Compound Detail

CHEMBL590

MENADIONE

💊 Approved Drug

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💊 Approved Drug

CC1=CC(=O)c2ccccc2C1=O

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL590
Name	MENADIONE
Phase	Approved
Structure Type	MOL
InChI Key	MJVAVZPDRWSRRC-UHFFFAOYSA-N

Known Names

1,4-naphthalenedione, 2-methyl Kayquinone Menadione NSC-4170 Vitamin k 3 Vitamin k3

Targets

Activities

Assay Types

PK Parameters

Publications

Known Names

Indications

Molecular Properties

172.2

MW (Da)

2.01

ALogP

HBA

HBD

34.1

PSA (Å²)

0.60

QED

Ro5 Violations

Rot. Bonds

Drug Information

Molecule Type	Small molecule
First Approval	1982
Availability	Discontinued
Chirality	Achiral

Routes of Administration

Oral

Flags

Natural Product

Extended Properties

Molecular Formula	C11H8O2
MW	172.18
Aromatic Rings	1
Heavy Atoms	13
NP-Likeness	1.10

Indications

Hemorrhage

ATC Classification

B02BA02

menadione

Level 1: BLOOD AND BLOOD FORMING ORGANS

Level 2: ANTIHEMORRHAGICS

Activity Summary

IC50 72 meas. best 6.96

EC50 7 meas. best 5.52

Ki 6 meas. best 6.4

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
Aldehyde oxidase 1 CHEMBL1641357	IC50	6.96	6.96	110.0	1
Aldehyde oxidase 1 CHEMBL1641354	IC50	6.82	6.82	150.0	1
Aldehyde oxidase 1 CHEMBL1641355	IC50	6.72	6.72	190.0	1
Aldehyde oxidase CHEMBL3257	IC50	6.7	5.35	200.0	2
Indoleamine 2,3-dioxygenase 1 CHEMBL4685	IC50	6.43	6.13	370.0	3
Amine oxidase [flavin-containing] B CHEMBL2039	Ki	6.4	6.4	400.0	1
Aldehyde oxidase CHEMBL3257	Ki	6.33	6.075	470.0	2
Thiosulfate sulfurtransferase CHEMBL4295835	IC50	6.0	6.0	1000.0	1
Unchecked CHEMBL612545	IC50	5.89	5.1867	1290.0	3
Aldehyde oxidase 1 CHEMBL1641356	IC50	5.7	5.7	2000.0	1
M-phase inducer phosphatase 2 CHEMBL4804	IC50	5.66	5.5133	2200.0	3
GroEL/GroES CHEMBL4106139	IC50	5.6	5.325	2500.0	2
A2780 CHEMBL614004	IC50	5.58	5.58	2600.0	1
N2a CHEMBL614062	IC50	5.57	5.57	2688.0	1
Danio rerio CHEMBL613963	EC50	5.52	5.52	3000.0	1
ADMET CHEMBL612558	IC50	5.51	4.9867	3100.0	3
HeLa CHEMBL399	EC50	5.43	5.43	3700.0	1
Replicase polyprotein 1ab CHEMBL4523582	IC50	5.43	5.265	3670.0	2
Jurkat CHEMBL397	IC50	5.3	5.3	5000.0	1
HL-60 CHEMBL383	IC50	5.25	5.185	5600.0	2
MIA PaCa-2 CHEMBL614725	IC50	5.21	5.21	6200.0	1
MONO-MAC-6 CHEMBL2366062	IC50	5.21	5.21	6200.0	1
U-937 CHEMBL612794	IC50	5.2	5.2	6300.0	1
THP-1 CHEMBL614245	IC50	5.2	5.2	6300.0	1
M-phase inducer phosphatase 1 CHEMBL3775	IC50	5.16	5.16	6900.0	1
Perilipin-1/ABHD5 CHEMBL3883313	IC50	5.1	5.1	7895.0	1
MCF7 CHEMBL387	IC50	5.05	5.05	9000.0	1
SW982 CHEMBL2366238	IC50	5.03	5.03	9300.0	1
1-acylglycerol-3-phosphate O-acyltransferase ABHD5/Perilipin-5 CHEMBL3885501	IC50	5.02	5.02	9468.0	1
DU-145 CHEMBL613508	IC50	5.01	4.985	9860.0	2
HGC-27 CHEMBL1075463	IC50	5.01	5.01	9700.0	1
HT-29 CHEMBL384	IC50	5.01	4.94	9690.0	2
MGC-803 CHEMBL3706566	IC50	4.93	4.93	11850.0	1
Glutathione reductase, mitochondrial CHEMBL2755	Ki	4.92	4.855	12100.0	2
HCT-116 CHEMBL394	IC50	4.91	4.91	12370.0	1
Rattus norvegicus CHEMBL376	IC50	4.91	4.91	12240.0	1
MDA-MB-231 CHEMBL400	IC50	4.9	4.9	12680.0	1
DBTRG-05MG CHEMBL614801	IC50	4.89	4.775	13000.0	2
A2058 CHEMBL613503	IC50	4.87	4.87	13400.0	1
SAS CHEMBL1075569	IC50	4.85	4.85	14000.0	1
PBMC CHEMBL613107	IC50	4.84	4.84	14500.0	1
HSP60/HSP10 CHEMBL4106131	IC50	4.82	4.82	15000.0	1
Alpha-synuclein CHEMBL6152	IC50	4.82	4.82	15000.0	1
A549 CHEMBL392	IC50	4.8	4.7	15890.0	2
HaCaT CHEMBL614392	IC50	4.8	4.8	15800.0	4
HeLa CHEMBL399	IC50	4.75	4.68	18000.0	2
NON-PROTEIN TARGET CHEMBL3879801	EC50	4.75	4.4467	17700.0	3
M-phase inducer phosphatase 3 CHEMBL2378	IC50	4.73	4.725	18800.0	2
Dual specificity protein phosphatase 6 CHEMBL5511	IC50	4.69	4.69	20500.0	1
Dual specificity protein phosphatase 1 CHEMBL5623	IC50	4.62	4.62	24000.0	1

