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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2006-05-22 14:17:34 UTC
Update Date2018-05-19 22:21:44 UTC
HMDB IDHMDB0002061
Secondary Accession Numbers
  • HMDB0006554
  • HMDB0010366
  • HMDB02061
  • HMDB06554
  • HMDB10366
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 humour, 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
ValueSource
HyaluronateGenerator
HyaluronanHMDB
Chemical Formula(C14H21NO11)nH2O
Average Molecular WeightNot Available
Monoisotopic Molecular WeightNot Available
IUPAC NameNot Available
Traditional NameNot Available
CAS Registry Number9004-61-9
SMILES
[H]O[C@H]1[C@H](O)[C@@H](CO)O[C@@H](O[C@H]2[C@H](O)[C@@H](O)[C@H](O)O[C@@H]2C(O)=O)[C@@H]1NC(C)=O
InChI Identifier
InChI=1S/C14H23NO12/c1-3(17)15-5-7(19)6(18)4(2-16)25-14(5)27-10-8(20)9(21)13(24)26-11(10)12(22)23/h4-11,13-14,16,18-21,24H,2H2,1H3,(H,15,17)(H,22,23)/t4-,5-,6-,7-,8-,9-,10+,11+,13-,14+/m1/s1
InChI KeyLJKKEBYAXYCTNF-GIXQJHCPSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as n-acyl-alpha-hexosamines. These are carbohydrate derivatives containing a hexose moiety in which the oxygen atom is replaced by an n-acyl group.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentN-acyl-alpha-hexosamines
Alternative Parents
Substituents
  • Fatty acyl glycoside
  • Fatty acyl glycoside of mono- or disaccharide
  • N-acyl-alpha-hexosamine
  • Glucuronic acid or derivatives
  • Disaccharide
  • Glycosyl compound
  • O-glycosyl compound
  • Pyran
  • Fatty acyl
  • Oxane
  • Acetamide
  • Secondary carboxylic acid amide
  • Secondary alcohol
  • Carboxamide group
  • Hemiacetal
  • Oxacycle
  • Organoheterocyclic compound
  • Polyol
  • Carboxylic acid derivative
  • Carboxylic acid
  • Acetal
  • Monocarboxylic acid or derivatives
  • Organic nitrogen compound
  • Carbonyl group
  • Organopnictogen compound
  • Organic oxide
  • Alcohol
  • Organonitrogen compound
  • Primary alcohol
  • Hydrocarbon derivative
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Physiological effect

Health effect:

Disposition

Source:

Biological location:

Role

Industrial application:

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-2.6ALOGPS
logS-0.53ALOGPS
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Extracellular
  • Lysosome
Biospecimen Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.053 +/- 0.015 uMAdult (>18 years old)BothNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified0.0644 +/- 0.0528 uMNot SpecifiedNot SpecifiedNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified0.214 +/- 0.0992 uMNot SpecifiedNot SpecifiedNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified0.24 (0.12-0.36) uMAdult (>18 years old)Not SpecifiedNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified1.2 (0.04-10.52) uMAdult (>18 years old)BothBiliary atresia details
BloodDetected and Quantified0.11 (0.044-0.74) uMNewborn (0-30 days old)BothHepatitis details
BloodDetected and Quantified0.11 +/- 0.013 uMAdult (>18 years old)Both
Diabetes
details
Cerebrospinal Fluid (CSF)Detected and Quantified>10.306 uMNot SpecifiedNot SpecifiedMeningitis details
Cerebrospinal Fluid (CSF)Detected and Quantified>5.153 uMNot SpecifiedNot Specified
Colon carcinoma
details
Cerebrospinal Fluid (CSF)Detected and Quantified0.0593-0.995 uMNot SpecifiedNot SpecifiedHead injury details
Cerebrospinal Fluid (CSF)Detected and Quantified0.25 (0.037-0.46) uMAdult (>18 years old)Not Specified
Epilepsy
details
Associated Disorders and Diseases
Disease References
Biliary atresia
  1. 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 ]
Diabetes mellitus type 2
  1. Mine S, Okada Y, Kawahara C, Tabata T, Tanaka Y: Serum hyaluronan concentration as a marker of angiopathy in patients with diabetes mellitus. Endocr J. 2006 Dec;53(6):761-6. Epub 2006 Sep 12. [PubMed:16966827 ]
Epilepsy
  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 ]
Head injury
  1. Burke EJ, Mehlhorn U, Allen SJ: Hyaluronan in cerebrospinal fluid after head injury. Acta Neurol (Napoli). 1994 Jun;16(3):103-9. [PubMed:7992658 ]
Hepatitis
  1. 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 ]
Meningitis
  1. Laurent UB, Laurent TC, Hellsing LK, Persson L, Hartman M, Lilja K: Hyaluronan in human cerebrospinal fluid. Acta Neurol Scand. 1996 Sep;94(3):194-206. [PubMed:8899053 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB022824
KNApSAcK IDNot Available
Chemspider ID8020685
KEGG Compound IDC00518
BioCyc IDNot Available
BiGG ID35227
Wikipedia LinkHyaluronic acid
METLIN IDNot Available
PubChem Compound53477741
PDB IDNot Available
ChEBI ID16336
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 ]

Only showing the first 10 proteins. There are 28 proteins in total.

Enzymes

General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGTs are of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isozyme is active on polyhydroxylated estrogens (such as estriol, 4-hydroxyestrone and 2-hydroxyestriol) and xenobiotics (such as 4-methylumbelliferone, 1-naphthol, 4-nitrophenol, 2-aminophenol, 4-hydroxybiphenyl and menthol). It is capable of 6 alpha-hydroxyglucuronidation of hyodeoxycholic acid.
Gene Name:
UGT2B4
Uniprot ID:
P06133
Molecular weight:
60512.035
General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate.
Gene Name:
UGT1A4
Uniprot ID:
P22310
Molecular weight:
60024.535
General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. Its unique specificity for 3,4-catechol estrogens and estriol suggests it may play an important role in regulating the level and activity of these potent and active estrogen metabolites. Is also active with androsterone, hyodeoxycholic acid and tetrachlorocatechol (in vitro).
Gene Name:
UGT2B7
Uniprot ID:
P16662
Molecular weight:
60720.15
General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone.
Gene Name:
UGT1A1
Uniprot ID:
P22309
Molecular weight:
59590.91
General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform has specificity for phenols.
Gene Name:
UGT1A9
Uniprot ID:
O60656
Molecular weight:
59940.495
General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform has specificity for phenols.
Gene Name:
UGT1A6
Uniprot ID:
P19224
Molecular weight:
60750.215
General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
Plays a role in hyaluronan/hyaluronic acid (HA) synthesis. Also able to catalyze the synthesis of chito-oligosaccharide depending on the substrate.
Gene Name:
HAS1
Uniprot ID:
Q92839
Molecular weight:
64831.425
General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
Plays a role in hyaluronan/hyaluronic acid (HA) synthesis.
Gene Name:
HAS3
Uniprot ID:
O00219
Molecular weight:
62997.73
General function:
Involved in binding
Specific function:
Receptor for hyaluronic acid (HA). Mediates cell-cell and cell-matrix interactions through its affinity for HA, and possibly also through its affinity for other ligands such as osteopontin, collagens, and matrix metalloproteinases (MMPs). Adhesion with HA plays an important role in cell migration, tumor growth and progression. Also involved in lymphocyte activation, recirculation and homing, and in hematopoiesis. Altered expression or dysfunction causes numerous pathogenic phenotypes. Great protein heterogeneity due to numerous alternative splicing and post-translational modification events
Gene Name:
CD44
Uniprot ID:
P16070
Molecular weight:
81537.0
General function:
Cell wall/membrane/envelope biogenesis
Specific function:
Plays a role in hyaluronan/hyaluronic acid (HA) synthesis.
Gene Name:
HAS2
Uniprot ID:
Q92819
Molecular weight:
63565.845

Only showing the first 10 proteins. There are 28 proteins in total.