Human Metabolome Database Version 3.5

Showing metabocard for Hyaluronic acid (HMDB02061)

Record Information
Version 3.5
Creation Date 2006-05-22 08:17:34 -0600
Update Date 2013-05-29 13:33:39 -0600
HMDB ID HMDB02061
Secondary Accession Numbers
  • HMDB06554
Metabolite Identification
Common Name Hyaluronic acid
Description Hyaluronic 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 Link_out).
Structure Thumb
Download: MOL | SDF | PDB | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. Hyaluronic acid
Chemical Formula C16H27NO12
Average Molecular Weight 425.3851
Monoisotopic Molecular Weight 425.153325333
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 Number 9004-61-9
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 Key OEANUJAFZLQYOD-DDKBAWAXSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Carbohydrates and Carbohydrate Conjugates
Class Disaccharides
Sub Class Dihexoses
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 Parent Dihexoses
Ontology
Status Detected and Quantified
Origin
  • Endogenous
Biofunction Not Available
Application Not Available
Cellular locations
  • Extracellular
  • Lysosome
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point Not Available Not Available
Boiling Point Not Available Not Available
Water Solubility Not Available Not Available
LogP Not Available Not Available
Predicted Properties
Property Value Source
Water Solubility 95.1 g/L ALOGPS
LogP -1.87 ALOGPS
LogP -3.4 ChemAxon
LogS -0.65 ALOGPS
pKa (strongest acidic) 3.19 ChemAxon
pKa (strongest basic) -0.78 ChemAxon
Hydrogen Acceptor Count 12 ChemAxon
Hydrogen Donor Count 6 ChemAxon
Polar Surface Area 193.47 A2 ChemAxon
Rotatable Bond Count 7 ChemAxon
Refractivity 88.81 ChemAxon
Polarizability 40.08 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge -1 ChemAxon
Spectra
Not Available
Biological Properties
Cellular Locations
  • Extracellular
  • Lysosome
Biofluid Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
Tissue Location Not Available
Pathways Not Available
Normal Concentrations
Biofluid Status Value Age Sex Condition Reference
Cerebrospinal Fluid (CSF) Detected and Quantified
0.24 (0.12-0.36) uM Adult (>18 years old) Not Specified Normal
Abnormal Concentrations
Biofluid Status Value Age Sex Condition Reference
Blood Detected and Quantified 1.2 (0.04-10.52) uM Adult (>18 years old) Both Biliary atresia
Blood Detected and Quantified 0.11 (0.044-0.74) uM Newborn (0-30 days old) Both Hepatitis
Cerebrospinal Fluid (CSF) Detected and Quantified 0.25 (0.037-0.46) uM Adult (>18 years old) Not Specified Comment Epilepsy
Associated Disorders and Diseases
Disease References
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 Link_out
      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 Link_out
          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 Link_out
              Associated OMIM IDs
              DrugBank ID Not Available
              DrugBank Metabolite ID Not Available
              Phenol Explorer Compound ID Not Available
              Phenol Explorer Metabolite ID Not Available
              FoodDB ID FDB022824
              KNApSAcK ID Not Available
              Chemspider ID Not Available
              KEGG Compound ID C00518 Link_out
              BioCyc ID Not Available
              BiGG ID 35227 Link_out
              Wikipedia Link Hyaluronic acid Link_out
              NuGOwiki Link HMDB02061 Link_out
              Metagene Link HMDB02061 Link_out
              METLIN ID Not Available
              PubChem Compound 53477741 Link_out
              PDB ID Not Available
              ChEBI ID Not Available
              References
              Synthesis Reference Tan, 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 Link_out
              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 Link_out

