Compound Detail

CHEMBL387737

CUCURBITACIN I

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CC(C)(O)/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(O)C(=O)C4(C)C)[C@]3(C)C(=O)C[C@]12C

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL387737
Name	CUCURBITACIN I
Phase	Preclinical
Structure Type	MOL
InChI Key	NISPVUDLMHQFRQ-MKIKIEMVSA-N

Targets

Activities

Assay Types

PK Parameters

Publications

Known Names

514.7

MW (Da)

3.62

ALogP

HBA

HBD

132.1

PSA (Å²)

0.33

QED

Ro5 Violations

Rot. Bonds

Natural Product First in Class Prodrug

IC50 9 meas. best 10.0

EC50 2 meas. best 7.7

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
HL-60 CHEMBL383	IC50	10.0	10.0	0.1	1
U-937 CHEMBL612794	IC50	9.52	9.52	0.3	1
HT-1080 CHEMBL614580	IC50	9.33	9.33	0.5	1
NON-PROTEIN TARGET CHEMBL3879801	EC50	7.7	7.7	20.0	1
MCF7 CHEMBL387	IC50	7.22	7.22	60.7	1
A549 CHEMBL392	IC50	6.85	6.85	140.0	1
HT-29 CHEMBL384	IC50	6.72	6.72	190.0	1
Integrin alpha-L CHEMBL1803	IC50	6.02	6.02	950.0	1
HepG2 CHEMBL395	EC50	5.5	5.5	3160.0	1
ADMET CHEMBL612558	IC50	5.44	5.44	3600.0	1
HepG2 CHEMBL395	IC50	4.8	4.8	15800.0	1

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
HL-60	IC50	=	0.1	nM	10.0	Cytotoxicity against human HL60 cells after 72 hrs by WST-8 assay	20347305
U-937	IC50	=	0.3	nM	9.52	Cytotoxicity against human U937 cells after 72 hrs by WST-8 assay	20347305
HT-1080	IC50	=	0.47	nM	9.33	Cytotoxicity against human HT1080 cells after 72 hrs by WST-8 assay	20347305
NON-PROTEIN TARGET	EC50	=	20.0	nM	7.7	Antiproliferative activity against serum-stimulated rat HSC-T6 cells after 24 hr...	21459003
MCF7	IC50	=	60.7	nM	7.22	Cytotoxicity against human MCF7 cells assessed as growth inhibition after 72 hrs...	25756299
A549	IC50	=	140.0	nM	6.85	Growth inhibition of human A549 cells	28814374
HT-29	IC50	=	190.0	nM	6.72	Cytotoxicity against human HT-29 cells after 3 days by sulforhodamine B assay	22239601
Integrin alpha-L	IC50	=	950.0	nM	6.02	Inhibition of LFA1 expressed in human JY cells interaction with ICAM1-IG express...	7852999
HepG2	EC50	=	3160.0	nM	5.5	Hepatoprotective activity in human HepG2 cells assessed as inhibition of CCl4-in...	21459003
ADMET	IC50	=	3600.0	nM	5.44	Cytotoxicity against rat HSC-T6 cell after 24 hrs by MTT assay	21459003
HepG2	IC50	=	15800.0	nM	4.8	Cytotoxicity against human HepG2 cells after 24 hrs assessed as inhibition of ce...	21459003

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
7852999	10.1021/np50113a004	JY	4
15332833	10.1021/np049953r	NON-PROTEIN TARGET	4
7852999	10.1021/np50113a004	Unchecked	3
20347305	10.1016/j.bmcl.2010.02.062	HT-1080	2
20347305	10.1016/j.bmcl.2010.02.062	LIM domain kinase 1/2	2
20347305	10.1016/j.bmcl.2010.02.062	HL-60	1
33269591	10.1021/acs.jnatprod.0c00364	Unchecked	1
21459003	10.1016/j.bmc.2011.01.037	Unchecked	1
21459003	10.1016/j.bmc.2011.01.037	HeLa	1
21459003	10.1016/j.bmc.2011.01.037	ADMET	1
21459003	10.1016/j.bmc.2011.01.037	NON-PROTEIN TARGET	1
20347305	10.1016/j.bmcl.2010.02.062	Cofilin-1	1
15615517	10.1021/jm049504o	Bifunctional purine biosynthesis protein ATIC	1
20347305	10.1016/j.bmcl.2010.02.062	U-937	1
7852999	10.1021/np50113a004	Integrin alpha-L	1
7852999	10.1021/np50113a004	Protein kinase C (PKC)	1
18088099	10.1021/np0704396	Unchecked	1
18088099	10.1021/np0704396	C8166	1

Data from ChEMBL 36 via Core Engine