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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (24) Show 24 proteins XML

Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2006-08-14 00:24:46 UTC

Update Date

2022-03-07 02:49:21 UTC

HMDB ID

HMDB0004684

Secondary Accession Numbers

HMDB04684

Metabolite Identification

Common Name

11,12,15-THETA

Description

11,12,15-trihydroxyeicosatrienoic acid (11,12,15-THETA) is a metabolite of the 15-lipoxygenase (15-LO) pathway of arachidonic acid (AA). 11,12,15-THETA is an endothelium-derived relaxing factor. Acetylcholine stimulates AA release from membrane phospholipids of vascular endothelial cells (ECs). AA is released from phosphatidylcholine (PC) and phosphatidylethanolamine (PE) by phospholipase A2 (PLA2), or from phosphatidylinositol (PI) by phospholipase C (PLC) pathway. The diacylglycerol (DAG) lipase can convert DAG into 2-arachidonoylglycerol from which free AA can be released by monoacylglycerol (MAG) lipase or fatty acid amidohydrolase (FAAH). 11,12,15-THETA mediates the acetylcholine-induced vaso-relaxation, via activation of the K+ channels to hyperpolarize the smooth muscle membrane and induce relaxation. (PMID: 12907422 , 16024567 , 15388505 , 14622984 ).

Structure

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

HMDB0004684
     RDKit          3D
11,12,15-THETA
 59 58  0  0  0  0  0  0  0  0999 V2000
    7.9348   -1.1782   -0.6958 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3242   -0.2073    0.3010 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1112    0.4635   -0.3001 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5023    1.4179    0.6679 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0340    0.8294    1.9578 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9792   -0.2152    1.7986 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.3442   -1.3073    1.0596 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7284    0.4216    1.3337 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5899   -0.2655    1.3256 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3608    0.4028    0.8545 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5693    1.7750    0.7669 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0770   -0.1865   -0.5367 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1302    0.0263   -1.3939 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1261    0.5671   -1.0612 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5694    0.1586   -2.3897 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7416   -0.3438   -2.6616 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8702   -0.6327   -1.8082 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8528   -0.4154   -0.3942 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5974    0.3684    0.3438 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6342    1.1994   -0.2243 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9993    0.8945    0.2775 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5859   -0.4265    0.0383 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9929   -1.6151    0.6359 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0930   -1.6169    1.4864 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4437   -2.9045    0.2500 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1043   -1.8520   -1.0220 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3559   -0.6201   -1.5588 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.6989   -1.7651   -0.1441 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0527    0.5947    0.5422 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0322   -0.7940    1.1892 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4131   -0.2743   -0.7000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4695    1.0952   -1.1715 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1915    2.2675    0.9144 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6127    1.9228    0.2008 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6707    1.6893    2.5801 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8985    0.4277    2.5624 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7419   -0.6081    2.8335 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6328   -1.7475    0.5628 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7643    1.4511    1.0028 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6222   -1.2928    1.6691 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4610    0.2003    1.5439 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4238    2.1591    1.6599 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0826   -1.2481   -0.3997 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0530    0.8547   -1.9096 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8538    0.8778   -0.3274 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6214    1.5972   -1.2785 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8823    0.2695   -3.2692 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9181   -0.6006   -3.7384 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7446   -0.0700   -2.2446 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2228   -1.7141   -2.0529 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1041   -1.0105    0.1912 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4252    0.4246    1.4302 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6066    1.3482   -1.3264 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3810    2.2736    0.1419 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7199    1.6622   -0.1598 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0789    1.1079    1.3913 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6652   -0.3653    0.4272 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7698   -0.6080   -1.0675 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3795   -3.0227   -0.1040 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  1  0
 10 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  2  0
 23 25  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  2 29  1  0
  2 30  1  0
  3 31  1  0
  3 32  1  0
  4 33  1  0
  4 34  1  0
  5 35  1  0
  5 36  1  0
  6 37  1  1
  7 38  1  0
  8 39  1  0
  9 40  1  0
 10 41  1  0
 11 42  1  0
 12 43  1  0
 13 44  1  0
 14 45  1  0
 14 46  1  0
 15 47  1  0
 16 48  1  0
 17 49  1  0
 17 50  1  0
 18 51  1  0
 19 52  1  0
 20 53  1  0
 20 54  1  0
 21 55  1  0
 21 56  1  0
 22 57  1  0
 22 58  1  0
 25 59  1  0
M  END


  Mrv0541 02231219582D          

 25 24  0  0  1  0            999 V2000
   25.0087  -18.1034    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.8653  -20.1659    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.1507  -18.1034    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.4363  -24.2910    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.0073  -24.2910    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.7232  -19.3409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.4377  -18.9284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.0087  -18.9284    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   27.1522  -19.3409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.8653  -19.3409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.1507  -18.9284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.8666  -18.9284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.2942  -19.3409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.5797  -18.9284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.4363  -19.3409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.5812  -19.3409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.7218  -18.9284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0073  -19.3409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0073  -20.1659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0073  -21.8160    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0073  -22.6410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2928  -20.5785    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2928  -21.4035    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.7218  -23.0535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.7218  -23.8785    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  8  1  1  1  0  0  0
  2 10  1  0  0  0  0
  3 11  1  0  0  0  0
  4 25  1  0  0  0  0
  5 25  2  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  7  9  1  0  0  0  0
  8 13  1  0  0  0  0
  9 12  1  0  0  0  0
 10 11  1  0  0  0  0
 10 14  1  0  0  0  0
 11 15  1  0  0  0  0
 12 16  1  0  0  0  0
 13 14  2  0  0  0  0
 15 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 22  1  0  0  0  0
 20 21  1  0  0  0  0
 20 23  1  0  0  0  0
 21 24  1  0  0  0  0
 22 23  2  0  0  0  0
 24 25  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0004684

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C20H34O5/c1-2-3-9-12-17(21)15-16-19(23)18(22)13-10-7-5-4-6-8-11-14-20(24)25/h4,6-7,10,15-19,21-23H,2-3,5,8-9,11-14H2,1H3,(H,24,25)/b6-4-,10-7-,16-15+/t17-,18?,19?/m0/s1

> <INCHI_KEY>
PRMWQIVYOYCJQC-YZSNCDGGSA-N

> <FORMULA>
C20H34O5

> <MOLECULAR_WEIGHT>
354.481

> <EXACT_MASS>
354.240624198

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
40.44904647963837

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(5Z,8Z,13E,15S)-11,12,15-trihydroxyicosa-5,8,13-trienoic acid

> <ALOGPS_LOGP>
4.46

> <JCHEM_LOGP>
3.4125667266666655

> <ALOGPS_LOGS>
-3.83

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
13.610888110773573

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.819771839819723

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8471940047391477

> <JCHEM_POLAR_SURFACE_AREA>
97.99000000000001

> <JCHEM_REFRACTIVITY>
103.2299

> <JCHEM_ROTATABLE_BOND_COUNT>
15

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.25e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(5Z,8Z,13E,15S)-11,12,15-trihydroxyicosa-5,8,13-trienoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0004684
     RDKit          3D
11,12,15-THETA
 59 58  0  0  0  0  0  0  0  0999 V2000
    7.9348   -1.1782   -0.6958 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3242   -0.2073    0.3010 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1112    0.4635   -0.3001 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5023    1.4179    0.6679 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0340    0.8294    1.9578 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9792   -0.2152    1.7986 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.3442   -1.3073    1.0596 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7284    0.4216    1.3337 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5899   -0.2655    1.3256 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3608    0.4028    0.8545 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5693    1.7750    0.7669 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0770   -0.1865   -0.5367 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1302    0.0263   -1.3939 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1261    0.5671   -1.0612 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5694    0.1586   -2.3897 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7416   -0.3438   -2.6616 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8702   -0.6327   -1.8082 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8528   -0.4154   -0.3942 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5974    0.3684    0.3438 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6342    1.1994   -0.2243 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9993    0.8945    0.2775 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5859   -0.4265    0.0383 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9929   -1.6151    0.6359 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0930   -1.6169    1.4864 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4437   -2.9045    0.2500 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1043   -1.8520   -1.0220 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3559   -0.6201   -1.5588 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.6989   -1.7651   -0.1441 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0527    0.5947    0.5422 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0322   -0.7940    1.1892 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4131   -0.2743   -0.7000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4695    1.0952   -1.1715 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1915    2.2675    0.9144 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6127    1.9228    0.2008 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6707    1.6893    2.5801 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8985    0.4277    2.5624 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7419   -0.6081    2.8335 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6328   -1.7475    0.5628 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7643    1.4511    1.0028 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6222   -1.2928    1.6691 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4610    0.2003    1.5439 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4238    2.1591    1.6599 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0826   -1.2481   -0.3997 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0530    0.8547   -1.9096 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8538    0.8778   -0.3274 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6214    1.5972   -1.2785 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8823    0.2695   -3.2692 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9181   -0.6006   -3.7384 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7446   -0.0700   -2.2446 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2228   -1.7141   -2.0529 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1041   -1.0105    0.1912 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4252    0.4246    1.4302 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6066    1.3482   -1.3264 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3810    2.2736    0.1419 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7199    1.6622   -0.1598 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0789    1.1079    1.3913 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6652   -0.3653    0.4272 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7698   -0.6080   -1.0675 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3795   -3.0227   -0.1040 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  1  0
 10 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  2  0
 23 25  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  2 29  1  0
  2 30  1  0
  3 31  1  0
  3 32  1  0
  4 33  1  0
  4 34  1  0
  5 35  1  0
  5 36  1  0
  6 37  1  1
  7 38  1  0
  8 39  1  0
  9 40  1  0
 10 41  1  0
 11 42  1  0
 12 43  1  0
 13 44  1  0
 14 45  1  0
 14 46  1  0
 15 47  1  0
 16 48  1  0
 17 49  1  0
 17 50  1  0
 18 51  1  0
 19 52  1  0
 20 53  1  0
 20 54  1  0
 21 55  1  0
 21 56  1  0
 22 57  1  0
 22 58  1  0
 25 59  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      46.683 -33.793   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      42.682 -37.643   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      41.348 -33.793   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      40.014 -45.343   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0      37.347 -45.343   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      48.017 -36.103   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      49.350 -35.333   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      46.683 -35.333   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      50.684 -36.103   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      42.682 -36.103   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      41.348 -35.333   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      52.018 -35.333   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      45.349 -36.103   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      44.015 -35.333   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      40.014 -36.103   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      53.352 -36.103   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      38.681 -35.333   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      37.347 -36.103   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      37.347 -37.643   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      37.347 -40.723   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      37.347 -42.263   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      36.013 -38.413   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      36.013 -39.953   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      38.681 -43.033   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      38.681 -44.573   0.000  0.00  0.00           C+0
CONECT    1    8                                                            
CONECT    2   10                                                            
CONECT    3   11                                                            
CONECT    4   25                                                            
CONECT    5   25                                                            
CONECT    6    7    8                                                       
CONECT    7    6    9                                                       
CONECT    8    1    6   13                                                  
CONECT    9    7   12                                                       
CONECT   10    2   11   14                                                  
CONECT   11    3   10   15                                                  
CONECT   12    9   16                                                       
CONECT   13    8   14                                                       
CONECT   14   10   13                                                       
CONECT   15   11   17                                                       
CONECT   16   12                                                            
CONECT   17   15   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   22                                                       
CONECT   20   21   23                                                       
CONECT   21   20   24                                                       
CONECT   22   19   23                                                       
CONECT   23   20   22                                                       
CONECT   24   21   25                                                       
CONECT   25    4    5   24                                                  
MASTER        0    0    0    0    0    0    0    0   25    0   48    0
END

COMPND    HMDB0004684
HETATM    1  C1  UNL     1       7.935  -1.178  -0.696  1.00  0.00           C  
HETATM    2  C2  UNL     1       7.324  -0.207   0.301  1.00  0.00           C  
HETATM    3  C3  UNL     1       6.111   0.464  -0.300  1.00  0.00           C  
HETATM    4  C4  UNL     1       5.502   1.418   0.668  1.00  0.00           C  
HETATM    5  C5  UNL     1       5.034   0.829   1.958  1.00  0.00           C  
HETATM    6  C6  UNL     1       3.979  -0.215   1.799  1.00  0.00           C  
HETATM    7  O1  UNL     1       4.344  -1.307   1.060  1.00  0.00           O  
HETATM    8  C7  UNL     1       2.728   0.422   1.334  1.00  0.00           C  
HETATM    9  C8  UNL     1       1.590  -0.266   1.326  1.00  0.00           C  
HETATM   10  C9  UNL     1       0.361   0.403   0.855  1.00  0.00           C  
HETATM   11  O2  UNL     1       0.569   1.775   0.767  1.00  0.00           O  
HETATM   12  C10 UNL     1       0.077  -0.187  -0.537  1.00  0.00           C  
HETATM   13  O3  UNL     1       1.130   0.026  -1.394  1.00  0.00           O  
HETATM   14  C11 UNL     1      -1.126   0.567  -1.061  1.00  0.00           C  
HETATM   15  C12 UNL     1      -1.569   0.159  -2.390  1.00  0.00           C  
HETATM   16  C13 UNL     1      -2.742  -0.344  -2.662  1.00  0.00           C  
HETATM   17  C14 UNL     1      -3.870  -0.633  -1.808  1.00  0.00           C  
HETATM   18  C15 UNL     1      -3.853  -0.415  -0.394  1.00  0.00           C  
HETATM   19  C16 UNL     1      -4.597   0.368   0.344  1.00  0.00           C  
HETATM   20  C17 UNL     1      -5.634   1.199  -0.224  1.00  0.00           C  
HETATM   21  C18 UNL     1      -6.999   0.895   0.277  1.00  0.00           C  
HETATM   22  C19 UNL     1      -7.586  -0.426   0.038  1.00  0.00           C  
HETATM   23  C20 UNL     1      -6.993  -1.615   0.636  1.00  0.00           C  
HETATM   24  O4  UNL     1      -6.093  -1.617   1.486  1.00  0.00           O  
HETATM   25  O5  UNL     1      -7.444  -2.904   0.250  1.00  0.00           O  
HETATM   26  H1  UNL     1       7.104  -1.852  -1.022  1.00  0.00           H  
HETATM   27  H2  UNL     1       8.356  -0.620  -1.559  1.00  0.00           H  
HETATM   28  H3  UNL     1       8.699  -1.765  -0.144  1.00  0.00           H  
HETATM   29  H4  UNL     1       8.053   0.595   0.542  1.00  0.00           H  
HETATM   30  H5  UNL     1       7.032  -0.794   1.189  1.00  0.00           H  
HETATM   31  H6  UNL     1       5.413  -0.274  -0.700  1.00  0.00           H  
HETATM   32  H7  UNL     1       6.469   1.095  -1.171  1.00  0.00           H  
HETATM   33  H8  UNL     1       6.192   2.268   0.914  1.00  0.00           H  
HETATM   34  H9  UNL     1       4.613   1.923   0.201  1.00  0.00           H  
HETATM   35  H10 UNL     1       4.671   1.689   2.580  1.00  0.00           H  
HETATM   36  H11 UNL     1       5.898   0.428   2.562  1.00  0.00           H  
HETATM   37  H12 UNL     1       3.742  -0.608   2.834  1.00  0.00           H  
HETATM   38  H13 UNL     1       3.633  -1.747   0.563  1.00  0.00           H  
HETATM   39  H14 UNL     1       2.764   1.451   1.003  1.00  0.00           H  
HETATM   40  H15 UNL     1       1.622  -1.293   1.669  1.00  0.00           H  
HETATM   41  H16 UNL     1      -0.461   0.200   1.544  1.00  0.00           H  
HETATM   42  H17 UNL     1       0.424   2.159   1.660  1.00  0.00           H  
HETATM   43  H18 UNL     1      -0.083  -1.248  -0.400  1.00  0.00           H  
HETATM   44  H19 UNL     1       1.053   0.855  -1.910  1.00  0.00           H  
HETATM   45  H20 UNL     1      -1.854   0.878  -0.327  1.00  0.00           H  
HETATM   46  H21 UNL     1      -0.621   1.597  -1.279  1.00  0.00           H  
HETATM   47  H22 UNL     1      -0.882   0.269  -3.269  1.00  0.00           H  
HETATM   48  H23 UNL     1      -2.918  -0.601  -3.738  1.00  0.00           H  
HETATM   49  H24 UNL     1      -4.745  -0.070  -2.245  1.00  0.00           H  
HETATM   50  H25 UNL     1      -4.223  -1.714  -2.053  1.00  0.00           H  
HETATM   51  H26 UNL     1      -3.104  -1.010   0.191  1.00  0.00           H  
HETATM   52  H27 UNL     1      -4.425   0.425   1.430  1.00  0.00           H  
HETATM   53  H28 UNL     1      -5.607   1.348  -1.326  1.00  0.00           H  
HETATM   54  H29 UNL     1      -5.381   2.274   0.142  1.00  0.00           H  
HETATM   55  H30 UNL     1      -7.720   1.662  -0.160  1.00  0.00           H  
HETATM   56  H31 UNL     1      -7.079   1.108   1.391  1.00  0.00           H  
HETATM   57  H32 UNL     1      -8.665  -0.365   0.427  1.00  0.00           H  
HETATM   58  H33 UNL     1      -7.770  -0.608  -1.068  1.00  0.00           H  
HETATM   59  H34 UNL     1      -8.380  -3.023  -0.104  1.00  0.00           H  
CONECT    1    2   26   27   28
CONECT    2    3   29   30
CONECT    3    4   31   32
CONECT    4    5   33   34
CONECT    5    6   35   36
CONECT    6    7    8   37
CONECT    7   38
CONECT    8    9    9   39
CONECT    9   10   40
CONECT   10   11   12   41
CONECT   11   42
CONECT   12   13   14   43
CONECT   13   44
CONECT   14   15   45   46
CONECT   15   16   16   47
CONECT   16   17   48
CONECT   17   18   49   50
CONECT   18   19   19   51
CONECT   19   20   52
CONECT   20   21   53   54
CONECT   21   22   55   56
CONECT   22   23   57   58
CONECT   23   24   24   25
CONECT   25   59
END

HMDB0004684
     RDKit          3D
11,12,15-THETA
 59 58  0  0  0  0  0  0  0  0999 V2000
    7.9348   -1.1782   -0.6958 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3242   -0.2073    0.3010 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1112    0.4635   -0.3001 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5023    1.4179    0.6679 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0340    0.8294    1.9578 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9792   -0.2152    1.7986 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.3442   -1.3073    1.0596 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7284    0.4216    1.3337 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5899   -0.2655    1.3256 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3608    0.4028    0.8545 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5693    1.7750    0.7669 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0770   -0.1865   -0.5367 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1302    0.0263   -1.3939 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1261    0.5671   -1.0612 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5694    0.1586   -2.3897 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7416   -0.3438   -2.6616 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8702   -0.6327   -1.8082 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8528   -0.4154   -0.3942 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5974    0.3684    0.3438 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6342    1.1994   -0.2243 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9993    0.8945    0.2775 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5859   -0.4265    0.0383 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9929   -1.6151    0.6359 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0930   -1.6169    1.4864 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4437   -2.9045    0.2500 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1043   -1.8520   -1.0220 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3559   -0.6201   -1.5588 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.6989   -1.7651   -0.1441 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0527    0.5947    0.5422 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0322   -0.7940    1.1892 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4131   -0.2743   -0.7000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4695    1.0952   -1.1715 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1915    2.2675    0.9144 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6127    1.9228    0.2008 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6707    1.6893    2.5801 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8985    0.4277    2.5624 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7419   -0.6081    2.8335 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6328   -1.7475    0.5628 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7643    1.4511    1.0028 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6222   -1.2928    1.6691 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4610    0.2003    1.5439 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4238    2.1591    1.6599 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0826   -1.2481   -0.3997 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0530    0.8547   -1.9096 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8538    0.8778   -0.3274 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6214    1.5972   -1.2785 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8823    0.2695   -3.2692 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9181   -0.6006   -3.7384 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7446   -0.0700   -2.2446 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2228   -1.7141   -2.0529 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1041   -1.0105    0.1912 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4252    0.4246    1.4302 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6066    1.3482   -1.3264 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3810    2.2736    0.1419 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7199    1.6622   -0.1598 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0789    1.1079    1.3913 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6652   -0.3653    0.4272 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7698   -0.6080   -1.0675 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3795   -3.0227   -0.1040 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  1  0
 10 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  2  0
 23 25  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  2 29  1  0
  2 30  1  0
  3 31  1  0
  3 32  1  0
  4 33  1  0
  4 34  1  0
  5 35  1  0
  5 36  1  0
  6 37  1  1
  7 38  1  0
  8 39  1  0
  9 40  1  0
 10 41  1  0
 11 42  1  0
 12 43  1  0
 13 44  1  0
 14 45  1  0
 14 46  1  0
 15 47  1  0
 16 48  1  0
 17 49  1  0
 17 50  1  0
 18 51  1  0
 19 52  1  0
 20 53  1  0
 20 54  1  0
 21 55  1  0
 21 56  1  0
 22 57  1  0
 22 58  1  0
 25 59  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
11,12,15-Trihydroxyicosatrienoic acid	Kegg
(5Z,8Z,13E)-(15S)-11,12,15-Trihydroxyeicosa-5,8,12-trienoic acid	Kegg
(5Z,8Z,13E)-(15S)-11,12,15-Trihydroxyicosa-5,8,12-trienoic acid	Kegg
11,12,15-Trihydroxyicosatrienoate	Generator
(5Z,8Z,13E)-(15S)-11,12,15-Trihydroxyeicosa-5,8,12-trienoate	Generator
(5Z,8Z,13E)-(15S)-11,12,15-Trihydroxyicosa-5,8,12-trienoate	Generator
11,12,15-TriHETRE	HMDB
11,12,15S-Trihydroxy-5Z,8Z,13E-eicosatrienoate	HMDB
11,12,15S-Trihydroxy-5Z,8Z,13E-eicosatrienoic acid	HMDB

Chemical Formula

C₂₀H₃₄O₅

Average Molecular Weight

354.481

Monoisotopic Molecular Weight

354.240624198

IUPAC Name

(5Z,8Z,13E,15S)-11,12,15-trihydroxyicosa-5,8,13-trienoic acid

Traditional Name

(5Z,8Z,13E,15S)-11,12,15-trihydroxyicosa-5,8,13-trienoic acid

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C20H34O5/c1-2-3-9-12-17(21)15-16-19(23)18(22)13-10-7-5-4-6-8-11-14-20(24)25/h4,6-7,10,15-19,21-23H,2-3,5,8-9,11-14H2,1H3,(H,24,25)/b6-4-,10-7-,16-15+/t17-,18?,19?/m0/s1

InChI Key

PRMWQIVYOYCJQC-YZSNCDGGSA-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
Polyol
Organic oxide
Organic oxygen compound
Hydrocarbon derivative
Carbonyl group
Organooxygen compound
Alcohol
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

polyunsaturated fatty acid (CHEBI:34128 )
hydroxy fatty acid (CHEBI:34128 )
Hydroxy/hydroperoxyeicosatrienoic acids (C14782 )
Hydroxy/hydroperoxyeicosatrienoic acids (LMFA03050017 )

Ontology

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	0.052 g/L	ALOGPS
logP	4.46	ALOGPS
logP	3.41	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Acidic)	4.82	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	97.99 Å²	ChemAxon
Rotatable Bond Count	15	ChemAxon
Refractivity	103.23 m³·mol⁻¹	ChemAxon
Polarizability	40.45 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]+	193.57	31661259
DarkChem	[M-H]-	190.138	31661259
DeepCCS	[M+H]+	195.233	30932474
DeepCCS	[M-H]-	192.874	30932474
DeepCCS	[M-2H]-	226.287	30932474
DeepCCS	[M+Na]+	201.514	30932474
AllCCS	[M+H]+	195.9	32859911
AllCCS	[M+H-H2O]+	193.3	32859911
AllCCS	[M+NH4]+	198.3	32859911
AllCCS	[M+Na]+	199.0	32859911
AllCCS	[M-H]-	191.3	32859911
AllCCS	[M+Na-2H]-	193.3	32859911
AllCCS	[M+HCOO]-	195.7	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 × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022.	6.59 minutes	32390414
Predicted by Siyang on May 30, 2022	14.8159 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.98 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	48.1 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2726.1 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	223.4 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	171.3 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	188.9 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	295.5 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	649.8 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	494.1 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	129.6 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1337.5 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	555.0 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	1490.5 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	426.7 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	406.6 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	381.7 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	174.7 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	8.3 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
11,12,15-THETA	CCCCC[C@H](O)\C=C\C(O)C(O)C\C=C/C\C=C/CCCC(O)=O	4573.5	Standard polar	33892256
11,12,15-THETA	CCCCC[C@H](O)\C=C\C(O)C(O)C\C=C/C\C=C/CCCC(O)=O	2583.1	Standard non polar	33892256
11,12,15-THETA	CCCCC[C@H](O)\C=C\C(O)C(O)C\C=C/C\C=C/CCCC(O)=O	2796.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
11,12,15-THETA,1TMS,isomer #1	CCCCC[C@@H](/C=C/C(O)C(O)C/C=C\C/C=C\CCCC(=O)O)O[Si](C)(C)C	3020.5	Semi standard non polar	33892256
11,12,15-THETA,1TMS,isomer #2	CCCCC[C@H](O)/C=C/C(O[Si](C)(C)C)C(O)C/C=C\C/C=C\CCCC(=O)O	2989.6	Semi standard non polar	33892256
11,12,15-THETA,1TMS,isomer #3	CCCCC[C@H](O)/C=C/C(O)C(C/C=C\C/C=C\CCCC(=O)O)O[Si](C)(C)C	2987.2	Semi standard non polar	33892256
11,12,15-THETA,1TMS,isomer #4	CCCCC[C@H](O)/C=C/C(O)C(O)C/C=C\C/C=C\CCCC(=O)O[Si](C)(C)C	2914.6	Semi standard non polar	33892256
11,12,15-THETA,2TMS,isomer #1	CCCCC[C@@H](/C=C/C(O[Si](C)(C)C)C(O)C/C=C\C/C=C\CCCC(=O)O)O[Si](C)(C)C	2982.4	Semi standard non polar	33892256
11,12,15-THETA,2TMS,isomer #2	CCCCC[C@@H](/C=C/C(O)C(C/C=C\C/C=C\CCCC(=O)O)O[Si](C)(C)C)O[Si](C)(C)C	2994.7	Semi standard non polar	33892256
11,12,15-THETA,2TMS,isomer #3	CCCCC[C@@H](/C=C/C(O)C(O)C/C=C\C/C=C\CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C	2928.0	Semi standard non polar	33892256
11,12,15-THETA,2TMS,isomer #4	CCCCC[C@H](O)/C=C/C(O[Si](C)(C)C)C(C/C=C\C/C=C\CCCC(=O)O)O[Si](C)(C)C	2986.9	Semi standard non polar	33892256
11,12,15-THETA,2TMS,isomer #5	CCCCC[C@H](O)/C=C/C(O[Si](C)(C)C)C(O)C/C=C\C/C=C\CCCC(=O)O[Si](C)(C)C	2916.7	Semi standard non polar	33892256
11,12,15-THETA,2TMS,isomer #6	CCCCC[C@H](O)/C=C/C(O)C(C/C=C\C/C=C\CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C	2914.4	Semi standard non polar	33892256
11,12,15-THETA,3TMS,isomer #1	CCCCC[C@@H](/C=C/C(O[Si](C)(C)C)C(C/C=C\C/C=C\CCCC(=O)O)O[Si](C)(C)C)O[Si](C)(C)C	2939.5	Semi standard non polar	33892256
11,12,15-THETA,3TMS,isomer #2	CCCCC[C@@H](/C=C/C(O[Si](C)(C)C)C(O)C/C=C\C/C=C\CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C	2876.3	Semi standard non polar	33892256
11,12,15-THETA,3TMS,isomer #3	CCCCC[C@@H](/C=C/C(O)C(C/C=C\C/C=C\CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C)O[Si](C)(C)C	2886.0	Semi standard non polar	33892256
11,12,15-THETA,3TMS,isomer #4	CCCCC[C@H](O)/C=C/C(O[Si](C)(C)C)C(C/C=C\C/C=C\CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C	2895.1	Semi standard non polar	33892256
11,12,15-THETA,4TMS,isomer #1	CCCCC[C@@H](/C=C/C(O[Si](C)(C)C)C(C/C=C\C/C=C\CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C)O[Si](C)(C)C	2852.6	Semi standard non polar	33892256
11,12,15-THETA,1TBDMS,isomer #1	CCCCC[C@@H](/C=C/C(O)C(O)C/C=C\C/C=C\CCCC(=O)O)O[Si](C)(C)C(C)(C)C	3252.5	Semi standard non polar	33892256
11,12,15-THETA,1TBDMS,isomer #2	CCCCC[C@H](O)/C=C/C(O[Si](C)(C)C(C)(C)C)C(O)C/C=C\C/C=C\CCCC(=O)O	3241.9	Semi standard non polar	33892256
11,12,15-THETA,1TBDMS,isomer #3	CCCCC[C@H](O)/C=C/C(O)C(C/C=C\C/C=C\CCCC(=O)O)O[Si](C)(C)C(C)(C)C	3235.6	Semi standard non polar	33892256
11,12,15-THETA,1TBDMS,isomer #4	CCCCC[C@H](O)/C=C/C(O)C(O)C/C=C\C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C	3171.6	Semi standard non polar	33892256
11,12,15-THETA,2TBDMS,isomer #1	CCCCC[C@@H](/C=C/C(O[Si](C)(C)C(C)(C)C)C(O)C/C=C\C/C=C\CCCC(=O)O)O[Si](C)(C)C(C)(C)C	3437.8	Semi standard non polar	33892256
11,12,15-THETA,2TBDMS,isomer #2	CCCCC[C@@H](/C=C/C(O)C(C/C=C\C/C=C\CCCC(=O)O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3444.3	Semi standard non polar	33892256
11,12,15-THETA,2TBDMS,isomer #3	CCCCC[C@@H](/C=C/C(O)C(O)C/C=C\C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3416.6	Semi standard non polar	33892256
11,12,15-THETA,2TBDMS,isomer #4	CCCCC[C@H](O)/C=C/C(O[Si](C)(C)C(C)(C)C)C(C/C=C\C/C=C\CCCC(=O)O)O[Si](C)(C)C(C)(C)C	3432.1	Semi standard non polar	33892256
11,12,15-THETA,2TBDMS,isomer #5	CCCCC[C@H](O)/C=C/C(O[Si](C)(C)C(C)(C)C)C(O)C/C=C\C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C	3399.6	Semi standard non polar	33892256
11,12,15-THETA,2TBDMS,isomer #6	CCCCC[C@H](O)/C=C/C(O)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	3389.1	Semi standard non polar	33892256
11,12,15-THETA,3TBDMS,isomer #1	CCCCC[C@@H](/C=C/C(O[Si](C)(C)C(C)(C)C)C(C/C=C\C/C=C\CCCC(=O)O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3619.0	Semi standard non polar	33892256
11,12,15-THETA,3TBDMS,isomer #2	CCCCC[C@@H](/C=C/C(O[Si](C)(C)C(C)(C)C)C(O)C/C=C\C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3609.9	Semi standard non polar	33892256
11,12,15-THETA,3TBDMS,isomer #3	CCCCC[C@@H](/C=C/C(O)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)O[Si](C)(C)C(C)(C)C	3627.6	Semi standard non polar	33892256
11,12,15-THETA,3TBDMS,isomer #4	CCCCC[C@H](O)/C=C/C(O[Si](C)(C)C(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	3580.8	Semi standard non polar	33892256
11,12,15-THETA,4TBDMS,isomer #1	CCCCC[C@@H](/C=C/C(O[Si](C)(C)C(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)O[Si](C)(C)C(C)(C)C	3768.2	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 - 11,12,15-THETA GC-MS (Non-derivatized) - 70eV, Positive	splash10-000j-6923000000-729d8425f6b7961f12d6	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 11,12,15-THETA GC-MS (4 TMS) - 70eV, Positive	splash10-004i-9114245000-a9570b215fa6eaa9ff8c	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 11,12,15-THETA 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 - 11,12,15-THETA 10V, Positive-QTOF	splash10-00kr-0109000000-ab120d0eda68ea718566	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 11,12,15-THETA 20V, Positive-QTOF	splash10-066r-2914000000-0b5d4d8637219b27e389	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 11,12,15-THETA 40V, Positive-QTOF	splash10-0abc-9720000000-6f9ba40124a0e432ec2a	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 11,12,15-THETA 10V, Negative-QTOF	splash10-0udi-0009000000-2fe2fc467f93d0346dcd	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 11,12,15-THETA 20V, Negative-QTOF	splash10-0k9i-1926000000-cebc50fd199b4b5d0e57	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 11,12,15-THETA 40V, Negative-QTOF	splash10-0a4i-8910000000-87e98db32bedae5d986e	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 11,12,15-THETA 10V, Positive-QTOF	splash10-00kr-0029000000-ebef111dafd7c78d37ac	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 11,12,15-THETA 20V, Positive-QTOF	splash10-014i-4569000000-4dc08f53204dfc55a344	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 11,12,15-THETA 40V, Positive-QTOF	splash10-0apl-9510000000-2862ca5a79b8eded3e16	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 11,12,15-THETA 10V, Negative-QTOF	splash10-0udi-0009000000-cbb73f896579bb3935fd	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 11,12,15-THETA 20V, Negative-QTOF	splash10-0f79-1649000000-07299e0617da708c9b9a	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 11,12,15-THETA 40V, Negative-QTOF	splash10-052b-9651000000-4bdcfd2275713a32e906	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Name	SMPDB/PathBank	KEGG
Arachidonic Acid Metabolism
Leukotriene C4 Synthesis Deficiency		Not Available
Piroxicam Action Pathway		Not Available
Acetylsalicylic Acid Action Pathway		Not Available
Etodolac Action Pathway		Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	<0.0001 uM	Adult (>18 years old)	Both	Normal	21359215	details
Blood	Detected and Quantified	<0.0001 uM	Adult (>18 years old)	Both	Normal	21359215	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

FDB023403

KNApSAcK ID

Not Available

Chemspider ID

10128338

KEGG Compound ID

C14782

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11954043

PDB ID

Not Available

ChEBI ID

34128

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

Campbell WB, Spitzbarth N, Gauthier KM, Pfister SL: 11,12,15-Trihydroxyeicosatrienoic acid mediates ACh-induced relaxations in rabbit aorta. Am J Physiol Heart Circ Physiol. 2003 Dec;285(6):H2648-56. Epub 2003 Aug 7. [PubMed:12907422 ]
Tang X, Edwards EM, Holmes BB, Falck JR, Campbell WB: Role of phospholipase C and diacylglyceride lipase pathway in arachidonic acid release and acetylcholine-induced vascular relaxation in rabbit aorta. Am J Physiol Heart Circ Physiol. 2006 Jan;290(1):H37-45. Epub 2005 Jul 15. [PubMed:16024567 ]
Zhang DX, Gauthier KM, Chawengsub Y, Holmes BB, Campbell WB: Cyclooxygenase- and lipoxygenase-dependent relaxation to arachidonic acid in rabbit small mesenteric arteries. Am J Physiol Heart Circ Physiol. 2005 Jan;288(1):H302-9. Epub 2004 Sep 23. [PubMed:15388505 ]
Pfister SL, Spitzbarth N, Zeldin DC, Lafite P, Mansuy D, Campbell WB: Rabbit aorta converts 15-HPETE to trihydroxyeicosatrienoic acids: potential role of cytochrome P450. Arch Biochem Biophys. 2003 Dec 1;420(1):142-52. [PubMed:14622984 ]

Only showing the first 10 proteins. There are 24 proteins in total.

Show all enzymes and transporters

Enzymes

Enzyme Details

1. Cytochrome P450 3A4

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide.
Gene Name:: CYP3A4
Uniprot ID:: P08684
Molecular weight:: 57255.585

Enzyme Details

2. Cytochrome P450 2C9

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. This enzyme contributes to the wide pharmacokinetics variability of the metabolism of drugs such as S-warfarin, diclofenac, phenytoin, tolbutamide and losartan.
Gene Name:: CYP2C9
Uniprot ID:: P11712
Molecular weight:: 55627.365

Enzyme Details

3. Cytochrome P450 2C19

General function:: Involved in monooxygenase activity
Specific function:: Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and imipramine.
Gene Name:: CYP2C19
Uniprot ID:: P33261
Molecular weight:: 55944.565

Enzyme Details

4. Cytochrome P450 2E1

General function:: Involved in monooxygenase activity
Specific function:: Metabolizes several precarcinogens, drugs, and solvents to reactive metabolites. Inactivates a number of drugs and xenobiotics and also bioactivates many xenobiotic substrates to their hepatotoxic or carcinogenic forms.
Gene Name:: CYP2E1
Uniprot ID:: P05181
Molecular weight:: 56848.42

Enzyme Details

5. Cytochrome P450 3A43

General function:: Involved in monooxygenase activity
Specific function:: Exhibits low testosterone 6-beta-hydroxylase activity.
Gene Name:: CYP3A43
Uniprot ID:: Q9HB55
Molecular weight:: 57756.285

Enzyme Details

6. Cytochrome P450 1B1

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Participates in the metabolism of an as-yet-unknown biologically active molecule that is a participant in eye development.
Gene Name:: CYP1B1
Uniprot ID:: Q16678
Molecular weight:: 60845.33

Enzyme Details

7. Cytochrome P450 2C18

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics.
Gene Name:: CYP2C18
Uniprot ID:: P33260
Molecular weight:: 55710.075

Enzyme Details

8. Cytochrome P450 2F1

General function:: Secondary metabolites biosynthesis, transport and catabolism
Specific function:: May be involved in the metabolism of various pneumotoxicants including naphthalene. Is able to dealkylate ethoxycoumarin, propoxycoumarin, and pentoxyresorufin but possesses no activity toward ethoxyresorufin and only trace dearylation activity toward benzyloxyresorufin. Bioactivates 3-methylindole (3MI) by dehydrogenation to the putative electrophile 3-methylene-indolenine.
Gene Name:: CYP2F1
Uniprot ID:: P24903
Molecular weight:: 55500.64

Enzyme Details

9. Cytochrome P450 4X1

General function:: Involved in monooxygenase activity
Specific function:: Not Available
Gene Name:: CYP4X1
Uniprot ID:: Q8N118
Molecular weight:: 58874.62

Enzyme Details

10. Cytochrome P450 2B6

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,4-cineole 2-exo-monooxygenase.
Gene Name:: CYP2B6
Uniprot ID:: P20813
Molecular weight:: 56277.81

Only showing the first 10 proteins. There are 24 proteins in total.

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Showing metabocard for 11,12,15-THETA (HMDB0004684)

MOL for HMDB0004684 (11,12,15-THETA)

3D MOL for HMDB0004684 (11,12,15-THETA)

3D SDF for HMDB0004684 (11,12,15-THETA)

3D-SDF for HMDB0004684 (11,12,15-THETA)

PDB for HMDB0004684 (11,12,15-THETA)

3D PDB for HMDB0004684 (11,12,15-THETA)

SMILES for HMDB0004684 (11,12,15-THETA)

INCHI for HMDB0004684 (11,12,15-THETA)

Structure for HMDB0004684 (11,12,15-THETA)

3D Structure for HMDB0004684 (11,12,15-THETA)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes