Compound Detail

CHEMBL455983

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CCOC(=O)N1CCN(/[N+]([O-])=N/Oc2ccc([N+](=O)[O-])cc2[N+](=O)[O-])CC1

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL455983
Phase	Preclinical
Structure Type	MOL
InChI Key	DNJRNBYZLPKSHV-RGEXLXHISA-N

Targets

Activities

Assay Types

PK Parameters

Publications

Known Names

Molecular Properties

384.3

MW (Da)

1.45

ALogP

HBA

HBD

166.7

PSA (Å²)

0.30

QED

Ro5 Violations

Rot. Bonds

Drug Information

Molecule Type	Small molecule
Availability	Unknown
Chirality	Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula	C13H16N6O8
MW	384.31
Aromatic Rings	1
Heavy Atoms	27
NP-Likeness	-1.10

Activity Summary

IC50 64 meas. best 6.7

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
HL-60 CHEMBL383	IC50	6.7	6.5633	200.0	6
U-937 CHEMBL612794	IC50	6.52	6.52	300.0	2
TK-10 CHEMBL614056	IC50	6.3	6.3	500.0	1
HCT-116 CHEMBL394	IC50	6.3	5.805	500.0	2
NCI-H1703 CHEMBL1075522	IC50	6.24	6.105	570.0	2
HCT-15 CHEMBL612263	IC50	6.22	6.22	600.0	1
A2780 CHEMBL614004	IC50	6.2	6.2	630.0	1
NON-PROTEIN TARGET CHEMBL3879801	IC50	6.16	5.855	700.0	10
A549 CHEMBL392	IC50	6.16	5.73	690.0	6
HT-29 CHEMBL384	IC50	6.1	6.1	800.0	1
OVCAR-3 CHEMBL614213	IC50	6.1	6.1	800.0	1
CCRF-CEM CHEMBL382	IC50	6.05	6.05	890.0	1
Jurkat E6.1 CHEMBL4296446	IC50	6.04	6.04	920.0	1
NCI-H441 CHEMBL1075542	IC50	6.03	6.03	940.0	1
OVCAR-5 CHEMBL614214	IC50	6.0	6.0	1000.0	1
MCF7 CHEMBL387	IC50	6.0	6.0	993.0	1
PC-3 CHEMBL390	IC50	5.96	5.96	1100.0	1
Vero CHEMBL391	IC50	5.94	5.94	1160.0	1
B16 CHEMBL381	IC50	5.87	5.87	1340.0	1
L02 CHEMBL4296457	IC50	5.7	5.7	1990.0	1
A549/TR CHEMBL4483226	IC50	5.7	5.7	1987.0	1
Unchecked CHEMBL612545	IC50	5.7	5.7	1990.0	2
Caco-2 CHEMBL614058	IC50	5.58	5.58	2600.0	1
MDA-MB-231 CHEMBL400	IC50	5.54	5.2933	2900.0	3
NCI-H2122 CHEMBL1075533	IC50	5.5	5.5	3170.0	1
HeLa CHEMBL399	IC50	5.45	5.45	3560.0	1
BT-474 CHEMBL614529	IC50	5.44	5.44	3660.0	1
MCF-10A CHEMBL614321	IC50	5.31	5.31	4910.0	1
HepG2 CHEMBL395	IC50	5.29	5.12	5190.0	4
Bel-7402 CHEMBL614279	IC50	5.29	5.29	5170.0	1
HUVEC CHEMBL613979	IC50	5.27	5.27	5390.0	1
U2OS CHEMBL615023	IC50	5.2	5.2	6270.0	1
SMMC-7721 CHEMBL613831	IC50	5.14	5.14	7310.0	1
ADMET CHEMBL612558	IC50	5.0	4.975	10000.0	2
SK-OV-3 CHEMBL614925	IC50	4.73	4.73	18500.0	1

Pharmacokinetic Data

Parameter	Value	Units	Species
T1/2	0.5	hr	-
T1/2	0.2617	hr	-
T1/2	0.04667	hr	-
T1/2	2.0	hr	Rattus norvegicus
T1/2	0.04667	hr	-
T1/2	0.2617	hr	-

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
HL-60	IC50	=	200.0	nM	6.7	Antileukemic activity in human HL60 cells assessed as nitric oxide release	18178089
HL-60	IC50	=	200.0	nM	6.7	Antiproliferative activity against human HL60 cells assessed as decrease in cell...	28505442
HL-60	IC50	=	200.0	nM	6.7	Antiproliferative activity against human HL60 cells after 24 hrs	19364650
HL-60	IC50	=	200.0	nM	6.7	Antiproliferative activity against human HL-60 cells after 72 hrs by MTT assay	18930407
U-937	IC50	=	300.0	nM	6.52	Antiproliferative activity against human U937 cells after 72 hrs by MTT assay	18930407
U-937	IC50	=	300.0	nM	6.52	Antiproliferative activity against human U937 cells after 24 hrs	19364650
HL-60	IC50	=	500.0	nM	6.3	Antiproliferative activity against human HL60 cell line	16821795
TK-10	IC50	=	500.0	nM	6.3	Antiproliferative activity against human TK-10 cells after 72 hrs by MTT assay	18930407
HCT-116	IC50	=	500.0	nM	6.3	Antiproliferative activity against human HCT116 cells harboring KRAS G13D mutant...	32305784
HL-60	IC50	=	530.0	nM	6.28	Antiproliferative activity against human HL60 cells harboring NRAS K61L mutant a...	32305784
NCI-H1703	IC50	=	570.0	nM	6.24	Antiproliferative activity against human NCI-H1703 cells after 72 hrs by MTT ass...	22003962
HCT-15	IC50	=	600.0	nM	6.22	Antiproliferative activity against human HCT-15 cells after 72 hrs by MTT assay	18930407
A2780	IC50	=	630.0	nM	6.2	Antiproliferative activity against human A2780 cells after 48 hrs by MTT assay	25350923
NON-PROTEIN TARGET	IC50	=	700.0	nM	6.16	Antiproliferative activity against human HCT 116 cells after 72 hrs by MTT assay	18930407
A549	IC50	=	690.0	nM	6.16	Antiproliferative activity against human A549 cells harboring KRAS G12S mutant a...	32305784
NON-PROTEIN TARGET	IC50	=	800.0	nM	6.1	Antiproliferative activity against human 786O cells after 72 hrs by MTT assay	18930407
HT-29	IC50	=	800.0	nM	6.1	Antiproliferative activity against human HT-29 cells after 72 hrs by MTT assay	18930407
OVCAR-3	IC50	=	800.0	nM	6.1	Antiproliferative activity against human OVCAR-3 cells after 72 hrs by MTT assay	18930407
NON-PROTEIN TARGET	IC50	=	800.0	nM	6.1	Antiproliferative activity against human H1395 cells after 72 hrs by MTT assay	18930407
NON-PROTEIN TARGET	IC50	=	860.0	nM	6.07	Antiproliferative activity against human NCI-H1373 cells after 72 hrs by MTT ass...	22003962

Literature References

PubMed	DOI	Target Context	# Activities
29501947	10.1016/j.ejmech.2018.02.062	A549/TR	22
22003962	10.1021/jm2004128	NCI-H1703	12
22003962	10.1021/jm2004128	Molecular identity unknown	11
18930407	10.1016/j.bmc.2008.09.063	NON-PROTEIN TARGET	6
32305784	10.1016/j.ejmech.2020.112271	MDA-MB-231	5
23617697	10.1021/jm400393u	HepG2	5
29220794	10.1016/j.ejmech.2017.11.081	Unchecked	4
16821795	10.1021/jm060022h	Panel NCI-51 (51 carcinoma cell lines)	3
18930407	10.1016/j.bmc.2008.09.063	Glutathione S-transferase Mu 1	3
18930407	10.1016/j.bmc.2008.09.063	Glutathione S-transferase A1	3
18930407	10.1016/j.bmc.2008.09.063	Glutathione S-transferase P	3
25350923	10.1021/jm500613m	A2780	3
29220794	10.1016/j.ejmech.2017.11.081	Glutathione S-transferase P	3
22003962	10.1021/jm2004128	Mus musculus	3
23617697	10.1021/jm400393u	Bel-7402	2
18930407	10.1016/j.bmc.2008.09.063	ADMET	2
23617697	10.1021/jm400393u	SMMC-7721	2
-	10.1039/C5MD00158G	HepG2	2
22480849	10.1016/j.bmc.2012.02.045	No relevant target	2
-	10.1039/C5MD00158G	NON-PROTEIN TARGET	2

Data from ChEMBL 36 via Core Engine