Compound Detail

CHEMBL169

URSOLIC ACID

🧪 Phase II

Enter ChEMBL ID:

Free Research Context This compound will appear in recent viewed items on the research home for this browser.

Research home View demo workspace

🧪 Phase II

C[C@H]1[C@H](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]12

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL169
Name	URSOLIC ACID
Phase	Phase II
Structure Type	MOL
InChI Key	WCGUUGGRBIKTOS-GPOJBZKASA-N

Known Names

Malol Micromerol NSC-167406 NSC-4060 Prunol Ursolic acid Urson

Targets

291

Activities

Assay Types

PK Parameters

Publications

Known Names

Indications

Molecular Properties

456.7

MW (Da)

7.09

ALogP

HBA

HBD

57.5

PSA (Å²)

0.41

QED

Ro5 Violations

Rot. Bonds

Drug Information

Molecule Type	Small molecule
Chirality	Single Enantiomer

Flags

Natural Product

Extended Properties

Molecular Formula	C30H48O3
MW	456.71
Aromatic Rings	0
Heavy Atoms	33
NP-Likeness	3.19

Indications

Metabolic Syndrome Cholangitis, Sclerosing Prostatic Neoplasms, Castration-Resistant

Activity Summary

IC50 242 meas. best 9.12

EC50 39 meas. best 8.0

Ki 9 meas. best 6.05

Kd 1 meas. best 4.33

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
Nuclear receptor ROR-gamma CHEMBL1741186	IC50	9.12	6.636	0.8	5
Unchecked CHEMBL612545	IC50	8.6	5.0828	2.5	25
Sentrin-specific protease 1 CHEMBL1909484	IC50	8.19	6.4533	6.4	3
Human immunodeficiency virus 1 CHEMBL378	EC50	8.0	8.0	10.0	1
Transcription factor p65 CHEMBL5533	IC50	7.51	7.51	31.0	1
Liver carboxylesterase 1 CHEMBL2265	IC50	7.0	7.0	100.0	1
Streptococcus CHEMBL612313	EC50	6.06	6.06	880.0	1
Unchecked CHEMBL612545	Ki	6.05	6.05	900.0	1
Streptococcus sp. 'group A' CHEMBL612389	EC50	6.02	6.02	949.0	1
Toxoplasma gondii CHEMBL612888	IC50	6.0	5.615	1000.0	2
G-protein coupled bile acid receptor 1 CHEMBL5409	EC50	5.96	5.9	1100.0	2
Streptokinase A CHEMBL1293228	EC50	5.75	5.75	1790.0	1
ADMET CHEMBL612558	IC50	5.75	4.8217	1800.0	6
11-beta-hydroxysteroid dehydrogenase 1 CHEMBL4235	IC50	5.72	5.72	1900.0	1
Tyrosine-protein phosphatase non-receptor type 1 CHEMBL335	Ki	5.7	5.4533	2000.0	3
Aldo-keto reductase family 1 member B10 CHEMBL5983	Ki	5.7	5.516	2000.0	5
Trypanosoma brucei brucei CHEMBL612851	IC50	5.66	5.66	2200.0	1
Tyrosine-protein phosphatase non-receptor type 1 CHEMBL335	IC50	5.64	5.29	2300.0	43
Acidic phospholipase A2 EC-I CHEMBL4195	IC50	5.64	5.64	2300.0	1
Tyrosine-protein phosphatase non-receptor type 2 CHEMBL3807	IC50	5.62	5.4233	2400.0	3
Basic phospholipase A2 PLA-A CHEMBL5022	IC50	5.6	5.6	2500.0	1
Basic phospholipase A2 1 CHEMBL3967	IC50	5.54	5.54	2900.0	1
B16 CHEMBL381	IC50	5.51	5.51	3100.0	1
HT-29 CHEMBL384	IC50	5.46	4.81	3500.0	4
Receptor-type tyrosine-protein phosphatase F CHEMBL3521	IC50	5.42	5.42	3800.0	1
Trypanosoma cruzi CHEMBL368	IC50	5.4	5.4	4000.0	2
Aldo-keto reductase family 1 member B10 CHEMBL5983	IC50	5.4	5.4	4000.0	1
Trypanosoma brucei CHEMBL612849	IC50	5.4	5.4	4000.0	1
NCI-N87 CHEMBL614197	IC50	5.38	5.38	4200.0	1
H9 CHEMBL614806	EC50	5.36	5.36	4400.0	1
DNA polymerase beta CHEMBL4343	IC50	5.32	5.195	4800.0	2
MDA-MB-231 CHEMBL400	IC50	5.23	4.7467	5900.0	3
MCF7 CHEMBL387	IC50	5.18	4.635	6600.0	8
Ubiquitin carboxyl-terminal hydrolase 7 CHEMBL2157850	IC50	5.16	5.16	7000.0	2
Low molecular weight phosphotyrosine protein phosphatase CHEMBL4903	IC50	5.14	5.05	7200.0	2
Protease CHEMBL2366517	IC50	5.1	5.1	8000.0	1
CAPAN-1 CHEMBL614536	IC50	5.07	5.07	8600.0	1
L02 CHEMBL4296457	IC50	5.05	4.64	8850.0	2
Glycogen phosphorylase, muscle form CHEMBL4696	IC50	5.05	4.9925	8912.5	4
NON-PROTEIN TARGET CHEMBL3879801	IC50	5.04	4.647	9100.0	10
THP-1 CHEMBL614245	IC50	5.04	5.04	9100.0	1
HL-60 CHEMBL383	IC50	5.02	4.85	9500.0	2
Z-138 CHEMBL4483276	IC50	5.01	5.01	9800.0	1
K562 CHEMBL385	IC50	4.99	4.69	10200.0	2
MIA PaCa-2 CHEMBL614725	IC50	4.98	4.98	10400.0	1
HT-29 CHEMBL384	EC50	4.97	4.97	10600.0	5
HepG2 CHEMBL395	IC50	4.96	4.4582	10840.0	11
Solute carrier organic anion transporter family member 1B3 CHEMBL1743121	IC50	4.94	4.94	11481.5	1
A549 CHEMBL392	IC50	4.94	4.5	11400.0	11
Lu1 CHEMBL613290	IC50	4.94	4.94	11500.0	1

Pharmacokinetic Data

Parameter	Value	Units	Species
AUC	114.3	ng.hr.mL-1	Rattus norvegicus
AUC	0.6	ng.hr.mL-1	Rattus norvegicus
Cmax	0.378	ug.mL-1	Rattus norvegicus
Cmax	0.0019	ug.mL-1	Rattus norvegicus
F	0.01	%	Rattus norvegicus
Ka	1.3	10^4/M	Homo sapiens
T1/2	1.55	hr	Rattus norvegicus
T1/2	0.3	hr	Rattus norvegicus
Tmax	0.08	hr	Rattus norvegicus
Tmax	0.25	hr	Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
Nuclear receptor ROR-gamma	IC50	=	0.75	nM	9.12	Binding affinity to yeast GAL4 DNA-binding domain fused human RORgammaT measured...	37172324
Unchecked	IC50	=	2.5	nM	8.6	Inhibitory activity against group II Phospholipase A2 (PLA2) from Vipera russell...	15203142
Sentrin-specific protease 1	IC50	=	6.4	nM	8.19	Inhibition of SENP1 (unknown origin)	35247754
Human immunodeficiency virus 1	EC50	=	10.0	nM	8.0	Antiviral activity against HIV-1 3B	31499360
Transcription factor p65	IC50	=	31.0	nM	7.51	Inhibition of biotinylated consensus sequence binding to NF-kB p65 in human HeLa...	30057155
Liver carboxylesterase 1	IC50	=	100.0	nM	7.0	Inhibition of CES1A1 in human liver microsomes using D-luciferin methyl ester as...	32951423
Nuclear receptor ROR-gamma	IC50	=	130.0	nM	6.89	Antagonist activity at Gal4-fused RORgamma (unknown origin) expressed in 293T ce...	24704616
Nuclear receptor ROR-gamma	IC50	=	680.0	nM	6.17	Inhibition of human GST-tagged ROR gamma LBD (amino acids 250 to 518)/LxxLL moti...	-
Streptococcus	EC50	=	880.0	nM	6.06	PUBCHEM_BIOASSAY: Luminescence Microorganism-Based Dose Response HTS to Identify...	-
Unchecked	Ki	=	900.0	nM	6.05	Metabolic Measurements: Glucose in tail blood was measured using a glucometer (O...	-
Streptococcus sp. 'group A'	EC50	=	949.0	nM	6.02	PUBCHEM_BIOASSAY: Luminescence Microorganism-Based Dose Confirmation HTS to Iden...	-
Toxoplasma gondii	IC50	=	1000.0	nM	6.0	Antimicrobial activity against Toxoplasma gondii	20185316
Nuclear receptor ROR-gamma	IC50	=	1060.0	nM	5.97	Antagonist activity at full-length RORgamma (unknown origin) expressed in 293T c...	24704616
G-protein coupled bile acid receptor 1	EC50	=	1100.0	nM	5.96	Agonist activity at TGR5 (unknown origin) expressed in CHO cells assessed as act...	38691888
Unchecked	IC50	=	1460.0	nM	5.84	Inhibition of transglutaminase in human keratinocytes in presence of 10 uM retin...	-
G-protein coupled bile acid receptor 1	EC50	=	1430.0	nM	5.84	Agonist activity at TGR5 expressed in CHO cells by CRE-driven luciferase reporte...	19911773
ADMET	IC50	=	1800.0	nM	5.75	Cytotoxicity against human WI 38 cells after 48 hrs by WST-8 assay	15730243
Streptokinase A	EC50	=	1790.0	nM	5.75	PUBCHEM_BIOASSAY: Luminescence Microorganism-Based Dose Confirmation HTS to Iden...	-
Unchecked	IC50	=	1780.0	nM	5.75	Inhibition of alpha-glucosidase (unknown origin) using PNPG as substrate incubat...	-
11-beta-hydroxysteroid dehydrogenase 1	IC50	=	1900.0	nM	5.72	Inhibition of human recombinant 11beta-HSD1 expressed in HEK293 cells assessed a...	20100662

Literature References

PubMed	DOI	Target Context	# Activities
-	10.1016/j.indcrop.2012.12.038	Spodoptera frugiperda	51
21648406	10.1021/np200060p	Unchecked	39
21855333	10.1016/j.bmcl.2011.07.095	Peroxisome proliferator-activated receptor alpha	18
20943386	10.1016/j.bmcl.2010.09.073	Unchecked	17
28073673	10.1016/j.bmcl.2016.12.071	HL-60	16
-	10.1007/s00044-012-0449-4	Mus musculus	14
31836444	10.1016/j.bmcl.2019.126858	Mus musculus	14
27020521	10.1016/j.bmcl.2016.03.061	Trichomonas vaginalis	14
27769622	10.1016/j.bmcl.2016.10.008	ADMET	9
21923134	10.1021/np2005133	Erythrocyte	8
21309591	10.1021/np1008202	Molecular identity unknown	8
21855333	10.1016/j.bmcl.2011.07.095	HepG2	7
21561086	10.1021/np200118q	Aldo-keto reductase family 1 member B10	7
23124210	10.1016/j.ejmech.2012.08.048	MGC-803	7
19716700	10.1016/j.bmcl.2009.08.048	HepG2	6
25794790	10.1016/j.ejmech.2015.01.015	Bacillus spizizenii	6
31771799	10.1016/j.bmc.2019.115152	HCT-116	6
28218000	10.1021/acs.jnatprod.6b01141	Neutrophil	6
-	10.1016/j.indcrop.2012.12.038	Drosophila melanogaster	5
27484517	10.1016/j.ejmech.2016.07.045	NON-PROTEIN TARGET	5

Data from ChEMBL 36 via Core Engine