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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2009-07-25 00:02:28 UTC

Update Date

2022-09-22 17:44:00 UTC

HMDB ID

HMDB0012535

Secondary Accession Numbers

HMDB12535

Metabolite Identification

Common Name

12S-HHT

Description

12(S)-HHTrE is an unusual product of the cyclooxygenase (COX) pathway and one of the primary arachidonic acid metabolites of the human platelet.1 It is biosynthesized by thromboxane (TX) synthesis from prostaglandin H2 (PGH2) concurrently with TXA2. The biological role of 12(S)-HHTrE is uncertain. It is avidly oxidized to 12-oxoHTrE by porcine 15-hydroxy PGDH.

Structure

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

HMDB0012535
     RDKit          3D
12S-HHT
 48 47  0  0  0  0  0  0  0  0999 V2000
   -8.0107   -0.8316    0.7734 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3226    0.4820    0.5361 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8409    0.4190    0.8222 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1256   -0.5788   -0.0255 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6699   -0.5855    0.3122 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0009    0.7464    0.0942 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.1495    1.0612   -1.2590 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5669    0.6066    0.3625 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7570    0.0200   -0.5033 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6645   -0.0901   -0.1802 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4649   -0.6726   -1.0413 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9450   -0.8195   -0.7697 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2619   -0.2280    0.5370 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1093    0.7691    0.6497 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8476    1.4354   -0.4260 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3363    1.2518   -0.1105 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5839   -0.2295   -0.0810 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0194   -0.5323    0.2211 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8218    0.4008    0.4070 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.4253   -1.8576    0.2872 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0870   -0.6845    0.5476 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6287   -1.6204    0.0904 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9455   -1.1166    1.8438 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7928    1.2309    1.2051 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5205    0.7986   -0.5054 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6865    0.1487    1.8802 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4388    1.4405    0.5765 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2296   -0.3887   -1.1136 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5162   -1.6016    0.1528 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4712   -0.9797    1.3376 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1493   -1.3127   -0.3770 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4087    1.5284    0.7513 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0671    0.2275   -1.7717 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1346    0.9807    1.2774 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1412   -0.3814   -1.4542 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0536    0.2922    0.7347 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0555   -1.0501   -1.9543 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0767   -1.9507   -0.7321 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5178   -0.4792   -1.6238 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7880   -0.6216    1.4252 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2961    1.1606    1.6691 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7048    1.0295   -1.4261 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6433    2.5308   -0.4557 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5019    1.7123    0.8744 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9020    1.7732   -0.8896 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3210   -0.6867   -1.0456 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9710   -0.6561    0.7412 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.3500   -2.0908    0.0003 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  2 24  1  0
  2 25  1  0
  3 26  1  0
  3 27  1  0
  4 28  1  0
  4 29  1  0
  5 30  1  0
  5 31  1  0
  6 32  1  1
  7 33  1  0
  8 34  1  0
  9 35  1  0
 10 36  1  0
 11 37  1  0
 12 38  1  0
 12 39  1  0
 13 40  1  0
 14 41  1  0
 15 42  1  0
 15 43  1  0
 16 44  1  0
 16 45  1  0
 17 46  1  0
 17 47  1  0
 20 48  1  0
M  END


  Mrv0541 02251208062D          

 20 19  0  0  1  0            999 V2000
    8.0403  -15.4826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4528  -14.7681    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2778  -14.7681    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6903  -14.0536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5153  -14.0536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9278  -13.3391    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   10.5153  -12.6247    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.7528  -13.3391    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1653  -14.0536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9903  -14.0536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4028  -14.7681    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2278  -14.7681    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6403  -15.4826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4653  -15.4826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8778  -14.7681    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7028  -14.7681    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1153  -14.0536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9403  -14.0536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3528  -14.7681    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.3528  -13.3391    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  6  0  0  0
  6  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 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 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0012535

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C17H28O3/c1-2-3-10-13-16(18)14-11-8-6-4-5-7-9-12-15-17(19)20/h5-8,11,14,16,18H,2-4,9-10,12-13,15H2,1H3,(H,19,20)/b7-5-,8-6+,14-11+/t16-/m0/s1

> <INCHI_KEY>
KUKJHGXXZWHSBG-WBGSEQOASA-N

> <FORMULA>
C17H28O3

> <MOLECULAR_WEIGHT>
280.4024

> <EXACT_MASS>
280.203844762

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
34.14970120106609

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(5Z,8E,10E,12S)-12-hydroxyheptadeca-5,8,10-trienoic acid

> <ALOGPS_LOGP>
4.99

> <JCHEM_LOGP>
4.384575405666666

> <ALOGPS_LOGS>
-4.28

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
17.795677863984817

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.889630655845193

> <JCHEM_PKA_STRONGEST_BASIC>
-1.5759706509493094

> <JCHEM_POLAR_SURFACE_AREA>
57.53

> <JCHEM_REFRACTIVITY>
86.5499

> <JCHEM_ROTATABLE_BOND_COUNT>
12

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.47e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
12-HHTrE

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0012535
     RDKit          3D
12S-HHT
 48 47  0  0  0  0  0  0  0  0999 V2000
   -8.0107   -0.8316    0.7734 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3226    0.4820    0.5361 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8409    0.4190    0.8222 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1256   -0.5788   -0.0255 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6699   -0.5855    0.3122 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0009    0.7464    0.0942 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.1495    1.0612   -1.2590 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5669    0.6066    0.3625 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7570    0.0200   -0.5033 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6645   -0.0901   -0.1802 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4649   -0.6726   -1.0413 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9450   -0.8195   -0.7697 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2619   -0.2280    0.5370 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1093    0.7691    0.6497 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8476    1.4354   -0.4260 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3363    1.2518   -0.1105 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5839   -0.2295   -0.0810 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0194   -0.5323    0.2211 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8218    0.4008    0.4070 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.4253   -1.8576    0.2872 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0870   -0.6845    0.5476 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6287   -1.6204    0.0904 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9455   -1.1166    1.8438 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7928    1.2309    1.2051 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5205    0.7986   -0.5054 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6865    0.1487    1.8802 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4388    1.4405    0.5765 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2296   -0.3887   -1.1136 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5162   -1.6016    0.1528 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4712   -0.9797    1.3376 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1493   -1.3127   -0.3770 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4087    1.5284    0.7513 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0671    0.2275   -1.7717 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1346    0.9807    1.2774 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1412   -0.3814   -1.4542 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0536    0.2922    0.7347 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0555   -1.0501   -1.9543 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0767   -1.9507   -0.7321 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5178   -0.4792   -1.6238 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7880   -0.6216    1.4252 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2961    1.1606    1.6691 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7048    1.0295   -1.4261 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6433    2.5308   -0.4557 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5019    1.7123    0.8744 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9020    1.7732   -0.8896 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3210   -0.6867   -1.0456 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9710   -0.6561    0.7412 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.3500   -2.0908    0.0003 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  2 24  1  0
  2 25  1  0
  3 26  1  0
  3 27  1  0
  4 28  1  0
  4 29  1  0
  5 30  1  0
  5 31  1  0
  6 32  1  1
  7 33  1  0
  8 34  1  0
  9 35  1  0
 10 36  1  0
 11 37  1  0
 12 38  1  0
 12 39  1  0
 13 40  1  0
 14 41  1  0
 15 42  1  0
 15 43  1  0
 16 44  1  0
 16 45  1  0
 17 46  1  0
 17 47  1  0
 20 48  1  0
M  END

HEADER    PROTEIN                                 25-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   25-FEB-12         0                                  
HETATM    1  C   UNK     0      15.009 -28.901   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      15.779 -27.567   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      17.319 -27.567   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      18.089 -26.233   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      19.629 -26.233   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      20.399 -24.900   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      19.629 -23.566   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      21.939 -24.900   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      22.709 -26.233   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      24.249 -26.233   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      25.019 -27.567   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      26.559 -27.567   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      27.329 -28.901   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      28.869 -28.901   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      29.639 -27.567   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      31.179 -27.567   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      31.949 -26.233   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      33.489 -26.233   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      34.259 -27.567   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      34.259 -24.900   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   38    0
END

COMPND    HMDB0012535
HETATM    1  C1  UNL     1      -8.011  -0.832   0.773  1.00  0.00           C  
HETATM    2  C2  UNL     1      -7.323   0.482   0.536  1.00  0.00           C  
HETATM    3  C3  UNL     1      -5.841   0.419   0.822  1.00  0.00           C  
HETATM    4  C4  UNL     1      -5.126  -0.579  -0.026  1.00  0.00           C  
HETATM    5  C5  UNL     1      -3.670  -0.585   0.312  1.00  0.00           C  
HETATM    6  C6  UNL     1      -3.001   0.746   0.094  1.00  0.00           C  
HETATM    7  O1  UNL     1      -3.150   1.061  -1.259  1.00  0.00           O  
HETATM    8  C7  UNL     1      -1.567   0.607   0.363  1.00  0.00           C  
HETATM    9  C8  UNL     1      -0.757   0.020  -0.503  1.00  0.00           C  
HETATM   10  C9  UNL     1       0.665  -0.090  -0.180  1.00  0.00           C  
HETATM   11  C10 UNL     1       1.465  -0.673  -1.041  1.00  0.00           C  
HETATM   12  C11 UNL     1       2.945  -0.820  -0.770  1.00  0.00           C  
HETATM   13  C12 UNL     1       3.262  -0.228   0.537  1.00  0.00           C  
HETATM   14  C13 UNL     1       4.109   0.769   0.650  1.00  0.00           C  
HETATM   15  C14 UNL     1       4.848   1.435  -0.426  1.00  0.00           C  
HETATM   16  C15 UNL     1       6.336   1.252  -0.110  1.00  0.00           C  
HETATM   17  C16 UNL     1       6.584  -0.229  -0.081  1.00  0.00           C  
HETATM   18  C17 UNL     1       8.019  -0.532   0.221  1.00  0.00           C  
HETATM   19  O2  UNL     1       8.822   0.401   0.407  1.00  0.00           O  
HETATM   20  O3  UNL     1       8.425  -1.858   0.287  1.00  0.00           O  
HETATM   21  H1  UNL     1      -9.087  -0.684   0.548  1.00  0.00           H  
HETATM   22  H2  UNL     1      -7.629  -1.620   0.090  1.00  0.00           H  
HETATM   23  H3  UNL     1      -7.945  -1.117   1.844  1.00  0.00           H  
HETATM   24  H4  UNL     1      -7.793   1.231   1.205  1.00  0.00           H  
HETATM   25  H5  UNL     1      -7.520   0.799  -0.505  1.00  0.00           H  
HETATM   26  H6  UNL     1      -5.687   0.149   1.880  1.00  0.00           H  
HETATM   27  H7  UNL     1      -5.439   1.441   0.577  1.00  0.00           H  
HETATM   28  H8  UNL     1      -5.230  -0.389  -1.114  1.00  0.00           H  
HETATM   29  H9  UNL     1      -5.516  -1.602   0.153  1.00  0.00           H  
HETATM   30  H10 UNL     1      -3.471  -0.980   1.338  1.00  0.00           H  
HETATM   31  H11 UNL     1      -3.149  -1.313  -0.377  1.00  0.00           H  
HETATM   32  H12 UNL     1      -3.409   1.528   0.751  1.00  0.00           H  
HETATM   33  H13 UNL     1      -3.067   0.227  -1.772  1.00  0.00           H  
HETATM   34  H14 UNL     1      -1.135   0.981   1.277  1.00  0.00           H  
HETATM   35  H15 UNL     1      -1.141  -0.381  -1.454  1.00  0.00           H  
HETATM   36  H16 UNL     1       1.054   0.292   0.735  1.00  0.00           H  
HETATM   37  H17 UNL     1       1.056  -1.050  -1.954  1.00  0.00           H  
HETATM   38  H18 UNL     1       3.077  -1.951  -0.732  1.00  0.00           H  
HETATM   39  H19 UNL     1       3.518  -0.479  -1.624  1.00  0.00           H  
HETATM   40  H20 UNL     1       2.788  -0.622   1.425  1.00  0.00           H  
HETATM   41  H21 UNL     1       4.296   1.161   1.669  1.00  0.00           H  
HETATM   42  H22 UNL     1       4.705   1.030  -1.426  1.00  0.00           H  
HETATM   43  H23 UNL     1       4.643   2.531  -0.456  1.00  0.00           H  
HETATM   44  H24 UNL     1       6.502   1.712   0.874  1.00  0.00           H  
HETATM   45  H25 UNL     1       6.902   1.773  -0.890  1.00  0.00           H  
HETATM   46  H26 UNL     1       6.321  -0.687  -1.046  1.00  0.00           H  
HETATM   47  H27 UNL     1       5.971  -0.656   0.741  1.00  0.00           H  
HETATM   48  H28 UNL     1       9.350  -2.091   0.000  1.00  0.00           H  
CONECT    1    2   21   22   23
CONECT    2    3   24   25
CONECT    3    4   26   27
CONECT    4    5   28   29
CONECT    5    6   30   31
CONECT    6    7    8   32
CONECT    7   33
CONECT    8    9    9   34
CONECT    9   10   35
CONECT   10   11   11   36
CONECT   11   12   37
CONECT   12   13   38   39
CONECT   13   14   14   40
CONECT   14   15   41
CONECT   15   16   42   43
CONECT   16   17   44   45
CONECT   17   18   46   47
CONECT   18   19   19   20
CONECT   20   48
END

HMDB0012535
     RDKit          3D
12S-HHT
 48 47  0  0  0  0  0  0  0  0999 V2000
   -8.0107   -0.8316    0.7734 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3226    0.4820    0.5361 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8409    0.4190    0.8222 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1256   -0.5788   -0.0255 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6699   -0.5855    0.3122 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0009    0.7464    0.0942 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.1495    1.0612   -1.2590 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5669    0.6066    0.3625 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7570    0.0200   -0.5033 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6645   -0.0901   -0.1802 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4649   -0.6726   -1.0413 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9450   -0.8195   -0.7697 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2619   -0.2280    0.5370 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1093    0.7691    0.6497 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8476    1.4354   -0.4260 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3363    1.2518   -0.1105 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5839   -0.2295   -0.0810 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0194   -0.5323    0.2211 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8218    0.4008    0.4070 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.4253   -1.8576    0.2872 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0870   -0.6845    0.5476 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6287   -1.6204    0.0904 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9455   -1.1166    1.8438 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7928    1.2309    1.2051 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5205    0.7986   -0.5054 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6865    0.1487    1.8802 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4388    1.4405    0.5765 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2296   -0.3887   -1.1136 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5162   -1.6016    0.1528 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4712   -0.9797    1.3376 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1493   -1.3127   -0.3770 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4087    1.5284    0.7513 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0671    0.2275   -1.7717 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1346    0.9807    1.2774 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1412   -0.3814   -1.4542 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0536    0.2922    0.7347 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0555   -1.0501   -1.9543 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0767   -1.9507   -0.7321 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5178   -0.4792   -1.6238 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7880   -0.6216    1.4252 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2961    1.1606    1.6691 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7048    1.0295   -1.4261 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6433    2.5308   -0.4557 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5019    1.7123    0.8744 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9020    1.7732   -0.8896 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3210   -0.6867   -1.0456 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9710   -0.6561    0.7412 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.3500   -2.0908    0.0003 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  2 24  1  0
  2 25  1  0
  3 26  1  0
  3 27  1  0
  4 28  1  0
  4 29  1  0
  5 30  1  0
  5 31  1  0
  6 32  1  1
  7 33  1  0
  8 34  1  0
  9 35  1  0
 10 36  1  0
 11 37  1  0
 12 38  1  0
 12 39  1  0
 13 40  1  0
 14 41  1  0
 15 42  1  0
 15 43  1  0
 16 44  1  0
 16 45  1  0
 17 46  1  0
 17 47  1  0
 20 48  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
12-HHTrE	ChEBI
12S-Hydroxy-5Z,8E,10E-heptadecatrienoic acid	ChEBI
(12S,5Z,8E,10E)-12-Hydroxy-5,8,10-heptadecatrienoic acid	Kegg
12S-Hydroxy-5Z,8E,10E-heptadecatrienoate	Generator
(12S,5Z,8E,10E)-12-Hydroxy-5,8,10-heptadecatrienoate	Generator
12-L-Hydroxy-5,8,10-heptadecatrienoic acid	MeSH
12-Hydroxy-5,8,10-heptadecatrienoic acid	MeSH
12-HHT	MeSH
12-Hydroxy-5,8,10-heptadecatrienoic acid, (S)-(e,Z,Z)-isomer	MeSH
12-Hydroxy-5,8,10-heptadecatrienoic acid, (e,Z,Z)-isomer	MeSH
12-Hydroxy-5,8,10-heptadecatrienoic acid, (S)-(Z,e,e)-isomer	MeSH
12-Hydroxy-5,8,10-heptadecatrienoic acid, (S)-isomer	MeSH
Hydroxyheptadecatrienoic acid	MeSH
12(S)-Hydroxy-(5Z,8Z,10E)-heptadeca-5,8,10-trienoate	HMDB
12(S)-Hydroxy-(5Z,8Z,10E)-heptadeca-5,8,10-trienoic acid	HMDB
12(S)-Hydroxy-(5Z,8Z,10E)-heptadeca-5,8,10-trienoic acid anion	HMDB
12-Hydroxyheptadecatrienoate	HMDB
12-Hydroxyheptadecatrienoic acid	HMDB
HHT	HMDB
Hydroxyheptadecatrienate	HMDB
Hydroxyheptadecatrienoate	HMDB
Hydroxyheptadecatrienoic acid anion	HMDB
12S-HHT	ChEBI

Chemical Formula

C₁₇H₂₈O₃

Average Molecular Weight

280.4024

Monoisotopic Molecular Weight

280.203844762

IUPAC Name

(5Z,8E,10E,12S)-12-hydroxyheptadeca-5,8,10-trienoic acid

Traditional Name

12-HHTrE

CAS Registry Number

54397-84-1

SMILES

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

InChI Identifier

InChI=1S/C17H28O3/c1-2-3-10-13-16(18)14-11-8-6-4-5-7-9-12-15-17(19)20/h5-8,11,14,16,18H,2-4,9-10,12-13,15H2,1H3,(H,19,20)/b7-5-,8-6+,14-11+/t16-/m0/s1

InChI Key

KUKJHGXXZWHSBG-WBGSEQOASA-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
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

12-HHTrE (CHEBI:63977 )
Hydroxy/hydroperoxyeicosatrienoic acids (LMFA03050002 )

Ontology

Not Available

Urine (HMDB: HMDB0012535)

Non-excretory biofluid

Blood (PMID: 20671299)

Cellular substructure

Extracellular (HMDB: HMDB0012535)
Membrane (HMDB: HMDB0012535)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0012535)

Source

Endogenous

Endogenous (HMDB: HMDB0012535)

Animal

Animal (HMDB: HMDB0012535)

Exogenous

Food

Food (HMDB: HMDB0012535)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid peroxidation (HMDB: HMDB0012535)

Biochemical process

Fatty acid metabolism (HMDB: HMDB0012535)

Cellular process

Cell signaling (HMDB: HMDB0012535)

Biochemical pathway

Lipid metabolism pathway (HMDB: HMDB0012535)

Role

Biological role

Membrane stabilizer (HMDB: HMDB0012535)

Nutrient

Nutrient (HMDB: HMDB0012535)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0012535)

Emulsifier (HMDB: HMDB0012535)

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	0.015 g/L	ALOGPS
logP	4.99	ALOGPS
logP	4.38	ChemAxon
logS	-4.3	ALOGPS
pKa (Strongest Acidic)	4.89	ChemAxon
pKa (Strongest Basic)	-1.6	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	57.53 Å²	ChemAxon
Rotatable Bond Count	12	ChemAxon
Refractivity	86.55 m³·mol⁻¹	ChemAxon
Polarizability	34.15 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]+	174.941	31661259
DarkChem	[M-H]-	176.331	31661259
DeepCCS	[M+H]+	175.861	30932474
DeepCCS	[M-H]-	173.503	30932474
DeepCCS	[M-2H]-	206.389	30932474
DeepCCS	[M+Na]+	181.955	30932474
AllCCS	[M+H]+	174.9	32859911
AllCCS	[M+H-H2O]+	171.7	32859911
AllCCS	[M+NH4]+	177.8	32859911
AllCCS	[M+Na]+	178.6	32859911
AllCCS	[M-H]-	174.7	32859911
AllCCS	[M+Na-2H]-	176.0	32859911
AllCCS	[M+HCOO]-	177.6	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
12S-HHT	CCCCC[C@H](O)\C=C\C=C\C\C=C/CCCC(O)=O	3785.2	Standard polar	33892256
12S-HHT	CCCCC[C@H](O)\C=C\C=C\C\C=C/CCCC(O)=O	2161.2	Standard non polar	33892256
12S-HHT	CCCCC[C@H](O)\C=C\C=C\C\C=C/CCCC(O)=O	2316.2	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
12S-HHT,1TMS,isomer #1	CCCCC[C@@H](/C=C/C=C/C/C=C\CCCC(=O)O)O[Si](C)(C)C	2426.0	Semi standard non polar	33892256
12S-HHT,1TMS,isomer #2	CCCCC[C@H](O)/C=C/C=C/C/C=C\CCCC(=O)O[Si](C)(C)C	2347.2	Semi standard non polar	33892256
12S-HHT,2TMS,isomer #1	CCCCC[C@@H](/C=C/C=C/C/C=C\CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C	2422.8	Semi standard non polar	33892256
12S-HHT,1TBDMS,isomer #1	CCCCC[C@@H](/C=C/C=C/C/C=C\CCCC(=O)O)O[Si](C)(C)C(C)(C)C	2673.6	Semi standard non polar	33892256
12S-HHT,1TBDMS,isomer #2	CCCCC[C@H](O)/C=C/C=C/C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C	2587.3	Semi standard non polar	33892256
12S-HHT,2TBDMS,isomer #1	CCCCC[C@@H](/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	2906.7	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 - 12S-HHT GC-MS (Non-derivatized) - 70eV, Positive	splash10-0596-7940000000-88adc904734528989f76	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 12S-HHT GC-MS (2 TMS) - 70eV, Positive	splash10-009i-9223100000-1505e4bf1a2b098cc662	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 12S-HHT 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 - 12S-HHT 10V, Positive-QTOF	splash10-03di-0090000000-025c6c4f9cc74b291b50	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 12S-HHT 20V, Positive-QTOF	splash10-044s-4490000000-e7b3a17b02d9bf372212	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 12S-HHT 40V, Positive-QTOF	splash10-05tf-9510000000-a08ec733ca2fb7d71708	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 12S-HHT 10V, Negative-QTOF	splash10-004i-0090000000-0cc456c0c372dc9dcfc6	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 12S-HHT 20V, Negative-QTOF	splash10-03fr-1090000000-a3df181a56e24018b9e5	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 12S-HHT 40V, Negative-QTOF	splash10-0a4l-9320000000-f4709ec871502770402e	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 12S-HHT 10V, Negative-QTOF	splash10-01t9-0090000000-901f14c9bb947096b214	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 12S-HHT 20V, Negative-QTOF	splash10-03fr-0490000000-4d3abc99004a8aa63c02	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 12S-HHT 40V, Negative-QTOF	splash10-052f-9410000000-8529271056414c39c9f7	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 12S-HHT 10V, Positive-QTOF	splash10-03di-0590000000-800b65d657b078360d45	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 12S-HHT 20V, Positive-QTOF	splash10-01wb-3920000000-6040d9c2d707a1656b95	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 12S-HHT 40V, Positive-QTOF	splash10-066v-9400000000-281fc4c65ccd705a48a1	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Blood
Urine

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	0.00203 +/- 0.000278 uM	Adult (>18 years old)	Both	Normal	20671299	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Urine	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Cancer patients undergoing total body irradiation	31424920	details

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

FDB029115

KNApSAcK ID

Not Available

Chemspider ID

4446265

KEGG Compound ID

C20388

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5283141

PDB ID

Not Available

ChEBI ID

63977

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Showing metabocard for 12S-HHT (HMDB0012535)

MOL for HMDB0012535 (12S-HHT)

3D MOL for HMDB0012535 (12S-HHT)

3D SDF for HMDB0012535 (12S-HHT)

3D-SDF for HMDB0012535 (12S-HHT)

PDB for HMDB0012535 (12S-HHT)

3D PDB for HMDB0012535 (12S-HHT)

SMILES for HMDB0012535 (12S-HHT)

INCHI for HMDB0012535 (12S-HHT)

Structure for HMDB0012535 (12S-HHT)

3D Structure for HMDB0012535 (12S-HHT)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra