CHEBI ONTOLOGY - ANNOTATIONS
The Chemical Entities of Biological Interest (ChEBI) ontology is downloaded weekly from EMBL-EBI at http://www.ebi.ac.uk/chebi/ . The data is made available under the Creative Commons License (CC BY 3.0, http://creativecommons.org/licenses/by/3.0/ ). For more information see: Degtyarenko et al. (2008) ChEBI: a database and ontology for chemical entities of biological interest. Nucleic Acids Res. 36, D344–D350.
Term: gamma-linolenic acid
Accession: CHEBI:28661
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Definition: A C18, omega-6 acid fatty acid comprising a linolenic acid having cis- double bonds at positions 6, 9 and 12.
Synonyms: exact_synonym: (6Z,9Z,12Z)-octadeca-6,9,12-trienoic acid
related_synonym: (6,9,12)-linolenic acid; (Z,Z,Z)-6,9,12-octadecatrienoic acid; 18:3 (n-6); 6,9,12-Octadecatrienoic acid; 6-cis,9-cis,12-cis-octadecatrienoic acid; 6Z,9Z,12Z-Octadecatrienoic acid; C18:3 (n-6); C18:3, n-6,9,12 all-cis; Formula=C18H30O2; GLA; 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-; InChIKey=VZCCETWTMQHEPK-QNEBEIHSSA-N; Octadeca-6,9,12-triensaeure; SMILES=CCCCC\\C=C/C\\C=C/C\\C=C/CCCCC(O)=O; all-cis-6,9,12-octadecatrienoic acid; cis-Delta(6,9,12)-octadecatrienoic acid; gamma-Linolensaeure; gamoleic acid; gamolenic acid
alt_id: CHEBI:10573; CHEBI:24197
xref: Beilstein:1712253; CAS:506-26-3; Drug_Central:1276; HMDB:HMDB0003073; KEGG:C06426; KEGG:D07213; KNApSAcK:C00001226; LIPID_MAPS_instance:LMFA01030141
xref_mesh: MESH:D017965
xref: MetaCyc:CPD-8117; PMID:11385052; PMID:24435467; PMID:9732298; Reaxys:1712253; Wikipedia:Gamma-Linolenic_acid
cyclic_relationship: is_conjugate_acid_of CHEBI:32391
G
Akr1c1
aldo-keto reductase family 1, member C1
increases expression
ISO
gamma-Linolenic Acid results in increased expression of AKR1C1 mRNA
CTD
PMID:20664735
NCBI chr17:65,810,474...65,837,385
Ensembl chr17:65,810,475...65,837,326
G
Apoh
apolipoprotein H
decreases expression
ISO
gamma-Linolenic Acid results in decreased expression of APOH mRNA
CTD
PMID:20664735
NCBI chr10:93,342,435...93,356,334
Ensembl chr10:93,310,977...93,356,329
G
Ar
androgen receptor
multiple interactions
ISO
gamma-Linolenic Acid inhibits the reaction [Metribolone results in increased activity of AR protein]
CTD
PMID:18324785
NCBI chr X:63,104,771...63,273,934
Ensembl chr X:63,104,771...63,273,925
G
Asah1
N-acylsphingosine amidohydrolase 1
increases expression
ISO
gamma-Linolenic Acid results in increased expression of ASAH1 mRNA
CTD
PMID:20664735
NCBI chr16:50,966,404...50,997,827
Ensembl chr16:50,966,229...51,008,233
G
Casp3
caspase 3
increases activity
ISO
gamma-Linolenic Acid results in increased activity of CASP3 protein
CTD
PMID:16857180
NCBI chr16:45,662,910...45,681,171
Ensembl chr16:45,662,910...45,684,648
G
Ccna2
cyclin A2
decreases expression
ISO
gamma-Linolenic Acid results in decreased expression of CCNA2 protein
CTD
PMID:15318936
NCBI chr 2:119,427,239...119,433,645
Ensembl chr 2:119,426,089...119,433,577
G
Ccne1
cyclin E1
decreases expression
ISO
gamma-Linolenic Acid results in decreased expression of CCNE1 protein
CTD
PMID:15318936
NCBI chr 1:90,781,947...90,791,188
Ensembl chr 1:90,781,949...90,791,101
G
Cdk1
cyclin-dependent kinase 1
decreases expression
ISO
gamma-Linolenic Acid results in decreased expression of CDK1 protein
CTD
PMID:15318936
NCBI chr20:19,266,226...19,281,417
Ensembl chr20:19,266,248...19,281,408
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Cldn5
claudin 5
multiple interactions
ISO
[gamma-Linolenic Acid co-treated with Iodine co-treated with Selenium] results in increased expression of and results in increased localization of CLDN5 protein; [gamma-Linolenic Acid co-treated with Iodine] results in increased expression of and results in increased localization of CLDN5 protein; [Selenium co-treated with gamma-Linolenic Acid] results in increased expression of and results in increased localization of CLDN5 protein; gamma-Linolenic Acid results in increased expression of and results in increased localization of CLDN5 protein
CTD
PMID:16514648
NCBI chr11:82,212,822...82,214,248
Ensembl chr11:82,211,475...82,214,992
G
Clta
clathrin, light chain A
increases expression
ISO
gamma-Linolenic Acid results in increased expression of CLTA mRNA
CTD
PMID:20664735
NCBI chr 5:58,244,253...58,263,480
Ensembl chr 5:58,245,442...58,263,472
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Fth1
ferritin heavy chain 1
increases expression
ISO
gamma-Linolenic Acid results in increased expression of FTH1 mRNA
CTD
PMID:20664735
NCBI chr 1:206,627,142...206,629,430
Ensembl chr 1:206,627,103...206,725,424
G
Gclc
glutamate-cysteine ligase, catalytic subunit
increases activity increases expression
ISO
gamma-Linolenic Acid results in increased activity of GCLC protein gamma-Linolenic Acid results in increased expression of GCLC mRNA
CTD
PMID:17092368
NCBI chr 8:78,629,899...78,668,547
Ensembl chr 8:78,630,127...78,668,544
G
Grk5
G protein-coupled receptor kinase 5
increases expression
ISO
gamma-Linolenic Acid results in increased expression of GRK5 mRNA
CTD
PMID:20664735
NCBI chr 1:260,028,269...260,223,699
Ensembl chr 1:260,028,242...260,218,701
G
Hexb
hexosaminidase subunit beta
increases expression
ISO
gamma-Linolenic Acid results in increased expression of HEXB mRNA
CTD
PMID:20664735
NCBI chr 2:28,483,997...28,504,165
Ensembl chr 2:28,484,012...28,504,223
G
Hist1h2al1
histone cluster 1 H2A family like 1
decreases expression
ISO
gamma-Linolenic Acid results in decreased expression of H2AC6 mRNA
CTD
PMID:20664735
NCBI chr17:42,707,954...42,708,420
G
Hmox1
heme oxygenase 1
increases expression
ISO
gamma-Linolenic Acid results in increased expression of HMOX1 mRNA; gamma-Linolenic Acid results in increased expression of HMOX1 protein
CTD
PMID:17092368 PMID:20664735
NCBI chr19:13,466,287...13,474,082
Ensembl chr19:13,467,244...13,474,079
G
Il2
interleukin 2
affects expression
ISO
gamma-Linolenic Acid affects the expression of IL2 protein
CTD
PMID:9415022
NCBI chr 2:120,004,862...120,009,566
Ensembl chr 2:120,004,862...120,009,566
G
Junb
JunB proto-oncogene, AP-1 transcription factor subunit
decreases expression
ISO
gamma-Linolenic Acid results in decreased expression of JUNB protein
CTD
PMID:15318936
NCBI chr19:23,176,265...23,178,049
Ensembl chr19:23,176,294...23,178,035
G
Kynu
kynureninase
decreases expression
ISO
gamma-Linolenic Acid results in decreased expression of KYNU mRNA
CTD
PMID:20664735
NCBI chr 3:27,778,646...27,929,470
Ensembl chr 3:27,778,772...27,929,488
G
Mapk3
mitogen activated protein kinase 3
decreases expression
ISO
gamma-Linolenic Acid results in decreased expression of MAPK3 protein
CTD
PMID:15318936
NCBI chr 1:181,366,646...181,372,863
Ensembl chr 1:181,366,637...181,372,863
G
Mmp11
matrix metallopeptidase 11
decreases expression
ISO
gamma-Linolenic Acid results in decreased expression of MMP11 mRNA
CTD
PMID:20664735
NCBI chr20:12,730,846...12,739,629
Ensembl chr20:12,730,836...12,739,628
G
Myc
MYC proto-oncogene, bHLH transcription factor
decreases expression
ISO
gamma-Linolenic Acid results in decreased expression of MYC protein
CTD
PMID:15318936
NCBI chr 7:93,593,705...93,598,633
Ensembl chr 7:93,593,705...93,598,630
G
Ocln
occludin
multiple interactions
ISO
[gamma-Linolenic Acid co-treated with Iodine co-treated with Selenium] results in increased expression of and results in increased localization of OCLN protein; [gamma-Linolenic Acid co-treated with Iodine] results in increased expression of and results in increased localization of OCLN protein; [Selenium co-treated with gamma-Linolenic Acid] results in increased expression of and results in increased localization of OCLN protein; gamma-Linolenic Acid results in increased expression of and results in increased localization of OCLN protein
CTD
PMID:16514648
NCBI chr 2:31,657,217...31,707,466
Ensembl chr 2:31,657,220...31,764,150
G
Parp1
poly (ADP-ribose) polymerase 1
increases cleavage
ISO
gamma-Linolenic Acid results in increased cleavage of PARP1 protein
CTD
PMID:10403056
NCBI chr13:92,307,593...92,339,406
Ensembl chr13:92,307,586...92,339,404
G
Pcna
proliferating cell nuclear antigen
decreases expression
ISO
gamma-Linolenic Acid results in decreased expression of PCNA mRNA
CTD
PMID:20664735
NCBI chr 3:119,499,039...119,502,911
Ensembl chr 3:119,498,810...119,502,995
G
Pdlim1
PDZ and LIM domain 1
decreases expression
ISO
gamma-Linolenic Acid results in decreased expression of PDLIM1 mRNA
CTD
PMID:20664735
NCBI chr 1:239,042,372...239,091,074
Ensembl chr 1:239,042,385...239,091,076
G
Plin2
perilipin 2
increases expression
ISO
gamma-Linolenic Acid results in increased expression of PLIN2 mRNA
CTD
PMID:20664735
NCBI chr 5:101,156,648...101,211,738
Ensembl chr 5:101,154,411...101,242,319
G
Ppara
peroxisome proliferator activated receptor alpha
multiple interactions
ISO
gamma-Linolenic Acid binds to and results in increased activity of PPARA protein
CTD
PMID:10403814
NCBI chr 7:116,832,405...116,900,878
Ensembl chr 7:116,832,756...116,895,346
G
Pparg
peroxisome proliferator-activated receptor gamma
multiple interactions
ISO
gamma-Linolenic Acid binds to and results in increased activity of PPARG protein
CTD
PMID:15318936
NCBI chr 4:148,423,102...148,548,471
Ensembl chr 4:148,423,194...148,548,468
G
Ptgr1
prostaglandin reductase 1
increases expression
ISO
gamma-Linolenic Acid results in increased expression of PTGR1 mRNA
CTD
PMID:20664735
NCBI chr 5:73,784,000...73,802,624
Ensembl chr 5:73,784,009...73,802,666
G
Ptgs2
prostaglandin-endoperoxide synthase 2
increases expression
ISO
gamma-Linolenic Acid results in increased expression of PTGS2 mRNA
CTD
PMID:17092368
NCBI chr13:62,163,936...62,172,193
Ensembl chr13:62,163,932...62,172,188
G
Skp2
S-phase kinase associated protein 2
decreases expression
ISO
gamma-Linolenic Acid results in decreased expression of SKP2 mRNA
CTD
PMID:20664735
NCBI chr 2:58,161,226...58,189,293
Ensembl chr 2:58,161,229...58,189,338
G
Slc3a2
solute carrier family 3 member 2
increases expression
ISO
gamma-Linolenic Acid results in increased expression of SLC3A2 mRNA
CTD
PMID:20664735
NCBI chr 1:205,604,468...205,618,931
Ensembl chr 1:205,604,468...205,618,931
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St13
ST13, Hsp70 interacting protein
increases expression
ISO
gamma-Linolenic Acid results in increased expression of ST13 mRNA
CTD
PMID:20664735
NCBI chr 7:112,891,007...112,925,727
Ensembl chr 7:112,844,375...112,925,945
G
Tff3
trefoil factor 3
decreases expression
ISO
gamma-Linolenic Acid results in decreased expression of TFF3 mRNA
CTD
PMID:20664735
NCBI chr20:9,193,259...9,197,969
Ensembl chr20:9,193,262...9,198,054
G
Tjp1
tight junction protein 1
multiple interactions
ISO
[gamma-Linolenic Acid co-treated with Iodine co-treated with Selenium] results in increased expression of and results in increased localization of TJP1 protein
CTD
PMID:16514648
NCBI chr 1:118,849,838...119,094,492
Ensembl chr 1:118,849,838...119,094,432
G
Tnf
tumor necrosis factor
decreases expression
ISO
gamma-Linolenic Acid results in decreased expression of TNF protein
CTD
PMID:9415022
NCBI chr20:3,622,011...3,624,629
Ensembl chr20:3,622,011...3,624,629
G
Trpv1
transient receptor potential cation channel, subfamily V, member 1
multiple interactions
EXP
gamma-Linolenic Acid inhibits the reaction [Capsaicin results in increased activity of TRPV1 protein]
CTD
PMID:17038422
NCBI chr10:57,851,428...57,876,513
Ensembl chr10:57,851,428...57,876,513
G
Txn1
thioredoxin 1
increases expression
ISO
gamma-Linolenic Acid results in increased expression of TXN mRNA
CTD
PMID:20664735
NCBI chr 5:72,712,334...72,724,564
Ensembl chr 5:72,711,933...72,724,629
G
Txnrd1
thioredoxin reductase 1
increases expression
ISO
gamma-Linolenic Acid results in increased expression of TXNRD1 mRNA
CTD
PMID:20664735
NCBI chr 7:20,830,042...20,914,990
Ensembl chr 7:20,830,045...20,907,863
Term paths to the root one shortest all shortest one longest all longest one shortest and longest all
Path 1
CHEBI ontology
19832
role
19808
biological role
19806
biochemical role
19517
metabolite
19504
eukaryotic metabolite
19321
plant metabolite
17962
gamma-linolenic acid
40
1-(gamma-linolenoyl)-2-oleoyl-sn-glycero-3-phosphate
0
1-(gamma-linolenoyl)-sn-glycero-3-phosphate
0
1-[(6Z,9Z,12Z)-octadecatrienoyl]-2-[(15Z)-tetracosenoyl]-sn-glycero-3-phosphocholine
0
1-[(6Z,9Z,12Z)-octadecatrienoyl]-2-[(9Z)-octadecenoyl]-snglycero-3-phosphocholine
0
1-[(9Z)-octadecenoyl]-2-[(6Z,9Z,12Z)-octadecatrienoyl]-sn-glycero-3-phosphocholine
0
1-hexadecyl-2-[(6Z,9Z,12Z)-octadecatrienoyl]-sn-glycero-3-phosphocholine
0
1-octadecanoyl-2-[(6Z,9Z,12Z)-octadecatrienoyl]-sn-glycero-3-phosphocholine
0
1-palmitoyl-2-[(6Z,9Z,12Z)-octadecatrienoyl]-sn-glycero-3-phosphocholine
0
1-tetracosyl-2-[(6Z,9Z,12Z)-octadecatrienoyl]-sn-glycero-3-phosphocholine
0
10(R)-HPO(6,8,12)TrE
0
10-HPO(6,8,12)TrE +
0
cholesteryl gamma-linolenate
0
gamma-linolenoyl bioconjugate +
0
gamma-linolenoyl group
0
gamma-linolenoyl-CoA
0
gamma-linolenoyl-containing glycerolipid +
0
methyl gamma-linolenate
0
Path 2
CHEBI ontology
19832
subatomic particle
19830
composite particle
19830
hadron
19830
baryon
19830
nucleon
19830
atomic nucleus
19830
atom
19830
main group element atom
19780
p-block element atom
19780
carbon group element atom
19729
carbon atom
19725
organic molecular entity
19725
heteroorganic entity
19479
organochalcogen compound
19242
organooxygen compound
19157
carbon oxoacid
18615
carboxylic acid
18612
monocarboxylic acid
17969
fatty acid
16687
unsaturated fatty acid
1096
polyunsaturated fatty acid
838
trienoic fatty acid
268
fatty acid 18:3
256
octadecatrienoic acid
256
linolenic acid
254
gamma-linolenic acid
40
1-(gamma-linolenoyl)-2-oleoyl-sn-glycero-3-phosphate
0
1-(gamma-linolenoyl)-sn-glycero-3-phosphate
0
1-[(6Z,9Z,12Z)-octadecatrienoyl]-2-[(15Z)-tetracosenoyl]-sn-glycero-3-phosphocholine
0
1-[(6Z,9Z,12Z)-octadecatrienoyl]-2-[(9Z)-octadecenoyl]-snglycero-3-phosphocholine
0
1-[(9Z)-octadecenoyl]-2-[(6Z,9Z,12Z)-octadecatrienoyl]-sn-glycero-3-phosphocholine
0
1-hexadecyl-2-[(6Z,9Z,12Z)-octadecatrienoyl]-sn-glycero-3-phosphocholine
0
1-octadecanoyl-2-[(6Z,9Z,12Z)-octadecatrienoyl]-sn-glycero-3-phosphocholine
0
1-palmitoyl-2-[(6Z,9Z,12Z)-octadecatrienoyl]-sn-glycero-3-phosphocholine
0
1-tetracosyl-2-[(6Z,9Z,12Z)-octadecatrienoyl]-sn-glycero-3-phosphocholine
0
10(R)-HPO(6,8,12)TrE
0
10-HPO(6,8,12)TrE +
0
cholesteryl gamma-linolenate
0
gamma-linolenoyl bioconjugate +
0
gamma-linolenoyl group
0
gamma-linolenoyl-CoA
0
gamma-linolenoyl-containing glycerolipid +
0
methyl gamma-linolenate
0