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Compound Detail

CHEMBL464982

GAMOLENIC ACID
🧪 Phase III
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🧪 Phase III
CCCCC/C=C\C/C=C\C/C=C\CCCCC(=O)O
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL464982
Name GAMOLENIC ACID
Phase Phase III
Structure Type MOL
InChI Key VZCCETWTMQHEPK-QNEBEIHSSA-N
Therapeutic ✓ Yes

Known Names

(6z,9z,12z-octadecatrienoic acid .gamma.-linolenic acid 18:3(N-6) Acide gamolenique Acido gamolenico C18:3 (n-6) Delta-linolenic acid Efamast 40 Efamast 80 Epoc Epogam Epogam 40 +15 more
7
Targets
9
Activities
2
Assay Types
0
PK Parameters
20
Publications
27
Known Names
2
Indications

Molecular Properties

278.4
MW (Da)
5.66
ALogP
1
HBA
1
HBD
37.3
PSA (Ų)
0.35
QED
1
Ro5 Violations
13
Rot. Bonds

Drug Information

Molecule Type Small molecule
Chirality Achiral

Flags

Natural Product

Extended Properties

Molecular Formula C18H30O2
MW 278.44
Aromatic Rings 0
Heavy Atoms 20
NP-Likeness 1.13

Indications

Arthritis, Rheumatoid Asthma

ATC Classification

D11AX02
gamolenic acid
Level 1: DERMATOLOGICALS
Level 2: OTHER DERMATOLOGICAL PREPARATIONS
D11AX52
gamolenic acid, combinations
Level 1: DERMATOLOGICALS
Level 2: OTHER DERMATOLOGICAL PREPARATIONS

Activity Summary

IC50 8 meas. best 6.57
EC50 1 meas. best 5.33

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Peroxisome proliferator-activated receptor alpha
CHEMBL239
 IC50 6.57 6.57 270.0 2
Peroxisome proliferator-activated receptor delta
CHEMBL3979
 IC50 6.12 6.12 750.0 1
Peroxisome proliferator-activated receptor gamma
CHEMBL235
 IC50 5.66 5.66 2200.0 1
Free fatty acid receptor 1
CHEMBL4422
 EC50 5.33 5.33 4620.0 1
3-oxo-5-alpha-steroid 4-dehydrogenase 2
CHEMBL1856
 IC50 4.85 4.85 14000.0 1
Unchecked
CHEMBL612545
 IC50 4.7 4.525 20000.0 2
Coagulation factor VII/tissue factor
CHEMBL2095194
 IC50 4.52 4.52 30000.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Peroxisome proliferator-activated receptor alpha IC50 = 270.0 nM 6.57 Inhibition of PPAR-alpha (unknown origin) by SPA assay -
Peroxisome proliferator-activated receptor alpha IC50 = 270.0 nM 6.57 Displacement of [3H]GW2331 from Homo sapiens (human) PPARalpha receptor by scint... -
Peroxisome proliferator-activated receptor delta IC50 = 750.0 nM 6.12 Displacement of [3H]GW2433 from Homo sapiens (human) PPARdelta receptor by scint... -
Peroxisome proliferator-activated receptor gamma IC50 = 2200.0 nM 5.66 Displacement of [3H]BRL49653 from Homo sapiens (human) PPARgamma receptor by sci... -
Free fatty acid receptor 1 EC50 = 4620.0 nM 5.33 Agonist activity at human FFAR1 expressed in CHO-K1 cells assessed as calcium fl... 26774923
3-oxo-5-alpha-steroid 4-dehydrogenase 2 IC50 = 14000.0 nM 4.85 In Vitro Inhibition Assay: This work was performed at the MDS Pharma Services, P... -
Unchecked IC50 = 20000.0 nM 4.7 Inhibition of amidolytic activity of human recombinant soluble tissue factor/hum... 9834151
Coagulation factor VII/tissue factor IC50 = 30000.0 nM 4.52 Inhibition of amidolytic activity of human tissue factor/human factor 7a 9834151
Unchecked IC50 = 45000.0 nM 4.35 Inhibition of amidolytic activity of human recombinant soluble tissue factor/hum... 9834151

Literature References

PubMed DOI Target Context # Activities
9834151 10.1021/np980117p Unchecked 5
37468498 10.1038/s41467-023-40064-9 Thromboxane A2 receptor 2
37468498 10.1038/s41467-023-40064-9 Prostaglandin G/H synthase 1 2
21726077 10.1021/jm2005805 Fatty acid synthase 2
37468498 10.1038/s41467-023-40064-9 Alpha-1A adrenergic receptor 2
37468498 10.1038/s41467-023-40064-9 Muscarinic acetylcholine receptor M1 2
- 10.6019/CHEMBL4808148 Histone deacetylase 6 2
- 10.6019/CHEMBL4495565 SARS-CoV-2 2
- 10.21203/rs.3.rs-23951/v1 SARS-CoV-2 1
37468498 10.1038/s41467-023-40064-9 Acetylcholinesterase 1
37468498 10.1038/s41467-023-40064-9 Estrogen receptor 1
37468498 10.1038/s41467-023-40064-9 Voltage-gated inwardly rectifying potassium channel KCNH2 1
37468498 10.1038/s41467-023-40064-9 D(1A) dopamine receptor 1
- 10.6019/CHEMBL4495564 Replicase polyprotein 1ab 1
- 10.1007/s00044-012-0285-6 Peroxisome proliferator-activated receptor alpha 1
- 10.1007/s00044-012-0285-6 Peroxisome proliferator-activated receptor gamma 1
- 10.1007/s00044-012-0285-6 Peroxisome proliferator-activated receptor delta 1
- 10.1007/s00044-008-9102-7 Peroxisome proliferator-activated receptor alpha 1
9834151 10.1021/np980117p Trypsin 1
9834151 10.1021/np980117p No relevant target 1

Data from ChEMBL 36 via Core Engine