Compound Detail

CHEMBL2172467

NAPHTHOMYCIN A

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C/C1=C/C=C\C=C\[C@H](C)[C@@H](O)CC(=O)/C(C)=C/C[C@H](O)/C=C/[C@H](C)[C@H](O)[C@@H](C)/C=C(\C)C(=O)c2c(O)c(C)cc3c2C(=O)C(Cl)=C(NC1=O)C3=O

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL2172467
Name	NAPHTHOMYCIN A
Phase	Preclinical
Structure Type	MOL
InChI Key	AXEGRHYJHHPVDH-UMKVKWLOSA-N

Targets

Activities

Assay Types

PK Parameters

Publications

Known Names

720.3

MW (Da)

5.69

ALogP

HBA

HBD

178.3

PSA (Å²)

0.21

QED

Ro5 Violations

Rot. Bonds

Natural Product First in Class Prodrug

IC50 11 meas. best 6.36

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
Indoleamine 2,3-dioxygenase 1 CHEMBL4685	IC50	6.36	6.36	440.0	1
HL-60 CHEMBL383	IC50	5.68	5.135	2100.0	2
SW480 CHEMBL612544	IC50	5.12	5.025	7600.0	2
MCF7 CHEMBL387	IC50	4.93	4.93	11670.0	1
A549 CHEMBL392	IC50	4.8	4.8	15910.0	1
SMMC-7721 CHEMBL613831	IC50	4.78	4.78	16620.0	1
U2OS CHEMBL615023	IC50	4.69	4.69	20500.0	1
HeLa CHEMBL399	IC50	4.52	4.52	30200.0	1
MDA-MB-231 CHEMBL400	IC50	4.46	4.46	34600.0	1

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
Indoleamine 2,3-dioxygenase 1	IC50	=	440.0	nM	6.36	Inhibition of ascorbic acid/methylene blue activated recombinant human IDO expre...	28406643
HL-60	IC50	=	2100.0	nM	5.68	Antiproliferative activity against human HL60 cells after 48 hrs by EZ-Cytox cel...	28406643
SW480	IC50	=	7600.0	nM	5.12	Antiproliferative activity against human SW480 cells after 48 hrs by MTT assay	28406643
SW480	IC50	=	11660.0	nM	4.93	Growth inhibition of human SW480 cells by MTT assay	22742732
MCF7	IC50	=	11670.0	nM	4.93	Growth inhibition of human MCF7 cells by MTT assay	22742732
A549	IC50	=	15910.0	nM	4.8	Growth inhibition of human A549 cells by MTT assay	22742732
SMMC-7721	IC50	=	16620.0	nM	4.78	Growth inhibition of human SMMC7721 cells by MTT assay	22742732
U2OS	IC50	=	20500.0	nM	4.69	Antiproliferative activity against human U2OS cells after 48 hrs by MTT assay	28406643
HL-60	IC50	=	25610.0	nM	4.59	Growth inhibition of human HL60 cells by MTT assay	22742732
HeLa	IC50	=	30200.0	nM	4.52	Antiproliferative activity against human HeLa cells after 48 hrs by MTT assay	28406643
MDA-MB-231	IC50	=	34600.0	nM	4.46	Antiproliferative activity against human MDA-MB-231 cells after 48 hrs by MTT as...	28406643

PubMed	DOI	Target Context	# Activities
22742732	10.1021/np300109s	Molecular identity unknown	2
22742732	10.1021/np300109s	SW480	1
22742732	10.1021/np300109s	MCF7	1
22742732	10.1021/np300109s	A549	1
22742732	10.1021/np300109s	SMMC-7721	1
22742732	10.1021/np300109s	HL-60	1
22742732	10.1021/np300109s	Pyricularia oryzae	1
22742732	10.1021/np300109s	Fusarium oxysporum	1
22742732	10.1021/np300109s	Fusarium verticillioides	1
28406643	10.1021/acs.jnatprod.6b01059	MDA-MB-231	1
28406643	10.1021/acs.jnatprod.6b01059	Indoleamine 2,3-dioxygenase 1	1
28406643	10.1021/acs.jnatprod.6b01059	HeLa	1
28406643	10.1021/acs.jnatprod.6b01059	SW480	1
28406643	10.1021/acs.jnatprod.6b01059	HL-60	1
28406643	10.1021/acs.jnatprod.6b01059	U2OS	1

Data from ChEMBL 36 via Core Engine