MiMeDB: Showing metabocard for 13-hydroperoxy-(9Z,11E)-octadecadienoic acid (MMDBc0054709)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2022-06-06 16:15:12 UTC

Update Date

2022-08-12 20:09:03 UTC

Metabolite ID

MMDBc0054709

Metabolite Identification

Common Name

13-hydroperoxy-(9Z,11E)-octadecadienoic acid

Description

Structure

MOL SDF PDB SMILES InChI


  Mrv1652303231706042D          

 26 25  0  0  0  0            999 V2000
    5.1414   -1.3184    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4270   -0.9059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7125   -1.3184    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  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
    4.4270   -0.0809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1414    0.3316    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7125    0.3316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9980   -0.0809    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7125    1.1566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4270    1.5691    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9980    1.5691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2836    1.1566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5691    1.5691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8546    1.1566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1401    1.5691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5743    1.1566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9980    2.3941    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7125    2.8066    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  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
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  2  0  0  0  0
  2 13  2  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  2  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 19 25  1  0  0  0  0
 25 26  1  0  0  0  0
M  CHG  1  11  -1
M  END


  Mrv1652303231706042D          

 26 25  0  0  0  0            999 V2000
    5.1414   -1.3184    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4270   -0.9059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7125   -1.3184    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  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
    4.4270   -0.0809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1414    0.3316    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7125    0.3316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9980   -0.0809    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7125    1.1566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4270    1.5691    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9980    1.5691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2836    1.1566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5691    1.5691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8546    1.1566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1401    1.5691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5743    1.1566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9980    2.3941    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7125    2.8066    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  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
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  2  0  0  0  0
  2 13  2  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  2  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 19 25  1  0  0  0  0
 25 26  1  0  0  0  0
M  CHG  1  11  -1
M  END
> <DATABASE_ID>
MMDBc0054709

> <DATABASE_NAME>
MIME

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

> <INCHI_IDENTIFIER>
InChI=1S/C18H32O4/c1-2-3-11-14-17(22-21)15-12-9-7-5-4-6-8-10-13-16-18(19)20/h7,9,12,15,17,21H,2-6,8,10-11,13-14,16H2,1H3,(H,19,20)/p-1/b9-7-,15-12+

> <INCHI_KEY>
JDSRHVWSAMTSSN-BSZOFBHHSA-M

> <FORMULA>
C18H31O4

> <MOLECULAR_WEIGHT>
311.443

> <EXACT_MASS>
311.222783058

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
53

> <JCHEM_AVERAGE_POLARIZABILITY>
37.89430178176629

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
-1

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(9Z,11E)-13-hydroperoxyoctadeca-9,11-dienoate

> <ALOGPS_LOGP>
5.85

> <JCHEM_LOGP>
5.640401104666667

> <ALOGPS_LOGS>
-5.30

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
11.712374089551586

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.988167201984285

> <JCHEM_PKA_STRONGEST_BASIC>
-4.2368076090774425

> <JCHEM_POLAR_SURFACE_AREA>
69.59

> <JCHEM_REFRACTIVITY>
102.2216

> <JCHEM_ROTATABLE_BOND_COUNT>
15

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.67e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(9Z,11E)-13-hydroperoxyoctadeca-9,11-dienoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 23-MAR-17   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-MAR-17         0                                  
HETATM    1  H   UNK     0       9.597  -2.461   0.000  0.00  0.00           H+0
HETATM    2  C   UNK     0       8.264  -1.691   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.930  -2.461   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       8.264  -4.771   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.597  -4.001   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      10.931  -4.771   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      12.265  -4.001   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      13.598  -4.771   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      14.932  -4.001   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      16.266  -4.771   0.000  0.00  0.00           O-1
HETATM   12  O   UNK     0      14.932  -2.461   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       8.264  -0.151   0.000  0.00  0.00           C+0
HETATM   14  H   UNK     0       9.597   0.619   0.000  0.00  0.00           H+0
HETATM   15  C   UNK     0       6.930   0.619   0.000  0.00  0.00           C+0
HETATM   16  H   UNK     0       5.596  -0.151   0.000  0.00  0.00           H+0
HETATM   17  C   UNK     0       6.930   2.159   0.000  0.00  0.00           C+0
HETATM   18  H   UNK     0       8.264   2.929   0.000  0.00  0.00           H+0
HETATM   19  C   UNK     0       5.596   2.929   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.263   2.159   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.929   2.929   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       1.595   2.159   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       0.262   2.929   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -1.072   2.159   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       5.596   4.469   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0       6.930   5.239   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   13                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10                                                            
CONECT   13    2   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20   25                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23                                                            
CONECT   25   19   26                                                       
CONECT   26   25                                                            
MASTER        0    0    0    0    0    0    0    0   26    0   50    0
END

Synonyms

Value	Source
13-Hydroperoxy-(9Z,11E)-octadecadienoate	HMDB
13-Hydroperoxy-(9Z,11E)-octadecadienoic acid	HMDB

Molecular Formula

C₁₈H₃₁O₄

Average Mass

311.443

Monoisotopic Mass

311.222783058

IUPAC Name

(9Z,11E)-13-hydroperoxyoctadeca-9,11-dienoate

Traditional Name

(9Z,11E)-13-hydroperoxyoctadeca-9,11-dienoate

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C18H32O4/c1-2-3-11-14-17(22-21)15-12-9-7-5-4-6-8-10-13-16-18(19)20/h7,9,12,15,17,21H,2-6,8,10-11,13-14,16H2,1H3,(H,19,20)/p-1/b9-7-,15-12+

InChI Key

JDSRHVWSAMTSSN-BSZOFBHHSA-M

Chemical Taxonomy

Description

This compound 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

Not Available

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	0.0017 g/L	ALOGPS
logP	5.85	ALOGPS
logP	5.64	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	102.22 m³·mol⁻¹	ChemAxon
Polarizability	37.89 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

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-01ox-0093000000-8bf4f7b1e5a824321064	2017-10-06	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0007-1290000000-d535382b27a48e5ef51e	2017-10-06	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0002-5980000000-779087c6278b2c701471	2017-10-06	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
Eukaryota/Fungi	Ascomycota	1

Exposure Sources

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference

External Links

HMDB ID

HMDB62637

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

102571771

PDB ID

Not Available

ChEBI ID

90823

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 13-hydroperoxy-(9Z,11E)-octadecadienoic acid (MMDBc0054709)

MOL for #<Metabolite:0x00007fdb705142a0>

3D MOL for #<Metabolite:0x00007fdb705142a0>

3D SDF for #<Metabolite:0x00007fdb705142a0>

3D-SDF for #<Metabolite:0x00007fdb705142a0>

PDB for #<Metabolite:0x00007fdb705142a0>

3D PDB for #<Metabolite:0x00007fdb705142a0>

SMILES for #<Metabolite:0x00007fdb705142a0>

INCHI for #<Metabolite:0x00007fdb705142a0>

Structure for #<Metabolite:0x00007fdb705142a0>

3D Structure for #<Metabolite:0x00007fdb705142a0>