Compound Detail

CHEMBL168

OLEANOLIC_ACID

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CC1(C)CC[C@]2(C(=O)O)CC[C@]3(C)C(=CC[C@@H]4[C@@]5(C)CC[C@H](O)C(C)(C)[C@@H]5CC[C@]43C)[C@@H]2C1

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL168
Name	OLEANOLIC_ACID
Phase	Preclinical
Structure Type	MOL
InChI Key	MIJYXULNPSFWEK-GTOFXWBISA-N

Targets

265

Activities

Assay Types

PK Parameters

Publications

Known Names

Molecular Properties

456.7

MW (Da)

7.23

ALogP

HBA

HBD

57.5

PSA (Å²)

0.41

QED

Ro5 Violations

Rot. Bonds

Drug Information

Molecule Type	Small molecule
Availability	Unknown
Chirality	Unknown

Flags

Natural Product First in Class Prodrug

Extended Properties

Molecular Formula	C30H48O3
MW	456.71
Aromatic Rings	0
Heavy Atoms	33
NP-Likeness	3.27

Activity Summary

IC50 225 meas. best 8.37

EC50 29 meas. best 8.0

Ki 10 meas. best 7.14

Kd 1 meas. best 4.96

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
MCF7 CHEMBL387	IC50	8.37	5.655	4.2	4
Tissue factor CHEMBL4081	IC50	8.3	8.3	5.0	1
Human immunodeficiency virus 1 CHEMBL378	EC50	8.0	8.0	10.0	1
Unchecked CHEMBL612545	EC50	7.22	7.22	59.6	1
Aldo-keto reductase family 1 member B10 CHEMBL5983	Ki	7.14	6.32	72.0	5
FUN14 domain-containing protein 1 CHEMBL6067457	Ki	7.14	7.14	72.0	1
Aldo-keto reductase family 1 member B10 CHEMBL5983	IC50	7.05	6.225	90.0	2
Liver carboxylesterase 1 CHEMBL2265	IC50	7.0	7.0	100.0	1
A549 CHEMBL392	IC50	6.41	4.648	390.0	10
Unchecked CHEMBL612545	IC50	6.35	4.8653	449.0	15
Tyrosine-protein phosphatase non-receptor type 1 CHEMBL335	IC50	6.3	5.6072	500.0	47
Tyrosine-protein phosphatase non-receptor type 2 CHEMBL3807	IC50	6.16	5.3694	700.0	16
Neutrophil CHEMBL613710	IC50	6.12	5.99	750.0	2
M-phase inducer phosphatase 2 CHEMBL4804	IC50	6.01	6.01	980.0	1
Receptor-type tyrosine-protein phosphatase C CHEMBL3243	IC50	6.0	6.0	1000.0	1
Unchecked CHEMBL612545	Ki	5.7	5.7	2000.0	1
G-protein coupled bile acid receptor 1 CHEMBL5409	EC50	5.65	5.65	2250.0	2
Transcription factor p65 CHEMBL5533	IC50	5.62	5.62	2400.0	1
BGC-823 CHEMBL614526	IC50	5.59	5.59	2590.0	1
Phospholipase A2 CHEMBL4426	IC50	5.52	5.52	3000.0	1
DNA polymerase beta CHEMBL2392	IC50	5.52	4.964	3000.0	5
DNA polymerase beta CHEMBL4343	IC50	5.43	5.275	3700.0	2
H9 CHEMBL614806	EC50	5.43	5.43	3700.0	1
Tyrosine-protein phosphatase non-receptor type 1 CHEMBL335	Ki	5.4	5.28	4000.0	3
HCT-116 CHEMBL394	IC50	5.32	4.905	4800.0	2
B16 CHEMBL381	IC50	5.32	5.32	4800.0	1
Dual specificity protein phosphatase 3 CHEMBL2635	IC50	5.27	5.27	5400.0	1
PC-3 CHEMBL390	IC50	5.19	5.19	6510.0	1
Trypanosoma brucei brucei CHEMBL612851	IC50	5.19	4.78	6400.0	2
Protease CHEMBL2366517	IC50	5.1	4.5267	8000.0	3
PC-12 CHEMBL612556	EC50	5.07	5.07	8550.0	1
Hepatitis C virus CHEMBL379	IC50	5.0	5.0	10000.0	2
Hemagglutinin CHEMBL3559640	Kd	4.96	4.96	10900.0	1
Tyrosine-protein phosphatase non-receptor type 11 CHEMBL3864	IC50	4.93	4.93	11620.0	1
Receptor-type tyrosine-protein phosphatase F CHEMBL3521	IC50	4.93	4.79	11800.0	2
Ubiquitin carboxyl-terminal hydrolase 7 CHEMBL2157850	IC50	4.9	4.9	12500.0	1
Tyrosine-protein phosphatase non-receptor type 6 CHEMBL3166	IC50	4.85	4.675	14190.0	2
A2780 CHEMBL614004	IC50	4.85	4.85	14000.0	1
Phosphotyrosine protein phosphatase CHEMBL4295521	IC50	4.85	4.7233	14000.0	3
A2780 CHEMBL614004	EC50	4.85	4.6975	14000.0	4
Glycogen phosphorylase, muscle form CHEMBL4696	IC50	4.85	4.7833	14000.0	6
ADMET CHEMBL612558	IC50	4.84	4.45	14500.0	2
HepG2 CHEMBL395	IC50	4.83	4.64	14720.0	3
HL-60 CHEMBL383	IC50	4.83	4.5425	14750.0	4
NON-PROTEIN TARGET CHEMBL3879801	IC50	4.73	4.398	18520.0	5
Low molecular weight phosphotyrosine protein phosphatase CHEMBL4903	IC50	4.67	4.655	21200.0	4
Plasmodium falciparum CHEMBL364	IC50	4.62	4.6	23810.0	2
HL60/ADR CHEMBL4296430	IC50	4.54	4.54	28750.0	1
HeLa CHEMBL399	IC50	4.5	4.5	31380.0	1
J774.A1 CHEMBL614040	IC50	4.45	4.45	35200.0	1

Pharmacokinetic Data

Parameter	Value	Units	Species
AUC	291.47	ng.hr.mL-1	Cavia porcellus
AUC	312.41	ng.hr.mL-1	Cavia porcellus
Cmax	114.27	nM	Cavia porcellus
F	0.7	%	Rattus norvegicus
MRT	11.72	hr	Cavia porcellus
MRT	14.97	hr	Cavia porcellus
T1/2	11.74	hr	Cavia porcellus
T1/2	0.7	hr	Mus musculus
Tmax	0.75	hr	Cavia porcellus

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
MCF7	IC50	=	4.23	nM	8.37	Antiproliferative activity against human MCF7 cells assessed as inhibition of ce...	37847948
Tissue factor	IC50	=	4.975	nM	8.3	Inhibition of LPS-induced tissue factor procoagulant activity in human THP1 cell...	28109788
Human immunodeficiency virus 1	EC50	=	10.0	nM	8.0	Antiviral activity against HIV-1 3B	31499360
Unchecked	EC50	=	59.6	nM	7.22	Antiproliferative activity against rat HSC-T6 cells assessed as reduction in cel...	29353722
Aldo-keto reductase family 1 member B10	Ki	=	72.0	nM	7.14	Competitive inhibition of dehydrogenase activity of N-terminal 6His-tagged human...	21561086
FUN14 domain-containing protein 1	Ki	=	72.0	nM	7.14	Binding affinity to FUNDC1 (unknown origin) assessed as inhibition constant	38295689
Aldo-keto reductase family 1 member B10	IC50	=	90.0	nM	7.05	Inhibition of reductase activity of N-terminal 6His-tagged human AKR1B10 express...	21561086
Liver carboxylesterase 1	IC50	=	100.0	nM	7.0	Inhibition of CES1A1 in human liver microsomes using D-luciferin methyl ester as...	32951423
Aldo-keto reductase family 1 member B10	Ki	=	160.0	nM	6.8	Competitive inhibition of dehydrogenase activity of N-terminal 6His-tagged human...	21561086
A549	IC50	=	390.0	nM	6.41	Cytotoxicity against human A549 cells by MTT assay	23434227
Unchecked	IC50	=	449.0	nM	6.35	Inhibition of TPA-induced EBV-early antigen activation in human Raji cells asses...	21620532
Tyrosine-protein phosphatase non-receptor type 1	IC50	=	500.0	nM	6.3	Inhibition of human recombinant PTP1B using pNPP as substrate assessed as reduct...	34710624
Aldo-keto reductase family 1 member B10	Ki	=	660.0	nM	6.18	Competitive inhibition of dehydrogenase activity of N-terminal 6His-tagged human...	21561086
Tyrosine-protein phosphatase non-receptor type 1	IC50	=	700.0	nM	6.16	Inhibition of PTP1B (unknown origin)	26115570
Tyrosine-protein phosphatase non-receptor type 2	IC50	=	700.0	nM	6.16	Inhibition of human recombinant TCPTP using pNPP as substrate assessed as reduct...	34710624
Tyrosine-protein phosphatase non-receptor type 1	IC50	=	700.0	nM	6.16	Inhibition of PTP1B (unknown origin) pre-incubated for 10 mins before addition o...	26253631
Tyrosine-protein phosphatase non-receptor type 1	IC50	=	730.0	nM	6.14	Inhibition of recombinant human PTP1B using pNPP as substrate incubated for 10 m...	26711144
Neutrophil	IC50	=	750.0	nM	6.12	Inhibition of fMLP/CB-activated human neutrophil degranulation assessed as inhib...	21417387
Aldo-keto reductase family 1 member B10	Ki	=	940.0	nM	6.03	Competitive inhibition of dehydrogenase activity of N-terminal 6His-tagged human...	21561086
M-phase inducer phosphatase 2	IC50	=	980.0	nM	6.01	Inhibition of CDC25B (unknown origin) using pNPP as substrate by spectrophotomet...	25497963

Literature References

PubMed	DOI	Target Context	# Activities
-	10.1016/j.cropro.2007.03.015	Carassius auratus	21
32191471	10.1021/acs.jnatprod.9b01210	Rattus norvegicus	17
-	10.1016/j.cropro.2007.03.015	Oreochromis	14
-	10.1007/s00044-012-0014-1	Mus musculus	14
24480359	10.1016/j.ejmech.2013.12.049	B16-F10	11
21561086	10.1021/np200118q	Aldo-keto reductase family 1 member B10	9
28802120	10.1016/j.ejmech.2017.08.012	Cavia porcellus	8
17270438	10.1016/j.bmcl.2006.12.091	Mus musculus	8
-	10.1016/j.cropro.2007.03.015	Pomacea canaliculata	8
25794790	10.1016/j.ejmech.2015.01.015	Streptomyces scabiei	7
28964635	10.1016/j.bmcl.2017.09.027	Pancreatic alpha-amylase	7
18598019	10.1021/jm800167u	NON-PROTEIN TARGET	7
19716700	10.1016/j.bmcl.2009.08.048	HepG2	6
22339499	10.1021/np200823p	Nuclear factor erythroid 2-related factor 2	6
20153563	10.1016/j.ejmech.2010.01.057	Unchecked	5
2832544	10.1021/np50054a031	Unchecked	5
21561086	10.1021/np200118q	HT-29	5
21620532	10.1016/j.ejmech.2011.04.062	Unchecked	5
16792424	10.1021/np0601152	Mus musculus	5
23123017	10.1016/j.bmc.2012.10.010	Raji	5

Data from ChEMBL 36 via Core Engine