gamma-Linolenic acid (GLA; cis-18:3n-6) (Compound)

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ID	433
Name	gamma-Linolenic acid (GLA; cis-18:3n-6)
Synonyms	all-cis-6,9,12-Octadecatrienoic acid
Structure	MOL SDF PDB SMILES InChI Structure for EE000433 (gamma-Linolenic acid (GLA; cis-18:3n-6)) 3D Structure for EE000433 (gamma-Linolenic acid (GLA; cis-18:3n-6)) 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> EE000433 > <DATABASE_NAME> ExposomeExplorer > <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 $$$$
Description
Classification	Compounds > Chemical entities > Organic compounds > Lipids and lipid-like molecules > Fatty Acyls > Lineolic acids and derivatives
CAS number	506-26-3
PubChem ID	5280933
ChEBI ID	28661
FooDB ID	FDB002943
HMDB ID	HMDB0003073

Chemical data

MolDBi data

IUPAC Name	(6Z,9Z,12Z)-octadeca-6,9,12-trienoic acid
Traditional IUPAC Name	gamma linolenic acid
Formula	C18H30O2
InChI	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
Molecular weight	278.4296
Exact mass	278.224580204
SMILES	CCCCC\C=C/C\C=C/C\C=C/CCCCC(O)=O

ClassyFire 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	Long-chain fatty acids Unsaturated fatty acids Straight chain fatty acids Monocarboxylic acids and derivatives Carboxylic acids Organic oxides Hydrocarbon derivatives Carbonyl compounds

Publications with gamma-Linolenic acid (GLA; cis-18:3n-6)

ID	Title	First author	Authors	Year	Journal	Volume	Issue	Pages	PubMed ID	DOI	Study design	No. of Biomarkers	No. of Intake values	No. of Concentration values	No. of Reproducibility values	No. of Correlation values	No. of Metabolomic associations	No. of Microbiota associations	No. of Cancer associations

Biomarker data

Measurements of gamma-Linolenic acid (GLA; cis-18:3n-6) in biospecimens

Concentration values

ID	Parent ID	Depth	Subject group	Population	Country	Cohort	Biomarker Time definition	Biospecimen	Analytical method	Biomarker	Biomarker detail	Measurement size	Detected (nb)	Detected (%)	Detected only?	Arithmethic mean	Arithmethic SD	Geometric mean	Geometric SD	Min	Min (detected)	Percentile_05	Percentile_10	Percentile_25	Median	Percentile_75	Percentile_90	Percentile_95	Max	Interquartile range	Mean 95% CI lower	Mean 95% CI upper	GMean 95% CI lower	GMean 95% CI upper	Unit	Converted arithmetic mean	Converted geometric mean	Converted median	Converted unit	Adjustment type	Adjusted on	Regressed on	Expressed as	Publication

Reproducibility values

ID	Excretion ID	Subject group	Population	Country	Cohort	Biomarker Time definition	Biospecimen	Analytical method	Biomarker	Biomarker detail	Arithmetic mean	Geometric mean	Median	Unit	Adjusted on	Reproducibility size	ICC	ICC 95% CI lower	ICC 95% CI upper	CV% WS	CV% BS	VAR WS	VAR BS	Publication

Associations of gamma-Linolenic acid (GLA; cis-18:3n-6) with exposures

Correlation values

ID	Intake ID	Excretion ID	Subject group	Population	Country	Cohort	Intake Time definition	Intake Assessment method	Intake	Intake detail	Supplement intakes included?	Intake Arithmetic mean	Intake Geometric mean	Intake Median	Intake Unit	Intake Adjusted on	Biomarker Time definition	Biospecimen	Analytical method	Biomarker	Biomarker detail	Biomarker Arithmetic mean	Biomarker Geometric mean	Biomarker Median	Biomarker Unit	Biomarker Adjusted on	Correlation size	Correlation type	Correlation value	Correlation 95% CI lower	Correlation 95% CI upper	Correlation p-value	Significant?	Measurement adjustment	Deattenuated?	Covariates	Publication

Metabolomic associations

ID	Intake ID	Excretion ID	Subject group	Population	Country	Cohort	No. of subjects	Intake Assessment method	Intake	Intervention dose	Biospecimen	Analytical method	Biomarker	Structural identification	Feature selection	Area under curve	Sensitivity	Specificity	PLS-DA VIP	Beta coefficient	Beta coefficient p-value	ANOVA p-value	Publication

Microbiota associations

ID	Biomarker	Experimental evidence	Organism	Biospecimen	Antibiotic	Bacterial source	Substrate	Publication

Associations of gamma-Linolenic acid (GLA; cis-18:3n-6) with cancer risk

Cancer associations

ID	Excretion ID	Subject group	Population	Country	Cohort	No. of subjects	No. of cases	No. of controls	Biospecimen	Analytical method	Biomarker	Biomarker detail	Cancer	Study design	Publication

Exposure data

Measurements of gamma-Linolenic acid (GLA; cis-18:3n-6) exposures in populations

Intake values

ID	Parent ID	Depth	Subject group	Population	Country	Cohort	Intake Time definition	Intake assessment tool	Intake food coverage	Intake time coverage	Intake Assessment method	Intake	Intake detail	Food description	Supplement intakes included?	Measurement size	Detected (nb)	Detected (%)	Detected only?	Arithmethic mean	Arithmethic SD	Geometric mean	Geometric SD	Min	Min (detected)	Percentile_05	Percentile_10	Percentile_25	Median	Percentile_75	Percentile_90	Percentile_95	Max	Interquartile range	Mean 95% CI lower	Mean 95% CI upper	GMean 95% CI lower	GMean 95% CI upper	Unit	Converted arithmetic mean	Converted geometric mean	Converted median	Converted unit	Adjustment type	Adjusted on	Regressed on	Expressed as	Publication

Associations of gamma-Linolenic acid (GLA; cis-18:3n-6) exposures with biomarkers

Correlation values

ID	Intake ID	Excretion ID	Subject group	Population	Country	Cohort	Intake Time definition	Intake Assessment method	Intake	Intake detail	Supplement intakes included?	Intake Arithmetic mean	Intake Geometric mean	Intake Median	Intake Unit	Intake Adjusted on	Biomarker Time definition	Biospecimen	Analytical method	Biomarker	Biomarker detail	Biomarker Arithmetic mean	Biomarker Geometric mean	Biomarker Median	Biomarker Unit	Biomarker Adjusted on	Correlation size	Correlation type	Correlation value	Correlation 95% CI lower	Correlation 95% CI upper	Correlation p-value	Significant?	Measurement adjustment	Deattenuated?	Covariates	Publication