MiMeDB: Showing metabocard for 13-HOTE (MMDBc0000788)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2020-12-10 21:51:49 UTC

Update Date

2024-04-30 19:33:42 UTC

Metabolite ID

MMDBc0000788

Metabolite Identification

Common Name

13-HOTE

Description

(9Z,11E,13S,15Z)-13-Hydroxyoctadeca-9,11,15-trienoic acid 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 (9Z,11E,13S,15Z)-13-Hydroxyoctadeca-9,11,15-trienoic acid.

Structure

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

HMDB0244523
     RDKit          3D
(9Z,11E,13S,15Z)-13-Hydroxyoctadeca-9,11,15-trienoic acid
 51 50  0  0  0  0  0  0  0  0999 V2000
   -8.6479   -0.6497    0.7749 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1958   -1.0350    0.5073 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8403   -0.5166   -0.8054 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9094    0.3260   -1.0829 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0050    0.9411   -0.1047 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5445    0.6093   -0.4034 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3628   -0.7715   -0.3621 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7274    1.2819    0.6391 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4082    1.2642    0.5383 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7865    0.5908   -0.5840 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5057    0.5125   -0.7815 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4614    1.1162    0.1418 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4062    0.0741    0.7482 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2067   -0.6437   -0.2957 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0794    0.2311   -1.1284 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1011    0.9953   -0.3394 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0456    0.1290    0.4218 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8154   -0.7779   -0.5124 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7305   -1.6072    0.2966 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7896   -1.5062    1.5409 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5433   -2.5203   -0.3452 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7427   -0.4791    1.8606 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8458    0.2936    0.2540 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.3142   -1.4817    0.4623 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0993   -2.1641    0.5271 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5636   -0.6416    1.2962 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4506   -0.9009   -1.6538 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7370    0.6471   -2.1468 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2017    0.5935    0.9108 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1525    2.0608   -0.1733 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2793    0.9403   -1.4403 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0279   -1.2102   -0.9364 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1936    1.7877    1.4826 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8742    1.7705    1.3277 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4426    0.1038   -1.3348 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8701   -0.0180   -1.6607 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0395    1.6523    1.0053 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1527    1.8256   -0.3937 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7692   -0.6378    1.2817 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0531    0.6508    1.4538 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4548   -1.1054   -1.0027 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7432   -1.5305    0.1191 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4477    0.9487   -1.6843 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5745   -0.4067   -1.8888 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7179    1.5674   -1.0908 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6440    1.7665    0.3041 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5648   -0.5131    1.1722 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7623    0.7978    0.9513 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0563   -1.4687   -0.9777 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3562   -0.2041   -1.2971 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.4614   -2.6880    0.0464 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  3
  4  5  1  0
  5  6  1  0
  6  7  1  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
  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 02251203242D          

 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
   -2.0033    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
   -0.5743    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
    0.1401    2.5559    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
    1.5691    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
    2.9980    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
    4.4270    2.5559    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
    5.8559    2.5559    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
    7.2849    2.5559    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
    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
  1  2  1  0  0  0  0
  3  2  1  4  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  8  6  1  4  0  0  0
  8  9  2  0  0  0  0
 10  9  1  4  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  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
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  2  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0000788

> <DATABASE_NAME>
MIME

> <SMILES>
CCC=CCC(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/h3,7,9,11-12,15,17,19H,2,4-6,8,10,13-14,16H2,1H3,(H,20,21)

> <INCHI_KEY>
KLLGGGQNRTVBSU-UHFFFAOYSA-N

> <FORMULA>
C18H30O3

> <MOLECULAR_WEIGHT>
294.429

> <EXACT_MASS>
294.219494826

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
36.810277024422405

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
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-hydroxyoctadeca-9,11,15-trienoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0244523
     RDKit          3D
(9Z,11E,13S,15Z)-13-Hydroxyoctadeca-9,11,15-trienoic acid
 51 50  0  0  0  0  0  0  0  0999 V2000
   -8.6479   -0.6497    0.7749 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1958   -1.0350    0.5073 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8403   -0.5166   -0.8054 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9094    0.3260   -1.0829 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0050    0.9411   -0.1047 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5445    0.6093   -0.4034 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3628   -0.7715   -0.3621 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7274    1.2819    0.6391 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4082    1.2642    0.5383 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7865    0.5908   -0.5840 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5057    0.5125   -0.7815 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4614    1.1162    0.1418 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4062    0.0741    0.7482 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2067   -0.6437   -0.2957 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0794    0.2311   -1.1284 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1011    0.9953   -0.3394 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0456    0.1290    0.4218 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8154   -0.7779   -0.5124 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7305   -1.6072    0.2966 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7896   -1.5062    1.5409 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5433   -2.5203   -0.3452 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7427   -0.4791    1.8606 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8458    0.2936    0.2540 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.3142   -1.4817    0.4623 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0993   -2.1641    0.5271 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5636   -0.6416    1.2962 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4506   -0.9009   -1.6538 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7370    0.6471   -2.1468 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2017    0.5935    0.9108 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1525    2.0608   -0.1733 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2793    0.9403   -1.4403 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0279   -1.2102   -0.9364 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1936    1.7877    1.4826 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8742    1.7705    1.3277 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4426    0.1038   -1.3348 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8701   -0.0180   -1.6607 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0395    1.6523    1.0053 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1527    1.8256   -0.3937 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7692   -0.6378    1.2817 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0531    0.6508    1.4538 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4548   -1.1054   -1.0027 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7432   -1.5305    0.1191 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4477    0.9487   -1.6843 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5745   -0.4067   -1.8888 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7179    1.5674   -1.0908 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6440    1.7665    0.3041 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5648   -0.5131    1.1722 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7623    0.7978    0.9513 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0563   -1.4687   -0.9777 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3562   -0.2041   -1.2971 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.4614   -2.6880    0.0464 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  3
  4  5  1  0
  5  6  1  0
  6  7  1  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
  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                                 25-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   25-FEB-12         0                                  
HETATM    1  C   UNK     0      -7.741   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      -3.739   4.001   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.406   4.771   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.072   4.001   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -1.072   2.461   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       0.262   4.771   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.595   4.001   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.929   4.771   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.263   4.001   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.596   4.771   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.930   4.001   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.264   4.771   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       9.597   4.001   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      10.931   4.771   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      12.265   4.001   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      13.598   4.771   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      14.932   4.001   0.000  0.00  0.00           C+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    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   40    0
END

COMPND    HMDB0244523
HETATM    1  C1  UNL     1      -8.648  -0.650   0.775  1.00  0.00           C  
HETATM    2  C2  UNL     1      -7.196  -1.035   0.507  1.00  0.00           C  
HETATM    3  C3  UNL     1      -6.840  -0.517  -0.805  1.00  0.00           C  
HETATM    4  C4  UNL     1      -5.909   0.326  -1.083  1.00  0.00           C  
HETATM    5  C5  UNL     1      -5.005   0.941  -0.105  1.00  0.00           C  
HETATM    6  C6  UNL     1      -3.544   0.609  -0.403  1.00  0.00           C  
HETATM    7  O1  UNL     1      -3.363  -0.771  -0.362  1.00  0.00           O  
HETATM    8  C7  UNL     1      -2.727   1.282   0.639  1.00  0.00           C  
HETATM    9  C8  UNL     1      -1.408   1.264   0.538  1.00  0.00           C  
HETATM   10  C9  UNL     1      -0.787   0.591  -0.584  1.00  0.00           C  
HETATM   11  C10 UNL     1       0.506   0.512  -0.781  1.00  0.00           C  
HETATM   12  C11 UNL     1       1.461   1.116   0.142  1.00  0.00           C  
HETATM   13  C12 UNL     1       2.406   0.074   0.748  1.00  0.00           C  
HETATM   14  C13 UNL     1       3.207  -0.644  -0.296  1.00  0.00           C  
HETATM   15  C14 UNL     1       4.079   0.231  -1.128  1.00  0.00           C  
HETATM   16  C15 UNL     1       5.101   0.995  -0.339  1.00  0.00           C  
HETATM   17  C16 UNL     1       6.046   0.129   0.422  1.00  0.00           C  
HETATM   18  C17 UNL     1       6.815  -0.778  -0.512  1.00  0.00           C  
HETATM   19  C18 UNL     1       7.730  -1.607   0.297  1.00  0.00           C  
HETATM   20  O2  UNL     1       7.790  -1.506   1.541  1.00  0.00           O  
HETATM   21  O3  UNL     1       8.543  -2.520  -0.345  1.00  0.00           O  
HETATM   22  H1  UNL     1      -8.743  -0.479   1.861  1.00  0.00           H  
HETATM   23  H2  UNL     1      -8.846   0.294   0.254  1.00  0.00           H  
HETATM   24  H3  UNL     1      -9.314  -1.482   0.462  1.00  0.00           H  
HETATM   25  H4  UNL     1      -7.099  -2.164   0.527  1.00  0.00           H  
HETATM   26  H5  UNL     1      -6.564  -0.642   1.296  1.00  0.00           H  
HETATM   27  H6  UNL     1      -7.451  -0.901  -1.654  1.00  0.00           H  
HETATM   28  H7  UNL     1      -5.737   0.647  -2.147  1.00  0.00           H  
HETATM   29  H8  UNL     1      -5.202   0.594   0.911  1.00  0.00           H  
HETATM   30  H9  UNL     1      -5.152   2.061  -0.173  1.00  0.00           H  
HETATM   31  H10 UNL     1      -3.279   0.940  -1.440  1.00  0.00           H  
HETATM   32  H11 UNL     1      -4.028  -1.210  -0.936  1.00  0.00           H  
HETATM   33  H12 UNL     1      -3.194   1.788   1.483  1.00  0.00           H  
HETATM   34  H13 UNL     1      -0.874   1.771   1.328  1.00  0.00           H  
HETATM   35  H14 UNL     1      -1.443   0.104  -1.335  1.00  0.00           H  
HETATM   36  H15 UNL     1       0.870  -0.018  -1.661  1.00  0.00           H  
HETATM   37  H16 UNL     1       1.040   1.652   1.005  1.00  0.00           H  
HETATM   38  H17 UNL     1       2.153   1.826  -0.394  1.00  0.00           H  
HETATM   39  H18 UNL     1       1.769  -0.638   1.282  1.00  0.00           H  
HETATM   40  H19 UNL     1       3.053   0.651   1.454  1.00  0.00           H  
HETATM   41  H20 UNL     1       2.455  -1.105  -1.003  1.00  0.00           H  
HETATM   42  H21 UNL     1       3.743  -1.531   0.119  1.00  0.00           H  
HETATM   43  H22 UNL     1       3.448   0.949  -1.684  1.00  0.00           H  
HETATM   44  H23 UNL     1       4.574  -0.407  -1.889  1.00  0.00           H  
HETATM   45  H24 UNL     1       5.718   1.567  -1.091  1.00  0.00           H  
HETATM   46  H25 UNL     1       4.644   1.767   0.304  1.00  0.00           H  
HETATM   47  H26 UNL     1       5.565  -0.513   1.172  1.00  0.00           H  
HETATM   48  H27 UNL     1       6.762   0.798   0.951  1.00  0.00           H  
HETATM   49  H28 UNL     1       6.056  -1.469  -0.978  1.00  0.00           H  
HETATM   50  H29 UNL     1       7.356  -0.204  -1.297  1.00  0.00           H  
HETATM   51  H30 UNL     1       9.461  -2.688   0.046  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

HMDB0244523
     RDKit          3D
(9Z,11E,13S,15Z)-13-Hydroxyoctadeca-9,11,15-trienoic acid
 51 50  0  0  0  0  0  0  0  0999 V2000
   -8.6479   -0.6497    0.7749 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1958   -1.0350    0.5073 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8403   -0.5166   -0.8054 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9094    0.3260   -1.0829 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0050    0.9411   -0.1047 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5445    0.6093   -0.4034 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3628   -0.7715   -0.3621 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7274    1.2819    0.6391 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4082    1.2642    0.5383 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7865    0.5908   -0.5840 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5057    0.5125   -0.7815 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4614    1.1162    0.1418 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4062    0.0741    0.7482 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2067   -0.6437   -0.2957 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0794    0.2311   -1.1284 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1011    0.9953   -0.3394 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0456    0.1290    0.4218 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8154   -0.7779   -0.5124 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7305   -1.6072    0.2966 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7896   -1.5062    1.5409 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5433   -2.5203   -0.3452 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7427   -0.4791    1.8606 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8458    0.2936    0.2540 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.3142   -1.4817    0.4623 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0993   -2.1641    0.5271 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5636   -0.6416    1.2962 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4506   -0.9009   -1.6538 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7370    0.6471   -2.1468 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2017    0.5935    0.9108 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1525    2.0608   -0.1733 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2793    0.9403   -1.4403 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0279   -1.2102   -0.9364 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1936    1.7877    1.4826 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8742    1.7705    1.3277 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4426    0.1038   -1.3348 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8701   -0.0180   -1.6607 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0395    1.6523    1.0053 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1527    1.8256   -0.3937 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7692   -0.6378    1.2817 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0531    0.6508    1.4538 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4548   -1.1054   -1.0027 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7432   -1.5305    0.1191 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4477    0.9487   -1.6843 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5745   -0.4067   -1.8888 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7179    1.5674   -1.0908 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6440    1.7665    0.3041 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5648   -0.5131    1.1722 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7623    0.7978    0.9513 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0563   -1.4687   -0.9777 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3562   -0.2041   -1.2971 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.4614   -2.6880    0.0464 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  3
  4  5  1  0
  5  6  1  0
  6  7  1  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
  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

Synonyms

Value	Source
(9Z,11E,13S,15Z)-13-Hydroxyoctadeca-9,11,15-trienoate	Generator

Molecular Formula

C₁₈H₃₀O₃

Average Mass

294.429

Monoisotopic Mass

294.219494826

IUPAC Name

13-hydroxyoctadeca-9,11,15-trienoic acid

Traditional Name

13-hydroxyoctadeca-9,11,15-trienoic acid

CAS Registry Number

Not Available

SMILES

CCC=CCC(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/h3,7,9,11-12,15,17,19H,2,4-6,8,10,13-14,16H2,1H3,(H,20,21)

InChI Key

KLLGGGQNRTVBSU-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
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

Not Available

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted 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	36.81 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

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-00mo-9660000000-cdd31a587f020c6bb71f	2021-09-23	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-03	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-03	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_1) - 70eV, Positive	Not Available	2021-11-03	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-03	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-03	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	2021-11-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-004i-0590000000-bd893bd94b5a258e0c27	2021-10-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0561-3920000000-0a0eff6d89655b3e7e3a	2021-10-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-067i-9700000000-dd60260108f968b4a153	2021-10-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-002f-0090000000-e447b375f3a269ef2976	2021-10-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004l-1390000000-d48b71d8fb0d418ae2de	2021-10-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9310000000-070b30fb068bd05ccdb9	2021-10-12	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-20	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood
Feces

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Not Available

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria	Proteobacteria	1		Indirect association between microbiota composition and metabolites measured in host biospecimen

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	29808030
Human Blood	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	31557052

External Links

HMDB ID

HMDB0244523

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB027358

KNApSAcK ID

Not Available

Chemspider ID

21237593

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

53394276

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

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-HOTE (MMDBc0000788)

MOL for #<Metabolite:0x00007fd12004fda0>

3D MOL for #<Metabolite:0x00007fd12004fda0>

3D SDF for #<Metabolite:0x00007fd12004fda0>

3D-SDF for #<Metabolite:0x00007fd12004fda0>

PDB for #<Metabolite:0x00007fd12004fda0>

3D PDB for #<Metabolite:0x00007fd12004fda0>

SMILES for #<Metabolite:0x00007fd12004fda0>

INCHI for #<Metabolite:0x00007fd12004fda0>

Structure for #<Metabolite:0x00007fd12004fda0>

3D Structure for #<Metabolite:0x00007fd12004fda0>