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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2017-03-16 03:41:45 UTC

Update Date

2022-03-07 03:17:52 UTC

HMDB ID

HMDB0062287

Secondary Accession Numbers

HMDB62287

Metabolite Identification

Common Name

12S-hydroxy-5E,8Z,10Z,14Z-eicosatetraenoic acid

Description

12S-hydroxy-5E,8Z,10Z,14Z-eicosatetraenoic acid, also known as 12-S-HETE or Acid, 12-S-hydroxyeicosatetraenoic, is classified as a member of the Hydroxyeicosatetraenoic acids. Hydroxyeicosatetraenoic acids are eicosanoic acids with an attached hydroxyl group and four CC double bonds. 12S-hydroxy-5E,8Z,10Z,14Z-eicosatetraenoic acid is considered to be practically insoluble (in water) and acidic. 12S-hydroxy-5E,8Z,10Z,14Z-eicosatetraenoic acid is an eicosanoid lipid molecule

Structure

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


  Mrv1652303161704412D          

 32 31  0  0  1  0            999 V2000
   -5.1927    3.6020    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9072    3.1895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6217    3.6020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6217    4.4270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3362    4.8395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3362    5.6645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0506    6.0770    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6217    6.0770    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9072    2.3645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6217    1.9520    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1927    1.9520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4783    2.3645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4783    3.1895    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7638    1.9520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7638    1.1270    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0493    2.3645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0493    3.1895    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3349    1.9520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3349    1.1270    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6204    2.3645    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.3349    2.7770    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6204    3.1895    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9059    1.9520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9059    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6204    0.7145    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1914    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1914   -0.1105    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5230    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9520    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6664    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3809    1.1270    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
  6  7  1  0  0  0  0
  6  8  2  0  0  0  0
  2  9  2  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  4  0  0  0
 12 14  2  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
 16 17  1  4  0  0  0
 16 18  2  0  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
 20 21  1  6  0  0  0
 20 22  1  1  0  0  0
 20 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 24 26  2  0  0  0  0
 26 27  1  0  0  0  0
 26 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
M  END

HMDB0062287
     RDKit          3D
12S-hydroxy-5E,8Z,10Z,14Z-eicosatetraenoic acid
 55 54  0  0  0  0  0  0  0  0999 V2000
    8.7535   -0.2451    0.1881 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1674    0.6903   -0.8285 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7327    0.4687   -1.1070 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9525    0.6078    0.2085 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4597    0.5619   -0.0647 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9508   -0.5769   -0.7762 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0437   -1.3948   -0.3128 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4325   -1.2567    0.9943 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9275   -0.9084    0.8235 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2961   -1.8120    0.0962 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8041    0.5120    0.4924 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2668    1.1959    0.2404 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5850    0.6096    0.2518 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5957    1.3147    0.0590 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7188    2.0896   -0.1538 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9570    1.2283   -0.4685 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7728   -0.0335   -0.6537 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9446   -0.9582   -0.9736 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2556   -0.2391   -0.8884 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4906    0.0512    0.5843 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7056    0.8314    0.8492 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.4688    1.3020   -0.0492 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0329    1.0552    2.1900 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1296   -0.4137    1.0847 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.6758    0.2964    0.6048 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.0864   -1.2013   -0.2522 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7363    0.5255   -1.7778 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2974    1.7529   -0.4601 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5651   -0.5693   -1.4906 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3356    1.1885   -1.8534 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1769   -0.1932    0.9091 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1478    1.6579    0.6004 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2355    1.4769   -0.7121 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0199    0.7931    0.9364 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3291   -0.7939   -1.8163 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6818   -2.2538   -0.9505 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3699   -2.2995    1.4355 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9381   -0.6507    1.7497 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4968   -0.9861    1.8872 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7085   -1.9231   -0.8340 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7908    1.0954    0.4655 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1663    2.2511    0.0209 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5604   -0.4995    0.4375 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3599    0.3817    0.8163 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6517    2.7850   -1.0854 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9874    2.8002    0.6808 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8718    1.7655   -0.5477 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7942   -0.4998   -0.6343 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7633   -1.4710   -1.9395 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8590   -1.7867   -0.2076 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0459   -0.9153   -1.3257 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2633    0.6903   -1.4708 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6688   -0.9903    1.0302 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6196    0.4311    1.0795 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8362    0.3679    2.9183 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  9 11  1  0
 11 12  2  3
 12 13  1  0
 13 14  2  3
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  2  0
 21 23  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  2 27  1  0
  2 28  1  0
  3 29  1  0
  3 30  1  0
  4 31  1  0
  4 32  1  0
  5 33  1  0
  5 34  1  0
  6 35  1  0
  7 36  1  0
  8 37  1  0
  8 38  1  0
  9 39  1  1
 10 40  1  0
 11 41  1  0
 12 42  1  0
 13 43  1  0
 14 44  1  0
 15 45  1  0
 15 46  1  0
 16 47  1  0
 17 48  1  0
 18 49  1  0
 18 50  1  0
 19 51  1  0
 19 52  1  0
 20 53  1  0
 20 54  1  0
 23 55  1  0
M  END


  Mrv1652303161704412D          

 32 31  0  0  1  0            999 V2000
   -5.1927    3.6020    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9072    3.1895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6217    3.6020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6217    4.4270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3362    4.8395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3362    5.6645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0506    6.0770    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6217    6.0770    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9072    2.3645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6217    1.9520    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1927    1.9520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4783    2.3645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4783    3.1895    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7638    1.9520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7638    1.1270    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0493    2.3645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0493    3.1895    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3349    1.9520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3349    1.1270    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6204    2.3645    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.3349    2.7770    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6204    3.1895    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9059    1.9520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9059    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6204    0.7145    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1914    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1914   -0.1105    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5230    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9520    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6664    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3809    1.1270    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
  6  7  1  0  0  0  0
  6  8  2  0  0  0  0
  2  9  2  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  4  0  0  0
 12 14  2  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
 16 17  1  4  0  0  0
 16 18  2  0  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
 20 21  1  6  0  0  0
 20 22  1  1  0  0  0
 20 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 24 26  2  0  0  0  0
 26 27  1  0  0  0  0
 26 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0062287

> <DATABASE_NAME>
hmdb

> <SMILES>
[H]\C(CCCC(O)=O)=C(\[H])CC([H])=C([H])C([H])=C([H])[C@@]([H])(O)C\C([H])=C(\[H])CCCCC

> <INCHI_IDENTIFIER>
InChI=1S/C20H32O3/c1-2-3-4-5-10-13-16-19(21)17-14-11-8-6-7-9-12-15-18-20(22)23/h7-11,13-14,17,19,21H,2-6,12,15-16,18H2,1H3,(H,22,23)/b9-7+,11-8?,13-10-,17-14?/t19-/m0/s1

> <INCHI_KEY>
ZNHVWPKMFKADKW-SEXNTHKDSA-N

> <FORMULA>
C20H32O3

> <MOLECULAR_WEIGHT>
320.473

> <EXACT_MASS>
320.23514489

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
55

> <JCHEM_AVERAGE_POLARIZABILITY>
39.38075402186712

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(5E,12S,14Z)-12-hydroxyicosa-5,8,10,14-tetraenoic acid

> <ALOGPS_LOGP>
5.86

> <JCHEM_LOGP>
5.356359744

> <ALOGPS_LOGS>
-5.26

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
17.720826396394717

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.889630645050488

> <JCHEM_PKA_STRONGEST_BASIC>
-1.608710672078515

> <JCHEM_POLAR_SURFACE_AREA>
57.53

> <JCHEM_REFRACTIVITY>
101.4695

> <JCHEM_ROTATABLE_BOND_COUNT>
14

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.74e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(5E,12S,14Z)-12-hydroxyicosa-5,8,10,14-tetraenoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0062287
     RDKit          3D
12S-hydroxy-5E,8Z,10Z,14Z-eicosatetraenoic acid
 55 54  0  0  0  0  0  0  0  0999 V2000
    8.7535   -0.2451    0.1881 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1674    0.6903   -0.8285 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7327    0.4687   -1.1070 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9525    0.6078    0.2085 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4597    0.5619   -0.0647 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9508   -0.5769   -0.7762 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0437   -1.3948   -0.3128 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4325   -1.2567    0.9943 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9275   -0.9084    0.8235 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2961   -1.8120    0.0962 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8041    0.5120    0.4924 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2668    1.1959    0.2404 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5850    0.6096    0.2518 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5957    1.3147    0.0590 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7188    2.0896   -0.1538 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9570    1.2283   -0.4685 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7728   -0.0335   -0.6537 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9446   -0.9582   -0.9736 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2556   -0.2391   -0.8884 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4906    0.0512    0.5843 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7056    0.8314    0.8492 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.4688    1.3020   -0.0492 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0329    1.0552    2.1900 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1296   -0.4137    1.0847 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.6758    0.2964    0.6048 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.0864   -1.2013   -0.2522 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7363    0.5255   -1.7778 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2974    1.7529   -0.4601 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5651   -0.5693   -1.4906 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3356    1.1885   -1.8534 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1769   -0.1932    0.9091 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1478    1.6579    0.6004 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2355    1.4769   -0.7121 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0199    0.7931    0.9364 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3291   -0.7939   -1.8163 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6818   -2.2538   -0.9505 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3699   -2.2995    1.4355 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9381   -0.6507    1.7497 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4968   -0.9861    1.8872 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7085   -1.9231   -0.8340 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7908    1.0954    0.4655 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1663    2.2511    0.0209 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5604   -0.4995    0.4375 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3599    0.3817    0.8163 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6517    2.7850   -1.0854 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9874    2.8002    0.6808 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8718    1.7655   -0.5477 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7942   -0.4998   -0.6343 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7633   -1.4710   -1.9395 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8590   -1.7867   -0.2076 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0459   -0.9153   -1.3257 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2633    0.6903   -1.4708 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6688   -0.9903    1.0302 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6196    0.4311    1.0795 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8362    0.3679    2.9183 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  9 11  1  0
 11 12  2  3
 12 13  1  0
 13 14  2  3
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  2  0
 21 23  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  2 27  1  0
  2 28  1  0
  3 29  1  0
  3 30  1  0
  4 31  1  0
  4 32  1  0
  5 33  1  0
  5 34  1  0
  6 35  1  0
  7 36  1  0
  8 37  1  0
  8 38  1  0
  9 39  1  1
 10 40  1  0
 11 41  1  0
 12 42  1  0
 13 43  1  0
 14 44  1  0
 15 45  1  0
 15 46  1  0
 16 47  1  0
 17 48  1  0
 18 49  1  0
 18 50  1  0
 19 51  1  0
 19 52  1  0
 20 53  1  0
 20 54  1  0
 23 55  1  0
M  END

HEADER    PROTEIN                                 16-MAR-17   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   16-MAR-17         0                                  
HETATM    1  H   UNK     0      -9.693   6.724   0.000  0.00  0.00           H+0
HETATM    2  C   UNK     0     -11.027   5.954   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0     -12.360   6.724   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0     -12.360   8.264   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0     -13.694   9.034   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0     -13.694  10.574   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0     -15.028  11.344   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0     -12.360  11.344   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0     -11.027   4.414   0.000  0.00  0.00           C+0
HETATM   10  H   UNK     0     -12.360   3.644   0.000  0.00  0.00           H+0
HETATM   11  C   UNK     0      -9.693   3.644   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -8.359   4.414   0.000  0.00  0.00           C+0
HETATM   13  H   UNK     0      -8.359   5.954   0.000  0.00  0.00           H+0
HETATM   14  C   UNK     0      -7.026   3.644   0.000  0.00  0.00           C+0
HETATM   15  H   UNK     0      -7.026   2.104   0.000  0.00  0.00           H+0
HETATM   16  C   UNK     0      -5.692   4.414   0.000  0.00  0.00           C+0
HETATM   17  H   UNK     0      -5.692   5.954   0.000  0.00  0.00           H+0
HETATM   18  C   UNK     0      -4.358   3.644   0.000  0.00  0.00           C+0
HETATM   19  H   UNK     0      -4.358   2.104   0.000  0.00  0.00           H+0
HETATM   20  C   UNK     0      -3.025   4.414   0.000  0.00  0.00           C+0
HETATM   21  H   UNK     0      -4.358   5.184   0.000  0.00  0.00           H+0
HETATM   22  O   UNK     0      -3.025   5.954   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      -1.691   3.644   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -1.691   2.104   0.000  0.00  0.00           C+0
HETATM   25  H   UNK     0      -3.025   1.334   0.000  0.00  0.00           H+0
HETATM   26  C   UNK     0      -0.357   1.334   0.000  0.00  0.00           C+0
HETATM   27  H   UNK     0      -0.357  -0.206   0.000  0.00  0.00           H+0
HETATM   28  C   UNK     0       0.976   2.104   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       2.310   1.334   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       3.644   2.104   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       4.977   1.334   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       6.311   2.104   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    9                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6                                                            
CONECT    9    2   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21   22   23                                             
CONECT   21   20                                                            
CONECT   22   20                                                            
CONECT   23   20   24                                                       
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31                                                            
MASTER        0    0    0    0    0    0    0    0   32    0   62    0
END

COMPND    HMDB0062287
HETATM    1  C1  UNL     1       8.753  -0.245   0.188  1.00  0.00           C  
HETATM    2  C2  UNL     1       8.167   0.690  -0.828  1.00  0.00           C  
HETATM    3  C3  UNL     1       6.733   0.469  -1.107  1.00  0.00           C  
HETATM    4  C4  UNL     1       5.952   0.608   0.209  1.00  0.00           C  
HETATM    5  C5  UNL     1       4.460   0.562  -0.065  1.00  0.00           C  
HETATM    6  C6  UNL     1       3.951  -0.577  -0.776  1.00  0.00           C  
HETATM    7  C7  UNL     1       3.044  -1.395  -0.313  1.00  0.00           C  
HETATM    8  C8  UNL     1       2.432  -1.257   0.994  1.00  0.00           C  
HETATM    9  C9  UNL     1       0.927  -0.908   0.823  1.00  0.00           C  
HETATM   10  O1  UNL     1       0.296  -1.812   0.096  1.00  0.00           O  
HETATM   11  C10 UNL     1       0.804   0.512   0.492  1.00  0.00           C  
HETATM   12  C11 UNL     1      -0.267   1.196   0.240  1.00  0.00           C  
HETATM   13  C12 UNL     1      -1.585   0.610   0.252  1.00  0.00           C  
HETATM   14  C13 UNL     1      -2.596   1.315   0.059  1.00  0.00           C  
HETATM   15  C14 UNL     1      -3.719   2.090  -0.154  1.00  0.00           C  
HETATM   16  C15 UNL     1      -4.957   1.228  -0.469  1.00  0.00           C  
HETATM   17  C16 UNL     1      -4.773  -0.033  -0.654  1.00  0.00           C  
HETATM   18  C17 UNL     1      -5.945  -0.958  -0.974  1.00  0.00           C  
HETATM   19  C18 UNL     1      -7.256  -0.239  -0.888  1.00  0.00           C  
HETATM   20  C19 UNL     1      -7.491   0.051   0.584  1.00  0.00           C  
HETATM   21  C20 UNL     1      -8.706   0.831   0.849  1.00  0.00           C  
HETATM   22  O2  UNL     1      -9.469   1.302  -0.049  1.00  0.00           O  
HETATM   23  O3  UNL     1      -9.033   1.055   2.190  1.00  0.00           O  
HETATM   24  H1  UNL     1       8.130  -0.414   1.085  1.00  0.00           H  
HETATM   25  H2  UNL     1       9.676   0.296   0.605  1.00  0.00           H  
HETATM   26  H3  UNL     1       9.086  -1.201  -0.252  1.00  0.00           H  
HETATM   27  H4  UNL     1       8.736   0.526  -1.778  1.00  0.00           H  
HETATM   28  H5  UNL     1       8.297   1.753  -0.460  1.00  0.00           H  
HETATM   29  H6  UNL     1       6.565  -0.569  -1.491  1.00  0.00           H  
HETATM   30  H7  UNL     1       6.336   1.189  -1.853  1.00  0.00           H  
HETATM   31  H8  UNL     1       6.177  -0.193   0.909  1.00  0.00           H  
HETATM   32  H9  UNL     1       6.148   1.658   0.600  1.00  0.00           H  
HETATM   33  H10 UNL     1       4.235   1.477  -0.712  1.00  0.00           H  
HETATM   34  H11 UNL     1       4.020   0.793   0.936  1.00  0.00           H  
HETATM   35  H12 UNL     1       4.329  -0.794  -1.816  1.00  0.00           H  
HETATM   36  H13 UNL     1       2.682  -2.254  -0.951  1.00  0.00           H  
HETATM   37  H14 UNL     1       2.370  -2.300   1.435  1.00  0.00           H  
HETATM   38  H15 UNL     1       2.938  -0.651   1.750  1.00  0.00           H  
HETATM   39  H16 UNL     1       0.497  -0.986   1.887  1.00  0.00           H  
HETATM   40  H17 UNL     1       0.708  -1.923  -0.834  1.00  0.00           H  
HETATM   41  H18 UNL     1       1.791   1.095   0.466  1.00  0.00           H  
HETATM   42  H19 UNL     1      -0.166   2.251   0.021  1.00  0.00           H  
HETATM   43  H20 UNL     1      -1.560  -0.500   0.438  1.00  0.00           H  
HETATM   44  H21 UNL     1      -3.360   0.382   0.816  1.00  0.00           H  
HETATM   45  H22 UNL     1      -3.652   2.785  -1.085  1.00  0.00           H  
HETATM   46  H23 UNL     1      -3.987   2.800   0.681  1.00  0.00           H  
HETATM   47  H24 UNL     1      -5.872   1.766  -0.548  1.00  0.00           H  
HETATM   48  H25 UNL     1      -3.794  -0.500  -0.634  1.00  0.00           H  
HETATM   49  H26 UNL     1      -5.763  -1.471  -1.940  1.00  0.00           H  
HETATM   50  H27 UNL     1      -5.859  -1.787  -0.208  1.00  0.00           H  
HETATM   51  H28 UNL     1      -8.046  -0.915  -1.326  1.00  0.00           H  
HETATM   52  H29 UNL     1      -7.263   0.690  -1.471  1.00  0.00           H  
HETATM   53  H30 UNL     1      -7.669  -0.990   1.030  1.00  0.00           H  
HETATM   54  H31 UNL     1      -6.620   0.431   1.079  1.00  0.00           H  
HETATM   55  H32 UNL     1      -8.836   0.368   2.918  1.00  0.00           H  
CONECT    1    2   24   25   26
CONECT    2    3   27   28
CONECT    3    4   29   30
CONECT    4    5   31   32
CONECT    5    6   33   34
CONECT    6    7    7   35
CONECT    7    8   36
CONECT    8    9   37   38
CONECT    9   10   11   39
CONECT   10   40
CONECT   11   12   12   41
CONECT   12   13   42
CONECT   13   14   14   43
CONECT   14   15   44
CONECT   15   16   45   46
CONECT   16   17   17   47
CONECT   17   18   48
CONECT   18   19   49   50
CONECT   19   20   51   52
CONECT   20   21   53   54
CONECT   21   22   22   23
CONECT   23   55
END

HMDB0062287
     RDKit          3D
12S-hydroxy-5E,8Z,10Z,14Z-eicosatetraenoic acid
 55 54  0  0  0  0  0  0  0  0999 V2000
    8.7535   -0.2451    0.1881 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1674    0.6903   -0.8285 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7327    0.4687   -1.1070 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9525    0.6078    0.2085 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4597    0.5619   -0.0647 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9508   -0.5769   -0.7762 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0437   -1.3948   -0.3128 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4325   -1.2567    0.9943 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9275   -0.9084    0.8235 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2961   -1.8120    0.0962 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8041    0.5120    0.4924 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2668    1.1959    0.2404 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5850    0.6096    0.2518 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5957    1.3147    0.0590 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7188    2.0896   -0.1538 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9570    1.2283   -0.4685 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7728   -0.0335   -0.6537 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9446   -0.9582   -0.9736 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2556   -0.2391   -0.8884 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4906    0.0512    0.5843 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7056    0.8314    0.8492 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.4688    1.3020   -0.0492 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0329    1.0552    2.1900 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1296   -0.4137    1.0847 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.6758    0.2964    0.6048 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.0864   -1.2013   -0.2522 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7363    0.5255   -1.7778 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2974    1.7529   -0.4601 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5651   -0.5693   -1.4906 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3356    1.1885   -1.8534 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1769   -0.1932    0.9091 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1478    1.6579    0.6004 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2355    1.4769   -0.7121 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0199    0.7931    0.9364 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3291   -0.7939   -1.8163 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6818   -2.2538   -0.9505 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3699   -2.2995    1.4355 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9381   -0.6507    1.7497 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4968   -0.9861    1.8872 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7085   -1.9231   -0.8340 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7908    1.0954    0.4655 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1663    2.2511    0.0209 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5604   -0.4995    0.4375 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3599    0.3817    0.8163 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6517    2.7850   -1.0854 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9874    2.8002    0.6808 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8718    1.7655   -0.5477 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7942   -0.4998   -0.6343 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7633   -1.4710   -1.9395 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8590   -1.7867   -0.2076 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0459   -0.9153   -1.3257 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2633    0.6903   -1.4708 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6688   -0.9903    1.0302 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6196    0.4311    1.0795 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8362    0.3679    2.9183 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  9 11  1  0
 11 12  2  3
 12 13  1  0
 13 14  2  3
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  2  0
 21 23  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  2 27  1  0
  2 28  1  0
  3 29  1  0
  3 30  1  0
  4 31  1  0
  4 32  1  0
  5 33  1  0
  5 34  1  0
  6 35  1  0
  7 36  1  0
  8 37  1  0
  8 38  1  0
  9 39  1  1
 10 40  1  0
 11 41  1  0
 12 42  1  0
 13 43  1  0
 14 44  1  0
 15 45  1  0
 15 46  1  0
 16 47  1  0
 17 48  1  0
 18 49  1  0
 18 50  1  0
 19 51  1  0
 19 52  1  0
 20 53  1  0
 20 54  1  0
 23 55  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(5E,12S,14Z)-12-Hydroxyicosa-5,8,10,14-tetraenoate	Generator
12S-Hydroxy-5E,8Z,10Z,14Z-eicosatetraenoate	Generator
12 S Hydroxyeicosatetraenoic acid	HMDB
12-HETE	HMDB
12-Hydroxy-5,8,10,14-eicosatetraenoic acid	HMDB
12-R-HETE	HMDB
12-S-HETE	HMDB
12-S-Hydroxyeicosatetraenoic acid	HMDB
Acid, 12-S-hydroxyeicosatetraenoic	HMDB

Chemical Formula

C₂₀H₃₂O₃

Average Molecular Weight

320.473

Monoisotopic Molecular Weight

320.23514489

IUPAC Name

(5E,12S,14Z)-12-hydroxyicosa-5,8,10,14-tetraenoic acid

Traditional Name

(5E,12S,14Z)-12-hydroxyicosa-5,8,10,14-tetraenoic acid

CAS Registry Number

Not Available

SMILES

[H]\C(CCCC(O)=O)=C(\[H])CC([H])=C([H])C([H])=C([H])[C@@]([H])(O)C\C([H])=C(\[H])CCCCC

InChI Identifier

InChI=1S/C20H32O3/c1-2-3-4-5-10-13-16-19(21)17-14-11-8-6-7-9-12-15-18-20(22)23/h7-11,13-14,17,19,21H,2-6,12,15-16,18H2,1H3,(H,22,23)/b9-7+,11-8?,13-10-,17-14?/t19-/m0/s1

InChI Key

ZNHVWPKMFKADKW-SEXNTHKDSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as hydroxyeicosatetraenoic acids. These are eicosanoic acids with an attached hydroxyl group and four CC double bonds.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Eicosanoids

Direct Parent

Hydroxyeicosatetraenoic acids

Alternative Parents

Substituents

Hydroxyeicosatetraenoic acid
Long-chain fatty acid
Hydroxy fatty acid
Fatty acid
Unsaturated fatty acid
Secondary alcohol
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Organic oxide
Organic oxygen compound
Alcohol
Hydrocarbon derivative
Carbonyl group
Organooxygen compound
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Exogenous (HMDB: HMDB0062287)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.0017 g/l	ALOGPS
LogP	5.86	ALOGPS

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	5.86	ALOGPS
logP	5.36	ChemAxon
logS	-5.3	ALOGPS
pKa (Strongest Acidic)	4.89	ChemAxon
pKa (Strongest Basic)	-1.6	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	57.53 Å²	ChemAxon
Rotatable Bond Count	14	ChemAxon
Refractivity	101.47 m³·mol⁻¹	ChemAxon
Polarizability	39.38 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	189.204	31661259
DarkChem	[M-H]-	191.582	31661259
DeepCCS	[M+H]+	188.055	30932474
DeepCCS	[M-H]-	186.23	30932474
DeepCCS	[M-2H]-	219.472	30932474
DeepCCS	[M+Na]+	193.661	30932474
AllCCS	[M+H]+	186.9	32859911
AllCCS	[M+H-H2O]+	184.0	32859911
AllCCS	[M+NH4]+	189.6	32859911
AllCCS	[M+Na]+	190.4	32859911
AllCCS	[M-H]-	185.5	32859911
AllCCS	[M+Na-2H]-	187.3	32859911
AllCCS	[M+HCOO]-	189.4	32859911

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 √ó 2.1 mm; 1.7 Œºmparticle diameter). Predicted by Afia on May 17, 2022.	6.94 minutes	32390414
Predicted by Siyang on May 30, 2022	21.1491 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.04 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	3120.5 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	414.1 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	201.0 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	268.6 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	622.4 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	977.2 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	555.3 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	108.5 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	2054.0 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	685.2 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	1683.0 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	715.6 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	491.1 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	338.8 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	495.7 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	8.6 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
12S-hydroxy-5E,8Z,10Z,14Z-eicosatetraenoic acid	[H]\C(CCCC(O)=O)=C(\[H])CC([H])=C([H])C([H])=C([H])[C@@]([H])(O)C\C([H])=C(\[H])CCCCC	4088.6	Standard polar	33892256
12S-hydroxy-5E,8Z,10Z,14Z-eicosatetraenoic acid	[H]\C(CCCC(O)=O)=C(\[H])CC([H])=C([H])C([H])=C([H])[C@@]([H])(O)C\C([H])=C(\[H])CCCCC	2364.2	Standard non polar	33892256
12S-hydroxy-5E,8Z,10Z,14Z-eicosatetraenoic acid	[H]\C(CCCC(O)=O)=C(\[H])CC([H])=C([H])C([H])=C([H])[C@@]([H])(O)C\C([H])=C(\[H])CCCCC	2600.0	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
12S-hydroxy-5E,8Z,10Z,14Z-eicosatetraenoic acid,1TMS,isomer #1	CCCCC/C=C\C[C@H](O)C=CC=CC/C=C/CCCC(=O)O[Si](C)(C)C	2633.5	Semi standard non polar	33892256
12S-hydroxy-5E,8Z,10Z,14Z-eicosatetraenoic acid,1TMS,isomer #2	CCCCC/C=C\C[C@@H](C=CC=CC/C=C/CCCC(=O)O)O[Si](C)(C)C	2737.0	Semi standard non polar	33892256
12S-hydroxy-5E,8Z,10Z,14Z-eicosatetraenoic acid,2TMS,isomer #1	CCCCC/C=C\C[C@@H](C=CC=CC/C=C/CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C	2706.2	Semi standard non polar	33892256
12S-hydroxy-5E,8Z,10Z,14Z-eicosatetraenoic acid,1TBDMS,isomer #1	CCCCC/C=C\C[C@H](O)C=CC=CC/C=C/CCCC(=O)O[Si](C)(C)C(C)(C)C	2875.1	Semi standard non polar	33892256
12S-hydroxy-5E,8Z,10Z,14Z-eicosatetraenoic acid,1TBDMS,isomer #2	CCCCC/C=C\C[C@@H](C=CC=CC/C=C/CCCC(=O)O)O[Si](C)(C)C(C)(C)C	2983.3	Semi standard non polar	33892256
12S-hydroxy-5E,8Z,10Z,14Z-eicosatetraenoic acid,2TBDMS,isomer #1	CCCCC/C=C\C[C@@H](C=CC=CC/C=C/CCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3192.4	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 12S-hydroxy-5E,8Z,10Z,14Z-eicosatetraenoic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-0k96-9682000000-3d0587aa644521928ce5	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 12S-hydroxy-5E,8Z,10Z,14Z-eicosatetraenoic acid GC-MS (2 TMS) - 70eV, Positive	splash10-00b9-9214200000-eed18646199bed4a6431	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 12S-hydroxy-5E,8Z,10Z,14Z-eicosatetraenoic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 12S-hydroxy-5E,8Z,10Z,14Z-eicosatetraenoic acid 10V, Positive-QTOF	splash10-0udi-0149000000-74c8a329f23fadacb126	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 12S-hydroxy-5E,8Z,10Z,14Z-eicosatetraenoic acid 20V, Positive-QTOF	splash10-1170-5894000000-64209b422fb0758bc6fe	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 12S-hydroxy-5E,8Z,10Z,14Z-eicosatetraenoic acid 40V, Positive-QTOF	splash10-05mo-9630000000-04b83893c8c26c8e5a7e	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 12S-hydroxy-5E,8Z,10Z,14Z-eicosatetraenoic acid 10V, Negative-QTOF	splash10-014i-0019000000-a230e97019aecf4548b9	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 12S-hydroxy-5E,8Z,10Z,14Z-eicosatetraenoic acid 20V, Negative-QTOF	splash10-0uxr-1249000000-f91706196bc952f52fe5	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 12S-hydroxy-5E,8Z,10Z,14Z-eicosatetraenoic acid 40V, Negative-QTOF	splash10-0a4l-9830000000-fb14870af49ed2b68478	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 12S-hydroxy-5E,8Z,10Z,14Z-eicosatetraenoic acid 10V, Negative-QTOF	splash10-014i-0009000000-6256931c61a3add16e83	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 12S-hydroxy-5E,8Z,10Z,14Z-eicosatetraenoic acid 20V, Negative-QTOF	splash10-0gb9-0239000000-a17ea0bea562b61dc708	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 12S-hydroxy-5E,8Z,10Z,14Z-eicosatetraenoic acid 40V, Negative-QTOF	splash10-052f-9440000000-1881f139597265fdda5f	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 12S-hydroxy-5E,8Z,10Z,14Z-eicosatetraenoic acid 10V, Positive-QTOF	splash10-0uk9-2329000000-5fdf4fb096e2b9c13da8	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 12S-hydroxy-5E,8Z,10Z,14Z-eicosatetraenoic acid 20V, Positive-QTOF	splash10-0f7c-5942000000-17d22db7e5c4882a7225	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 12S-hydroxy-5E,8Z,10Z,14Z-eicosatetraenoic acid 40V, Positive-QTOF	splash10-00l6-9510000000-6714e0af28b839029cb5	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Showing metabocard for 12S-hydroxy-5E,8Z,10Z,14Z-eicosatetraenoic acid (HMDB0062287)

MOL for HMDB0062287 (12S-hydroxy-5E,8Z,10Z,14Z-eicosatetraenoic acid)

3D MOL for HMDB0062287 (12S-hydroxy-5E,8Z,10Z,14Z-eicosatetraenoic acid)

3D SDF for HMDB0062287 (12S-hydroxy-5E,8Z,10Z,14Z-eicosatetraenoic acid)

3D-SDF for HMDB0062287 (12S-hydroxy-5E,8Z,10Z,14Z-eicosatetraenoic acid)

PDB for HMDB0062287 (12S-hydroxy-5E,8Z,10Z,14Z-eicosatetraenoic acid)

3D PDB for HMDB0062287 (12S-hydroxy-5E,8Z,10Z,14Z-eicosatetraenoic acid)

SMILES for HMDB0062287 (12S-hydroxy-5E,8Z,10Z,14Z-eicosatetraenoic acid)

INCHI for HMDB0062287 (12S-hydroxy-5E,8Z,10Z,14Z-eicosatetraenoic acid)

Structure for HMDB0062287 (12S-hydroxy-5E,8Z,10Z,14Z-eicosatetraenoic acid)

3D Structure for HMDB0062287 (12S-hydroxy-5E,8Z,10Z,14Z-eicosatetraenoic acid)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra