General Information of Metabolite (ID: MT044)
  Meta Name
K3
  Unify Name
Menadione
  Synonym    Click to Show/Hide the Detailed Synonyms of This Metabolite
2-Methyl-1,4-naphthalenedione;2-Methyl-1,4-naphthochinon;2-Methyl-1,4-naphthoquinone;Vitamin K3;Kappaxin;2-Methyl-1,4-naftochinon;2-Methyl-1,4-naphthalendione;2-Methyl-1,4-naphthodione;2-Methylnaphthoquinone;3-Methyl-1,4-naphthoquinone;Aquakay;Aquinone;Hemodal;Juva-K;K-Thrombyl;K-Vitan;Kaergona;Kanone;Kappaxan;Karcon;Kareon;Kativ-g;Kayklot;Kaykot;Kaynone;Kayquinone;Kipca;Kipca-oil soluble;Klottone;Koaxin;Kolklot;Menadion;Menaphthene;Menaphthon;Menaphthone;Menaphtone;Menaquinone;Menaquinone O;Mitenon;Mitenone;MNQ;Panosine;Prokayvit;Synkay;Thyloquinone;Vitamin K0;Vitamin K2;Vitamin K3: 1,4-dihydro-1,4-dioxo-2-methylnaphthaleneL;Bisulfite, menadione;Vicasol;Bisulfite, menadione sodium;Menadione sodium bisulfite;Vikasol;Vitamin K 3;Menadione sodium bisulfite, trihydrate;Vitamin K3 sodium bisulfite;Menadione bisulfite;Sodium bisulfite, menadione
  Molecule Type
Vitamins
  Formula
C11H8O2
  Inchi Key
MJVAVZPDRWSRRC-UHFFFAOYSA-N
  Description    Click to Show/Hide the Detailed Description of This Metabolite
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. -- Pubchem; 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. -- Wikipedia .
  External Links   HMDB ID   HMDB0001892
  KEGG ID   C05377
  Metlin ID   3910

The epigenetic modification information of this metabolite
Modification Type Molecule EM Info Cell/Tissue Type Modified sites Condition REF
Histone Arylation H3 EM Info MCF-7 cells Cys110 Breast cancer [1], [2]
Histone Arylation H3 EM Info SKBr3 cells Cys110 Breast cancer [1], [2]
Histone Arylation H3 EM Info T47D cells Cys110 Breast cancer [1], [2]
Histone Deacetylation HDAC6 EM Info HuH-7 cells . Liver cancer [3], [4]

The microbes that produce this metabolite
      Bifidobacterium
         Detailed Information MIC Info click to show the detail information of this Microbiota [3], [4]
         Description
Bifidobacteria is a genus of gram-positive, nonmotile, often branched anaerobic bacteria. They are ubiquitous inhabitants of the gastrointestinal tract, vagina and mouth of mammals, including humans.
      Lactobacillus salivarius
         Detailed Information MIC Info click to show the detail information of this Microbiota [5], [2]
         Description
Lactobacillus salivarius is a facultative anaerobic, gram-positive bacteria. It is commonly isolated from human, porcine, and avian gastrointestinal tracts. It has proved to be an effective probiotic with at least temporary influence on gut microbiota.

References
1 Vitamin K3 (menadione)-induced oncosis associated with keratin 8 phosphorylation and histone H3 arylation. Mol Pharmacol. 2005 Sep;68(3):606-15. doi: 10.1124/mol.105.013474. Epub 2005 Jun 6.
2 Effect of pH and dilution rate on specific production rate of extra cellular metabolites by Lactobacillus salivarius UCO_979C in continuous culture Appl Microbiol Biotechnol. 2015 Aug;99(15):6417-29. doi: 10.1007/s00253-015-6526-0. Epub 2015 Mar 25.
3 Gut Microbiota as Important Mediator Between Diet and DNA Methylation and Histone Modifications in the Host. Nutrients. 2020 Feb 25;12(3):597. doi: 10.3390/nu12030597.
4 Arachidonic and oleic acid exert distinct effects on the DNA methylome. Epigenetics. 2016 May 3;11(5):321-34. doi: 10.1080/15592294.2016.1161873. Epub 2016 Apr 18.
5 Vitamin K(3) chloro derivative (VKT-2) inhibits HDAC6, activates autophagy and apoptosis, and inhibits aggresome formation in hepatocellular carcinoma cells. Biochem Pharmacol. 2020 Oct;180:114176. doi: 10.1016/j.bcp.2020.114176. Epub 2020 Jul 25.

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