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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2017-03-16 03:42:04 UTC

Update Date

2022-03-07 03:17:52 UTC

HMDB ID

HMDB0062296

Secondary Accession Numbers

HMDB62296

Metabolite Identification

Common Name

15S-hydroxy-5Z,8Z,11Z,13E,17Z-eicosapentaenoic acid

Description

15S-hydroxy-5Z,8Z,11Z,13E,17Z-eicosapentaenoic acid, also known as 15S-HEPE, is classified as a member of the Hydroxyeicosapentaenoic acids. Hydroxyeicosapentaenoic acids are eicosanoic acids with an attached hydroxyl group and five CC double bonds. 15S-hydroxy-5Z,8Z,11Z,13E,17Z-eicosapentaenoic acid is considered to be practically insoluble (in water) and acidic. 15S-hydroxy-5Z,8Z,11Z,13E,17Z-eicosapentaenoic acid is an eicosanoid lipid molecule

Structure

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

  Mrv1652303161704422D          

 34 33  0  0  1  0            999 V2000
    4.0954    3.1895    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3809    3.6020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6664    3.1895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6664    2.3645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3809    4.4270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0954    4.8395    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6664    4.8395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9520    4.4270    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6664    4.0145    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9520    3.6020    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375    4.8395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375    5.6645    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5230    4.4270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5230    3.6020    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1914    4.8395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1914    5.6645    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9059    4.4270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6204    4.8395    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9059    3.6020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6204    3.1895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3349    3.6020    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6204    2.3645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3349    1.9520    0.0000 H   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 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6664   -0.1105    0.0000 O   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
  2  5  2  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  1  0  0  0
  8 10  1  6  0  0  0
  8 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  2  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  2  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  2  0  0  0  0
 22 23  1  0  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  2  0  0  0  0
 27 28  1  0  0  0  0
 27 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
 32 33  1  0  0  0  0
 32 34  2  0  0  0  0
M  END

HMDB0062296
     RDKit          3D
15S-hydroxy-5Z,8Z,11Z,13E,17Z-eicosapentaenoic acid
 53 52  0  0  0  0  0  0  0  0999 V2000
    8.5213    0.2936    0.3997 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3983   -0.0671   -0.5719 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4071    1.0174   -0.6792 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1465    0.8129   -0.3547 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5442   -0.4316    0.1351 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4442   -0.9384   -0.7912 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.0107   -1.1786   -2.0647 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3537    0.0222   -0.9649 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2103    0.0064   -0.2465 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1886    1.0004   -0.4922 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9152    1.0029    0.1863 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1888   -0.0351    1.2686 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3663    0.6792    2.5281 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4004    0.6449    3.3066 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6326   -0.1012    3.1479 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9071   -1.0291    2.0916 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8364   -0.9975    1.1467 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8067    0.0668    1.0154 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8005    0.9000   -0.2192 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9537    0.2305   -1.5253 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8541   -0.6409   -1.9664 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7402   -0.5942   -1.4122 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0658   -1.5228   -3.0123 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.5204    0.0006    0.0222 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5554    1.3629    0.6233 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3441   -0.3464    1.3030 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9430   -0.1929   -1.5659 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9883   -1.0622   -0.3739 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6942    1.9997   -1.0254 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4227    1.6603   -0.4497 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0373   -0.1581    1.1149 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1985   -1.2564    0.3647 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1314   -1.9260   -0.4079 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7593   -2.0620   -2.4105 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4259    0.8083   -1.7010 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1913   -0.7921    0.4696 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3399    1.7482   -1.2443 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6872    1.7322    0.0200 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0539   -0.5767    0.9233 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3690   -0.7578    1.3552 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5073    1.3421    2.8733 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3258    1.3030    4.2613 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4644    0.6962    3.1644 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8318   -0.6486    4.1647 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2842   -1.9754    2.0511 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8582   -1.8794    0.4686 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8764   -0.3734    1.1450 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7627    0.7799    1.8744 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8574    1.5252   -0.1836 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6716    1.6175   -0.1118 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1784    1.0231   -2.3002 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8812   -0.4195   -1.5715 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6991   -2.3129   -2.8944 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 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
  4 30  1  0
  5 31  1  0
  5 32  1  0
  6 33  1  1
  7 34  1  0
  8 35  1  0
  9 36  1  0
 10 37  1  0
 11 38  1  0
 12 39  1  0
 12 40  1  0
 13 41  1  0
 14 42  1  0
 15 43  1  0
 15 44  1  0
 16 45  1  0
 17 46  1  0
 18 47  1  0
 18 48  1  0
 19 49  1  0
 19 50  1  0
 20 51  1  0
 20 52  1  0
 23 53  1  0
M  END

  Mrv1652303161704422D          

 34 33  0  0  1  0            999 V2000
    4.0954    3.1895    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3809    3.6020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6664    3.1895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6664    2.3645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3809    4.4270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0954    4.8395    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6664    4.8395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9520    4.4270    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6664    4.0145    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9520    3.6020    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375    4.8395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375    5.6645    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5230    4.4270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5230    3.6020    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1914    4.8395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1914    5.6645    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9059    4.4270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6204    4.8395    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9059    3.6020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6204    3.1895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3349    3.6020    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6204    2.3645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3349    1.9520    0.0000 H   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 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6664   -0.1105    0.0000 O   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
  2  5  2  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  1  0  0  0
  8 10  1  6  0  0  0
  8 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  2  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  2  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  2  0  0  0  0
 22 23  1  0  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  2  0  0  0  0
 27 28  1  0  0  0  0
 27 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
 32 33  1  0  0  0  0
 32 34  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0062296

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C20H30O3/c1-2-3-13-16-19(21)17-14-11-9-7-5-4-6-8-10-12-15-18-20(22)23/h3-5,8-11,13-14,17,19,21H,2,6-7,12,15-16,18H2,1H3,(H,22,23)/b5-4-,10-8-,11-9-,13-3-,17-14+/t19-/m0/s1

> <INCHI_KEY>
WLKCSMCLEKGITB-DBVSHIMFSA-N

> <FORMULA>
C20H30O3

> <MOLECULAR_WEIGHT>
318.457

> <EXACT_MASS>
318.219494826

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
53

> <JCHEM_AVERAGE_POLARIZABILITY>
37.56555073350559

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(5Z,8Z,11Z,13E,15S,17Z)-15-hydroxyicosa-5,8,11,13,17-pentaenoic acid

> <ALOGPS_LOGP>
5.55

> <JCHEM_LOGP>
4.994438087333332

> <ALOGPS_LOGS>
-5.02

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
17.720826441407528

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.8197720024427735

> <JCHEM_PKA_STRONGEST_BASIC>
-1.6087106764488617

> <JCHEM_POLAR_SURFACE_AREA>
57.53

> <JCHEM_REFRACTIVITY>
102.58609999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
13

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.06e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
15S-hepe

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0062296
     RDKit          3D
15S-hydroxy-5Z,8Z,11Z,13E,17Z-eicosapentaenoic acid
 53 52  0  0  0  0  0  0  0  0999 V2000
    8.5213    0.2936    0.3997 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3983   -0.0671   -0.5719 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4071    1.0174   -0.6792 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1465    0.8129   -0.3547 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5442   -0.4316    0.1351 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4442   -0.9384   -0.7912 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.0107   -1.1786   -2.0647 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3537    0.0222   -0.9649 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2103    0.0064   -0.2465 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1886    1.0004   -0.4922 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9152    1.0029    0.1863 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1888   -0.0351    1.2686 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3663    0.6792    2.5281 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4004    0.6449    3.3066 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6326   -0.1012    3.1479 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9071   -1.0291    2.0916 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8364   -0.9975    1.1467 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8067    0.0668    1.0154 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8005    0.9000   -0.2192 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9537    0.2305   -1.5253 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8541   -0.6409   -1.9664 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7402   -0.5942   -1.4122 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0658   -1.5228   -3.0123 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.5204    0.0006    0.0222 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5554    1.3629    0.6233 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3441   -0.3464    1.3030 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9430   -0.1929   -1.5659 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9883   -1.0622   -0.3739 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6942    1.9997   -1.0254 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4227    1.6603   -0.4497 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0373   -0.1581    1.1149 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1985   -1.2564    0.3647 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1314   -1.9260   -0.4079 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7593   -2.0620   -2.4105 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4259    0.8083   -1.7010 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1913   -0.7921    0.4696 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3399    1.7482   -1.2443 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6872    1.7322    0.0200 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0539   -0.5767    0.9233 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3690   -0.7578    1.3552 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5073    1.3421    2.8733 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3258    1.3030    4.2613 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4644    0.6962    3.1644 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8318   -0.6486    4.1647 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2842   -1.9754    2.0511 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8582   -1.8794    0.4686 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8764   -0.3734    1.1450 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7627    0.7799    1.8744 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8574    1.5252   -0.1836 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6716    1.6175   -0.1118 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1784    1.0231   -2.3002 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8812   -0.4195   -1.5715 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6991   -2.3129   -2.8944 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 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
  4 30  1  0
  5 31  1  0
  5 32  1  0
  6 33  1  1
  7 34  1  0
  8 35  1  0
  9 36  1  0
 10 37  1  0
 11 38  1  0
 12 39  1  0
 12 40  1  0
 13 41  1  0
 14 42  1  0
 15 43  1  0
 15 44  1  0
 16 45  1  0
 17 46  1  0
 18 47  1  0
 18 48  1  0
 19 49  1  0
 19 50  1  0
 20 51  1  0
 20 52  1  0
 23 53  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       7.645   5.954   0.000  0.00  0.00           H+0
HETATM    2  C   UNK     0       6.311   6.724   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.977   5.954   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.977   4.414   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.311   8.264   0.000  0.00  0.00           C+0
HETATM    6  H   UNK     0       7.645   9.034   0.000  0.00  0.00           H+0
HETATM    7  C   UNK     0       4.977   9.034   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.644   8.264   0.000  0.00  0.00           C+0
HETATM    9  H   UNK     0       4.977   7.494   0.000  0.00  0.00           H+0
HETATM   10  O   UNK     0       3.644   6.724   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       2.310   9.034   0.000  0.00  0.00           C+0
HETATM   12  H   UNK     0       2.310  10.574   0.000  0.00  0.00           H+0
HETATM   13  C   UNK     0       0.976   8.264   0.000  0.00  0.00           C+0
HETATM   14  H   UNK     0       0.976   6.724   0.000  0.00  0.00           H+0
HETATM   15  C   UNK     0      -0.357   9.034   0.000  0.00  0.00           C+0
HETATM   16  H   UNK     0      -0.357  10.574   0.000  0.00  0.00           H+0
HETATM   17  C   UNK     0      -1.691   8.264   0.000  0.00  0.00           C+0
HETATM   18  H   UNK     0      -3.025   9.034   0.000  0.00  0.00           H+0
HETATM   19  C   UNK     0      -1.691   6.724   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -3.025   5.954   0.000  0.00  0.00           C+0
HETATM   21  H   UNK     0      -4.358   6.724   0.000  0.00  0.00           H+0
HETATM   22  C   UNK     0      -3.025   4.414   0.000  0.00  0.00           C+0
HETATM   23  H   UNK     0      -4.358   3.644   0.000  0.00  0.00           H+0
HETATM   24  C   UNK     0      -1.691   3.644   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -1.691   2.104   0.000  0.00  0.00           C+0
HETATM   26  H   UNK     0      -3.025   1.334   0.000  0.00  0.00           H+0
HETATM   27  C   UNK     0      -0.357   1.334   0.000  0.00  0.00           C+0
HETATM   28  H   UNK     0      -0.357  -0.206   0.000  0.00  0.00           H+0
HETATM   29  C   UNK     0       0.976   2.104   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       2.310   1.334   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       3.644   2.104   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       4.977   1.334   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       6.311   2.104   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0       4.977  -0.206   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    5                                                  
CONECT    3    2    4                                                       
CONECT    4    3                                                            
CONECT    5    2    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9   10   11                                             
CONECT    9    8                                                            
CONECT   10    8                                                            
CONECT   11    8   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25                                                       
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   66    0
END

COMPND    HMDB0062296
HETATM    1  C1  UNL     1       8.521   0.294   0.400  1.00  0.00           C  
HETATM    2  C2  UNL     1       7.398  -0.067  -0.572  1.00  0.00           C  
HETATM    3  C3  UNL     1       6.407   1.017  -0.679  1.00  0.00           C  
HETATM    4  C4  UNL     1       5.146   0.813  -0.355  1.00  0.00           C  
HETATM    5  C5  UNL     1       4.544  -0.432   0.135  1.00  0.00           C  
HETATM    6  C6  UNL     1       3.444  -0.938  -0.791  1.00  0.00           C  
HETATM    7  O1  UNL     1       4.011  -1.179  -2.065  1.00  0.00           O  
HETATM    8  C7  UNL     1       2.354   0.022  -0.965  1.00  0.00           C  
HETATM    9  C8  UNL     1       1.210   0.006  -0.246  1.00  0.00           C  
HETATM   10  C9  UNL     1       0.189   1.000  -0.492  1.00  0.00           C  
HETATM   11  C10 UNL     1      -0.915   1.003   0.186  1.00  0.00           C  
HETATM   12  C11 UNL     1      -1.189  -0.035   1.269  1.00  0.00           C  
HETATM   13  C12 UNL     1      -1.366   0.679   2.528  1.00  0.00           C  
HETATM   14  C13 UNL     1      -2.400   0.645   3.307  1.00  0.00           C  
HETATM   15  C14 UNL     1      -3.633  -0.101   3.148  1.00  0.00           C  
HETATM   16  C15 UNL     1      -3.907  -1.029   2.092  1.00  0.00           C  
HETATM   17  C16 UNL     1      -4.836  -0.998   1.147  1.00  0.00           C  
HETATM   18  C17 UNL     1      -5.807   0.067   1.015  1.00  0.00           C  
HETATM   19  C18 UNL     1      -5.801   0.900  -0.219  1.00  0.00           C  
HETATM   20  C19 UNL     1      -5.954   0.231  -1.525  1.00  0.00           C  
HETATM   21  C20 UNL     1      -4.854  -0.641  -1.966  1.00  0.00           C  
HETATM   22  O2  UNL     1      -3.740  -0.594  -1.412  1.00  0.00           O  
HETATM   23  O3  UNL     1      -5.066  -1.523  -3.012  1.00  0.00           O  
HETATM   24  H1  UNL     1       9.520   0.001   0.022  1.00  0.00           H  
HETATM   25  H2  UNL     1       8.555   1.363   0.623  1.00  0.00           H  
HETATM   26  H3  UNL     1       8.344  -0.346   1.303  1.00  0.00           H  
HETATM   27  H4  UNL     1       7.943  -0.193  -1.566  1.00  0.00           H  
HETATM   28  H5  UNL     1       6.988  -1.062  -0.374  1.00  0.00           H  
HETATM   29  H6  UNL     1       6.694   2.000  -1.025  1.00  0.00           H  
HETATM   30  H7  UNL     1       4.423   1.660  -0.450  1.00  0.00           H  
HETATM   31  H8  UNL     1       4.037  -0.158   1.115  1.00  0.00           H  
HETATM   32  H9  UNL     1       5.199  -1.256   0.365  1.00  0.00           H  
HETATM   33  H10 UNL     1       3.131  -1.926  -0.408  1.00  0.00           H  
HETATM   34  H11 UNL     1       3.759  -2.062  -2.410  1.00  0.00           H  
HETATM   35  H12 UNL     1       2.426   0.808  -1.701  1.00  0.00           H  
HETATM   36  H13 UNL     1       1.191  -0.792   0.470  1.00  0.00           H  
HETATM   37  H14 UNL     1       0.340   1.748  -1.244  1.00  0.00           H  
HETATM   38  H15 UNL     1      -1.687   1.732   0.020  1.00  0.00           H  
HETATM   39  H16 UNL     1      -2.054  -0.577   0.923  1.00  0.00           H  
HETATM   40  H17 UNL     1      -0.369  -0.758   1.355  1.00  0.00           H  
HETATM   41  H18 UNL     1      -0.507   1.342   2.873  1.00  0.00           H  
HETATM   42  H19 UNL     1      -2.326   1.303   4.261  1.00  0.00           H  
HETATM   43  H20 UNL     1      -4.464   0.696   3.164  1.00  0.00           H  
HETATM   44  H21 UNL     1      -3.832  -0.649   4.165  1.00  0.00           H  
HETATM   45  H22 UNL     1      -3.284  -1.975   2.051  1.00  0.00           H  
HETATM   46  H23 UNL     1      -4.858  -1.879   0.469  1.00  0.00           H  
HETATM   47  H24 UNL     1      -6.876  -0.373   1.145  1.00  0.00           H  
HETATM   48  H25 UNL     1      -5.763   0.780   1.874  1.00  0.00           H  
HETATM   49  H26 UNL     1      -4.857   1.525  -0.184  1.00  0.00           H  
HETATM   50  H27 UNL     1      -6.672   1.617  -0.112  1.00  0.00           H  
HETATM   51  H28 UNL     1      -6.178   1.023  -2.300  1.00  0.00           H  
HETATM   52  H29 UNL     1      -6.881  -0.420  -1.572  1.00  0.00           H  
HETATM   53  H30 UNL     1      -5.699  -2.313  -2.894  1.00  0.00           H  
CONECT    1    2   24   25   26
CONECT    2    3   27   28
CONECT    3    4    4   29
CONECT    4    5   30
CONECT    5    6   31   32
CONECT    6    7    8   33
CONECT    7   34
CONECT    8    9    9   35
CONECT    9   10   36
CONECT   10   11   11   37
CONECT   11   12   38
CONECT   12   13   39   40
CONECT   13   14   14   41
CONECT   14   15   42
CONECT   15   16   43   44
CONECT   16   17   17   45
CONECT   17   18   46
CONECT   18   19   47   48
CONECT   19   20   49   50
CONECT   20   21   51   52
CONECT   21   22   22   23
CONECT   23   53
END

HMDB0062296
     RDKit          3D
15S-hydroxy-5Z,8Z,11Z,13E,17Z-eicosapentaenoic acid
 53 52  0  0  0  0  0  0  0  0999 V2000
    8.5213    0.2936    0.3997 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3983   -0.0671   -0.5719 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4071    1.0174   -0.6792 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1465    0.8129   -0.3547 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5442   -0.4316    0.1351 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4442   -0.9384   -0.7912 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.0107   -1.1786   -2.0647 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3537    0.0222   -0.9649 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2103    0.0064   -0.2465 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1886    1.0004   -0.4922 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9152    1.0029    0.1863 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1888   -0.0351    1.2686 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3663    0.6792    2.5281 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4004    0.6449    3.3066 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6326   -0.1012    3.1479 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9071   -1.0291    2.0916 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8364   -0.9975    1.1467 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8067    0.0668    1.0154 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8005    0.9000   -0.2192 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9537    0.2305   -1.5253 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8541   -0.6409   -1.9664 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7402   -0.5942   -1.4122 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0658   -1.5228   -3.0123 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.5204    0.0006    0.0222 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5554    1.3629    0.6233 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3441   -0.3464    1.3030 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9430   -0.1929   -1.5659 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9883   -1.0622   -0.3739 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6942    1.9997   -1.0254 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4227    1.6603   -0.4497 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0373   -0.1581    1.1149 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1985   -1.2564    0.3647 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1314   -1.9260   -0.4079 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7593   -2.0620   -2.4105 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4259    0.8083   -1.7010 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1913   -0.7921    0.4696 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3399    1.7482   -1.2443 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6872    1.7322    0.0200 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0539   -0.5767    0.9233 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3690   -0.7578    1.3552 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5073    1.3421    2.8733 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3258    1.3030    4.2613 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4644    0.6962    3.1644 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8318   -0.6486    4.1647 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2842   -1.9754    2.0511 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8582   -1.8794    0.4686 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8764   -0.3734    1.1450 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7627    0.7799    1.8744 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8574    1.5252   -0.1836 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6716    1.6175   -0.1118 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1784    1.0231   -2.3002 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8812   -0.4195   -1.5715 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6991   -2.3129   -2.8944 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 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
  4 30  1  0
  5 31  1  0
  5 32  1  0
  6 33  1  1
  7 34  1  0
  8 35  1  0
  9 36  1  0
 10 37  1  0
 11 38  1  0
 12 39  1  0
 12 40  1  0
 13 41  1  0
 14 42  1  0
 15 43  1  0
 15 44  1  0
 16 45  1  0
 17 46  1  0
 18 47  1  0
 18 48  1  0
 19 49  1  0
 19 50  1  0
 20 51  1  0
 20 52  1  0
 23 53  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(5Z,8Z,11Z,13E,15S,17Z)-15-Hydroxyicosapentaenoic acid	ChEBI
15S-HEPE	ChEBI
15S-Hydroxy-5Z,8Z,11Z,13E,17Z-eicosapentaenoic acid	ChEBI
(5Z,8Z,11Z,13E,15S,17Z)-15-Hydroxyicosapentaenoate	Generator
15S-Hydroxy-5Z,8Z,11Z,13E,17Z-eicosapentaenoate	Generator

Chemical Formula

C₂₀H₃₀O₃

Average Molecular Weight

318.457

Monoisotopic Molecular Weight

318.219494826

IUPAC Name

(5Z,8Z,11Z,13E,15S,17Z)-15-hydroxyicosa-5,8,11,13,17-pentaenoic acid

Traditional Name

15S-hepe

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C20H30O3/c1-2-3-13-16-19(21)17-14-11-9-7-5-4-6-8-10-12-15-18-20(22)23/h3-5,8-11,13-14,17,19,21H,2,6-7,12,15-16,18H2,1H3,(H,22,23)/b5-4-,10-8-,11-9-,13-3-,17-14+/t19-/m0/s1

InChI Key

WLKCSMCLEKGITB-DBVSHIMFSA-N

Chemical Taxonomy

Description

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

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Eicosanoids

Direct Parent

Hydroxyeicosapentaenoic acids

Alternative Parents

Substituents

Hydroxyeicosapentaenoic 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

Hydroxy/hydroperoxyeicosapentaenoic acids (LMFA03070009 )

Ontology

Not Available

Exogenous (HMDB: HMDB0062296)

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	0.0031 g/l	ALOGPS
LogP	5.55	ALOGPS

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	5.55	ALOGPS
logP	4.99	ChemAxon
logS	-5	ALOGPS
pKa (Strongest Acidic)	4.82	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	13	ChemAxon
Refractivity	102.59 m³·mol⁻¹	ChemAxon
Polarizability	37.57 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	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]+	188.516	31661259
DarkChem	[M-H]-	186.116	31661259
DeepCCS	[M+H]+	213.765	30932474
DeepCCS	[M-H]-	211.87	30932474
DeepCCS	[M-2H]-	245.402	30932474
DeepCCS	[M+Na]+	219.452	30932474
AllCCS	[M+H]+	185.5	32859911
AllCCS	[M+H-H2O]+	182.5	32859911
AllCCS	[M+NH4]+	188.2	32859911
AllCCS	[M+Na]+	189.0	32859911
AllCCS	[M-H]-	183.1	32859911
AllCCS	[M+Na-2H]-	184.7	32859911
AllCCS	[M+HCOO]-	186.7	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
15S-hydroxy-5Z,8Z,11Z,13E,17Z-eicosapentaenoic acid	[H]\C(CC)=C(/[H])C[C@]([H])(O)C(\[H])=C(/[H])\C(\[H])=C(\[H])C\C([H])=C(\[H])C\C([H])=C(\[H])CCCC(O)=O	4248.8	Standard polar	33892256
15S-hydroxy-5Z,8Z,11Z,13E,17Z-eicosapentaenoic acid	[H]\C(CC)=C(/[H])C[C@]([H])(O)C(\[H])=C(/[H])\C(\[H])=C(\[H])C\C([H])=C(\[H])C\C([H])=C(\[H])CCCC(O)=O	2337.4	Standard non polar	33892256
15S-hydroxy-5Z,8Z,11Z,13E,17Z-eicosapentaenoic acid	[H]\C(CC)=C(/[H])C[C@]([H])(O)C(\[H])=C(/[H])\C(\[H])=C(\[H])C\C([H])=C(\[H])C\C([H])=C(\[H])CCCC(O)=O	2587.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
15S-hydroxy-5Z,8Z,11Z,13E,17Z-eicosapentaenoic acid,1TMS,isomer #1	CC/C=C\C[C@@H](/C=C/C=C\C/C=C\C/C=C\CCCC(=O)O)O[Si](C)(C)C	2761.9	Semi standard non polar	33892256
15S-hydroxy-5Z,8Z,11Z,13E,17Z-eicosapentaenoic acid,1TMS,isomer #2	CC/C=C\C[C@H](O)/C=C/C=C\C/C=C\C/C=C\CCCC(=O)O[Si](C)(C)C	2638.6	Semi standard non polar	33892256
15S-hydroxy-5Z,8Z,11Z,13E,17Z-eicosapentaenoic acid,2TMS,isomer #1	CC/C=C\C[C@@H](/C=C/C=C\C/C=C\C/C=C\CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C	2720.6	Semi standard non polar	33892256
15S-hydroxy-5Z,8Z,11Z,13E,17Z-eicosapentaenoic acid,1TBDMS,isomer #1	CC/C=C\C[C@@H](/C=C/C=C\C/C=C\C/C=C\CCCC(=O)O)O[Si](C)(C)C(C)(C)C	3007.3	Semi standard non polar	33892256
15S-hydroxy-5Z,8Z,11Z,13E,17Z-eicosapentaenoic acid,1TBDMS,isomer #2	CC/C=C\C[C@H](O)/C=C/C=C\C/C=C\C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C	2883.6	Semi standard non polar	33892256
15S-hydroxy-5Z,8Z,11Z,13E,17Z-eicosapentaenoic acid,2TBDMS,isomer #1	CC/C=C\C[C@@H](/C=C/C=C\C/C=C\C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3200.4	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 - 15S-hydroxy-5Z,8Z,11Z,13E,17Z-eicosapentaenoic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-0gbc-7192000000-80fb061f4893b98fc916	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 15S-hydroxy-5Z,8Z,11Z,13E,17Z-eicosapentaenoic acid GC-MS (2 TMS) - 70eV, Positive	splash10-00fr-9325200000-ec091e75ea7bdf1c7e32	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 15S-hydroxy-5Z,8Z,11Z,13E,17Z-eicosapentaenoic 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 - 15S-hydroxy-5Z,8Z,11Z,13E,17Z-eicosapentaenoic acid 10V, Positive-QTOF	splash10-0udi-0059000000-b14d85c391199749293d	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 15S-hydroxy-5Z,8Z,11Z,13E,17Z-eicosapentaenoic acid 20V, Positive-QTOF	splash10-0q29-5393000000-269d667b30487e873a45	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 15S-hydroxy-5Z,8Z,11Z,13E,17Z-eicosapentaenoic acid 40V, Positive-QTOF	splash10-0ab9-9830000000-4d9c3662da6e7214994b	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 15S-hydroxy-5Z,8Z,11Z,13E,17Z-eicosapentaenoic acid 10V, Negative-QTOF	splash10-014i-0059000000-bc25dd9d7efaf3a01d90	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 15S-hydroxy-5Z,8Z,11Z,13E,17Z-eicosapentaenoic acid 20V, Negative-QTOF	splash10-014j-2093000000-a57de046f7134e151174	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 15S-hydroxy-5Z,8Z,11Z,13E,17Z-eicosapentaenoic acid 40V, Negative-QTOF	splash10-0a4l-9140000000-2893e6a7c9d14d19668d	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 15S-hydroxy-5Z,8Z,11Z,13E,17Z-eicosapentaenoic acid 10V, Negative-QTOF	splash10-00kb-0095000000-753419a2174c1ccd0c8e	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 15S-hydroxy-5Z,8Z,11Z,13E,17Z-eicosapentaenoic acid 20V, Negative-QTOF	splash10-0002-1192000000-088be68de03acac5a997	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 15S-hydroxy-5Z,8Z,11Z,13E,17Z-eicosapentaenoic acid 40V, Negative-QTOF	splash10-0005-9130000000-832ef4c32981a71f659a	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 15S-hydroxy-5Z,8Z,11Z,13E,17Z-eicosapentaenoic acid 10V, Positive-QTOF	splash10-0udi-0479000000-9096a5ea6fbf6d1c2714	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 15S-hydroxy-5Z,8Z,11Z,13E,17Z-eicosapentaenoic acid 20V, Positive-QTOF	splash10-0w39-2973000000-d239c0a5bf2f5b647494	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 15S-hydroxy-5Z,8Z,11Z,13E,17Z-eicosapentaenoic acid 40V, Positive-QTOF	splash10-015c-7900000000-15c82b91d69e16161b0e	2021-09-23	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

5283192

PDB ID

Not Available

ChEBI ID

88347

Food Biomarker Ontology

Not Available

VMH ID

CE7082

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 15S-hydroxy-5Z,8Z,11Z,13E,17Z-eicosapentaenoic acid (HMDB0062296)

MOL for HMDB0062296 (15S-hydroxy-5Z,8Z,11Z,13E,17Z-eicosapentaenoic acid)

3D MOL for HMDB0062296 (15S-hydroxy-5Z,8Z,11Z,13E,17Z-eicosapentaenoic acid)

3D SDF for HMDB0062296 (15S-hydroxy-5Z,8Z,11Z,13E,17Z-eicosapentaenoic acid)

3D-SDF for HMDB0062296 (15S-hydroxy-5Z,8Z,11Z,13E,17Z-eicosapentaenoic acid)

PDB for HMDB0062296 (15S-hydroxy-5Z,8Z,11Z,13E,17Z-eicosapentaenoic acid)

3D PDB for HMDB0062296 (15S-hydroxy-5Z,8Z,11Z,13E,17Z-eicosapentaenoic acid)

SMILES for HMDB0062296 (15S-hydroxy-5Z,8Z,11Z,13E,17Z-eicosapentaenoic acid)

INCHI for HMDB0062296 (15S-hydroxy-5Z,8Z,11Z,13E,17Z-eicosapentaenoic acid)

Structure for HMDB0062296 (15S-hydroxy-5Z,8Z,11Z,13E,17Z-eicosapentaenoic acid)

3D Structure for HMDB0062296 (15S-hydroxy-5Z,8Z,11Z,13E,17Z-eicosapentaenoic acid)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra