MiMeDB: Showing metabocard for 11-Hydroperoxyoctadeca-9,12-Dienoic Acid (MMDBc0049810)

Record Information

Version

2.0

Status

Detected and Quantified

Creation Date

2022-04-29 22:43:04 UTC

Update Date

2025-10-07 16:08:13 UTC

Metabolite ID

MMDBc0049810

Metabolite Identification

Common Name

11-Hydroperoxyoctadeca-9,12-Dienoic Acid

Description

11-Hydroperoxyoctadeca-9,12-Dienoic Acid is a hydroperoxy fatty acid. There is limited literature available on this metabolite, and its biological significance and functions remain largely unexplored in scientific studies.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652304302200432D          

 53 52  0  0  1  0            999 V2000
    3.7125    3.7934    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9980    3.3809    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2836    3.7934    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5691    3.3809    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5691    4.2059    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8546    3.7934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4421    4.5079    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1401    3.3809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5743    3.7934    0.0000 H   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
    0.5935    1.8666    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9637    2.5079    0.0000 H   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
   -1.0277    2.8327    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3979    2.1914    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5743    1.3184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1210    0.6291    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2493    1.2704    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2888    0.9059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7421    1.5952    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1124    0.9539    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2888    0.0809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1138    0.0809    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2888   -0.7441    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4638    0.0809    0.0000 H   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
    1.3872    1.7512    0.0000 H   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
    2.2836    1.3184    0.0000 H   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
    2.2836    2.9684    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7125    2.9684    0.0000 H   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
    3.3422    1.4062    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0828    1.4062    0.0000 H   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
    5.0590    3.0862    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5702    3.3684    0.0000 H   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
    4.7712    1.4062    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5117    1.4062    0.0000 H   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
    6.5790    2.9532    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8908    3.3802    0.0000 H   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
    6.2001    1.4062    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9406    1.4062    0.0000 H   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
    7.9146    3.0889    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4227    3.3693    0.0000 H   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  5  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
  2  3  1  0  0  0  0
  4  3  1  6  0  0  0
  4  5  1  1  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  2  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
 10 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
 13 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
 16 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  1  0  0  0  0
 19 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  1  0  0  0  0
 22 25  1  0  0  0  0
  4 26  1  0  0  0  0
 26 27  1  0  0  0  0
 26 28  2  0  0  0  0
 28 29  1  0  0  0  0
 28 30  1  0  0  0  0
 30 31  1  0  0  0  0
 30 32  1  0  0  0  0
 30 33  1  0  0  0  0
 33 34  1  0  0  0  0
 33 35  1  0  0  0  0
 33 36  1  0  0  0  0
 36 37  1  0  0  0  0
 36 38  1  0  0  0  0
 36 39  1  0  0  0  0
 39 40  1  0  0  0  0
 39 41  1  0  0  0  0
 39 42  1  0  0  0  0
 42 43  1  0  0  0  0
 42 44  1  0  0  0  0
 42 45  1  0  0  0  0
 45 46  1  0  0  0  0
 45 47  1  0  0  0  0
 45 48  1  0  0  0  0
 48 49  1  0  0  0  0
 48 50  1  0  0  0  0
 48 51  1  0  0  0  0
 51 52  1  0  0  0  0
 51 53  2  0  0  0  0
M  CHG  1  52  -1
M  END


  Mrv1652304302200432D          

 53 52  0  0  1  0            999 V2000
    3.7125    3.7934    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9980    3.3809    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2836    3.7934    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5691    3.3809    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5691    4.2059    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8546    3.7934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4421    4.5079    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1401    3.3809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5743    3.7934    0.0000 H   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
    0.5935    1.8666    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9637    2.5079    0.0000 H   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
   -1.0277    2.8327    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3979    2.1914    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5743    1.3184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1210    0.6291    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2493    1.2704    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2888    0.9059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7421    1.5952    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1124    0.9539    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2888    0.0809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1138    0.0809    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2888   -0.7441    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4638    0.0809    0.0000 H   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
    1.3872    1.7512    0.0000 H   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
    2.2836    1.3184    0.0000 H   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
    2.2836    2.9684    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7125    2.9684    0.0000 H   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
    3.3422    1.4062    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0828    1.4062    0.0000 H   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
    5.0590    3.0862    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5702    3.3684    0.0000 H   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
    4.7712    1.4062    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5117    1.4062    0.0000 H   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
    6.5790    2.9532    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8908    3.3802    0.0000 H   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
    6.2001    1.4062    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9406    1.4062    0.0000 H   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
    7.9146    3.0889    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4227    3.3693    0.0000 H   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  5  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
  2  3  1  0  0  0  0
  4  3  1  6  0  0  0
  4  5  1  1  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  2  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
 10 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
 13 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
 16 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  1  0  0  0  0
 19 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  1  0  0  0  0
 22 25  1  0  0  0  0
  4 26  1  0  0  0  0
 26 27  1  0  0  0  0
 26 28  2  0  0  0  0
 28 29  1  0  0  0  0
 28 30  1  0  0  0  0
 30 31  1  0  0  0  0
 30 32  1  0  0  0  0
 30 33  1  0  0  0  0
 33 34  1  0  0  0  0
 33 35  1  0  0  0  0
 33 36  1  0  0  0  0
 36 37  1  0  0  0  0
 36 38  1  0  0  0  0
 36 39  1  0  0  0  0
 39 40  1  0  0  0  0
 39 41  1  0  0  0  0
 39 42  1  0  0  0  0
 42 43  1  0  0  0  0
 42 44  1  0  0  0  0
 42 45  1  0  0  0  0
 45 46  1  0  0  0  0
 45 47  1  0  0  0  0
 45 48  1  0  0  0  0
 48 49  1  0  0  0  0
 48 50  1  0  0  0  0
 48 51  1  0  0  0  0
 51 52  1  0  0  0  0
 51 53  2  0  0  0  0
M  CHG  1  52  -1
M  END
> <DATABASE_ID>
MMDBc0049810

> <DATABASE_NAME>
MIME

> <SMILES>
[H]OO[C@@]([H])(C(\[H])=C(\[H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H])C(\[H])=C(\[H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([O-])=O

> <INCHI_IDENTIFIER>
InChI=1S/C18H32O4/c1-2-3-4-8-11-14-17(22-21)15-12-9-6-5-7-10-13-16-18(19)20/h11-12,14-15,17,21H,2-10,13,16H2,1H3,(H,19,20)/p-1/b14-11-,15-12-/t17-/m0/s1

> <INCHI_KEY>
PLWDMWAXENHPLY-PDBSFCERSA-M

> <FORMULA>
C18H31O4

> <MOLECULAR_WEIGHT>
311.443

> <EXACT_MASS>
311.222783058

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
53

> <JCHEM_AVERAGE_POLARIZABILITY>
37.84317830530324

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
-1

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(9Z,11S,12Z)-11-hydroperoxyoctadeca-9,12-dienoate

