Compound Detail

CHEMBL64130

NAPABUCASIN

🧪 Phase III

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🧪 Phase III

CC(=O)c1cc2c(o1)C(=O)c1ccccc1C2=O

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL64130
Name	NAPABUCASIN
Phase	Phase III
Structure Type	MOL
InChI Key	DPHUWDIXHNQOSY-UHFFFAOYSA-N

Known Names

2-acetylfuranonaphthoquinone 2-acetylfuro-1,4-naphthoquinone BBI-608 BBI608 Napabucasin Napabucasina Napabucasine

Targets

Activities

Assay Types

PK Parameters

Publications

Known Names

Indications

Mechanisms

Molecular Properties

240.2

MW (Da)

2.26

ALogP

HBA

HBD

64.3

PSA (Å²)

0.61

QED

Ro5 Violations

Rot. Bonds

Drug Information

Molecule Type	Small molecule
Chirality	Achiral

Flags

Natural Product

USAN Year

2014

Extended Properties

Molecular Formula	C14H8O4
MW	240.21
Aromatic Rings	2
Heavy Atoms	18
NP-Likeness	0.96

Mechanism of Action

Mechanism	Action Type	Target	Direct	Efficacy
Unknown	-	-	✓	✓

Indications

Carcinoma, Non-Small-Cell Lung Carcinoma, Pancreatic Ductal Colorectal Neoplasms Colorectal Neoplasms Carcinoma, Hepatocellular Glioblastoma Hematologic Neoplasms Neoplasms

Activity Summary

IC50 58 meas. best 7.64

EC50 4 meas. best 5.83

Kd 1 meas. best 4.89

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
DU-145 CHEMBL613508	IC50	7.64	7.64	23.0	1
A549 CHEMBL392	IC50	6.92	6.285	120.0	4
HT-29 CHEMBL384	IC50	6.85	6.1833	140.0	3
MCF7 CHEMBL387	IC50	6.62	5.92	240.0	3
MDA-MB-231 CHEMBL400	IC50	6.6	5.8778	250.0	9
HCT-116 CHEMBL394	IC50	6.52	6.365	300.0	2
Aldehyde dehydrogenase 1A1 CHEMBL3577	IC50	6.37	6.37	425.3	1
AGS CHEMBL613860	IC50	6.36	6.36	437.0	1
HaCaT CHEMBL614392	IC50	6.3	6.3	500.0	2
MCF-10A CHEMBL614321	IC50	6.27	5.685	540.0	2
HepG2 CHEMBL395	IC50	6.18	5.6075	660.0	4
HCT-15 CHEMBL612263	IC50	6.18	6.18	660.3	1
SW480 CHEMBL612544	IC50	6.12	6.12	762.7	1
MGC-803 CHEMBL3706566	IC50	6.06	6.06	871.8	1
DLD-1 CHEMBL614285	IC50	6.03	6.03	944.0	1
K562 CHEMBL385	IC50	6.0	6.0	1000.0	1
MDA-MB-468 CHEMBL614335	IC50	5.94	5.72	1140.0	3
MIA PaCa-2 CHEMBL614725	IC50	5.92	5.92	1200.0	1
Signal transducer and activator of transcription 3 CHEMBL4026	IC50	5.92	5.74	1209.0	3
BXPC-3 CHEMBL614530	IC50	5.89	5.6925	1300.0	4
MCF7 CHEMBL387	EC50	5.83	5.83	1490.0	1
Capan-2 CHEMBL1075417	IC50	5.8	5.8	1586.0	1
MDA-MB-231 CHEMBL400	EC50	5.75	5.75	1800.0	1
Signal transducer and activator of transcription 3 CHEMBL4026	EC50	5.72	5.71	1900.0	2
Unchecked CHEMBL612545	IC50	5.71	5.71	1962.0	1
CT26 CHEMBL613866	IC50	5.6	5.6	2500.0	1
U-251 CHEMBL615022	IC50	5.58	5.58	2600.0	1
MKN-45 CHEMBL614354	IC50	5.4	5.4	3943.0	1
PC-3 CHEMBL390	IC50	5.28	5.28	5250.0	1
HEK293 CHEMBL614818	IC50	4.98	4.98	10400.0	1
Signal transducer and activator of transcription 3 CHEMBL4026	Kd	4.89	4.89	13000.0	1
L02 CHEMBL4296457	IC50	4.73	4.73	18630.0	2
HUVEC CHEMBL613979	IC50	4.38	4.38	41280.0	1

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
DU-145	IC50	=	23.04	nM	7.64	Anticancer activity against human DU145 cells after 72 hrs by XTT assay	18829316
A549	IC50	=	120.0	nM	6.92	Cytotoxicity against human A549 cells assessed as reduction in cell proliferatio...	32044231
A549	IC50	=	120.0	nM	6.92	Antiproliferative activity against human A549 cells assessed as inhibition of ce...	37343498
HT-29	IC50	=	140.0	nM	6.85	Antiproliferative activity against human HT-29 cells assessed as reduction in ce...	32631508
MCF7	IC50	=	240.0	nM	6.62	Cytotoxicity against human MCF7 cells assessed as reduction in cell proliferatio...	32044231
MDA-MB-231	IC50	=	250.0	nM	6.6	Cytotoxicity against human MDA-MB-231 cells assessed as reduction in cell prolif...	32044231
MDA-MB-231	IC50	=	250.0	nM	6.6	Antiproliferative activity against human MDA-MB-231 cells assessed as inhibition...	37343498
HCT-116	IC50	=	300.0	nM	6.52	Antiproliferative activity against human HCT-116 cells assessed as reduction in ...	33445154
MDA-MB-231	IC50	=	340.0	nM	6.47	Cytotoxicity against human MDA-MB-231 cells assessed as growth inhibition after ...	28558333
Aldehyde dehydrogenase 1A1	IC50	=	425.32	nM	6.37	Inhibition of ALDH1A1 in human drug-tolerant MDA-MB-231/lapatinib cells assessed...	34435487
AGS	IC50	=	437.0	nM	6.36	Antiproliferative activity against human AGS cells assessed as reduction in cell...	36103247
HaCaT	IC50	=	500.0	nM	6.3	Antihyperproliferative activity against human HaCaT cells after 48 hrs by phase ...	22845014
HaCaT	IC50	=	500.0	nM	6.3	Antiproliferative activity against human HaCaT cells	10479319
MCF-10A	IC50	=	540.0	nM	6.27	Cytotoxicity against human MCF10A cells assessed as reduction in cell viability ...	32631508
HCT-116	IC50	=	620.32	nM	6.21	Antiproliferative activity against human HCT-116 cells assessed as inhibition of...	38704936
MCF7	IC50	=	630.0	nM	6.2	Antiproliferative activity against human MCF7 cells assessed as reduction in cel...	32631508
HepG2	IC50	=	660.0	nM	6.18	Cytotoxicity against human HepG2 cells assessed as growth inhibition after 72 hr...	28558333
HCT-15	IC50	=	660.3	nM	6.18	Antiproliferative activity against human HCT-15 cells harboring STAT3 over activ...	38704936
MDA-MB-231	IC50	=	700.0	nM	6.16	Antiproliferative activity against human MDA-MB-231 cells overexpressing STAT3 a...	32603980
A549	IC50	=	740.0	nM	6.13	Cytotoxicity against human A549 cells assessed as growth inhibition after 72 hrs...	28558333

Literature References

PubMed	DOI	Target Context	# Activities
30003778	10.1021/acs.jnatprod.8b00247	MDA-MB-231	27
32809827	10.1021/acs.jmedchem.0c01016	Unchecked	9
29604543	10.1016/j.ejmech.2018.03.054	HepG2	7
33100009	10.1021/acs.jmedchem.0c01271	ADMET	6
36282975	10.1021/acs.jmedchem.2c01554	ADMET	6
32631508	10.1016/j.bmcl.2020.127286	A549	6
32044231	10.1016/j.bmc.2020.115347	Signal transducer and activator of transcription 3	6
-	10.1007/s00044-012-0284-7	Mus musculus	5
36282975	10.1021/acs.jmedchem.2c01554	Signal transducer and activator of transcription 3	5
32044231	10.1016/j.bmc.2020.115347	Unchecked	5
2558164	10.1021/np50065a012	Unchecked	5
22845014	10.1021/jm3009597	HaCaT	5
33506674	10.1021/acs.jmedchem.0c01897	BXPC-3	4
33506674	10.1021/acs.jmedchem.0c01897	Protein cereblon/STAT3	4
33506674	10.1021/acs.jmedchem.0c01897	Signal transducer and activator of transcription 3	4
2558164	10.1021/np50065a012	Raji	4
30003778	10.1021/acs.jnatprod.8b00247	Signal transducer and activator of transcription 3	4
33100009	10.1021/acs.jmedchem.0c01271	Unchecked	4
10785421	10.1021/np990528l	NON-PROTEIN TARGET	4
36103247	10.1021/acs.jmedchem.2c00413	Signal transducer and activator of transcription 3	3

Data from ChEMBL 36 via Core Engine