PCIDB

KNApSAcK Metabolite C00001226

Metabolite

KNApSAcK Entry

id C00001226
Name gamma-Linolenic acid / 6(Z),9(Z),12(Z)-Octadecatrienoic acid
CAS RN 506-26-3
Standard 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-
Standard InChI (Main Layer) 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)

Cluster

Phytochemical cluster No. 68
KCF-S cluster No. 300

Link

ChEMBL

By standard InChI CHEMBL464982
By standard InChI Main Layer CHEMBL464982

KEGG

By LinkDB C06426

CTD

By CAS RN D017965

Human Protein / Gene in interaction

17 ChEMBL Protein in interactions

accession description class description compound assay ID (# of activities) # of diseases
(OMIM / KEGG)
P49798 Regulator of G-protein signaling 4 Unclassified protein CHEMBL464982 CHEMBL1794499 (1)
2 / 0
Q13526 Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1 Enzyme CHEMBL464982 CHEMBL1794585 (1)
0 / 0
P49327 Fatty acid synthase Transferase CHEMBL464982 CHEMBL2169019 (1) CHEMBL2169020 (1)
0 / 0
P11473 Vitamin D3 receptor NR1I1 CHEMBL464982 CHEMBL1794311 (2)
2 / 3
Q92830 Histone acetyltransferase KAT2A Enzyme CHEMBL464982 CHEMBL1738606 (1)
0 / 0
P43220 Glucagon-like peptide 1 receptor Glucagon-like peptide receptor CHEMBL464982 CHEMBL2114788 (1)
0 / 0
Q9Y253 DNA polymerase eta Enzyme CHEMBL464982 CHEMBL1794569 (1)
1 / 1
Q9Y468 Lethal(3)malignant brain tumor-like protein 1 Unclassified protein CHEMBL464982 CHEMBL1614280 (1)
0 / 0
P83916 Chromobox protein homolog 1 Unclassified protein CHEMBL464982 CHEMBL1794401 (1)
0 / 0
O94782 Ubiquitin carboxyl-terminal hydrolase 1 Enzyme CHEMBL464982 CHEMBL1794467 (1)
0 / 0
P13726 Tissue factor Membrane receptor CHEMBL464982 CHEMBL995691 (1)
0 / 0
Q9UNA4 DNA polymerase iota Enzyme CHEMBL464982 CHEMBL1794483 (1)
0 / 0
Q9UBT6 DNA polymerase kappa Enzyme CHEMBL464982 CHEMBL1794536 (2)
0 / 0
Q96KQ7 Histone-lysine N-methyltransferase EHMT2 Enzyme CHEMBL464982 CHEMBL1738442 (1)
0 / 0
O75874 Isocitrate dehydrogenase [NADP] cytoplasmic Enzyme CHEMBL464982 CHEMBL1964002 (1)
1 / 0
O94925 Glutaminase kidney isoform, mitochondrial Enzyme CHEMBL464982 CHEMBL2114738 (2)
0 / 0
Q14191 Werner syndrome ATP-dependent helicase Enzyme CHEMBL464982 CHEMBL2114796 (1)
2 / 1

CTD interaction (50)

compound gene gene name gene description interaction interaction type form reference
pmid
D017965 1645 AKR1C1
2-ALPHA-HSD
20-ALPHA-HSD
C9
DD1
DD1/DD2
DDH
DDH1
H-37
HAKRC
HBAB
MBAB
aldo-keto reductase family 1, member C1 (EC:1.3.1.20 1.1.1.149 1.1.1.112) gamma-Linolenic Acid results in increased expression of AKR1C1 mRNA increases expression
mRNA 20664735
D017965 1109 AKR1C4
3-alpha-HSD
C11
CDR
CHDR
DD-4
DD4
HAKRA
aldo-keto reductase family 1, member C4 (EC:1.1.1.225 1.1.1.357) gamma-Linolenic Acid results in increased expression of AKR1C4 mRNA increases expression
mRNA 20664735
D017965 350 APOH
B2G1
B2GP1
BG
apolipoprotein H (beta-2-glycoprotein I) gamma-Linolenic Acid results in decreased expression of APOH mRNA decreases expression
mRNA 20664735
D017965 367 AR
AIS
DHTR
HUMARA
HYSP1
KD
NR3C4
SBMA
SMAX1
TFM
androgen receptor gamma-Linolenic Acid inhibits the reaction [Metribolone results in increased activity of AR protein] decreases reaction
/ increases activity
protein 18324785
D017965 427 ASAH1
AC
ACDase
ASAH
PHP
PHP32
SMAPME
N-acylsphingosine amidohydrolase (acid ceramidase) 1 (EC:3.5.1.23) gamma-Linolenic Acid results in increased expression of ASAH1 mRNA increases expression
mRNA 20664735
D017965 836 CASP3
CPP32
CPP32B
SCA-1
caspase 3, apoptosis-related cysteine peptidase (EC:3.4.22.56) gamma-Linolenic Acid results in increased activity of CASP3 protein increases activity
protein 16857180
D017965 890 CCNA2
CCN1
CCNA
cyclin A2 gamma-Linolenic Acid results in decreased expression of CCNA2 protein decreases expression
protein 15318936
D017965 898 CCNE1
CCNE
cyclin E1 gamma-Linolenic Acid results in decreased expression of CCNE1 protein decreases expression
protein 15318936
D017965 983 CDK1
CDC2
CDC28A
P34CDC2
cyclin-dependent kinase 1 (EC:2.7.11.23 2.7.11.22) gamma-Linolenic Acid results in decreased expression of CDK1 protein decreases expression
protein 15318936
D017965 7122 CLDN5
AWAL
BEC1
CPETRL1
TMVCF
claudin 5 [gamma-Linolenic Acid co-treated with Iodine co-treated with Selenium] results in increased expression of and results in increased localization of CLDN5 protein affects cotreatment
/ increases expression
/ increases localization
protein 16514648
D017965 7122 CLDN5
AWAL
BEC1
CPETRL1
TMVCF
claudin 5 [gamma-Linolenic Acid co-treated with Iodine] results in increased expression of and results in increased localization of CLDN5 protein affects cotreatment
/ increases expression
/ increases localization
protein 16514648
D017965 7122 CLDN5
AWAL
BEC1
CPETRL1
TMVCF
claudin 5 gamma-Linolenic Acid results in increased expression of and results in increased localization of CLDN5 protein increases expression
/ increases localization
protein 16514648
D017965 7122 CLDN5
AWAL
BEC1
CPETRL1
TMVCF
claudin 5 [Selenium co-treated with gamma-Linolenic Acid] results in increased expression of and results in increased localization of CLDN5 protein affects cotreatment
/ increases expression
/ increases localization
protein 16514648
D017965 1211 CLTA
LCA
clathrin, light chain A gamma-Linolenic Acid results in increased expression of CLTA mRNA increases expression
mRNA 20664735
D017965 2495 FTH1
FHC
FTH
FTHL6
PIG15
PLIF
ferritin, heavy polypeptide 1 (EC:1.16.3.1) gamma-Linolenic Acid results in increased expression of FTH1 mRNA increases expression
mRNA 20664735
D017965 2729 GCLC
GCL
GCS
GLCL
GLCLC
glutamate-cysteine ligase, catalytic subunit (EC:6.3.2.2) gamma-Linolenic Acid results in increased activity of GCLC protein increases activity
protein 17092368
D017965 2729 GCLC
GCL
GCS
GLCL
GLCLC
glutamate-cysteine ligase, catalytic subunit (EC:6.3.2.2) gamma-Linolenic Acid results in increased expression of GCLC mRNA increases expression
mRNA 17092368
D017965 2869 GRK5
GPRK5
G protein-coupled receptor kinase 5 (EC:2.7.11.16) gamma-Linolenic Acid results in increased expression of GRK5 mRNA increases expression
mRNA 20664735
D017965 3074 HEXB
ENC-1AS
hexosaminidase B (beta polypeptide) (EC:3.2.1.52) gamma-Linolenic Acid results in increased expression of HEXB mRNA increases expression
mRNA 20664735
D017965 8334 HIST1H2AC
H2A/l
H2AFL
dJ221C16.4
histone cluster 1, H2ac gamma-Linolenic Acid results in decreased expression of HIST1H2AC mRNA decreases expression
mRNA 20664735
D017965 3162 HMOX1
HMOX1D
HO-1
HSP32
bK286B10
heme oxygenase (decycling) 1 (EC:1.14.99.3) gamma-Linolenic Acid results in increased expression of HMOX1 mRNA increases expression
mRNA 17092368
20664735
D017965 3162 HMOX1
HMOX1D
HO-1
HSP32
bK286B10
heme oxygenase (decycling) 1 (EC:1.14.99.3) gamma-Linolenic Acid results in increased expression of HMOX1 protein increases expression
protein 20664735
D017965 3558 IL2
IL-2
TCGF
lymphokine
interleukin 2 gamma-Linolenic Acid affects the expression of IL2 protein affects expression
protein 9415022
D017965 3726 JUNB
AP-1
jun B proto-oncogene gamma-Linolenic Acid results in decreased expression of JUNB protein decreases expression
protein 15318936
D017965 8942 KYNU
kynureninase (EC:3.7.1.3) gamma-Linolenic Acid results in decreased expression of KYNU mRNA decreases expression
mRNA 20664735
D017965 5595 MAPK3
ERK-1
ERK1
ERT2
HS44KDAP
HUMKER1A
P44ERK1
P44MAPK
PRKM3
p44-ERK1
p44-MAPK
mitogen-activated protein kinase 3 (EC:2.7.11.24) gamma-Linolenic Acid results in decreased expression of MAPK3 protein decreases expression
protein 15318936
D017965 4320 MMP11
SL-3
ST3
STMY3
matrix metallopeptidase 11 (stromelysin 3) (EC:3.4.24.-) gamma-Linolenic Acid results in decreased expression of MMP11 mRNA decreases expression
mRNA 20664735
D017965 4495 MT1G
MT1
MT1K
metallothionein 1G gamma-Linolenic Acid results in increased expression of MT1G mRNA increases expression
mRNA 20664735
D017965 4500 MT1L
MT1
MT1R
MTF
metallothionein 1L (gene/pseudogene) gamma-Linolenic Acid results in increased expression of MT1L mRNA increases expression
mRNA 20664735
D017965 4609 MYC
MRTL
MYCC
bHLHe39
c-Myc
v-myc avian myelocytomatosis viral oncogene homolog gamma-Linolenic Acid results in decreased expression of MYC protein decreases expression
protein 15318936
D017965 100506658 OCLN
BLCPMG
occludin (EC:2.1.1.67) [gamma-Linolenic Acid co-treated with Iodine co-treated with Selenium] results in increased expression of and results in increased localization of OCLN protein affects cotreatment
/ increases expression
/ increases localization
protein 16514648
D017965 100506658 OCLN
BLCPMG
occludin (EC:2.1.1.67) [gamma-Linolenic Acid co-treated with Iodine] results in increased expression of and results in increased localization of OCLN protein affects cotreatment
/ increases expression
/ increases localization
protein 16514648
D017965 100506658 OCLN
BLCPMG
occludin (EC:2.1.1.67) gamma-Linolenic Acid results in increased expression of and results in increased localization of OCLN protein increases expression
/ increases localization
protein 16514648
D017965 100506658 OCLN
BLCPMG
occludin (EC:2.1.1.67) [Selenium co-treated with gamma-Linolenic Acid] results in increased expression of and results in increased localization of OCLN protein affects cotreatment
/ increases expression
/ increases localization
protein 16514648
D017965 5111 PCNA
proliferating cell nuclear antigen gamma-Linolenic Acid results in decreased expression of PCNA mRNA decreases expression
mRNA 20664735
D017965 9124 PDLIM1
CLIM1
CLP-36
CLP36
hCLIM1
PDZ and LIM domain 1 gamma-Linolenic Acid results in decreased expression of PDLIM1 mRNA decreases expression
mRNA 20664735
D017965 123 PLIN2
ADFP
ADRP
perilipin 2 gamma-Linolenic Acid results in increased expression of PLIN2 mRNA increases expression
mRNA 20664735
D017965 5465 PPARA
NR1C1
PPAR
PPARalpha
hPPAR
peroxisome proliferator-activated receptor alpha gamma-Linolenic Acid binds to and results in increased activity of PPARA protein affects binding
/ increases activity
protein 10403814
D017965 5468 PPARG
CIMT1
GLM1
NR1C3
PPARG1
PPARG2
PPARgamma
peroxisome proliferator-activated receptor gamma gamma-Linolenic Acid binds to and results in increased activity of PPARG protein affects binding
/ increases activity
protein 15318936
D017965 22949 PTGR1
LTB4DH
PGR1
ZADH3
prostaglandin reductase 1 (EC:1.3.1.48 1.3.1.74) gamma-Linolenic Acid results in increased expression of PTGR1 mRNA increases expression
mRNA 20664735
D017965 5743 PTGS2
COX-2
COX2
GRIPGHS
PGG/HS
PGHS-2
PHS-2
hCox-2
prostaglandin-endoperoxide synthase 2 (prostaglandin G/H synthase and cyclooxygenase) (EC:1.14.99.1) gamma-Linolenic Acid results in increased expression of PTGS2 mRNA increases expression
mRNA 17092368
D017965 6286 S100P
MIG9
S100 calcium binding protein P gamma-Linolenic Acid results in increased expression of S100P mRNA increases expression
mRNA 20664735
D017965 6502 SKP2
FBL1
FBXL1
FLB1
p45
S-phase kinase-associated protein 2, E3 ubiquitin protein ligase gamma-Linolenic Acid results in decreased expression of SKP2 mRNA decreases expression
mRNA 20664735
D017965 6520 SLC3A2
4F2
4F2HC
4T2HC
CD98
CD98HC
MDU1
NACAE
solute carrier family 3 (amino acid transporter heavy chain), member 2 gamma-Linolenic Acid results in increased expression of SLC3A2 mRNA increases expression
mRNA 20664735
D017965 6767 ST13
AAG2
FAM10A1
FAM10A4
HIP
HOP
HSPABP
HSPABP1
P48
PRO0786
SNC6
suppression of tumorigenicity 13 (colon carcinoma) (Hsp70 interacting protein) gamma-Linolenic Acid results in increased expression of ST13 mRNA increases expression
mRNA 20664735
D017965 7033 TFF3
ITF
P1B
TFI
trefoil factor 3 (intestinal) gamma-Linolenic Acid results in decreased expression of TFF3 mRNA decreases expression
mRNA 20664735
D017965 7082 TJP1
ZO-1
tight junction protein 1 [gamma-Linolenic Acid co-treated with Iodine co-treated with Selenium] results in increased expression of and results in increased localization of TJP1 protein affects cotreatment
/ increases expression
/ increases localization
protein 16514648
D017965 7124 TNF
DIF
TNF-alpha
TNFA
TNFSF2
tumor necrosis factor gamma-Linolenic Acid results in decreased expression of TNF protein decreases expression
protein 9415022
D017965 7295 TXN
TRDX
TRX
TRX1
thioredoxin gamma-Linolenic Acid results in increased expression of TXN mRNA increases expression
mRNA 20664735
D017965 7296 TXNRD1
GRIM-12
TR
TR1
TRXR1
TXNR
thioredoxin reductase 1 (EC:1.8.1.9) gamma-Linolenic Acid results in increased expression of TXNRD1 mRNA increases expression
mRNA 20664735

Related Disease

Diseases related to proteins in ChEMBL interactions

OMIM (8)

OMIM preferred title UniProt
#114500 Colorectal cancer; crc Q14191
#137800 Glioma susceptibility 1; glm1 O75874
#607948 Mycobacterium tuberculosis, susceptibility to P11473
#604906 Schizophrenia 9; sczd9 P49798
#181500 Schizophrenia; sczd P49798
#277440 Vitamin d-dependent rickets, type 2a; vddr2a P11473
#277700 Werner syndrome; wrn Q14191
#278750 Xeroderma pigmentosum, variant type; xpv Q9Y253

KEGG DISEASE (5)

KEGG disease name UniProt
H00342 Tuberculosis P11473 (related)
H00784 Localized autosomal recessive hypotrichosis P11473 (related)
H01143 Vitamin D-dependent rickets P11473 (related)
H00296 Defects in RecQ helicases Q14191 (related)
H00403 Disorders of nucleotide excision repair Q9Y253 (related)