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Compound Detail

CHEMBL8659

OLEIC ACID
🧪 Phase II
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🧪 Phase II
CCCCCCCC/C=C\CCCCCCCC(=O)O

Basic Information

ChEMBL ID CHEMBL8659
Name OLEIC ACID
Phase Phase II
Structure Type MOL
InChI Key ZQPPMHVWECSIRJ-KTKRTIGZSA-N

Known Names

18:1(N-9) 9-octadecenoic acid, (z)- 9z-octadecenoic acid FEMA NO. 2815 NSC-9856 Oleate Oleic acid Oleic acid component of endocine Osteum Priolene 6936 Vopcolene 27 Wecoline oo
20
Targets
32
Activities
4
Assay Types
0
PK Parameters
20
Publications
12
Known Names
2
Indications

Molecular Properties

282.5
MW (Da)
6.11
ALogP
1
HBA
1
HBD
37.3
PSA (Ų)
0.29
QED
1
Ro5 Violations
15
Rot. Bonds

Drug Information

Molecule Type Small molecule
Chirality Achiral

Flags

Natural Product

Extended Properties

Molecular Formula C18H34O2
MW 282.47
Aromatic Rings 0
Heavy Atoms 20
NP-Likeness 0.87

Indications

Adenoma Multiple Sclerosis

Activity Summary

IC50 15 meas. best 6.22
Ki 7 meas. best 6.75
EC50 5 meas. best 5.02
Kd 5 meas. best 6.7

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Fatty acid-binding protein, liver
CHEMBL5738
Ki 6.75 6.145 180.0 2
Fatty acid-binding protein, adipocyte
CHEMBL2083
Ki 6.73 6.275 185.0 2
Fatty acid-binding protein, liver
CHEMBL5421
Kd 6.7 6.375 200.0 2
Fatty acid-binding protein 5
CHEMBL3674
Ki 6.61 6.61 248.0 1
Peroxisome proliferator-activated receptor alpha
CHEMBL239
IC50 6.22 6.22 600.0 2
Peroxisome proliferator-activated receptor gamma
CHEMBL235
IC50 5.39 5.39 4100.0 1
Peroxisome proliferator-activated receptor delta
CHEMBL3979
IC50 5.28 5.28 5300.0 1
Fatty-acid amide hydrolase 1
CHEMBL2243
Ki 5.22 5.22 6000.0 1
Tyrosine-protein phosphatase non-receptor type 1
CHEMBL335
IC50 5.21 5.21 6200.0 1
Telomerase reverse transcriptase
CHEMBL2916
IC50 5.07 5.07 8600.0 1
NON-PROTEIN TARGET
CHEMBL3879801
EC50 5.02 5.02 9500.0 1
Unchecked
CHEMBL612545
Kd 5.0 5.0 10000.0 1
Voltage-gated inwardly rectifying potassium channel KCNH2
CHEMBL240
EC50 4.98 4.98 10410.0 1
Unchecked
CHEMBL612545
IC50 4.68 4.5333 21000.0 3
Seed linoleate 13S-lipoxygenase-1
CHEMBL4586
Ki 4.66 4.66 22000.0 1
Fatty acid-binding protein, adipocyte
CHEMBL2083
IC50 4.58 4.58 26100.0 1
DNA topoisomerase 1
CHEMBL1781
IC50 4.51 4.51 31000.0 1
Aromatase
CHEMBL1978
IC50 4.49 4.49 32700.0 1
Peroxisome proliferator-activated receptor alpha
CHEMBL239
EC50 4.44 4.44 36000.0 1
Nuclear receptor subfamily 4 group A member 2
CHEMBL5002
Kd 4.3 4.3 50000.0 1
Coagulation factor VII/tissue factor
CHEMBL2095194
IC50 4.1 4.1 80000.0 1
THP-1
CHEMBL614245
IC50 4.1 4.1 79000.0 1
NAD-dependent protein deacylase sirtuin-6
CHEMBL2163182
EC50 4.05 4.05 89000.0 2

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Fatty acid-binding protein, liver Ki = 180.0 nM 6.75 Displacement of 1-anilinonaphthalene-8-sulphonic acid from rat recombinant L-FAB... 18533710
Fatty acid-binding protein, adipocyte Ki = 185.0 nM 6.73 Displacement of 1,8-ANS from aFABP by fluorescence based-assay 17502136
Fatty acid-binding protein, liver Kd = 200.0 nM 6.7 Binding affinity to L-FABP high binding affinity site by titration calorimetry m... 18533710
Fatty acid-binding protein 5 Ki = 248.0 nM 6.61 Displacement of 1,8-ANS from eFABP by fluorescence based-assay 17502136
Peroxisome proliferator-activated receptor alpha IC50 = 600.0 nM 6.22 Inhibition of PPAR-alpha (unknown origin) by SPA assay -
Peroxisome proliferator-activated receptor alpha IC50 = 600.0 nM 6.22 Displacement of [3H]GW2331 from Homo sapiens (human) PPARalpha receptor by scint... -
Fatty acid-binding protein, liver Kd = 900.0 nM 6.05 Binding affinity to L-FABP low binding affinity site by titration calorimetry me... 18533710
Fatty acid-binding protein, adipocyte Ki = 1500.0 nM 5.82 Displacement of 1,8-ANS from His6-tagged FABP4 (unknown origin) expressed in Esc... 27460668
Fatty acid-binding protein, liver Ki = 2900.0 nM 5.54 Displacement of 1-anilinonaphthalene-8-sulphonic acid from rat recombinant L-FAB... 18533710
Peroxisome proliferator-activated receptor gamma IC50 = 4100.0 nM 5.39 Displacement of [3H]BRL49653 from Homo sapiens (human) PPARgamma receptor by sci... -
Peroxisome proliferator-activated receptor delta IC50 = 5300.0 nM 5.28 Displacement of [3H]GW2433 from Homo sapiens (human) PPARdelta receptor by scint... -
Fatty-acid amide hydrolase 1 Ki = 6000.0 nM 5.22 Inhibition of FAAH 18983142
Tyrosine-protein phosphatase non-receptor type 1 IC50 = 6200.0 nM 5.21 Inhibition of PTP1B (unknown origin) using pNPP as substrate incubated for 30 mi... 32255628
Telomerase reverse transcriptase IC50 = 8600.0 nM 5.07 Inhibition of telomerase extracted from human K562 cells preincubated for 10 min... -
NON-PROTEIN TARGET EC50 = 9500.0 nM 5.02 Neuroprotective activity in human SH-SY5Y cells assessed as reduction in 6-OHDA-... 27420919
Unchecked Kd = 10000.0 nM 5.0 Binding affinity to RXR (unknown origin) 28252961
Voltage-gated inwardly rectifying potassium channel KCNH2 EC50 = 10410.0 nM 4.98 PUBCHEM_BIOASSAY: Confirmation Dose Response screen for compounds that protect h... -
Unchecked IC50 = 21000.0 nM 4.68 Inhibition of amidolytic activity of human recombinant soluble tissue factor/hum... 9834151
Seed linoleate 13S-lipoxygenase-1 Ki = 22000.0 nM 4.66 Binding affinity to soybean LO1 19716306
Fatty acid-binding protein, adipocyte IC50 = 26100.0 nM 4.58 Displacement of 8-anilino-1-naphthalene-sulfonic acid from human His-FABP4 expre... 20471252

Literature References

PubMed DOI Target Context # Activities
21780738 10.1021/jf201611b Heterodera zeae 32
- 10.1007/s00044-009-9247-z Rattus norvegicus 20
23121218 10.1021/jf3036885 Meloidogyne incognita 18
9834151 10.1021/np980117p Unchecked 5
17535898 10.1073/pnas.0701015104 Unchecked 5
18533710 10.1021/jm701192w Fatty acid-binding protein, liver 4
21903399 10.1016/j.bmc.2011.08.023 Unchecked 4
34213345 10.1021/acs.jmedchem.1c00601 NAD-dependent protein deacylase sirtuin-6 4
24103427 10.1016/j.bmc.2013.09.034 Mycobacterium tuberculosis 4
35089724 10.1021/acs.jmedchem.1c01542 Peroxisome proliferator-activated receptor alpha 3
16643058 10.1021/np050513p Aromatase 3
31678743 10.1016/j.ejmech.2019.111810 Staphylococcus aureus 3
17954701 10.1128/aac.01009-07 Unchecked 3
22459211 10.1016/j.bmc.2012.02.039 Unchecked 3
18003907 10.1073/pnas.0708423104 Hepatitis C virus 3
21903399 10.1016/j.bmc.2011.08.023 RAW264.7 3
19716306 10.1016/j.bmc.2009.08.005 Seed linoleate 13S-lipoxygenase-1 3
15261286 10.1016/j.bmcl.2004.05.086 Sterol O-acyltransferase 1 3
27460668 10.1016/j.bmc.2016.07.022 Fatty acid-binding protein, adipocyte 3
20014752 10.1021/tx900326k Hepatotoxicity 3

Data from ChEMBL 36 via Core Engine