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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2022-07-09 02:13:49 UTC

Update Date

2022-07-09 02:13:49 UTC

HMDB ID

HMDB0340922

Secondary Accession Numbers

None

Metabolite Identification

Common Name

(5Z,9Z,12Z)-octadeca-5,9,12-trienoic acid

Description

(5Z,9Z,12Z)-octadeca-5,9,12-trienoic acid, also known as cis,cis,cis-5,9,12-octadecatrienoic acid or C18:3N-6,9,13, 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 (5Z,9Z,12Z)-octadeca-5,9,12-trienoic acid.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309272006272D          

 20 19  0  0  0  0            999 V2000
10006.514210007.3668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10007.229610007.7791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10007.946910007.3668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10008.771310007.3668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10009.486110007.7791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10010.200610007.3668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10011.025610007.3668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10011.740410007.7791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10012.454810007.3668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10013.169410007.7791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10013.883910007.3668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10014.598610007.7791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10005.800910007.7791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10004.976310007.7791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10004.261010007.3668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.545610007.7791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.832410007.3668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.117010007.7791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.401610007.3668    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10002.117010008.6035    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1 13  1  0  0  0  0
  2  3  1  0  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  2  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
 11 12  1  0  0  0  0
 13 14  2  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
 18 20  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0340922

> <DATABASE_NAME>
hmdb

> <SMILES>
CCCCC\C=C/C\C=C/CC\C=C/CCCC(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C18H30O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h6-7,9-10,13-14H,2-5,8,11-12,15-17H2,1H3,(H,19,20)/b7-6-,10-9-,14-13-

> <INCHI_KEY>
HXQHFNIKBKZGRP-URPRIDOGSA-N

> <FORMULA>
C18H30O2

> <MOLECULAR_WEIGHT>
278.436

> <EXACT_MASS>
278.224580206

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
50

> <JCHEM_AVERAGE_POLARIZABILITY>
34.27629904595861

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(5Z,9Z,12Z)-octadeca-5,9,12-trienoic acid

> <ALOGPS_LOGP>
6.60

> <JCHEM_LOGP>
6.059955137666666

> <ALOGPS_LOGS>
-6.04

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.922347462675991

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
89.63539999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
13

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.52e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
pinolenic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 27-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-SEP-20         0                                  
HETATM    1  C   UNK     0    8678.8268680.418   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8680.1628681.188   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0    8681.5018680.418   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0    8683.0408680.418   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0    8684.3748681.188   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0    8685.7088680.418   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0    8687.2488680.418   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    8688.5828681.188   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8689.9168680.418   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8691.2508681.188   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8692.5838680.418   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8693.9178681.188   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8677.4958681.188   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8675.9568681.188   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8674.6218680.418   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    8673.2858681.188   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0    8671.9548680.418   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0    8670.6188681.188   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0    8669.2838680.418   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0    8670.6188682.726   0.000  0.00  0.00           O+0
CONECT    1    2   13                                                       
CONECT    2    1    3                                                       
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                                                       
CONECT   11   10   12                                                       
CONECT   12   11                                                            
CONECT   13    1   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                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   38    0
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
5Z,9Z,12Z-Octadecatrienoic acid	ChEBI
all-cis-Octadeca-5,9,12-trienoic acid	ChEBI
C18:3N-6,9,13	ChEBI
cis,cis,cis-5,9,12-Octadecatrienoic acid	ChEBI
Pinolenic acid	ChEBI
5Z,9Z,12Z-Octadecatrienoate	Generator
all-cis-Octadeca-5,9,12-trienoate	Generator
cis,cis,cis-5,9,12-Octadecatrienoate	Generator
Pinolenate	Generator
(5Z,9Z,12Z)-Octadeca-5,9,12-trienoate	Generator
5,9,12-Octadecatrienoic acid, (Z,Z,e)-isomer	HMDB
trans-5,9,12-Octadecatrienoic acid	HMDB
5,9,12-Octadecatrienoic acid	HMDB
5,9,12-Octadecatrienoic acid, (cis)-isomer	HMDB
Columbinic acid	HMDB
(5Z,9Z,12Z)-Octadecatrienoic acid	HMDB
(Z,Z,Z)-5,9,12-Octadecatrienoic acid	HMDB
(5Z,9Z,12Z)-5,9,12-Octadecatrienoic acid	HMDB
5,9,12-cis-Octadecatrienoic acid	HMDB
PA	HMDB
FA(18:3(7Z,11Z,14Z))	HMDB

Chemical Formula

C₁₈H₃₀O₂

Average Molecular Weight

278.436

Monoisotopic Molecular Weight

278.224580206

IUPAC Name

(5Z,9Z,12Z)-octadeca-5,9,12-trienoic acid

Traditional Name

pinolenic acid

CAS Registry Number

Not Available

SMILES

CCCCC\C=C/C\C=C/CC\C=C/CCCC(O)=O

InChI Identifier

InChI=1S/C18H30O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h6-7,9-10,13-14H,2-5,8,11-12,15-17H2,1H3,(H,19,20)/b7-6-,10-9-,14-13-

InChI Key

HXQHFNIKBKZGRP-URPRIDOGSA-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
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
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

octadecatrienoic acid (CHEBI:86136 )
Unsaturated fatty acids (LMFA01030344 )

Ontology

Not Available

Not Available

Not Available

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	6.6	ALOGPS
logP	6.06	ChemAxon
logS	-6	ALOGPS
pKa (Strongest Acidic)	4.92	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	37.3 Å²	ChemAxon
Rotatable Bond Count	13	ChemAxon
Refractivity	89.64 m³·mol⁻¹	ChemAxon
Polarizability	34.28 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

Predicted Chromatographic Properties

Predicted Retention Times

Not Available

Predicted Kovats Retention Indices

Not Available

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - (5Z,9Z,12Z)-octadeca-5,9,12-trienoic acid GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2022-08-08	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (5Z,9Z,12Z)-octadeca-5,9,12-trienoic acid 10V, Positive-QTOF	Not Available	2022-08-09	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (5Z,9Z,12Z)-octadeca-5,9,12-trienoic acid 20V, Positive-QTOF	Not Available	2022-08-09	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (5Z,9Z,12Z)-octadeca-5,9,12-trienoic acid 40V, Positive-QTOF	Not Available	2022-08-09	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (5Z,9Z,12Z)-octadeca-5,9,12-trienoic acid 10V, Negative-QTOF	Not Available	2022-08-09	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (5Z,9Z,12Z)-octadeca-5,9,12-trienoic acid 20V, Negative-QTOF	Not Available	2022-08-09	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (5Z,9Z,12Z)-octadeca-5,9,12-trienoic acid 40V, Negative-QTOF	Not Available	2022-08-09	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

4471920

KEGG Compound ID

Not Available

BioCyc ID

CPD-14869

BiGG ID

Not Available

Wikipedia Link

Pinolenic_acid

METLIN ID

Not Available

PubChem Compound

5312495

PDB ID

Not Available

ChEBI ID

86136

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Showing metabocard for (5Z,9Z,12Z)-octadeca-5,9,12-trienoic acid (HMDB0340922)

MOL for HMDB0340922 ((5Z,9Z,12Z)-octadeca-5,9,12-trienoic acid)

3D MOL for HMDB0340922 ((5Z,9Z,12Z)-octadeca-5,9,12-trienoic acid)

3D SDF for HMDB0340922 ((5Z,9Z,12Z)-octadeca-5,9,12-trienoic acid)

3D-SDF for HMDB0340922 ((5Z,9Z,12Z)-octadeca-5,9,12-trienoic acid)

PDB for HMDB0340922 ((5Z,9Z,12Z)-octadeca-5,9,12-trienoic acid)

3D PDB for HMDB0340922 ((5Z,9Z,12Z)-octadeca-5,9,12-trienoic acid)

SMILES for HMDB0340922 ((5Z,9Z,12Z)-octadeca-5,9,12-trienoic acid)

INCHI for HMDB0340922 ((5Z,9Z,12Z)-octadeca-5,9,12-trienoic acid)

Structure for HMDB0340922 ((5Z,9Z,12Z)-octadeca-5,9,12-trienoic acid)

3D Structure for HMDB0340922 ((5Z,9Z,12Z)-octadeca-5,9,12-trienoic acid)

Predicted Retention Times

Predicted Kovats Retention Indices

GC-MS Spectra

MS/MS Spectra