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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2017-03-21 06:15:30 UTC

Update Date

2022-03-07 03:17:54 UTC

HMDB ID

HMDB0062408

Secondary Accession Numbers

HMDB62408

Metabolite Identification

Common Name

5S-hydroxy-6E,8Z,11Z,14Z,17Z-eicosapentaenoic acid

Description

5S-hydroxy-6E,8Z,11Z,14Z,17Z-eicosapentaenoic acid is classified as a member of the Hydroxyeicosapentaenoic acids. Hydroxyeicosapentaenoic acids are eicosanoic acids with an attached hydroxyl group and five CC double bonds. 5S-hydroxy-6E,8Z,11Z,14Z,17Z-eicosapentaenoic acid is considered to be practically insoluble (in water) and acidic. 5S-hydroxy-6E,8Z,11Z,14Z,17Z-eicosapentaenoic acid is an eicosanoid lipid molecule

Structure

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


  Mrv1652303211707152D          

 34 33  0  0  1  0            999 V2000
    6.0474    2.6664    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3329    3.0789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6184    2.6664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9039    3.0789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3329    3.9039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0474    4.3164    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6184    4.3164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6184    5.1414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3329    5.5539    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9039    5.5539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9039    6.3789    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1895    5.1414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750    5.5539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750    6.3789    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7605    5.1414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0461    5.5539    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7605    4.3164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0461    3.9039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3316    4.3164    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0461    3.0789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3316    2.6664    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7605    2.6664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750    3.0789    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7605    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0461    1.4289    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750    1.4289    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7605    1.0164    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750    0.6039    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1895    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9039    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6184    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3329    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0474    1.8414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3329    0.6039    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  0  0  0  0
  8 10  2  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  2  0  0  0  0
 15 16  1  0  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  2  0  0  0  0
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  2  0  0  0  0
 24 25  1  0  0  0  0
 24 26  1  0  0  0  0
 26 27  1  1  0  0  0
 26 28  1  6  0  0  0
 26 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

HMDB0062408
     RDKit          3D
5S-hydroxy-6E,8Z,11Z,14Z,17Z-eicosapentaenoic acid
 53 52  0  0  0  0  0  0  0  0999 V2000
   -8.4454   -0.4467    2.0858 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0714    0.1054    1.7070 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3226   -0.8147    0.8569 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8690   -0.5987   -0.3726 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0602    0.6288   -1.0767 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0459    1.5254   -1.5303 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7658    1.4700   -1.3779 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0856    0.3831   -0.6432 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2021   -0.3088   -1.6105 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9153   -0.3831   -1.3828 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2029    0.1729   -0.2009 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4826   -1.0324    0.4023 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7659   -1.0443    0.5191 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5914    0.0577    0.0950 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9257   -0.0181    0.2416 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8373    1.0592   -0.1609 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.4865    1.5323    0.9771 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8533    0.6731   -1.1806 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7719   -0.4327   -0.8063 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6048   -0.2227    0.4134 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4580   -1.4648    0.5678 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2299   -1.8694   -0.3507 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.4154   -2.2067    1.7400 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7981   -1.1174    1.2662 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1783    0.3951    2.1566 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4382   -0.9330    3.0765 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2257    1.0957    1.2834 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5649    0.2756    2.7023 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1026   -1.8216    1.2891 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3458   -1.4662   -0.8572 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6641    0.2910   -2.0478 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9314    1.2096   -0.5805 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4252    2.4390   -2.1271 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0969    2.2693   -1.8131 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6830   -0.2630   -0.0252 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4058    0.8991    0.1347 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6250   -0.7642   -2.5202 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2909   -0.9017   -2.1314 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8320    0.5322    0.6194 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4814    0.9687   -0.5087 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1778   -1.8269    0.7048 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2500   -1.9265    0.9569 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2738    0.9875   -0.3467 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3149   -0.9226    0.6764 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2570    1.9602   -0.5428 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8226    2.1045    1.4668 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4835    1.5329   -1.5105 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3321    0.3406   -2.1269 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4919   -0.5675   -1.6658 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2432   -1.4227   -0.7491 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0104   -0.1209    1.3435 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3093    0.6148    0.3506 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0788   -1.8855    2.6133 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  2  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 16 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  0
  7 34  1  0
  8 35  1  0
  8 36  1  0
  9 37  1  0
 10 38  1  0
 11 39  1  0
 11 40  1  0
 12 41  1  0
 13 42  1  0
 14 43  1  0
 15 44  1  0
 16 45  1  6
 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


  Mrv1652303211707152D          

 34 33  0  0  1  0            999 V2000
    6.0474    2.6664    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3329    3.0789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6184    2.6664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9039    3.0789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3329    3.9039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0474    4.3164    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6184    4.3164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6184    5.1414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3329    5.5539    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9039    5.5539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9039    6.3789    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1895    5.1414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750    5.5539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750    6.3789    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7605    5.1414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0461    5.5539    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7605    4.3164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0461    3.9039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3316    4.3164    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0461    3.0789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3316    2.6664    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7605    2.6664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750    3.0789    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7605    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0461    1.4289    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750    1.4289    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7605    1.0164    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750    0.6039    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1895    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9039    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6184    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3329    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0474    1.8414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3329    0.6039    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  0  0  0  0
  8 10  2  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  2  0  0  0  0
 15 16  1  0  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  2  0  0  0  0
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  2  0  0  0  0
 24 25  1  0  0  0  0
 24 26  1  0  0  0  0
 26 27  1  1  0  0  0
 26 28  1  6  0  0  0
 26 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>
HMDB0062408

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C20H30O3/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-16-19(21)17-15-18-20(22)23/h3-4,6-7,9-10,12-14,16,19,21H,2,5,8,11,15,17-18H2,1H3,(H,22,23)/b4-3-,7-6-,10-9-,13-12-,16-14+/t19-/m1/s1

> <INCHI_KEY>
FTAGQROYQYQRHF-GHWNLOBHSA-N

> <FORMULA>
C20H30O3

> <MOLECULAR_WEIGHT>
318.457

> <EXACT_MASS>
318.219494826

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
53

> <JCHEM_AVERAGE_POLARIZABILITY>
38.03690493662192

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(5S,6E,8Z,11Z,14Z,17Z)-5-hydroxyicosa-6,8,11,14,17-pentaenoic acid

> <ALOGPS_LOGP>
5.54

> <JCHEM_LOGP>
4.994438087333332

> <ALOGPS_LOGS>
-5.05

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
17.865306513915215

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.584101629727195

> <JCHEM_PKA_STRONGEST_BASIC>
-1.545515302673174

> <JCHEM_POLAR_SURFACE_AREA>
57.53

> <JCHEM_REFRACTIVITY>
102.5861

> <JCHEM_ROTATABLE_BOND_COUNT>
13

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.86e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5S-hepe

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0062408
     RDKit          3D
5S-hydroxy-6E,8Z,11Z,14Z,17Z-eicosapentaenoic acid
 53 52  0  0  0  0  0  0  0  0999 V2000
   -8.4454   -0.4467    2.0858 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0714    0.1054    1.7070 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3226   -0.8147    0.8569 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8690   -0.5987   -0.3726 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0602    0.6288   -1.0767 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0459    1.5254   -1.5303 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7658    1.4700   -1.3779 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0856    0.3831   -0.6432 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2021   -0.3088   -1.6105 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9153   -0.3831   -1.3828 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2029    0.1729   -0.2009 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4826   -1.0324    0.4023 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7659   -1.0443    0.5191 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5914    0.0577    0.0950 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9257   -0.0181    0.2416 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8373    1.0592   -0.1609 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.4865    1.5323    0.9771 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8533    0.6731   -1.1806 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7719   -0.4327   -0.8063 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6048   -0.2227    0.4134 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4580   -1.4648    0.5678 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2299   -1.8694   -0.3507 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.4154   -2.2067    1.7400 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7981   -1.1174    1.2662 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1783    0.3951    2.1566 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4382   -0.9330    3.0765 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2257    1.0957    1.2834 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5649    0.2756    2.7023 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1026   -1.8216    1.2891 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3458   -1.4662   -0.8572 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6641    0.2910   -2.0478 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9314    1.2096   -0.5805 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4252    2.4390   -2.1271 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0969    2.2693   -1.8131 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6830   -0.2630   -0.0252 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4058    0.8991    0.1347 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6250   -0.7642   -2.5202 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2909   -0.9017   -2.1314 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8320    0.5322    0.6194 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4814    0.9687   -0.5087 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1778   -1.8269    0.7048 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2500   -1.9265    0.9569 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2738    0.9875   -0.3467 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3149   -0.9226    0.6764 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2570    1.9602   -0.5428 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8226    2.1045    1.4668 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4835    1.5329   -1.5105 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3321    0.3406   -2.1269 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4919   -0.5675   -1.6658 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2432   -1.4227   -0.7491 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0104   -0.1209    1.3435 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3093    0.6148    0.3506 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0788   -1.8855    2.6133 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  2  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 16 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  0
  7 34  1  0
  8 35  1  0
  8 36  1  0
  9 37  1  0
 10 38  1  0
 11 39  1  0
 11 40  1  0
 12 41  1  0
 13 42  1  0
 14 43  1  0
 15 44  1  0
 16 45  1  6
 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                                 21-MAR-17   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   21-MAR-17         0                                  
HETATM    1  H   UNK     0      11.288   4.977   0.000  0.00  0.00           H+0
HETATM    2  C   UNK     0       9.955   5.747   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.621   4.977   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.287   5.747   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       9.955   7.287   0.000  0.00  0.00           C+0
HETATM    6  H   UNK     0      11.288   8.057   0.000  0.00  0.00           H+0
HETATM    7  C   UNK     0       8.621   8.057   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.621   9.597   0.000  0.00  0.00           C+0
HETATM    9  H   UNK     0       9.955  10.367   0.000  0.00  0.00           H+0
HETATM   10  C   UNK     0       7.287  10.367   0.000  0.00  0.00           C+0
HETATM   11  H   UNK     0       7.287  11.907   0.000  0.00  0.00           H+0
HETATM   12  C   UNK     0       5.954   9.597   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.620  10.367   0.000  0.00  0.00           C+0
HETATM   14  H   UNK     0       4.620  11.907   0.000  0.00  0.00           H+0
HETATM   15  C   UNK     0       3.286   9.597   0.000  0.00  0.00           C+0
HETATM   16  H   UNK     0       1.953  10.367   0.000  0.00  0.00           H+0
HETATM   17  C   UNK     0       3.286   8.057   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.953   7.287   0.000  0.00  0.00           C+0
HETATM   19  H   UNK     0       0.619   8.057   0.000  0.00  0.00           H+0
HETATM   20  C   UNK     0       1.953   5.747   0.000  0.00  0.00           C+0
HETATM   21  H   UNK     0       0.619   4.977   0.000  0.00  0.00           H+0
HETATM   22  C   UNK     0       3.286   4.977   0.000  0.00  0.00           C+0
HETATM   23  H   UNK     0       4.620   5.747   0.000  0.00  0.00           H+0
HETATM   24  C   UNK     0       3.286   3.437   0.000  0.00  0.00           C+0
HETATM   25  H   UNK     0       1.953   2.667   0.000  0.00  0.00           H+0
HETATM   26  C   UNK     0       4.620   2.667   0.000  0.00  0.00           C+0
HETATM   27  H   UNK     0       3.286   1.897   0.000  0.00  0.00           H+0
HETATM   28  O   UNK     0       4.620   1.127   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       5.954   3.437   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       7.287   2.667   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       8.621   3.437   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       9.955   2.667   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      11.288   3.437   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0       9.955   1.127   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                                                  
CONECT    9    8                                                            
CONECT   10    8   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   27   28   29                                             
CONECT   27   26                                                            
CONECT   28   26                                                            
CONECT   29   26   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    HMDB0062408
HETATM    1  C1  UNL     1      -8.445  -0.447   2.086  1.00  0.00           C  
HETATM    2  C2  UNL     1      -7.071   0.105   1.707  1.00  0.00           C  
HETATM    3  C3  UNL     1      -6.323  -0.815   0.857  1.00  0.00           C  
HETATM    4  C4  UNL     1      -5.869  -0.599  -0.373  1.00  0.00           C  
HETATM    5  C5  UNL     1      -6.060   0.629  -1.077  1.00  0.00           C  
HETATM    6  C6  UNL     1      -5.046   1.525  -1.530  1.00  0.00           C  
HETATM    7  C7  UNL     1      -3.766   1.470  -1.378  1.00  0.00           C  
HETATM    8  C8  UNL     1      -3.086   0.383  -0.643  1.00  0.00           C  
HETATM    9  C9  UNL     1      -2.202  -0.309  -1.610  1.00  0.00           C  
HETATM   10  C10 UNL     1      -0.915  -0.383  -1.383  1.00  0.00           C  
HETATM   11  C11 UNL     1      -0.203   0.173  -0.201  1.00  0.00           C  
HETATM   12  C12 UNL     1       0.483  -1.032   0.402  1.00  0.00           C  
HETATM   13  C13 UNL     1       1.766  -1.044   0.519  1.00  0.00           C  
HETATM   14  C14 UNL     1       2.591   0.058   0.095  1.00  0.00           C  
HETATM   15  C15 UNL     1       3.926  -0.018   0.242  1.00  0.00           C  
HETATM   16  C16 UNL     1       4.837   1.059  -0.161  1.00  0.00           C  
HETATM   17  O1  UNL     1       5.486   1.532   0.977  1.00  0.00           O  
HETATM   18  C17 UNL     1       5.853   0.673  -1.181  1.00  0.00           C  
HETATM   19  C18 UNL     1       6.772  -0.433  -0.806  1.00  0.00           C  
HETATM   20  C19 UNL     1       7.605  -0.223   0.413  1.00  0.00           C  
HETATM   21  C20 UNL     1       8.458  -1.465   0.568  1.00  0.00           C  
HETATM   22  O2  UNL     1       9.230  -1.869  -0.351  1.00  0.00           O  
HETATM   23  O3  UNL     1       8.415  -2.207   1.740  1.00  0.00           O  
HETATM   24  H1  UNL     1      -8.798  -1.117   1.266  1.00  0.00           H  
HETATM   25  H2  UNL     1      -9.178   0.395   2.157  1.00  0.00           H  
HETATM   26  H3  UNL     1      -8.438  -0.933   3.076  1.00  0.00           H  
HETATM   27  H4  UNL     1      -7.226   1.096   1.283  1.00  0.00           H  
HETATM   28  H5  UNL     1      -6.565   0.276   2.702  1.00  0.00           H  
HETATM   29  H6  UNL     1      -6.103  -1.822   1.289  1.00  0.00           H  
HETATM   30  H7  UNL     1      -5.346  -1.466  -0.857  1.00  0.00           H  
HETATM   31  H8  UNL     1      -6.664   0.291  -2.048  1.00  0.00           H  
HETATM   32  H9  UNL     1      -6.931   1.210  -0.580  1.00  0.00           H  
HETATM   33  H10 UNL     1      -5.425   2.439  -2.127  1.00  0.00           H  
HETATM   34  H11 UNL     1      -3.097   2.269  -1.813  1.00  0.00           H  
HETATM   35  H12 UNL     1      -3.683  -0.263  -0.025  1.00  0.00           H  
HETATM   36  H13 UNL     1      -2.406   0.899   0.135  1.00  0.00           H  
HETATM   37  H14 UNL     1      -2.625  -0.764  -2.520  1.00  0.00           H  
HETATM   38  H15 UNL     1      -0.291  -0.902  -2.131  1.00  0.00           H  
HETATM   39  H16 UNL     1      -0.832   0.532   0.619  1.00  0.00           H  
HETATM   40  H17 UNL     1       0.481   0.969  -0.509  1.00  0.00           H  
HETATM   41  H18 UNL     1      -0.178  -1.827   0.705  1.00  0.00           H  
HETATM   42  H19 UNL     1       2.250  -1.927   0.957  1.00  0.00           H  
HETATM   43  H20 UNL     1       2.274   0.988  -0.347  1.00  0.00           H  
HETATM   44  H21 UNL     1       4.315  -0.923   0.676  1.00  0.00           H  
HETATM   45  H22 UNL     1       4.257   1.960  -0.543  1.00  0.00           H  
HETATM   46  H23 UNL     1       4.823   2.104   1.467  1.00  0.00           H  
HETATM   47  H24 UNL     1       6.484   1.533  -1.510  1.00  0.00           H  
HETATM   48  H25 UNL     1       5.332   0.341  -2.127  1.00  0.00           H  
HETATM   49  H26 UNL     1       7.492  -0.567  -1.666  1.00  0.00           H  
HETATM   50  H27 UNL     1       6.243  -1.423  -0.749  1.00  0.00           H  
HETATM   51  H28 UNL     1       7.010  -0.121   1.344  1.00  0.00           H  
HETATM   52  H29 UNL     1       8.309   0.615   0.351  1.00  0.00           H  
HETATM   53  H30 UNL     1       8.079  -1.886   2.613  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    7   33
CONECT    7    8   34
CONECT    8    9   35   36
CONECT    9   10   10   37
CONECT   10   11   38
CONECT   11   12   39   40
CONECT   12   13   13   41
CONECT   13   14   42
CONECT   14   15   15   43
CONECT   15   16   44
CONECT   16   17   18   45
CONECT   17   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

HMDB0062408
     RDKit          3D
5S-hydroxy-6E,8Z,11Z,14Z,17Z-eicosapentaenoic acid
 53 52  0  0  0  0  0  0  0  0999 V2000
   -8.4454   -0.4467    2.0858 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0714    0.1054    1.7070 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3226   -0.8147    0.8569 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8690   -0.5987   -0.3726 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0602    0.6288   -1.0767 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0459    1.5254   -1.5303 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7658    1.4700   -1.3779 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0856    0.3831   -0.6432 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2021   -0.3088   -1.6105 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9153   -0.3831   -1.3828 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2029    0.1729   -0.2009 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4826   -1.0324    0.4023 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7659   -1.0443    0.5191 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5914    0.0577    0.0950 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9257   -0.0181    0.2416 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8373    1.0592   -0.1609 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.4865    1.5323    0.9771 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8533    0.6731   -1.1806 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7719   -0.4327   -0.8063 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6048   -0.2227    0.4134 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4580   -1.4648    0.5678 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2299   -1.8694   -0.3507 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.4154   -2.2067    1.7400 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7981   -1.1174    1.2662 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1783    0.3951    2.1566 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4382   -0.9330    3.0765 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2257    1.0957    1.2834 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5649    0.2756    2.7023 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1026   -1.8216    1.2891 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3458   -1.4662   -0.8572 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6641    0.2910   -2.0478 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9314    1.2096   -0.5805 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4252    2.4390   -2.1271 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0969    2.2693   -1.8131 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6830   -0.2630   -0.0252 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4058    0.8991    0.1347 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6250   -0.7642   -2.5202 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2909   -0.9017   -2.1314 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8320    0.5322    0.6194 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4814    0.9687   -0.5087 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1778   -1.8269    0.7048 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2500   -1.9265    0.9569 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2738    0.9875   -0.3467 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3149   -0.9226    0.6764 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2570    1.9602   -0.5428 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8226    2.1045    1.4668 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4835    1.5329   -1.5105 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3321    0.3406   -2.1269 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4919   -0.5675   -1.6658 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2432   -1.4227   -0.7491 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0104   -0.1209    1.3435 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3093    0.6148    0.3506 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0788   -1.8855    2.6133 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  2  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 16 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  0
  7 34  1  0
  8 35  1  0
  8 36  1  0
  9 37  1  0
 10 38  1  0
 11 39  1  0
 11 40  1  0
 12 41  1  0
 13 42  1  0
 14 43  1  0
 15 44  1  0
 16 45  1  6
 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
5S-Hydroxy-6E,8Z,11Z,14Z,17Z-eicosapentaenoate	Generator

Chemical Formula

C₂₀H₃₀O₃

Average Molecular Weight

318.457

Monoisotopic Molecular Weight

318.219494826

IUPAC Name

(5S,6E,8Z,11Z,14Z,17Z)-5-hydroxyicosa-6,8,11,14,17-pentaenoic acid

Traditional Name

5S-hepe

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C20H30O3/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-16-19(21)17-15-18-20(22)23/h3-4,6-7,9-10,12-14,16,19,21H,2,5,8,11,15,17-18H2,1H3,(H,22,23)/b4-3-,7-6-,10-9-,13-12-,16-14+/t19-/m1/s1

InChI Key

FTAGQROYQYQRHF-GHWNLOBHSA-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 (LMFA03070010 )

Ontology

Not Available

Exogenous (HMDB: HMDB0062408)

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	0.0029 g/l	ALOGPS
LogP	5.54	ALOGPS

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	5.54	ALOGPS
logP	4.99	ChemAxon
logS	-5	ALOGPS
pKa (Strongest Acidic)	4.58	ChemAxon
pKa (Strongest Basic)	-1.5	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	38.04 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]+	186.553	31661259
DarkChem	[M-H]-	184.349	31661259
DeepCCS	[M+H]+	199.394	30932474
DeepCCS	[M-H]-	197.569	30932474
DeepCCS	[M-2H]-	230.809	30932474
DeepCCS	[M+Na]+	205.0	30932474
AllCCS	[M+H]+	185.6	32859911
AllCCS	[M+H-H2O]+	182.6	32859911
AllCCS	[M+NH4]+	188.4	32859911
AllCCS	[M+Na]+	189.2	32859911
AllCCS	[M-H]-	183.6	32859911
AllCCS	[M+Na-2H]-	185.3	32859911
AllCCS	[M+HCOO]-	187.3	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.	5.85 minutes	32390414
Predicted by Siyang on May 30, 2022	21.6822 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	0.88 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	3066.0 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	436.3 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	193.8 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	318.5 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	575.2 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	1009.2 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	538.3 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	85.8 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	2041.5 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	722.2 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	1722.6 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	737.1 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	498.7 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	338.6 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	459.2 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	8.7 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
5S-hydroxy-6E,8Z,11Z,14Z,17Z-eicosapentaenoic acid	[H]\C(CC)=C(/[H])C\C([H])=C(\[H])C\C([H])=C(\[H])C\C([H])=C(\[H])/C(/[H])=C(\[H])[C@@]([H])(O)CCCC(O)=O	4276.1	Standard polar	33892256
5S-hydroxy-6E,8Z,11Z,14Z,17Z-eicosapentaenoic acid	[H]\C(CC)=C(/[H])C\C([H])=C(\[H])C\C([H])=C(\[H])C\C([H])=C(\[H])/C(/[H])=C(\[H])[C@@]([H])(O)CCCC(O)=O	2366.5	Standard non polar	33892256
5S-hydroxy-6E,8Z,11Z,14Z,17Z-eicosapentaenoic acid	[H]\C(CC)=C(/[H])C\C([H])=C(\[H])C\C([H])=C(\[H])C\C([H])=C(\[H])/C(/[H])=C(\[H])[C@@]([H])(O)CCCC(O)=O	2609.2	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
5S-hydroxy-6E,8Z,11Z,14Z,17Z-eicosapentaenoic acid,1TMS,isomer #1	CC/C=C\C/C=C\C/C=C\C/C=C\C=C\[C@H](CCCC(=O)O)O[Si](C)(C)C	2767.9	Semi standard non polar	33892256
5S-hydroxy-6E,8Z,11Z,14Z,17Z-eicosapentaenoic acid,1TMS,isomer #2	CC/C=C\C/C=C\C/C=C\C/C=C\C=C\[C@@H](O)CCCC(=O)O[Si](C)(C)C	2639.4	Semi standard non polar	33892256
5S-hydroxy-6E,8Z,11Z,14Z,17Z-eicosapentaenoic acid,2TMS,isomer #1	CC/C=C\C/C=C\C/C=C\C/C=C\C=C\[C@H](CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C	2718.3	Semi standard non polar	33892256
5S-hydroxy-6E,8Z,11Z,14Z,17Z-eicosapentaenoic acid,1TBDMS,isomer #1	CC/C=C\C/C=C\C/C=C\C/C=C\C=C\[C@H](CCCC(=O)O)O[Si](C)(C)C(C)(C)C	3014.0	Semi standard non polar	33892256
5S-hydroxy-6E,8Z,11Z,14Z,17Z-eicosapentaenoic acid,1TBDMS,isomer #2	CC/C=C\C/C=C\C/C=C\C/C=C\C=C\[C@@H](O)CCCC(=O)O[Si](C)(C)C(C)(C)C	2889.0	Semi standard non polar	33892256
5S-hydroxy-6E,8Z,11Z,14Z,17Z-eicosapentaenoic acid,2TBDMS,isomer #1	CC/C=C\C/C=C\C/C=C\C/C=C\C=C\[C@H](CCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3194.1	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 - 5S-hydroxy-6E,8Z,11Z,14Z,17Z-eicosapentaenoic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-0udi-5394000000-3c896430e353b0ced0db	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 5S-hydroxy-6E,8Z,11Z,14Z,17Z-eicosapentaenoic acid GC-MS (2 TMS) - 70eV, Positive	splash10-0umj-8209200000-58c4694ad173b557f3c5	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 5S-hydroxy-6E,8Z,11Z,14Z,17Z-eicosapentaenoic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 5S-hydroxy-6E,8Z,11Z,14Z,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 - 5S-hydroxy-6E,8Z,11Z,14Z,17Z-eicosapentaenoic acid 10V, Positive-QTOF	splash10-0udi-0149000000-dfe33b6babf270b34752	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5S-hydroxy-6E,8Z,11Z,14Z,17Z-eicosapentaenoic acid 20V, Positive-QTOF	splash10-0udu-5693000000-fb5c896d30ace0c553d8	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5S-hydroxy-6E,8Z,11Z,14Z,17Z-eicosapentaenoic acid 40V, Positive-QTOF	splash10-000l-9880000000-5d7665b416fe42c2c371	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5S-hydroxy-6E,8Z,11Z,14Z,17Z-eicosapentaenoic acid 10V, Negative-QTOF	splash10-014i-0069000000-023fef6c61163c7bc817	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5S-hydroxy-6E,8Z,11Z,14Z,17Z-eicosapentaenoic acid 20V, Negative-QTOF	splash10-00kb-2093000000-e62551450dc40c949d52	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5S-hydroxy-6E,8Z,11Z,14Z,17Z-eicosapentaenoic acid 40V, Negative-QTOF	splash10-0a4l-9160000000-b435064b3bb6876f2d7b	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5S-hydroxy-6E,8Z,11Z,14Z,17Z-eicosapentaenoic acid 10V, Positive-QTOF	splash10-0udi-1559000000-04ab13d626af1b826444	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5S-hydroxy-6E,8Z,11Z,14Z,17Z-eicosapentaenoic acid 20V, Positive-QTOF	splash10-0kha-4941000000-506babd9193b9c28a976	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5S-hydroxy-6E,8Z,11Z,14Z,17Z-eicosapentaenoic acid 40V, Positive-QTOF	splash10-00nf-9500000000-1b5d43f5a2984de18947	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5S-hydroxy-6E,8Z,11Z,14Z,17Z-eicosapentaenoic acid 10V, Negative-QTOF	splash10-014i-0019000000-c5853cf372543090df7d	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5S-hydroxy-6E,8Z,11Z,14Z,17Z-eicosapentaenoic acid 20V, Negative-QTOF	splash10-066r-5297000000-8a9ce241f524b80527f1	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5S-hydroxy-6E,8Z,11Z,14Z,17Z-eicosapentaenoic acid 40V, Negative-QTOF	splash10-0a4m-9840000000-d55d013e9ad27e3eb651	2021-09-24	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

5283193

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 5S-hydroxy-6E,8Z,11Z,14Z,17Z-eicosapentaenoic acid (HMDB0062408)

MOL for HMDB0062408 (5S-hydroxy-6E,8Z,11Z,14Z,17Z-eicosapentaenoic acid)

3D MOL for HMDB0062408 (5S-hydroxy-6E,8Z,11Z,14Z,17Z-eicosapentaenoic acid)

3D SDF for HMDB0062408 (5S-hydroxy-6E,8Z,11Z,14Z,17Z-eicosapentaenoic acid)

3D-SDF for HMDB0062408 (5S-hydroxy-6E,8Z,11Z,14Z,17Z-eicosapentaenoic acid)

PDB for HMDB0062408 (5S-hydroxy-6E,8Z,11Z,14Z,17Z-eicosapentaenoic acid)

3D PDB for HMDB0062408 (5S-hydroxy-6E,8Z,11Z,14Z,17Z-eicosapentaenoic acid)

SMILES for HMDB0062408 (5S-hydroxy-6E,8Z,11Z,14Z,17Z-eicosapentaenoic acid)

INCHI for HMDB0062408 (5S-hydroxy-6E,8Z,11Z,14Z,17Z-eicosapentaenoic acid)

Structure for HMDB0062408 (5S-hydroxy-6E,8Z,11Z,14Z,17Z-eicosapentaenoic acid)

3D Structure for HMDB0062408 (5S-hydroxy-6E,8Z,11Z,14Z,17Z-eicosapentaenoic acid)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra