Record Information
Version3.6
Creation Date2006-05-22 14:17:34 UTC
Update Date2013-05-29 19:33:39 UTC
HMDB IDHMDB02061
Secondary Accession Numbers
  • HMDB06554
Metabolite Identification
Common NameHyaluronic acid
DescriptionHyaluronic acid (HA), is the most abundant glycosaminoglycan (GAG) in mammalian tissue. It is present in high concentrations in connective tissue, such as skin, vitreous humor, cartilage, and umbilical cord, but the largest single reservoir is the synovial fluid (SF) of the diarthrodial joints, where concentrations of 0.5-4 mg/mL are achieved. Hyaluronic acid, is the major hydrodynamic nonprotein component of joint SF. Its unique viscoelastic properties confer remarkable shock absorbing and lubricating abilities to SF, while its enormous macromolecular size and hydrophilicity serve to retain fluid in the joint cavity during articulation. HA restricts the entry of large plasma proteins and cells into SF but facilitates solute exchange between the synovial capillaries and cartilage and other joint tissues. In addition, HA can form a pericellular coat around cells, interact with proinflammatory mediators, and bind to cell receptors, such as cluster determinant (CD)44 and receptor for hyaluronate-mediated motility (RHAMM), where it modulates cell proliferation, migration, and gene expression. All these physicochemical and biologic properties of HA have been shown to be molecular weight (MW) dependent. The diverse physicochemical properties of HA arise from its unique macromolecular structure. The HA is an exceptionally long (3-30 μm) and unbranched nonsulfated GAG composed of repeating disaccharide units of N-acetylglucosamine, and glucuronic acid glycosidically linked through their respective 1-4 ring positions. Hydroxyl group oxygens at the glucuronyl-1 and glucosamine 3-positions are used for further polymerization of the HA disaccharide units to form chains that, when released from the cell plasma membrane, are of variable length and thus polydispersity. Despite the simplicity of the HA primary structure, this linear polyelectrolyte adopts complex conformations in solution, which engender it with diverse biologic properties. Within the joint cavity, HA molecules are predominately synthesized by the type B synovial cells. (PMID 12219318 ).
Structure
Thumb
Synonyms
  1. Hyaluronic acid
Chemical FormulaC16H27NO12
Average Molecular Weight425.3851
Monoisotopic Molecular Weight425.153325333
IUPAC Name(2S,3S,4R,5R)-6-{[(2R,3R,4R,5S,6R)-3-acetamido-5-hydroxy-6-(hydroxymethyl)-2-methoxyoxan-4-yl]oxy}-4,5-dihydroxy-3-methoxyoxane-2-carboxylic acid
Traditional IUPAC Name(2S,3S,4R,5R)-6-{[(2R,3R,4R,5S,6R)-3-acetamido-5-hydroxy-6-(hydroxymethyl)-2-methoxyoxan-4-yl]oxy}-4,5-dihydroxy-3-methoxyoxane-2-carboxylic acid
CAS Registry Number9004-61-9
SMILES
CO[C@@H]1O[C@H](CO)[C@@H](O)[C@H](OC2O[C@@H]([C@@H](OC)[C@H](O)[C@H]2O)C(O)=O)[C@H]1NC(C)=O
InChI Identifier
InChI=1S/C16H27NO12/c1-5(19)17-7-11(8(20)6(4-18)27-15(7)26-3)28-16-10(22)9(21)12(25-2)13(29-16)14(23)24/h6-13,15-16,18,20-22H,4H2,1-3H3,(H,17,19)(H,23,24)/t6-,7-,8-,9-,10-,11-,12+,13+,15-,16?/m1/s1
InChI KeyOEANUJAFZLQYOD-DDKBAWAXSA-N
Chemical Taxonomy
KingdomOrganic Compounds
Super ClassCarbohydrates and Carbohydrate Conjugates
ClassDisaccharides
Sub ClassDihexoses
Other Descriptors
  • Aliphatic Heteropolycyclic Compounds
Substituents
  • 1,2 Diol
  • Acetal
  • Carboxamide Group
  • Carboxylic Acid
  • Dialkyl Ether
  • Glucosamine
  • Glucuronic Acid Or Derivative
  • Glucuronide
  • Glycosyl Compound
  • Mannosamine
  • O Glycosyl Compound
  • Oxane
  • Primary Alcohol
  • Secondary Alcohol
  • Secondary Carboxylic Acid Amide
  • Sugar Acid
Direct ParentDihexoses
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Extracellular
  • Lysosome
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
water solubility95.1 g/LALOGPS
logP-1.9ALOGPS
logP-3.4ChemAxon
logS-0.65ALOGPS
pKa (strongest acidic)3.19ChemAxon
pKa (strongest basic)-0.78ChemAxon
physiological charge-1ChemAxon
hydrogen acceptor count12ChemAxon
hydrogen donor count6ChemAxon
polar surface area193.47ChemAxon
rotatable bond count7ChemAxon
refractivity88.81ChemAxon
polarizability40.08ChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Extracellular
  • Lysosome
Biofluid Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReference
Cerebrospinal Fluid (CSF)Detected and Quantified0.24 (0.12-0.36) uMAdult (>18 years old)Not SpecifiedNormal
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReference
BloodDetected and Quantified1.2 (0.04-10.52) uMAdult (>18 years old)BothBiliary atresia
BloodDetected and Quantified0.11 (0.044-0.74) uMNewborn (0-30 days old)BothHepatitis
Cerebrospinal Fluid (CSF)Detected and Quantified0.25 (0.037-0.46) uMAdult (>18 years old)Not SpecifiedCommentEpilepsy
Associated Disorders and Diseases
Disease References
Biliary atresia
  • Ukarapol N, Wongsawasdi L, Ong-Chai S, Riddhiputra P, Kongtawelert P: Hyaluronic acid: additional biochemical marker in the diagnosis of biliary atresia. Pediatr Int. 2007 Oct;49(5):608-11. Pubmed: 17875085
Epilepsy
  • Perosa SR, Porcionatto MA, Cukiert A, Martins JR, Amado D, Nader HB, Cavalheiro EA, Leite JP, Naffah-Mazzacoratti MG: Extracellular matrix components are altered in the hippocampus, cortex, and cerebrospinal fluid of patients with mesial temporal lobe epilepsy. Epilepsia. 2002;43 Suppl 5:159-61. Pubmed: 12121313
Hepatitis
  • Ukarapol N, Wongsawasdi L, Ong-Chai S, Riddhiputra P, Kongtawelert P: Hyaluronic acid: additional biochemical marker in the diagnosis of biliary atresia. Pediatr Int. 2007 Oct;49(5):608-11. Pubmed: 17875085
Associated OMIM IDs
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB022824
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDC00518
BioCyc IDNot Available
BiGG ID35227
Wikipedia LinkHyaluronic acid
NuGOwiki LinkHMDB02061
Metagene LinkHMDB02061
METLIN IDNot Available
PubChem Compound53477741
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceTan, Wensong; Hu, Yihong; Zhang, Xu; Cai, Haibo. Method for preparing hyaluronic acid from microbial fermentation broth. Faming Zhuanli Shenqing Gongkai Shuomingshu (2007), 10pp.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Perosa SR, Porcionatto MA, Cukiert A, Martins JR, Amado D, Nader HB, Cavalheiro EA, Leite JP, Naffah-Mazzacoratti MG: Extracellular matrix components are altered in the hippocampus, cortex, and cerebrospinal fluid of patients with mesial temporal lobe epilepsy. Epilepsia. 2002;43 Suppl 5:159-61. Pubmed: 12121313
  2. Ghosh P, Guidolin D: Potential mechanism of action of intra-articular hyaluronan therapy in osteoarthritis: are the effects molecular weight dependent? Semin Arthritis Rheum. 2002 Aug;32(1):10-37. Pubmed: 12219318

Enzymes

Gene Name:
UGT2B4
Uniprot ID:
P06133
Gene Name:
UGT1A4
Uniprot ID:
P22310
Gene Name:
UGT2B7
Uniprot ID:
P16662
Gene Name:
UGT1A1
Uniprot ID:
P22309
Gene Name:
UGT1A9
Uniprot ID:
O60656
Gene Name:
UGT1A6
Uniprot ID:
P19224
Gene Name:
HAS1
Uniprot ID:
Q92839
Gene Name:
HAS3
Uniprot ID:
O00219
Gene Name:
CD44
Uniprot ID:
P16070
Gene Name:
HAS2
Uniprot ID:
Q92819
Gene Name:
ACAN
Uniprot ID:
P16112
Gene Name:
NCAN
Uniprot ID:
O14594
Gene Name:
BCAN
Uniprot ID:
Q96GW7
Gene Name:
VCAN
Uniprot ID:
P13611
Gene Name:
STAB2
Uniprot ID:
Q8WWQ8
Gene Name:
STAB1
Uniprot ID:
Q9NY15
Gene Name:
LAYN
Uniprot ID:
Q6UX15
Gene Name:
SUSD5
Uniprot ID:
O60279