MiMeDB: Showing metabocard for (9Z,12Z)-octadecadienoic acid (MMDBc0054999)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2022-06-17 19:39:33 UTC

Update Date

2024-04-20 06:14:46 UTC

Metabolite ID

MMDBc0054999

Metabolite Identification

Common Name

(9Z,12Z)-octadecadienoic acid

Description

Linoleate, also known as linoleic acid or cis,cis-linoleate, belongs to the class of organic compounds known as lineolic acids and derivatives. These are derivatives of lineolic acid. Lineolic acid is a polyunsaturated omega-6 18 carbon long fatty acid, with two CC double bonds at the 9- and 12-positions. Based on a literature review a significant number of articles have been published on Linoleate.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652306172221392D          

 24 23  0  0  0  0            999 V2000
    2.9980    7.5059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2836    7.0934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2836    6.2684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5691    5.8559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5691    5.0309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8546    4.6184    0.0000 C   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
    1.5691    3.3809    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  5  0  0  0  0  0  0  0  0  0  0
    0.1401    5.0309    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1401    3.3809    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8546    2.1434    0.0000 H   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  1  1  0  0  0  0
  3  2  1  0  0  0  0
  4  3  1  0  0  0  0
  5  4  1  0  0  0  0
  6  5  1  0  0  0  0
  7  6  2  0  0  0  0
  8  7  1  0  0  0  0
  9  8  1  0  0  0  0
 10  9  2  0  0  0  0
 11 10  1  0  0  0  0
 12 11  1  0  0  0  0
 13 12  1  0  0  0  0
 14 13  1  0  0  0  0
 15 14  1  0  0  0  0
 16 15  1  0  0  0  0
 17 16  1  0  0  0  0
 18 17  1  0  0  0  0
 19 18  2  0  0  0  0
 20 18  1  0  0  0  0
 21  6  1  0  0  0  0
 22  7  1  0  0  0  0
 23  9  1  0  0  0  0
 24 10  1  0  0  0  0
M  CHG  1  20  -1
M  END
> <DATABASE_ID>
MMDBc0054999

> <DATABASE_NAME>
MIME

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

> <INCHI_IDENTIFIER>
InChI=1S/C18H32O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h6-7,9-10H,2-5,8,11-17H2,1H3,(H,19,20)/p-1/b7-6-,10-9-

> <INCHI_KEY>
OYHQOLUKZRVURQ-HZJYTTRNSA-M

> <FORMULA>
C18H31O2

> <MOLECULAR_WEIGHT>
279.445

> <EXACT_MASS>
279.232953818

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
51

> <JCHEM_AVERAGE_POLARIZABILITY>
35.175452676336306

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
-1

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(9Z,12Z)-octadeca-9,12-dienoate

> <JCHEM_LOGP>
6.421876794333333

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.988167283903808

> <JCHEM_POLAR_SURFACE_AREA>
40.129999999999995

> <JCHEM_REFRACTIVITY>
99.35589999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
14

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
α-linoleic acid

> <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       5.596  14.011   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.263  13.241   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.263  11.701   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.929  10.931   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.929   9.391   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.595   8.621   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.595   7.081   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.929   6.311   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.929   4.771   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.263   4.001   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.596   4.771   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.930   4.001   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.264   4.771   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.597   4.001   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      10.931   4.771   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      12.265   4.001   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      13.598   4.771   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      14.932   4.001   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      16.266   4.771   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      14.932   2.461   0.000  0.00  0.00           O-1
HETATM   21  H   UNK     0       0.262   9.391   0.000  0.00  0.00           H+0
HETATM   22  H   UNK     0       0.262   6.311   0.000  0.00  0.00           H+0
HETATM   23  H   UNK     0       1.595   4.001   0.000  0.00  0.00           H+0
HETATM   24  H   UNK     0       4.263   2.461   0.000  0.00  0.00           H+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   21                                                  
CONECT    7    6    8   22                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   23                                                  
CONECT   10    9   11   24                                                  
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   20                                                  
CONECT   19   18                                                            
CONECT   20   18                                                            
CONECT   21    6                                                            
CONECT   22    7                                                            
CONECT   23    9                                                            
CONECT   24   10                                                            
MASTER        0    0    0    0    0    0    0    0   24    0   46    0
END

