SynCED: Menadione

Record Information

Version

1.0

Creation Date

2009-07-21 20:26:13 UTC

Update Date

2026-05-14 16:24:26 UTC

Accession Number

CHEM002136

Identification

Common Name

Menadione

Class

Small Molecule

Description

Menadione is a synthetic naphthoquinone without the isoprenoid side chain and biological activity, but can be converted to active vitamin K2, menaquinone, after alkylation in vivo. Despite the fact that it can serve as a precursor to various types of vitamin K, menadione is generally not used as a nutritional supplement. Large doses of menadione have been reported to cause adverse outcomes including hemolytic anemia due to G6PD deficiency, neonatal brain or liver damage, or neonatal death in some cases. Moreover, menadione supplements have been banned by the FDA because of their high toxicity. It is sometimes called vitamin K3, although derivatives of naphthoquinone without the sidechain in the 3-position cannot exert all the functions of the K vitamins. Menadione is a vitamin precursor of K2 which utilizes alkylation in the liver to yield menaquinones (MK-n, n=1-13; K2 vitamers), and hence, is better classified as a provitamin.

Contaminant Sources

FooDB Chemicals
HMDB Contaminants - Urine
IARC Carcinogens Group 3
STOFF IDENT Compounds
T3DB toxins
ToxCast & Tox21 Chemicals

Contaminant Type

Antifibrinolytic Agent
Dietary Supplement
Drug
Ester
Food Toxin
Metabolite
Micronutrient
Nutraceutical
Organic Compound
Supplement
Synthetic Compound
Vitamin

Chemical 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 Mass

172.180 g/mol

Monoisotopic Mass

172.052 g/mol

CAS Registry Number

58-27-5

IUPAC Name

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

Traditional Name

menadione

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 )

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Cytoplasm
Extracellular

Biofluid Locations

Not Available

Tissue Locations

Fibroblasts
Kidney
Liver
Neuron
Pancreas
Placenta
Platelet
Prostate

Pathways

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Solid

Appearance

White powder.

Experimental Properties

Property	Value
Melting Point	107°C
Boiling Point	Not Available
Solubility	160 mg/L (at 30°C)

Predicted Properties

Property	Value	Source
Water Solubility	0.5 g/L	ALOGPS
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	No	ChemAxon

Spectra

Toxicity Profile

Route of Exposure

Variable and ranges from 10% to 80%

Mechanism of Toxicity

Menadione (vitamin K3) is involved as a cofactor in the posttranslational gamma-carboxylation of glutamic acid residues of certain proteins in the body. These proteins include the vitamin K-dependent coagulation factors II (prothrombin), VII (proconvertin), IX (Christmas factor), X (Stuart factor), protein C, protein S, protein Zv and a growth-arrest-specific factor (Gas6). In contrast to the other vitamin K-dependent proteins in the blood coagulation cascade, protein C and protein S serve anticoagulant roles. The two vitamin K-dependent proteins found in bone are osteocalcin, also known as bone G1a (gamma-carboxyglutamate) protein or BGP, and the matrix G1a protein or MGP. Gamma-carboxylation is catalyzed by the vitamin K-dependent gamma-carboxylases. The reduced form of vitamin K, vitamin K hydroquinone, is the actual cofactor for the gamma-carboxylases. Proteins containing gamma-carboxyglutamate are called G1a proteins.

Metabolism

Hepatic

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

3, not classifiable as to its carcinogenicity to humans. (16)

Uses/Sources

The primary known function of vitamin K is to assist in the normal clotting of blood, but it may also play a role in normal bone calcification.

Minimum Risk Level

Not Available

Health Effects

Not Available

Symptoms

Menadione (vitamin K3), which is not used as a nutritional supplemental form of vitamin K for humans, has been reported to cause adverse reactions, including hemolytic anemia. Large doses have also been reported to cause brain damage.

Treatment

Not Available

Concentrations

Not Available

External Links

DrugBank ID

DB00170

HMDB ID

HMDB0001892

FooDB ID

FDB000953

Phenol Explorer ID

Not Available

KNApSAcK ID

Not Available

BiGG ID

Not Available

BioCyc ID

Not Available

METLIN ID

3910

PDB ID

Not Available

Wikipedia Link

Chemspider ID

ChEBI ID

PubChem Compound ID

Kegg Compound ID

YMDB ID

Not Available

ECMDB ID

ECMDB04102

References

Synthesis Reference

Joachim U. Schneider, Hans Kiefer, “Menadione choline bisulfite adduct, its preparation and antihemorrhagic compositions.” U.S. Patent US4735969, issued January, 1980.

MSDS

Link

General References

1. https://www.ncbi.nlm.nih.gov/pubmed/?term=13779073

2. https://www.ncbi.nlm.nih.gov/pubmed/?term=15052609

3. https://www.ncbi.nlm.nih.gov/pubmed/?term=16469140

4. https://www.ncbi.nlm.nih.gov/pubmed/?term=1650428

5. https://www.ncbi.nlm.nih.gov/pubmed/?term=28166217

6. https://www.ncbi.nlm.nih.gov/pubmed/?term=9380028

7. Minami, Ryohei; Nishizaki, Tadao; Kumagai, Yoshitoshi. Menadione. Jpn. Kokai Tokkyo Koho (1986), 4 pp.

8. Minami, Ryohei; Nishizaki, Tadao; Kumagai, Yoshitoshi. Menadione. Jpn. Kokai Tokkyo Koho (1986), 4 pp.

9. Kwasnicka-Crawford DA, Vincent SR: Role of a novel dual flavin reductase (NR1) and an associated histidine triad protein (DCS-1) in menadione-induced cytotoxicity. Biochem Biophys Res Commun. 2005 Oct 21;336(2):565-71.