MiMeDB: Showing metabocard for (13S)-hydroperoxy-(9Z,11E,15Z)-octadecatrienoic acid (MMDBc0054759)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2022-06-17 19:33:58 UTC

Update Date

2022-08-12 20:09:04 UTC

Metabolite ID

MMDBc0054759

Metabolite Identification

Common Name

(13S)-hydroperoxy-(9Z,11E,15Z)-octadecatrienoic acid

Description

(9Z,11E,13S,15Z)-13-hydroperoxyoctadeca-9,11,15-trienoate, also known as (13S)-hydroperoxy-(9Z,11E,15Z)-octadecatrienoate, 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-hydroperoxyoctadeca-9,11,15-trienoate.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652306172221332D          

 29 28  0  0  1  0            999 V2000
   -1.9584    1.8058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1483    1.6499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8783    0.8704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7125    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2526    1.3381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9825   -0.0651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9825    2.1177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7927   -0.2210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1724    2.2736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3328    0.4027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0681    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6323    1.6499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1429    0.2467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4720    1.3381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8222    1.8058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6830    0.8704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2821    1.1822    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.4931    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0332    1.3381    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7632   -0.0651    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    2.3623    0.2467    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5521    0.4027    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4183    0.2467    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5226    2.7413    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9024    3.0531    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2019   -0.0651    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9024    0.8704    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5521    2.5854    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0121    1.9618    0.0000 H   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  2  0  0  0  0
 12  9  1  0  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
 17 15  1  0  0  0  0
 18 16  1  0  0  0  0
 19 18  2  0  0  0  0
 20 18  1  0  0  0  0
 17 22  1  6  0  0  0
 22 21  1  0  0  0  0
 23  3  1  0  0  0  0
 24  7  1  0  0  0  0
 25  9  1  0  0  0  0
 26 11  1  0  0  0  0
 27 12  1  0  0  0  0
 28 15  1  0  0  0  0
 17 29  1  6  0  0  0
M  CHG  1  20  -1
M  END


  Mrv1652306172221332D          

 29 28  0  0  1  0            999 V2000
   -1.9584    1.8058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1483    1.6499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8783    0.8704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7125    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2526    1.3381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9825   -0.0651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9825    2.1177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7927   -0.2210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1724    2.2736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3328    0.4027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0681    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6323    1.6499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1429    0.2467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4720    1.3381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8222    1.8058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6830    0.8704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2821    1.1822    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.4931    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0332    1.3381    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7632   -0.0651    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    2.3623    0.2467    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5521    0.4027    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4183    0.2467    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5226    2.7413    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9024    3.0531    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2019   -0.0651    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9024    0.8704    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5521    2.5854    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0121    1.9618    0.0000 H   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  2  0  0  0  0
 12  9  1  0  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
 17 15  1  0  0  0  0
 18 16  1  0  0  0  0
 19 18  2  0  0  0  0
 20 18  1  0  0  0  0
 17 22  1  6  0  0  0
 22 21  1  0  0  0  0
 23  3  1  0  0  0  0
 24  7  1  0  0  0  0
 25  9  1  0  0  0  0
 26 11  1  0  0  0  0
 27 12  1  0  0  0  0
 28 15  1  0  0  0  0
 17 29  1  6  0  0  0
M  CHG  1  20  -1
M  END
> <DATABASE_ID>
MMDBc0054759

> <DATABASE_NAME>
MIME

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

> <INCHI_IDENTIFIER>
InChI=1S/C18H30O4/c1-2-3-11-14-17(22-21)15-12-9-7-5-4-6-8-10-13-16-18(19)20/h3,7,9,11-12,15,17,21H,2,4-6,8,10,13-14,16H2,1H3,(H,19,20)/p-1/b9-7-,11-3-,15-12+/t17-/m0/s1

> <INCHI_KEY>
UYQGVDXDXBAABN-FQSPHKRJSA-M

> <FORMULA>
C18H29O4

> <MOLECULAR_WEIGHT>
309.427

> <EXACT_MASS>
309.207132994

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
51

> <JCHEM_AVERAGE_POLARIZABILITY>
36.34704607858382

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
-1

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(9Z,11E,13S,15Z)-13-hydroperoxyoctadeca-9,11,15-trienoate

> <JCHEM_LOGP>
5.278479448

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
11.711074282435678

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.988167201738501

> <JCHEM_PKA_STRONGEST_BASIC>
-4.237376144817387

> <JCHEM_POLAR_SURFACE_AREA>
69.59

> <JCHEM_REFRACTIVITY>
103.3382

> <JCHEM_ROTATABLE_BOND_COUNT>
14

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(9Z,11E,13S,15Z)-13-hydroperoxyoctadeca-9,11,15-trienoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 17-JUN-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-JUN-22         0                                  
HETATM    1  C   UNK     0      -3.656   3.371   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.143   3.080   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.639   1.625   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.930   1.334   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.938   2.498   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.434  -0.121   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.434   3.953   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.946  -0.413   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.922   4.244   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.954   0.752   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.127   1.334   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.914   3.080   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      11.467   0.461   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.881   2.498   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.401   3.371   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      12.475   1.625   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.393   2.207   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      13.987   1.334   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      14.995   2.498   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      14.491  -0.121   0.000  0.00  0.00           O-1
HETATM   21  O   UNK     0       4.410   0.461   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       2.897   0.752   0.000  0.00  0.00           O+0
HETATM   23  H   UNK     0      -2.648   0.461   0.000  0.00  0.00           H+0
HETATM   24  H   UNK     0       8.442   5.117   0.000  0.00  0.00           H+0
HETATM   25  H   UNK     0       5.418   5.699   0.000  0.00  0.00           H+0
HETATM   26  H   UNK     0       0.377  -0.121   0.000  0.00  0.00           H+0
HETATM   27  H   UNK     0       5.418   1.625   0.000  0.00  0.00           H+0
HETATM   28  H   UNK     0       2.897   4.826   0.000  0.00  0.00           H+0
HETATM   29  H   UNK     0       1.889   3.662   0.000  0.00  0.00           H+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2   11   23                                                  
CONECT    4    5    6                                                       
CONECT    5    4    7                                                       
CONECT    6    4    8                                                       
CONECT    7    5    9   24                                                  
CONECT    8    6   10                                                       
CONECT    9    7   12   25                                                  
CONECT   10    8   13                                                       
CONECT   11    3   14   26                                                  
CONECT   12    9   15   27                                                  
CONECT   13   10   16                                                       
CONECT   14   11   17                                                       
CONECT   15   12   17   28                                                  
CONECT   16   13   18                                                       
CONECT   17   14   15   22   29                                             
CONECT   18   16   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18                                                            
CONECT   21   22                                                            
CONECT   22   17   21                                                       
CONECT   23    3                                                            
CONECT   24    7                                                            
CONECT   25    9                                                            
CONECT   26   11                                                            
CONECT   27   12                                                            
CONECT   28   15                                                            
CONECT   29   17                                                            
MASTER        0    0    0    0    0    0    0    0   29    0   56    0
END

Synonyms

Value	Source
(13S)-Hydroperoxy-(9Z,11E,15Z)-octadecatrienoate	ChEBI
(13S)-Hydroperoxy-(9Z,11E,15Z)-octadecatrienoic acid	Generator
(9Z,11E,13S,15Z)-13-Hydroperoxyoctadeca-9,11,15-trienoic acid	Generator

Molecular Formula

C₁₈H₂₉O₄

Average Mass

309.427

Monoisotopic Mass

309.207132994

IUPAC Name

(9Z,11E,13S,15Z)-13-hydroperoxyoctadeca-9,11,15-trienoate

Traditional Name

(9Z,11E,13S,15Z)-13-hydroperoxyoctadeca-9,11,15-trienoate

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C18H30O4/c1-2-3-11-14-17(22-21)15-12-9-7-5-4-6-8-10-13-16-18(19)20/h3,7,9,11-12,15,17,21H,2,4-6,8,10,13-14,16H2,1H3,(H,19,20)/p-1/b9-7-,11-3-,15-12+/t17-/m0/s1

InChI Key

UYQGVDXDXBAABN-FQSPHKRJSA-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:58757 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
logP	5.28	ChemAxon
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	14	ChemAxon
Refractivity	103.34 m³·mol⁻¹	ChemAxon
Polarizability	36.35 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)	2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)	2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)	2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)	2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)	2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)	2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)	2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)	2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)	2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	2022-08-18	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

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

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
Bacteria	Proteobacteria	1	Human ; Human sputum; Human subgingival plaque; Human feces

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

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

26331347

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

45266757

PDB ID

Not Available

ChEBI ID

58757

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

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 (13S)-hydroperoxy-(9Z,11E,15Z)-octadecatrienoic acid (MMDBc0054759)

MOL for #<Metabolite:0x00007fecf46469a8>

3D MOL for #<Metabolite:0x00007fecf46469a8>

3D SDF for #<Metabolite:0x00007fecf46469a8>

3D-SDF for #<Metabolite:0x00007fecf46469a8>

PDB for #<Metabolite:0x00007fecf46469a8>

3D PDB for #<Metabolite:0x00007fecf46469a8>

SMILES for #<Metabolite:0x00007fecf46469a8>

INCHI for #<Metabolite:0x00007fecf46469a8>

Structure for #<Metabolite:0x00007fecf46469a8>

3D Structure for #<Metabolite:0x00007fecf46469a8>