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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2008-09-15 09:55:20 UTC

Update Date

2020-02-26 21:33:18 UTC

HMDB ID

HMDB0010224

Secondary Accession Numbers

HMDB10224

Metabolite Identification

Common Name

9-HOTE

Description

9-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. Based on a literature review very few articles have been published on 9-HOTE.

Structure

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

HMDB0010224
     RDKit          3D
9-HOTE
 51 50  0  0  0  0  0  0  0  0999 V2000
   -7.2992    0.4870   -1.5614 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1384   -0.3535   -2.0927 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5642   -1.0703   -0.9559 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3277   -0.9438   -0.5650 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3303   -0.0703   -1.2001 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8625    0.9376   -0.1439 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2621    0.2351    0.9942 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9901    0.4329    1.3712 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4789   -0.3053    2.5092 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7508   -0.1914    2.9670 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1491   -0.9510    4.0786 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7305    0.7191    2.3378 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9448   -0.1071    1.9669 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6933   -1.2069    1.0023 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1904   -0.7962   -0.3406 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1471    0.1321   -1.0833 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4451   -0.5724   -1.2771 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4751    0.2443   -2.0079 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8363    1.4995   -1.3443 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6913    2.2291   -1.9107 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3216    1.9603   -0.1450 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8364    1.2654   -0.9213 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7993    0.9619   -2.4185 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9700   -0.1143   -0.9273 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5456   -1.1006   -2.8138 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4978    0.3315   -2.6356 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2216   -1.7558   -0.4024 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9982   -1.5237    0.2924 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6355    0.4531   -2.1004 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4319   -0.7177   -1.4056 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8050    1.4256    0.2243 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2443    1.7304   -0.5646 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8319   -0.4717    1.5739 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4300    1.1411    0.7877 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1412   -1.0193    3.0497 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5078   -1.0589    4.8712 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0963    1.4053    3.1520 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3726    1.2955    1.4921 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3095   -0.5610    2.9328 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7858    0.5326    1.6284 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5565   -1.9075    0.9689 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8647   -1.8365    1.4523 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0626   -1.7558   -0.9278 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2164   -0.3250   -0.2557 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6581    0.2971   -2.0872 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2008    1.0517   -0.4962 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8159   -0.9953   -0.3358 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2347   -1.4613   -1.9420 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4117   -0.3884   -2.0249 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2196    0.3855   -3.0773 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9536    2.4071    0.5055 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
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 10 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
  6 32  1  0
  7 33  1  0
  8 34  1  0
  9 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 02241200332D          

 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
   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
   10.1267   -5.5888    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  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
 11 12  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
 16 18  2  0  0  0  0
 11 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20  4  1  0  0  0  0
  4 21  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0010224

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C18H30O3/c1-2-3-4-5-6-8-11-14-17(19)15-12-9-7-10-13-16-18(20)21/h3-4,8,11,14,19H,2,5-7,9-10,12-13,15-16H2,1H3,(H,20,21)/b4-3-,11-8+,17-14+

> <INCHI_KEY>
YUPHIKSLGBATJK-OBKPXJAFSA-N

> <FORMULA>
C18H30O3

> <MOLECULAR_WEIGHT>
294.429

> <EXACT_MASS>
294.219494826

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
35.67958344144132

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
5.50

> <JCHEM_LOGP>
5.233200778666665

> <ALOGPS_LOGS>
-4.75

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
10.436249122424883

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.645822963528218

> <JCHEM_PKA_STRONGEST_BASIC>
-4.8474752739163245

> <JCHEM_POLAR_SURFACE_AREA>
57.53

> <JCHEM_REFRACTIVITY>
91.68169999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
13

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
5.24e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
9-hote

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0010224
     RDKit          3D
9-HOTE
 51 50  0  0  0  0  0  0  0  0999 V2000
   -7.2992    0.4870   -1.5614 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1384   -0.3535   -2.0927 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5642   -1.0703   -0.9559 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3277   -0.9438   -0.5650 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3303   -0.0703   -1.2001 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8625    0.9376   -0.1439 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2621    0.2351    0.9942 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9901    0.4329    1.3712 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4789   -0.3053    2.5092 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7508   -0.1914    2.9670 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1491   -0.9510    4.0786 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7305    0.7191    2.3378 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9448   -0.1071    1.9669 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6933   -1.2069    1.0023 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1904   -0.7962   -0.3406 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1471    0.1321   -1.0833 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4451   -0.5724   -1.2771 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4751    0.2443   -2.0079 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8363    1.4995   -1.3443 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6913    2.2291   -1.9107 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3216    1.9603   -0.1450 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8364    1.2654   -0.9213 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7993    0.9619   -2.4185 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9700   -0.1143   -0.9273 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5456   -1.1006   -2.8138 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4978    0.3315   -2.6356 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2216   -1.7558   -0.4024 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9982   -1.5237    0.2924 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6355    0.4531   -2.1004 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4319   -0.7177   -1.4056 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8050    1.4256    0.2243 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2443    1.7304   -0.5646 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8319   -0.4717    1.5739 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4300    1.1411    0.7877 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1412   -1.0193    3.0497 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5078   -1.0589    4.8712 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0963    1.4053    3.1520 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3726    1.2955    1.4921 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3095   -0.5610    2.9328 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7858    0.5326    1.6284 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5565   -1.9075    0.9689 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8647   -1.8365    1.4523 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0626   -1.7558   -0.9278 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2164   -0.3250   -0.2557 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6581    0.2971   -2.0872 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2008    1.0517   -0.4962 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8159   -0.9953   -0.3358 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2347   -1.4613   -1.9420 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4117   -0.3884   -2.0249 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2196    0.3855   -3.0773 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9536    2.4071    0.5055 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
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 10 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
  6 32  1  0
  7 33  1  0
  8 34  1  0
  9 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  C   UNK     0      21.254 -14.309   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      22.795 -14.309   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      23.564 -15.642   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      25.105 -15.642   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      25.875 -16.976   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      27.414 -16.976   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      28.185 -18.310   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      28.185 -15.642   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      20.484 -12.975   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      18.944 -12.975   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      18.903 -10.432   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    6                                                       
CONECT    4    5   20   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                                                       
CONECT   11   12   19                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16                                                            
CONECT   19   11   20                                                       
CONECT   20   19    4                                                       
CONECT   21    4                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   40    0
END

