Bovine Metabolome Database: Showing metabocard for Menadione (BMDB0001892)

Identification Taxonomy Physical properties Pathways Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-09-30 22:48:42 UTC

Update Date

2020-05-11 20:48:51 UTC

BMDB ID

BMDB0001892

Secondary Accession Numbers

BMDB01892

Metabolite Identification

Common Name

Menadione

Description

Menadione, also known as aquinone or vitamin K3, belongs to the class of organic compounds known as naphthoquinones. Naphthoquinones are compounds containing a naphthohydroquinone moiety, which consists of a benzene ring linearly fused to a bezene-1,4-dione (quinone). Menadione is an extremely weak basic (essentially neutral) compound (based on its pKa). Menadione exists in all living organisms, ranging from bacteria to humans. Menadione is a potentially toxic compound.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
2-Methyl-1,4-naphthalenedione	ChEBI
2-Methyl-1,4-naphthochinon	ChEBI
2-Methyl-1,4-naphthoquinone	ChEBI
Vitamin K3	ChEBI
Kappaxin	Kegg
2-Methyl-1,4-naftochinon	HMDB
2-Methyl-1,4-naphthalendione	HMDB
2-Methyl-1,4-naphthodione	HMDB
2-Methylnaphthoquinone	HMDB
3-Methyl-1,4-naphthoquinone	HMDB
Aquakay	HMDB
Aquinone	HMDB
Hemodal	HMDB
Juva-K	HMDB
K-Thrombyl	HMDB
K-Vitan	HMDB
Kaergona	HMDB
Kanone	HMDB
Kappaxan	HMDB
Karcon	HMDB
Kareon	HMDB
Kativ-g	HMDB
Kayklot	HMDB
Kaykot	HMDB
Kaynone	HMDB
Kayquinone	HMDB
Kipca	HMDB
Kipca-oil soluble	HMDB
Klottone	HMDB
Koaxin	HMDB
Kolklot	HMDB
Menadion	HMDB
Menaphthene	HMDB
Menaphthon	HMDB
Menaphthone	HMDB
Menaphtone	HMDB
Menaquinone	HMDB
Menaquinone O	HMDB
Mitenon	HMDB
Mitenone	HMDB
MNQ	HMDB
Panosine	HMDB
Prokayvit	HMDB
Synkay	HMDB
Thyloquinone	HMDB
Vitamin K0	HMDB
Vitamin K2	HMDB
Vitamin K3: 1,4-dihydro-1,4-dioxo-2-methylnaphthalene	HMDB
Bisulfite, menadione	HMDB
Vicasol	HMDB
Bisulfite, menadione sodium	HMDB
Menadione sodium bisulfite	HMDB
Vikasol	HMDB
Vitamin K 3	HMDB
Menadione sodium bisulfite, trihydrate	HMDB
Vitamin K3 sodium bisulfite	HMDB
Menadione bisulfite	HMDB
Sodium bisulfite, menadione	HMDB

Chemical Formula

C₁₁H₈O₂

Average Molecular Weight

172.18

Monoisotopic Molecular Weight

172.0524295

IUPAC Name

2-methyl-1,4-dihydronaphthalene-1,4-dione

Traditional Name

menadione

CAS Registry Number

58-27-5

SMILES

CC1=CC(=O)C2=CC=CC=C2C1=O

InChI Identifier

InChI=1S/C11H8O2/c1-7-6-10(12)8-4-2-3-5-9(8)11(7)13/h2-6H,1H3

InChI Key

MJVAVZPDRWSRRC-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as naphthoquinones. Naphthoquinones are compounds containing a naphthohydroquinone moiety, which consists of a benzene ring linearly fused to a bezene-1,4-dione (quinone).

Kingdom

Super Class

Class

Sub Class

Direct Parent

Alternative Parents

Substituents

Naphthoquinone
Aryl ketone
Quinone
Ketone
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic compounds

External Descriptors

naphthoquinone (CHEBI:28869 )
vitamin K (C05377 )
Fat-soluble vitamins (C05377 )
a vitamin K (CPD-3766 )

Ontology

Status

Expected but not Quantified

Origin

Endogenous

Biofunction

Not Available

Application

Not Available

Cellular locations

Cytoplasm
Mitochondria

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	107 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.160 mg/mL at 30 °C	YALKOWSKY,SH & DANNENFELSER,RM (1992)
LogP	2.2	HANSCH,C ET AL. (1995)

Predicted Properties

Property	Value	Source
logP	1.91	ALOGPS
logP	1.89	ChemAxon
logS	-2.5	ALOGPS
pKa (Strongest Acidic)	12.94	ChemAxon
pKa (Strongest Basic)	-7.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	34.14 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	50.54 m³·mol⁻¹	ChemAxon
Polarizability	17.64 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Biological Properties

Cellular Locations

Cytoplasm
Mitochondria

Biospecimen Locations

Fibroblasts
Kidney
Liver
Neuron
Pancreas
Placenta
Platelet
Prostate Tissue

Pathways

Not Available

Name	SMPDB/Pathwhiz	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Fibroblasts	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Kidney	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Liver	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Neuron	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Pancreas	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Placenta	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Platelet	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Prostate Tissue	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details