NP-MRD: Showing NP-Card for Gamma-linolenic acid (NP0044240)

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Record Information

Version

1.0

Created at

2022-02-14 20:33:36 UTC

Updated at

2022-03-10 22:20:54 UTC

NP-MRD ID

NP0044240

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Gamma-linolenic acid

Description

Gamma-Linolenic acid is also known as 18:3 (N-6), gamolenic acid or gamma-linolensaeure. It is an omega-6 polyunsaturated fatty acid (PUFA) also referred to as 9,12-octadecatrienoic acid (cis-6, cis-9, cis-12- octadecatrienoic acid). It 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. Gamma-Linolenic acid is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. It is found largely in human milk and other botanical sources. Gamma-Linolenic acid is found in varying amounts in edible hemp seeds, oats, barley and spirulina. Gamma-linolenic acid is one of the unsaturated fatty acids found in the oil of cannabis seeds (PMID: 6991645 ). Gamolenic acid is also found in some fungal sources and is present naturally in the form of triglycerides. Gamolenic acid may be found in over-the-counter dietary supplements. 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 Prostaglandin E1(PGE1). Evening primrose oil, containing 7-14% gamma-linolenic acid, has been investigated for clinical use in menopausal syndrome, diabetic neuropathy, breast pain (PMID: 27083549 ) And eczema. It has been questioned if evening primrose oil, containing gamma-linolenic acid, helped alleviate atopic eczema (PMID: 14670851 ). However, its effectiveness in treating eczema was demonstrated in a study where the topical application of borage seed oil (with higher concentrations of gamma linolenic acid than evening primrose oil) reduced symptoms of atopic dermatitis in a double-blind, placebo-controlled clinical trial (PMID: 18078406 ).Various clinical indications of gamolenic acid have been studied, including rheumatoid arthritis, atopic eczema, acute respiratory distress syndrome, asthma, premenstrual syndrome, cardiovascular disease, ulcerative colitis, ADHD, cancer, osteoporosis, diabetic neuropathy, and insomnia ( PMID: 27083549 ; PMID: 27083549 ).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 50 49  0  0  0  0  0  0  0  0999 V2000
   -5.4112   -2.1946    0.0300 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2075   -0.9578    0.3492 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5142   -0.1190   -0.8635 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3148    0.3806   -1.5852 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4193    1.2616   -0.7280 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3011    1.6570   -1.5990 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0385    1.4306   -1.4244 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5663    0.6864   -0.2215 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6538    1.6071    0.4971 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5978    1.3315    0.7150 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2147    0.0716    0.2608 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7138   -0.6154    1.4994 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9567   -0.9341    1.7288 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0255   -0.6460    0.7735 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0053    0.2726    1.4820 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1662    0.7172    0.6970 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1242   -0.2941    0.1934 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6414   -1.3174   -0.7126 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7895   -2.5558   -0.4668 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9904   -0.9499   -1.8982 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3732   -2.1333    0.4584 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8528   -3.1087    0.5019 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3896   -2.3879   -1.0501 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2051   -1.3213    0.7278 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7971   -0.3714    1.1991 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1198   -0.7520   -1.5406 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1742    0.7060   -0.5215 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6509    0.9030   -2.5028 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6933   -0.4810   -1.9265 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9871    2.2131   -0.5324 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2025    0.7268    0.1817 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5863    2.2144   -2.5087 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3031    1.7661   -2.1290 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1735   -0.2810   -0.4957 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3819    0.4787    0.5167 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0463    2.5859    0.8706 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2064    2.0792    1.2624 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5403   -0.6229   -0.2173 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0197    0.2633   -0.4869 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9590   -0.8517    2.2388 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2331   -1.4286    2.6518 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7823   -0.2037   -0.1738 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5978   -1.6216    0.6490 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4163    1.1845    1.7639 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3239   -0.2326    2.4441 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7076    1.4846    1.3235 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7695    1.3470   -0.1638 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9898    0.2314   -0.3129 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5861   -0.8131    1.0865 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0062   -1.0907   -2.0412 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 20  1  0
 18 19  2  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>
NP0044240

> <DATABASE_NAME>
NP-MRD

> <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

$$$$

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

View in JSmol

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 Mass

278.4296 Da

Monoisotopic Mass

278.22458 Da

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

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Abies pinsapo	LOTUS Database	35616633
Agaricus blazei	LOTUS Database	35616633
Apis cerana	LOTUS Database	35616633
Arabidopsis thaliana	LOTUS Database	35616633
Borago officinalis	LOTUS Database	35616633
Brassica rapa	LOTUS Database	35616633
Cannabis sativa	CannabisDB	Not Available
Chlamydomonas reinhardtii	LOTUS Database	35616633
Cunninghamella japonica	LOTUS Database	35616633
Dicranum japonicum	LOTUS Database	35616633
Echium auberianum	Plant	KNApSAcK
Echium boissieri	Plant	KNApSAcK
Echium gentianoides	Plant	KNApSAcK
Echium giganteum	Plant	KNApSAcK
Echium lusitanicum	Plant	KNApSAcK
Echium pitardii	Plant	KNApSAcK
Echium plantagineum	Plant	KNApSAcK
Echium sabulicola	Plant	KNApSAcK
Echium strictum	Plant	KNApSAcK
Echium vulgare	Plant	KNApSAcK
Eurhynchium striatum	LOTUS Database	35616633
Gracilaria gracilis	LOTUS Database	35616633
Hippophae rhamnoides	LOTUS Database	35616633
Homo sapiens (Serum)	Animalia	KNApSAcK
Lithothamnion corallioides	--	KNApSAcK
Malva sylvestris	LOTUS Database	35616633
Mortierella hygrophila	LOTUS Database	35616633
Mus musculus	LOTUS Database	35616633
Oenothera biennis	LOTUS Database	35616633
Oenothera stricta	LOTUS Database	35616633
Punica granatum	Plant	KNApSAcK
Ribes nigrum	LOTUS Database	35616633
Scrophularia rubricaulis	LOTUS Database	35616633
Youngia tenuicaulis	LOTUS Database	35616633

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 )

Physical Properties

State

Not Available

Experimental 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

Predicted Properties

Property	Value	Source
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

External Links

HMDB ID

HMDB0003073

DrugBank ID

DB13854

Phenol Explorer Compound ID

Not Available

FoodDB 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

Good Scents ID

Not Available

References

General References

Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. [PubMed:6991645 ]
Jensen RG: The composition of bovine milk lipids: January 1995 to December 2000. J Dairy Sci. 2002 Feb;85(2):295-350. doi: 10.3168/jds.S0022-0302(02)74079-4. [PubMed:11913692 ]
Jensen RG, Ferris AM, Lammi-Keefe CJ: The composition of milk fat. J Dairy Sci. 1991 Sep;74(9):3228-43. doi: 10.3168/jds.S0022-0302(91)78509-3. [PubMed:1779072 ]
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 ]
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 ]
Sergeant S, Rahbar E, Chilton FH: Gamma-linolenic acid, Dihommo-gamma linolenic, Eicosanoids and Inflammatory Processes. Eur J Pharmacol. 2016 Aug 15;785:77-86. doi: 10.1016/j.ejphar.2016.04.020. Epub 2016 Apr 12. [PubMed:27083549 ]
Williams HC: Evening primrose oil for atopic dermatitis. BMJ. 2003 Dec 13;327(7428):1358-9. doi: 10.1136/bmj.327.7428.1358. [PubMed:14670851 ]
Kanehara S, Ohtani T, Uede K, Furukawa F: Clinical effects of undershirts coated with borage oil on children with atopic dermatitis: a double-blind, placebo-controlled clinical trial. J Dermatol. 2007 Dec;34(12):811-5. doi: 10.1111/j.1346-8138.2007.00391.x. [PubMed:18078406 ]

Showing NP-Card for Gamma-linolenic acid (NP0044240)

MOL for NP0044240 (Gamma-linolenic acid)

3D MOL for NP0044240 (Gamma-linolenic acid)

3D SDF for NP0044240 (Gamma-linolenic acid)

3D-SDF for NP0044240 (Gamma-linolenic acid)

PDB for NP0044240 (Gamma-linolenic acid)

3D PDB for NP0044240 (Gamma-linolenic acid)

SMILES for NP0044240 (Gamma-linolenic acid)

INCHI for NP0044240 (Gamma-linolenic acid)

Structure for NP0044240 (Gamma-linolenic acid)

3D Structure for NP0044240 (Gamma-linolenic acid)