gamolenic acid (Q415885)

gamma-Linolenic acid (English)

3 October 2016

chemical formula

C₁₈H₃₀O₂

1 reference

gamma-Linolenic acid (English)

19 November 2016

canonical SMILES

CCCCCC=CCC=CCC=CCCCCC(=O)O

1 reference

gamma-Linolenic acid (English)

19 November 2016

isomeric SMILES

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

1 reference

gamma-Linolenic acid (English)

19 November 2016

1 reference

Anemone ranunculoides

1 reference

Anemone narcissiflora

1 reference

Anemone cylindrica

1 reference

Anemone altaica

1 reference

Oenothera biennis

11 references

Gamma linolenic acid (GLA) content of encapsulated evening primrose oil products

γ-Linolenic acid concentrates from borage and evening primrose oil fatty acidsvia lipase-catalyzed esterification

Enrichment of γ-linolenic acid from evening primrose oil and borage oilvia lipase-catalyzed hydrolysis

Supercritical carbon dioxide extraction of evening primrose oil

Comparative study of diets enriched with evening primrose, black currant, borage or fungal oils on blood pressure and pressor responses in spontaneously hypertensive rats

Formation of .gamma.-linolenic acid in the higher plant evening primrose (Oenothera biennis L.)

Ribes nigrum

1 reference

Comparative study of diets enriched with evening primrose, black currant, borage or fungal oils on blood pressure and pressor responses in spontaneously hypertensive rats

borage

12 references

γ-Linolenic acid concentrates from borage and evening primrose oil fatty acidsvia lipase-catalyzed esterification

Enrichment of γ-linolenic acid from evening primrose oil and borage oilvia lipase-catalyzed hydrolysis

Comparative study of diets enriched with evening primrose, black currant, borage or fungal oils on blood pressure and pressor responses in spontaneously hypertensive rats

In vivo and in vitro lipid accumulation inBorago officinalis L.

Stearidonic and γ-linolenic acid contents of common borage leaves

Biosynthesis of gamma-linolenic acid in developing seeds of borage (Borago officinalis L.).

Dietary borage oil alters plasma, hepatic and vascular tissue fatty acid composition in spontaneously hypertensive rats

First Field Trials of Borage (Borago officinalisL.) in Andalusia (Southern Spain) as a Source of “Biological” Gamma Linolenic Acid

Variability in the Content of Gamma-Linolenic Acid and Other Fatty Acids of the Seed Oil of Germplasm of Wild and Cultivated Borage (Borago officinalis L.)

Mucor javanicus

1 reference

Comparative study of diets enriched with evening primrose, black currant, borage or fungal oils on blood pressure and pressor responses in spontaneously hypertensive rats

Mucor circinelloides

1 reference

Comparative study of diets enriched with evening primrose, black currant, borage or fungal oils on blood pressure and pressor responses in spontaneously hypertensive rats

Hippophae rhamnoides

1 reference

Fatty acid composition of lipids in sea buckthorn (Hippophaë rhamnoides L.) berries of different origins.

Oenothera argillicola

1 reference

Oenothera clavaeformis

1 reference

Oenothera drummondii

1 reference

Oenothera elata

1 reference

Oenothera grandiflora

1 reference

Oenothera laciniata

1 reference

Oenothera lamarckiana

1 reference

Oenothera glazioviana

1 reference

Oenothera odorata

1 reference

Oenothera parviflora

1 reference

Oenothera rhombipetala

1 reference

Oenothera rosea

1 reference

Oenothera serrulata

1 reference

Oenothera striata

1 reference

Alkanna froedinii

1 reference

Alkanna orientalis

1 reference

Amsinckia lunaris

1 reference

Anchusa strigosa

1 reference

Brunnera orientalis

1 reference

Johnstonella grayi

1 reference

Echium glomeratum

1 reference

Hackelia floribunda

1 reference

Nonea macrosperma

1 reference

Pectocarya platycarpa

1 reference

Trichodesma zeylanicum

1 reference

Scrophularia canina

1 reference

Scrophularia grayana

1 reference

Scrophularia koraiensis

1 reference

Scrophularia kakudensis

1 reference

Scrophularia lanceolata

1 reference

Scrophularia marilandica

1 reference

Scrophularia rubricaulis

1 reference

Ribes alpinum

1 reference

Ribes orientale

1 reference

Ribes montigenum

1 reference

Mortierella hygrophila

2 references

Production of arachidonic acid by Mortierella fungi

Production of eicosapentaenoic acid by Mortierella fungi

Mortierella hyalina

2 references

Production of arachidonic acid by Mortierella fungi

Production of eicosapentaenoic acid by Mortierella fungi

Mortierella zychae

2 references

Production of arachidonic acid by Mortierella fungi

Production of eicosapentaenoic acid by Mortierella fungi

Mortierella elongata

2 references

Production of arachidonic acid by Mortierella fungi

Production of eicosapentaenoic acid by Mortierella fungi

Mortierella parvispora

2 references

Production of arachidonic acid by Mortierella fungi

Production of eicosapentaenoic acid by Mortierella fungi

Mortierella alpina

4 references

Production of a novel ω1-eicosapentaenoic acid by Mortierella alpina 1S-4 grown on 1-hexadecene

Production of arachidonic acid by Mortierella fungi

Production of dihomo-γ-linolenic acid byMortierella alpina 1S-4

Production of eicosapentaenoic acid by Mortierella fungi

Marchantia polymorpha

1 reference

Production of arachidonic acid and eicosapentaenoic acids by Marchantia polymorpha in cell culture

Bartramia pomiformis

1 reference

Production of arachidonic acid and eicosapentaenoic acids by Marchantia polymorpha in cell culture

Brachythecium buchananii

1 reference

Production of arachidonic acid and eicosapentaenoic acids by Marchantia polymorpha in cell culture

Brotherella henonii

1 reference

Production of arachidonic acid and eicosapentaenoic acids by Marchantia polymorpha in cell culture

Campylopus richardii

1 reference

Production of arachidonic acid and eicosapentaenoic acids by Marchantia polymorpha in cell culture

Cratoneuron filicinum

1 reference

Production of arachidonic acid and eicosapentaenoic acids by Marchantia polymorpha in cell culture

Ctenidium percrassum

1 reference

Production of arachidonic acid and eicosapentaenoic acids by Marchantia polymorpha in cell culture

Dicranum japonicum

1 reference

Production of arachidonic acid and eicosapentaenoic acids by Marchantia polymorpha in cell culture

Dolichomitra cymbifolia

1 reference

Production of arachidonic acid and eicosapentaenoic acids by Marchantia polymorpha in cell culture

Grimmia pilifera

1 reference

Production of arachidonic acid and eicosapentaenoic acids by Marchantia polymorpha in cell culture

Fissidens nobilis

1 reference

Production of arachidonic acid and eicosapentaenoic acids by Marchantia polymorpha in cell culture

Hedwigia ciliata

1 reference

Production of arachidonic acid and eicosapentaenoic acids by Marchantia polymorpha in cell culture

Loeskeobryum brevirostre

1 reference

Production of arachidonic acid and eicosapentaenoic acids by Marchantia polymorpha in cell culture

Hypnum fujiyamae

1 reference

Production of arachidonic acid and eicosapentaenoic acids by Marchantia polymorpha in cell culture

Leucobryum neilgherrense

1 reference

Production of arachidonic acid and eicosapentaenoic acids by Marchantia polymorpha in cell culture

Myuroclada maximowiczii

1 reference

Production of arachidonic acid and eicosapentaenoic acids by Marchantia polymorpha in cell culture

Oncophorus crispifolius

1 reference

Production of arachidonic acid and eicosapentaenoic acids by Marchantia polymorpha in cell culture

Plagiomnium maximoviczii

1 reference

Production of arachidonic acid and eicosapentaenoic acids by Marchantia polymorpha in cell culture

Plagiothecium euryphyllum

1 reference

Production of arachidonic acid and eicosapentaenoic acids by Marchantia polymorpha in cell culture

Pogonatum inflexum

1 reference

Production of arachidonic acid and eicosapentaenoic acids by Marchantia polymorpha in cell culture

Pyrrhobryum spiniforme

1 reference

Production of arachidonic acid and eicosapentaenoic acids by Marchantia polymorpha in cell culture

Rhizomnium tuomikoskii

1 reference

Production of arachidonic acid and eicosapentaenoic acids by Marchantia polymorpha in cell culture

Scopelophila cataractae

1 reference

Production of arachidonic acid and eicosapentaenoic acids by Marchantia polymorpha in cell culture

Sphagnum palustre

1 reference

Production of arachidonic acid and eicosapentaenoic acids by Marchantia polymorpha in cell culture

Thamnobryum plicatulum

1 reference

Production of arachidonic acid and eicosapentaenoic acids by Marchantia polymorpha in cell culture

Thuidium glaucinum

1 reference

Production of arachidonic acid and eicosapentaenoic acids by Marchantia polymorpha in cell culture

Thuidium pristocalyx

1 reference

Production of arachidonic acid and eicosapentaenoic acids by Marchantia polymorpha in cell culture

Thuidium recognitum

1 reference

Production of arachidonic acid and eicosapentaenoic acids by Marchantia polymorpha in cell culture

Thuidium tamariscinum

1 reference

Production of arachidonic acid and eicosapentaenoic acids by Marchantia polymorpha in cell culture

Ulota crispa

1 reference

Production of arachidonic acid and eicosapentaenoic acids by Marchantia polymorpha in cell culture

Vesicularia ferriei

1 reference

Production of arachidonic acid and eicosapentaenoic acids by Marchantia polymorpha in cell culture

Wijkia concavifolia

1 reference

Production of arachidonic acid and eicosapentaenoic acids by Marchantia polymorpha in cell culture

Oenothera missouriensis

1 reference

Oenothera strigosa

1 reference

Ribes cereum var. cereum

1 reference

Abies pinsapo subsp. marocana

1 reference

Terpenoids of the wood of Abies marocana

Brassica rapa

1 reference

Analysis of low erucic acid turnip rapeseed oil (Brassica campestris) by negative ion chemical ionization tandem mass spectrometry. A method giving information on the fatty acid composition in positionssn-2 andsn-1/3 of triacylglycerols

Brassica campestris

1 reference

Analysis of low erucic acid turnip rapeseed oil (Brassica campestris) by negative ion chemical ionization tandem mass spectrometry. A method giving information on the fatty acid composition in positionssn-2 andsn-1/3 of triacylglycerols

Crepidiastrum akagii

1 reference

Occurrence of gamma-linolenic acid in compositae: a study of Youngia tenuicaulis seed oil

Malva sylvestris

1 reference

Some components of the seed oil ofMalva sylvestris

sesame

1 reference

Dietary borage oil alters plasma, hepatic and vascular tissue fatty acid composition in spontaneously hypertensive rats

Agaricus blazei

1 reference

[Antimutagenic and bactericidal substances in the fruit body of a Basidiomycete Agaricus blazei, Jun-17]

Echium auberianum

1 reference

Substrate specificity of acyl-Delta(6)-desaturases from Continental versus Macaronesian Echium species.

Echium gentianoides

1 reference

Substrate specificity of acyl-Delta(6)-desaturases from Continental versus Macaronesian Echium species.

Echium giganteum

1 reference

Substrate specificity of acyl-Delta(6)-desaturases from Continental versus Macaronesian Echium species.

Echium lusitanicum

1 reference

Substrate specificity of acyl-Delta(6)-desaturases from Continental versus Macaronesian Echium species.

Echium lancerottense

1 reference

Substrate specificity of acyl-Delta(6)-desaturases from Continental versus Macaronesian Echium species.

Echium pitardii

1 reference

Substrate specificity of acyl-Delta(6)-desaturases from Continental versus Macaronesian Echium species.

Echium plantagineum

2 references

Substrate specificity of acyl-Delta(6)-desaturases from Continental versus Macaronesian Echium species.

The occurrence of 6,9,12,15-octadecatetraenoic acid inEchium plantagineumseed oil

Echium sabulicola

1 reference

Substrate specificity of acyl-Delta(6)-desaturases from Continental versus Macaronesian Echium species.

Echium strictum

1 reference

Substrate specificity of acyl-Delta(6)-desaturases from Continental versus Macaronesian Echium species.

Echium vulgare

1 reference

Substrate specificity of acyl-Delta(6)-desaturases from Continental versus Macaronesian Echium species.

Lithothamnion corallioides

1 reference

Metabolism of 6,9,12-octadecatrienoic acid in the red alga Lithothamnion corallioides: mechanism of formation of a conjugated tetraene fatty acid

Cunninghamella echinulata

1 reference

γ-linolenic acid production by Cunninghamella japonica in solid state fermentation

Phycomyces blakesleeanus

1 reference

Acidic metabolites from Phycomyces blakesleeanus

Punica granatum

2 references

Pomegranate (Punica granatum) seed linolenic acid isomers: concentration-dependent modulation of estrogen receptor activity

Diverse Phytochemicals and Bioactivities in the Ancient Fruit and Modern Functional Food Pomegranate (Punica granatum).

Eurhynchium striatum

1 reference

Effects of culture conditions on accumulation of arachidonic and eicosapentaenoic acids in cultured cells of Rhytidiadelphus squarrosus and Eurhynchium striatum

Rhytidiadelphus squarrosus

1 reference

Effects of culture conditions on accumulation of arachidonic and eicosapentaenoic acids in cultured cells of Rhytidiadelphus squarrosus and Eurhynchium striatum

Homo sapiens

2 references

Recon 2.2: from reconstruction to model of human metabolism

A community-driven global reconstruction of human metabolism.

Oenothera depressa

1 reference

Cunninghamella japonica

1 reference

γ-linolenic acid production by Cunninghamella japonica in solid state fermentation

Echium thyrsiflorum

1 reference

Substrate specificity of acyl-Delta(6)-desaturases from Continental versus Macaronesian Echium species.

Anemonastrum crinitum

1 reference

Oenothera tetragona

1 reference

Oenothera stricta

1 reference

Prostaglandin F2alpha and gamma-Linolenic Acid in Oenothera stricta

Amsinckia menziesii var. intermedia

1 reference

Oenothera erythrosepala

1 reference

Anemone multifida

1 reference

Gracilaria verrucosa

1 reference

Component Fatty Acid of Lipid from Gracilaria verrucosa

Caenorhabditis elegans

1 reference

Modeling Meets Metabolomics-The WormJam Consensus Model as Basis for Metabolic Studies in the Model Organism

Gracilaria longissima

1 reference

Component Fatty Acid of Lipid from Gracilaria verrucosa

Eulobus californicus

1 reference

Schlotheimia grevilleana

1 reference

Production of arachidonic acid and eicosapentaenoic acids by Marchantia polymorpha in cell culture

subject has role

5-alpha-reductase inhibitors

0 references

Commons category

Gamma-Linolenic acid

0 references

Identifiers

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-

1 reference

gamma-Linolenic acid (English)

19 November 2016

2 references

gamma-Linolenic acid (English)

19 November 2016

ChEBI release 2020-09-01

CAS Registry Number

506-26-3

2 references

Global Substance Registration System

gamolenic acid (English)

19 November 2016

https://commonchemistry.cas.org/detail?cas_rn=506-26-3

8 April 2021

1 reference

Gamma-Linolenic acid (English)

19 November 2016

1 reference

gamma-Linolenic acid (English)

19 November 2016

Reaxys registry number

1712253

1 reference

gamma-linolenic acid (English)

3 October 2016

ChEBI ID

28661

mapping relation type

2 references

GAMOLENIC ACID (English)

matched by identifier from

19 November 2016

International Chemical Identifier

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-

1 reference

matched by identifier from

GAMOLENIC ACID (English)

19 November 2016

2 references

inferred from InChIKey

MSBNK-BGC_Munich-RP014301

1 reference

MassBank accession ID

0 references

0 references

0 references

0 references

0 references

0 references

MSBNK-BGC_Munich-RP014302

0 references

MSBNK-BGC_Munich-RP014303

0 references

MSBNK-BGC_Munich-RP014311

0 references

MSBNK-BGC_Munich-RP014312

0 references

MSBNK-RIKEN-PR010203

0 references

MSBNK-RIKEN-PR100632

0 references

SPLASH

splash10-004i-0090000000-dcae4273443fd52bbb03

0 references

splash10-004i-0090000000-143e6ddfa05656a4c4da

0 references

splash10-004i-0090000000-0b9ba563ad074fe141e8

0 references

splash10-004i-0090000000-63bf7d731625d5577978

0 references

splash10-004i-0090000000-fbc4e202a8b26c91dc9e

0 references

splash10-004i-0090000000-b56d00321ab0921fe7b7

0 references

splash10-00nf-9200000000-cf911df79059a750cb2a

0 references

splash10-005l-0902100000-6fc8730bd28daa779b66

0 references

splash10-005c-9800000000-7b6e7a36b048f5ed69bd

0 references

DSSTox substance ID

DTXSID7046170

1 reference

Mapping file of InChIStrings, InChIKeys and DTXSIDs for the EPA CompTox Dashboard

DSSTOX compound identifier

DTXCID5026170

0 references

EC number

624-740-4

1 reference

ECHA Substance Infocard database

ECHA Substance Infocard ID

100.107.263

27 December 2018

ECHA Substance Infocard ID

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

quotation

CAS no.: 506-26-3 (English)

100.107.263

1 reference

ECHA Substance Infocard database

ECHA Substance Infocard ID

100.107.263

27 December 2018

AICS Chemical ID (BEING DELETED)

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

quotation

CAS no.: 506-26-3 (English)

1 reference

4569

0 references

ATC code

D11AX02

0 references

Guide to Pharmacology Ligand ID

4710

1 reference

IUPHAR/BPS Guide to PHARMACOLOGY

Guide to Pharmacology Ligand ID

4710

Global Substance Registration System

γ-linolenic acid (English)

19 November 2016

gamma-Linolenic Acid

0 references

MeSH tree code

D10.251.355.310.640.425

0 references

0 references

1 reference

gamolenic acid (English)

19 November 2016

1 reference

Human Metabolome Database ID

Gamolenic acid (English)

publication date

3 July 2018

HMDB0003073

2 references

based on heuristic

inferred from InChIKey

matched by identifier from

2 references

gamma-linolenic acid (English)

3 October 2016

based on heuristic

inferred from InChIKey

1 reference

Global Substance Registration System

gamolenic acid (English)

19 November 2016

0 references

1 reference

1 reference

gamma-linolenic acid (English)

3 October 2016

C06426

1 reference