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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2006-08-14 02:16:26 UTC

Update Date

2022-03-07 02:49:21 UTC

HMDB ID

HMDB0004708

Secondary Accession Numbers

HMDB04708

Metabolite Identification

Common Name

9,12,13-TriHOME

Description

9,12,13-TriHOME is a trihydroxyoctadecenoic acid metabolite of linoleic acid, one of the major fatty acids found in lipids. Vascular tissue converts various polyunsaturated fatty acids to monohydroxy and trihydroxy metabolites derived from hydroperoxides which may be involved in regulating prostaglandin synthesis. The absolute amounts of 9,12,13-TriHOME varies considerably from one species to another. There are several possible mechanisms for the formation of esterified oxygenated polyunsaturated fatty acids: oxygenated and then incorporated into lipids, not well incorporated into either vascular endothelial or smooth muscle cells, or could accumulated in lipids either due to autoxidation in vivo or to the action of an enzyme similar to Iipoxygenase. (PMID: 3997883 , 6414520 ).

Structure

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

HMDB0004708
     RDKit          3D
9,12,13-TriHOME
 57 56  0  0  0  0  0  0  0  0999 V2000
   -6.5667   -0.1887   -0.6051 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2859    0.7687    0.5280 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3692    1.8764    0.2293 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9775    1.6628   -0.1799 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0377    0.9743    0.7229 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2106   -0.4481    1.0503 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1555   -0.7452    1.9967 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8240   -1.3676   -0.1185 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.6549   -1.2591   -1.1738 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3808   -1.2205   -0.4400 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9542   -0.3985   -1.3942 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4657   -0.2092   -1.7595 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8880    1.0981   -1.6295 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3441   -1.1379   -0.9340 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7705   -0.9426   -1.3063 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7092   -1.8438   -0.5440 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6036   -1.5696    0.9169 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8696   -0.1892    1.3013 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1428    0.4870    1.0928 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7088    0.7081   -0.2447 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0073    1.4801   -0.0228 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4071    1.8028    1.1102 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7686    1.8341   -1.1266 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2239   -1.1916   -0.2676 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6644   -0.2676   -0.8413 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9913    0.1150   -1.4780 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3124    1.2784    0.6943 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1499    0.2614    1.5123 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4439    2.6123    1.0884 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8580    2.4648   -0.6240 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5369    2.7047   -0.3506 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9584    1.2436   -1.2267 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9652    1.0884    0.3547 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9969    1.5616    1.7038 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1077   -0.7755    1.5601 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2844   -0.0427    2.7093 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9345   -2.4087    0.3081 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2619   -1.2336   -2.0666 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6274   -1.7844    0.0993 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7251    0.1563   -1.9214 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5907   -0.5108   -2.8211 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6147    1.5723   -2.4662 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2048   -0.8929    0.1399 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0502   -2.1820   -1.1725 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9574   -1.1197   -2.4031 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0088    0.1402   -1.1255 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2976   -2.9187   -0.7179 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7078   -1.8945   -0.9690 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5453   -1.8467    1.2210 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2025   -2.3245    1.5165 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0092    0.4688    0.9124 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6567   -0.1137    2.4339 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9606    0.0501    1.7491 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0304    1.5313    1.5567 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1134    1.3839   -0.8992 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0249   -0.1395   -0.8395 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7989    1.8418   -1.0984 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  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  2  0
 21 23  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  2 27  1  0
  2 28  1  0
  3 29  1  0
  3 30  1  0
  4 31  1  0
  4 32  1  0
  5 33  1  0
  5 34  1  0
  6 35  1  1
  7 36  1  0
  8 37  1  1
  9 38  1  0
 10 39  1  0
 11 40  1  0
 12 41  1  6
 13 42  1  0
 14 43  1  0
 14 44  1  0
 15 45  1  0
 15 46  1  0
 16 47  1  0
 16 48  1  0
 17 49  1  0
 17 50  1  0
 18 51  1  0
 18 52  1  0
 19 53  1  0
 19 54  1  0
 20 55  1  0
 20 56  1  0
 23 57  1  0
M  END


