<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <version>1.0</version>
  <creation_date>2016-05-25 02:54:43 UTC</creation_date>
  <update_date>2026-05-14 18:59:49 UTC</update_date>
  <accession/>
  <common_name>Hyaluronic acid</common_name>
  <class>SmallMolecule</class>
  <description>Hyaluronic acid belongs to the carbohydrates and carbohydrate conjugates, a subclass of organooxygen compounds within the organic compounds. With an average molecular weight of 776.65 g/mol, Hyaluronic acid is a heavy molecule. It has the chemical formula C28H44N2O23. In industrial applications, the compound is used as a humectant, an anti-static agent, and a softener and conditioner.

The compound is found in or released from ten recorded sources. Within healthcare, pharmaceuticals, and veterinary products, it is utilized in surgical aids, nasal preparations, drugs for disorders of the musculo-skeletal system, and cicatrizants. It is also present in household cleaning and consumer products, specifically soap dispensers, other smoking requisites, and non-electric simulated smoking devices. Additionally, it is found in communication cables or conductors within electrical and electronic equipment, and in the preparation of wine or sparkling wine and the preparation of vinegar. Recorded exposure routes include oral, topical, dental, vaginal, cutaneous, intra-articular, and intraepidermal.

Hyaluronic acid interacts with 15 recorded protein targets. It acts as a binder/inhibitor and a binder/modulator of the CD44 antigen, the hyaluronan mediated motility receptor (HMMR), the intercellular adhesion molecule 1 (ICAM1), and the neurocan core protein (NCAN), as well as 11 other proteins.</description>
  <categories/>
  <types/>
  <synonyms/>
  <chemical_formula>C28H44N2O23</chemical_formula>
  <average_molecular_weight>776.651</average_molecular_weight>
  <monisotopic_moleculate_weight>776.233485685</monisotopic_moleculate_weight>
  <iupac_name>(2S,4S,5R,6S)-6-{[(2S,3R,5S,6R)-2-{[(3S,4R,5R,6R)-2-carboxy-6-{[(3R,4R,5S,6R)-2,5-dihydroxy-3-[(1-hydroxyethylidene)amino]-6-(hydroxymethyl)oxan-4-yl]oxy}-4,5-dihydroxyoxan-3-yl]oxy}-5-hydroxy-3-[(1-hydroxyethylidene)amino]-6-(hydroxymethyl)oxan-4-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid</iupac_name>
  <traditional_iupac>(2S,4S,5R,6S)-6-{[(2S,3R,5S,6R)-2-{[(3S,4R,5R,6R)-2-carboxy-6-{[(3R,4R,5S,6R)-2,5-dihydroxy-3-[(1-hydroxyethylidene)amino]-6-(hydroxymethyl)oxan-4-yl]oxy}-4,5-dihydroxyoxan-3-yl]oxy}-5-hydroxy-3-[(1-hydroxyethylidene)amino]-6-(hydroxymethyl)oxan-4-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid</traditional_iupac>
  <cas_registry_number>9004-61-9</cas_registry_number>
  <smiles>[H]C1(O)O[C@]([H])(CO)[C@@]([H])(O)[C@]([H])(O[C@]2([H])OC([H])(C(O)=O)[C@@]([H])(O[C@]3([H])O[C@]([H])(CO)[C@@]([H])(O)C([H])(O[C@@]4([H])O[C@]([H])(C(O)=O)C([H])(O)[C@]([H])(O)[C@@]4([H])O)[C@@]3([H])N=C(C)O)[C@]([H])(O)[C@@]2([H])O)[C@@]1([H])N=C(C)O</smiles>
  <inchi>InChI=1S/C28H44N2O23/c1-5(33)29-9-18(11(35)7(3-31)47-25(9)46)49-28-17(41)15(39)20(22(53-28)24(44)45)51-26-10(30-6(2)34)19(12(36)8(4-32)48-26)50-27-16(40)13(37)14(38)21(52-27)23(42)43/h7-22,25-28,31-32,35-41,46H,3-4H2,1-2H3,(H,29,33)(H,30,34)(H,42,43)(H,44,45)/t7-,8-,9-,10-,11-,12-,13+,14?,15-,16-,17-,18-,19?,20+,21+,22?,25?,26+,27+,28-/m1/s1</inchi>
  <inchikey>KIUKXJAPPMFGSW-YXBJCWEESA-N</inchikey>
  <taxonomy>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic oxygen compounds</super_class>
    <class>Organooxygen compounds</class>
    <sub_class>Carbohydrates and carbohydrate conjugates</sub_class>
    <direct_parent>Acylaminosugars</direct_parent>
    <alternate_parents>
      <alternative_parent>Acetals</alternative_parent>
      <alternative_parent>Acetamides</alternative_parent>
      <alternative_parent>Beta hydroxy acids and derivatives</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Dicarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Fatty acyl glycosides</alternative_parent>
      <alternative_parent>Hemiacetals</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>N-acyl-alpha-hexosamines</alternative_parent>
      <alternative_parent>O-glucuronides</alternative_parent>
      <alternative_parent>O-glycosyl compounds</alternative_parent>
      <alternative_parent>Oligosaccharides</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organonitrogen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Oxanes</alternative_parent>
      <alternative_parent>Polyols</alternative_parent>
      <alternative_parent>Primary alcohols</alternative_parent>
      <alternative_parent>Pyrans</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Secondary carboxylic acid amides</alternative_parent>
    </alternate_parents>
    <substituents>
      <substituent>1-o-glucuronide</substituent>
      <substituent>Acetal</substituent>
      <substituent>Acetamide</substituent>
      <substituent>Acylaminosugar</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic heteromonocyclic compound</substituent>
      <substituent>Beta-hydroxy acid</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxamide group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Dicarboxylic acid or derivatives</substituent>
      <substituent>Fatty acyl</substituent>
      <substituent>Fatty acyl glycoside</substituent>
      <substituent>Glucuronic acid or derivatives</substituent>
      <substituent>Glycosyl compound</substituent>
      <substituent>Hemiacetal</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxy acid</substituent>
      <substituent>N-acyl-alpha-hexosamine</substituent>
      <substituent>O-glucuronide</substituent>
      <substituent>O-glycosyl compound</substituent>
      <substituent>Oligosaccharide</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Oxane</substituent>
      <substituent>Polyol</substituent>
      <substituent>Primary alcohol</substituent>
      <substituent>Pyran</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Secondary carboxylic acid amide</substituent>
    </substituents>
    <molecular_framework>Aliphatic heteromonocyclic compounds</molecular_framework>
    <descriptors/>
  </taxonomy>
  <status>Detected and Not Quantified</status>
  <origin/>
  <cellular_locations/>
  <biofluid_locations/>
  <tissue_locations/>
  <pathways>
    <pathway>
      <name>Hyaluronic acid Drug Metabolism</name>
      <smpdb_id>SMP0130655</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Hyaluronic acid Drug Metabolism Action Pathway</name>
      <smpdb_id>SMP0144174</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <state/>
  <appearance/>
  <experimental_properties>
    <property>
      <kind>logp</kind>
      <value>-8.2</value>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-1.51</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.20</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>solubility</kind>
      <value>4.93e+01 g/l</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-6.5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>2.82</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-3.9</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(2S,4S,5R,6S)-6-{[(2S,3R,5S,6R)-2-{[(3S,4R,5R,6R)-2-carboxy-6-{[(3R,4R,5S,6R)-2,5-dihydroxy-3-[(1-hydroxyethylidene)amino]-6-(hydroxymethyl)oxan-4-yl]oxy}-4,5-dihydroxyoxan-3-yl]oxy}-5-hydroxy-3-[(1-hydroxyethylidene)amino]-6-(hydroxymethyl)oxan-4-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>776.651</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>776.233485685</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>[H]C1(O)O[C@]([H])(CO)[C@@]([H])(O)[C@]([H])(O[C@]2([H])OC([H])(C(O)=O)[C@@]([H])(O[C@]3([H])O[C@]([H])(CO)[C@@]([H])(O)C([H])(O[C@@]4([H])O[C@]([H])(C(O)=O)C([H])(O)[C@]([H])(O)[C@@]4([H])O)[C@@]3([H])N=C(C)O)[C@]([H])(O)[C@@]2([H])O)[C@@]1([H])N=C(C)O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C28H44N2O23</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C28H44N2O23/c1-5(33)29-9-18(11(35)7(3-31)47-25(9)46)49-28-17(41)15(39)20(22(53-28)24(44)45)51-26-10(30-6(2)34)19(12(36)8(4-32)48-26)50-27-16(40)13(37)14(38)21(52-27)23(42)43/h7-22,25-28,31-32,35-41,46H,3-4H2,1-2H3,(H,29,33)(H,30,34)(H,42,43)(H,44,45)/t7-,8-,9-,10-,11-,12-,13+,14?,15-,16-,17-,18-,19?,20+,21+,22?,25?,26+,27+,28-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>KIUKXJAPPMFGSW-YXBJCWEESA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>406.69</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>156.14</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>69.68</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>12</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>25</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>14</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-2</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:0x00007f7276bf9740&gt;</health_effects>
  <symptoms/>
  <treatment/>
  <drugbank_id>DB08818</drugbank_id>
  <hmdb_id/>
  <pubchem_compound_id>3084050</pubchem_compound_id>
  <chembl_id/>
  <chemspider_id>2341173</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>BE0001113</target_id>
      <mechanism_of_action/>
      <constants/>
      <references/>
    </target>
    <target>
      <target_id>BE0001085</target_id>
      <mechanism_of_action/>
      <constants/>
      <references/>
    </target>
    <target>
      <target_id>BE0004702</target_id>
      <mechanism_of_action/>
      <constants/>
      <references/>
    </target>
    <target>
      <target_id>BE0004512</target_id>
      <mechanism_of_action/>
      <constants/>
      <references/>
    </target>
    <target>
      <target_id>BE0004606</target_id>
      <mechanism_of_action/>
      <constants/>
      <references/>
    </target>
    <target>
      <target_id>BE0004930</target_id>
      <mechanism_of_action/>
      <constants/>
      <references/>
    </target>
    <target>
      <target_id>BE0004933</target_id>
      <mechanism_of_action/>
      <constants/>
      <references/>
    </target>
    <target>
      <target_id>BE0004935</target_id>
      <mechanism_of_action/>
      <constants/>
      <references/>
    </target>
    <target>
      <target_id>BE0004940</target_id>
      <mechanism_of_action/>
      <constants/>
      <references/>
    </target>
    <target>
      <target_id>BE0004944</target_id>
      <mechanism_of_action/>
      <constants/>
      <references/>
    </target>
    <target>
      <target_id>BE0004948</target_id>
      <mechanism_of_action/>
      <constants/>
      <references/>
    </target>
    <target>
      <target_id>BE0004952</target_id>
      <mechanism_of_action/>
      <constants/>
      <references/>
    </target>
    <target>
      <target_id>BE0004942</target_id>
      <mechanism_of_action/>
      <constants/>
      <references/>
    </target>
    <target>
      <target_id>BE0004943</target_id>
      <mechanism_of_action/>
      <constants/>
      <references/>
    </target>
    <target>
      <target_id>BE0010044</target_id>
      <mechanism_of_action/>
      <constants/>
      <references/>
    </target>
  </targets>
</compound>
