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Human Metabolome Database Version 3.5

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Showing metabocard for Hyaluronic acid (HMDB02061)

Record Information
Version 3.5
Creation Date 2006-05-22 08:17:34 -0600
Update Date 2013-02-08 17:11:19 -0700
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 | 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 Comments
Cerebrospinal Fluid (CSF) Detected and Quantified
Article_icon
0.24 (0.12-0.36) uM Adult (>18 years old) Not Specified Normal Not Available
Abnormal Concentrations
Biofluid Status Value Age Sex Condition Comments
Blood Detected and Quantified
Article_icon
1.2 (0.04-10.52) uM Adult (>18 years old) Both Biliary atresia Not Available
Blood Detected and Quantified
Article_icon
0.11 (0.044-0.74) uM Newborn (0-30 days old) Both Hepatitis Not Available
Cerebrospinal Fluid (CSF) Detected and Quantified
Article_icon
0.25 (0.037-0.46) uM Adult (>18 years old) Not Specified Epilepsy Temporal lobe 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
        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
        Enzymes
        Name: Hyaluronan synthase 1
        Reactions:
        • (1) UDP-alpha-N-acetyl-D-glucosamine + beta-D-glucuronosyl-(1->3)-N-acetyl-beta-D-glucosaminyl-(1->4)- [nascent hyaluronan] = UDP + N-acetyl-beta-D-glucosaminyl-(1->4)-beta-D-glucuronosyl-(1->3)-N- acetyl-beta-D-glucosaminyl-(1->4)-[nascent hyaluronan] [RN:R05327 R06068]
        • (2) UDP-alpha-D-glucuronate + N-acetyl-beta-D-glucosaminyl-(1->4)-beta-D-glucuronosyl-(1->3)- [nascent hyaluronan] = UDP + beta-D-glucuronosyl-(1->3)-N-acetyl-beta-D-glucosaminyl-(1->4)-beta- D-glucuronosyl-(1->3)-[nascent hyaluronan]
        Gene Name: HAS1
        Uniprot ID: Q92839 Link_out
        Protein Sequence: FASTA
        Gene Sequence: FASTA
        Name: Hyaluronan synthase 3
        Reactions:
        • (1) UDP-alpha-N-acetyl-D-glucosamine + beta-D-glucuronosyl-(1->3)-N-acetyl-beta-D-glucosaminyl-(1->4)- [nascent hyaluronan] = UDP + N-acetyl-beta-D-glucosaminyl-(1->4)-beta-D-glucuronosyl-(1->3)-N- acetyl-beta-D-glucosaminyl-(1->4)-[nascent hyaluronan] [RN:R05327 R06068]
        • (2) UDP-alpha-D-glucuronate + N-acetyl-beta-D-glucosaminyl-(1->4)-beta-D-glucuronosyl-(1->3)- [nascent hyaluronan] = UDP + beta-D-glucuronosyl-(1->3)-N-acetyl-beta-D-glucosaminyl-(1->4)-beta- D-glucuronosyl-(1->3)-[nascent hyaluronan]
        Gene Name: HAS3
        Uniprot ID: O00219 Link_out
        Protein Sequence: FASTA
        Gene Sequence: FASTA
        Name: CD44 antigen
        Reactions:
          Gene Name: CD44
          Uniprot ID: P16070 Link_out
          Protein Sequence: FASTA
          Gene Sequence: FASTA
          Name: Hyaluronan synthase 2
          Reactions:
          • (1) UDP-alpha-N-acetyl-D-glucosamine + beta-D-glucuronosyl-(1->3)-N-acetyl-beta-D-glucosaminyl-(1->4)- [nascent hyaluronan] = UDP + N-acetyl-beta-D-glucosaminyl-(1->4)-beta-D-glucuronosyl-(1->3)-N- acetyl-beta-D-glucosaminyl-(1->4)-[nascent hyaluronan] [RN:R05327 R06068]
          • (2) UDP-alpha-D-glucuronate + N-acetyl-beta-D-glucosaminyl-(1->4)-beta-D-glucuronosyl-(1->3)- [nascent hyaluronan] = UDP + beta-D-glucuronosyl-(1->3)-N-acetyl-beta-D-glucosaminyl-(1->4)-beta- D-glucuronosyl-(1->3)-[nascent hyaluronan]
          Gene Name: HAS2
          Uniprot ID: Q92819 Link_out
          Protein Sequence: FASTA
          Gene Sequence: FASTA
          Name: Aggrecan core protein
          Reactions:
            Gene Name: ACAN
            Uniprot ID: P16112 Link_out
            Protein Sequence: FASTA
            Gene Sequence: FASTA
            Name: Tumor necrosis factor-inducible gene 6 protein
            Reactions:
              Gene Name: TNFAIP6
              Uniprot ID: P98066 Link_out
              Protein Sequence: FASTA
              Gene Sequence: FASTA
              Name: Neurocan core protein
              Reactions:
                Gene Name: NCAN
                Uniprot ID: O14594 Link_out
                Protein Sequence: FASTA
                Gene Sequence: FASTA
                Name: Brevican core protein
                Reactions:
                  Gene Name: BCAN
                  Uniprot ID: Q96GW7 Link_out
                  Protein Sequence: FASTA
                  Gene Sequence: FASTA
                  Name: Versican core protein
                  Reactions:
                    Gene Name: VCAN
                    Uniprot ID: P13611 Link_out
                    Protein Sequence: FASTA
                    Gene Sequence: FASTA
                    Name: Hyaluronan mediated motility receptor
                    Reactions:
                      Gene Name: HMMR
                      Uniprot ID: O75330 Link_out
                      Protein Sequence: FASTA
                      Gene Sequence: FASTA
                      Name: Stabilin-2
                      Reactions:
                        Gene Name: STAB2
                        Uniprot ID: Q8WWQ8 Link_out
                        Protein Sequence: FASTA
                        Gene Sequence: FASTA
                        Name: Lymphatic vessel endothelial hyaluronic acid receptor 1
                        Reactions:
                          Gene Name: LYVE1
                          Uniprot ID: Q9Y5Y7 Link_out
                          Protein Sequence: FASTA
                          Gene Sequence: FASTA
                          Name: Hyaluronan and proteoglycan link protein 1
                          Reactions:
                            Gene Name: HAPLN1
                            Uniprot ID: P10915 Link_out
                            Protein Sequence: FASTA
                            Gene Sequence: FASTA
                            Name: Hyaluronan and proteoglycan link protein 2
                            Reactions:
                              Gene Name: HAPLN2
                              Uniprot ID: Q9GZV7 Link_out
                              Protein Sequence: FASTA
                              Gene Sequence: FASTA
                              Name: Hyaluronan and proteoglycan link protein 3
                              Reactions:
                                Gene Name: HAPLN3
                                Uniprot ID: Q96S86 Link_out
                                Protein Sequence: FASTA
                                Gene Sequence: FASTA
                                Name: Hyaluronan and proteoglycan link protein 4
                                Reactions:
                                  Gene Name: HAPLN4
                                  Uniprot ID: Q86UW8 Link_out
                                  Protein Sequence: FASTA
                                  Gene Sequence: FASTA
                                  Name: Stabilin-1
                                  Reactions:
                                    Gene Name: STAB1
                                    Uniprot ID: Q9NY15 Link_out
                                    Protein Sequence: FASTA
                                    Gene Sequence: FASTA
                                    Name: Layilin
                                    Reactions:
                                      Gene Name: LAYN
                                      Uniprot ID: Q6UX15 Link_out
                                      Protein Sequence: FASTA
                                      Gene Sequence: FASTA
                                      Name: Sushi domain-containing protein 5
                                      Reactions:
                                        Gene Name: SUSD5
                                        Uniprot ID: O60279 Link_out
                                        Protein Sequence: FASTA
                                        Gene Sequence: FASTA