Compound Detail

CHEMBL23236

BETULIN

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C=C(C)[C@@H]1CC[C@]2(CO)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	CHEMBL23236
Name	BETULIN
Phase	Preclinical
Structure Type	MOL
InChI Key	FVWJYYTZTCVBKE-ROUWMTJPSA-N

Targets

Activities

Assay Types

PK Parameters

Publications

Known Names

Molecular Properties

442.7

MW (Da)

7.00

ALogP

HBA

HBD

40.5

PSA (Å²)

0.45

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	C30H50O2
MW	442.73
Aromatic Rings	0
Heavy Atoms	32
NP-Likeness	3.23

Activity Summary

IC50 64 meas. best 6.16

EC50 13 meas. best 5.7

Ki 2 meas. best 5.7

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
Human alphaherpesvirus 1 CHEMBL377	IC50	6.16	6.105	700.0	2
ADMET CHEMBL612558	IC50	5.85	5.5425	1400.0	4
Unchecked CHEMBL612545	Ki	5.7	5.7	2000.0	1
Human betaherpesvirus 5 CHEMBL371	EC50	5.7	5.7	1990.0	1
Tyrosine-protein phosphatase non-receptor type 1 CHEMBL335	Ki	5.52	5.52	3000.0	1
A549 CHEMBL392	IC50	5.42	5.044	3800.0	5
Plasmodium falciparum CHEMBL364	EC50	5.41	5.41	3938.0	1
A2780 CHEMBL614004	IC50	5.21	5.21	6100.0	1
DLD-1 CHEMBL614285	IC50	5.18	5.18	6600.0	3
Transcription factor p65 CHEMBL5533	IC50	5.06	5.06	8800.0	1
Trypanosoma brucei brucei CHEMBL612851	IC50	5.05	5.05	8900.0	1
Human alphaherpesvirus 2 CHEMBL370	IC50	5.03	5.03	9400.0	1
HepG2 CHEMBL395	IC50	4.97	4.97	10700.0	1
Unchecked CHEMBL612545	EC50	4.96	4.96	11000.0	1
HeLa CHEMBL399	IC50	4.91	4.91	12200.0	1
K562 CHEMBL385	IC50	4.89	4.89	12890.0	1
Human immunodeficiency virus 1 CHEMBL378	IC50	4.86	4.86	13800.0	1
NON-PROTEIN TARGET CHEMBL3879801	IC50	4.77	4.5633	17000.0	3
Glycogen phosphorylase, muscle form CHEMBL4696	IC50	4.77	4.6725	16982.4	4
PC-3 CHEMBL390	IC50	4.75	4.7	17900.0	2
MCF7 CHEMBL387	IC50	4.71	4.5667	19300.0	3
A549 CHEMBL392	EC50	4.69	4.69	20600.0	1
WI-38 VA13 CHEMBL612807	IC50	4.69	4.69	20300.0	1
T47D CHEMBL614361	IC50	4.68	4.68	20720.0	1
H9 CHEMBL614806	EC50	4.64	4.64	23000.0	2
Human immunodeficiency virus 1 CHEMBL378	EC50	4.64	4.64	23000.0	3
5'-nucleotidase CHEMBL5957	IC50	4.64	4.64	22660.0	2
MDA-MB-231 CHEMBL400	IC50	4.61	4.315	24570.0	2
MCF7 CHEMBL387	EC50	4.61	4.61	24400.0	1
Bcap37 CHEMBL613842	IC50	4.59	4.59	25500.0	1
L02 CHEMBL4296457	IC50	4.57	4.57	26820.0	1
ECa-109 cell line CHEMBL614668	IC50	4.57	4.57	26640.0	1
B16 CHEMBL381	IC50	4.56	4.56	27400.0	1
A-375 CHEMBL613859	IC50	4.55	4.55	28000.0	1
NON-PROTEIN TARGET CHEMBL3879801	EC50	4.54	4.54	28800.0	1
A2780 CHEMBL614004	EC50	4.53	4.53	29300.0	1
MGC-803 CHEMBL3706566	IC50	4.52	4.52	30200.0	1
HL-60 CHEMBL383	IC50	4.51	4.51	30940.0	1
DNA topoisomerase 2-alpha CHEMBL1806	IC50	4.41	4.41	38600.0	1
H9 CHEMBL614806	IC50	4.36	4.3567	43700.0	3
Semliki Forest virus CHEMBL613724	IC50	4.34	4.34	45500.0	2
Ectonucleoside triphosphate diphosphohydrolase 1 CHEMBL4739681	IC50	4.3	4.3	49760.0	1
5'-nucleotidase CHEMBL4680034	IC50	4.3	4.3	50320.0	1
CCRF-CEM CHEMBL382	IC50	4.29	4.29	50800.0	1
Unchecked CHEMBL612545	IC50	4.28	4.28	52500.0	1
ADR5000 cell line CHEMBL614266	IC50	4.25	4.25	56500.0	1
J774 CHEMBL614123	IC50	4.17	4.17	67100.0	1
MIA PaCa-2 CHEMBL614725	IC50	4.02	4.02	95000.0	1

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
Human alphaherpesvirus 1	IC50	=	700.0	nM	6.16	Antiviral activity against HSV-1 KOS infected in African green monkey RC-37 cell...	26112446
Human alphaherpesvirus 1	IC50	=	900.0	nM	6.05	Antiviral activity against HSV-1 F infected in African green monkey Vero cells a...	26112446
ADMET	IC50	=	1400.0	nM	5.85	Cytotoxicity against human WI 38 cells after 48 hrs by WST-8 assay	15730243
Human betaherpesvirus 5	EC50	=	1990.0	nM	5.7	Antiviral activity against recombinant HCMV AD169 expressing GFP infected in hum...	30503412
Unchecked	Ki	=	2000.0	nM	5.7	Metabolic Measurements: Glucose in tail blood was measured using a glucometer (O...	-
Tyrosine-protein phosphatase non-receptor type 1	Ki	=	3000.0	nM	5.52	Metabolic Measurements: Glucose in tail blood was measured using a glucometer (O...	-
ADMET	IC50	=	3600.0	nM	5.44	Cytotoxicity against human WS1 cells after 48 hrs	19115839
ADMET	IC50	=	3600.0	nM	5.44	Cytotoxicity against human WS1 cells after 48 hrs by resazurin reduction test	19200744
ADMET	IC50	=	3600.0	nM	5.44	Cytotoxicity against human WS1 cells by resazurin reduction test	19285391
A549	IC50	=	3800.0	nM	5.42	Cytotoxicity against human A549 cells after 48 hrs	19115839
A549	IC50	=	3800.0	nM	5.42	Cytotoxicity against human A549 cells after 48 hrs by resazurin reduction test	19200744
A549	IC50	=	3800.0	nM	5.42	Cytotoxicity against human A549 cells by resazurin reduction test	19285391
Plasmodium falciparum	EC50	=	3938.0	nM	5.41	Antimalarial activity against ring stage Plasmodium falciparum 3D7 infected in t...	30503412
A2780	IC50	=	6100.0	nM	5.21	Cytotoxicity against human A2780 cells after 4 days by MTT assay	19702283
DLD-1	IC50	=	6600.0	nM	5.18	Cytotoxicity against human DLD1 cells by resazurin reduction test	19285391
DLD-1	IC50	=	6600.0	nM	5.18	Cytotoxicity against human DLD1 cells after 48 hrs by resazurin reduction test	19200744
DLD-1	IC50	=	6600.0	nM	5.18	Cytotoxicity against human DLD1 cells after 48 hrs	19115839
Transcription factor p65	IC50	=	8800.0	nM	5.06	Inhibition of biotinylated consensus sequence binding to NF-kB p65 in human HeLa...	30057155
Trypanosoma brucei brucei	IC50	=	8900.0	nM	5.05	Antitrypanosomal activity against Trypanosoma brucei brucei bloodstream trypomas...	17637068
Human alphaherpesvirus 2	IC50	=	9400.0	nM	5.03	Antiviral activity against HSV-2 G infected in African green monkey Vero cells a...	26112446

Literature References

PubMed	DOI	Target Context	# Activities
27002382	10.1021/acs.jnatprod.6b00027	Keratinocyte	163
27002382	10.1021/acs.jnatprod.6b00027	Fibroblast	150
27002382	10.1021/acs.jnatprod.6b00027	Molecular identity unknown	40
32334913	10.1016/j.bmcl.2020.127193	BV-2	11
36857482	10.1021/acs.jnatprod.2c01019	HeLa	7
36857482	10.1021/acs.jnatprod.2c01019	L929	7
26915998	10.1021/acs.jnatprod.5b00709	J774	5
2832544	10.1021/np50054a031	Unchecked	5
28782948	10.1021/acs.jnatprod.7b00105	PC-3	4
19560351	10.1016/j.bmcl.2009.06.046	Unchecked	4
-	10.6019/CHEMBL4495565	SARS-CoV-2	4
24467317	10.1021/np400851k	NON-PROTEIN TARGET	4
19560351	10.1016/j.bmcl.2009.06.046	NON-PROTEIN TARGET	4
2832544	10.1021/np50054a031	Raji	4
19200744	10.1016/j.bmc.2009.01.022	ADMET	3
11754608	10.1021/np010176u	DNA topoisomerase 2-alpha	3
19839605	10.1021/np9003245	Semliki Forest virus	3
26112446	10.1016/j.bmcl.2015.05.099	Unchecked	3
22462772	10.1021/np200910u	Unchecked	2
19839605	10.1021/np9003245	ADMET	2

Data from ChEMBL 36 via Core Engine