Structure via PubChem · Public domain (PubChem)
menadione
Sign in to saveAlso known as 2-methyl-1,4-dihydronaphthalene-1,4-dione, MNQ, Vitamin K0, 2-methyl-1,4-Naphthalenedione, 2-methyl-1,4-naphthochinon, 2-methyl-1,4-naphthoquinone, vitamin K3, 3-methyl-1,4-naphthoquinone
Menadione is a natural organic compound with the formula C6H4(CO)2C2H(CH3). It is an analog of 1,4-naphthoquinone with a methyl group in the 2-position. It is sometimes called vitamin K3. Use is allowed as a nutritional supplement in animal feed because of its vitamin K activity.
Key facts
- Drug.Verifiedfields
- changed
- Drug.Watchedfields
- changed
- Drug.verifiedrevid
- 411385075
- Drug.image
- Menadione.svg
- Drug.width
- 140
- Drug.alt
- Skeletal formula
- Drug.image_class
- skin-invert-image
- Drug.image2
- Menadione-from-xtal-3D-bs-17.png
- Drug.image_class2
- bg-transparent
- Drug.width2
- 170
- Drug.alt2
- Ball-and-stick model
- Drug.IUPAC_name
- 2-Methylnaphthalene-1,4-dione (preferred)
- Drug.synonyms
- Menaphthone; Vitamin K3; β-Methyl-1,4-naphthoquinone; 2-Methyl-1,4-naphthodione; 2-Methyl-1,4-naphthoquinone
- Drug.ATC_prefix
- B02
- Drug.ATC_suffix
- BA02
- Drug.CAS_number
- 58-27-5
- Drug.PubChem
- 4055
- Drug.DrugBank
- DB00170
via Wikipedia infobox
Chemical data
- Formula
- C11H8O2
- Molecular weight
- 172.18 g/mol
- IUPAC name
- 2-methylnaphthalene-1,4-dione
- SMILES
- CC1=CC(=O)C2=CC=CC=C2C1=O
- InChIKey
- MJVAVZPDRWSRRC-UHFFFAOYSA-N
- XLogP
- 2.2
- Polar surface area
- 34.1 Ų
- H-bond donors
- 0
- H-bond acceptors
- 2
- Formal charge
- 0
via PubChem
Research
3,944 papers- Menadione.Profiles of drug substances, excipients, and related methodology · 2013
- CDC25B Inhibition by Menadione: A Potential New Therapeutical Approach.Anti-cancer agents in medicinal chemistry · 2022
- Menadione Potentiates Auranofin-Induced Glioblastoma Cell Death.International journal of molecular sciences · 2022
- Menadione-induced endothelial inflammation detected by Raman spectroscopy.Biochimica et biophysica acta. Molecular cell research · 2021
- Nitroreductase Increases Menadione-Mediated Oxidative Stress in Aspergillus nidulans.Applied and environmental microbiology · 2021
via PubMed
~4 min read
Encyclopedic overview
10 sectionsContents
- Biochemistry
- Terminology
- Derivatives
- Uses
- Animal feed
- Human use
- Toxicology
- See also
- References
- External links
Menadione is a natural organic compound with the formula C6H4(CO)2C2H(CH3). It is an analog of 1,4-naphthoquinone with a methyl group in the 2-position. It is sometimes called vitamin K3. Use is allowed as a nutritional supplement in animal feed because of its vitamin K activity.
== Biochemistry == Menadione is converted to vitamin K2 (specifically, MK-4) by the prenyltransferase action of vertebrate protein UBIAD1. This reaction requires the hydroquinone (reduced) form of K3, menadiol, produced by NQO1.
Excerpted from Wikipedia’s “menadione” article, available under the CC BY-SA 4.0 licence.