              Enzymes
              Name: UDP-glucuronosyltransferase 2B4
              Reactions: Not Available
              Gene Name: UGT2B4
              Uniprot ID: P06133 Link_out
              Protein Sequence: FASTA
              Gene Sequence: FASTA
              Name: UDP-glucuronosyltransferase 1-4
              Reactions: Not Available
              Gene Name: UGT1A4
              Uniprot ID: P22310 Link_out
              Protein Sequence: FASTA
              Gene Sequence: FASTA
              Name: UDP-glucuronosyltransferase 2B7
              Reactions: Not Available
              Gene Name: UGT2B7
              Uniprot ID: P16662 Link_out
              Protein Sequence: FASTA
              Gene Sequence: FASTA
              Name: UDP-glucuronosyltransferase 1-1
              Reactions: Not Available
              Gene Name: UGT1A1
              Uniprot ID: P22309 Link_out
              Protein Sequence: FASTA
              Gene Sequence: FASTA
              Name: UDP-glucuronosyltransferase 1-9
              Reactions: Not Available
              Gene Name: UGT1A9
              Uniprot ID: O60656 Link_out
              Protein Sequence: FASTA
              Gene Sequence: FASTA
              Name: UDP-glucuronosyltransferase 1-6
              Reactions: Not Available
              Gene Name: UGT1A6
              Uniprot ID: P19224 Link_out
              Protein Sequence: FASTA
              Gene Sequence: FASTA
              Name: Hyaluronan synthase 1
              Reactions: Not Available
              Gene Name: HAS1
              Uniprot ID: Q92839 Link_out
              Protein Sequence: FASTA
              Gene Sequence: FASTA
              Name: Hyaluronan synthase 3
              Reactions: Not Available
              Gene Name: HAS3
              Uniprot ID: O00219 Link_out
              Protein Sequence: FASTA
              Gene Sequence: FASTA
              Name: CD44 antigen
              Reactions: Not Available
              Gene Name: CD44
              Uniprot ID: P16070 Link_out
              Protein Sequence: FASTA
              Gene Sequence: FASTA
              Name: Hyaluronan synthase 2
              Reactions: Not Available
              Gene Name: HAS2
              Uniprot ID: Q92819 Link_out
              Protein Sequence: FASTA
              Gene Sequence: FASTA
              Name: Aggrecan core protein
              Reactions: Not Available
              Gene Name: ACAN
              Uniprot ID: P16112 Link_out
              Protein Sequence: FASTA
              Gene Sequence: FASTA
              Name: Tumor necrosis factor-inducible gene 6 protein
              Reactions: Not Available
              Gene Name: TNFAIP6
              Uniprot ID: P98066 Link_out
              Protein Sequence: FASTA
              Gene Sequence: FASTA
              Name: Neurocan core protein
              Reactions: Not Available
              Gene Name: NCAN
              Uniprot ID: O14594 Link_out
              Protein Sequence: FASTA
              Gene Sequence: FASTA
              Name: Brevican core protein
              Reactions: Not Available
              Gene Name: BCAN
              Uniprot ID: Q96GW7 Link_out
              Protein Sequence: FASTA
              Gene Sequence: FASTA
              Name: Versican core protein
              Reactions: Not Available
              Gene Name: VCAN
              Uniprot ID: P13611 Link_out
              Protein Sequence: FASTA
              Gene Sequence: FASTA
              Name: Hyaluronan mediated motility receptor
              Reactions: Not Available
              Gene Name: HMMR
              Uniprot ID: O75330 Link_out
              Protein Sequence: FASTA
              Gene Sequence: FASTA
              Name: Stabilin-2
              Reactions: Not Available
              Gene Name: STAB2
              Uniprot ID: Q8WWQ8 Link_out
              Protein Sequence: FASTA
              Gene Sequence: FASTA
              Name: Lymphatic vessel endothelial hyaluronic acid receptor 1
              Reactions: Not Available
              Gene Name: LYVE1
              Uniprot ID: Q9Y5Y7 Link_out
              Protein Sequence: FASTA
              Gene Sequence: FASTA
              Name: Hyaluronan and proteoglycan link protein 1
              Reactions: Not Available
              Gene Name: HAPLN1
              Uniprot ID: P10915 Link_out
              Protein Sequence: FASTA
              Gene Sequence: FASTA
              Name: Hyaluronan and proteoglycan link protein 2
              Reactions: Not Available
              Gene Name: HAPLN2
              Uniprot ID: Q9GZV7 Link_out
              Protein Sequence: FASTA
              Gene Sequence: FASTA
              Name: Hyaluronan and proteoglycan link protein 3
              Reactions: Not Available
              Gene Name: HAPLN3
              Uniprot ID: Q96S86 Link_out
              Protein Sequence: FASTA
              Gene Sequence: FASTA
              Name: Hyaluronan and proteoglycan link protein 4
              Reactions: Not Available
              Gene Name: HAPLN4
              Uniprot ID: Q86UW8 Link_out
              Protein Sequence: FASTA
              Gene Sequence: FASTA
              Name: Stabilin-1
              Reactions: Not Available
              Gene Name: STAB1
              Uniprot ID: Q9NY15 Link_out
              Protein Sequence: FASTA
              Gene Sequence: FASTA
              Name: Layilin
              Reactions: Not Available
              Gene Name: LAYN
              Uniprot ID: Q6UX15 Link_out
              Protein Sequence: FASTA
              Gene Sequence: FASTA
              Name: Sushi domain-containing protein 5
              Reactions: Not Available
              Gene Name: SUSD5
              Uniprot ID: O60279 Link_out
              Protein Sequence: FASTA
              Gene Sequence: FASTA