  Mrv0541 02231219582D          

 23 22  0  0  1  0            999 V2000
   26.2070  -18.8494    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.9214  -20.9118    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.0648  -18.8494    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   35.4945  -20.0869    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   34.7801  -18.8494    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   30.4936  -19.6743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.2080  -20.0869    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.2070  -19.6743    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   29.7791  -20.0869    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.9224  -19.6743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.4927  -20.0869    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.7782  -19.6743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.9214  -20.0869    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   29.0648  -19.6743    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   32.6369  -20.0869    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.0638  -20.0869    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.3514  -19.6743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.6360  -19.6743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.3502  -20.0869    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.3493  -19.6743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.0656  -20.0869    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.6348  -20.0869    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.7801  -19.6743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  8  1  1  6  0  0  0
 13  2  1  6  0  0  0
 14  3  1  1  0  0  0
  4 23  1  0  0  0  0
  5 23  2  0  0  0  0
  6  7  1  0  0  0  0
  6  9  1  0  0  0  0
  7 10  1  0  0  0  0
  8 11  1  0  0  0  0
  8 13  1  0  0  0  0
  9 14  1  0  0  0  0
 10 15  1  0  0  0  0
 11 12  1  0  0  0  0
 12 16  1  0  0  0  0
 13 18  1  0  0  0  0
 14 19  1  0  0  0  0
 15 17  1  0  0  0  0
 16 20  1  0  0  0  0
 17 21  1  0  0  0  0
 18 19  2  0  0  0  0
 20 22  1  0  0  0  0
 21 23  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0004708

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C18H34O5/c1-2-3-7-11-16(20)17(21)14-13-15(19)10-8-5-4-6-9-12-18(22)23/h13-17,19-21H,2-12H2,1H3,(H,22,23)/b14-13+/t15-,16-,17-/m0/s1

> <INCHI_KEY>
MDIUMSLCYIJBQC-MVFSOIOZSA-N

> <FORMULA>
C18H34O5

> <MOLECULAR_WEIGHT>
330.4596

> <EXACT_MASS>
330.240624198

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
40.03819941809534

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(9S,10E,12S,13S)-9,12,13-trihydroxyoctadec-10-enoic acid

> <ALOGPS_LOGP>
3.77

> <JCHEM_LOGP>
3.24727271

> <ALOGPS_LOGS>
-3.33

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
13.636226243564447

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.6767451828624695

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8471921473040265

> <JCHEM_POLAR_SURFACE_AREA>
97.99000000000001

> <JCHEM_REFRACTIVITY>
91.79469999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
15

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.55e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(9S,10E,12S,13S)-9,12,13-trihydroxyoctadec-10-enoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0004708
     RDKit          3D
9,12,13-TriHOME
 57 56  0  0  0  0  0  0  0  0999 V2000
   -6.5667   -0.1887   -0.6051 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2859    0.7687    0.5280 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3692    1.8764    0.2293 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9775    1.6628   -0.1799 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0377    0.9743    0.7229 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2106   -0.4481    1.0503 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1555   -0.7452    1.9967 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8240   -1.3676   -0.1185 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.6549   -1.2591   -1.1738 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3808   -1.2205   -0.4400 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9542   -0.3985   -1.3942 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4657   -0.2092   -1.7595 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8880    1.0981   -1.6295 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3441   -1.1379   -0.9340 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7705   -0.9426   -1.3063 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7092   -1.8438   -0.5440 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6036   -1.5696    0.9169 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8696   -0.1892    1.3013 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1428    0.4870    1.0928 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7088    0.7081   -0.2447 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0073    1.4801   -0.0228 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4071    1.8028    1.1102 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7686    1.8341   -1.1266 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2239   -1.1916   -0.2676 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6644   -0.2676   -0.8413 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9913    0.1150   -1.4780 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3124    1.2784    0.6943 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1499    0.2614    1.5123 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4439    2.6123    1.0884 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8580    2.4648   -0.6240 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5369    2.7047   -0.3506 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9584    1.2436   -1.2267 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9652    1.0884    0.3547 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9969    1.5616    1.7038 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1077   -0.7755    1.5601 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2844   -0.0427    2.7093 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9345   -2.4087    0.3081 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2619   -1.2336   -2.0666 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6274   -1.7844    0.0993 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7251    0.1563   -1.9214 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5907   -0.5108   -2.8211 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6147    1.5723   -2.4662 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2048   -0.8929    0.1399 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0502   -2.1820   -1.1725 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9574   -1.1197   -2.4031 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0088    0.1402   -1.1255 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2976   -2.9187   -0.7179 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7078   -1.8945   -0.9690 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5453   -1.8467    1.2210 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2025   -2.3245    1.5165 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0092    0.4688    0.9124 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6567   -0.1137    2.4339 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9606    0.0501    1.7491 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0304    1.5313    1.5567 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1134    1.3839   -0.8992 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0249   -0.1395   -0.8395 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7989    1.8418   -1.0984 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  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  2  0
 21 23  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  2 27  1  0
  2 28  1  0
  3 29  1  0
  3 30  1  0
  4 31  1  0
  4 32  1  0
  5 33  1  0
  5 34  1  0
  6 35  1  1
  7 36  1  0
  8 37  1  1
  9 38  1  0
 10 39  1  0
 11 40  1  0
 12 41  1  6
 13 42  1  0
 14 43  1  0
 14 44  1  0
 15 45  1  0
 15 46  1  0
 16 47  1  0
 16 48  1  0
 17 49  1  0
 17 50  1  0
 18 51  1  0
 18 52  1  0
 19 53  1  0
 19 54  1  0
 20 55  1  0
 20 56  1  0
 23 57  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0      48.920 -35.186   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      50.253 -39.035   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      54.254 -35.186   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      66.256 -37.496   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0      64.923 -35.186   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      56.921 -36.725   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      58.255 -37.496   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      48.920 -36.725   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      55.588 -37.496   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      59.588 -36.725   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      47.586 -37.496   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      46.253 -36.725   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      50.253 -37.496   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      54.254 -36.725   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      60.922 -37.496   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      44.919 -37.496   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      62.256 -36.725   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      51.587 -36.725   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      52.920 -37.496   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      43.585 -36.725   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      63.589 -37.496   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      42.252 -37.496   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      64.923 -36.725   0.000  0.00  0.00           C+0
CONECT    1    8                                                            
CONECT    2   13                                                            
CONECT    3   14                                                            
CONECT    4   23                                                            
CONECT    5   23                                                            
CONECT    6    7    9                                                       
CONECT    7    6   10                                                       
CONECT    8    1   11   13                                                  
CONECT    9    6   14                                                       
CONECT   10    7   15                                                       
CONECT   11    8   12                                                       
CONECT   12   11   16                                                       
CONECT   13    2    8   18                                                  
CONECT   14    3    9   19                                                  
CONECT   15   10   17                                                       
CONECT   16   12   20                                                       
CONECT   17   15   21                                                       
CONECT   18   13   19                                                       
CONECT   19   14   18                                                       
CONECT   20   16   22                                                       
CONECT   21   17   23                                                       
CONECT   22   20                                                            
CONECT   23    4    5   21                                                  
MASTER        0    0    0    0    0    0    0    0   23    0   44    0
END

COMPND    HMDB0004708
HETATM    1  C1  UNL     1      -6.567  -0.189  -0.605  1.00  0.00           C  
HETATM    2  C2  UNL     1      -6.286   0.769   0.528  1.00  0.00           C  
HETATM    3  C3  UNL     1      -5.369   1.876   0.229  1.00  0.00           C  
HETATM    4  C4  UNL     1      -3.978   1.663  -0.180  1.00  0.00           C  
HETATM    5  C5  UNL     1      -3.038   0.974   0.723  1.00  0.00           C  
HETATM    6  C6  UNL     1      -3.211  -0.448   1.050  1.00  0.00           C  
HETATM    7  O1  UNL     1      -2.155  -0.745   1.997  1.00  0.00           O  
HETATM    8  C7  UNL     1      -2.824  -1.368  -0.119  1.00  0.00           C  
HETATM    9  O2  UNL     1      -3.655  -1.259  -1.174  1.00  0.00           O  
HETATM   10  C8  UNL     1      -1.381  -1.221  -0.440  1.00  0.00           C  
HETATM   11  C9  UNL     1      -0.954  -0.398  -1.394  1.00  0.00           C  
HETATM   12  C10 UNL     1       0.466  -0.209  -1.760  1.00  0.00           C  
HETATM   13  O3  UNL     1       0.888   1.098  -1.630  1.00  0.00           O  
HETATM   14  C11 UNL     1       1.344  -1.138  -0.934  1.00  0.00           C  
HETATM   15  C12 UNL     1       2.771  -0.943  -1.306  1.00  0.00           C  
HETATM   16  C13 UNL     1       3.709  -1.844  -0.544  1.00  0.00           C  
HETATM   17  C14 UNL     1       3.604  -1.570   0.917  1.00  0.00           C  
HETATM   18  C15 UNL     1       3.870  -0.189   1.301  1.00  0.00           C  
HETATM   19  C16 UNL     1       5.143   0.487   1.093  1.00  0.00           C  
HETATM   20  C17 UNL     1       5.709   0.708  -0.245  1.00  0.00           C  
HETATM   21  C18 UNL     1       7.007   1.480  -0.023  1.00  0.00           C  
HETATM   22  O4  UNL     1       7.407   1.803   1.110  1.00  0.00           O  
HETATM   23  O5  UNL     1       7.769   1.834  -1.127  1.00  0.00           O  
HETATM   24  H1  UNL     1      -6.224  -1.192  -0.268  1.00  0.00           H  
HETATM   25  H2  UNL     1      -7.664  -0.268  -0.841  1.00  0.00           H  
HETATM   26  H3  UNL     1      -5.991   0.115  -1.478  1.00  0.00           H  
HETATM   27  H4  UNL     1      -7.312   1.278   0.694  1.00  0.00           H  
HETATM   28  H5  UNL     1      -6.150   0.261   1.512  1.00  0.00           H  
HETATM   29  H6  UNL     1      -5.444   2.612   1.088  1.00  0.00           H  
HETATM   30  H7  UNL     1      -5.858   2.465  -0.624  1.00  0.00           H  
HETATM   31  H8  UNL     1      -3.537   2.705  -0.351  1.00  0.00           H  
HETATM   32  H9  UNL     1      -3.958   1.244  -1.227  1.00  0.00           H  
HETATM   33  H10 UNL     1      -1.965   1.088   0.355  1.00  0.00           H  
HETATM   34  H11 UNL     1      -2.997   1.562   1.704  1.00  0.00           H  
HETATM   35  H12 UNL     1      -4.108  -0.776   1.560  1.00  0.00           H  
HETATM   36  H13 UNL     1      -2.284  -0.043   2.709  1.00  0.00           H  
HETATM   37  H14 UNL     1      -2.935  -2.409   0.308  1.00  0.00           H  
HETATM   38  H15 UNL     1      -3.262  -1.234  -2.067  1.00  0.00           H  
HETATM   39  H16 UNL     1      -0.627  -1.784   0.099  1.00  0.00           H  
HETATM   40  H17 UNL     1      -1.725   0.156  -1.921  1.00  0.00           H  
HETATM   41  H18 UNL     1       0.591  -0.511  -2.821  1.00  0.00           H  
HETATM   42  H19 UNL     1       0.615   1.572  -2.466  1.00  0.00           H  
HETATM   43  H20 UNL     1       1.205  -0.893   0.140  1.00  0.00           H  
HETATM   44  H21 UNL     1       1.050  -2.182  -1.172  1.00  0.00           H  
HETATM   45  H22 UNL     1       2.957  -1.120  -2.403  1.00  0.00           H  
HETATM   46  H23 UNL     1       3.009   0.140  -1.126  1.00  0.00           H  
HETATM   47  H24 UNL     1       3.298  -2.919  -0.718  1.00  0.00           H  
HETATM   48  H25 UNL     1       4.708  -1.894  -0.969  1.00  0.00           H  
HETATM   49  H26 UNL     1       2.545  -1.847   1.221  1.00  0.00           H  
HETATM   50  H27 UNL     1       4.203  -2.324   1.517  1.00  0.00           H  
HETATM   51  H28 UNL     1       3.009   0.469   0.912  1.00  0.00           H  
HETATM   52  H29 UNL     1       3.657  -0.114   2.434  1.00  0.00           H  
HETATM   53  H30 UNL     1       5.961   0.050   1.749  1.00  0.00           H  
HETATM   54  H31 UNL     1       5.030   1.531   1.557  1.00  0.00           H  
HETATM   55  H32 UNL     1       5.113   1.384  -0.899  1.00  0.00           H  
HETATM   56  H33 UNL     1       6.025  -0.140  -0.840  1.00  0.00           H  
HETATM   57  H34 UNL     1       8.799   1.842  -1.098  1.00  0.00           H  
CONECT    1    2   24   25   26
CONECT    2    3   27   28
CONECT    3    4   29   30
CONECT    4    5   31   32
CONECT    5    6   33   34
CONECT    6    7    8   35
CONECT    7   36
CONECT    8    9   10   37
CONECT    9   38
CONECT   10   11   11   39
CONECT   11   12   40
CONECT   12   13   14   41
CONECT   13   42
CONECT   14   15   43   44
CONECT   15   16   45   46
CONECT   16   17   47   48
CONECT   17   18   49   50
CONECT   18   19   51   52
CONECT   19   20   53   54
CONECT   20   21   55   56
CONECT   21   22   22   23
CONECT   23   57
END

HMDB0004708
     RDKit          3D
9,12,13-TriHOME
 57 56  0  0  0  0  0  0  0  0999 V2000
   -6.5667   -0.1887   -0.6051 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2859    0.7687    0.5280 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3692    1.8764    0.2293 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9775    1.6628   -0.1799 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0377    0.9743    0.7229 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2106   -0.4481    1.0503 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1555   -0.7452    1.9967 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8240   -1.3676   -0.1185 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.6549   -1.2591   -1.1738 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3808   -1.2205   -0.4400 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9542   -0.3985   -1.3942 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4657   -0.2092   -1.7595 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8880    1.0981   -1.6295 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3441   -1.1379   -0.9340 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7705   -0.9426   -1.3063 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7092   -1.8438   -0.5440 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6036   -1.5696    0.9169 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8696   -0.1892    1.3013 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1428    0.4870    1.0928 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7088    0.7081   -0.2447 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0073    1.4801   -0.0228 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4071    1.8028    1.1102 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7686    1.8341   -1.1266 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2239   -1.1916   -0.2676 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6644   -0.2676   -0.8413 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9913    0.1150   -1.4780 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3124    1.2784    0.6943 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1499    0.2614    1.5123 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4439    2.6123    1.0884 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8580    2.4648   -0.6240 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5369    2.7047   -0.3506 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9584    1.2436   -1.2267 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9652    1.0884    0.3547 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9969    1.5616    1.7038 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1077   -0.7755    1.5601 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2844   -0.0427    2.7093 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9345   -2.4087    0.3081 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2619   -1.2336   -2.0666 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6274   -1.7844    0.0993 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7251    0.1563   -1.9214 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5907   -0.5108   -2.8211 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6147    1.5723   -2.4662 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2048   -0.8929    0.1399 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0502   -2.1820   -1.1725 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9574   -1.1197   -2.4031 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0088    0.1402   -1.1255 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2976   -2.9187   -0.7179 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7078   -1.8945   -0.9690 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5453   -1.8467    1.2210 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2025   -2.3245    1.5165 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0092    0.4688    0.9124 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6567   -0.1137    2.4339 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9606    0.0501    1.7491 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0304    1.5313    1.5567 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1134    1.3839   -0.8992 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0249   -0.1395   -0.8395 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7989    1.8418   -1.0984 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  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  2  0
 21 23  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  2 27  1  0
  2 28  1  0
  3 29  1  0
  3 30  1  0
  4 31  1  0
  4 32  1  0
  5 33  1  0
  5 34  1  0
  6 35  1  1
  7 36  1  0
  8 37  1  1
  9 38  1  0
 10 39  1  0
 11 40  1  0
 12 41  1  6
 13 42  1  0
 14 43  1  0
 14 44  1  0
 15 45  1  0
 15 46  1  0
 16 47  1  0
 16 48  1  0
 17 49  1  0
 17 50  1  0
 18 51  1  0
 18 52  1  0
 19 53  1  0
 19 54  1  0
 20 55  1  0
 20 56  1  0
 23 57  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(10E)-(9S,12S,13S)-9,12,13-Trihydroxyoctadec-10-enoic acid	ChEBI
9(S),12(S),13(S)-Trihydroxy-10(e)-octadecenoic acid	ChEBI
9S,12S,13S-Trihydroxy-10E-octadecenoic acid	ChEBI
(10E)-(9S,12S,13S)-9,12,13-Trihydroxyoctadec-10-enoate	Generator
9(S),12(S),13(S)-Trihydroxy-10(e)-octadecenoate	Generator
9S,12S,13S-Trihydroxy-10E-octadecenoate	Generator
Pinellic acid	MeSH, HMDB

Chemical Formula

C₁₈H₃₄O₅

Average Molecular Weight

330.4596

Monoisotopic Molecular Weight

330.240624198

IUPAC Name

(9S,10E,12S,13S)-9,12,13-trihydroxyoctadec-10-enoic acid

Traditional Name

(9S,10E,12S,13S)-9,12,13-trihydroxyoctadec-10-enoic acid

CAS Registry Number

Not Available

SMILES

CCCCC[C@H](O)[C@@H](O)\C=C\[C@@H](O)CCCCCCCC(O)=O

InChI Identifier

InChI=1S/C18H34O5/c1-2-3-7-11-16(20)17(21)14-13-15(19)10-8-5-4-6-9-12-18(22)23/h13-17,19-21H,2-12H2,1H3,(H,22,23)/b14-13+/t15-,16-,17-/m0/s1

InChI Key

MDIUMSLCYIJBQC-MVFSOIOZSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acids and conjugates

Direct Parent

Long-chain fatty acids

Alternative Parents

Substituents

Long-chain fatty acid
Hydroxy fatty acid
Unsaturated fatty acid
Secondary alcohol
Polyol
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

TriHOME (CHEBI:34506 )
Other Octadecanoids (C14833 )
Other Octadecanoids (LMFA02000014 )

Ontology

Not Available

Non-excretory biofluid

Blood (PMID: 18953024)

Blood (HMDB: HMDB0004708)
Urine (HMDB: HMDB0004708)

Cellular substructure

Extracellular (HMDB: HMDB0004708)
Membrane (HMDB: HMDB0004708)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0004708)

Source

Endogenous

Endogenous (HMDB: HMDB0004708)

Animal

Animal (HMDB: HMDB0004708)

Exogenous

Food

Food (HMDB: HMDB0004708)

Animal origin

Poultry

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

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

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

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

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

Equine

Horse (FooDB: FOOD00378)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid peroxidation (HMDB: HMDB0004708)

Biochemical process

Fatty acid metabolism (HMDB: HMDB0004708)

Cellular process

Cell signaling (HMDB: HMDB0004708)

Biochemical pathway

Lipid metabolism pathway (HMDB: HMDB0004708)

Role

Biological role

Membrane stabilizer (HMDB: HMDB0004708)

Nutrient

Nutrient (HMDB: HMDB0004708)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0004708)

Emulsifier (HMDB: HMDB0004708)

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	0.16 g/L	ALOGPS
logP	3.77	ALOGPS
logP	3.25	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Acidic)	4.68	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	91.79 m³·mol⁻¹	ChemAxon
Polarizability	40.04 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	185.285	31661259
DarkChem	[M-H]-	183.719	31661259
DeepCCS	[M+H]+	191.361	30932474
DeepCCS	[M-H]-	188.965	30932474
DeepCCS	[M-2H]-	222.666	30932474
DeepCCS	[M+Na]+	197.841	30932474
AllCCS	[M+H]+	190.1	32859911
AllCCS	[M+H-H2O]+	187.4	32859911
AllCCS	[M+NH4]+	192.6	32859911
AllCCS	[M+Na]+	193.4	32859911
AllCCS	[M-H]-	184.5	32859911
AllCCS	[M+Na-2H]-	185.8	32859911
AllCCS	[M+HCOO]-	187.4	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
9,12,13-TriHOME	CCCCC[C@H](O)[C@@H](O)\C=C\[C@@H](O)CCCCCCCC(O)=O	4271.7	Standard polar	33892256
9,12,13-TriHOME	CCCCC[C@H](O)[C@@H](O)\C=C\[C@@H](O)CCCCCCCC(O)=O	2546.7	Standard non polar	33892256
9,12,13-TriHOME	CCCCC[C@H](O)[C@@H](O)\C=C\[C@@H](O)CCCCCCCC(O)=O	2701.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
9,12,13-TriHOME,1TMS,isomer #1	CCCCC[C@H](O[Si](C)(C)C)[C@@H](O)/C=C/[C@@H](O)CCCCCCCC(=O)O	2676.2	Semi standard non polar	33892256
9,12,13-TriHOME,1TMS,isomer #2	CCCCC[C@H](O)[C@H](/C=C/[C@@H](O)CCCCCCCC(=O)O)O[Si](C)(C)C	2690.5	Semi standard non polar	33892256
9,12,13-TriHOME,1TMS,isomer #3	CCCCC[C@H](O)[C@@H](O)/C=C/[C@H](CCCCCCCC(=O)O)O[Si](C)(C)C	2761.3	Semi standard non polar	33892256
9,12,13-TriHOME,1TMS,isomer #4	CCCCC[C@H](O)[C@@H](O)/C=C/[C@@H](O)CCCCCCCC(=O)O[Si](C)(C)C	2694.9	Semi standard non polar	33892256
9,12,13-TriHOME,2TMS,isomer #1	CCCCC[C@H](O[Si](C)(C)C)[C@H](/C=C/[C@@H](O)CCCCCCCC(=O)O)O[Si](C)(C)C	2702.2	Semi standard non polar	33892256
9,12,13-TriHOME,2TMS,isomer #2	CCCCC[C@H](O[Si](C)(C)C)[C@@H](O)/C=C/[C@H](CCCCCCCC(=O)O)O[Si](C)(C)C	2707.3	Semi standard non polar	33892256
9,12,13-TriHOME,2TMS,isomer #3	CCCCC[C@H](O[Si](C)(C)C)[C@@H](O)/C=C/[C@@H](O)CCCCCCCC(=O)O[Si](C)(C)C	2674.0	Semi standard non polar	33892256
9,12,13-TriHOME,2TMS,isomer #4	CCCCC[C@H](O)[C@H](/C=C/[C@H](CCCCCCCC(=O)O)O[Si](C)(C)C)O[Si](C)(C)C	2711.0	Semi standard non polar	33892256
9,12,13-TriHOME,2TMS,isomer #5	CCCCC[C@H](O)[C@H](/C=C/[C@@H](O)CCCCCCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C	2688.5	Semi standard non polar	33892256
9,12,13-TriHOME,2TMS,isomer #6	CCCCC[C@H](O)[C@@H](O)/C=C/[C@H](CCCCCCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C	2733.3	Semi standard non polar	33892256
9,12,13-TriHOME,3TMS,isomer #1	CCCCC[C@H](O[Si](C)(C)C)[C@H](/C=C/[C@H](CCCCCCCC(=O)O)O[Si](C)(C)C)O[Si](C)(C)C	2709.9	Semi standard non polar	33892256
9,12,13-TriHOME,3TMS,isomer #2	CCCCC[C@H](O[Si](C)(C)C)[C@H](/C=C/[C@@H](O)CCCCCCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C	2708.1	Semi standard non polar	33892256
9,12,13-TriHOME,3TMS,isomer #3	CCCCC[C@H](O[Si](C)(C)C)[C@@H](O)/C=C/[C@H](CCCCCCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C	2739.6	Semi standard non polar	33892256
9,12,13-TriHOME,3TMS,isomer #4	CCCCC[C@H](O)[C@H](/C=C/[C@H](CCCCCCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C)O[Si](C)(C)C	2744.7	Semi standard non polar	33892256
9,12,13-TriHOME,4TMS,isomer #1	CCCCC[C@H](O[Si](C)(C)C)[C@H](/C=C/[C@H](CCCCCCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C)O[Si](C)(C)C	2718.7	Semi standard non polar	33892256
9,12,13-TriHOME,1TBDMS,isomer #1	CCCCC[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](O)/C=C/[C@@H](O)CCCCCCCC(=O)O	2927.6	Semi standard non polar	33892256
9,12,13-TriHOME,1TBDMS,isomer #2	CCCCC[C@H](O)[C@H](/C=C/[C@@H](O)CCCCCCCC(=O)O)O[Si](C)(C)C(C)(C)C	2924.3	Semi standard non polar	33892256
9,12,13-TriHOME,1TBDMS,isomer #3	CCCCC[C@H](O)[C@@H](O)/C=C/[C@H](CCCCCCCC(=O)O)O[Si](C)(C)C(C)(C)C	2986.3	Semi standard non polar	33892256
9,12,13-TriHOME,1TBDMS,isomer #4	CCCCC[C@H](O)[C@@H](O)/C=C/[C@@H](O)CCCCCCCC(=O)O[Si](C)(C)C(C)(C)C	2945.8	Semi standard non polar	33892256
9,12,13-TriHOME,2TBDMS,isomer #1	CCCCC[C@H](O[Si](C)(C)C(C)(C)C)[C@H](/C=C/[C@@H](O)CCCCCCCC(=O)O)O[Si](C)(C)C(C)(C)C	3193.6	Semi standard non polar	33892256
9,12,13-TriHOME,2TBDMS,isomer #2	CCCCC[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](O)/C=C/[C@H](CCCCCCCC(=O)O)O[Si](C)(C)C(C)(C)C	3214.5	Semi standard non polar	33892256
9,12,13-TriHOME,2TBDMS,isomer #3	CCCCC[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](O)/C=C/[C@@H](O)CCCCCCCC(=O)O[Si](C)(C)C(C)(C)C	3191.3	Semi standard non polar	33892256
9,12,13-TriHOME,2TBDMS,isomer #4	CCCCC[C@H](O)[C@H](/C=C/[C@H](CCCCCCCC(=O)O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3199.6	Semi standard non polar	33892256
9,12,13-TriHOME,2TBDMS,isomer #5	CCCCC[C@H](O)[C@H](/C=C/[C@@H](O)CCCCCCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3197.4	Semi standard non polar	33892256
9,12,13-TriHOME,2TBDMS,isomer #6	CCCCC[C@H](O)[C@@H](O)/C=C/[C@H](CCCCCCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3233.9	Semi standard non polar	33892256
9,12,13-TriHOME,3TBDMS,isomer #1	CCCCC[C@H](O[Si](C)(C)C(C)(C)C)[C@H](/C=C/[C@H](CCCCCCCC(=O)O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3477.1	Semi standard non polar	33892256
9,12,13-TriHOME,3TBDMS,isomer #2	CCCCC[C@H](O[Si](C)(C)C(C)(C)C)[C@H](/C=C/[C@@H](O)CCCCCCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3459.4	Semi standard non polar	33892256
9,12,13-TriHOME,3TBDMS,isomer #3	CCCCC[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](O)/C=C/[C@H](CCCCCCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3489.2	Semi standard non polar	33892256
9,12,13-TriHOME,3TBDMS,isomer #4	CCCCC[C@H](O)[C@H](/C=C/[C@H](CCCCCCCC(=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	3480.8	Semi standard non polar	33892256
9,12,13-TriHOME,4TBDMS,isomer #1	CCCCC[C@H](O[Si](C)(C)C(C)(C)C)[C@H](/C=C/[C@H](CCCCCCCC(=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	3689.4	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 9,12,13-TriHOME GC-MS (Non-derivatized) - 70eV, Positive	splash10-01t9-8793000000-4ec3797bc6aecb279c19	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 9,12,13-TriHOME GC-MS (4 TMS) - 70eV, Positive	splash10-0ufs-8320956000-3d261be1a62b70fb10fb	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 9,12,13-TriHOME 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 - 9,12,13-TriHOME 10V, Positive-QTOF	splash10-03dj-0169000000-4922950b9eca14aa8455	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 9,12,13-TriHOME 20V, Positive-QTOF	splash10-00yj-6952000000-20e6d96b68b41142b124	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 9,12,13-TriHOME 40V, Positive-QTOF	splash10-00rx-9410000000-9cfd45c735431ceee09f	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 9,12,13-TriHOME 10V, Negative-QTOF	splash10-004i-0019000000-5b501130985f198d7943	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 9,12,13-TriHOME 20V, Negative-QTOF	splash10-03di-4898000000-4a8ad508f3317957828c	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 9,12,13-TriHOME 40V, Negative-QTOF	splash10-0a4i-9530000000-1cce1c79d4d82230a45f	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 9,12,13-TriHOME 10V, Positive-QTOF	splash10-03dj-0469000000-2c2d43c0fe12624575f4	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 9,12,13-TriHOME 20V, Positive-QTOF	splash10-01wb-9853000000-3ace7024fbde5e5ba76d	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 9,12,13-TriHOME 40V, Positive-QTOF	splash10-0abc-9200000000-7b4c1043326d453aea8a	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 9,12,13-TriHOME 10V, Negative-QTOF	splash10-004i-0009000000-e6b8f3955c8a17a9406f	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 9,12,13-TriHOME 20V, Negative-QTOF	splash10-01ta-2957000000-9fa930f0f182f5916c3e	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 9,12,13-TriHOME 40V, Negative-QTOF	splash10-0ika-8930000000-6a822a39ec4bb34b9d24	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.000827 +/- 0.000214 uM	Adult (>18 years old)	Not Specified	Normal	18953024	details
Blood	Detected and Quantified	0.000827 +/- 0.00021 uM	Adult (>18 years old)	Both	Normal	21359215	details
Blood	Detected and Quantified	0.00411 +/- 0.0022 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

FDB023418

KNApSAcK ID

Not Available

Chemspider ID

8034429

KEGG Compound ID

C14833

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

9858729

PDB ID

Not Available

ChEBI ID

34506

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

Funk CD, Powell WS: Release of prostaglandins and monohydroxy and trihydroxy metabolites of linoleic and arachidonic acids by adult and fetal aortae and ductus arteriosus. J Biol Chem. 1985 Jun 25;260(12):7481-8. [PubMed:3997883 ]
Funk CD, Powell WS: Metabolism of linoleic acid by prostaglandin endoperoxide synthase from adult and fetal blood vessels. Biochim Biophys Acta. 1983 Nov 1;754(1):57-71. [PubMed:6414520 ]

Showing metabocard for 9,12,13-TriHOME (HMDB0004708)

MOL for HMDB0004708 (9,12,13-TriHOME)

3D MOL for HMDB0004708 (9,12,13-TriHOME)

3D SDF for HMDB0004708 (9,12,13-TriHOME)

3D-SDF for HMDB0004708 (9,12,13-TriHOME)

PDB for HMDB0004708 (9,12,13-TriHOME)

3D PDB for HMDB0004708 (9,12,13-TriHOME)

SMILES for HMDB0004708 (9,12,13-TriHOME)

INCHI for HMDB0004708 (9,12,13-TriHOME)

Structure for HMDB0004708 (9,12,13-TriHOME)

3D Structure for HMDB0004708 (9,12,13-TriHOME)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra