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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (28) Show 28 proteins XML

Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2006-05-22 14:17:34 UTC

Update Date

2021-10-13 04:37:16 UTC

HMDB ID

HMDB0002061

Secondary Accession Numbers

HMDB0006554
HMDB0010366
HMDB02061
HMDB06554
HMDB10366

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 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

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI


  Mrv1652304061819212D          
 
 28 29  0  0  1  0            999 V2000
    8.7450   -8.9100    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.7450   -9.7350    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    9.4594  -10.1475    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.1740   -9.7350    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   10.1740   -8.9100    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    9.4594   -8.4975    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.0305   -8.4975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8994   -8.4910    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.4594  -10.9724    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9697  -11.9337    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0305  -10.1475    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.8994  -10.1540    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.3261   -8.9043    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.6139   -8.0785    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   12.3451   -8.5007    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   13.0596   -8.0884    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   13.0597   -7.2634    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   12.3285   -6.8411    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.6140   -7.2535    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   12.3449   -9.3224    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.9163   -6.8505    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2143   -7.2557    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.9164   -6.0226    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.3907   -6.4857    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.7849   -8.5074    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.8994  -10.9790    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1808  -11.3940    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.6040  -11.3858    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  1  6  1  0  0  0  0
  1  7  1  1  0  0  0
  5  8  1  1  0  0  0
  3  9  1  1  0  0  0
  9 10  1  0  0  0  0
  2 11  1  6  0  0  0
  4 12  1  6  0  0  0
  7 13  1  0  0  0  0
 14  8  1  6  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 14 19  1  0  0  0  0
 15 20  1  1  0  0  0
 19 21  1  1  0  0  0
 21 22  1  0  0  0  0
 21 23  2  0  0  0  0
 17 24  1  1  0  0  0
 16 25  1  6  0  0  0
 12 26  1  0  0  0  0
 26 27  2  0  0  0  0
 26 28  1  0  0  0  0
M  STY  1   1 SRU
M  SCN  1   1 HT 
M  SAL   1 15   9   3   4  12  26  28  27   5   8  14  19  21  23  22  18
M  SAL   1 11  15  20  16  25   6   1   7  13   2  11  17
M  SDI   1  4   13.3580   -6.5158   13.8575   -7.3705
M  SDI   1  4    9.0675  -11.8123    8.5326  -10.9793
M  SBL   1  2  10  25
M  SMT   1 n
M  END

HMDB0002061
     RDKit          3D
Hyaluronic acid
 50 51  0  0  0  0  0  0  0  0999 V2000
    3.7553    3.1806   -2.1512 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4900    2.7352   -1.5218 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4633    3.4100   -1.7053 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4832    1.5681   -0.7379 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2923    1.1135   -0.1217 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8202   -0.2462   -0.6551 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4568   -0.3834   -0.1568 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4494   -0.3408   -1.1159 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.4847    0.7447   -0.7906 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.7375    1.6064   -1.9745 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8925    1.7523   -2.4501 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7051    2.2871   -2.6050 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6793    0.2086   -0.3886 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5770   -0.6111    0.7267 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.8723   -0.9700    1.0976 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8535   -1.8645    0.3020 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.9384   -2.2426    1.2937 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1775   -1.6669   -1.0358 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.1178   -1.8074   -2.0462 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6781   -1.2665   -0.3598 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2630   -1.2455    0.8771 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3789   -2.6588    1.4677 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9933   -2.4736    2.7273 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4369   -0.4492    1.8333 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0286   -0.5402    3.1018 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3725    0.9903    1.3697 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2306    1.5406    1.9749 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2841    3.9217   -1.5117 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4751    2.3309   -2.2937 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5909    3.6598   -3.1460 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3630    1.0456   -0.6180 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4250    1.8012   -0.3557 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8260   -0.1222   -1.7714 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0876   -0.2047   -2.1342 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0281    1.3741    0.0289 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7213    2.3525   -3.6075 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0981   -0.1091    1.5919 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4932   -0.2017    1.0976 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5516   -2.7313    0.1759 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8854   -1.5562    2.0007 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4303   -2.4876   -1.1416 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8353   -2.4104   -1.7171 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3108   -0.8846    0.8031 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0461   -3.2923    0.8844 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3875   -3.0730    1.6752 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7459   -3.1012    2.8572 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4471   -0.9225    1.9266 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3051   -0.3582    3.7559 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2291    1.5697    1.7809 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0493    1.0285    2.7632 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
  9 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  1  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
  6 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 21 24  1  0
 24 25  1  0
 24 26  1  0
 26 27  1  0
 26  5  1  0
 18  8  1  0
  1 28  1  0
  1 29  1  0
  1 30  1  0
  4 31  1  0
  5 32  1  1
  6 33  1  6
  8 34  1  6
  9 35  1  1
 12 36  1  0
 14 37  1  1
 15 38  1  0
 16 39  1  6
 17 40  1  0
 18 41  1  6
 19 42  1  0
 21 43  1  6
 22 44  1  0
 22 45  1  0
 23 46  1  0
 24 47  1  1
 25 48  1  0
 26 49  1  1
 27 50  1  0
M  END


  Mrv1652304061819212D          
 
 28 29  0  0  1  0            999 V2000
    8.7450   -8.9100    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.7450   -9.7350    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    9.4594  -10.1475    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.1740   -9.7350    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   10.1740   -8.9100    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    9.4594   -8.4975    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.0305   -8.4975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8994   -8.4910    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.4594  -10.9724    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9697  -11.9337    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0305  -10.1475    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.8994  -10.1540    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.3261   -8.9043    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.6139   -8.0785    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   12.3451   -8.5007    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   13.0596   -8.0884    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   13.0597   -7.2634    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   12.3285   -6.8411    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.6140   -7.2535    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   12.3449   -9.3224    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.9163   -6.8505    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2143   -7.2557    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.9164   -6.0226    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.3907   -6.4857    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.7849   -8.5074    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.8994  -10.9790    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1808  -11.3940    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.6040  -11.3858    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  1  6  1  0  0  0  0
  1  7  1  1  0  0  0
  5  8  1  1  0  0  0
  3  9  1  1  0  0  0
  9 10  1  0  0  0  0
  2 11  1  6  0  0  0
  4 12  1  6  0  0  0
  7 13  1  0  0  0  0
 14  8  1  6  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 14 19  1  0  0  0  0
 15 20  1  1  0  0  0
 19 21  1  1  0  0  0
 21 22  1  0  0  0  0
 21 23  2  0  0  0  0
 17 24  1  1  0  0  0
 16 25  1  6  0  0  0
 12 26  1  0  0  0  0
 26 27  2  0  0  0  0
 26 28  1  0  0  0  0
M  STY  1   1 SRU
M  SCN  1   1 HT 
M  SAL   1 15   9   3   4  12  26  28  27   5   8  14  19  21  23  22  18
M  SAL   1 11  15  20  16  25   6   1   7  13   2  11  17
M  SDI   1  4   13.3580   -6.5158   13.8575   -7.3705
M  SDI   1  4    9.0675  -11.8123    8.5326  -10.9793
M  SBL   1  2  10  25
M  SMT   1 n
M  END
> <DATABASE_ID>
HMDB0002061

> <DATABASE_NAME>
hmdb

> <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_KEY>
LJKKEBYAXYCTNF-GIXQJHCPSA-N

> <FORMULA>
(C14H21NO11)nH2O

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <ALOGPS_LOGP>
-2.57

> <ALOGPS_LOGS>
-0.53

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.16e+02 g/l

$$$$

HMDB0002061
     RDKit          3D
Hyaluronic acid
 50 51  0  0  0  0  0  0  0  0999 V2000
    3.7553    3.1806   -2.1512 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4900    2.7352   -1.5218 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4633    3.4100   -1.7053 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4832    1.5681   -0.7379 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2923    1.1135   -0.1217 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8202   -0.2462   -0.6551 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4568   -0.3834   -0.1568 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4494   -0.3408   -1.1159 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.4847    0.7447   -0.7906 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.7375    1.6064   -1.9745 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8925    1.7523   -2.4501 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7051    2.2871   -2.6050 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6793    0.2086   -0.3886 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5770   -0.6111    0.7267 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.8723   -0.9700    1.0976 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8535   -1.8645    0.3020 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.9384   -2.2426    1.2937 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1775   -1.6669   -1.0358 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.1178   -1.8074   -2.0462 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6781   -1.2665   -0.3598 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2630   -1.2455    0.8771 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3789   -2.6588    1.4677 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9933   -2.4736    2.7273 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4369   -0.4492    1.8333 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0286   -0.5402    3.1018 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3725    0.9903    1.3697 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2306    1.5406    1.9749 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2841    3.9217   -1.5117 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4751    2.3309   -2.2937 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5909    3.6598   -3.1460 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3630    1.0456   -0.6180 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4250    1.8012   -0.3557 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8260   -0.1222   -1.7714 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0876   -0.2047   -2.1342 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0281    1.3741    0.0289 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7213    2.3525   -3.6075 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0981   -0.1091    1.5919 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4932   -0.2017    1.0976 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5516   -2.7313    0.1759 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8854   -1.5562    2.0007 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4303   -2.4876   -1.1416 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8353   -2.4104   -1.7171 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3108   -0.8846    0.8031 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0461   -3.2923    0.8844 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3875   -3.0730    1.6752 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7459   -3.1012    2.8572 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4471   -0.9225    1.9266 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3051   -0.3582    3.7559 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2291    1.5697    1.7809 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0493    1.0285    2.7632 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
  9 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  1  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
  6 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 21 24  1  0
 24 25  1  0
 24 26  1  0
 26 27  1  0
 26  5  1  0
 18  8  1  0
  1 28  1  0
  1 29  1  0
  1 30  1  0
  4 31  1  0
  5 32  1  1
  6 33  1  6
  8 34  1  6
  9 35  1  1
 12 36  1  0
 14 37  1  1
 15 38  1  0
 16 39  1  6
 17 40  1  0
 18 41  1  6
 19 42  1  0
 21 43  1  6
 22 44  1  0
 22 45  1  0
 23 46  1  0
 24 47  1  1
 25 48  1  0
 26 49  1  1
 27 50  1  0
M  END

HEADER    PROTEIN                                 06-APR-18   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-APR-18         0                                  
HETATM    1  C     n     1      16.324 -16.632   0.000  0.00  0.00           C+0
HETATM    2  C     n     1      16.324 -18.172   0.000  0.00  0.00           C+0
HETATM    3  C     n     1      17.658 -18.942   0.000  0.00  0.00           C+0
HETATM    4  C     n     1      18.991 -18.172   0.000  0.00  0.00           C+0
HETATM    5  C     n     1      18.991 -16.632   0.000  0.00  0.00           C+0
HETATM    6  O     n     1      17.658 -15.862   0.000  0.00  0.00           O+0
HETATM    7  C     n     1      14.990 -15.862   0.000  0.00  0.00           C+0
HETATM    8  O     n     1      20.346 -15.850   0.000  0.00  0.00           O+0
HETATM    9  O     n     1      17.658 -20.482   0.000  0.00  0.00           O+0
HETATM   10  H   UNK     0      14.877 -22.276   0.000  0.00  0.00           H+0
HETATM   11  O     n     1      14.990 -18.942   0.000  0.00  0.00           O+0
HETATM   12  N     n     1      20.346 -18.954   0.000  0.00  0.00           N+0
HETATM   13  O     n     1      13.675 -16.621   0.000  0.00  0.00           O+0
HETATM   14  C     n     1      21.679 -15.080   0.000  0.00  0.00           C+0
HETATM   15  C     n     1      23.044 -15.868   0.000  0.00  0.00           C+0
HETATM   16  C     n     1      24.378 -15.098   0.000  0.00  0.00           C+0
HETATM   17  C     n     1      24.378 -13.558   0.000  0.00  0.00           C+0
HETATM   18  O     n     1      23.013 -12.770   0.000  0.00  0.00           O+0
HETATM   19  C     n     1      21.679 -13.540   0.000  0.00  0.00           C+0
HETATM   20  O     n     1      23.044 -17.402   0.000  0.00  0.00           O+0
HETATM   21  C     n     1      20.377 -12.788   0.000  0.00  0.00           C+0
HETATM   22  O     n     1      19.067 -13.544   0.000  0.00  0.00           O+0
HETATM   23  O     n     1      20.377 -11.242   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0      26.863 -12.107   0.000  0.00  0.00           O+0
HETATM   25  O     n     1      25.732 -15.880   0.000  0.00  0.00           O+0
HETATM   26  C     n     1      20.346 -20.494   0.000  0.00  0.00           C+0
HETATM   27  O     n     1      19.004 -21.269   0.000  0.00  0.00           O+0
HETATM   28  C     n     1      21.661 -21.253   0.000  0.00  0.00           C+0
CONECT    1    2    6    7                                                  
CONECT    2    1    3   11                                                  
CONECT    3    2    4    9                                                  
CONECT    4    3    5   12                                                  
CONECT    5    4    6    8                                                  
CONECT    6    5    1                                                       
CONECT    7    1   13                                                       
CONECT    8    5   14                                                       
CONECT    9    3   10                                                       
CONECT   10    9                                                            
CONECT   11    2                                                            
CONECT   12    4   26                                                       
CONECT   13    7                                                            
CONECT   14    8   15   19                                                  
CONECT   15   14   16   20                                                  
CONECT   16   15   17   25                                                  
CONECT   17   16   18   24                                                  
CONECT   18   17   19                                                       
CONECT   19   18   14   21                                                  
CONECT   20   15                                                            
CONECT   21   19   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21                                                            
CONECT   24   17                                                            
CONECT   25   16                                                            
CONECT   26   12   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26                                                            
MASTER        0    0    0    0    0    0    0    0   28    0   58    0
END

