Hyaluronic acid (CED0000959)

Record Information
Version1.0
Creation Date2016-05-25 02:54:43 UTC
Update Date2026-05-14 18:59:49 UTC
Accession NumberCHEM021071
Identification
Common NameHyaluronic acid
ClassSmall Molecule
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.
Contaminant TypeNot Available
Chemical Structure
Synonyms
ValueSource
(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-carboxylateGenerator
Advanced medical optics, inc. brand OF sodium hyaluronateMeSH
Vitrax, amoMeSH
Anika therapeutics brand OF sodium hyaluronidateMeSH
HyaluronanMeSH
LuronitMeSH
Advanced medical optics brand OF sodium hyaluronidateMeSH
Hyaluronate, sodiumMeSH
HyviscMeSH
Bausch and lomb brand OF sodium hyaluronateMeSH
HealonMeSH
Akorn, inc. brand OF sodium hyaluronateMeSH
AmviscMeSH
Hyaluronic acidMeSH
Sodium hyaluronateMeSH
Acid, hyaluronicMeSH
BiolonMeSH
EtamucineMeSH
amo VitraxMeSH
Hyaluronate sodiumMeSH
Chemical FormulaC28H44N2O23
Average Molecular Mass776.651 g/mol
Monoisotopic Mass776.233 g/mol
CAS Registry Number9004-61-9
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
Traditional 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
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
InChI IdentifierInChI=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 KeyKIUKXJAPPMFGSW-YXBJCWEESA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as acylaminosugars. These are organic compounds containing a sugar linked to a chain through N-acyl group.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentAcylaminosugars
Alternative Parents
Substituents
  • Oligosaccharide
  • Acylaminosugar
  • Fatty acyl glycoside
  • N-acyl-alpha-hexosamine
  • 1-o-glucuronide
  • O-glucuronide
  • Glucuronic acid or derivatives
  • Glycosyl compound
  • O-glycosyl compound
  • Beta-hydroxy acid
  • Dicarboxylic acid or derivatives
  • Fatty acyl
  • Hydroxy acid
  • Pyran
  • Oxane
  • Acetamide
  • Carboxamide group
  • Hemiacetal
  • Secondary carboxylic acid amide
  • Secondary alcohol
  • Organoheterocyclic compound
  • Oxacycle
  • Carboxylic acid
  • Carboxylic acid derivative
  • Acetal
  • Polyol
  • Alcohol
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Carbonyl group
  • Organopnictogen compound
  • Primary alcohol
  • Organonitrogen compound
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Organoleptic EffectsNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility49.3 g/LALOGPS
logP-1.5ALOGPS
logP-6.5ChemAxon
logS-1.2ALOGPS
pKa (Strongest Acidic)2.82ChemAxon
pKa (Strongest Basic)-3.9ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count25ChemAxon
Hydrogen Donor Count14ChemAxon
Polar Surface Area406.69 ŲChemAxon
Rotatable Bond Count12ChemAxon
Refractivity156.14 m³·mol⁻¹ChemAxon
Polarizability69.68 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0kh9-0161041900-23dbeae71feb68faba23Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0ul0-0393061200-98666fd29b2d88284aeeNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0fl0-2293030100-1541dad352da9d355ce7Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-055r-2201024900-d62ed872f6e6d1ec5742Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-05fr-2262143900-e0a1be3ef6be58bedad9Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0fk9-5791400000-ff79477bea6365468e55Not AvailableView Spectrum
Toxicity Profile
Mechanism of ToxicityNot Available
Carcinogenicity (IARC Classification)Not Available
Minimum Risk LevelNot Available
SymptomsNot Available
TreatmentNot Available
Toxicity ValuesNot Available
Health Effects
Health EffectRelationshipDirectionReference
Exposure Sources
Source IDSourceSectorReference
302CicatrizantsHealthcare, pharmaceuticals & veterinary productsNot Available
368Drugs for disorders of the musculo-skeletal systemHealthcare, pharmaceuticals & veterinary productsNot Available
389Nasal preparationsHealthcare, pharmaceuticals & veterinary productsNot Available
403Surgical aidsHealthcare, pharmaceuticals & veterinary productsNot Available
490Personal care & cosmeticsNot Available
510Communication Cables Or ConductorsElectrical & Electronic EquipmentNot Available
548Preparation Of VinegarFood, food processing & cookwareNot Available
549Preparation Of Wine Or Sparkling WineFood, food processing & cookwareNot Available
559Non Electric Simulated Smoking DevicesHousehold cleaning & consumer productsNot Available
560Other Smoking RequisitesHousehold cleaning & consumer productsNot Available
564Soap DispensersHousehold cleaning & consumer productsNot Available
612Body Washing Or Cleaning ImplementsPersonal care & cosmeticsNot Available
616Face Mask CosmeticsPersonal care & cosmeticsNot Available
638Decorating TextilesTextiles, leather & furnishingsNot Available
643HeadwearTextiles, leather & furnishingsNot Available
655Slide FastenersTextiles, leather & furnishingsNot Available
656Snap FastenersTextiles, leather & furnishingsNot Available
658Touch FastenersTextiles, leather & furnishingsNot Available
661UmbrellasTextiles, leather & furnishingsNot Available
Pathways
2 pathways
Targets
StructureProteinUniProt IDOrganismRelationshipDetails
CD44 antigen structureClick to view 3D structureCD44 antigenP16070HumansPredicted (SEA)0.0778492
Click to view 3D structureCD44 antigenP15379Mus musculusPredicted (SEA)0.0778492
Click to view 3D structureEndopolygalactyuronaseP79074Chondrostereum purpureumPredicted (SEA)0.0778492
Neurotrophic factor BDNF precursor form structureClick to view 3D structureNeurotrophic factor BDNF precursor formP23560HumansPredicted (SEA)0.389246
Pleiotrophin structureClick to view 3D structurePleiotrophinP21246HumansPredicted (SEA)0.389246
Click to view 3D structureN-acetyllactosaminide alpha-1,3-galactosyltransferaseP50127Sus scrofaPredicted (SEA)1.16774
Click to view 3D structureCMP-N-acetylneuraminate-beta-galactosamide-alpha-2,3-sialyltransferase 1P54751Mus musculusPredicted (SEA)2.17978
Click to view 3D structureEndo-beta-N-acetylglucosaminidaseQ9ZB22Arthrobacter protophormiaePredicted (SEA)1.01204
Click to view 3D structureAlpha-amylaseQ7M328Sus scrofa domesticusPredicted (SEA)0.622794
Click to view 3D structureLectinB4EH87Burkholderia cenocepacia (strain ATCC BAA-245 / DSM 16553 / LMG 16656/ NCTC 13227 / J2315 / CF5610) (Burkholderia cepacia (strain J2315))Predicted (SEA)3.42537
Click to view 3D structureType 1 fimbrin D-mannose specific adhesinP08191Escherichia coli K-12Predicted (SEA)3.97031
Click to view 3D structureKiller cell lectin-like receptor subfamily B member 1AP27471Rattus norvegicusPredicted (SEA)0.622794
Galectin-3 structureClick to view 3D structureGalectin-3P17931HumansPredicted (SEA)10.2761
Click to view 3D structureE-selectinP98105Rattus norvegicusPredicted (SEA)1.01204
Interferon gamma structureClick to view 3D structureInterferon gammaP01579HumansPredicted (SEA)0.934191
Gap junction beta-2 protein structureClick to view 3D structureGap junction beta-2 proteinP29033HumansPredicted (SEA)1.40129
Midkine structureClick to view 3D structureMidkineP21741HumansPredicted (SEA)0.544945
Click to view 3D structureSolute carrier organic anion transporter family member 1B2Q9QZX8Rattus norvegicusPredicted (SEA)3.34752
Click to view 3D structureOligo-1,6-glucosidase IMA1P53051Saccharomyces cerevisiae S288cPredicted (SEA)16.3483
Bone morphogenetic protein 6 structureClick to view 3D structureBone morphogenetic protein 6P22004HumansPredicted (SEA)1.40129
Platelet factor 4 structureClick to view 3D structurePlatelet factor 4P02776HumansPredicted (SEA)1.40129
Carbonic anhydrase 12 structureClick to view 3D structureCarbonic anhydrase 12O43570HumansPredicted (SEA)717.614
Carbonic anhydrase 7 structureClick to view 3D structureCarbonic anhydrase 7P43166HumansPredicted (SEA)654.011
Carbonic anhydrase 1 structureClick to view 3D structureCarbonic anhydrase 1P00915HumansPredicted (SEA)1074.94
Sialic acid-binding Ig-like lectin 7 structureClick to view 3D structureSialic acid-binding Ig-like lectin 7Q9Y286HumansPredicted (SEA)1.01204
Concentrations
Not Available
External Links
DrugBank IDNot Available
HMDB IDNot Available
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider IDNot Available
ChEBI IDNot Available
PubChem Compound ID24728612
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References