Metabolite

KNApSAcK Entry

id C00001215
Name (5Z,8Z,11Z,14Z,17Z)-Eicosapentaenoic acid
CAS RN 1553-41-9
Standard InChI InChI=1S/C20H30O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20(21)22/h3-4,6-7,9-10,12-13,15-16H,2,5,8,11,14,17-19H2,1H3,(H,21,22)/b4-3-,7-6-,10-9-,13-12-,16-15-
Standard InChI (Main Layer) InChI=1S/C20H30O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20(21)22/h3-4,6-7,9-10,12-13,15-16H,2,5,8,11,14,17-19H2,1H3,(H,21,22)

Cluster

Phytochemical cluster No. 50
KCF-S cluster No. 2002

Link

ChEMBL

By standard InChI CHEMBL460026
By standard InChI Main Layer CHEMBL460026

KEGG

By LinkDB C06428

CTD

By CAS RN D015118

Human Protein / Gene in interaction

12 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 CHEMBL460026 CHEMBL1794499 (1)
2 / 0
P11473 Vitamin D3 receptor NR1I1 CHEMBL460026 CHEMBL1794311 (1)
2 / 3
P00352 Retinal dehydrogenase 1 Enzyme CHEMBL460026 CHEMBL1614458 (1)
0 / 0
Q9UGP5 DNA polymerase lambda Enzyme CHEMBL460026 CHEMBL1921596 (1) CHEMBL1920071 (1)
0 / 0
Q03164 Histone-lysine N-methyltransferase 2A Enzyme CHEMBL460026 CHEMBL1614410 (1)
1 / 3
O94782 Ubiquitin carboxyl-terminal hydrolase 1 Enzyme CHEMBL460026 CHEMBL1794467 (1)
0 / 0
P11511 Cytochrome P450 19A1 Cytochrome P450 19A1 CHEMBL460026 CHEMBL976708 (1) CHEMBL976710 (1)
CHEMBL976711 (1)
2 / 2
P37231 Peroxisome proliferator-activated receptor gamma NR1C3 CHEMBL460026 CHEMBL2072929 (1)
5 / 3
P13726 Tissue factor Membrane receptor CHEMBL460026 CHEMBL995691 (1)
0 / 0
Q9UBT6 DNA polymerase kappa Enzyme CHEMBL460026 CHEMBL1794536 (1) CHEMBL1921592 (1)
CHEMBL1921595 (1)
0 / 0
Q96KQ7 Histone-lysine N-methyltransferase EHMT2 Enzyme CHEMBL460026 CHEMBL1738442 (1)
0 / 0
O94925 Glutaminase kidney isoform, mitochondrial Enzyme CHEMBL460026 CHEMBL2114738 (1)
0 / 0

CTD interaction (61)

compound gene gene name gene description interaction interaction type form reference
pmid
D015118 19 ABCA1
ABC-1
ABC1
CERP
HDLDT1
TGD
ATP-binding cassette, sub-family A (ABC1), member 1 Eicosapentaenoic Acid results in decreased expression of ABCA1 mRNA decreases expression
mRNA 16730733
D015118 9619 ABCG1
ABC8
WHITE1
ATP-binding cassette, sub-family G (WHITE), member 1 Eicosapentaenoic Acid results in decreased expression of ABCG1 mRNA decreases expression
mRNA 16730733
D015118 9619 ABCG1
ABC8
WHITE1
ATP-binding cassette, sub-family G (WHITE), member 1 Eicosapentaenoic Acid results in decreased expression of ABCG1 protein decreases expression
protein 16730733
D015118 9370 ADIPOQ
ACDC
ACRP30
ADIPQTL1
ADPN
APM-1
APM1
GBP28
adiponectin, C1Q and collagen domain containing Eicosapentaenoic Acid results in increased expression of and results in increased secretion of ADIPOQ protein increases expression
/ increases secretion
protein 20814411
D015118 9370 ADIPOQ
ACDC
ACRP30
ADIPQTL1
ADPN
APM-1
APM1
GBP28
adiponectin, C1Q and collagen domain containing Eicosapentaenoic Acid results in increased secretion of ADIPOQ protein increases secretion
protein 20814411
D015118 338 APOB
FLDB
LDLCQ4
apolipoprotein B [Eicosapentaenoic Acid co-treated with Docosahexaenoic Acids co-treated with Oleic Acid co-treated with Folic Acid co-treated with Vitamin B 6 co-treated with Vitamin E] results in decreased expression of APOB protein affects cotreatment
/ decreases expression
protein 17237316
D015118 836 CASP3
CPP32
CPP32B
SCA-1
caspase 3, apoptosis-related cysteine peptidase (EC:3.4.22.56) [Eicosapentaenoic Acid co-treated with Butyrates] results in increased activity of CASP3 protein affects cotreatment
/ increases activity
protein 19116882
D015118 6347 CCL2
GDCF-2
HC11
HSMCR30
MCAF
MCP-1
MCP1
SCYA2
SMC-CF
chemokine (C-C motif) ligand 2 2,2-bis(4-glycidyloxyphenyl)propane inhibits the reaction [Eicosapentaenoic Acid inhibits the reaction [Lipopolysaccharides results in increased expression of CCL2 mRNA]] decreases reaction
/ increases expression
mRNA 15698426
D015118 6347 CCL2
GDCF-2
HC11
HSMCR30
MCAF
MCP-1
MCP1
SCYA2
SMC-CF
chemokine (C-C motif) ligand 2 Eicosapentaenoic Acid inhibits the reaction [Lipopolysaccharides results in increased expression of CCL2 mRNA] decreases reaction
/ increases expression
mRNA 15698426
D015118 6347 CCL2
GDCF-2
HC11
HSMCR30
MCAF
MCP-1
MCP1
SCYA2
SMC-CF
chemokine (C-C motif) ligand 2 Eicosapentaenoic Acid inhibits the reaction [Lipopolysaccharides results in increased expression of CCL2 protein] decreases reaction
/ increases expression
protein 15698426
D015118 958 CD40
Bp50
CDW40
TNFRSF5
p50
CD40 molecule, TNF receptor superfamily member 5 Eicosapentaenoic Acid inhibits the reaction [Lipopolysaccharides results in increased expression of CD40 mRNA] decreases reaction
/ increases expression
mRNA 15684433
D015118 1401 CRP
PTX1
C-reactive protein, pentraxin-related [Eicosapentaenoic Acid co-treated with Docosahexaenoic Acids co-treated with Oleic Acid co-treated with Folic Acid co-treated with Vitamin B 6 co-treated with Vitamin E] results in decreased expression of CRP protein affects cotreatment
/ decreases expression
protein 17237316
D015118 1535 CYBA
p22-PHOX
cytochrome b-245, alpha polypeptide Eicosapentaenoic Acid results in decreased expression of CYBA mRNA decreases expression
mRNA 11172467
D015118 1544 CYP1A2
CP12
P3-450
P450(PA)
cytochrome P450, family 1, subfamily A, polypeptide 2 (EC:1.14.14.1) Eicosapentaenoic Acid results in decreased activity of CYP1A2 protein decreases activity
protein 16978661
D015118 1557 CYP2C19
CPCJ
CYP2C
P450C2C
P450IIC19
cytochrome P450, family 2, subfamily C, polypeptide 19 (EC:1.14.13.48 1.14.13.49 1.14.13.80) CYP2C19 protein results in increased metabolism of [Eicosapentaenoic Acid co-treated with NADP] affects cotreatment
/ increases metabolic processing
protein 16978661
D015118 1557 CYP2C19
CPCJ
CYP2C
P450C2C
P450IIC19
cytochrome P450, family 2, subfamily C, polypeptide 19 (EC:1.14.13.48 1.14.13.49 1.14.13.80) Eicosapentaenoic Acid results in decreased activity of CYP2C19 protein decreases activity
protein 16978661
D015118 1559 CYP2C9
CPC9
CYP2C
CYP2C10
CYPIIC9
P450IIC9
cytochrome P450, family 2, subfamily C, polypeptide 9 (EC:1.14.13.48 1.14.13.49 1.14.13.80) CYP2C9 protein results in increased metabolism of [Eicosapentaenoic Acid co-treated with NADP] affects cotreatment
/ increases metabolic processing
protein 16978661
D015118 1559 CYP2C9
CPC9
CYP2C
CYP2C10
CYPIIC9
P450IIC9
cytochrome P450, family 2, subfamily C, polypeptide 9 (EC:1.14.13.48 1.14.13.49 1.14.13.80) Eicosapentaenoic Acid results in decreased activity of CYP2C9 protein decreases activity
protein 16978661
D015118 1571 CYP2E1
CPE1
CYP2E
P450-J
P450C2E
cytochrome P450, family 2, subfamily E, polypeptide 1 (EC:1.14.13.n7) Eicosapentaenoic Acid results in decreased activity of CYP2E1 protein decreases activity
protein 16978661
D015118 1576 CYP3A4
CP33
CP34
CYP3A
CYP3A3
CYPIIIA3
CYPIIIA4
HLP
NF-25
P450C3
P450PCN1
cytochrome P450, family 3, subfamily A, polypeptide 4 (EC:1.14.13.67 1.14.13.97 1.14.13.32 1.14.13.157) Eicosapentaenoic Acid results in decreased activity of CYP3A4 protein decreases activity
protein 16978661
D015118 117159 DCD
AIDD
DCD-1
DSEP
HCAP
PIF
dermcidin Eicosapentaenoic Acid inhibits the reaction [DCD protein results in increased expression of PSMA2 mRNA] decreases reaction
/ increases expression
protein 15451026
D015118 117159 DCD
AIDD
DCD-1
DSEP
HCAP
PIF
dermcidin Eicosapentaenoic Acid inhibits the reaction [DCD protein results in increased expression of PSMB5 mRNA] decreases reaction
/ increases expression
protein 15451026
D015118 2729 GCLC
GCL
GCS
GLCL
GLCLC
glutamate-cysteine ligase, catalytic subunit (EC:6.3.2.2) Eicosapentaenoic Acid results in increased activity of GCLC protein increases activity
protein 17092368
D015118 2729 GCLC
GCL
GCS
GLCL
GLCLC
glutamate-cysteine ligase, catalytic subunit (EC:6.3.2.2) Eicosapentaenoic Acid results in increased expression of GCLC mRNA increases expression
mRNA 17092368
D015118 3162 HMOX1
HMOX1D
HO-1
HSP32
bK286B10
heme oxygenase (decycling) 1 (EC:1.14.99.3) Eicosapentaenoic Acid results in increased expression of HMOX1 mRNA increases expression
mRNA 17092368
D015118 3593 IL12B
CLMF
CLMF2
IL-12B
NKSF
NKSF2
interleukin 12B (natural killer cell stimulatory factor 2, cytotoxic lymphocyte maturation factor 2, p40) Eicosapentaenoic Acid inhibits the reaction [Lipopolysaccharides results in increased expression of IL12B mRNA] decreases reaction
/ increases expression
mRNA 15684433
D015118 3553 IL1B
IL-1
IL1-BETA
IL1F2
interleukin 1, beta alpha-pentyl-3-(2-quinolinylmethoxy)benzenemethanol inhibits the reaction [Eicosapentaenoic Acid inhibits the reaction [IL1B protein results in increased expression of PTGS2 protein]] decreases reaction
/ increases expression
protein 12573452
D015118 3553 IL1B
IL-1
IL1-BETA
IL1F2
interleukin 1, beta [Eicosapentaenoic Acid co-treated with Docosahexaenoic Acids co-treated with alpha-Linolenic Acid] results in increased expression of IL1B protein affects cotreatment
/ increases expression
protein 16305726
D015118 3553 IL1B
IL-1
IL1-BETA
IL1F2
interleukin 1, beta Eicosapentaenoic Acid inhibits the reaction [IL1B protein results in increased expression of PTGS2 protein] decreases reaction
/ increases expression
protein 12573452
D015118 3553 IL1B
IL-1
IL1-BETA
IL1F2
interleukin 1, beta Eicosapentaenoic Acid results in decreased expression of IL1B protein decreases expression
protein 9415022
D015118 3553 IL1B
IL-1
IL1-BETA
IL1F2
interleukin 1, beta Masoprocol inhibits the reaction [Eicosapentaenoic Acid inhibits the reaction [IL1B protein results in increased expression of PTGS2 protein]] decreases reaction
/ increases expression
protein 12573452
D015118 3558 IL2
IL-2
TCGF
lymphokine
interleukin 2 Eicosapentaenoic Acid results in decreased expression of IL2 protein decreases expression
protein 9415022
D015118 3565 IL4
BCGF-1
BCGF1
BSF-1
BSF1
IL-4
interleukin 4 [Eicosapentaenoic Acid co-treated with Docosahexaenoic Acids co-treated with alpha-Linolenic Acid] results in decreased expression of IL4 protein affects cotreatment
/ decreases expression
protein 16305726
D015118 3569 IL6
BSF2
HGF
HSF
IFNB2
IL-6
interleukin 6 (interferon, beta 2) [Polyphenols co-treated with Antioxidants co-treated with Eicosapentaenoic Acid co-treated with Docosahexaenoic Acids co-treated with Medroxyprogesterone Acetate co-treated with celecoxib] results in decreased expression of IL6 affects cotreatment
/ decreases expression
16702388
D015118 3952 LEP
LEPD
OB
OBS
leptin Eicosapentaenoic Acid results in decreased expression of LEP mRNA decreases expression
mRNA 15949695
D015118 778733 Eicosapentaenoic Acid results in decreased expression of PPAR mRNA decreases expression
mRNA 15949695
D015118 5465 PPARA
NR1C1
PPAR
PPARalpha
hPPAR
peroxisome proliferator-activated receptor alpha Eicosapentaenoic Acid binds to and results in increased activity of PPARA protein affects binding
/ increases activity
protein 10403814
D015118 5465 PPARA
NR1C1
PPAR
PPARalpha
hPPAR
peroxisome proliferator-activated receptor alpha Eicosapentaenoic Acid results in increased expression of PPARA mRNA increases expression
mRNA 11172467
D015118 5465 PPARA
NR1C1
PPAR
PPARalpha
hPPAR
peroxisome proliferator-activated receptor alpha Eicosapentaenoic Acid results in increased expression of PPARA protein increases expression
protein 11172467
D015118 5467 PPARD
FAAR
NR1C2
NUC1
NUCI
NUCII
PPARB
peroxisome proliferator-activated receptor delta Eicosapentaenoic Acid results in increased expression of PPARD mRNA increases expression
mRNA 11172467
D015118 5468 PPARG
CIMT1
GLM1
NR1C3
PPARG1
PPARG2
PPARgamma
peroxisome proliferator-activated receptor gamma 2,2-bis(4-glycidyloxyphenyl)propane inhibits the reaction [Eicosapentaenoic Acid results in increased activity of PPARG protein] decreases reaction
/ increases activity
protein 15698426
D015118 5468 PPARG
CIMT1
GLM1
NR1C3
PPARG1
PPARG2
PPARgamma
peroxisome proliferator-activated receptor gamma Eicosapentaenoic Acid results in increased activity of PPARG protein increases activity
protein 15698426
D015118 5468 PPARG
CIMT1
GLM1
NR1C3
PPARG1
PPARG2
PPARgamma
peroxisome proliferator-activated receptor gamma Eicosapentaenoic Acid results in increased expression of PPARG mRNA increases expression
mRNA 11172467
15698426
D015118 5468 PPARG
CIMT1
GLM1
NR1C3
PPARG1
PPARG2
PPARgamma
peroxisome proliferator-activated receptor gamma Eicosapentaenoic Acid results in increased expression of PPARG protein increases expression
protein 11172467
D015118 10891 PPARGC1A
LEM6
PGC-1(alpha)
PGC-1v
PGC1
PGC1A
PPARGC1
peroxisome proliferator-activated receptor gamma, coactivator 1 alpha Eicosapentaenoic Acid results in increased expression of PPARGC1A mRNA increases expression
mRNA 23056435
D015118 5683 PSMA2
HC3
MU
PMSA2
PSC2
proteasome (prosome, macropain) subunit, alpha type, 2 (EC:3.4.25.1) Eicosapentaenoic Acid inhibits the reaction [DCD protein results in increased expression of PSMA2 mRNA] decreases reaction
/ increases expression
mRNA 15451026
D015118 5693 PSMB5
LMPX
MB1
X
proteasome (prosome, macropain) subunit, beta type, 5 (EC:3.4.25.1) Eicosapentaenoic Acid inhibits the reaction [DCD protein results in increased expression of PSMB5 mRNA] decreases reaction
/ increases expression
mRNA 15451026
D015118 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) alpha-pentyl-3-(2-quinolinylmethoxy)benzenemethanol inhibits the reaction [Eicosapentaenoic Acid inhibits the reaction [IL1B protein results in increased expression of PTGS2 protein]] decreases reaction
/ increases expression
protein 12573452
D015118 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) Eicosapentaenoic Acid inhibits the reaction [IL1B protein results in increased expression of PTGS2 protein] decreases reaction
/ increases expression
protein 12573452
D015118 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) Eicosapentaenoic Acid inhibits the reaction [Lipopolysaccharides results in increased expression of PTGS2 mRNA] decreases reaction
/ increases expression
mRNA 15684433
D015118 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) Eicosapentaenoic Acid results in increased expression of PTGS2 mRNA increases expression
mRNA 17092368
D015118 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) Masoprocol inhibits the reaction [Eicosapentaenoic Acid inhibits the reaction [IL1B protein results in increased expression of PTGS2 protein]] decreases reaction
/ increases expression
protein 12573452
D015118 5970 RELA
NFKB3
p65
v-rel avian reticuloendotheliosis viral oncogene homolog A 2,2-bis(4-glycidyloxyphenyl)propane inhibits the reaction [Eicosapentaenoic Acid inhibits the reaction [Lipopolysaccharides results in increased activity of RELA protein]] decreases reaction
/ increases activity
protein 15698426
D015118 5970 RELA
NFKB3
p65
v-rel avian reticuloendotheliosis viral oncogene homolog A Eicosapentaenoic Acid inhibits the reaction [Lipopolysaccharides results in increased activity of RELA protein] decreases reaction
/ increases activity
protein 15698426
D015118 56729 RETN
ADSF
FIZZ3
RETN1
RSTN
XCP1
resistin Eicosapentaenoic Acid results in decreased expression of RETN mRNA decreases expression
mRNA 15949695
D015118 6647 SOD1
ALS
ALS1
IPOA
SOD
hSod1
homodimer
superoxide dismutase 1, soluble (EC:1.15.1.1) Eicosapentaenoic Acid results in increased expression of SOD1 mRNA increases expression
mRNA 11172467
D015118 6647 SOD1
ALS
ALS1
IPOA
SOD
hSod1
homodimer
superoxide dismutase 1, soluble (EC:1.15.1.1) Eicosapentaenoic Acid results in increased expression of SOD1 protein increases expression
protein 11172467
D015118 6720 SREBF1
SREBP-1c
SREBP1
bHLHd1
sterol regulatory element binding transcription factor 1 Eicosapentaenoic Acid results in decreased expression of SREBF1 mRNA decreases expression
mRNA 15949695
D015118 7124 TNF
DIF
TNF-alpha
TNFA
TNFSF2
tumor necrosis factor Eicosapentaenoic Acid inhibits the reaction [Lipopolysaccharides results in increased expression of TNF mRNA] decreases reaction
/ increases expression
mRNA 15684433
D015118 7124 TNF
DIF
TNF-alpha
TNFA
TNFSF2
tumor necrosis factor Eicosapentaenoic Acid results in decreased expression of TNF protein decreases expression
protein 9415022
D015118 7124 TNF
DIF
TNF-alpha
TNFA
TNFSF2
tumor necrosis factor [Polyphenols co-treated with Antioxidants co-treated with Eicosapentaenoic Acid co-treated with Docosahexaenoic Acids co-treated with Medroxyprogesterone Acetate co-treated with celecoxib] results in decreased expression of TNF affects cotreatment
/ decreases expression
16702388

Related Disease

Diseases related to proteins in ChEMBL interactions

OMIM (12)

OMIM preferred title UniProt
#613546 Aromatase deficiency P11511
#139300 Aromatase excess syndrome; aexs P11511
%606641 Body mass index; bmi P37231
#609338 Carotid intimal medial thickness 1 P37231
#137800 Glioma susceptibility 1; glm1 P37231
#605130 Hairy elbows, short stature, facial dysmorphism, and developmental delay Q03164
#604367 Lipodystrophy, familial partial, type 3; fpld3 P37231
#607948 Mycobacterium tuberculosis, susceptibility to P11473
#601665 Obesity P37231
#604906 Schizophrenia 9; sczd9 P49798
#181500 Schizophrenia; sczd P49798
#277440 Vitamin d-dependent rickets, type 2a; vddr2a P11473

KEGG DISEASE (10)

KEGG disease name UniProt
H00342 Tuberculosis P11473 (related)
H00784 Localized autosomal recessive hypotrichosis P11473 (related)
H01143 Vitamin D-dependent rickets P11473 (related)
H00599 46,XX disorders of sex development (Disorders related to androgen excess) P11511 (related)
H00794 Aromatase excess syndrome P11511 (related)
H00032 Thyroid cancer P37231 (related)
H00409 Type II diabetes mellitus P37231 (related)
H00420 Familial partial lipodystrophy (FPL) P37231 (related)
H00001 Acute lymphoblastic leukemia (ALL) (precursor B lymphoblastic leukemia) Q03164 (related)
Q03164 (marker)
H00002 Acute lymphoblastic leukemia (ALL) (precursor T lymphoblastic leukemia) Q03164 (related)

Diseases related to CTD interactions

17 disease from interactions of metabolites

MeSH disease OMIM compound disease name evidence type reference
pmid
D000743 D015118 Anemia, Hemolytic marker/mechanism
12736713
D001145 D015118 Arrhythmias, Cardiac therapeutic
15990700
D002114 D015118 Calcinosis therapeutic
21193197
D002318 D015118 Cardiovascular Diseases therapeutic
21193197
D003327 D015118 Coronary Disease therapeutic
18986590
D003866 D015118 Depressive Disorder therapeutic
11695079
D050171 D015118 Dyslipidemias therapeutic
19277604
D018149 D015118 Glucose Intolerance therapeutic
19277604
D006973 D015118 Hypertension therapeutic
12661920
D015228 D015118 Hypertriglyceridemia therapeutic
12661920
D007333 D015118 Insulin Resistance therapeutic
10753628
19277604
D007414 D015118 Intestinal Neoplasms therapeutic
11714441
D048629 D015118 Micronuclei, Chromosome-Defective therapeutic
20052769
D010146 D015118 Pain therapeutic
17038422
D010300 D015118 Parkinson Disease therapeutic
20868657
D012559 D015118 Schizophrenia therapeutic
14623502
D013927 D015118 Thrombosis therapeutic
15990700