COMPND    HMDB0010224
HETATM    1  C1  UNL     1      -7.299   0.487  -1.561  1.00  0.00           C  
HETATM    2  C2  UNL     1      -6.138  -0.353  -2.093  1.00  0.00           C  
HETATM    3  C3  UNL     1      -5.564  -1.070  -0.956  1.00  0.00           C  
HETATM    4  C4  UNL     1      -4.328  -0.944  -0.565  1.00  0.00           C  
HETATM    5  C5  UNL     1      -3.330  -0.070  -1.200  1.00  0.00           C  
HETATM    6  C6  UNL     1      -2.862   0.938  -0.144  1.00  0.00           C  
HETATM    7  C7  UNL     1      -2.262   0.235   0.994  1.00  0.00           C  
HETATM    8  C8  UNL     1      -0.990   0.433   1.371  1.00  0.00           C  
HETATM    9  C9  UNL     1      -0.479  -0.305   2.509  1.00  0.00           C  
HETATM   10  C10 UNL     1       0.751  -0.191   2.967  1.00  0.00           C  
HETATM   11  O1  UNL     1       1.149  -0.951   4.079  1.00  0.00           O  
HETATM   12  C11 UNL     1       1.731   0.719   2.338  1.00  0.00           C  
HETATM   13  C12 UNL     1       2.945  -0.107   1.967  1.00  0.00           C  
HETATM   14  C13 UNL     1       2.693  -1.207   1.002  1.00  0.00           C  
HETATM   15  C14 UNL     1       2.190  -0.796  -0.341  1.00  0.00           C  
HETATM   16  C15 UNL     1       3.147   0.132  -1.083  1.00  0.00           C  
HETATM   17  C16 UNL     1       4.445  -0.572  -1.277  1.00  0.00           C  
HETATM   18  C17 UNL     1       5.475   0.244  -2.008  1.00  0.00           C  
HETATM   19  C18 UNL     1       5.836   1.500  -1.344  1.00  0.00           C  
HETATM   20  O2  UNL     1       6.691   2.229  -1.911  1.00  0.00           O  
HETATM   21  O3  UNL     1       5.322   1.960  -0.145  1.00  0.00           O  
HETATM   22  H1  UNL     1      -6.836   1.265  -0.921  1.00  0.00           H  
HETATM   23  H2  UNL     1      -7.799   0.962  -2.419  1.00  0.00           H  
HETATM   24  H3  UNL     1      -7.970  -0.114  -0.927  1.00  0.00           H  
HETATM   25  H4  UNL     1      -6.546  -1.101  -2.814  1.00  0.00           H  
HETATM   26  H5  UNL     1      -5.498   0.331  -2.636  1.00  0.00           H  
HETATM   27  H6  UNL     1      -6.222  -1.756  -0.402  1.00  0.00           H  
HETATM   28  H7  UNL     1      -3.998  -1.524   0.292  1.00  0.00           H  
HETATM   29  H8  UNL     1      -3.636   0.453  -2.100  1.00  0.00           H  
HETATM   30  H9  UNL     1      -2.432  -0.718  -1.406  1.00  0.00           H  
HETATM   31  H10 UNL     1      -3.805   1.426   0.224  1.00  0.00           H  
HETATM   32  H11 UNL     1      -2.244   1.730  -0.565  1.00  0.00           H  
HETATM   33  H12 UNL     1      -2.832  -0.472   1.574  1.00  0.00           H  
HETATM   34  H13 UNL     1      -0.430   1.141   0.788  1.00  0.00           H  
HETATM   35  H14 UNL     1      -1.141  -1.019   3.050  1.00  0.00           H  
HETATM   36  H15 UNL     1       0.508  -1.059   4.871  1.00  0.00           H  
HETATM   37  H16 UNL     1       2.096   1.405   3.152  1.00  0.00           H  
HETATM   38  H17 UNL     1       1.373   1.295   1.492  1.00  0.00           H  
HETATM   39  H18 UNL     1       3.309  -0.561   2.933  1.00  0.00           H  
HETATM   40  H19 UNL     1       3.786   0.533   1.628  1.00  0.00           H  
HETATM   41  H20 UNL     1       3.556  -1.907   0.969  1.00  0.00           H  
HETATM   42  H21 UNL     1       1.865  -1.836   1.452  1.00  0.00           H  
HETATM   43  H22 UNL     1       2.063  -1.756  -0.928  1.00  0.00           H  
HETATM   44  H23 UNL     1       1.216  -0.325  -0.256  1.00  0.00           H  
HETATM   45  H24 UNL     1       2.658   0.297  -2.087  1.00  0.00           H  
HETATM   46  H25 UNL     1       3.201   1.052  -0.496  1.00  0.00           H  
HETATM   47  H26 UNL     1       4.816  -0.995  -0.336  1.00  0.00           H  
HETATM   48  H27 UNL     1       4.235  -1.461  -1.942  1.00  0.00           H  
HETATM   49  H28 UNL     1       6.412  -0.388  -2.025  1.00  0.00           H  
HETATM   50  H29 UNL     1       5.220   0.386  -3.077  1.00  0.00           H  
HETATM   51  H30 UNL     1       5.954   2.407   0.506  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   31   32
CONECT    7    8    8   33
CONECT    8    9   34
CONECT    9   10   10   35
CONECT   10   11   12
CONECT   11   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

HMDB0010224
     RDKit          3D
9-HOTE
 51 50  0  0  0  0  0  0  0  0999 V2000
   -7.2992    0.4870   -1.5614 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1384   -0.3535   -2.0927 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5642   -1.0703   -0.9559 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3277   -0.9438   -0.5650 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3303   -0.0703   -1.2001 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8625    0.9376   -0.1439 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2621    0.2351    0.9942 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9901    0.4329    1.3712 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4789   -0.3053    2.5092 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7508   -0.1914    2.9670 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1491   -0.9510    4.0786 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7305    0.7191    2.3378 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9448   -0.1071    1.9669 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6933   -1.2069    1.0023 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1904   -0.7962   -0.3406 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1471    0.1321   -1.0833 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4451   -0.5724   -1.2771 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4751    0.2443   -2.0079 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8363    1.4995   -1.3443 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6913    2.2291   -1.9107 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3216    1.9603   -0.1450 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8364    1.2654   -0.9213 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7993    0.9619   -2.4185 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9700   -0.1143   -0.9273 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5456   -1.1006   -2.8138 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4978    0.3315   -2.6356 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2216   -1.7558   -0.4024 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9982   -1.5237    0.2924 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6355    0.4531   -2.1004 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4319   -0.7177   -1.4056 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8050    1.4256    0.2243 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2443    1.7304   -0.5646 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8319   -0.4717    1.5739 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4300    1.1411    0.7877 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1412   -1.0193    3.0497 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5078   -1.0589    4.8712 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0963    1.4053    3.1520 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3726    1.2955    1.4921 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3095   -0.5610    2.9328 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7858    0.5326    1.6284 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5565   -1.9075    0.9689 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8647   -1.8365    1.4523 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0626   -1.7558   -0.9278 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2164   -0.3250   -0.2557 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6581    0.2971   -2.0872 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2008    1.0517   -0.4962 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8159   -0.9953   -0.3358 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2347   -1.4613   -1.9420 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4117   -0.3884   -2.0249 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2196    0.3855   -3.0773 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9536    2.4071    0.5055 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
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 10 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
  6 32  1  0
  7 33  1  0
  8 34  1  0
  9 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
9-Hydroxy-10,12,15(e,Z,Z) octadecatrienoate	HMDB
9-Hydroxy-10,12,15(e,Z,Z) octadecatrienoic acid	HMDB
(9E,11E,15Z)-9-Hydroxyoctadeca-9,11,15-trienoate	HMDB

Chemical Formula

C₁₈H₃₀O₃

Average Molecular Weight

294.429

Monoisotopic Molecular Weight

294.219494826

IUPAC Name

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

Traditional Name

9-hote

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C18H30O3/c1-2-3-4-5-6-8-11-14-17(19)15-12-9-7-10-13-16-18(20)21/h3-4,8,11,14,19H,2,5-7,9-10,12-13,15-16H2,1H3,(H,20,21)/b4-3-,11-8+,17-14+

InChI Key

YUPHIKSLGBATJK-OBKPXJAFSA-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
Monocarboxylic acid or derivatives
Enol
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 18953024)

Cellular substructure

Membrane (HMDB: HMDB0010224)

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

Equine

Horse (FooDB: FOOD00378)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

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

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

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

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

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

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.0052 g/L	ALOGPS
logP	5.5	ALOGPS
logP	5.23	ChemAxon
logS	-4.8	ALOGPS
pKa (Strongest Acidic)	4.65	ChemAxon
pKa (Strongest Basic)	-4.8	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	91.68 m³·mol⁻¹	ChemAxon
Polarizability	35.68 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	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
DeepCCS	[M+H]+	177.278	30932474
DeepCCS	[M-H]-	174.92	30932474
DeepCCS	[M-2H]-	207.806	30932474
DeepCCS	[M+Na]+	183.372	30932474
AllCCS	[M+H]+	179.1	32859911
AllCCS	[M+H-H2O]+	176.1	32859911
AllCCS	[M+NH4]+	181.9	32859911
AllCCS	[M+Na]+	182.7	32859911
AllCCS	[M-H]-	179.2	32859911
AllCCS	[M+Na-2H]-	180.7	32859911
AllCCS	[M+HCOO]-	182.5	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
9-HOTE	CC\C=C/CC\C=C\C=C(\O)CCCCCCCC(O)=O	3810.5	Standard polar	33892256
9-HOTE	CC\C=C/CC\C=C\C=C(\O)CCCCCCCC(O)=O	2273.5	Standard non polar	33892256
9-HOTE	CC\C=C/CC\C=C\C=C(\O)CCCCCCCC(O)=O	2438.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
9-HOTE,1TMS,isomer #1	CC/C=C\CC/C=C/C=C(\CCCCCCCC(=O)O)O[Si](C)(C)C	2588.3	Semi standard non polar	33892256
9-HOTE,1TMS,isomer #2	CC/C=C\CC/C=C/C=C(/O)CCCCCCCC(=O)O[Si](C)(C)C	2480.9	Semi standard non polar	33892256
9-HOTE,2TMS,isomer #1	CC/C=C\CC/C=C/C=C(\CCCCCCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C	2554.6	Semi standard non polar	33892256
9-HOTE,1TBDMS,isomer #1	CC/C=C\CC/C=C/C=C(\CCCCCCCC(=O)O)O[Si](C)(C)C(C)(C)C	2820.3	Semi standard non polar	33892256
9-HOTE,1TBDMS,isomer #2	CC/C=C\CC/C=C/C=C(/O)CCCCCCCC(=O)O[Si](C)(C)C(C)(C)C	2719.6	Semi standard non polar	33892256
9-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	3047.2	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 9-HOTE GC-MS (Non-derivatized) - 70eV, Positive	splash10-00r6-9760000000-05fda5b580c9a7b1b844	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 9-HOTE GC-MS (2 TMS) - 70eV, Positive	splash10-0100-9333200000-763edcdaad58689a5d77	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 9-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 - 9-HOTE 10V, Positive-QTOF	splash10-004j-0190000000-fd86c95a50a2cdf8d848	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 9-HOTE 20V, Positive-QTOF	splash10-00tb-7950000000-cab439f71c660ad7145a	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 9-HOTE 40V, Positive-QTOF	splash10-067l-9210000000-c0627a2c7ef4c0eb7663	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 9-HOTE 10V, Negative-QTOF	splash10-0006-0090000000-9042aace0eb244663bb1	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 9-HOTE 20V, Negative-QTOF	splash10-002g-1890000000-1552767794dd7d69cb5e	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 9-HOTE 40V, Negative-QTOF	splash10-0c04-6900000000-8775c9604b44ef69fe1e	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 9-HOTE 10V, Positive-QTOF	splash10-004j-1390000000-6426a769ca6218386915	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 9-HOTE 20V, Positive-QTOF	splash10-0005-9520000000-09f97a667948ee764ebd	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 9-HOTE 40V, Positive-QTOF	splash10-0apl-9200000000-4ebe1d7bd2c00578cb01	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 9-HOTE 10V, Negative-QTOF	splash10-0006-0090000000-622b0481e999bad50a59	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 9-HOTE 20V, Negative-QTOF	splash10-0096-1790000000-de2a2f85235e7f044da7	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 9-HOTE 40V, Negative-QTOF	splash10-05i3-6910000000-0328977072a39d261064	2021-09-22	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane (predicted from logP)

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	0.00198 +/- 0.000122 uM	Adult (>18 years old)	Not Specified	Normal	18953024	details
Blood	Detected and Quantified	0.00198 +/- 0.00012 uM	Adult (>18 years old)	Both	Normal	21359215	details
Blood	Detected and Quantified	0.00119 +/- 0.00091 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

FDB027377

KNApSAcK ID

Not Available

Chemspider ID

30776588

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

53480359

PDB ID

Not Available

ChEBI ID

88438

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

Not Available

Showing metabocard for 9-HOTE (HMDB0010224)

MOL for HMDB0010224 (9-HOTE)

3D MOL for HMDB0010224 (9-HOTE)

3D SDF for HMDB0010224 (9-HOTE)

3D-SDF for HMDB0010224 (9-HOTE)

PDB for HMDB0010224 (9-HOTE)

3D PDB for HMDB0010224 (9-HOTE)

SMILES for HMDB0010224 (9-HOTE)

INCHI for HMDB0010224 (9-HOTE)

Structure for HMDB0010224 (9-HOTE)

3D Structure for HMDB0010224 (9-HOTE)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra