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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2008-09-15 09:54:59 UTC

Update Date

2021-09-14 15:46:28 UTC

HMDB ID

HMDB0010203

Secondary Accession Numbers

HMDB10203

Metabolite Identification

Common Name

13-HOTE

Description

13-HOTE belongs to the class of organic compounds known as lineolic acids and derivatives. These are derivatives of lineolic acid. Lineolic acid is a polyunsaturated omega-6 18 carbon long fatty acid, with two CC double bonds at the 9- and 12-positions. Thus, 13-HOTE is considered to be an octadecanoid. Based on a literature review a small amount of articles have been published on 13-HOTE.

Structure

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

HMDB0010203
     RDKit          3D
13-HOTE
 51 50  0  0  0  0  0  0  0  0999 V2000
    8.0238    1.1527    1.1824 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7824    1.0641    0.3134 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5459    0.8777    1.0642 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7708   -0.1693    0.9148 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0988   -1.2468   -0.0320 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0613   -1.4402   -1.1176 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8566   -0.3346   -1.9037 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7790   -1.9704   -0.5993 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6039   -1.3963   -0.9199 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4101   -1.9655   -0.3823 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7916   -1.4806   -0.6358 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0112   -0.3180   -1.4889 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6509    0.8209   -0.8252 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0403    0.7899   -0.3302 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4538   -0.2070    0.6676 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8973    0.0431    1.1286 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8920   -0.0362    0.0142 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3031    0.1843    0.5461 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4280    1.5071    1.1701 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0327    1.7323    2.3367 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0085    2.5198    0.4160 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5486    0.1662    1.0746 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8096    1.4248    2.2127 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7577    1.8956    0.7777 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9227    0.4518   -0.5840 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7045    2.1239   -0.1241 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1984    1.6268    1.8084 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8337   -0.2580    1.5167 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1344   -1.3005   -0.3768 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9989   -2.2056    0.5953 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4801   -2.2790   -1.7536 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4459    0.4141   -1.4436 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7303   -2.8268    0.0474 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6436   -0.5511   -1.5541 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4205   -2.8514    0.2825 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6592   -1.9886   -0.1974 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6784   -0.6338   -2.3662 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0835    0.0076   -2.0191 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5936    1.7365   -1.5061 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0047    1.1872    0.0559 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2552    1.8088    0.1257 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7670    0.7614   -1.2069 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5820   -1.2009    0.1260 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7986   -0.3227    1.5179 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1127   -0.7875    1.8520 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9520    0.9922    1.6709 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6791    0.7697   -0.7361 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8353   -1.0144   -0.4950 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4975   -0.6006    1.3044 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0584    0.0522   -0.2483 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4950    3.2749   -0.0132 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  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  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  2  0
 19 21  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  2 25  1  0
  2 26  1  0
  3 27  1  0
  4 28  1  0
  5 29  1  0
  5 30  1  0
  6 31  1  0
  7 32  1  0
  8 33  1  0
  9 34  1  0
 10 35  1  0
 11 36  1  0
 12 37  1  0
 12 38  1  0
 13 39  1  0
 13 40  1  0
 14 41  1  0
 14 42  1  0
 15 43  1  0
 15 44  1  0
 16 45  1  0
 16 46  1  0
 17 47  1  0
 17 48  1  0
 18 49  1  0
 18 50  1  0
 21 51  1  0
M  END


  Mrv0541 02241200322D          

 21 20  0  0  0  0            999 V2000
    6.4362   -9.0943    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2612   -9.0943    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6737   -9.8088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7362   -6.2364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9112   -6.2364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4987   -9.8088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4987   -6.9509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9112   -9.0943    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9112   -7.6654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4987   -8.3799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6737   -8.3799    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.3863   -7.6655    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2116   -7.6655    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6237   -8.3799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4490   -8.3799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8616   -9.0943    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6863   -9.0943    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0990   -9.8088    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.0990   -8.3799    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.9738   -6.9510    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1487   -6.9510    0.0000 C   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  6  2  0  0  0  0
  4  5  2  0  0  0  0
  5  7  1  0  0  0  0
  6  8  1  0  0  0  0
  7  9  2  0  0  0  0
  8 10  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  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
 17 19  2  0  0  0  0
 12 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21  4  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0010203

> <DATABASE_NAME>
hmdb

> <SMILES>
CC\C=C/CC(O)\C=C\C=C/CCCCCCCC(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C18H30O3/c1-2-3-11-14-17(19)15-12-9-7-5-4-6-8-10-13-16-18(20)21/h3,7,9,11-12,15,17,19H,2,4-6,8,10,13-14,16H2,1H3,(H,20,21)/b9-7-,11-3-,15-12+

> <INCHI_KEY>
KLLGGGQNRTVBSU-JDTPQGGVSA-N

> <FORMULA>
C18H30O3

> <MOLECULAR_WEIGHT>
294.429

> <EXACT_MASS>
294.219494826

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
36.381579705087205

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(9Z,11E,15Z)-13-hydroxyoctadeca-9,11,15-trienoic acid

> <ALOGPS_LOGP>
5.39

> <JCHEM_LOGP>
4.829144070666667

> <ALOGPS_LOGS>
-4.69

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
17.72082648669591

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.988167393780728

> <JCHEM_PKA_STRONGEST_BASIC>
-1.608710604596129

> <JCHEM_POLAR_SURFACE_AREA>
57.53

> <JCHEM_REFRACTIVITY>
91.1509

> <JCHEM_ROTATABLE_BOND_COUNT>
13

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.96e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
13-hote

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0010203
     RDKit          3D
13-HOTE
 51 50  0  0  0  0  0  0  0  0999 V2000
    8.0238    1.1527    1.1824 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7824    1.0641    0.3134 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5459    0.8777    1.0642 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7708   -0.1693    0.9148 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0988   -1.2468   -0.0320 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0613   -1.4402   -1.1176 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8566   -0.3346   -1.9037 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7790   -1.9704   -0.5993 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6039   -1.3963   -0.9199 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4101   -1.9655   -0.3823 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7916   -1.4806   -0.6358 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0112   -0.3180   -1.4889 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6509    0.8209   -0.8252 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0403    0.7899   -0.3302 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4538   -0.2070    0.6676 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8973    0.0431    1.1286 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8920   -0.0362    0.0142 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3031    0.1843    0.5461 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4280    1.5071    1.1701 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0327    1.7323    2.3367 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0085    2.5198    0.4160 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5486    0.1662    1.0746 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8096    1.4248    2.2127 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7577    1.8956    0.7777 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9227    0.4518   -0.5840 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7045    2.1239   -0.1241 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1984    1.6268    1.8084 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8337   -0.2580    1.5167 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1344   -1.3005   -0.3768 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9989   -2.2056    0.5953 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4801   -2.2790   -1.7536 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4459    0.4141   -1.4436 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7303   -2.8268    0.0474 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6436   -0.5511   -1.5541 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4205   -2.8514    0.2825 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6592   -1.9886   -0.1974 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6784   -0.6338   -2.3662 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0835    0.0076   -2.0191 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5936    1.7365   -1.5061 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0047    1.1872    0.0559 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2552    1.8088    0.1257 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7670    0.7614   -1.2069 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5820   -1.2009    0.1260 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7986   -0.3227    1.5179 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1127   -0.7875    1.8520 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9520    0.9922    1.6709 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6791    0.7697   -0.7361 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8353   -1.0144   -0.4950 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4975   -0.6006    1.3044 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0584    0.0522   -0.2483 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4950    3.2749   -0.0132 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  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  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  2  0
 19 21  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  2 25  1  0
  2 26  1  0
  3 27  1  0
  4 28  1  0
  5 29  1  0
  5 30  1  0
  6 31  1  0
  7 32  1  0
  8 33  1  0
  9 34  1  0
 10 35  1  0
 11 36  1  0
 12 37  1  0
 12 38  1  0
 13 39  1  0
 13 40  1  0
 14 41  1  0
 14 42  1  0
 15 43  1  0
 15 44  1  0
 16 45  1  0
 16 46  1  0
 17 47  1  0
 17 48  1  0
 18 49  1  0
 18 50  1  0
 21 51  1  0
M  END

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      12.014 -16.976   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      13.554 -16.976   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      14.324 -18.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      18.174 -11.641   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      16.634 -11.641   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      15.864 -18.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      15.864 -12.975   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      16.634 -16.976   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      16.634 -14.309   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      15.864 -15.642   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      14.324 -15.642   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      21.254 -14.309   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      22.795 -14.309   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      23.564 -15.642   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      25.105 -15.642   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      25.875 -16.976   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      27.414 -16.976   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      28.185 -18.310   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      28.185 -15.642   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      20.484 -12.975   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      18.944 -12.975   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    6                                                       
CONECT    4    5   21                                                       
CONECT    5    4    7                                                       
CONECT    6    3    8                                                       
CONECT    7    5    9                                                       
CONECT    8    6   10                                                       
CONECT    9    7   10                                                       
CONECT   10    8    9   11                                                  
CONECT   11   10                                                            
CONECT   12   13   20                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17                                                            
CONECT   20   12   21                                                       
CONECT   21   20    4                                                       
MASTER        0    0    0    0    0    0    0    0   21    0   40    0
END

COMPND    HMDB0010203
HETATM    1  C1  UNL     1       8.024   1.153   1.182  1.00  0.00           C  
HETATM    2  C2  UNL     1       6.782   1.064   0.313  1.00  0.00           C  
HETATM    3  C3  UNL     1       5.546   0.878   1.064  1.00  0.00           C  
HETATM    4  C4  UNL     1       4.771  -0.169   0.915  1.00  0.00           C  
HETATM    5  C5  UNL     1       5.099  -1.247  -0.032  1.00  0.00           C  
HETATM    6  C6  UNL     1       4.061  -1.440  -1.118  1.00  0.00           C  
HETATM    7  O1  UNL     1       3.857  -0.335  -1.904  1.00  0.00           O  
HETATM    8  C7  UNL     1       2.779  -1.970  -0.599  1.00  0.00           C  
HETATM    9  C8  UNL     1       1.604  -1.396  -0.920  1.00  0.00           C  
HETATM   10  C9  UNL     1       0.410  -1.965  -0.382  1.00  0.00           C  
HETATM   11  C10 UNL     1      -0.792  -1.481  -0.636  1.00  0.00           C  
HETATM   12  C11 UNL     1      -1.011  -0.318  -1.489  1.00  0.00           C  
HETATM   13  C12 UNL     1      -1.651   0.821  -0.825  1.00  0.00           C  
HETATM   14  C13 UNL     1      -3.040   0.790  -0.330  1.00  0.00           C  
HETATM   15  C14 UNL     1      -3.454  -0.207   0.668  1.00  0.00           C  
HETATM   16  C15 UNL     1      -4.897   0.043   1.129  1.00  0.00           C  
HETATM   17  C16 UNL     1      -5.892  -0.036   0.014  1.00  0.00           C  
HETATM   18  C17 UNL     1      -7.303   0.184   0.546  1.00  0.00           C  
HETATM   19  C18 UNL     1      -7.428   1.507   1.170  1.00  0.00           C  
HETATM   20  O2  UNL     1      -7.033   1.732   2.337  1.00  0.00           O  
HETATM   21  O3  UNL     1      -8.009   2.520   0.416  1.00  0.00           O  
HETATM   22  H1  UNL     1       8.549   0.166   1.075  1.00  0.00           H  
HETATM   23  H2  UNL     1       7.810   1.425   2.213  1.00  0.00           H  
HETATM   24  H3  UNL     1       8.758   1.896   0.778  1.00  0.00           H  
HETATM   25  H4  UNL     1       6.923   0.452  -0.584  1.00  0.00           H  
HETATM   26  H5  UNL     1       6.705   2.124  -0.124  1.00  0.00           H  
HETATM   27  H6  UNL     1       5.198   1.627   1.808  1.00  0.00           H  
HETATM   28  H7  UNL     1       3.834  -0.258   1.517  1.00  0.00           H  
HETATM   29  H8  UNL     1       6.134  -1.301  -0.377  1.00  0.00           H  
HETATM   30  H9  UNL     1       4.999  -2.206   0.595  1.00  0.00           H  
HETATM   31  H10 UNL     1       4.480  -2.279  -1.754  1.00  0.00           H  
HETATM   32  H11 UNL     1       3.446   0.414  -1.444  1.00  0.00           H  
HETATM   33  H12 UNL     1       2.730  -2.827   0.047  1.00  0.00           H  
HETATM   34  H13 UNL     1       1.644  -0.551  -1.554  1.00  0.00           H  
HETATM   35  H14 UNL     1       0.420  -2.851   0.282  1.00  0.00           H  
HETATM   36  H15 UNL     1      -1.659  -1.989  -0.197  1.00  0.00           H  
HETATM   37  H16 UNL     1      -1.678  -0.634  -2.366  1.00  0.00           H  
HETATM   38  H17 UNL     1      -0.084   0.008  -2.019  1.00  0.00           H  
HETATM   39  H18 UNL     1      -1.594   1.737  -1.506  1.00  0.00           H  
HETATM   40  H19 UNL     1      -1.005   1.187   0.056  1.00  0.00           H  
HETATM   41  H20 UNL     1      -3.255   1.809   0.126  1.00  0.00           H  
HETATM   42  H21 UNL     1      -3.767   0.761  -1.207  1.00  0.00           H  
HETATM   43  H22 UNL     1      -3.582  -1.201   0.126  1.00  0.00           H  
HETATM   44  H23 UNL     1      -2.799  -0.323   1.518  1.00  0.00           H  
HETATM   45  H24 UNL     1      -5.113  -0.788   1.852  1.00  0.00           H  
HETATM   46  H25 UNL     1      -4.952   0.992   1.671  1.00  0.00           H  
HETATM   47  H26 UNL     1      -5.679   0.770  -0.736  1.00  0.00           H  
HETATM   48  H27 UNL     1      -5.835  -1.014  -0.495  1.00  0.00           H  
HETATM   49  H28 UNL     1      -7.497  -0.601   1.304  1.00  0.00           H  
HETATM   50  H29 UNL     1      -8.058   0.052  -0.248  1.00  0.00           H  
HETATM   51  H30 UNL     1      -7.495   3.275  -0.013  1.00  0.00           H  
CONECT    1    2   22   23   24
CONECT    2    3   25   26
CONECT    3    4    4   27
CONECT    4    5   28
CONECT    5    6   29   30
CONECT    6    7    8   31
CONECT    7   32
CONECT    8    9    9   33
CONECT    9   10   34
CONECT   10   11   11   35
CONECT   11   12   36
CONECT   12   13   37   38
CONECT   13   14   39   40
CONECT   14   15   41   42
CONECT   15   16   43   44
CONECT   16   17   45   46
CONECT   17   18   47   48
CONECT   18   19   49   50
CONECT   19   20   20   21
CONECT   21   51
END

HMDB0010203
     RDKit          3D
13-HOTE
 51 50  0  0  0  0  0  0  0  0999 V2000
    8.0238    1.1527    1.1824 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7824    1.0641    0.3134 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5459    0.8777    1.0642 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7708   -0.1693    0.9148 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0988   -1.2468   -0.0320 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0613   -1.4402   -1.1176 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8566   -0.3346   -1.9037 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7790   -1.9704   -0.5993 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6039   -1.3963   -0.9199 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4101   -1.9655   -0.3823 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7916   -1.4806   -0.6358 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0112   -0.3180   -1.4889 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6509    0.8209   -0.8252 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0403    0.7899   -0.3302 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4538   -0.2070    0.6676 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8973    0.0431    1.1286 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8920   -0.0362    0.0142 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3031    0.1843    0.5461 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4280    1.5071    1.1701 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0327    1.7323    2.3367 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0085    2.5198    0.4160 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5486    0.1662    1.0746 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8096    1.4248    2.2127 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7577    1.8956    0.7777 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9227    0.4518   -0.5840 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7045    2.1239   -0.1241 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1984    1.6268    1.8084 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8337   -0.2580    1.5167 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1344   -1.3005   -0.3768 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9989   -2.2056    0.5953 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4801   -2.2790   -1.7536 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4459    0.4141   -1.4436 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7303   -2.8268    0.0474 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6436   -0.5511   -1.5541 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4205   -2.8514    0.2825 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6592   -1.9886   -0.1974 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6784   -0.6338   -2.3662 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0835    0.0076   -2.0191 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5936    1.7365   -1.5061 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0047    1.1872    0.0559 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2552    1.8088    0.1257 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7670    0.7614   -1.2069 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5820   -1.2009    0.1260 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7986   -0.3227    1.5179 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1127   -0.7875    1.8520 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9520    0.9922    1.6709 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6791    0.7697   -0.7361 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8353   -1.0144   -0.4950 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4975   -0.6006    1.3044 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0584    0.0522   -0.2483 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4950    3.2749   -0.0132 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  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  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  2  0
 19 21  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  2 25  1  0
  2 26  1  0
  3 27  1  0
  4 28  1  0
  5 29  1  0
  5 30  1  0
  6 31  1  0
  7 32  1  0
  8 33  1  0
  9 34  1  0
 10 35  1  0
 11 36  1  0
 12 37  1  0
 12 38  1  0
 13 39  1  0
 13 40  1  0
 14 41  1  0
 14 42  1  0
 15 43  1  0
 15 44  1  0
 16 45  1  0
 16 46  1  0
 17 47  1  0
 17 48  1  0
 18 49  1  0
 18 50  1  0
 21 51  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
13-Hydroxy-9Z,11E,15Z-octadecatrienoic acid	ChEBI
13-OH-9Z,11E,15Z-Octadecatrienoic acid	ChEBI
13-Hydroxy-9Z,11E,15Z-octadecatrienoate	Generator
13-OH-9Z,11E,15Z-Octadecatrienoate	Generator
13-Hydroxyoctadecatrienic acid	MeSH
13-HOTE	ChEBI

Chemical Formula

C₁₈H₃₀O₃

Average Molecular Weight

294.429

Monoisotopic Molecular Weight

294.219494826

IUPAC Name

(9Z,11E,15Z)-13-hydroxyoctadeca-9,11,15-trienoic acid

Traditional Name

13-hote

CAS Registry Number

Not Available

SMILES

CC\C=C/CC(O)\C=C\C=C/CCCCCCCC(O)=O

InChI Identifier

InChI=1S/C18H30O3/c1-2-3-11-14-17(19)15-12-9-7-5-4-6-8-10-13-16-18(20)21/h3,7,9,11-12,15,17,19H,2,4-6,8,10,13-14,16H2,1H3,(H,20,21)/b9-7-,11-3-,15-12+

InChI Key

KLLGGGQNRTVBSU-JDTPQGGVSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as lineolic acids and derivatives. These are derivatives of lineolic acid. Lineolic acid is a polyunsaturated omega-6 18 carbon long fatty acid, with two CC double bonds at the 9- and 12-positions.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Lineolic acids and derivatives

Direct Parent

Lineolic acids and derivatives

Alternative Parents

Substituents

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

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

hydroxy fatty acid (CHEBI:72641 )
HOTrE (CHEBI:72641 )
Other Octadecanoids (LMFA02000029 )

Ontology

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

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

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.006 g/L	ALOGPS
logP	5.39	ALOGPS
logP	4.83	ChemAxon
logS	-4.7	ALOGPS
pKa (Strongest Acidic)	4.99	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	13	ChemAxon
Refractivity	91.15 m³·mol⁻¹	ChemAxon
Polarizability	36.38 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]+	178.899	31661259
DarkChem	[M-H]-	178.536	31661259
DeepCCS	[M+H]+	177.976	30932474
DeepCCS	[M-H]-	175.618	30932474
DeepCCS	[M-2H]-	208.505	30932474
DeepCCS	[M+Na]+	184.07	30932474
AllCCS	[M+H]+	179.4	32859911
AllCCS	[M+H-H2O]+	176.3	32859911
AllCCS	[M+NH4]+	182.2	32859911
AllCCS	[M+Na]+	183.0	32859911
AllCCS	[M-H]-	178.9	32859911
AllCCS	[M+Na-2H]-	180.4	32859911
AllCCS	[M+HCOO]-	182.2	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
13-HOTE	CC\C=C/CC(O)\C=C\C=C/CCCCCCCC(O)=O	3911.9	Standard polar	33892256
13-HOTE	CC\C=C/CC(O)\C=C\C=C/CCCCCCCC(O)=O	2291.0	Standard non polar	33892256
13-HOTE	CC\C=C/CC(O)\C=C\C=C/CCCCCCCC(O)=O	2397.5	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
13-HOTE,1TMS,isomer #1	CC/C=C\CC(/C=C/C=C\CCCCCCCC(=O)O)O[Si](C)(C)C	2561.3	Semi standard non polar	33892256
13-HOTE,1TMS,isomer #2	CC/C=C\CC(O)/C=C/C=C\CCCCCCCC(=O)O[Si](C)(C)C	2473.9	Semi standard non polar	33892256
13-HOTE,2TMS,isomer #1	CC/C=C\CC(/C=C/C=C\CCCCCCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C	2534.6	Semi standard non polar	33892256
13-HOTE,1TBDMS,isomer #1	CC/C=C\CC(/C=C/C=C\CCCCCCCC(=O)O)O[Si](C)(C)C(C)(C)C	2804.2	Semi standard non polar	33892256
13-HOTE,1TBDMS,isomer #2	CC/C=C\CC(O)/C=C/C=C\CCCCCCCC(=O)O[Si](C)(C)C(C)(C)C	2716.8	Semi standard non polar	33892256
13-HOTE,2TBDMS,isomer #1	CC/C=C\CC(/C=C/C=C\CCCCCCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3023.1	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 - 13-HOTE GC-MS (Non-derivatized) - 70eV, Positive	splash10-00mo-9660000000-cdd31a587f020c6bb71f	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 13-HOTE GC-MS (2 TMS) - 70eV, Positive	splash10-0109-9544200000-b0a869f13b7e4fa48338	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 13-HOTE 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 - 13-HOTE 10V, Positive-QTOF	splash10-004i-0090000000-746f819f93600145d24c	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 13-HOTE 20V, Positive-QTOF	splash10-05r1-3590000000-b132154678fe02b12c68	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 13-HOTE 40V, Positive-QTOF	splash10-00kr-9620000000-83daf6b2d2d82029206d	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 13-HOTE 10V, Negative-QTOF	splash10-0006-0090000000-901bbdc98a5faa93989d	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 13-HOTE 20V, Negative-QTOF	splash10-004l-1090000000-ef28369e562e3118852d	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 13-HOTE 40V, Negative-QTOF	splash10-0a4l-9220000000-ce8f9d891009dab59be9	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 13-HOTE 10V, Positive-QTOF	splash10-004i-0590000000-bb484c38b00b61a4c5c1	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 13-HOTE 20V, Positive-QTOF	splash10-0561-3920000000-0a0eff6d89655b3e7e3a	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 13-HOTE 40V, Positive-QTOF	splash10-067i-9700000000-dd60260108f968b4a153	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 13-HOTE 10V, Negative-QTOF	splash10-002f-0090000000-e447b375f3a269ef2976	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 13-HOTE 20V, Negative-QTOF	splash10-004l-1390000000-d48b71d8fb0d418ae2de	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 13-HOTE 40V, Negative-QTOF	splash10-0006-9310000000-070b30fb068bd05ccdb9	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane (predicted from logP)

Biospecimen Locations

Blood
Feces

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	0.000493 +/- 0.000017 uM	Adult (>18 years old)	Both	Normal	20671299	details
Blood	Detected and Quantified	0.00190 +/- 0.000207 uM	Adult (>18 years old)	Not Specified	Normal	18953024	details
Blood	Detected and Quantified	0.0019 +/- 0.00021 uM	Adult (>18 years old)	Both	Normal	21359215	details
Blood	Detected and Quantified	0.00111 +/- 0.00074 uM	Adult (>18 years old)	Both	Normal	21359215	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	29808030	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

FDB027358

KNApSAcK ID

Not Available

Chemspider ID

8645139

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10469728

PDB ID

Not Available

ChEBI ID

72641

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

Collins JF, Hu Z, Ranganathan PN, Feng D, Garrick LM, Garrick MD, Browne RW: Induction of arachidonate 12-lipoxygenase (Alox15) in intestine of iron-deficient rats correlates with the production of biologically active lipid mediators. Am J Physiol Gastrointest Liver Physiol. 2008 Apr;294(4):G948-62. doi: 10.1152/ajpgi.00274.2007. Epub 2008 Feb 7. [PubMed:18258795 ]

Showing metabocard for 13-HOTE (HMDB0010203)

MOL for HMDB0010203 (13-HOTE)

3D MOL for HMDB0010203 (13-HOTE)

3D SDF for HMDB0010203 (13-HOTE)

3D-SDF for HMDB0010203 (13-HOTE)

PDB for HMDB0010203 (13-HOTE)

3D PDB for HMDB0010203 (13-HOTE)

SMILES for HMDB0010203 (13-HOTE)

INCHI for HMDB0010203 (13-HOTE)

Structure for HMDB0010203 (13-HOTE)

3D Structure for HMDB0010203 (13-HOTE)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra