MiMeDB: Showing metabocard for gamma-Linolenic acid (MMDBc0000568)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2020-12-10 18:40:43 UTC

Update Date

2022-08-31 06:09:47 UTC

Metabolite ID

MMDBc0000568

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>
MMDBc0000568

> <DATABASE_NAME>
MIME

> <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

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

Molecular Formula

C₁₈H₃₀O₂

Average Mass

278.4296

Monoisotopic Mass

278.224580204

IUPAC Name

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

Traditional Name

gamma linolenic acid

CAS Registry Number

Not Available

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 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted 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

Spectra

Chromatographic Retention Times and Retention Indices

Retention Times

Not Available

Retention Indices

Not Available

Chromatographic Retention Times and Retention Indices

Retention Times

Not Available

Retention Indices

Not Available

Biological Properties

Cellular Locations

Cytoplasm
Extracellular
Membrane

Biospecimen Locations

Adipose Tissue
Blood
Epidermis
Feces
Placenta
Platelet

Tissue Locations

Adipose Tissue
Epidermis
Placenta
Platelet

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species
MMDBp0192196	Bile acid-CoA:amino acid N-acyltransferase	Enzyme	Q14032	Homo_sapiens
MMDBp0192655	Cytosolic acyl coenzyme A thioester hydrolase	Enzyme	O00154	Homo_sapiens
MMDBp0192656	Acyl-coenzyme A thioesterase 2, mitochondrial	Enzyme	P49753	Homo_sapiens
MMDBp0192657	Acyl-coenzyme A thioesterase 4	Enzyme	Q8N9L9	Homo_sapiens
MMDBp0192658	Acyl-coenzyme A thioesterase 8	Enzyme	O14734	Homo_sapiens
MMDBp0196516	Acyl-coenzyme A thioesterase 1	Enzyme	Q86TX2	Homo_sapiens

Human Pathways

Pathways

Name	SMPDB/PathBank

Microbial Pathways

Pathways

Not Available

Metabolic Reactions

Reactions

This table shows at most 20 reactions. For the full list of associated reactions:

See All Associated 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
Isovaleric acidemia	Slight Decrease	Association	Human Blood	HMDB	27329611

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria	Firmicutes	1	Human	Indirect association between microbiota composition and metabolites measured in host biospecimen

Exposure Sources

Other Exposures

Source Type	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Age	Sex	Health Condition	Data Source	Reference
Human Feces	Detected but not Quantified						HMDB
Human	Detected and Quantified	35.0	17.7	Adult (>18 years old)	Not Specified	Isovaleric acidemia	HMDB	27329611
Human	Detected and Quantified	0.310	0.196	Adult (>18 years old)	Both	Normal	HMDB	18953024
Human	Detected and Quantified	0.310	0.196	Adult (>18 years old)	Both	Normal	HMDB	21359215
Human	Detected and Quantified	1.03	0.005	Adult (>18 years old)	Both	Normal	HMDB	20671299
Human	Detected and Quantified	1.08	1.5	Adult (>18 years old)	Both	Normal	HMDB	21359215
Human	Detected and Quantified	46.1	21.7	Adult (>18 years old)	Not Specified	Normal	HMDB	27329611
Human Adipose Tissue	Detected but not Quantified			Not Specified	Not Specified	Normal	HMDB	34986597
Human Epidermis	Detected but not Quantified			Not Specified	Not Specified	Normal	HMDB	34986597
Human Placenta	Detected but not Quantified			Not Specified	Not Specified	Normal	HMDB	34986597
Human Platelet	Detected but not Quantified			Not Specified	Not Specified	Normal	HMDB	34986597
Human Feces	Detected but not Quantified			Adult (>18 years old)	Both	Normal	HMDB	27543620
Human Feces	Detected but not Quantified			Adult (>18 years old)	Both	Normal	HMDB	25037050
Human Feces	Detected but not Quantified			Adult (>18 years old)	Both	Normal	HMDB	29808030

External Links

HMDB ID

HMDB0003073

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

CMMC Knowledgebase

Not Available

General References

Levy RJ, Lian JB: gamma-Carboxyglutamate excretion and warfarin therapy. Clin Pharmacol Ther. 1979 May;25(5 Pt 1):562-70. doi: 10.1002/cpt1979255part1562. [PubMed:373941 ]
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. doi: 10.1016/s0190-9622(89)70226-7. [PubMed:2550526 ]
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. doi: 10.1159/000246224. [PubMed:8884146 ]
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. doi: 10.1111/j.1651-2227.1997.tb08948.x. [PubMed:9202801 ]
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. doi: 10.1038/sj.ejcn.1600455. [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. doi: 10.1046/j.1365-2567.1997.d01-2308.x. [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. doi: 10.1093/ajcn/71.1.361s. [PubMed:10617998 ]
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. doi: 10.1111/j.1574-6968.2001.tb09460.x. [PubMed:11164299 ]
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. doi: 10.1034/j.1398-9995.2001.00965.x. [PubMed:11421921 ]
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. doi: 10.1079/BJNBJN2002556. [PubMed:12010583 ]
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. doi: 10.1007/s00394-003-0418-2. [PubMed:14569405 ]
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 ]

Showing metabocard for gamma-Linolenic acid (MMDBc0000568)

MOL for #<Metabolite:0x00007f1219144470>

3D MOL for #<Metabolite:0x00007f1219144470>

3D SDF for #<Metabolite:0x00007f1219144470>

3D-SDF for #<Metabolite:0x00007f1219144470>

PDB for #<Metabolite:0x00007f1219144470>

3D PDB for #<Metabolite:0x00007f1219144470>

SMILES for #<Metabolite:0x00007f1219144470>

INCHI for #<Metabolite:0x00007f1219144470>

Structure for #<Metabolite:0x00007f1219144470>

3D Structure for #<Metabolite:0x00007f1219144470>