Compound Detail

CHEMBL295316

PLUMBAGIN

Phase I

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Phase I

CC1=CC(=O)c2c(O)cccc2C1=O

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL295316
Name	PLUMBAGIN
Phase	Phase I
Structure Type	MOL
InChI Key	VCMMXZQDRFWYSE-UHFFFAOYSA-N

Known Names

NSC-236613 NSC-688284 Pcur-101 Plumbagin

Targets

114

Activities

Assay Types

PK Parameters

Publications

Known Names

Indications

Molecular Properties

188.2

MW (Da)

1.72

ALogP

HBA

HBD

54.4

PSA (Å²)

0.67

QED

Ro5 Violations

Rot. Bonds

Drug Information

Molecule Type	Small molecule
Chirality	Achiral

Flags

Natural Product

Extended Properties

Molecular Formula	C11H8O3
MW	188.18
Aromatic Rings	1
Heavy Atoms	14
NP-Likeness	1.77

Indications

Prostatic Neoplasms, Castration-Resistant

Activity Summary

IC50 104 meas. best 7.22

EC50 5 meas. best 6.34

Kd 3 meas. best 5.7

Ki 2 meas. best 5.63

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
Thiosulfate sulfurtransferase CHEMBL4295835	IC50	7.22	7.22	60.0	1
Plasmodium falciparum CHEMBL364	IC50	6.57	6.57	270.0	1
GroEL/GroES CHEMBL4106139	IC50	6.54	5.98	290.0	2
Transient receptor potential cation channel subfamily A member 1 CHEMBL6007	EC50	6.34	6.34	460.0	1
M-phase inducer phosphatase 1 CHEMBL3775	IC50	6.16	6.16	700.0	1
BT-474 CHEMBL614529	IC50	6.1	5.925	800.0	2
PBMC CHEMBL613107	EC50	6.1	6.1	800.0	1
NON-PROTEIN TARGET CHEMBL3879801	EC50	6.1	6.1	800.0	1
Jurkat CHEMBL397	IC50	6.02	6.02	950.0	1
MCF7 CHEMBL387	IC50	6.0	5.4231	1000.0	13
Unchecked CHEMBL612545	IC50	6.0	5.3683	1000.0	6
NON-PROTEIN TARGET CHEMBL3879801	IC50	6.0	5.265	1000.0	4
HL-60 CHEMBL383	IC50	5.96	5.5725	1100.0	4
THP-1 CHEMBL614245	IC50	5.96	5.96	1100.0	1
Trypanosoma cruzi CHEMBL368	IC50	5.86	5.86	1380.0	1
MDA-MB-231 CHEMBL400	IC50	5.82	4.9913	1500.0	8
SK-BR-3 CHEMBL613834	IC50	5.75	5.625	1800.0	2
Histone acetyltransferase p300 CHEMBL3784	IC50	5.7	5.1	2000.0	5
Histone acetyltransferase p300 CHEMBL3784	Kd	5.7	5.7	2000.0	1
Cytochrome P450 1A2 CHEMBL3356	Ki	5.63	5.63	2360.0	1
U-937 CHEMBL612794	IC50	5.62	5.62	2400.0	1
Cytochrome P450 1A2 CHEMBL3356	IC50	5.61	5.61	2460.0	1
SMMC-7721 CHEMBL613831	IC50	5.61	5.1067	2430.0	3
MDA-MB-468 CHEMBL614335	IC50	5.6	5.6	2500.0	1
Cytochrome P450 1A1 CHEMBL2231	Ki	5.59	5.59	2560.0	1
MONO-MAC-6 CHEMBL2366062	IC50	5.58	5.58	2600.0	1
PBMC CHEMBL613107	IC50	5.57	5.57	2700.0	1
Cytochrome P450 1A1 CHEMBL2231	IC50	5.56	5.56	2770.0	1
A549 CHEMBL392	IC50	5.52	5.155	3000.0	4
SAS CHEMBL1075569	IC50	5.52	5.52	3000.0	1
M-phase inducer phosphatase 2 CHEMBL4804	IC50	5.51	5.51	3100.0	1
MCF7/PTX CHEMBL4483255	IC50	5.46	5.46	3500.0	1
SW982 CHEMBL2366238	IC50	5.44	5.44	3600.0	1
ACHN CHEMBL614519	EC50	5.43	5.285	3700.0	2
HT-29 CHEMBL384	IC50	5.38	4.8467	4190.0	3
SK-MEL-28 CHEMBL614919	IC50	5.3	5.3	5000.0	1
DU-145 CHEMBL613508	IC50	5.28	5.28	5230.0	1
Cytochrome P450 1B1 CHEMBL4878	IC50	5.21	5.21	6150.0	1
HSP60/HSP10 CHEMBL4106131	IC50	5.2	5.2	6300.0	1
SW480 CHEMBL612544	IC50	5.14	5.03	7300.0	2
SW-620 CHEMBL612262	IC50	5.13	5.12	7400.0	2
HepG2 CHEMBL395	IC50	5.04	5.005	9170.0	2
HCT-116 CHEMBL394	IC50	5.01	4.8033	9800.0	3
KB CHEMBL398	IC50	5.01	5.01	9830.0	1
LS174T CHEMBL614097	IC50	5.0	5.0	9900.0	1
HeLa CHEMBL399	IC50	4.99	4.51	10200.0	4
Dual specificity mitogen-activated protein kinase kinase 7 CHEMBL3530	Kd	4.85	4.85	14000.0	1
WRL68 CHEMBL612587	IC50	4.81	4.81	15360.0	1
Cell division protein FtsZ CHEMBL2417349	Kd	4.8	4.8	15800.0	1
PC-3 CHEMBL390	IC50	4.76	4.76	17190.0	2

Pharmacokinetic Data

Parameter	Value	Units	Species
F	38.0	%	Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
Thiosulfate sulfurtransferase	IC50	=	60.0	nM	7.22	Inhibition of native rhodanese (unknown origin) assessed as reduction in rhodane...	30852084
Plasmodium falciparum	IC50	=	270.0	nM	6.57	Antimalarial activity against Plasmodium falciparum	19299148
GroEL/GroES	IC50	=	290.0	nM	6.54	Inhibition of Escherichia coli GroEL expressed in Escherichia coli DH5alpha/Esch...	30852084
Transient receptor potential cation channel subfamily A member 1	EC50	=	460.0	nM	6.34	Activation of human TRPA1 expressed in HEK293 cells assessed as increase in calc...	26905390
M-phase inducer phosphatase 1	IC50	=	700.0	nM	6.16	Inhibition of recombinant Cdc25A (unknown origin) using OMFP as substrate measur...	31563013
NON-PROTEIN TARGET	EC50	=	800.0	nM	6.1	Cytotoxicity against human INA-6 cells assessed as viable fractions using annexi...	22019229
PBMC	EC50	=	800.0	nM	6.1	Cytotoxicity against human PBMC cells assessed as viable fractions using annexin...	22019229
BT-474	IC50	=	800.0	nM	6.1	Cytotoxicity against Her2-overexpressing human BT474 cells after 72 hrs by MTT a...	22512718
Jurkat	IC50	=	950.0	nM	6.02	Cytotoxicity against human Jurkat cells assessed as reduction in cell viability ...	31563013
NON-PROTEIN TARGET	IC50	=	1000.0	nM	6.0	Growth inhibition of mouse B16F10 cells by MTT assay	26706169
MCF7	IC50	=	1000.0	nM	6.0	Cytotoxicity against human MCF7 cells incubated for 7 days by MTT assay	38458106
Unchecked	IC50	=	1000.0	nM	6.0	Cytotoxicity against human MCF7/LCC2 cells incubated for 7 days by MTT assay	38458106
Unchecked	IC50	=	1000.0	nM	6.0	Cytotoxicity against human MCF7/LCC9 cells incubated for 7 days by MTT assay	38458106
THP-1	IC50	=	1100.0	nM	5.96	Cytotoxicity against human THP1 cells assessed as reduction in cell viability in...	31563013
HL-60	IC50	=	1100.0	nM	5.96	Cytotoxicity against human HL60 cells assessed as reduction in cell viability in...	31563013
Trypanosoma cruzi	IC50	=	1380.0	nM	5.86	Antitrypanosomal activity against bloodstream forms of Trypanosoma cruzi Y isola...	28521262
HL-60	IC50	=	1500.0	nM	5.82	Cytotoxicity against human HL-60 cells assessed as reduction in cell viability i...	38458106
MDA-MB-231	IC50	=	1500.0	nM	5.82	Antiproliferative activity against human MDA-MB-231 cells assessed as inhibition...	38458106
MCF7	IC50	=	1500.0	nM	5.82	Antiproliferative activity against human MCF7 cells assessed as inhibition of ce...	38458106
BT-474	IC50	=	1800.0	nM	5.75	Cytotoxicity against Her2-overexpressing human BT474 cells after 24 hrs by MTT a...	22512718

Literature References

PubMed	DOI	Target Context	# Activities
23742275	10.1021/np3008792	Mus musculus	15
24828199	10.1021/np4010085	Unchecked	15
22512718	10.1021/np3000409	SK-BR-3	14
22512718	10.1021/np3000409	BT-474	12
23110447	10.1021/np300611r	Erythrocyte	11
30810041	10.1021/acs.jnatprod.8b00964	Mitogen-activated protein kinase; ERK1/ERK2	10
28359791	10.1016/j.bmcl.2017.03.047	Unchecked	9
26905390	10.1021/acs.jnatprod.5b00396	Transient receptor potential cation channel subfamily A member 1	8
28359791	10.1016/j.bmcl.2017.03.047	A549	8
12502328	10.1021/np010599w	Staphylococcus aureus	6
24355130	10.1016/j.bmcl.2013.11.064	MCF7	6
24828199	10.1021/np4010085	SW480	6
12502328	10.1021/np010599w	Enterococcus faecalis	6
24828199	10.1021/np4010085	HCT-116	6
30810041	10.1021/acs.jnatprod.8b00964	MCF7	5
-	10.1016/j.cropro.2011.09.009	Trichoplusia ni	5
11170645	10.1021/jm001079l	Unchecked	5
24828199	10.1021/np4010085	SW-620	5
11170645	10.1021/jm001079l	ADMET	4
27189886	10.1016/j.bmc.2016.05.003	Unchecked	4

Data from ChEMBL 36 via Core Engine