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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2006-10-18 11:41:18 UTC

Update Date

2022-03-07 02:49:25 UTC

HMDB ID

HMDB0005045

Secondary Accession Numbers

HMDB05045

Metabolite Identification

Common Name

15(S)-Hydroxyeicosatrienoic acid

Description

15(S)-hydroxyeicosatrienoic acid (15S-HETrE) is the in vivo metabolite of gamma-linolenic acid, a polyunsaturated fatty acid that have been reported to modulate arachidonic acid (AA) metabolism and tumorigenesis. 15S-HETrE suppress cyclooxygenase-2 (COX-2) over expression and/or Prostaglandin E2 (PGE2) biosynthesis (PMID 15197770 ), and inhibits [(3)H]thymidine uptake in parallel with the upregulation of peroxisome proliferator-activated receptor-gamma expression (a growth modulating nuclear receptor, PPARgamma). (PMID 12445673 ).

Structure

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

HMDB0005045
     RDKit          3D
15(S)-Hydroxyeicosatrienoic acid
 57 56  0  0  0  0  0  0  0  0999 V2000
    8.4163    0.0569    0.4062 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3931   -0.2722   -0.6586 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7686    0.9614   -1.2769 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7692    0.5621   -2.3064 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6312   -0.2653   -1.8289 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7520    0.3518   -0.7934 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.5502    0.6458    0.3377 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7915   -0.6759   -0.3118 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7913   -0.3803    0.5324 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9197   -1.4222    0.9448 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0890   -1.2527    1.7684 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4273    0.0221    2.3502 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7057    0.6676    2.1340 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7449    0.3624    1.4236 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9455   -0.7997    0.5628 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3103   -0.4322   -0.8467 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4807    0.3657   -1.1416 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8563   -0.0349   -0.8133 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1174   -0.1454    0.6487 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5558   -0.5504    0.9449 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4687    0.4868    0.4576 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.7085    0.1847    0.4363 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1253    1.7535    0.0223 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.2367   -0.6257    1.2910 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.4339   -0.1100    0.0018 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2636    1.1023    0.7062 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9184   -0.7953   -1.5164 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6330   -0.9897   -0.3281 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5924    1.4978   -1.8427 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3962    1.6957   -0.5660 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3787    1.4399   -2.8611 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3165   -0.0543   -3.0671 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9522   -1.2814   -1.4954 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9794   -0.4603   -2.7298 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2617    1.2715   -1.1564 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6491   -0.1702    0.9033 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8933   -1.6797   -0.6396 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7219    0.6325    0.8322 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0836   -2.4608    0.5542 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6905   -2.1757    2.0521 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3892    0.7779    2.1072 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2539   -0.0538    3.5174 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8558    1.6615    2.6991 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6387    1.0803    1.4551 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8872   -1.2574    0.4268 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4762   -1.5995    1.0384 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4043    0.1490   -1.2301 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3145   -1.3457   -1.5138 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2763    1.4435   -0.7776 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4583    0.5604   -2.2813 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1821   -0.9646   -1.3665 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5805    0.7363   -1.2274 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4159   -0.7033    1.2520 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0226    0.9268    1.0417 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6160   -0.6505    2.0580 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6959   -1.5456    0.4722 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5787    2.1058   -0.8018 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  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  1  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  6
  7 36  1  0
  8 37  1  0
  9 38  1  0
 10 39  1  0
 11 40  1  0
 12 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
 16 48  1  0
 17 49  1  0
 17 50  1  0
 18 51  1  0
 18 52  1  0
 19 53  1  0
 19 54  1  0
 20 55  1  0
 20 56  1  0
 23 57  1  0
M  END

  Mrv0541 02231220202D          

 23 22  0  0  1  0            999 V2000
   14.9543  -10.8804    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.2398  -17.0678    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.9543  -15.8303    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.9543  -10.0554    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   15.6687   -9.6428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3832  -10.0554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8109  -14.5928    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8109  -13.7678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0977   -9.6428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5254  -15.0053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0964  -13.3554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8121  -10.0554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5254  -15.8303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0964  -12.5304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0964  -10.8804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5267   -9.6428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2398  -16.2428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3820  -12.1179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3820  -11.2928    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2398   -9.6428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0964  -10.0554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5254  -10.0554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8109   -9.6428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  4  1  1  6  0  0  0
  2 17  1  0  0  0  0
  3 17  2  0  0  0  0
  4  5  1  0  0  0  0
  4 20  1  0  0  0  0
  5  6  1  0  0  0  0
  6  9  1  0  0  0  0
  7  8  1  0  0  0  0
  7 10  1  0  0  0  0
  8 11  1  0  0  0  0
  9 12  1  0  0  0  0
 10 13  1  0  0  0  0
 11 14  1  0  0  0  0
 12 16  1  0  0  0  0
 13 17  1  0  0  0  0
 14 18  1  0  0  0  0
 15 19  1  0  0  0  0
 15 21  1  0  0  0  0
 18 19  2  0  0  0  0
 20 22  2  0  0  0  0
 21 23  2  0  0  0  0
 22 23  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0005045

> <DATABASE_NAME>
hmdb

> <SMILES>
CCCCC[C@H](O)\C=C\C=C/C\C=C/CCCCCCC(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C20H34O3/c1-2-3-13-16-19(21)17-14-11-9-7-5-4-6-8-10-12-15-18-20(22)23/h4-5,9,11,14,17,19,21H,2-3,6-8,10,12-13,15-16,18H2,1H3,(H,22,23)/b5-4-,11-9-,17-14+/t19-/m0/s1

> <INCHI_KEY>
IUKXMNDGTWTNTP-OAHXIXLCSA-N

> <FORMULA>
C20H34O3

> <MOLECULAR_WEIGHT>
322.4822

> <EXACT_MASS>
322.250794954

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
39.47234114359038

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
6.20

> <JCHEM_LOGP>
5.718281400666667

> <ALOGPS_LOGS>
-5.55

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
17.795677863984817

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.885823836012873

> <JCHEM_PKA_STRONGEST_BASIC>
-1.5759706522580879

> <JCHEM_POLAR_SURFACE_AREA>
57.53

> <JCHEM_REFRACTIVITY>
100.3529

> <JCHEM_ROTATABLE_BOND_COUNT>
15

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
9.02e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
6-deoxy-L-sorbose

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0005045
     RDKit          3D
15(S)-Hydroxyeicosatrienoic acid
 57 56  0  0  0  0  0  0  0  0999 V2000
    8.4163    0.0569    0.4062 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3931   -0.2722   -0.6586 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7686    0.9614   -1.2769 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7692    0.5621   -2.3064 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6312   -0.2653   -1.8289 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7520    0.3518   -0.7934 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.5502    0.6458    0.3377 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7915   -0.6759   -0.3118 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7913   -0.3803    0.5324 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9197   -1.4222    0.9448 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0890   -1.2527    1.7684 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4273    0.0221    2.3502 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7057    0.6676    2.1340 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7449    0.3624    1.4236 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9455   -0.7997    0.5628 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3103   -0.4322   -0.8467 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4807    0.3657   -1.1416 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8563   -0.0349   -0.8133 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1174   -0.1454    0.6487 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5558   -0.5504    0.9449 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4687    0.4868    0.4576 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.7085    0.1847    0.4363 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1253    1.7535    0.0223 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.2367   -0.6257    1.2910 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.4339   -0.1100    0.0018 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2636    1.1023    0.7062 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9184   -0.7953   -1.5164 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6330   -0.9897   -0.3281 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5924    1.4978   -1.8427 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3962    1.6957   -0.5660 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3787    1.4399   -2.8611 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3165   -0.0543   -3.0671 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9522   -1.2814   -1.4954 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9794   -0.4603   -2.7298 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2617    1.2715   -1.1564 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6491   -0.1702    0.9033 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8933   -1.6797   -0.6396 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7219    0.6325    0.8322 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0836   -2.4608    0.5542 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6905   -2.1757    2.0521 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3892    0.7779    2.1072 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2539   -0.0538    3.5174 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8558    1.6615    2.6991 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6387    1.0803    1.4551 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8872   -1.2574    0.4268 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4762   -1.5995    1.0384 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4043    0.1490   -1.2301 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3145   -1.3457   -1.5138 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2763    1.4435   -0.7776 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4583    0.5604   -2.2813 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1821   -0.9646   -1.3665 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5805    0.7363   -1.2274 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4159   -0.7033    1.2520 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0226    0.9268    1.0417 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6160   -0.6505    2.0580 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6959   -1.5456    0.4722 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5787    2.1058   -0.8018 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  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  1  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  6
  7 36  1  0
  8 37  1  0
  9 38  1  0
 10 39  1  0
 11 40  1  0
 12 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
 16 48  1  0
 17 49  1  0
 17 50  1  0
 18 51  1  0
 18 52  1  0
 19 53  1  0
 19 54  1  0
 20 55  1  0
 20 56  1  0
 23 57  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0      27.915 -20.310   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      26.581 -31.860   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      27.915 -29.550   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      27.915 -18.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      29.248 -18.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      30.582 -18.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      23.914 -27.240   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      23.914 -25.700   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      31.916 -18.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      25.247 -28.010   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      22.580 -24.930   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      33.249 -18.770   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      25.247 -29.550   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      22.580 -23.390   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      22.580 -20.310   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      34.583 -18.000   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      26.581 -30.320   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      21.246 -22.620   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      21.246 -21.080   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      26.581 -18.000   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      22.580 -18.770   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      25.247 -18.770   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      23.914 -18.000   0.000  0.00  0.00           C+0
CONECT    1    4                                                            
CONECT    2   17                                                            
CONECT    3   17                                                            
CONECT    4    1    5   20                                                  
CONECT    5    4    6                                                       
CONECT    6    5    9                                                       
CONECT    7    8   10                                                       
CONECT    8    7   11                                                       
CONECT    9    6   12                                                       
CONECT   10    7   13                                                       
CONECT   11    8   14                                                       
CONECT   12    9   16                                                       
CONECT   13   10   17                                                       
CONECT   14   11   18                                                       
CONECT   15   19   21                                                       
CONECT   16   12                                                            
CONECT   17    2    3   13                                                  
CONECT   18   14   19                                                       
CONECT   19   15   18                                                       
CONECT   20    4   22                                                       
CONECT   21   15   23                                                       
CONECT   22   20   23                                                       
CONECT   23   21   22                                                       
MASTER        0    0    0    0    0    0    0    0   23    0   44    0
END

COMPND    HMDB0005045
HETATM    1  C1  UNL     1       8.416   0.057   0.406  1.00  0.00           C  
HETATM    2  C2  UNL     1       7.393  -0.272  -0.659  1.00  0.00           C  
HETATM    3  C3  UNL     1       6.769   0.961  -1.277  1.00  0.00           C  
HETATM    4  C4  UNL     1       5.769   0.562  -2.306  1.00  0.00           C  
HETATM    5  C5  UNL     1       4.631  -0.265  -1.829  1.00  0.00           C  
HETATM    6  C6  UNL     1       3.752   0.352  -0.793  1.00  0.00           C  
HETATM    7  O1  UNL     1       4.550   0.646   0.338  1.00  0.00           O  
HETATM    8  C7  UNL     1       2.791  -0.676  -0.312  1.00  0.00           C  
HETATM    9  C8  UNL     1       1.791  -0.380   0.532  1.00  0.00           C  
HETATM   10  C9  UNL     1       0.920  -1.422   0.945  1.00  0.00           C  
HETATM   11  C10 UNL     1      -0.089  -1.253   1.768  1.00  0.00           C  
HETATM   12  C11 UNL     1      -0.427   0.022   2.350  1.00  0.00           C  
HETATM   13  C12 UNL     1      -1.706   0.668   2.134  1.00  0.00           C  
HETATM   14  C13 UNL     1      -2.745   0.362   1.424  1.00  0.00           C  
HETATM   15  C14 UNL     1      -2.945  -0.800   0.563  1.00  0.00           C  
HETATM   16  C15 UNL     1      -3.310  -0.432  -0.847  1.00  0.00           C  
HETATM   17  C16 UNL     1      -4.481   0.366  -1.142  1.00  0.00           C  
HETATM   18  C17 UNL     1      -5.856  -0.035  -0.813  1.00  0.00           C  
HETATM   19  C18 UNL     1      -6.117  -0.145   0.649  1.00  0.00           C  
HETATM   20  C19 UNL     1      -7.556  -0.550   0.945  1.00  0.00           C  
HETATM   21  C20 UNL     1      -8.469   0.487   0.458  1.00  0.00           C  
HETATM   22  O2  UNL     1      -9.709   0.185   0.436  1.00  0.00           O  
HETATM   23  O3  UNL     1      -8.125   1.753   0.022  1.00  0.00           O  
HETATM   24  H1  UNL     1       8.237  -0.626   1.291  1.00  0.00           H  
HETATM   25  H2  UNL     1       9.434  -0.110   0.002  1.00  0.00           H  
HETATM   26  H3  UNL     1       8.264   1.102   0.706  1.00  0.00           H  
HETATM   27  H4  UNL     1       7.918  -0.795  -1.516  1.00  0.00           H  
HETATM   28  H5  UNL     1       6.633  -0.990  -0.328  1.00  0.00           H  
HETATM   29  H6  UNL     1       7.592   1.498  -1.843  1.00  0.00           H  
HETATM   30  H7  UNL     1       6.396   1.696  -0.566  1.00  0.00           H  
HETATM   31  H8  UNL     1       5.379   1.440  -2.861  1.00  0.00           H  
HETATM   32  H9  UNL     1       6.316  -0.054  -3.067  1.00  0.00           H  
HETATM   33  H10 UNL     1       4.952  -1.281  -1.495  1.00  0.00           H  
HETATM   34  H11 UNL     1       3.979  -0.460  -2.730  1.00  0.00           H  
HETATM   35  H12 UNL     1       3.262   1.271  -1.156  1.00  0.00           H  
HETATM   36  H13 UNL     1       4.649  -0.170   0.903  1.00  0.00           H  
HETATM   37  H14 UNL     1       2.893  -1.680  -0.640  1.00  0.00           H  
HETATM   38  H15 UNL     1       1.722   0.633   0.832  1.00  0.00           H  
HETATM   39  H16 UNL     1       1.084  -2.461   0.554  1.00  0.00           H  
HETATM   40  H17 UNL     1      -0.690  -2.176   2.052  1.00  0.00           H  
HETATM   41  H18 UNL     1       0.389   0.778   2.107  1.00  0.00           H  
HETATM   42  H19 UNL     1      -0.254  -0.054   3.517  1.00  0.00           H  
HETATM   43  H20 UNL     1      -1.856   1.662   2.699  1.00  0.00           H  
HETATM   44  H21 UNL     1      -3.639   1.080   1.455  1.00  0.00           H  
HETATM   45  H22 UNL     1      -1.887  -1.257   0.427  1.00  0.00           H  
HETATM   46  H23 UNL     1      -3.476  -1.599   1.038  1.00  0.00           H  
HETATM   47  H24 UNL     1      -2.404   0.149  -1.230  1.00  0.00           H  
HETATM   48  H25 UNL     1      -3.314  -1.346  -1.514  1.00  0.00           H  
HETATM   49  H26 UNL     1      -4.276   1.444  -0.778  1.00  0.00           H  
HETATM   50  H27 UNL     1      -4.458   0.560  -2.281  1.00  0.00           H  
HETATM   51  H28 UNL     1      -6.182  -0.965  -1.366  1.00  0.00           H  
HETATM   52  H29 UNL     1      -6.581   0.736  -1.227  1.00  0.00           H  
HETATM   53  H30 UNL     1      -5.416  -0.703   1.252  1.00  0.00           H  
HETATM   54  H31 UNL     1      -6.023   0.927   1.042  1.00  0.00           H  
HETATM   55  H32 UNL     1      -7.616  -0.650   2.058  1.00  0.00           H  
HETATM   56  H33 UNL     1      -7.696  -1.546   0.472  1.00  0.00           H  
HETATM   57  H34 UNL     1      -8.579   2.106  -0.802  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    8   35
CONECT    7   36
CONECT    8    9    9   37
CONECT    9   10   38
CONECT   10   11   11   39
CONECT   11   12   40
CONECT   12   13   41   42
CONECT   13   14   14   43
CONECT   14   15   44
CONECT   15   16   45   46
CONECT   16   17   47   48
CONECT   17   18   49   50
CONECT   18   19   51   52
CONECT   19   20   53   54
CONECT   20   21   55   56
CONECT   21   22   22   23
CONECT   23   57
END

HMDB0005045
     RDKit          3D
15(S)-Hydroxyeicosatrienoic acid
 57 56  0  0  0  0  0  0  0  0999 V2000
    8.4163    0.0569    0.4062 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3931   -0.2722   -0.6586 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7686    0.9614   -1.2769 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7692    0.5621   -2.3064 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6312   -0.2653   -1.8289 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7520    0.3518   -0.7934 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.5502    0.6458    0.3377 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7915   -0.6759   -0.3118 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7913   -0.3803    0.5324 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9197   -1.4222    0.9448 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0890   -1.2527    1.7684 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4273    0.0221    2.3502 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7057    0.6676    2.1340 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7449    0.3624    1.4236 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9455   -0.7997    0.5628 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3103   -0.4322   -0.8467 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4807    0.3657   -1.1416 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8563   -0.0349   -0.8133 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1174   -0.1454    0.6487 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5558   -0.5504    0.9449 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4687    0.4868    0.4576 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.7085    0.1847    0.4363 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1253    1.7535    0.0223 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.2367   -0.6257    1.2910 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.4339   -0.1100    0.0018 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2636    1.1023    0.7062 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9184   -0.7953   -1.5164 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6330   -0.9897   -0.3281 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5924    1.4978   -1.8427 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3962    1.6957   -0.5660 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3787    1.4399   -2.8611 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3165   -0.0543   -3.0671 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9522   -1.2814   -1.4954 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9794   -0.4603   -2.7298 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2617    1.2715   -1.1564 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6491   -0.1702    0.9033 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8933   -1.6797   -0.6396 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7219    0.6325    0.8322 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0836   -2.4608    0.5542 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6905   -2.1757    2.0521 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3892    0.7779    2.1072 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2539   -0.0538    3.5174 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8558    1.6615    2.6991 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6387    1.0803    1.4551 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8872   -1.2574    0.4268 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4762   -1.5995    1.0384 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4043    0.1490   -1.2301 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3145   -1.3457   -1.5138 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2763    1.4435   -0.7776 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4583    0.5604   -2.2813 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1821   -0.9646   -1.3665 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5805    0.7363   -1.2274 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4159   -0.7033    1.2520 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0226    0.9268    1.0417 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6160   -0.6505    2.0580 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6959   -1.5456    0.4722 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5787    2.1058   -0.8018 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  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  1  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  6
  7 36  1  0
  8 37  1  0
  9 38  1  0
 10 39  1  0
 11 40  1  0
 12 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
 16 48  1  0
 17 49  1  0
 17 50  1  0
 18 51  1  0
 18 52  1  0
 19 53  1  0
 19 54  1  0
 20 55  1  0
 20 56  1  0
 23 57  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(8Z,11Z,13E,15S)-15-Hydroxyicosatrienoic acid	ChEBI
15-HETrE	ChEBI
15-Hydroxy-(8Z,11Z,13E)-eicosatrienoic acid	ChEBI
15-Hydroxy-cis,cis,trans-8,11,13-eicosatrienoic acid	ChEBI
15-Hydroxyeicosatrienoic acid	ChEBI
15S-HETrE	ChEBI
15S-Hydroxy-8Z,11Z,13E-eicosatrienoic acid	ChEBI
(8Z,11Z,13E,15S)-15-Hydroxyicosatrienoate	Generator
15-Hydroxy-(8Z,11Z,13E)-eicosatrienoate	Generator
15-Hydroxy-cis,cis,trans-8,11,13-eicosatrienoate	Generator
15-Hydroxyeicosatrienoate	Generator
15S-Hydroxy-8Z,11Z,13E-eicosatrienoate	Generator
15(S)-Hydroxyeicosatrienoate	Generator

Chemical Formula

C₂₀H₃₄O₃

Average Molecular Weight

322.4822

Monoisotopic Molecular Weight

322.250794954

IUPAC Name

(8Z,11Z,13E,15S)-15-hydroxyicosa-8,11,13-trienoic acid

Traditional Name

6-deoxy-L-sorbose

CAS Registry Number

13-16-1

SMILES

CCCCC[C@H](O)\C=C\C=C/C\C=C/CCCCCCC(O)=O

InChI Identifier

InChI=1S/C20H34O3/c1-2-3-13-16-19(21)17-14-11-9-7-5-4-6-8-10-12-15-18-20(22)23/h4-5,9,11,14,17,19,21H,2-3,6-8,10,12-13,15-16,18H2,1H3,(H,22,23)/b5-4-,11-9-,17-14+/t19-/m0/s1

InChI Key

IUKXMNDGTWTNTP-OAHXIXLCSA-N

Chemical Taxonomy

Description

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

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Eicosanoids

Direct Parent

Hydroxyeicosatrienoic acids

Alternative Parents

Substituents

Hydroxyeicosatrienoic 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/hydroperoxyeicosatrienoic acids (LMFA03050007 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 20671299)

Cellular substructure

Membrane (HMDB: HMDB0005045)
Extracellular (HMDB: HMDB0005045)

Source

Exogenous

Exogenous (HMDB: HMDB0005045)

Food

Animal origin

Poultry

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

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

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

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

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

Equine

Horse (FooDB: FOOD00378)

Endogenous

Endogenous (HMDB: HMDB0005045)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.0009 g/L	ALOGPS
logP	6.2	ALOGPS
logP	5.72	ChemAxon
logS	-5.6	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	15	ChemAxon
Refractivity	100.35 m³·mol⁻¹	ChemAxon
Polarizability	39.47 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	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]+	187.45	31661259
DarkChem	[M-H]-	190.451	31661259
DeepCCS	[M+H]+	189.909	30932474
DeepCCS	[M-H]-	187.551	30932474
DeepCCS	[M-2H]-	220.437	30932474
DeepCCS	[M+Na]+	196.002	30932474
AllCCS	[M+H]+	188.4	32859911
AllCCS	[M+H-H2O]+	185.5	32859911
AllCCS	[M+NH4]+	191.0	32859911
AllCCS	[M+Na]+	191.7	32859911
AllCCS	[M-H]-	187.0	32859911
AllCCS	[M+Na-2H]-	188.9	32859911
AllCCS	[M+HCOO]-	191.1	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
15(S)-Hydroxyeicosatrienoic acid	CCCCC[C@H](O)\C=C\C=C/C\C=C/CCCCCCC(O)=O	4108.6	Standard polar	33892256
15(S)-Hydroxyeicosatrienoic acid	CCCCC[C@H](O)\C=C\C=C/C\C=C/CCCCCCC(O)=O	2432.0	Standard non polar	33892256
15(S)-Hydroxyeicosatrienoic acid	CCCCC[C@H](O)\C=C\C=C/C\C=C/CCCCCCC(O)=O	2604.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
15(S)-Hydroxyeicosatrienoic acid,1TMS,isomer #1	CCCCC[C@@H](/C=C/C=C\C/C=C\CCCCCCC(=O)O)O[Si](C)(C)C	2730.3	Semi standard non polar	33892256
15(S)-Hydroxyeicosatrienoic acid,1TMS,isomer #2	CCCCC[C@H](O)/C=C/C=C\C/C=C\CCCCCCC(=O)O[Si](C)(C)C	2646.7	Semi standard non polar	33892256
15(S)-Hydroxyeicosatrienoic acid,2TMS,isomer #1	CCCCC[C@@H](/C=C/C=C\C/C=C\CCCCCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C	2717.3	Semi standard non polar	33892256
15(S)-Hydroxyeicosatrienoic acid,1TBDMS,isomer #1	CCCCC[C@@H](/C=C/C=C\C/C=C\CCCCCCC(=O)O)O[Si](C)(C)C(C)(C)C	2979.9	Semi standard non polar	33892256
15(S)-Hydroxyeicosatrienoic acid,1TBDMS,isomer #2	CCCCC[C@H](O)/C=C/C=C\C/C=C\CCCCCCC(=O)O[Si](C)(C)C(C)(C)C	2889.0	Semi standard non polar	33892256
15(S)-Hydroxyeicosatrienoic acid,2TBDMS,isomer #1	CCCCC[C@@H](/C=C/C=C\C/C=C\CCCCCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3218.5	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 - 15(S)-Hydroxyeicosatrienoic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-0pi0-6592000000-9dc0f3f0bbc2de8a434d	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 15(S)-Hydroxyeicosatrienoic acid GC-MS (2 TMS) - 70eV, Positive	splash10-004i-9332200000-cf5f429c3867c843e3f2	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 15(S)-Hydroxyeicosatrienoic 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 - 15(S)-Hydroxyeicosatrienoic acid 10V, Positive-QTOF	splash10-0a4i-0059000000-a80d73087c4ff885f762	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 15(S)-Hydroxyeicosatrienoic acid 20V, Positive-QTOF	splash10-0a4i-4393000000-64b119d876007616dced	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 15(S)-Hydroxyeicosatrienoic acid 40V, Positive-QTOF	splash10-03kc-9630000000-2bff72917aba29b0568d	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 15(S)-Hydroxyeicosatrienoic acid 10V, Negative-QTOF	splash10-00di-0019000000-4c24ada22b9690dcb2fd	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 15(S)-Hydroxyeicosatrienoic acid 20V, Negative-QTOF	splash10-0fk9-2059000000-6a462b1cbfb1f2633ec2	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 15(S)-Hydroxyeicosatrienoic acid 40V, Negative-QTOF	splash10-0a4l-9130000000-973ff7b5957c59e99327	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 15(S)-Hydroxyeicosatrienoic acid 10V, Negative-QTOF	splash10-0fk9-0009000000-57568fa8a4085a5e528c	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 15(S)-Hydroxyeicosatrienoic acid 20V, Negative-QTOF	splash10-0uk9-1249000000-c0ee7a1e26de1f84a01c	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 15(S)-Hydroxyeicosatrienoic acid 40V, Negative-QTOF	splash10-0006-9140000000-a469f1131b8f8929c25e	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 15(S)-Hydroxyeicosatrienoic acid 10V, Positive-QTOF	splash10-0a4i-0459000000-12a2a03e81c41e9d9b57	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 15(S)-Hydroxyeicosatrienoic acid 20V, Positive-QTOF	splash10-052r-1953000000-ce7b9656736b3429c15a	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 15(S)-Hydroxyeicosatrienoic acid 40V, Positive-QTOF	splash10-067i-9600000000-dee10fd76962f5b5aae8	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane (predicted from logP)

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.000253 +/- 0.000018 uM	Adult (>18 years old)	Both	Normal	20671299	details
Blood	Detected and Quantified	0.000437 +/- 0.000028 uM	Adult (>18 years old)	Both	Normal	21359215	details
Blood	Detected and Quantified	0.000732 +/- 0.00045 uM	Adult (>18 years old)	Both	Normal	21359215	details
Blood	Detected and Quantified	0.000421 +/- 0.000015 uM	Adult (>18 years old)	Both	Normal	20671299	details

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

FDB023608

KNApSAcK ID

C00000182

Chemspider ID

4446269

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5283145

PDB ID

Not Available

ChEBI ID

88348

Food Biomarker Ontology

Not Available

VMH ID

CE2537

MarkerDB ID

Not Available

Good Scents ID

rw1797471

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Pham H, Banerjee T, Ziboh VA: Suppression of cyclooxygenase-2 overexpression by 15S-hydroxyeicosatrienoic acid in androgen-dependent prostatic adenocarcinoma cells. Int J Cancer. 2004 Aug 20;111(2):192-7. [PubMed:15197770 ]
Pham H, Banerjee T, Nalbandian GM, Ziboh VA: Activation of peroxisome proliferator-activated receptor (PPAR)-gamma by 15S-hydroxyeicosatrienoic acid parallels growth suppression of androgen-dependent prostatic adenocarcinoma cells. Cancer Lett. 2003 Jan 10;189(1):17-25. [PubMed:12445673 ]

Showing metabocard for 15(S)-Hydroxyeicosatrienoic acid (HMDB0005045)

MOL for HMDB0005045 (15(S)-Hydroxyeicosatrienoic acid)

3D MOL for HMDB0005045 (15(S)-Hydroxyeicosatrienoic acid)

3D SDF for HMDB0005045 (15(S)-Hydroxyeicosatrienoic acid)

3D-SDF for HMDB0005045 (15(S)-Hydroxyeicosatrienoic acid)

PDB for HMDB0005045 (15(S)-Hydroxyeicosatrienoic acid)

3D PDB for HMDB0005045 (15(S)-Hydroxyeicosatrienoic acid)

SMILES for HMDB0005045 (15(S)-Hydroxyeicosatrienoic acid)

INCHI for HMDB0005045 (15(S)-Hydroxyeicosatrienoic acid)

Structure for HMDB0005045 (15(S)-Hydroxyeicosatrienoic acid)

3D Structure for HMDB0005045 (15(S)-Hydroxyeicosatrienoic acid)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra