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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

Expected but not Quantified

Creation Date

2006-08-14 00:42:32 UTC

Update Date

2022-03-07 02:49:21 UTC

HMDB ID

HMDB0004694

Secondary Accession Numbers

HMDB04694

Metabolite Identification

Common Name

11,14,15-THETA

Description

11,14,15-trihydroxyeicosatrienoic acid (11,14,15-THETA) is a metabolite of the 15-lipoxygenase (15-LO) pathway of arachidonic acid (AA). Increased amounts of 11,14,15-THETA are synthesized in subacute hypoxia. Prolonged exposure to reduced PO2 activates 15-LO in small pulmonary arteries (PA); activation of 15-LO is associated with translocation of the enzyme from the cytosol to membrane. 11,14,15-THETA is an endothelium-derived relaxing factor. (PMID: 12690037 , 9812980 , 15388505 , 14622984 ).

Structure

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

HMDB0004694
     RDKit          3D
11,14,15-THETA
 59 58  0  0  0  0  0  0  0  0999 V2000
   -5.9182   -0.9525   -2.5758 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0047    0.4766   -2.1584 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8679    0.8913   -1.2510 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8393    0.0683    0.0261 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6681    0.5877    0.8252 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5392   -0.1300    2.1172 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6582   -0.0142    2.9310 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0548   -1.5535    1.9590 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0260   -2.3902    1.4155 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9085   -1.5679    1.0161 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6667   -1.6631    1.4532 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5208   -1.6823    0.5560 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6611   -1.5670    1.3397 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4413   -0.4734   -0.4031 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4271    0.7492    0.3850 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2138    1.7699    0.4063 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3926    2.0006   -0.3950 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7917    1.0681   -1.4236 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8958    0.3495   -1.4823 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9084    0.4465   -0.4008 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1789    0.9310   -1.0501 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2615    1.0779   -0.0408 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6181   -0.1753    0.6078 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1666   -1.3106    0.3648 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5877   -0.1137    1.6344 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5915   -1.1098   -3.4498 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2950   -1.6561   -1.7803 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9076   -1.2410   -2.9216 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9823    0.6417   -1.6702 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9725    1.1307   -3.0454 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9469    1.9537   -0.9613 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8923    0.7331   -1.7506 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6357   -0.9957   -0.2886 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7506    0.1529    0.6269 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7158    0.5120    0.2578 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8161    1.6770    1.0560 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7200    0.4149    2.6989 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1556   -0.8598    2.8753 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7773   -1.9989    2.9436 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6320   -3.1420    0.9128 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0937   -1.4994   -0.0385 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5365   -1.7301    2.5327 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5637   -2.6183   -0.0089 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5307   -1.0469    2.1542 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2040   -0.6533   -1.1237 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5452   -0.5351   -0.9468 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4566    0.7797    1.1086 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9193    2.5677    1.1549 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1909    3.0108   -0.9565 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2055    2.3289    0.3084 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1028    0.9724   -2.3001 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0758   -0.3328   -2.3406 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6080    1.0708    0.4487 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0723   -0.6221   -0.0416 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4379    0.2424   -1.8823 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0359    1.9321   -1.5349 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1207    1.5738   -0.5520 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8926    1.7885    0.7462 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.5495   -0.2648    1.3303 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  1  0
  8 10  1  0
 10 11  2  0
 11 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  0
  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  0  0            999 V2000
   24.1580  -18.9825    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.8726  -21.0450    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.0160  -18.9825    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.7305  -25.1701    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.1595  -25.1701    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.4436  -20.2200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.1580  -19.8075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.7291  -19.8075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.0147  -20.2200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.8726  -20.2200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3001  -19.8075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.5871  -19.8075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5856  -20.2200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.3015  -20.2200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.0160  -19.8075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.7305  -20.2200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.4450  -19.8075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.1595  -22.6951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.1595  -20.2200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.1595  -23.5201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.1595  -21.0450    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.8739  -22.2826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.8739  -21.4576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.4450  -23.9326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.4450  -24.7576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  7  1  0  0  0  0
  2 10  1  0  0  0  0
  3 15  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 10  1  0  0  0  0
  8  9  1  0  0  0  0
  9 11  1  0  0  0  0
 10 12  1  0  0  0  0
 11 13  1  0  0  0  0
 12 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 19  2  0  0  0  0
 18 20  1  0  0  0  0
 18 22  1  0  0  0  0
 19 21  1  0  0  0  0
 20 24  1  0  0  0  0
 21 23  1  0  0  0  0
 22 23  2  0  0  0  0
 24 25  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0004694

> <DATABASE_NAME>
hmdb

> <SMILES>
CCCCCC(O)C(O)\C=C\C(O)C\C=C/C\C=C/CCCC(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C20H34O5/c1-2-3-9-13-18(22)19(23)16-15-17(21)12-10-7-5-4-6-8-11-14-20(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+

> <INCHI_KEY>
YCFPVUKKIWMCJK-LTCHCNGXSA-N

> <FORMULA>
C20H34O5

> <MOLECULAR_WEIGHT>
354.481

> <EXACT_MASS>
354.240624198

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
41.29357161148917

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(5Z,8Z,12E)-11,14,15-trihydroxyicosa-5,8,12-trienoic acid

> <ALOGPS_LOGP>
4.47

> <JCHEM_LOGP>
3.4125667266666655

> <ALOGPS_LOGS>
-3.82

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
13.632888231797587

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.819771839854425

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8712415624713454

> <JCHEM_POLAR_SURFACE_AREA>
97.99000000000001

> <JCHEM_REFRACTIVITY>
103.2299

> <JCHEM_ROTATABLE_BOND_COUNT>
15

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.32e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(5Z,8Z,12E)-11,14,15-trihydroxyicosa-5,8,12-trienoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0004694
     RDKit          3D
11,14,15-THETA
 59 58  0  0  0  0  0  0  0  0999 V2000
   -5.9182   -0.9525   -2.5758 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0047    0.4766   -2.1584 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8679    0.8913   -1.2510 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8393    0.0683    0.0261 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6681    0.5877    0.8252 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5392   -0.1300    2.1172 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6582   -0.0142    2.9310 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0548   -1.5535    1.9590 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0260   -2.3902    1.4155 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9085   -1.5679    1.0161 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6667   -1.6631    1.4532 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5208   -1.6823    0.5560 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6611   -1.5670    1.3397 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4413   -0.4734   -0.4031 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4271    0.7492    0.3850 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2138    1.7699    0.4063 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3926    2.0006   -0.3950 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7917    1.0681   -1.4236 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8958    0.3495   -1.4823 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9084    0.4465   -0.4008 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1789    0.9310   -1.0501 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2615    1.0779   -0.0408 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6181   -0.1753    0.6078 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1666   -1.3106    0.3648 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5877   -0.1137    1.6344 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5915   -1.1098   -3.4498 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2950   -1.6561   -1.7803 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9076   -1.2410   -2.9216 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9823    0.6417   -1.6702 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9725    1.1307   -3.0454 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9469    1.9537   -0.9613 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8923    0.7331   -1.7506 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6357   -0.9957   -0.2886 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7506    0.1529    0.6269 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7158    0.5120    0.2578 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8161    1.6770    1.0560 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7200    0.4149    2.6989 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1556   -0.8598    2.8753 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7773   -1.9989    2.9436 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6320   -3.1420    0.9128 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0937   -1.4994   -0.0385 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5365   -1.7301    2.5327 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5637   -2.6183   -0.0089 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5307   -1.0469    2.1542 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2040   -0.6533   -1.1237 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5452   -0.5351   -0.9468 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4566    0.7797    1.1086 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9193    2.5677    1.1549 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1909    3.0108   -0.9565 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2055    2.3289    0.3084 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1028    0.9724   -2.3001 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0758   -0.3328   -2.3406 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6080    1.0708    0.4487 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0723   -0.6221   -0.0416 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4379    0.2424   -1.8823 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0359    1.9321   -1.5349 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1207    1.5738   -0.5520 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8926    1.7885    0.7462 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.5495   -0.2648    1.3303 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  1  0
  8 10  1  0
 10 11  2  0
 11 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  0
  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      45.095 -35.434   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      46.429 -39.284   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      50.430 -35.434   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      51.764 -46.984   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0      54.431 -46.984   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      43.761 -37.744   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      45.095 -36.974   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      42.428 -36.974   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      41.094 -37.744   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      46.429 -37.744   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      39.760 -36.974   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      47.763 -36.974   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      38.426 -37.744   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      49.096 -37.744   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      50.430 -36.974   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      51.764 -37.744   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      53.097 -36.974   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      54.431 -42.364   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      54.431 -37.744   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      54.431 -43.904   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      54.431 -39.284   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      55.765 -41.594   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      55.765 -40.054   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      53.097 -44.674   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      53.097 -46.214   0.000  0.00  0.00           C+0
CONECT    1    7                                                            
CONECT    2   10                                                            
CONECT    3   15                                                            
CONECT    4   25                                                            
CONECT    5   25                                                            
CONECT    6    7    8                                                       
CONECT    7    1    6   10                                                  
CONECT    8    6    9                                                       
CONECT    9    8   11                                                       
CONECT   10    2    7   12                                                  
CONECT   11    9   13                                                       
CONECT   12   10   14                                                       
CONECT   13   11                                                            
CONECT   14   12   15                                                       
CONECT   15    3   14   16                                                  
CONECT   16   15   17                                                       
CONECT   17   16   19                                                       
CONECT   18   20   22                                                       
CONECT   19   17   21                                                       
CONECT   20   18   24                                                       
CONECT   21   19   23                                                       
CONECT   22   18   23                                                       
CONECT   23   21   22                                                       
CONECT   24   20   25                                                       
CONECT   25    4    5   24                                                  
MASTER        0    0    0    0    0    0    0    0   25    0   48    0
END

COMPND    HMDB0004694
HETATM    1  C1  UNL     1      -5.918  -0.952  -2.576  1.00  0.00           C  
HETATM    2  C2  UNL     1      -6.005   0.477  -2.158  1.00  0.00           C  
HETATM    3  C3  UNL     1      -4.868   0.891  -1.251  1.00  0.00           C  
HETATM    4  C4  UNL     1      -4.839   0.068   0.026  1.00  0.00           C  
HETATM    5  C5  UNL     1      -3.668   0.588   0.825  1.00  0.00           C  
HETATM    6  C6  UNL     1      -3.539  -0.130   2.117  1.00  0.00           C  
HETATM    7  O1  UNL     1      -4.658  -0.014   2.931  1.00  0.00           O  
HETATM    8  C7  UNL     1      -3.055  -1.553   1.959  1.00  0.00           C  
HETATM    9  O2  UNL     1      -4.026  -2.390   1.415  1.00  0.00           O  
HETATM   10  C8  UNL     1      -1.908  -1.568   1.016  1.00  0.00           C  
HETATM   11  C9  UNL     1      -0.667  -1.663   1.453  1.00  0.00           C  
HETATM   12  C10 UNL     1       0.521  -1.682   0.556  1.00  0.00           C  
HETATM   13  O3  UNL     1       1.661  -1.567   1.340  1.00  0.00           O  
HETATM   14  C11 UNL     1       0.441  -0.473  -0.403  1.00  0.00           C  
HETATM   15  C12 UNL     1       0.427   0.749   0.385  1.00  0.00           C  
HETATM   16  C13 UNL     1       1.214   1.770   0.406  1.00  0.00           C  
HETATM   17  C14 UNL     1       2.393   2.001  -0.395  1.00  0.00           C  
HETATM   18  C15 UNL     1       2.792   1.068  -1.424  1.00  0.00           C  
HETATM   19  C16 UNL     1       3.896   0.350  -1.482  1.00  0.00           C  
HETATM   20  C17 UNL     1       4.908   0.447  -0.401  1.00  0.00           C  
HETATM   21  C18 UNL     1       6.179   0.931  -1.050  1.00  0.00           C  
HETATM   22  C19 UNL     1       7.262   1.078  -0.041  1.00  0.00           C  
HETATM   23  C20 UNL     1       7.618  -0.175   0.608  1.00  0.00           C  
HETATM   24  O4  UNL     1       7.167  -1.311   0.365  1.00  0.00           O  
HETATM   25  O5  UNL     1       8.588  -0.114   1.634  1.00  0.00           O  
HETATM   26  H1  UNL     1      -6.592  -1.110  -3.450  1.00  0.00           H  
HETATM   27  H2  UNL     1      -6.295  -1.656  -1.780  1.00  0.00           H  
HETATM   28  H3  UNL     1      -4.908  -1.241  -2.922  1.00  0.00           H  
HETATM   29  H4  UNL     1      -6.982   0.642  -1.670  1.00  0.00           H  
HETATM   30  H5  UNL     1      -5.972   1.131  -3.045  1.00  0.00           H  
HETATM   31  H6  UNL     1      -4.947   1.954  -0.961  1.00  0.00           H  
HETATM   32  H7  UNL     1      -3.892   0.733  -1.751  1.00  0.00           H  
HETATM   33  H8  UNL     1      -4.636  -0.996  -0.289  1.00  0.00           H  
HETATM   34  H9  UNL     1      -5.751   0.153   0.627  1.00  0.00           H  
HETATM   35  H10 UNL     1      -2.716   0.512   0.258  1.00  0.00           H  
HETATM   36  H11 UNL     1      -3.816   1.677   1.056  1.00  0.00           H  
HETATM   37  H12 UNL     1      -2.720   0.415   2.699  1.00  0.00           H  
HETATM   38  H13 UNL     1      -5.156  -0.860   2.875  1.00  0.00           H  
HETATM   39  H14 UNL     1      -2.777  -1.999   2.944  1.00  0.00           H  
HETATM   40  H15 UNL     1      -3.632  -3.142   0.913  1.00  0.00           H  
HETATM   41  H16 UNL     1      -2.094  -1.499  -0.039  1.00  0.00           H  
HETATM   42  H17 UNL     1      -0.537  -1.730   2.533  1.00  0.00           H  
HETATM   43  H18 UNL     1       0.564  -2.618  -0.009  1.00  0.00           H  
HETATM   44  H19 UNL     1       1.531  -1.047   2.154  1.00  0.00           H  
HETATM   45  H20 UNL     1       1.204  -0.653  -1.124  1.00  0.00           H  
HETATM   46  H21 UNL     1      -0.545  -0.535  -0.947  1.00  0.00           H  
HETATM   47  H22 UNL     1      -0.457   0.780   1.109  1.00  0.00           H  
HETATM   48  H23 UNL     1       0.919   2.568   1.155  1.00  0.00           H  
HETATM   49  H24 UNL     1       2.191   3.011  -0.956  1.00  0.00           H  
HETATM   50  H25 UNL     1       3.206   2.329   0.308  1.00  0.00           H  
HETATM   51  H26 UNL     1       2.103   0.972  -2.300  1.00  0.00           H  
HETATM   52  H27 UNL     1       4.076  -0.333  -2.341  1.00  0.00           H  
HETATM   53  H28 UNL     1       4.608   1.071   0.449  1.00  0.00           H  
HETATM   54  H29 UNL     1       5.072  -0.622  -0.042  1.00  0.00           H  
HETATM   55  H30 UNL     1       6.438   0.242  -1.882  1.00  0.00           H  
HETATM   56  H31 UNL     1       6.036   1.932  -1.535  1.00  0.00           H  
HETATM   57  H32 UNL     1       8.121   1.574  -0.552  1.00  0.00           H  
HETATM   58  H33 UNL     1       6.893   1.788   0.746  1.00  0.00           H  
HETATM   59  H34 UNL     1       9.549  -0.265   1.330  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   10   39
CONECT    9   40
CONECT   10   11   11   41
CONECT   11   12   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

HMDB0004694
     RDKit          3D
11,14,15-THETA
 59 58  0  0  0  0  0  0  0  0999 V2000
   -5.9182   -0.9525   -2.5758 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0047    0.4766   -2.1584 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8679    0.8913   -1.2510 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8393    0.0683    0.0261 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6681    0.5877    0.8252 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5392   -0.1300    2.1172 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6582   -0.0142    2.9310 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0548   -1.5535    1.9590 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0260   -2.3902    1.4155 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9085   -1.5679    1.0161 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6667   -1.6631    1.4532 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5208   -1.6823    0.5560 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6611   -1.5670    1.3397 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4413   -0.4734   -0.4031 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4271    0.7492    0.3850 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2138    1.7699    0.4063 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3926    2.0006   -0.3950 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7917    1.0681   -1.4236 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8958    0.3495   -1.4823 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9084    0.4465   -0.4008 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1789    0.9310   -1.0501 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2615    1.0779   -0.0408 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6181   -0.1753    0.6078 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1666   -1.3106    0.3648 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5877   -0.1137    1.6344 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5915   -1.1098   -3.4498 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2950   -1.6561   -1.7803 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9076   -1.2410   -2.9216 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9823    0.6417   -1.6702 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9725    1.1307   -3.0454 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9469    1.9537   -0.9613 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8923    0.7331   -1.7506 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6357   -0.9957   -0.2886 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7506    0.1529    0.6269 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7158    0.5120    0.2578 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8161    1.6770    1.0560 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7200    0.4149    2.6989 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1556   -0.8598    2.8753 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7773   -1.9989    2.9436 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6320   -3.1420    0.9128 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0937   -1.4994   -0.0385 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5365   -1.7301    2.5327 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5637   -2.6183   -0.0089 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5307   -1.0469    2.1542 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2040   -0.6533   -1.1237 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5452   -0.5351   -0.9468 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4566    0.7797    1.1086 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9193    2.5677    1.1549 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1909    3.0108   -0.9565 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2055    2.3289    0.3084 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1028    0.9724   -2.3001 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0758   -0.3328   -2.3406 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6080    1.0708    0.4487 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0723   -0.6221   -0.0416 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4379    0.2424   -1.8823 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0359    1.9321   -1.5349 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1207    1.5738   -0.5520 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8926    1.7885    0.7462 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.5495   -0.2648    1.3303 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  1  0
  8 10  1  0
 10 11  2  0
 11 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  0
  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
(5Z,8Z,12E)-11,14,15-Trihydroxyeicosa-5,8,12-trienoic acid	ChEBI
(5Z,8Z,12E)-11,14,15-Trihydroxyeicosatrienoic acid	ChEBI
(5Z,8Z,12E)-11,14,15-Trihydroxyicosatrienoic acid	ChEBI
11,14,15-Trihydroxy-(5Z,8Z,12E)-eicosatrienoic acid	ChEBI
11,14,15-Trihydroxy-5Z,8Z,12E-eicosatrienoic acid	ChEBI
11,14,15-Trihydroxyicosatrienoic acid	ChEBI
(5Z,8Z,12E)-11,14,15-Trihydroxyicosa-5,8,12-trienoic acid	Kegg
(5Z,8Z,12E)-11,14,15-Trihydroxyeicosa-5,8,12-trienoate	Generator
(5Z,8Z,12E)-11,14,15-Trihydroxyeicosatrienoate	Generator
(5Z,8Z,12E)-11,14,15-Trihydroxyicosatrienoate	Generator
11,14,15-Trihydroxy-(5Z,8Z,12E)-eicosatrienoate	Generator
11,14,15-Trihydroxy-5Z,8Z,12E-eicosatrienoate	Generator
11,14,15-Trihydroxyicosatrienoate	Generator
(5Z,8Z,12E)-11,14,15-Trihydroxyicosa-5,8,12-trienoate	Generator
11,14,15-THET	HMDB
11,14,15-Trihydroxyeicosa-5,8,12-trienoic acid	HMDB
11,14,15-Trihydroxyeicosatetraenoic acid	HMDB

Chemical Formula

C₂₀H₃₄O₅

Average Molecular Weight

354.481

Monoisotopic Molecular Weight

354.240624198

IUPAC Name

(5Z,8Z,12E)-11,14,15-trihydroxyicosa-5,8,12-trienoic acid

Traditional Name

(5Z,8Z,12E)-11,14,15-trihydroxyicosa-5,8,12-trienoic acid

CAS Registry Number

Not Available

SMILES

CCCCCC(O)C(O)\C=C\C(O)C\C=C/C\C=C/CCCC(O)=O

InChI Identifier

InChI=1S/C20H34O5/c1-2-3-9-13-18(22)19(23)16-15-17(21)12-10-7-5-4-6-8-11-14-20(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+

InChI Key

YCFPVUKKIWMCJK-LTCHCNGXSA-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

leukotriene (CHEBI:34131 )
Hydroxy/hydroperoxyeicosatrienoic acids (C14814 )
Hydroxy/hydroperoxyeicosatrienoic acids (LMFA03050018 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0004694)
Membrane (HMDB: HMDB0004694)

Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)
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)

Equine

Horse (FooDB: FOOD00378)

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)

Process

Naturally occurring process

Biological process

Biochemical pathway

Metabolic pathway

Arachidonic Acid Metabolism (HMDB: HMDB0004694)

Disease pathway

Leukotriene C4 Synthesis Deficiency (PathBank: SMP0000353)

Drug action pathway

Piroxicam Action Pathway (PathBank: SMP0000077)
Acetylsalicylic Acid Action Pathway (PathBank: SMP0000083)
Etodolac Action Pathway (PathBank: SMP0000084)
Ketoprofen Action Pathway (PathBank: SMP0000085)
Ibuprofen Action Pathway (PathBank: SMP0000086)
Rofecoxib Action Pathway (PathBank: SMP0000087)
Diclofenac Action Pathway (PathBank: SMP0000093)
Sulindac Action Pathway (PathBank: SMP0000094)
Celecoxib Action Pathway (PathBank: SMP0000096)
Ketorolac Action Pathway (PathBank: SMP0000098)
Suprofen Action Pathway (PathBank: SMP0000101)
Bromfenac Action Pathway (PathBank: SMP0000102)
Indomethacin Action Pathway (PathBank: SMP0000104)
Mefenamic Acid Action Pathway (PathBank: SMP0000109)
Oxaprozin Action Pathway (PathBank: SMP0000113)
Nabumetone Action Pathway (PathBank: SMP0000114)
Naproxen Action Pathway (PathBank: SMP0000120)
Diflunisal Action Pathway (PathBank: SMP0000289)
Meloxicam Action Pathway (PathBank: SMP0000106)
Valdecoxib Action Pathway (PathBank: SMP0000116)
Antipyrine Action Pathway (PathBank: SMP0000692)
Antrafenine Action Pathway (PathBank: SMP0000693)
Carprofen Action Pathway (PathBank: SMP0000694)
Etoricoxib Action Pathway (PathBank: SMP0000695)
Fenoprofen Action Pathway (PathBank: SMP0000696)
Flurbiprofen Action Pathway (PathBank: SMP0000697)
Magnesium Salicylate Action Pathway (PathBank: SMP0000698)
Lumiracoxib Action Pathway (PathBank: SMP0000699)
Lornoxicam Action Pathway (PathBank: SMP0000700)
Phenylbutazone Action Pathway (PathBank: SMP0000701)
Nepafenac Action Pathway (PathBank: SMP0000702)
Trisalicylate-Choline Action Pathway (PathBank: SMP0000703)
Tolmetin Action Pathway (PathBank: SMP0000704)
Tiaprofenic Acid Action Pathway (PathBank: SMP0000705)
Tenoxicam Action Pathway (PathBank: SMP0000706)
Salsalate Action Pathway (PathBank: SMP0000707)
Salicylate-Sodium Action Pathway (PathBank: SMP0000708)
Salicylic Acid Action Pathway (PathBank: SMP0000709)
Acetaminophen Action Pathway (PathBank: SMP0000710)

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	0.053 g/L	ALOGPS
logP	4.47	ALOGPS
logP	3.41	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Acidic)	4.82	ChemAxon
pKa (Strongest Basic)	-2.9	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	41.29 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]+	193.703	31661259
DarkChem	[M-H]-	193.266	31661259
DeepCCS	[M+H]+	198.926	30932474
DeepCCS	[M-H]-	196.568	30932474
DeepCCS	[M-2H]-	229.454	30932474
DeepCCS	[M+Na]+	205.019	30932474
AllCCS	[M+H]+	195.9	32859911
AllCCS	[M+H-H2O]+	193.2	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 Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
11,14,15-THETA	CCCCCC(O)C(O)\C=C\C(O)C\C=C/C\C=C/CCCC(O)=O	4565.0	Standard polar	33892256
11,14,15-THETA	CCCCCC(O)C(O)\C=C\C(O)C\C=C/C\C=C/CCCC(O)=O	2512.6	Standard non polar	33892256
11,14,15-THETA	CCCCCC(O)C(O)\C=C\C(O)C\C=C/C\C=C/CCCC(O)=O	2762.0	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
11,14,15-THETA,1TMS,isomer #1	CCCCCC(O[Si](C)(C)C)C(O)/C=C/C(O)C/C=C\C/C=C\CCCC(=O)O	2990.2	Semi standard non polar	33892256
11,14,15-THETA,1TMS,isomer #2	CCCCCC(O)C(/C=C/C(O)C/C=C\C/C=C\CCCC(=O)O)O[Si](C)(C)C	3005.6	Semi standard non polar	33892256
11,14,15-THETA,1TMS,isomer #3	CCCCCC(O)C(O)/C=C/C(C/C=C\C/C=C\CCCC(=O)O)O[Si](C)(C)C	3042.1	Semi standard non polar	33892256
11,14,15-THETA,1TMS,isomer #4	CCCCCC(O)C(O)/C=C/C(O)C/C=C\C/C=C\CCCC(=O)O[Si](C)(C)C	2921.2	Semi standard non polar	33892256
11,14,15-THETA,2TMS,isomer #1	CCCCCC(O[Si](C)(C)C)C(/C=C/C(O)C/C=C\C/C=C\CCCC(=O)O)O[Si](C)(C)C	2973.0	Semi standard non polar	33892256
11,14,15-THETA,2TMS,isomer #2	CCCCCC(O[Si](C)(C)C)C(O)/C=C/C(C/C=C\C/C=C\CCCC(=O)O)O[Si](C)(C)C	2996.1	Semi standard non polar	33892256
11,14,15-THETA,2TMS,isomer #3	CCCCCC(O[Si](C)(C)C)C(O)/C=C/C(O)C/C=C\C/C=C\CCCC(=O)O[Si](C)(C)C	2897.9	Semi standard non polar	33892256
11,14,15-THETA,2TMS,isomer #4	CCCCCC(O)C(/C=C/C(C/C=C\C/C=C\CCCC(=O)O)O[Si](C)(C)C)O[Si](C)(C)C	3002.5	Semi standard non polar	33892256
11,14,15-THETA,2TMS,isomer #5	CCCCCC(O)C(/C=C/C(O)C/C=C\C/C=C\CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C	2922.1	Semi standard non polar	33892256
11,14,15-THETA,2TMS,isomer #6	CCCCCC(O)C(O)/C=C/C(C/C=C\C/C=C\CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C	2943.2	Semi standard non polar	33892256
11,14,15-THETA,3TMS,isomer #1	CCCCCC(O[Si](C)(C)C)C(/C=C/C(C/C=C\C/C=C\CCCC(=O)O)O[Si](C)(C)C)O[Si](C)(C)C	2944.0	Semi standard non polar	33892256
11,14,15-THETA,3TMS,isomer #2	CCCCCC(O[Si](C)(C)C)C(/C=C/C(O)C/C=C\C/C=C\CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C	2880.7	Semi standard non polar	33892256
11,14,15-THETA,3TMS,isomer #3	CCCCCC(O[Si](C)(C)C)C(O)/C=C/C(C/C=C\C/C=C\CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C	2876.8	Semi standard non polar	33892256
11,14,15-THETA,3TMS,isomer #4	CCCCCC(O)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	2892.3	Semi standard non polar	33892256
11,14,15-THETA,4TMS,isomer #1	CCCCCC(O[Si](C)(C)C)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	2828.2	Semi standard non polar	33892256
11,14,15-THETA,1TBDMS,isomer #1	CCCCCC(O[Si](C)(C)C(C)(C)C)C(O)/C=C/C(O)C/C=C\C/C=C\CCCC(=O)O	3240.2	Semi standard non polar	33892256
11,14,15-THETA,1TBDMS,isomer #2	CCCCCC(O)C(/C=C/C(O)C/C=C\C/C=C\CCCC(=O)O)O[Si](C)(C)C(C)(C)C	3250.5	Semi standard non polar	33892256
11,14,15-THETA,1TBDMS,isomer #3	CCCCCC(O)C(O)/C=C/C(C/C=C\C/C=C\CCCC(=O)O)O[Si](C)(C)C(C)(C)C	3277.1	Semi standard non polar	33892256
11,14,15-THETA,1TBDMS,isomer #4	CCCCCC(O)C(O)/C=C/C(O)C/C=C\C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C	3165.1	Semi standard non polar	33892256
11,14,15-THETA,2TBDMS,isomer #1	CCCCCC(O[Si](C)(C)C(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	3441.5	Semi standard non polar	33892256
11,14,15-THETA,2TBDMS,isomer #2	CCCCCC(O[Si](C)(C)C(C)(C)C)C(O)/C=C/C(C/C=C\C/C=C\CCCC(=O)O)O[Si](C)(C)C(C)(C)C	3451.3	Semi standard non polar	33892256
11,14,15-THETA,2TBDMS,isomer #3	CCCCCC(O[Si](C)(C)C(C)(C)C)C(O)/C=C/C(O)C/C=C\C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C	3392.1	Semi standard non polar	33892256
11,14,15-THETA,2TBDMS,isomer #4	CCCCCC(O)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	3463.2	Semi standard non polar	33892256
11,14,15-THETA,2TBDMS,isomer #5	CCCCCC(O)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	3416.4	Semi standard non polar	33892256
11,14,15-THETA,2TBDMS,isomer #6	CCCCCC(O)C(O)/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	3429.9	Semi standard non polar	33892256
11,14,15-THETA,3TBDMS,isomer #1	CCCCCC(O[Si](C)(C)C(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	3589.9	Semi standard non polar	33892256
11,14,15-THETA,3TBDMS,isomer #2	CCCCCC(O[Si](C)(C)C(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	3571.3	Semi standard non polar	33892256
11,14,15-THETA,3TBDMS,isomer #3	CCCCCC(O[Si](C)(C)C(C)(C)C)C(O)/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	3606.8	Semi standard non polar	33892256
11,14,15-THETA,3TBDMS,isomer #4	CCCCCC(O)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	3619.0	Semi standard non polar	33892256
11,14,15-THETA,4TBDMS,isomer #1	CCCCCC(O[Si](C)(C)C(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	3740.0	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 - 11,14,15-THETA GC-MS (Non-derivatized) - 70eV, Positive	splash10-0udr-5593000000-b44c164b1afc4290e62a	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 11,14,15-THETA GC-MS (4 TMS) - 70eV, Positive	splash10-00b9-8310987000-e42844df87dbeaaac7b7	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 11,14,15-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 - 11,14,15-THETA 10V, Positive-QTOF	splash10-00kr-0019000000-5d98b30fc798f154e3cd	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 11,14,15-THETA 20V, Positive-QTOF	splash10-0600-8697000000-f2898f6e9aa37eb19701	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 11,14,15-THETA 40V, Positive-QTOF	splash10-05tf-9420000000-4b2f1a462946904efa65	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 11,14,15-THETA 10V, Negative-QTOF	splash10-0udi-0009000000-81208c2a7c484c87062f	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 11,14,15-THETA 20V, Negative-QTOF	splash10-0f79-4389000000-3a054cf28c217520eeed	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 11,14,15-THETA 40V, Negative-QTOF	splash10-0a4i-9340000000-315051dfef85d54b3de6	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 11,14,15-THETA 10V, Positive-QTOF	splash10-00kr-0119000000-54253aeda6e4903c01bc	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 11,14,15-THETA 20V, Positive-QTOF	splash10-014r-4339000000-fe248a9e503f326b0181	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 11,14,15-THETA 40V, Positive-QTOF	splash10-05nf-9400000000-b63770838f1639e0172e	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 11,14,15-THETA 10V, Negative-QTOF	splash10-0udi-0019000000-26292874068f05134a76	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 11,14,15-THETA 20V, Negative-QTOF	splash10-0kbs-3967000000-5212de307caf1623f831	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 11,14,15-THETA 40V, Negative-QTOF	splash10-0002-9530000000-88a46328b37a9b5888f5	2021-09-23	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Not Available

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

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

FDB023410

KNApSAcK ID

Not Available

Chemspider ID

10128354

KEGG Compound ID

C14814

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11954059

PDB ID

Not Available

ChEBI ID

34131

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

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 ]
Zhu D, Medhora M, Campbell WB, Spitzbarth N, Baker JE, Jacobs ER: Chronic hypoxia activates lung 15-lipoxygenase, which catalyzes production of 15-HETE and enhances constriction in neonatal rabbit pulmonary arteries. Circ Res. 2003 May 16;92(9):992-1000. Epub 2003 Apr 10. [PubMed:12690037 ]
Pfister SL, Spitzbarth N, Nithipatikom K, Edgemond WS, Falck JR, Campbell WB: Identification of the 11,14,15- and 11,12, 15-trihydroxyeicosatrienoic acids as endothelium-derived relaxing factors of rabbit aorta. J Biol Chem. 1998 Nov 20;273(47):30879-87. [PubMed:9812980 ]

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 11,14,15-THETA (HMDB0004694)

MOL for HMDB0004694 (11,14,15-THETA)

3D MOL for HMDB0004694 (11,14,15-THETA)

3D SDF for HMDB0004694 (11,14,15-THETA)

3D-SDF for HMDB0004694 (11,14,15-THETA)

PDB for HMDB0004694 (11,14,15-THETA)

3D PDB for HMDB0004694 (11,14,15-THETA)

SMILES for HMDB0004694 (11,14,15-THETA)

INCHI for HMDB0004694 (11,14,15-THETA)

Structure for HMDB0004694 (11,14,15-THETA)

3D Structure for HMDB0004694 (11,14,15-THETA)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

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Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes