Compound Detail

CHEMBL289191

LUPEOL

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C=C(C)[C@@H]1CC[C@]2(C)CC[C@]3(C)[C@H](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	CHEMBL289191
Name	LUPEOL
Phase	Preclinical
Structure Type	MOL
InChI Key	MQYXUWHLBZFQQO-QGTGJCAVSA-N

Targets

Activities

Assay Types

PK Parameters

Publications

Known Names

Molecular Properties

426.7

MW (Da)

8.02

ALogP

HBA

HBD

20.2

PSA (Å²)

0.42

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	C30H50O
MW	426.73
Aromatic Rings	0
Heavy Atoms	31
NP-Likeness	3.05

Activity Summary

IC50 21 meas. best 7.0

EC50 2 meas. best 5.01

Ki 2 meas. best 5.82

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
Liver carboxylesterase 1 CHEMBL2265	IC50	7.0	7.0	100.0	1
Tyrosine-protein phosphatase non-receptor type 1 CHEMBL335	IC50	6.25	5.84	560.0	2
Unchecked CHEMBL612545	Ki	5.82	5.82	1500.0	1
Cocaine esterase CHEMBL3180	IC50	5.72	5.72	1900.0	1
Tyrosine-protein phosphatase non-receptor type 1 CHEMBL335	Ki	5.6	5.6	2500.0	1
Caenorhabditis elegans CHEMBL613135	IC50	5.3	5.3	5000.0	1
dengue virus type 2 CHEMBL613966	EC50	5.01	5.01	9770.0	1
DNA topoisomerase 2-alpha CHEMBL1806	IC50	4.98	4.98	10400.0	1
MIA PaCa-2 CHEMBL614725	IC50	4.6	4.6	25180.0	1
BHY CHEMBL1075399	IC50	4.6	4.6	25180.0	1
COLO 205 CHEMBL614561	IC50	4.6	4.6	25180.0	1
A549 CHEMBL392	IC50	4.6	4.6	25180.0	1
MCF7 CHEMBL387	IC50	4.6	4.6	25180.0	1
Plasmodium falciparum CHEMBL364	IC50	4.55	4.28	28000.0	2
NON-PROTEIN TARGET CHEMBL3879801	IC50	4.46	4.46	34500.0	1
RAW264.7 CHEMBL612557	IC50	4.43	4.43	37300.0	2
B16 CHEMBL381	IC50	4.42	4.42	38000.0	1
Trypanosoma brucei brucei CHEMBL612851	IC50	4.34	4.34	45300.0	1
Haemonchus contortus CHEMBL613144	IC50	4.3	4.3	50000.0	1

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
Liver carboxylesterase 1	IC50	=	100.0	nM	7.0	Inhibition of CES1A1 in human liver microsomes using D-luciferin methyl ester as...	32951423
Tyrosine-protein phosphatase non-receptor type 1	IC50	=	560.0	nM	6.25	Inhibition of PTP1B (unknown origin)	34246920
Unchecked	Ki	=	1500.0	nM	5.82	Metabolic Measurements: Glucose in tail blood was measured using a glucometer (O...	-
Cocaine esterase	IC50	=	1900.0	nM	5.72	Inhibition of CES2A1 in human liver microsomes using D-luciferin methyl ester as...	32951423
Tyrosine-protein phosphatase non-receptor type 1	Ki	=	2500.0	nM	5.6	Metabolic Measurements: Glucose in tail blood was measured using a glucometer (O...	-
Tyrosine-protein phosphatase non-receptor type 1	IC50	=	3680.0	nM	5.43	Inhibition of recombinant human GST-tagged PTP1B catalytic domain expressed in E...	29064696
Caenorhabditis elegans	IC50	=	5000.0	nM	5.3	Nematocidal activity against Caenorhabditis elegans	28231520
dengue virus type 2	EC50	=	9770.0	nM	5.01	Antiviral activity against DENV2 infected in monkey LLC-MK2 cells	31128447
DNA topoisomerase 2-alpha	IC50	=	10400.0	nM	4.98	Inhibition of human 1 unit topoisomerase 2alpha catalytic activity assessed as r...	11754608
MIA PaCa-2	IC50	=	25180.0	nM	4.6	Antiproliferative activity against human MIAPaCa2 cells assessed as reduction in...	31784199
COLO 205	IC50	=	25180.0	nM	4.6	Antiproliferative activity against human COLO205 cells assessed as reduction in ...	31784199
A549	IC50	=	25180.0	nM	4.6	Antiproliferative activity against human A549 cells assessed as reduction in cel...	31784199
BHY	IC50	=	25180.0	nM	4.6	Antiproliferative activity against human BHY cells assessed as reduction in cell...	31784199
MCF7	IC50	=	25180.0	nM	4.6	Antiproliferative activity against human MCF7 cells assessed as reduction in cel...	31784199
Plasmodium falciparum	IC50	=	28000.0	nM	4.55	Antimicrobial activity against Plasmodium falciparum	20185316
NON-PROTEIN TARGET	IC50	=	34500.0	nM	4.46	Antiinflammatory activity in mouse J774A1 cells assessed as inhibition of LPS-in...	24909081
RAW264.7	IC50	=	37300.0	nM	4.43	Antiinflammatory activity in mouse RAW264.7 cells assessed as inhibition of LPS-...	24909081
RAW264.7	IC50	=	37300.0	nM	4.43	Cytotoxicity against mouse RAW264.7 cells assessed as reduction in cell viabilit...	38107170
B16	IC50	=	38000.0	nM	4.42	Growth inhibition of mouse B16 2F2 cells after 3 days	12027734
Trypanosoma brucei brucei	IC50	=	45300.0	nM	4.34	Antitrypanosomal activity against Trypanosoma brucei brucei bloodstream trypomas...	17637068

Literature References

PubMed	DOI	Target Context	# Activities
18717586	10.1021/np0703141	Rattus norvegicus	32
25325613	10.1021/np500296b	Mus musculus	20
26592171	10.1016/j.bmcl.2015.10.035	LLC-PK1	8
26878936	10.1021/acs.jnatprod.5b01088	Molecular identity unknown	6
19515563	10.1016/j.bmcl.2009.05.034	Syrian golden hamster	6
11754608	10.1021/np010176u	DNA topoisomerase 2-alpha	6
26878936	10.1021/acs.jnatprod.5b01088	Mus musculus	5
27002382	10.1021/acs.jnatprod.6b00027	Keratinocyte	4
24467317	10.1021/np400851k	NON-PROTEIN TARGET	4
16441070	10.1021/np050315y	Plasmodium falciparum	4
21546135	10.1016/j.ejmech.2011.04.025	Mycobacterium tuberculosis	3
26592171	10.1016/j.bmcl.2015.10.035	Unchecked	3
27002382	10.1021/acs.jnatprod.6b00027	Fibroblast	3
26878936	10.1021/acs.jnatprod.5b01088	Calvarial osteoblast	3
20542692	10.1016/j.bmcl.2010.05.061	Mycobacterium tuberculosis	2
-	10.1007/s00044-012-0183-y	Neutrophil	2
19285391	10.1016/j.bmcl.2009.02.076	ADMET	2
15270571	10.1021/np040027m	Aspergillus niger	2
-	10.1007/s00044-012-0183-y	PBL	2
22462772	10.1021/np200910u	Unchecked	2

Data from ChEMBL 36 via Core Engine