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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (6) Show 6 proteins XML

Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2006-05-22 15:12:30 UTC

Update Date

2022-03-07 02:49:17 UTC

HMDB ID

HMDB0003073

Secondary Accession Numbers

HMDB03073

Metabolite Identification

Common Name

gamma-Linolenic acid

Description

gamma-Linolenic acid, also known as 18:3n6 or GLA, belongs to the class of organic compounds known as linoleic acids and derivatives. These are derivatives of linoleic acid. Linoleic acid is a polyunsaturated omega-6 18-carbon long fatty acid, with two CC double bonds at the 9- and 12-positions. gamma-Linolenic acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. gamma-Linolenic acid is an omega-6 fatty acid produced in the body as the delta 6-desaturase metabolite of linoleic acid. It is converted into dihomo-gamma-linolenic acid, a biosynthetic precursor of monoenoic prostaglandins such as PGE1 (PubChem).

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HMDB0003073
     RDKit          3D
gamma-Linolenic acid
 50 49  0  0  0  0  0  0  0  0999 V2000
   -7.5417    0.9568    0.4497 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9042    0.0403   -0.5524 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8552    0.7491   -1.3807 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7470    1.3044   -0.5455 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0347    0.1826    0.2306 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9679    0.8263    1.0182 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6958    0.5614    0.9132 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1817   -0.4593   -0.0513 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4688   -1.4636    0.7440 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7944   -1.7776    0.6276 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6150   -1.0507   -0.4142 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1416   -2.0062   -1.4015 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3907   -2.1648   -1.6706 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5489   -1.5389   -1.1648 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6895   -0.4920   -0.1650 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2368   -0.2225   -0.0670 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5480    0.8321    0.9232 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9742    2.1263    0.5593 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3599    2.4167   -0.4871 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1136    3.1944    1.4770 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2234    1.6817   -0.0062 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1035    0.3022    1.1695 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8063    1.5062    1.0758 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7122   -0.2648   -1.2688 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5271   -0.8697   -0.0601 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3565    1.5907   -1.8844 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4564    0.0603   -2.1346 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0919    2.0942    0.1426 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0185    1.7837   -1.2402 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8259   -0.2559    0.8928 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7491   -0.5621   -0.5014 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2147    1.6052    1.7739 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9434    1.0608    1.5126 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0102   -1.0210   -0.5567 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6699    0.0892   -0.8195 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0782   -1.9886    1.5043 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2761   -2.5341    1.2441 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9977   -0.2709   -0.8614 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4336   -0.6405    0.1857 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3573   -2.6304   -1.9443 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5819   -2.9841   -2.4883 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1545   -1.1454   -2.0978 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3433   -2.3489   -0.8424 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4927   -0.8083    0.9106 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2697    0.4889   -0.3406 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5491    0.0097   -1.0950 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6586   -1.2123    0.2011 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6667    0.8864    1.0446 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1463    0.4963    1.9237 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8441    3.8669    1.3806 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  2 24  1  0
  2 25  1  0
  3 26  1  0
  3 27  1  0
  4 28  1  0
  4 29  1  0
  5 30  1  0
  5 31  1  0
  6 32  1  0
  7 33  1  0
  8 34  1  0
  8 35  1  0
  9 36  1  0
 10 37  1  0
 11 38  1  0
 11 39  1  0
 12 40  1  0
 13 41  1  0
 14 42  1  0
 14 43  1  0
 15 44  1  0
 15 45  1  0
 16 46  1  0
 16 47  1  0
 17 48  1  0
 17 49  1  0
 20 50  1  0
M  END


  Mrv1652309272007302D          

 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
10005.689510007.3668    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  2  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  1  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>
HMDB0003073

> <DATABASE_NAME>
hmdb

> <SMILES>
CCCCC\C=C/C\C=C/C\C=C/CCCCC(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/h6-7,9-10,12-13H,2-5,8,11,14-17H2,1H3,(H,19,20)/b7-6-,10-9-,13-12-

> <INCHI_KEY>
VZCCETWTMQHEPK-QNEBEIHSSA-N

> <FORMULA>
C18H30O2

> <MOLECULAR_WEIGHT>
278.4296

> <EXACT_MASS>
278.224580204

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
50

> <JCHEM_AVERAGE_POLARIZABILITY>
33.803809270314225

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(6Z,9Z,12Z)-octadeca-6,9,12-trienoic acid

> <ALOGPS_LOGP>
6.59

> <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>
4.922492763245736

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
89.6354

> <JCHEM_ROTATABLE_BOND_COUNT>
13

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.54e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
gamma linolenic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0003073
     RDKit          3D
gamma-Linolenic acid
 50 49  0  0  0  0  0  0  0  0999 V2000
   -7.5417    0.9568    0.4497 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9042    0.0403   -0.5524 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8552    0.7491   -1.3807 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7470    1.3044   -0.5455 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0347    0.1826    0.2306 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9679    0.8263    1.0182 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6958    0.5614    0.9132 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1817   -0.4593   -0.0513 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4688   -1.4636    0.7440 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7944   -1.7776    0.6276 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6150   -1.0507   -0.4142 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1416   -2.0062   -1.4015 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3907   -2.1648   -1.6706 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5489   -1.5389   -1.1648 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6895   -0.4920   -0.1650 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2368   -0.2225   -0.0670 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5480    0.8321    0.9232 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9742    2.1263    0.5593 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3599    2.4167   -0.4871 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1136    3.1944    1.4770 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2234    1.6817   -0.0062 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1035    0.3022    1.1695 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8063    1.5062    1.0758 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7122   -0.2648   -1.2688 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5271   -0.8697   -0.0601 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3565    1.5907   -1.8844 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4564    0.0603   -2.1346 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0919    2.0942    0.1426 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0185    1.7837   -1.2402 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8259   -0.2559    0.8928 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7491   -0.5621   -0.5014 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2147    1.6052    1.7739 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9434    1.0608    1.5126 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0102   -1.0210   -0.5567 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6699    0.0892   -0.8195 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0782   -1.9886    1.5043 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2761   -2.5341    1.2441 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9977   -0.2709   -0.8614 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4336   -0.6405    0.1857 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3573   -2.6304   -1.9443 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5819   -2.9841   -2.4883 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1545   -1.1454   -2.0978 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3433   -2.3489   -0.8424 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4927   -0.8083    0.9106 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2697    0.4889   -0.3406 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5491    0.0097   -1.0950 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6586   -1.2123    0.2011 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6667    0.8864    1.0446 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1463    0.4963    1.9237 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8441    3.8669    1.3806 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  2 24  1  0
  2 25  1  0
  3 26  1  0
  3 27  1  0
  4 28  1  0
  4 29  1  0
  5 30  1  0
  5 31  1  0
  6 32  1  0
  7 33  1  0
  8 34  1  0
  8 35  1  0
  9 36  1  0
 10 37  1  0
 11 38  1  0
 11 39  1  0
 12 40  1  0
 13 41  1  0
 14 42  1  0
 14 43  1  0
 15 44  1  0
 15 45  1  0
 16 46  1  0
 16 47  1  0
 17 48  1  0
 17 49  1  0
 20 50  1  0
M  END

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    8677.2878680.418   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

COMPND    HMDB0003073
HETATM    1  C1  UNL     1      -7.542   0.957   0.450  1.00  0.00           C  
HETATM    2  C2  UNL     1      -6.904   0.040  -0.552  1.00  0.00           C  
HETATM    3  C3  UNL     1      -5.855   0.749  -1.381  1.00  0.00           C  
HETATM    4  C4  UNL     1      -4.747   1.304  -0.546  1.00  0.00           C  
HETATM    5  C5  UNL     1      -4.035   0.183   0.231  1.00  0.00           C  
HETATM    6  C6  UNL     1      -2.968   0.826   1.018  1.00  0.00           C  
HETATM    7  C7  UNL     1      -1.696   0.561   0.913  1.00  0.00           C  
HETATM    8  C8  UNL     1      -1.182  -0.459  -0.051  1.00  0.00           C  
HETATM    9  C9  UNL     1      -0.469  -1.464   0.744  1.00  0.00           C  
HETATM   10  C10 UNL     1       0.794  -1.778   0.628  1.00  0.00           C  
HETATM   11  C11 UNL     1       1.615  -1.051  -0.414  1.00  0.00           C  
HETATM   12  C12 UNL     1       2.142  -2.006  -1.402  1.00  0.00           C  
HETATM   13  C13 UNL     1       3.391  -2.165  -1.671  1.00  0.00           C  
HETATM   14  C14 UNL     1       4.549  -1.539  -1.165  1.00  0.00           C  
HETATM   15  C15 UNL     1       4.689  -0.492  -0.165  1.00  0.00           C  
HETATM   16  C16 UNL     1       6.237  -0.223  -0.067  1.00  0.00           C  
HETATM   17  C17 UNL     1       6.548   0.832   0.923  1.00  0.00           C  
HETATM   18  C18 UNL     1       5.974   2.126   0.559  1.00  0.00           C  
HETATM   19  O1  UNL     1       5.360   2.417  -0.487  1.00  0.00           O  
HETATM   20  O2  UNL     1       6.114   3.194   1.477  1.00  0.00           O  
HETATM   21  H1  UNL     1      -8.223   1.682  -0.006  1.00  0.00           H  
HETATM   22  H2  UNL     1      -8.103   0.302   1.169  1.00  0.00           H  
HETATM   23  H3  UNL     1      -6.806   1.506   1.076  1.00  0.00           H  
HETATM   24  H4  UNL     1      -7.712  -0.265  -1.269  1.00  0.00           H  
HETATM   25  H5  UNL     1      -6.527  -0.870  -0.060  1.00  0.00           H  
HETATM   26  H6  UNL     1      -6.356   1.591  -1.884  1.00  0.00           H  
HETATM   27  H7  UNL     1      -5.456   0.060  -2.135  1.00  0.00           H  
HETATM   28  H8  UNL     1      -5.092   2.094   0.143  1.00  0.00           H  
HETATM   29  H9  UNL     1      -4.019   1.784  -1.240  1.00  0.00           H  
HETATM   30  H10 UNL     1      -4.826  -0.256   0.893  1.00  0.00           H  
HETATM   31  H11 UNL     1      -3.749  -0.562  -0.501  1.00  0.00           H  
HETATM   32  H12 UNL     1      -3.215   1.605   1.774  1.00  0.00           H  
HETATM   33  H13 UNL     1      -0.943   1.061   1.513  1.00  0.00           H  
HETATM   34  H14 UNL     1      -2.010  -1.021  -0.557  1.00  0.00           H  
HETATM   35  H15 UNL     1      -0.670   0.089  -0.819  1.00  0.00           H  
HETATM   36  H16 UNL     1      -1.078  -1.989   1.504  1.00  0.00           H  
HETATM   37  H17 UNL     1       1.276  -2.534   1.244  1.00  0.00           H  
HETATM   38  H18 UNL     1       0.998  -0.271  -0.861  1.00  0.00           H  
HETATM   39  H19 UNL     1       2.434  -0.640   0.186  1.00  0.00           H  
HETATM   40  H20 UNL     1       1.357  -2.630  -1.944  1.00  0.00           H  
HETATM   41  H21 UNL     1       3.582  -2.984  -2.488  1.00  0.00           H  
HETATM   42  H22 UNL     1       5.155  -1.145  -2.098  1.00  0.00           H  
HETATM   43  H23 UNL     1       5.343  -2.349  -0.842  1.00  0.00           H  
HETATM   44  H24 UNL     1       4.493  -0.808   0.911  1.00  0.00           H  
HETATM   45  H25 UNL     1       4.270   0.489  -0.341  1.00  0.00           H  
HETATM   46  H26 UNL     1       6.549   0.010  -1.095  1.00  0.00           H  
HETATM   47  H27 UNL     1       6.659  -1.212   0.201  1.00  0.00           H  
HETATM   48  H28 UNL     1       7.667   0.886   1.045  1.00  0.00           H  
HETATM   49  H29 UNL     1       6.146   0.496   1.924  1.00  0.00           H  
HETATM   50  H30 UNL     1       6.844   3.867   1.381  1.00  0.00           H  
CONECT    1    2   21   22   23
CONECT    2    3   24   25
CONECT    3    4   26   27
CONECT    4    5   28   29
CONECT    5    6   30   31
CONECT    6    7    7   32
CONECT    7    8   33
CONECT    8    9   34   35
CONECT    9   10   10   36
CONECT   10   11   37
CONECT   11   12   38   39
CONECT   12   13   13   40
CONECT   13   14   41
CONECT   14   15   42   43
CONECT   15   16   44   45
CONECT   16   17   46   47
CONECT   17   18   48   49
CONECT   18   19   19   20
CONECT   20   50
END

HMDB0003073
     RDKit          3D
gamma-Linolenic acid
 50 49  0  0  0  0  0  0  0  0999 V2000
   -7.5417    0.9568    0.4497 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9042    0.0403   -0.5524 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8552    0.7491   -1.3807 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7470    1.3044   -0.5455 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0347    0.1826    0.2306 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9679    0.8263    1.0182 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6958    0.5614    0.9132 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1817   -0.4593   -0.0513 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4688   -1.4636    0.7440 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7944   -1.7776    0.6276 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6150   -1.0507   -0.4142 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1416   -2.0062   -1.4015 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3907   -2.1648   -1.6706 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5489   -1.5389   -1.1648 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6895   -0.4920   -0.1650 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2368   -0.2225   -0.0670 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5480    0.8321    0.9232 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9742    2.1263    0.5593 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3599    2.4167   -0.4871 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1136    3.1944    1.4770 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2234    1.6817   -0.0062 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1035    0.3022    1.1695 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8063    1.5062    1.0758 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7122   -0.2648   -1.2688 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5271   -0.8697   -0.0601 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3565    1.5907   -1.8844 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4564    0.0603   -2.1346 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0919    2.0942    0.1426 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0185    1.7837   -1.2402 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8259   -0.2559    0.8928 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7491   -0.5621   -0.5014 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2147    1.6052    1.7739 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9434    1.0608    1.5126 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0102   -1.0210   -0.5567 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6699    0.0892   -0.8195 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0782   -1.9886    1.5043 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2761   -2.5341    1.2441 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9977   -0.2709   -0.8614 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4336   -0.6405    0.1857 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3573   -2.6304   -1.9443 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5819   -2.9841   -2.4883 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1545   -1.1454   -2.0978 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3433   -2.3489   -0.8424 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4927   -0.8083    0.9106 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2697    0.4889   -0.3406 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5491    0.0097   -1.0950 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6586   -1.2123    0.2011 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6667    0.8864    1.0446 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1463    0.4963    1.9237 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8441    3.8669    1.3806 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  2 24  1  0
  2 25  1  0
  3 26  1  0
  3 27  1  0
  4 28  1  0
  4 29  1  0
  5 30  1  0
  5 31  1  0
  6 32  1  0
  7 33  1  0
  8 34  1  0
  8 35  1  0
  9 36  1  0
 10 37  1  0
 11 38  1  0
 11 39  1  0
 12 40  1  0
 13 41  1  0
 14 42  1  0
 14 43  1  0
 15 44  1  0
 15 45  1  0
 16 46  1  0
 16 47  1  0
 17 48  1  0
 17 49  1  0
 20 50  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(6,9,12)-Linolenic acid	ChEBI
(6Z,9Z,12Z)-Octadecatrienoic acid	ChEBI
(Z,Z,Z)-6,9,12-Octadecatrienoic acid	ChEBI
18:3 (N-6)	ChEBI
6,9,12-Octadecatrienoic acid	ChEBI
6-cis,9-cis,12-cis-Octadecatrienoic acid	ChEBI
all-cis-6,9,12-Octadecatrienoic acid	ChEBI
C18:3 (N-6)	ChEBI
C18:3, N-6,9,12 all-cis	ChEBI
cis-Delta(6,9,12)-Octadecatrienoic acid	ChEBI
gamma-Linolensaeure	ChEBI
Gamoleic acid	ChEBI
Gamolenic acid	ChEBI
GLA	ChEBI
Octadeca-6,9,12-triensaeure	ChEBI
(6,9,12)-Linolenate	Generator
(6Z,9Z,12Z)-Octadecatrienoate	Generator
(Z,Z,Z)-6,9,12-Octadecatrienoate	Generator
6,9,12-Octadecatrienoate	Generator
6-cis,9-cis,12-cis-Octadecatrienoate	Generator
all-cis-6,9,12-Octadecatrienoate	Generator
cis-delta(6,9,12)-Octadecatrienoate	Generator
cis-Δ(6,9,12)-octadecatrienoate	Generator
cis-Δ(6,9,12)-octadecatrienoic acid	Generator
g-Linolensaeure	Generator
Γ-linolensaeure	Generator
Gamoleate	Generator
Gamolenate	Generator
g-Linolenate	Generator
g-Linolenic acid	Generator
gamma-Linolenate	Generator
Γ-linolenate	Generator
Γ-linolenic acid	Generator
6(Z),9(Z),12(Z)-Octadecatrienoate	HMDB
6(Z),9(Z),12(Z)-Octadecatrienoic acid	HMDB
6,9,12-all-cis-Octadecatrienoate	HMDB
6,9,12-all-cis-Octadecatrienoic acid	HMDB
6Z,9Z,12Z-Octadecatrienoate	HMDB
6Z,9Z,12Z-Octadecatrienoic acid	HMDB
gamma-Llnolenic acid	HMDB
Ligla	HMDB
Acid, gamma-linolenic	HMDB
Acid, gamolenic	HMDB
gamma Linolenic acid	HMDB
FA(18:3(6Z,9Z,12Z))	HMDB
FA(18:3n6)	HMDB
Linolenate	HMDB
gamma-Linolenic acid	KEGG
(6Z,9Z,12Z)-6,9,12-Octadecatrienoic acid	PhytoBank
(Z,Z,Z)-6,9,12-Octatrienoic acid	PhytoBank
cis,cis,cis-6,9,12-Octadecatrienoic acid	PhytoBank
cis-6,cis-9,cis-12-Octadecatrienoic acid	PhytoBank

Chemical Formula

C₁₈H₃₀O₂

Average Molecular Weight

278.4296

Monoisotopic Molecular Weight

278.224580204

IUPAC Name

(6Z,9Z,12Z)-octadeca-6,9,12-trienoic acid

Traditional Name

gamma linolenic acid

CAS Registry Number

506-26-3

SMILES

CCCCC\C=C/C\C=C/C\C=C/CCCCC(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/h6-7,9-10,12-13H,2-5,8,11,14-17H2,1H3,(H,19,20)/b7-6-,10-9-,13-12-

InChI Key

VZCCETWTMQHEPK-QNEBEIHSSA-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

omega-6 fatty acid (CHEBI:28661 )
linolenic acid (CHEBI:28661 )
Unsaturated fatty acids (C06426 )
Polyunsaturated fatty acids (C06426 )
Unsaturated fatty acids (LMFA01030141 )

Ontology

Not Available

Physical Properties

State

Liquid

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

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M-H]-	Not Available	173.8	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000267
[M+H]+	Not Available	174.523	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000267

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.00025 g/L	ALOGPS
logP	6.59	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	33.8 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 Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	179.169	31661259
DarkChem	[M-H]-	179.838	31661259
DeepCCS	[M+H]+	175.112	30932474
DeepCCS	[M-H]-	172.754	30932474
DeepCCS	[M-2H]-	205.639	30932474
DeepCCS	[M+Na]+	181.205	30932474
AllCCS	[M+H]+	175.5	32859911
AllCCS	[M+H-H2O]+	172.4	32859911
AllCCS	[M+NH4]+	178.4	32859911
AllCCS	[M+Na]+	179.2	32859911
AllCCS	[M-H]-	176.8	32859911
AllCCS	[M+Na-2H]-	178.3	32859911
AllCCS	[M+HCOO]-	180.1	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	8.66 minutes	32390414
Predicted by Siyang on May 30, 2022	24.5972 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.68 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	35.1 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	3035.4 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	627.7 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	254.2 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	452.5 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	675.6 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	1137.9 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	700.5 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	92.3 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	2263.9 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	744.7 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1897.1 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	850.5 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	530.6 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	552.8 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	613.2 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	8.5 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
gamma-Linolenic acid	CCCCC\C=C/C\C=C/C\C=C/CCCCC(O)=O	3384.9	Standard polar	33892256
gamma-Linolenic acid	CCCCC\C=C/C\C=C/C\C=C/CCCCC(O)=O	2006.3	Standard non polar	33892256
gamma-Linolenic acid	CCCCC\C=C/C\C=C/C\C=C/CCCCC(O)=O	2130.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
gamma-Linolenic acid,1TMS,isomer #1	CCCCC/C=C\C/C=C\C/C=C\CCCCC(=O)O[Si](C)(C)C	2192.5	Semi standard non polar	33892256
gamma-Linolenic acid,1TBDMS,isomer #1	CCCCC/C=C\C/C=C\C/C=C\CCCCC(=O)O[Si](C)(C)C(C)(C)C	2436.8	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - gamma-Linolenic acid GC-MS (1 TMS)	splash10-005c-9800000000-7b6e7a36b048f5ed69bd	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - gamma-Linolenic acid GC-EI-TOF (Non-derivatized)	splash10-00b9-9300000000-254ecb989081fdc719d2	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - gamma-Linolenic acid GC-MS (Non-derivatized)	splash10-005c-9800000000-7b6e7a36b048f5ed69bd	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - gamma-Linolenic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9650000000-eec5566c0f0f90bf0049	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - gamma-Linolenic acid GC-MS (1 TMS) - 70eV, Positive	splash10-007c-9431000000-b239852c91e567668780	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - gamma-Linolenic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - gamma-Linolenic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-00nf-9200000000-cf911df79059a750cb2a	2015-03-01	Not Available	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - gamma-Linolenic acid ESI-TOF 20V, Negative-QTOF	splash10-005l-0902100000-6fc8730bd28daa779b66	2017-08-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - gamma-Linolenic acid ESI-TOF 30V, Negative-QTOF	splash10-005l-0902100000-6fc8730bd28daa779b66	2017-08-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - gamma-Linolenic acid ESI-TOF 10V, Negative-QTOF	splash10-005l-0902100000-6fc8730bd28daa779b66	2017-08-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - gamma-Linolenic acid ESI-TOF , Negative-QTOF	splash10-005l-0902100000-6fc8730bd28daa779b66	2017-08-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - gamma-Linolenic acid ESI-TOF 20V, Negative-QTOF	splash10-004i-0090000000-143e6ddfa05656a4c4da	2017-09-12	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - gamma-Linolenic acid ESI-TOF 30V, Negative-QTOF	splash10-004i-0090000000-0b9ba563ad074fe141e8	2017-09-12	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - gamma-Linolenic acid ESI-TOF 10V, Negative-QTOF	splash10-004i-0090000000-63bf7d731625d5577978	2017-09-12	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - gamma-Linolenic acid ESI-TOF 10V, Negative-QTOF	splash10-004i-0090000000-fbc4e202a8b26c91dc9e	2017-09-12	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - gamma-Linolenic acid ESI-TOF , Negative-QTOF	splash10-004i-0090000000-b56d00321ab0921fe7b7	2017-09-12	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - gamma-Linolenic acid LC-ESI-QTOF , negative-QTOF	splash10-004i-0090000000-dcae4273443fd52bbb03	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - gamma-Linolenic acid LC-ESI-TOF , negative-QTOF	splash10-004i-0090000000-143e6ddfa05656a4c4da	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - gamma-Linolenic acid LC-ESI-TOF , negative-QTOF	splash10-004i-0090000000-0b9ba563ad074fe141e8	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - gamma-Linolenic acid LC-ESI-TOF , negative-QTOF	splash10-004i-0090000000-63bf7d731625d5577978	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - gamma-Linolenic acid LC-ESI-QTOF 10V, positive-QTOF	splash10-004i-0090000000-370b301c8afc435a0ce1	2020-07-21	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - gamma-Linolenic acid LC-ESI-QTOF 20V, positive-QTOF	splash10-003s-9850000000-54163d6f895368b9032c	2020-07-21	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - gamma-Linolenic acid LC-ESI-QTOF 40V, positive-QTOF	splash10-001i-9000000000-e6cdb81ac5675944be82	2020-07-21	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - gamma-Linolenic acid 20V, Positive-QTOF	splash10-003s-9750000000-d1947011d4fc6a28a135	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - gamma-Linolenic acid 30V, Positive-QTOF	splash10-004i-0090000000-0b9ba563ad074fe141e8	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - gamma-Linolenic acid 10V, Positive-QTOF	splash10-004i-0090000000-370b301c8afc435a0ce1	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - gamma-Linolenic acid 10V, Positive-QTOF	splash10-01t9-0190000000-6b136607b48b31667801	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - gamma-Linolenic acid 20V, Positive-QTOF	splash10-01q9-4790000000-5046458d5d3e3c228518	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - gamma-Linolenic acid 40V, Positive-QTOF	splash10-05mo-8930000000-852d50a19eb0b0df729b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - gamma-Linolenic acid 10V, Negative-QTOF	splash10-004i-0090000000-ab643cae783eb66bf131	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - gamma-Linolenic acid 20V, Negative-QTOF	splash10-0059-1090000000-abce276de392be9d7d3f	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - gamma-Linolenic acid 40V, Negative-QTOF	splash10-0a4i-9230000000-40a41feed498373e54d2	2016-08-04	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular
Membrane (predicted from logP)

Biospecimen Locations

Blood
Feces

Tissue Locations

Adipose Tissue
Epidermis
Placenta
Platelet

Pathways

Name	SMPDB/PathBank	KEGG
alpha-Linolenic acid metabolism	Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.310 +/- 0.196 uM	Adult (>18 years old)	Both	Normal	18953024 21359215	details
Blood	Detected and Quantified	1.03 +/- 0.005 uM	Adult (>18 years old)	Both	Normal	20671299	details
Blood	Detected and Quantified	1.08 +/- 1.5 uM	Adult (>18 years old)	Both	Normal	21359215	details
Blood	Detected and Quantified	46.1 +/- 21.7 uM	Adult (>18 years old)	Not Specified	Normal	27329611	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	27543620	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	25037050	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	29808030	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Lung cancer	25961003	details
Blood	Detected and Quantified	35.0 +/- 17.7 uM	Adult (>18 years old)	Not Specified	Isovaleric acidemia	27329611	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal cancer	27015276	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal cancer	25037050	details

Associated Disorders and Diseases

Disease References

Lung Cancer
Chen Y, Ma Z, Min L, Li H, Wang B, Zhong J, Dai L: Biomarker identification and pathway analysis by serum metabolomics of lung cancer. Biomed Res Int. 2015;2015:183624. doi: 10.1155/2015/183624. Epub 2015 Apr 16. [PubMed:25961003 ]
Isovaleric acidemia
Dercksen M, Kulik W, Mienie LJ, Reinecke CJ, Wanders RJ, Duran M: Polyunsaturated fatty acid status in treated isovaleric acidemia patients. Eur J Clin Nutr. 2016 Oct;70(10):1123-1126. doi: 10.1038/ejcn.2016.100. Epub 2016 Jun 22. [PubMed:27329611 ]
Colorectal cancer
Sinha R, Ahn J, Sampson JN, Shi J, Yu G, Xiong X, Hayes RB, Goedert JJ: Fecal Microbiota, Fecal Metabolome, and Colorectal Cancer Interrelations. PLoS One. 2016 Mar 25;11(3):e0152126. doi: 10.1371/journal.pone.0152126. eCollection 2016. [PubMed:27015276 ] Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]

Associated OMIM IDs

211980 (Lung Cancer)
243500 (Isovaleric acidemia)
114500 (Colorectal cancer)

External Links

DrugBank ID

DB13854

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Wikipedia Link

METLIN ID

PubChem Compound

PDB ID

Not Available

ChEBI ID

28661

Food Biomarker Ontology

Not Available

VMH ID

DLNLCGCRN

MarkerDB ID

MDB00000409

Good Scents ID

Not Available

References

Synthesis Reference

Gema H; Kavadia A; Dimou D; Tsagou V; Komaitis M; Aggelis G Production of gamma-linolenic acid by Cunninghamella echinulata cultivated on glucose and orange peel. Applied microbiology and biotechnology (2002), 58(3), 303-7.

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

Melnik BC, Plewig G: Is the origin of atopy linked to deficient conversion of omega-6-fatty acids to prostaglandin E1? J Am Acad Dermatol. 1989 Sep;21(3 Pt 1):557-63. [PubMed:2550526 ]
Levy RJ, Lian JB: gamma-Carboxyglutamate excretion and warfarin therapy. Clin Pharmacol Ther. 1979 May;25(5 Pt 1):562-70. [PubMed:373941 ]
Bolton-Smith C, Woodward M, Tavendale R: Evidence for age-related differences in the fatty acid composition of human adipose tissue, independent of diet. Eur J Clin Nutr. 1997 Sep;51(9):619-24. [PubMed:9306089 ]
Purasiri P, Mckechnie A, Heys SD, Eremin O: Modulation in vitro of human natural cytotoxicity, lymphocyte proliferative response to mitogens and cytokine production by essential fatty acids. Immunology. 1997 Oct;92(2):166-72. [PubMed:9415022 ]
Ziboh VA, Miller CC, Cho Y: Metabolism of polyunsaturated fatty acids by skin epidermal enzymes: generation of antiinflammatory and antiproliferative metabolites. Am J Clin Nutr. 2000 Jan;71(1 Suppl):361S-6S. [PubMed:10617998 ]
Magnusson G, Boberg M, Cederblad G, Meurling S: Plasma and tissue levels of lipids, fatty acids and plasma carnitine in neonates receiving a new fat emulsion. Acta Paediatr. 1997 Jun;86(6):638-44. [PubMed:9202801 ]
Kankaanpaa PE, Salminen SJ, Isolauri E, Lee YK: The influence of polyunsaturated fatty acids on probiotic growth and adhesion. FEMS Microbiol Lett. 2001 Jan 15;194(2):149-53. [PubMed:11164299 ]
Whitaker DK, Cilliers J, de Beer C: Evening primrose oil (Epogam) in the treatment of chronic hand dermatitis: disappointing therapeutic results. Dermatology. 1996;193(2):115-20. [PubMed:8884146 ]
Kankaanpaa P, Nurmela K, Erkkila A, Kalliomaki M, Holmberg-Marttila D, Salminen S, Isolauri E: Polyunsaturated fatty acids in maternal diet, breast milk, and serum lipid fatty acids of infants in relation to atopy. Allergy. 2001 Jul;56(7):633-8. [PubMed:11421921 ]
Koletzko B, Sauerwald U, Keicher U, Saule H, Wawatschek S, Bohles H, Bervoets K, Fleith M, Crozier-Willi G: Fatty acid profiles, antioxidant status, and growth of preterm infants fed diets without or with long-chain polyunsaturated fatty acids. A randomized clinical trial. Eur J Nutr. 2003 Oct;42(5):243-53. [PubMed:14569405 ]
Leigh-Firbank EC, Minihane AM, Leake DS, Wright JW, Murphy MC, Griffin BA, Williams CM: Eicosapentaenoic acid and docosahexaenoic acid from fish oils: differential associations with lipid responses. Br J Nutr. 2002 May;87(5):435-45. [PubMed:12010583 ]
Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]

Enzymes

Enzyme Details

1. Bile acid-CoA:amino acid N-acyltransferase

General function:: Involved in thiolester hydrolase activity
Specific function:: Involved in bile acid metabolism. In liver hepatocytes catalyzes the second step in the conjugation of C24 bile acids (choloneates) to glycine and taurine before excretion into bile canaliculi. The major components of bile are cholic acid and chenodeoxycholic acid. In a first step the bile acids are converted to an acyl-CoA thioester, either in peroxisomes (primary bile acids deriving from the cholesterol pathway), or cytoplasmic at the endoplasmic reticulum (secondary bile acids). May catalyze the conjugation of primary or secondary bile acids, or both. The conjugation increases the detergent properties of bile acids in the intestine, which facilitates lipid and fat-soluble vitamin absorption. In turn, bile acids are deconjugated by bacteria in the intestine and are recycled back to the liver for reconjugation (secondary bile acids). May also act as an acyl-CoA thioesterase that regulates intracellular levels of free fatty acids. In vitro, catalyzes the hydrolysis of long- and very long-chain saturated acyl-CoAs to the free fatty acid and coenzyme A (CoASH), and conjugates glycine to these acyl-CoAs.
Gene Name:: BAAT
Uniprot ID:: Q14032
Molecular weight:: 46298.865

Enzyme Details

2. Cytosolic acyl coenzyme A thioester hydrolase

General function:: Lipid transport and metabolism
Specific function:: Acyl-CoA thioesterases are a group of enzymes that catalyze the hydrolysis of acyl-CoAs to the free fatty acid and coenzyme A (CoASH), providing the potential to regulate intracellular levels of acyl-CoAs, free fatty acids and CoASH. May play an important physiological function in brain. May play a regulatory role by modulating the cellular levels of fatty acyl-CoA ligands for certain transcription factors as well as the substrates for fatty acid metabolizing enzymes, contributing to lipid homeostasis. Has broad specificity, active towards fatty acyl-CoAs with chain-lengths of C8-C18. Has a maximal activity toward palmitoyl-CoA.
Gene Name:: ACOT7
Uniprot ID:: O00154
Molecular weight:: 40454.945

Reactions

Gamma-linolenoyl-CoA + Water → Coenzyme A + gamma-Linolenic acid	details

Enzyme Details

3. Acyl-coenzyme A thioesterase 2, mitochondrial

General function:: Involved in thiolester hydrolase activity
Specific function:: Acyl-CoA thioesterases are a group of enzymes that catalyze the hydrolysis of acyl-CoAs to the free fatty acid and coenzyme A (CoASH), providing the potential to regulate intracellular levels of acyl-CoAs, free fatty acids and CoASH. Displays high levels of activity on medium- and long chain acyl CoAs.
Gene Name:: ACOT2
Uniprot ID:: P49753
Molecular weight:: 53218.02

Reactions

Gamma-linolenoyl-CoA + Water → Coenzyme A + gamma-Linolenic acid	details

Enzyme Details

4. Acyl-coenzyme A thioesterase 4

General function:: Involved in thiolester hydrolase activity
Specific function:: Acyl-CoA thioesterases are a group of enzymes that catalyze the hydrolysis of acyl-CoAs to the free fatty acid and coenzyme A (CoASH), providing the potential to regulate intracellular levels of acyl-CoAs, free fatty acids and CoASH (By similarity). Succinyl-CoA thioesterase that also hydrolyzes long chain saturated and unsaturated monocarboxylic acyl-CoAs.
Gene Name:: ACOT4
Uniprot ID:: Q8N9L9
Molecular weight:: 46326.09

Reactions

Gamma-linolenoyl-CoA + Water → Coenzyme A + gamma-Linolenic acid	details

Enzyme Details

5. Acyl-coenzyme A thioesterase 8

General function:: Involved in acyl-CoA thioesterase activity
Specific function:: Acyl-CoA thioesterases are a group of enzymes that catalyze the hydrolysis of acyl-CoAs to the free fatty acid and coenzyme A (CoASH), providing the potential to regulate intracellular levels of acyl-CoAs, free fatty acids and CoASH. May mediate Nef-induced down-regulation of CD4. Major thioesterase in peroxisomes. Competes with BAAT (Bile acid CoA: amino acid N-acyltransferase) for bile acid-CoA substrate (such as chenodeoxycholoyl-CoA). Shows a preference for medium-length fatty acyl-CoAs (By similarity). May be involved in the metabolic regulation of peroxisome proliferation.
Gene Name:: ACOT8
Uniprot ID:: O14734
Molecular weight:: 35914.02

Enzyme Details

6. Acyl-coenzyme A thioesterase 1

General function:: Involved in thiolester hydrolase activity
Specific function:: Acyl-CoA thioesterases are a group of enzymes that catalyze the hydrolysis of acyl-CoAs to the free fatty acid and coenzyme A (CoASH), providing the potential to regulate intracellular levels of acyl-CoAs, free fatty acids and CoASH. Active towards fatty acyl-CoA with chain-lengths of C12-C16 (By similarity).
Gene Name:: ACOT1
Uniprot ID:: Q86TX2
Molecular weight:: 46276.96

Reactions

Gamma-linolenoyl-CoA + Water → Coenzyme A + gamma-Linolenic acid	details

Showing metabocard for gamma-Linolenic acid (HMDB0003073)

MOL for HMDB0003073 (gamma-Linolenic acid)

3D MOL for HMDB0003073 (gamma-Linolenic acid)

3D SDF for HMDB0003073 (gamma-Linolenic acid)

3D-SDF for HMDB0003073 (gamma-Linolenic acid)

PDB for HMDB0003073 (gamma-Linolenic acid)

3D PDB for HMDB0003073 (gamma-Linolenic acid)

SMILES for HMDB0003073 (gamma-Linolenic acid)

INCHI for HMDB0003073 (gamma-Linolenic acid)

Structure for HMDB0003073 (gamma-Linolenic acid)

3D Structure for HMDB0003073 (gamma-Linolenic acid)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

Enzymes

Reactions

Reactions

Reactions

Reactions