 2004 Oct;23(8-9):1231-3.
4. Tsuchiya H, Hayashi T, Tatsumi M, Hoshino Y, Ohtani S, Takagi N: High-performance liquid-chromatographic analysis for serotonin and tryptamine excreted in urine after oral loading with L-tryptophan. Clin Chem. 1989 Jan;35(1):43-7.
5. Zikanova M, Krijt J, Hartmannova H, Kmoch S: Preparation of 5-amino-4-imidazole-N-succinocarboxamide ribotide, 5-amino-4-imidazole-N-succinocarboxamide riboside and succinyladenosine, compounds usable in diagnosis and research of adenylosuccinate lyase deficiency. J Inherit Metab Dis. 2005;28(4):493-9.
6. Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043.