Pharmacokinetic Data

Parameter	Value	Units	Species
T1/2	0.45	hr	Mus musculus

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
Aldehyde oxidase 1	IC50	=	110.0	nM	6.96	Inhibition of monkey aldehyde oxidase	20853847
Aldehyde oxidase 1	IC50	=	150.0	nM	6.82	Inhibition of mouse aldehyde oxidase	20853847
Aldehyde oxidase 1	IC50	=	190.0	nM	6.72	Inhibition of rat aldehyde oxidase	20853847
Aldehyde oxidase	IC50	=	200.0	nM	6.7	Inhibition of human aldehyde oxidase	20853847
Indoleamine 2,3-dioxygenase 1	IC50	=	370.0	nM	6.43	Inhibition of ascorbic acid/methylene blue activated recombinant human IDO expre...	28406643
Amine oxidase [flavin-containing] B	Ki	=	400.0	nM	6.4	Competitive inhibition of human recombinant MAO-B expressed in baculovirus infec...	22071524
Aldehyde oxidase	Ki	=	470.0	nM	6.33	Competitive inhibition of human liver cytosolic aldehyde oxidase using DACA as s...	22996261
Indoleamine 2,3-dioxygenase 1	IC50	=	1000.0	nM	6.0	Inhibition of purified human recombinant IDO	18318466
Thiosulfate sulfurtransferase	IC50	=	1000.0	nM	6.0	Inhibition of native rhodanese (unknown origin) assessed as reduction in rhodane...	30852084
Indoleamine 2,3-dioxygenase 1	IC50	=	1100.0	nM	5.96	Inhibition of 2,3 dioxygenase	20580138
Unchecked	IC50	=	1290.0	nM	5.89	Inhibition of aldehyde oxidase in Sprague-Dawley rat liver cytosolic fraction us...	-
Aldehyde oxidase	Ki	=	1500.0	nM	5.82	Uncompetitive inhibition of human liver cytosolic aldehyde oxidase using DACA as...	22996261
Aldehyde oxidase 1	IC50	=	2000.0	nM	5.7	Inhibition of rabbit aldehyde oxidase	20853847
M-phase inducer phosphatase 2	IC50	=	2200.0	nM	5.66	Inhibition of MBP-fused recombinant wild type CDC25B3 using fluorescein 3,6 diph...	23141909
GroEL/GroES	IC50	=	2500.0	nM	5.6	Inhibition of Escherichia coli GroEL expressed in Escherichia coli DH5alpha/Esch...	30852084
A2780	IC50	=	2600.0	nM	5.58	Antiproliferative activity against human A2780 cells after 2 days by alamar-blue...	19028102
N2a	IC50	=	2688.0	nM	5.57	Inhibition of reactive oxygen species production in mouse Neuro2a cells assessed...	28152427
Danio rerio	EC50	=	3000.0	nM	5.52	Anti-seizure activity in Zebrafish	32390424
ADMET	IC50	=	3100.0	nM	5.51	Inhibition of guinea pig aldehyde oxidase	20853847
Unchecked	IC50	=	3400.0	nM	5.47	In vitro antimalarial activity against human malaria parasite, P falciparum (Vie...	2033589

Literature References

PubMed	DOI	Target Context	# Activities
-	10.1007/s00044-007-9018-7	Rattus norvegicus	13
19093848	10.1021/np800572r	Mycobacterium tuberculosis	12
35085721	10.1016/j.bmcl.2022.128586	MGC-803	7
24964246	10.1021/jm500754d	HaCaT	7
28410493	10.1016/j.ejmech.2017.03.084	HaCaT	6
7097727	10.1021/jm00348a023	Mus musculus	6
11170645	10.1021/jm001079l	Dihydrolipoyl dehydrogenase, mitochondrial	6
15537352	10.1021/jm0497545	Glutathione reductase, mitochondrial	5
30852084	10.1016/j.bmcl.2019.02.028	Unchecked	5
19564371	10.1128/aac.00550-09	Mycobacterium tuberculosis	5
27783973	10.1016/j.ejmech.2016.10.034	Staphylococcus aureus	5
11170645	10.1021/jm001079l	Trypanothione reductase	5
22845014	10.1021/jm3009597	HaCaT	5
10956224	10.1021/jm000179o	NAD(P)H dehydrogenase [quinone] 1	5
31525930	10.1021/acs.jmedchem.9b00942	Indoleamine 2,3-dioxygenase 1	5
2558164	10.1021/np50065a012	Raji	4
11170645	10.1021/jm001079l	ADMET	4
19564371	10.1128/aac.00550-09	Mycobacterium tuberculosis variant bovis BCG	4
-	10.1039/C3MD00149K	NON-PROTEIN TARGET	4
2558164	10.1021/np50065a012	Unchecked	4

Data from ChEMBL 36 via Core Engine