> <ALOGPS_LOGP>
5.80

> <JCHEM_LOGP>
5.796308564666666

> <ALOGPS_LOGS>
-5.31

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
11.694100265954567

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.988167198460601

> <JCHEM_PKA_STRONGEST_BASIC>
-4.244800581059308

> <JCHEM_POLAR_SURFACE_AREA>
69.59

> <JCHEM_REFRACTIVITY>
102.0676

> <JCHEM_ROTATABLE_BOND_COUNT>
15

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.62e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(11S)-11-hydroperoxylinoleate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 30-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   30-APR-22         0                                  
HETATM    1  H   UNK     0       6.930   7.081   0.000  0.00  0.00           H+0
HETATM    2  O   UNK     0       5.596   6.311   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0       4.263   7.081   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       2.929   6.311   0.000  0.00  0.00           C+0
HETATM    5  H   UNK     0       2.929   7.851   0.000  0.00  0.00           H+0
HETATM    6  C   UNK     0       1.595   7.081   0.000  0.00  0.00           C+0
HETATM    7  H   UNK     0       0.825   8.415   0.000  0.00  0.00           H+0
HETATM    8  C   UNK     0       0.262   6.311   0.000  0.00  0.00           C+0
HETATM    9  H   UNK     0      -1.072   7.081   0.000  0.00  0.00           H+0
HETATM   10  C   UNK     0       0.262   4.771   0.000  0.00  0.00           C+0
HETATM   11  H   UNK     0       1.108   3.484   0.000  0.00  0.00           H+0
HETATM   12  H   UNK     0       1.799   4.681   0.000  0.00  0.00           H+0
HETATM   13  C   UNK     0      -1.072   4.001   0.000  0.00  0.00           C+0
HETATM   14  H   UNK     0      -1.918   5.288   0.000  0.00  0.00           H+0
HETATM   15  H   UNK     0      -2.609   4.091   0.000  0.00  0.00           H+0
HETATM   16  C   UNK     0      -1.072   2.461   0.000  0.00  0.00           C+0
HETATM   17  H   UNK     0      -0.226   1.174   0.000  0.00  0.00           H+0
HETATM   18  H   UNK     0       0.465   2.371   0.000  0.00  0.00           H+0
HETATM   19  C   UNK     0      -2.406   1.691   0.000  0.00  0.00           C+0
HETATM   20  H   UNK     0      -3.252   2.978   0.000  0.00  0.00           H+0
HETATM   21  H   UNK     0      -3.943   1.781   0.000  0.00  0.00           H+0
HETATM   22  C   UNK     0      -2.406   0.151   0.000  0.00  0.00           C+0
HETATM   23  H   UNK     0      -3.946   0.151   0.000  0.00  0.00           H+0
HETATM   24  H   UNK     0      -2.406  -1.389   0.000  0.00  0.00           H+0
HETATM   25  H   UNK     0      -0.866   0.151   0.000  0.00  0.00           H+0
HETATM   26  C   UNK     0       2.929   4.771   0.000  0.00  0.00           C+0
HETATM   27  H   UNK     0       2.589   3.269   0.000  0.00  0.00           H+0
HETATM   28  C   UNK     0       4.263   4.001   0.000  0.00  0.00           C+0
HETATM   29  H   UNK     0       4.263   2.461   0.000  0.00  0.00           H+0
HETATM   30  C   UNK     0       5.596   4.771   0.000  0.00  0.00           C+0
HETATM   31  H   UNK     0       4.263   5.541   0.000  0.00  0.00           H+0
HETATM   32  H   UNK     0       6.930   5.541   0.000  0.00  0.00           H+0
HETATM   33  C   UNK     0       6.930   4.001   0.000  0.00  0.00           C+0
HETATM   34  H   UNK     0       6.239   2.625   0.000  0.00  0.00           H+0
HETATM   35  H   UNK     0       7.621   2.625   0.000  0.00  0.00           H+0
HETATM   36  C   UNK     0       8.264   4.771   0.000  0.00  0.00           C+0
HETATM   37  H   UNK     0       9.443   5.761   0.000  0.00  0.00           H+0
HETATM   38  H   UNK     0       8.531   6.288   0.000  0.00  0.00           H+0
HETATM   39  C   UNK     0       9.597   4.001   0.000  0.00  0.00           C+0
HETATM   40  H   UNK     0       8.906   2.625   0.000  0.00  0.00           H+0
HETATM   41  H   UNK     0      10.289   2.625   0.000  0.00  0.00           H+0
HETATM   42  C   UNK     0      10.931   4.771   0.000  0.00  0.00           C+0
HETATM   43  H   UNK     0      12.281   5.513   0.000  0.00  0.00           H+0
HETATM   44  H   UNK     0      10.996   6.310   0.000  0.00  0.00           H+0
HETATM   45  C   UNK     0      12.265   4.001   0.000  0.00  0.00           C+0
HETATM   46  H   UNK     0      11.574   2.625   0.000  0.00  0.00           H+0
HETATM   47  H   UNK     0      12.956   2.625   0.000  0.00  0.00           H+0
HETATM   48  C   UNK     0      13.598   4.771   0.000  0.00  0.00           C+0
HETATM   49  H   UNK     0      14.774   5.766   0.000  0.00  0.00           H+0
HETATM   50  H   UNK     0      13.856   6.289   0.000  0.00  0.00           H+0
HETATM   51  C   UNK     0      14.932   4.001   0.000  0.00  0.00           C+0
HETATM   52  O   UNK     0      16.266   4.771   0.000  0.00  0.00           O-1
HETATM   53  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    6   26                                             
CONECT    5    4                                                            
CONECT    6    4    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   12   13                                             
CONECT   11   10                                                            
CONECT   12   10                                                            
CONECT   13   10   14   15   16                                             
CONECT   14   13                                                            
CONECT   15   13                                                            
CONECT   16   13   17   18   19                                             
CONECT   17   16                                                            
CONECT   18   16                                                            
CONECT   19   16   20   21   22                                             
CONECT   20   19                                                            
CONECT   21   19                                                            
CONECT   22   19   23   24   25                                             
CONECT   23   22                                                            
CONECT   24   22                                                            
CONECT   25   22                                                            
CONECT   26    4   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   31   32   33                                             
CONECT   31   30                                                            
CONECT   32   30                                                            
CONECT   33   30   34   35   36                                             
CONECT   34   33                                                            
CONECT   35   33                                                            
CONECT   36   33   37   38   39                                             
CONECT   37   36                                                            
CONECT   38   36                                                            
CONECT   39   36   40   41   42                                             
CONECT   40   39                                                            
CONECT   41   39                                                            
CONECT   42   39   43   44   45                                             
CONECT   43   42                                                            
CONECT   44   42                                                            
CONECT   45   42   46   47   48                                             
CONECT   46   45                                                            
CONECT   47   45                                                            
CONECT   48   45   49   50   51                                             
CONECT   49   48                                                            
CONECT   50   48                                                            
CONECT   51   48   52   53                                                  
CONECT   52   51                                                            
CONECT   53   51                                                            
MASTER        0    0    0    0    0    0    0    0   53    0  104    0
END

Synonyms

Value	Source
(11S)-11-Hydroperoxylinoleate anion	ChEBI
(11S)-Hydroperoxy-(9Z,12Z)-octadecadienoate	ChEBI
(11S)-11-Hydroperoxylinoleic acid anion	Generator
(11S)-Hydroperoxy-(9Z,12Z)-octadecadienoic acid	Generator
(11S)-11-Hydroperoxylinoleic acid	Generator

Molecular Formula

C₁₈H₃₁O₄

Average Mass

311.443

Monoisotopic Mass

311.222783058

IUPAC Name

(9Z,11S,12Z)-11-hydroperoxyoctadeca-9,12-dienoate

Traditional Name

(11S)-11-hydroperoxylinoleate

CAS Registry Number

Not Available

SMILES

[H]OO[C@@]([H])(C(\[H])=C(\[H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H])C(\[H])=C(\[H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([O-])=O

InChI Identifier

InChI=1S/C18H32O4/c1-2-3-4-8-11-14-17(22-21)15-12-9-6-5-7-10-13-16-18(19)20/h11-12,14-15,17,21H,2-10,13,16H2,1H3,(H,19,20)/p-1/b14-11-,15-12-/t17-/m0/s1

InChI Key

PLWDMWAXENHPLY-PDBSFCERSA-M

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
Hydroperoxy fatty acid
Unsaturated fatty acid
Fatty acid
Allylic hydroperoxide
Hydroperoxide
Peroxol
Monocarboxylic acid or derivatives
Alkyl hydroperoxide
Carboxylic acid
Carboxylic acid derivative
Carbonyl group
Organooxygen compound
Organic oxygen compound
Hydrocarbon derivative
Organic oxide
Organic anion
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

monocarboxylic acid anion (CHEBI:57467 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	0.0016 g/L	ALOGPS
logP	5.8	ALOGPS
logP	5.8	ChemAxon
logS	-5.3	ALOGPS
pKa (Strongest Acidic)	4.99	ChemAxon
pKa (Strongest Basic)	-4.2	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	69.59 Å²	ChemAxon
Rotatable Bond Count	15	ChemAxon
Refractivity	102.07 m³·mol⁻¹	ChemAxon
Polarizability	37.84 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

Spectra

Not Available

Chromatographic Retention Times and Retention Indices

Retention Times

Chromatography Type	Technique	Column	Deposition Date	Retention Time (s)
Liquid Chromatography	HILIC	Waters Acquity UPLC-BEH Amide column (eluted)	2025-10-24	242.6
Liquid Chromatography	HILIC	Accucore 150 Amide HILIC (eluted)	2025-10-24	34.5
Liquid Chromatography	Reversed-phase	Hypersil Gold 1.9 µm C18 (eluted)	2025-10-24	672.1
Liquid Chromatography	Reversed-phase	Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) (eluted)	2025-10-24	765.9
Liquid Chromatography	Reversed-phase	XBridge C18 3.5u 2.1x50 mm (eluted)	2025-10-24	995.7
Liquid Chromatography	Reversed-phase	Ascentis Express C18 (eluted)	2025-10-24	566.3
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-24	3277.6
Liquid Chromatography	HILIC	Merck SeQuant ZIC-HILIC (eluted)	2025-10-24	96.4
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC (eluted)	2025-10-24	462.9
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-24	795.6
Liquid Chromatography	HILIC	Merck SeQuant ZIC-HILIC (eluted)	2025-10-24	596.1
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-24	340.6
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-24	238.1
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC column (eluted)	2025-10-24	8.3
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC column (eluted)	2025-10-24	564.0
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-24	621.7
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-24	507.3
Liquid Chromatography	Reversed-phase	Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex (eluted)	2025-10-24	1787.3
Liquid Chromatography	Reversed-phase	Waters Atlantis T3 (2.1 x 150 mm, 5 um) (eluted)	2025-10-24	2253.3

Retention Indices

Not Available

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

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

Microbial Pathways

Pathways

Not Available

Metabolic Reactions

Reactions

This table shows at most 20 reactions. For the full list of associated reactions:

See All Associated Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference

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
Eukaryota/Fungi	Ascomycota	6

Exposure Sources

Other Exposures

Source Type	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									HMDB

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

20118077

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

21158498

PDB ID

Not Available

ChEBI ID

57467

Food Biomarker Ontology

Not Available

CMMC Knowledgebase

Not Available

General References

Lee SH, Blair IA: Oxidative DNA damage and cardiovascular disease. Trends Cardiovasc Med. 2001 Apr-May;11(3-4):148-55. doi: 10.1016/s1050-1738(01)00094-9. [PubMed:11686005 ]
Bansal P, Morgat A, Axelsen KB, Muthukrishnan V, Coudert E, Aimo L, Hyka-Nouspikel N, Gasteiger E, Kerhornou A, Neto TB, Pozzato M, Blatter MC, Ignatchenko A, Redaschi N, Bridge A: Rhea, the reaction knowledgebase in 2022. Nucleic Acids Res. 2022 Jan 7;50(D1):D693-D700. doi: 10.1093/nar/gkab1016. [PubMed:34755880 ]

Showing metabocard for 11-Hydroperoxyoctadeca-9,12-Dienoic Acid (MMDBc0049810)

MOL for #<Metabolite:0x00007f9ad148f3f0>

3D MOL for #<Metabolite:0x00007f9ad148f3f0>

3D SDF for #<Metabolite:0x00007f9ad148f3f0>

3D-SDF for #<Metabolite:0x00007f9ad148f3f0>

PDB for #<Metabolite:0x00007f9ad148f3f0>

3D PDB for #<Metabolite:0x00007f9ad148f3f0>

SMILES for #<Metabolite:0x00007f9ad148f3f0>

INCHI for #<Metabolite:0x00007f9ad148f3f0>

Structure for #<Metabolite:0x00007f9ad148f3f0>

3D Structure for #<Metabolite:0x00007f9ad148f3f0>