Compound Detail

CHEMBL507237

CUCURBITACIN B

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CC(=O)OC(C)(C)/C=C/C(=O)[C@](C)(O)[C@H]1[C@H](O)C[C@@]2(C)[C@@H]3CC=C4[C@H](C[C@H](O)C(=O)C4(C)C)[C@]3(C)C(=O)C[C@]12C

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL507237
Name	CUCURBITACIN B
Phase	Preclinical
Structure Type	MOL
InChI Key	IXQKXEUSCPEQRD-QATBOUOLSA-N

Targets

Activities

Assay Types

PK Parameters

Publications

Known Names

Molecular Properties

558.7

MW (Da)

3.50

ALogP

HBA

HBD

138.2

PSA (Å²)

0.26

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	C32H46O8
MW	558.71
Aromatic Rings	0
Heavy Atoms	40
NP-Likeness	3.06

Activity Summary

IC50 17 meas. best 8.1

EC50 2 meas. best 7.7

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
Bel-7402 CHEMBL614279	IC50	8.1	8.1	8.0	1
A549 CHEMBL392	IC50	8.0	6.655	10.0	4
NON-PROTEIN TARGET CHEMBL3879801	EC50	7.7	7.7	20.0	1
MCF7 CHEMBL387	IC50	7.38	6.745	41.3	2
Unchecked CHEMBL612545	IC50	7.21	7.21	61.0	1
Hypoxia-inducible factor 1-alpha CHEMBL4261	IC50	6.57	6.57	270.0	1
Integrin alpha-L CHEMBL1803	IC50	6.52	6.52	300.0	1
Hep 3B2 CHEMBL4296437	IC50	6.51	6.51	310.0	1
HepG2 CHEMBL395	IC50	6.12	5.34	760.0	2
HeLa CHEMBL399	IC50	6.1	6.1	800.0	1
Signal transducer and activator of transcription 3 CHEMBL4026	IC50	5.52	5.52	3000.0	1
ADMET CHEMBL612558	IC50	5.36	5.36	4420.0	1
CAKI-1 CHEMBL614067	IC50	5.15	5.15	7100.0	1
HepG2 CHEMBL395	EC50	4.98	4.98	10500.0	1

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
Bel-7402	IC50	=	8.0	nM	8.1	Cytotoxicity against human Bel7402 cells after 72 hrs by SRB assay	19348465
A549	IC50	=	10.0	nM	8.0	Cytotoxicity against human A549 cells after 72 hrs by SRB assay	19348465
NON-PROTEIN TARGET	EC50	=	20.0	nM	7.7	Antiproliferative activity against serum-stimulated rat HSC-T6 cells after 24 hr...	21459003
A549	IC50	=	40.0	nM	7.4	Cytotoxicity against human A549 cells after 72 hrs by MTT assay	22472043
MCF7	IC50	=	41.3	nM	7.38	Cytotoxicity against human MCF7 cells assessed as growth inhibition after 72 hrs...	25756299
Unchecked	IC50	=	61.0	nM	7.21	Inhibition of NF-kappaB activity in human HeLa cells by SEAP reporter assay	20469887
A549	IC50	=	130.0	nM	6.89	Cytotoxicity against human A549 cells after 48 hrs by MTT assay	22472043
Hypoxia-inducible factor 1-alpha	IC50	=	270.0	nM	6.57	Inhibition of hypoxia-induced HIF1alpha protein accumulation in human Hep3B cell...	20469887
Integrin alpha-L	IC50	=	300.0	nM	6.52	Inhibition of LFA1 expressed in human JY cells interaction with ICAM1-IG express...	7852999
Hep 3B2	IC50	=	310.0	nM	6.51	Inhibition of hypoxia-induced VEGF protein secretion in human Hep3B cells after ...	20469887
HepG2	IC50	=	760.0	nM	6.12	Cytotoxicity against human HepG2 cells after 24 hrs by MTT assay	15568769
MCF7	IC50	=	780.0	nM	6.11	Cytotoxicity against human MCF7 cells after 24 hrs by MTT assay	15568769
HeLa	IC50	=	800.0	nM	6.1	Cytotoxicity against human HeLa cells after 24 hrs by MTT assay	21459003
Signal transducer and activator of transcription 3	IC50	=	3000.0	nM	5.52	Inhibition of STAT3 by Western blotting	19348465
ADMET	IC50	=	4420.0	nM	5.36	Cytotoxicity against rat HSC-T6 cell after 24 hrs by MTT assay	21459003
CAKI-1	IC50	=	7100.0	nM	5.15	Cytotoxicity against human Caki1 cells after 24 hrs by MTT assay	15568769
HepG2	EC50	=	10500.0	nM	4.98	Hepatoprotective activity in human HepG2 cells assessed as inhibition of CCl4-in...	21459003
HepG2	IC50	=	27670.0	nM	4.56	Cytotoxicity against human HepG2 cells after 24 hrs assessed as inhibition of ce...	21459003
A549	IC50	=	46600.0	nM	4.33	Cytotoxicity against human A549 cells after 24 hrs by MTT assay	15568769

Literature References

PubMed	DOI	Target Context	# Activities
25756299	10.1021/acs.jnatprod.5b00054	Heat shock protein HSP90	7
21459003	10.1016/j.bmc.2011.01.037	HepG2	5
15332833	10.1021/np049953r	NON-PROTEIN TARGET	4
7852999	10.1021/np50113a004	JY	3
7852999	10.1021/np50113a004	Unchecked	3
22472043	10.1016/j.bmc.2012.03.001	A549	3
20347305	10.1016/j.bmcl.2010.02.062	Signal transducer and activator of transcription 3	2
20469887	10.1021/np900820p	Hypoxia-inducible factor 1-alpha	2
3404148	10.1021/np50057a008	Mus musculus	2
15568769	10.1021/np049883o	A549	1
19348465	10.1021/np800692t	A549	1
17190463	10.1021/np060213n	NCI-H460	1
15568769	10.1021/np049883o	MCF7	1
15568769	10.1021/np049883o	HepG2	1
15568769	10.1021/np049883o	CAKI-1	1
18088099	10.1021/np0704396	Human immunodeficiency virus 1	1
-	10.1021/np50014a012	Phytophthora cactorum	1
7852999	10.1021/np50113a004	Integrin alpha-L	1
11325234	10.1021/np0005006	KB	1
18088099	10.1021/np0704396	Unchecked	1

Data from ChEMBL 36 via Core Engine