COMPND    HMDB0002061
HETATM    1  C1  UNL     1       3.755   3.181  -2.151  1.00  0.00           C  
HETATM    2  C2  UNL     1       2.490   2.735  -1.522  1.00  0.00           C  
HETATM    3  O1  UNL     1       1.463   3.410  -1.705  1.00  0.00           O  
HETATM    4  N1  UNL     1       2.483   1.568  -0.738  1.00  0.00           N  
HETATM    5  C3  UNL     1       1.292   1.113  -0.122  1.00  0.00           C  
HETATM    6  C4  UNL     1       0.820  -0.246  -0.655  1.00  0.00           C  
HETATM    7  O2  UNL     1      -0.457  -0.383  -0.157  1.00  0.00           O  
HETATM    8  C5  UNL     1      -1.449  -0.341  -1.116  1.00  0.00           C  
HETATM    9  C6  UNL     1      -2.485   0.745  -0.791  1.00  0.00           C  
HETATM   10  C7  UNL     1      -2.737   1.606  -1.975  1.00  0.00           C  
HETATM   11  O3  UNL     1      -3.892   1.752  -2.450  1.00  0.00           O  
HETATM   12  O4  UNL     1      -1.705   2.287  -2.605  1.00  0.00           O  
HETATM   13  O5  UNL     1      -3.679   0.209  -0.389  1.00  0.00           O  
HETATM   14  C8  UNL     1      -3.577  -0.611   0.727  1.00  0.00           C  
HETATM   15  O6  UNL     1      -4.872  -0.970   1.098  1.00  0.00           O  
HETATM   16  C9  UNL     1      -2.853  -1.864   0.302  1.00  0.00           C  
HETATM   17  O7  UNL     1      -1.938  -2.243   1.294  1.00  0.00           O  
HETATM   18  C10 UNL     1      -2.177  -1.667  -1.036  1.00  0.00           C  
HETATM   19  O8  UNL     1      -3.118  -1.807  -2.046  1.00  0.00           O  
HETATM   20  O9  UNL     1       1.678  -1.267  -0.360  1.00  0.00           O  
HETATM   21  C11 UNL     1       2.263  -1.246   0.877  1.00  0.00           C  
HETATM   22  C12 UNL     1       2.379  -2.659   1.468  1.00  0.00           C  
HETATM   23  O10 UNL     1       2.993  -2.474   2.727  1.00  0.00           O  
HETATM   24  C13 UNL     1       1.437  -0.449   1.833  1.00  0.00           C  
HETATM   25  O11 UNL     1       2.029  -0.540   3.102  1.00  0.00           O  
HETATM   26  C14 UNL     1       1.373   0.990   1.370  1.00  0.00           C  
HETATM   27  O12 UNL     1       0.231   1.541   1.975  1.00  0.00           O  
HETATM   28  H1  UNL     1       4.284   3.922  -1.512  1.00  0.00           H  
HETATM   29  H2  UNL     1       4.475   2.331  -2.294  1.00  0.00           H  
HETATM   30  H3  UNL     1       3.591   3.660  -3.146  1.00  0.00           H  
HETATM   31  H4  UNL     1       3.363   1.046  -0.618  1.00  0.00           H  
HETATM   32  H5  UNL     1       0.425   1.801  -0.356  1.00  0.00           H  
HETATM   33  H6  UNL     1       0.826  -0.122  -1.771  1.00  0.00           H  
HETATM   34  H7  UNL     1      -1.088  -0.205  -2.134  1.00  0.00           H  
HETATM   35  H8  UNL     1      -2.028   1.374   0.029  1.00  0.00           H  
HETATM   36  H9  UNL     1      -1.721   2.352  -3.608  1.00  0.00           H  
HETATM   37  H10 UNL     1      -3.098  -0.109   1.592  1.00  0.00           H  
HETATM   38  H11 UNL     1      -5.493  -0.202   1.098  1.00  0.00           H  
HETATM   39  H12 UNL     1      -3.552  -2.731   0.176  1.00  0.00           H  
HETATM   40  H13 UNL     1      -1.885  -1.556   2.001  1.00  0.00           H  
HETATM   41  H14 UNL     1      -1.430  -2.488  -1.142  1.00  0.00           H  
HETATM   42  H15 UNL     1      -3.835  -2.410  -1.717  1.00  0.00           H  
HETATM   43  H16 UNL     1       3.311  -0.885   0.803  1.00  0.00           H  
HETATM   44  H17 UNL     1       3.046  -3.292   0.884  1.00  0.00           H  
HETATM   45  H18 UNL     1       1.387  -3.073   1.675  1.00  0.00           H  
HETATM   46  H19 UNL     1       3.746  -3.101   2.857  1.00  0.00           H  
HETATM   47  H20 UNL     1       0.447  -0.923   1.927  1.00  0.00           H  
HETATM   48  H21 UNL     1       1.305  -0.358   3.756  1.00  0.00           H  
HETATM   49  H22 UNL     1       2.229   1.570   1.781  1.00  0.00           H  
HETATM   50  H23 UNL     1      -0.049   1.029   2.763  1.00  0.00           H  
CONECT    1    2   28   29   30
CONECT    2    3    3    4
CONECT    4    5   31
CONECT    5    6   26   32
CONECT    6    7   20   33
CONECT    7    8
CONECT    8    9   18   34
CONECT    9   10   13   35
CONECT   10   11   11   12
CONECT   12   36
CONECT   13   14
CONECT   14   15   16   37
CONECT   15   38
CONECT   16   17   18   39
CONECT   17   40
CONECT   18   19   41
CONECT   19   42
CONECT   20   21
CONECT   21   22   24   43
CONECT   22   23   44   45
CONECT   23   46
CONECT   24   25   26   47
CONECT   25   48
CONECT   26   27   49
CONECT   27   50
END

HMDB0002061
     RDKit          3D
Hyaluronic acid
 50 51  0  0  0  0  0  0  0  0999 V2000
    3.7553    3.1806   -2.1512 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4900    2.7352   -1.5218 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4633    3.4100   -1.7053 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4832    1.5681   -0.7379 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2923    1.1135   -0.1217 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8202   -0.2462   -0.6551 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4568   -0.3834   -0.1568 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4494   -0.3408   -1.1159 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.4847    0.7447   -0.7906 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.7375    1.6064   -1.9745 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8925    1.7523   -2.4501 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7051    2.2871   -2.6050 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6793    0.2086   -0.3886 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5770   -0.6111    0.7267 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.8723   -0.9700    1.0976 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8535   -1.8645    0.3020 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.9384   -2.2426    1.2937 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1775   -1.6669   -1.0358 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.1178   -1.8074   -2.0462 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6781   -1.2665   -0.3598 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2630   -1.2455    0.8771 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3789   -2.6588    1.4677 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9933   -2.4736    2.7273 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4369   -0.4492    1.8333 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0286   -0.5402    3.1018 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3725    0.9903    1.3697 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2306    1.5406    1.9749 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2841    3.9217   -1.5117 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4751    2.3309   -2.2937 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5909    3.6598   -3.1460 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3630    1.0456   -0.6180 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4250    1.8012   -0.3557 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8260   -0.1222   -1.7714 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0876   -0.2047   -2.1342 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0281    1.3741    0.0289 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7213    2.3525   -3.6075 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0981   -0.1091    1.5919 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4932   -0.2017    1.0976 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5516   -2.7313    0.1759 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8854   -1.5562    2.0007 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4303   -2.4876   -1.1416 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8353   -2.4104   -1.7171 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3108   -0.8846    0.8031 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0461   -3.2923    0.8844 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3875   -3.0730    1.6752 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7459   -3.1012    2.8572 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4471   -0.9225    1.9266 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3051   -0.3582    3.7559 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2291    1.5697    1.7809 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0493    1.0285    2.7632 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
  9 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  1  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
  6 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 21 24  1  0
 24 25  1  0
 24 26  1  0
 26 27  1  0
 26  5  1  0
 18  8  1  0
  1 28  1  0
  1 29  1  0
  1 30  1  0
  4 31  1  0
  5 32  1  1
  6 33  1  6
  8 34  1  6
  9 35  1  1
 12 36  1  0
 14 37  1  1
 15 38  1  0
 16 39  1  6
 17 40  1  0
 18 41  1  6
 19 42  1  0
 21 43  1  6
 22 44  1  0
 22 45  1  0
 23 46  1  0
 24 47  1  1
 25 48  1  0
 26 49  1  1
 27 50  1  0
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
(2S,3S,4R,5R,6R)-3-[(2S,3R,4R,5S,6R)-3-Acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4,5,6-trihydroxyoxane-2-carboxylic acid	ChEBI
2-Acetamido-2-deoxy-beta-D-gluco-hexopyranosyl-(1->4)-beta-D-gluco-hexopyranuronic acid	ChEBI
WURCS=2.0/2,2,1/[a2122a-1b_1-5][a2122h-1b_1-5_2*ncc/3=o]/1-2/a4-b1	ChEBI
(2S,3S,4R,5R,6R)-3-[(2S,3R,4R,5S,6R)-3-Acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4,5,6-trihydroxyoxane-2-carboxylate	Generator
2-Acetamido-2-deoxy-b-D-gluco-hexopyranosyl-(1->4)-b-D-gluco-hexopyranuronate	Generator
2-Acetamido-2-deoxy-b-D-gluco-hexopyranosyl-(1->4)-b-D-gluco-hexopyranuronic acid	Generator
2-Acetamido-2-deoxy-beta-D-gluco-hexopyranosyl-(1->4)-beta-D-gluco-hexopyranuronate	Generator
2-Acetamido-2-deoxy-β-D-gluco-hexopyranosyl-(1->4)-β-D-gluco-hexopyranuronate	Generator
2-Acetamido-2-deoxy-β-D-gluco-hexopyranosyl-(1->4)-β-D-gluco-hexopyranuronic acid	Generator
Hyaluronate	Generator
Hyaluronan	HMDB
(2S,3S,4R,5R,6R)-3-{[(2S,3R,4R,5S,6R)-4,5-dihydroxy-3-[(1-hydroxyethylidene)amino]-6-(hydroxymethyl)oxan-2-yl]oxy}-4,5,6-trihydroxyoxane-2-carboxylate	HMDB

Chemical Formula

(C₁₄H₂₁NO₁₁)nH₂O

Average Molecular Weight

Not Available

Monoisotopic Molecular Weight

Not Available

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

9004-61-9

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 Key

LJKKEBYAXYCTNF-GIXQJHCPSA-N

Chemical Taxonomy

Description

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.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

N-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 Framework

Aliphatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 17875085)
Cerebrospinal Fluid (CSF) (PMID: 12121313)

Cellular substructure

Extracellular (HMDB: HMDB0002061)

Organelle

Lysosome (HMDB: HMDB0002061)

Source

Endogenous

Endogenous (HMDB: HMDB0002061)

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Process

Not Available

Role

Industrial application

Pharmaceutical industry

Biomarker

Diabetes mellitus type 2 (MarkerDB: MDB00000372)
Epilepsy (MarkerDB: MDB00000372)
Meningitis (MarkerDB: MDB00000372)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	1274.00 to 1275.00 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	827100 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	-6.623 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	95.1 g/L	ALOGPS
logP	-2.6	ALOGPS
logS	-0.53	ALOGPS
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	190.853	30932474
DeepCCS	[M-H]-	188.989	30932474
DeepCCS	[M-2H]-	222.369	30932474
DeepCCS	[M+Na]+	196.486	30932474

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	1.65 minutes	32390414
Predicted by Siyang on May 30, 2022	11.0314 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	8.98 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	358.2 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	798.9 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	242.5 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	33.1 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	176.3 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	83.9 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	311.7 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	277.1 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	826.3 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	591.2 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	80.5 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	949.7 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	228.8 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	291.4 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	580.1 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	393.7 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	471.7 seconds	40023050

Predicted Kovats Retention Indices

Not Available

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Hyaluronic acid GC-MS (TMS_2_11) - 70eV, Positive	Not Available	2022-08-08	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	Not Available	2022-08-06	Not Available	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hyaluronic acid 10V, Positive-QTOF	splash10-001j-0109000000-aa608ebc95d3c41aa119	2019-02-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hyaluronic acid 20V, Positive-QTOF	splash10-004j-1904000000-f499cfd0131b9f9a2980	2019-02-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hyaluronic acid 40V, Positive-QTOF	splash10-01rm-5913000000-b22d6d78477b0b69bd4e	2019-02-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hyaluronic acid 10V, Negative-QTOF	splash10-0kdv-3359000000-4a1c55483243aa363f3b	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hyaluronic acid 20V, Negative-QTOF	splash10-0059-4898000000-c9c9f151634e6af628e3	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hyaluronic acid 40V, Negative-QTOF	splash10-05gi-8890000000-0e073a162fbb99c31d01	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hyaluronic acid 10V, Positive-QTOF	splash10-0002-0009000000-723f981753eca3762215	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hyaluronic acid 20V, Positive-QTOF	splash10-0012-0329000000-91a530fe4b8b4d73a0dc	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hyaluronic acid 40V, Positive-QTOF	splash10-0a4u-9410000000-0d005698920dfdb4eeff	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hyaluronic acid 10V, Negative-QTOF	splash10-0002-1009000000-559b8fad12108c65816f	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hyaluronic acid 20V, Negative-QTOF	splash10-0adi-3339000000-76adaf82a127143d0f78	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hyaluronic acid 40V, Negative-QTOF	splash10-052f-9523000000-abd6e76516deb9312be0	2021-09-25	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Lysosome

Biospecimen Locations

Blood
Cerebrospinal Fluid (CSF)

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.053 +/- 0.015 uM	Adult (>18 years old)	Both	Normal	16966827	details
Blood	Detected and Quantified	<0.00496 uM	Adult (>18 years old)	Both	Normal	12675874	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.24 (0.12-0.36) uM	Adult (>18 years old)	Not Specified	Normal	12121313	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.0644 +/- 0.0528 uM	Not Specified	Not Specified	Normal	8899053	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.214 +/- 0.0992 uM	Not Specified	Not Specified	Normal	8899053	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	1.2 (0.04-10.52) uM	Adult (>18 years old)	Both	Biliary atresia	17875085	details
Blood	Detected and Quantified	0.11 (0.044-0.74) uM	Newborn (0-30 days old)	Both	Hepatitis	17875085	details
Blood	Detected and Quantified	0.11 +/- 0.013 uM	Adult (>18 years old)	Both	Diabetes	16966827	details
Blood	Detected and Quantified	0.00860 +/- 0.0103 uM	Adult (>18 years old)	Both	Uremia	12675874	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.25 (0.037-0.46) uM	Adult (>18 years old)	Not Specified	Epilepsy	12121313	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	>10.306 uM	Not Specified	Not Specified	Meningitis	8899053	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	>5.153 uM	Not Specified	Not Specified	Colon carcinoma	8899053	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.0593-0.995 uM	Not Specified	Not Specified	Head injury	7992658	details

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 ]
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 ]
Diabetes mellitus type 2
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 ]
Uremia
Vanholder R, De Smet R, Glorieux G, Argiles A, Baurmeister U, Brunet P, Clark W, Cohen G, De Deyn PP, Deppisch R, Descamps-Latscha B, Henle T, Jorres A, Lemke HD, Massy ZA, Passlick-Deetjen J, Rodriguez M, Stegmayr B, Stenvinkel P, Tetta C, Wanner C, Zidek W: Review on uremic toxins: classification, concentration, and interindividual variability. Kidney Int. 2003 May;63(5):1934-43. doi: 10.1046/j.1523-1755.2003.00924.x. [PubMed:12675874 ]
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 ]
Meningitis
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 ]
Head injury
Burke EJ, Mehlhorn U, Allen SJ: Hyaluronan in cerebrospinal fluid after head injury. Acta Neurol (Napoli). 1994 Jun;16(3):103-9. [PubMed:7992658 ]

Associated OMIM IDs

210500 (Biliary atresia)
125853 (Diabetes mellitus type 2)

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022824

KNApSAcK ID

Not Available

Chemspider ID

8020685

KEGG Compound ID

C00518

BioCyc ID

Not Available

BiGG ID

35227

Wikipedia Link

Hyaluronic acid

METLIN ID

Not Available

PubChem Compound

9844971

PDB ID

Not Available

ChEBI ID

150712

Food Biomarker Ontology

Not Available

VMH ID

MarkerDB ID

MDB00000372

Good Scents ID

rw1067861

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

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 ]
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.

Show all enzymes and transporters

Enzymes

Enzyme Details

1. UDP-glucuronosyltransferase 2B4

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

Enzyme Details

2. UDP-glucuronosyltransferase 1-4

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

Enzyme Details

3. UDP-glucuronosyltransferase 2B7

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

Enzyme Details

4. UDP-glucuronosyltransferase 1-1

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

Enzyme Details

5. UDP-glucuronosyltransferase 1-9

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

Enzyme Details

6. UDP-glucuronosyltransferase 1-6

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

Enzyme Details

7. Hyaluronan synthase 1

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

Enzyme Details

8. Hyaluronan synthase 3

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

Enzyme Details

9. CD44 antigen

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

Enzyme Details

10. Hyaluronan synthase 2

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.

Show all enzymes and transporters

Showing metabocard for Hyaluronic acid (HMDB0002061)

MOL for HMDB0002061 (Hyaluronic acid)

3D MOL for HMDB0002061 (Hyaluronic acid)

3D SDF for HMDB0002061 (Hyaluronic acid)

3D-SDF for HMDB0002061 (Hyaluronic acid)

PDB for HMDB0002061 (Hyaluronic acid)

3D PDB for HMDB0002061 (Hyaluronic acid)

SMILES for HMDB0002061 (Hyaluronic acid)

INCHI for HMDB0002061 (Hyaluronic acid)

Structure for HMDB0002061 (Hyaluronic acid)

3D Structure for HMDB0002061 (Hyaluronic acid)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

GC-MS Spectra

MS/MS Spectra

NMR Spectra

Enzymes