Synonyms

Value	Source
(9Z,12Z)-9,12-Octadecadienoic acid, ion(1-)	ChEBI
(9Z,12Z)-Octadecadienoate	ChEBI
(Z,Z)-9,12-Octadecadienoic acid, ion(1-)	ChEBI
cis,cis-9,12-Octadecadienoate	ChEBI
cis,cis-Linoleate	ChEBI
cis-Delta(9,12)-Octadecadienoate	ChEBI
Linoleic acid, ion(1-)	ChEBI
(9Z,12Z)-9,12-Octadecadienoate, ion(1-)	Generator
(9Z,12Z)-Octadecadienoic acid	Generator
(Z,Z)-9,12-Octadecadienoate, ion(1-)	Generator
cis,cis-9,12-Octadecadienoic acid	Generator
cis,cis-Linoleic acid	Generator
cis-delta(9,12)-Octadecadienoic acid	Generator
cis-Δ(9,12)-octadecadienoate	Generator
cis-Δ(9,12)-octadecadienoic acid	Generator
Linoleate, ion(1-)	Generator
Linoleic acid	Generator
Acid, 9,12-octadecadienoic	MeSH
Linoleic acid, (e,e)-isomer	MeSH
Linoleic acid, (Z,Z)-isomer	MeSH
Linoleic acid, ammonium salt, (Z,Z)-isomer	MeSH
Linoleic acid, potassium salt, (Z,Z)-isomer	MeSH
trans,trans-9,12-Octadecadienoic acid	MeSH
9,12 Octadecadienoic acid	MeSH
Linoleic acid, (Z,e)-isomer	MeSH
Linoleic acid, calcium salt, (Z,Z)-isomer	MeSH
9 trans,12 trans Octadecadienoic acid	MeSH
9-trans,12-trans-Octadecadienoic acid	MeSH
Linoleic acid, sodium salt, (e,e)-isomer	MeSH
Linoleic acid, sodium salt, (Z,Z)-isomer	MeSH
9,12-Octadecadienoic acid	MeSH
Linoelaidic acid	MeSH
Linoelaidic acid, (e,Z)-isomer	MeSH
Linoleic acid, (Z,Z)-isomer, 14C-labeled	MeSH
Linolelaidic acid	MeSH

Molecular Formula

C₁₈H₃₁O₂

Average Mass

279.445

Monoisotopic Mass

279.232953818

IUPAC Name

(9Z,12Z)-octadeca-9,12-dienoate

Traditional Name

α-linoleic acid

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C18H32O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h6-7,9-10H,2-5,8,11-17H2,1H3,(H,19,20)/p-1/b7-6-,10-9-

InChI Key

OYHQOLUKZRVURQ-HZJYTTRNSA-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
Fatty acid
Unsaturated fatty acid
Straight chain fatty acid
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Organic anion
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

octadecadienoate (CHEBI:30245 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
logP	6.42	ChemAxon
pKa (Strongest Acidic)	4.99	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	40.13 Å²	ChemAxon
Rotatable Bond Count	14	ChemAxon
Refractivity	99.36 m³·mol⁻¹	ChemAxon
Polarizability	35.18 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

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
Eukaryota/Fungi	Ascomycota	13	Human feces
Bacteria	Proteobacteria	2	Human ; Human sputum; Human subgingival plaque; Human feces
Eukaryota/Fungi	Basidiomycota	1

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

C00023977

Chemspider ID

4573899

KEGG Compound ID

Not Available

BioCyc ID

LINOLEIC_ACID

BiGG ID

Not Available

Wikipedia Link

Linoleic acid

METLIN ID

Not Available

PubChem Compound

5460332

PDB ID

Not Available

ChEBI ID

30245

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 (9Z,12Z)-octadecadienoic acid (MMDBc0054999)

MOL for #<Metabolite:0x00007fecf463ea28>

3D MOL for #<Metabolite:0x00007fecf463ea28>

3D SDF for #<Metabolite:0x00007fecf463ea28>

3D-SDF for #<Metabolite:0x00007fecf463ea28>

PDB for #<Metabolite:0x00007fecf463ea28>

3D PDB for #<Metabolite:0x00007fecf463ea28>

SMILES for #<Metabolite:0x00007fecf463ea28>

INCHI for #<Metabolite:0x00007fecf463ea28>

Structure for #<Metabolite:0x00007fecf463ea28>

3D Structure for #<Metabolite:0x00007fecf463ea28>