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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-10 23:10:46 UTC

Update Date

2021-09-26 22:55:01 UTC

HMDB ID

HMDB0246143

Secondary Accession Numbers

None

Metabolite Identification

Common Name

13-Oxo-9,11-octadecadienoic acid

Description

13-Oxo-9,11-octadecadienoic acid, also known as 13-keto-9,11-ode or 13-KODE, 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 a significant number of articles have been published on 13-Oxo-9,11-octadecadienoic acid. This compound has been identified in human blood as reported by (PMID: 31557052 ). 13-oxo-9,11-octadecadienoic acid is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically 13-Oxo-9,11-octadecadienoic acid is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.

Structure

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

HMDB0246143
     RDKit          3D
13-Oxo-9,11-octadecadienoic acid
 51 50  0  0  0  0  0  0  0  0999 V2000
   -8.0273   -1.5973    0.4739 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8638   -0.4045   -0.4476 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4021   -0.1040   -0.7077 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7710    0.1914    0.6283 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2680    0.5110    0.4540 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7413    0.7842    1.8021 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6464    0.6867    2.7425 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4470    1.1276    2.2445 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3565    1.3019    1.6097 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1090    1.1995    0.2223 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0483    1.3982   -0.3428 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2684    1.7569    0.3605 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3768    0.7267    0.1763 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7444    0.5634   -1.2657 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8335   -0.4522   -1.4922 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0789   -0.0330   -0.7586 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2085   -1.0381   -0.9708 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4193   -0.5463   -0.2040 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5561   -1.4869   -0.3726 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4451   -2.5219   -1.0701 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.7603   -1.2319    0.2417 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1364   -1.7867    0.5240 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5881   -2.4938    0.0015 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7046   -1.4078    1.4972 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3981   -0.6480   -1.3972 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3472    0.4748    0.0364 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9450   -0.9854   -1.2022 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3526    0.7716   -1.3604 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2268    1.1107    1.0282 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8106   -0.6760    1.2929 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7901   -0.3512   -0.0603 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1711    1.3915   -0.2111 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3593    1.2759    3.3686 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4724    1.5708    2.2372 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9762    0.9290   -0.4173 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0783    1.2780   -1.4496 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6344    2.7265   -0.1098 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1424    1.9485    1.4244 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2247    1.1077    0.7810 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0369   -0.2102    0.6138 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8699    0.3643   -1.8953 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1576    1.5474   -1.6283 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9997   -0.5021   -2.5921 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5197   -1.4769   -1.1976 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3787    0.9660   -1.1300 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8857    0.0560    0.3285 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4774   -1.0554   -2.0466 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8992   -2.0506   -0.6811 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1731   -0.3689    0.8663 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7025    0.4381   -0.6471 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.9912   -0.3605    0.7021 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  2  0
  6  8  1  0
  8  9  2  3
  9 10  1  0
 10 11  2  3
 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
  3 28  1  0
  4 29  1  0
  4 30  1  0
  5 31  1  0
  5 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

  Mrv1652305221921042D          

 21 20  0  0  0  0            999 V2000
   -4.1467    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4322    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7177    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7125    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9980    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4270    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2836    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1414    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5691    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8559    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0033    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8546    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5704    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2888    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1401    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2849    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5743    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9993    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5743    1.3184    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.7138    2.5559    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9993    1.3184    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  2  1  0  0  0  0
  5  4  1  0  0  0  0
  6  4  1  0  0  0  0
  7  5  1  0  0  0  0
  8  6  1  0  0  0  0
  9  7  2  0  0  0  0
 10  8  1  0  0  0  0
 11  3  1  0  0  0  0
  9 12  1  4  0  0  0
 13 10  1  0  0  0  0
 14 11  1  0  0  0  0
 15 12  2  0  0  0  0
 16 13  1  0  0  0  0
 17 14  1  0  0  0  0
 15 17  1  4  0  0  0
 18 16  1  0  0  0  0
 19 17  2  0  0  0  0
 20 18  2  0  0  0  0
 21 18  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0246143

> <DATABASE_NAME>
hmdb

> <SMILES>
CCCCCC(=O)C=CC=CCCCCCCCC(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/h7,9,12,15H,2-6,8,10-11,13-14,16H2,1H3,(H,20,21)

> <INCHI_KEY>
JHXAZBBVQSRKJR-UHFFFAOYSA-N

> <FORMULA>
C18H30O3

> <MOLECULAR_WEIGHT>
294.429

> <EXACT_MASS>
294.219494826

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
51

> <JCHEM_AVERAGE_POLARIZABILITY>
37.31557388308441

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
13-oxooctadeca-9,11-dienoic acid

> <ALOGPS_LOGP>
5.66

> <JCHEM_LOGP>
5.602404215333333

> <ALOGPS_LOGS>
-5.35

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.988167284021987

> <JCHEM_PKA_STRONGEST_BASIC>
-4.577074788947507

> <JCHEM_POLAR_SURFACE_AREA>
54.370000000000005

> <JCHEM_REFRACTIVITY>
89.13689999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
14

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.30e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
13-oxooctadeca-9,11-dienoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0246143
     RDKit          3D
13-Oxo-9,11-octadecadienoic acid
 51 50  0  0  0  0  0  0  0  0999 V2000
   -8.0273   -1.5973    0.4739 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8638   -0.4045   -0.4476 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4021   -0.1040   -0.7077 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7710    0.1914    0.6283 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2680    0.5110    0.4540 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7413    0.7842    1.8021 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6464    0.6867    2.7425 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4470    1.1276    2.2445 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3565    1.3019    1.6097 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1090    1.1995    0.2223 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0483    1.3982   -0.3428 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2684    1.7569    0.3605 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3768    0.7267    0.1763 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7444    0.5634   -1.2657 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8335   -0.4522   -1.4922 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0789   -0.0330   -0.7586 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2085   -1.0381   -0.9708 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4193   -0.5463   -0.2040 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5561   -1.4869   -0.3726 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4451   -2.5219   -1.0701 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.7603   -1.2319    0.2417 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1364   -1.7867    0.5240 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5881   -2.4938    0.0015 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7046   -1.4078    1.4972 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3981   -0.6480   -1.3972 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3472    0.4748    0.0364 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9450   -0.9854   -1.2022 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3526    0.7716   -1.3604 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2268    1.1107    1.0282 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8106   -0.6760    1.2929 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7901   -0.3512   -0.0603 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1711    1.3915   -0.2111 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3593    1.2759    3.3686 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4724    1.5708    2.2372 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9762    0.9290   -0.4173 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0783    1.2780   -1.4496 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6344    2.7265   -0.1098 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1424    1.9485    1.4244 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2247    1.1077    0.7810 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0369   -0.2102    0.6138 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8699    0.3643   -1.8953 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1576    1.5474   -1.6283 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9997   -0.5021   -2.5921 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5197   -1.4769   -1.1976 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3787    0.9660   -1.1300 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8857    0.0560    0.3285 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4774   -1.0554   -2.0466 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8992   -2.0506   -0.6811 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1731   -0.3689    0.8663 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7025    0.4381   -0.6471 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.9912   -0.3605    0.7021 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  2  0
  6  8  1  0
  8  9  2  3
  9 10  1  0
 10 11  2  3
 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
  3 28  1  0
  4 29  1  0
  4 30  1  0
  5 31  1  0
  5 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                                 22-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   22-MAY-19         0                                  
HETATM    1  C   UNK     0      -7.740   4.771   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -6.407   4.001   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -5.073   4.771   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.930   4.001   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.596   4.771   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.264   4.771   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.263   4.001   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.597   4.001   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.929   4.771   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      10.931   4.771   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -3.739   4.001   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.595   4.001   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      12.265   4.001   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -2.406   4.771   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.262   4.771   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      13.598   4.771   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -1.072   4.001   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      14.932   4.001   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -1.072   2.461   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      16.266   4.771   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      14.932   2.461   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2   11                                                       
CONECT    4    5    6                                                       
CONECT    5    4    7                                                       
CONECT    6    4    8                                                       
CONECT    7    5    9                                                       
CONECT    8    6   10                                                       
CONECT    9    7   12                                                       
CONECT   10    8   13                                                       
CONECT   11    3   14                                                       
CONECT   12    9   15                                                       
CONECT   13   10   16                                                       
CONECT   14   11   17                                                       
CONECT   15   12   17                                                       
CONECT   16   13   18                                                       
CONECT   17   14   15   19                                                  
CONECT   18   16   20   21                                                  
CONECT   19   17                                                            
CONECT   20   18                                                            
CONECT   21   18                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   40    0
END

COMPND    HMDB0246143
HETATM    1  C1  UNL     1      -8.027  -1.597   0.474  1.00  0.00           C  
HETATM    2  C2  UNL     1      -7.864  -0.404  -0.448  1.00  0.00           C  
HETATM    3  C3  UNL     1      -6.402  -0.104  -0.708  1.00  0.00           C  
HETATM    4  C4  UNL     1      -5.771   0.191   0.628  1.00  0.00           C  
HETATM    5  C5  UNL     1      -4.268   0.511   0.454  1.00  0.00           C  
HETATM    6  C6  UNL     1      -3.741   0.784   1.802  1.00  0.00           C  
HETATM    7  O1  UNL     1      -4.646   0.687   2.743  1.00  0.00           O  
HETATM    8  C7  UNL     1      -2.447   1.128   2.245  1.00  0.00           C  
HETATM    9  C8  UNL     1      -1.356   1.302   1.610  1.00  0.00           C  
HETATM   10  C9  UNL     1      -1.109   1.200   0.222  1.00  0.00           C  
HETATM   11  C10 UNL     1       0.048   1.398  -0.343  1.00  0.00           C  
HETATM   12  C11 UNL     1       1.268   1.757   0.361  1.00  0.00           C  
HETATM   13  C12 UNL     1       2.377   0.727   0.176  1.00  0.00           C  
HETATM   14  C13 UNL     1       2.744   0.563  -1.266  1.00  0.00           C  
HETATM   15  C14 UNL     1       3.834  -0.452  -1.492  1.00  0.00           C  
HETATM   16  C15 UNL     1       5.079  -0.033  -0.759  1.00  0.00           C  
HETATM   17  C16 UNL     1       6.208  -1.038  -0.971  1.00  0.00           C  
HETATM   18  C17 UNL     1       7.419  -0.546  -0.204  1.00  0.00           C  
HETATM   19  C18 UNL     1       8.556  -1.487  -0.373  1.00  0.00           C  
HETATM   20  O2  UNL     1       8.445  -2.522  -1.070  1.00  0.00           O  
HETATM   21  O3  UNL     1       9.760  -1.232   0.242  1.00  0.00           O  
HETATM   22  H1  UNL     1      -9.136  -1.787   0.524  1.00  0.00           H  
HETATM   23  H2  UNL     1      -7.588  -2.494   0.002  1.00  0.00           H  
HETATM   24  H3  UNL     1      -7.705  -1.408   1.497  1.00  0.00           H  
HETATM   25  H4  UNL     1      -8.398  -0.648  -1.397  1.00  0.00           H  
HETATM   26  H5  UNL     1      -8.347   0.475   0.036  1.00  0.00           H  
HETATM   27  H6  UNL     1      -5.945  -0.985  -1.202  1.00  0.00           H  
HETATM   28  H7  UNL     1      -6.353   0.772  -1.360  1.00  0.00           H  
HETATM   29  H8  UNL     1      -6.227   1.111   1.028  1.00  0.00           H  
HETATM   30  H9  UNL     1      -5.811  -0.676   1.293  1.00  0.00           H  
HETATM   31  H10 UNL     1      -3.790  -0.351  -0.060  1.00  0.00           H  
HETATM   32  H11 UNL     1      -4.171   1.392  -0.211  1.00  0.00           H  
HETATM   33  H12 UNL     1      -2.359   1.276   3.369  1.00  0.00           H  
HETATM   34  H13 UNL     1      -0.472   1.571   2.237  1.00  0.00           H  
HETATM   35  H14 UNL     1      -1.976   0.929  -0.417  1.00  0.00           H  
HETATM   36  H15 UNL     1       0.078   1.278  -1.450  1.00  0.00           H  
HETATM   37  H16 UNL     1       1.634   2.726  -0.110  1.00  0.00           H  
HETATM   38  H17 UNL     1       1.142   1.949   1.424  1.00  0.00           H  
HETATM   39  H18 UNL     1       3.225   1.108   0.781  1.00  0.00           H  
HETATM   40  H19 UNL     1       2.037  -0.210   0.614  1.00  0.00           H  
HETATM   41  H20 UNL     1       1.870   0.364  -1.895  1.00  0.00           H  
HETATM   42  H21 UNL     1       3.158   1.547  -1.628  1.00  0.00           H  
HETATM   43  H22 UNL     1       4.000  -0.502  -2.592  1.00  0.00           H  
HETATM   44  H23 UNL     1       3.520  -1.477  -1.198  1.00  0.00           H  
HETATM   45  H24 UNL     1       5.379   0.966  -1.130  1.00  0.00           H  
HETATM   46  H25 UNL     1       4.886   0.056   0.329  1.00  0.00           H  
HETATM   47  H26 UNL     1       6.477  -1.055  -2.047  1.00  0.00           H  
HETATM   48  H27 UNL     1       5.899  -2.051  -0.681  1.00  0.00           H  
HETATM   49  H28 UNL     1       7.173  -0.369   0.866  1.00  0.00           H  
HETATM   50  H29 UNL     1       7.703   0.438  -0.647  1.00  0.00           H  
HETATM   51  H30 UNL     1       9.991  -0.361   0.702  1.00  0.00           H  
CONECT    1    2   22   23   24
CONECT    2    3   25   26
CONECT    3    4   27   28
CONECT    4    5   29   30
CONECT    5    6   31   32
CONECT    6    7    7    8
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

HMDB0246143
     RDKit          3D
13-Oxo-9,11-octadecadienoic acid
 51 50  0  0  0  0  0  0  0  0999 V2000
   -8.0273   -1.5973    0.4739 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8638   -0.4045   -0.4476 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4021   -0.1040   -0.7077 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7710    0.1914    0.6283 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2680    0.5110    0.4540 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7413    0.7842    1.8021 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6464    0.6867    2.7425 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4470    1.1276    2.2445 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3565    1.3019    1.6097 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1090    1.1995    0.2223 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0483    1.3982   -0.3428 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2684    1.7569    0.3605 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3768    0.7267    0.1763 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7444    0.5634   -1.2657 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8335   -0.4522   -1.4922 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0789   -0.0330   -0.7586 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2085   -1.0381   -0.9708 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4193   -0.5463   -0.2040 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5561   -1.4869   -0.3726 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4451   -2.5219   -1.0701 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.7603   -1.2319    0.2417 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1364   -1.7867    0.5240 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5881   -2.4938    0.0015 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7046   -1.4078    1.4972 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3981   -0.6480   -1.3972 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3472    0.4748    0.0364 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9450   -0.9854   -1.2022 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3526    0.7716   -1.3604 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2268    1.1107    1.0282 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8106   -0.6760    1.2929 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7901   -0.3512   -0.0603 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1711    1.3915   -0.2111 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3593    1.2759    3.3686 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4724    1.5708    2.2372 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9762    0.9290   -0.4173 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0783    1.2780   -1.4496 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6344    2.7265   -0.1098 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1424    1.9485    1.4244 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2247    1.1077    0.7810 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0369   -0.2102    0.6138 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8699    0.3643   -1.8953 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1576    1.5474   -1.6283 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9997   -0.5021   -2.5921 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5197   -1.4769   -1.1976 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3787    0.9660   -1.1300 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8857    0.0560    0.3285 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4774   -1.0554   -2.0466 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8992   -2.0506   -0.6811 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1731   -0.3689    0.8663 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7025    0.4381   -0.6471 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.9912   -0.3605    0.7021 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  2  0
  6  8  1  0
  8  9  2  3
  9 10  1  0
 10 11  2  3
 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
  3 28  1  0
  4 29  1  0
  4 30  1  0
  5 31  1  0
  5 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-Keto-9,11-octadecadienoic acid	ChEBI
13-Keto-9,11-ode	ChEBI
13-KetoODE	ChEBI
13-KODE	ChEBI
13-oxo-ODE	ChEBI
13-OxoODE	ChEBI
13-Keto-9,11-octadecadienoate	Generator
13-oxo-9,11-Octadecadienoate	Generator
13-Keto-9,11,-octadecadienoic acid	HMDB
13-KODDA	HMDB
13-Oxooctadecadienoic acid	HMDB
13-oxo-9,11-Octadecadienoic acid	MeSH

Chemical Formula

C₁₈H₃₀O₃

Average Molecular Weight

294.429

Monoisotopic Molecular Weight

294.219494826

IUPAC Name

13-oxooctadeca-9,11-dienoic acid

Traditional Name

13-oxooctadeca-9,11-dienoic acid

CAS Registry Number

Not Available

SMILES

CCCCCC(=O)C=CC=CCCCCCCCC(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/h7,9,12,15H,2-6,8,10-11,13-14,16H2,1H3,(H,20,21)

InChI Key

JHXAZBBVQSRKJR-UHFFFAOYSA-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
Unsaturated fatty acid
Fatty acid
Acryloyl-group
Enone
Alpha,beta-unsaturated ketone
Ketone
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxide
Organic oxygen compound
Organooxygen compound
Hydrocarbon derivative
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: 31557052)

Source

Exogenous

Exogenous (PMID: 31557052)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

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
logP	5.66	ALOGPS
logP	5.6	ChemAxon
logS	-5.4	ALOGPS
pKa (Strongest Acidic)	4.99	ChemAxon
pKa (Strongest Basic)	-4.6	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	54.37 Å²	ChemAxon
Rotatable Bond Count	14	ChemAxon
Refractivity	89.14 m³·mol⁻¹	ChemAxon
Polarizability	37.32 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	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]+	178.867	30932474
DeepCCS	[M-H]-	174.904	30932474
DeepCCS	[M-2H]-	211.392	30932474
DeepCCS	[M+Na]+	187.682	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]-	179.5	32859911
AllCCS	[M+Na-2H]-	181.0	32859911
AllCCS	[M+HCOO]-	182.7	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
13-Oxo-9,11-octadecadienoic acid	CCCCCC(=O)C=CC=CCCCCCCCC(O)=O	3778.8	Standard polar	33892256
13-Oxo-9,11-octadecadienoic acid	CCCCCC(=O)C=CC=CCCCCCCCC(O)=O	2279.8	Standard non polar	33892256
13-Oxo-9,11-octadecadienoic acid	CCCCCC(=O)C=CC=CCCCCCCCC(O)=O	2464.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
13-Oxo-9,11-octadecadienoic acid,2TMS,isomer #1	CCCCC=C(C=CC=CCCCCCCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C	2643.6	Semi standard non polar	33892256
13-Oxo-9,11-octadecadienoic acid,2TMS,isomer #1	CCCCC=C(C=CC=CCCCCCCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C	2546.5	Standard non polar	33892256
13-Oxo-9,11-octadecadienoic acid,2TMS,isomer #1	CCCCC=C(C=CC=CCCCCCCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C	2652.6	Standard polar	33892256
13-Oxo-9,11-octadecadienoic acid,2TBDMS,isomer #1	CCCCC=C(C=CC=CCCCCCCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3135.4	Semi standard non polar	33892256
13-Oxo-9,11-octadecadienoic acid,2TBDMS,isomer #1	CCCCC=C(C=CC=CCCCCCCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	2933.4	Standard non polar	33892256
13-Oxo-9,11-octadecadienoic acid,2TBDMS,isomer #1	CCCCC=C(C=CC=CCCCCCCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	2806.0	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 13-Oxo-9,11-octadecadienoic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-004j-6930000000-d10bec81e9ec9e716fa2	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 13-Oxo-9,11-octadecadienoic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 13-Oxo-9,11-octadecadienoic acid GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 13-Oxo-9,11-octadecadienoic acid GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 13-Oxo-9,11-octadecadienoic acid GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 13-Oxo-9,11-octadecadienoic acid GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-03	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-Oxo-9,11-octadecadienoic acid 10V, Positive-QTOF	splash10-004j-1490000000-80caae23bc80ab7cea2c	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 13-Oxo-9,11-octadecadienoic acid 20V, Positive-QTOF	splash10-0aba-8940000000-d8f1355540068e477746	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 13-Oxo-9,11-octadecadienoic acid 40V, Positive-QTOF	splash10-0apm-9200000000-cad11773185d75e4951e	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 13-Oxo-9,11-octadecadienoic acid 10V, Negative-QTOF	splash10-0006-0090000000-70cae714b15b662c6aa1	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 13-Oxo-9,11-octadecadienoic acid 20V, Negative-QTOF	splash10-002f-2590000000-dba8b2a106352cfef082	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 13-Oxo-9,11-octadecadienoic acid 40V, Negative-QTOF	splash10-052f-9530000000-71771e55577a451c8cb4	2021-10-12	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

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 but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	31557052	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

FDB023396

KNApSAcK ID

Not Available

Chemspider ID

21237636

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

160205

PDB ID

Not Available

ChEBI ID

136531

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

Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]

Showing metabocard for 13-Oxo-9,11-octadecadienoic acid (HMDB0246143)

MOL for HMDB0246143 (13-Oxo-9,11-octadecadienoic acid)

3D MOL for HMDB0246143 (13-Oxo-9,11-octadecadienoic acid)

3D SDF for HMDB0246143 (13-Oxo-9,11-octadecadienoic acid)

3D-SDF for HMDB0246143 (13-Oxo-9,11-octadecadienoic acid)

PDB for HMDB0246143 (13-Oxo-9,11-octadecadienoic acid)

3D PDB for HMDB0246143 (13-Oxo-9,11-octadecadienoic acid)

SMILES for HMDB0246143 (13-Oxo-9,11-octadecadienoic acid)

INCHI for HMDB0246143 (13-Oxo-9,11-octadecadienoic acid)

Structure for HMDB0246143 (13-Oxo-9,11-octadecadienoic acid)

3D Structure for HMDB0246143 (13-Oxo-9,11-octadecadienoic acid)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra