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Human Metabolome Database Version 3.5

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Showing metabocard for Menadione (HMDB01892)

Record Information
Version 3.5
Creation Date 2006-03-08 05:54:47 -0700
Update Date 2013-02-08 17:10:57 -0700
HMDB ID HMDB01892
Secondary Accession Numbers None
Metabolite Identification
Common Name Menadione
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. -- 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.
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. 2-Methyl-1,4-naftochinon
  2. 2-Methyl-1,4-naphthalendione
  3. 2-Methyl-1,4-naphthalenedione
  4. 2-Methyl-1,4-naphthochinon
  5. 2-Methyl-1,4-naphthodione
  6. 2-Methyl-1,4-naphthoquinone
  7. 2-Methylnaphthoquinone
  8. 3-Methyl-1,4-naphthoquinone
  9. Aquakay
  10. Aquinone
  11. Hemodal
  12. Juva-K
  13. K-Thrombyl
  14. K-Vitan
  15. Kaergona
  16. Kanone
  17. Kappaxan
  18. Kappaxin
  19. Karcon
  20. Kareon
  21. Kativ-G
  22. Kayklot
  23. Kaykot
  24. Kaynone
  25. Kayquinone
  26. Kipca
  27. Kipca-Oil Soluble
  28. Klottone
  29. Koaxin
  30. Kolklot
  31. Menadion
  32. Menadione
  33. Menaphthene
  34. Menaphthon
  35. Menaphthone
  36. Menaphtone
  37. Menaquinone
  38. Menaquinone O
  39. Mitenon
  40. Mitenone
  41. MNQ
  42. Panosine
  43. Prokayvit
  44. Synkay
  45. Thyloquinone
  46. Vitamin K0
  47. Vitamin K2
  48. Vitamin K3
  49. Vitamin K3: 1,4-Dihydro-1,4-dioxo-2-methylnaphthalene
Chemical Formula C11H8O2
Average Molecular Weight 172.18
Monoisotopic Molecular Weight 172.0524295
IUPAC Name 2-methyl-1,4-dihydronaphthalene-1,4-dione
Traditional IUPAC 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
Kingdom Organic Compounds
Super Class Aromatic Homomonocyclic Compounds
Class Acenes
Sub Class Naphthalenes
Other Descriptors
  • Aromatic Homomonocyclic Compounds
  • Aromatic Homopolycyclic Compounds
  • Fat-soluble vitamins(KEGG)
  • Vitamin K(KEGG)
  • a vitamin K(Cyc)
  • naphthoquinone(ChEBI)
Substituents
  • Benzoquinone
  • Ketone
Direct Parent Naphthoquinones
Ontology
Status Detected and Quantified
Origin
  • Endogenous
Biofunction
  • Enzyme cofactor
Application Not Available
Cellular locations Not Available
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 2.20 HANSCH,C ET AL. (1995)
Predicted Properties
Property Value Source
Water Solubility 0.5 g/L ALOGPS
LogP 1.91 ALOGPS
LogP 1.89 ChemAxon
LogS -2.53 ALOGPS
pKa (strongest acidic) 12.94 ChemAxon
pKa (strongest basic) -7.2 ChemAxon
Hydrogen Acceptor Count 2 ChemAxon
Hydrogen Donor Count 0 ChemAxon
Polar Surface Area 34.14 A2 ChemAxon
Rotatable Bond Count 0 ChemAxon
Refractivity 50.54 ChemAxon
Polarizability 17.64 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge 0 ChemAxon
Spectra
1H NMR Spectrum
MS/MS Spectrum Quattro_QQQ 10
MS/MS Spectrum Quattro_QQQ 25
MS/MS Spectrum Quattro_QQQ 40
MS/MS Spectrum EI-B (HITACHI M-80)
MS/MS Spectrum GC-MS
MS/MS Spectrum GC-MS
MS/MS Spectrum GC-MS
[1H,13C] 2D NMR Spectrum
Biological Properties
Cellular Locations Not Available
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Fibroblasts
  • Neuron
  • Pancreas
  • Placenta
  • Kidney
  • Liver
  • Prostate
  • Platelet
Pathways Not Available
Normal Concentrations
Biofluid Status Value Age Sex Condition Comments
Blood Expected and not Quantified
Not Applicable Not Available Not Available Normal Inferred from detection in urine
Urine Detected and Quantified
Article_icon
0.00108 (0.0003-0.025) umol/mmol creatinine Adult (>18 years old) Both Normal Not Available
Urine Detected and Quantified
Article_icon
0.000411(0.0001-0.0011) umol/mmol creatinine Adult (>18 years old) Both Normal Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID DB00170 Link_out
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID FDB000953
KNApSAcK ID Not Available
Chemspider ID 3915 Link_out
KEGG Compound ID C05377 Link_out
BioCyc ID CPD-3766 Link_out
BiGG ID Not Available
Wikipedia Link Menadione Link_out
NuGOwiki Link HMDB01892 Link_out
Metagene Link HMDB01892 Link_out
METLIN ID 3910 Link_out
PubChem Compound 4055 Link_out
PDB ID VK3 Link_out
ChEBI ID 28869 Link_out
References
Synthesis Reference Minami, Ryohei; Nishizaki, Tadao; Kumagai, Yoshitoshi. Menadione. Jpn. Kokai Tokkyo Koho (1986), 4 pp.
Material Safety Data Sheet (MSDS) Download (PDF)
General References
  1. Robertson DG, Bailey DL, Martin RA: Species differences in response to photohemolytic agents. Photochem Photobiol. 1991 Apr;53(4):455-61. Pubmed: 1857739 Link_out
  2. Chladek J, Martinkova J, Sispera L: An in vitro study on methotrexate hydroxylation in rat and human liver. Physiol Res. 1997;46(5):371-9. Pubmed: 9728483 Link_out
  3. Habu D, Shiomi S, Tamori A, Takeda T, Tanaka T, Kubo S, Nishiguchi S: Role of vitamin K2 in the development of hepatocellular carcinoma in women with viral cirrhosis of the liver. JAMA. 2004 Jul 21;292(3):358-61. Pubmed: 15265851 Link_out
  4. Lasalvia-Prisco E, Cucchi S, Vazquez J, Lasalvia-Galante E, Golomar W, Gordon W: Serum markers variation consistent with autoschizis induced by ascorbic acid-menadione in patients with prostate cancer. Med Oncol. 2003;20(1):45-52. Pubmed: 12665684 Link_out
  5. Harrington DJ, Soper R, Edwards C, Savidge GF, Hodges SJ, Shearer MJ: Determination of the urinary aglycone metabolites of vitamin K by HPLC with redox-mode electrochemical detection. J Lipid Res. 2005 May;46(5):1053-60. Epub 2005 Feb 1. Pubmed: 15722567 Link_out
  6. 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. Pubmed: 16140270 Link_out
  7. Snider BJ, Moss JL, Revilla FJ, Lee CS, Wheeler VC, Macdonald ME, Choi DW: Neocortical neurons cultured from mice with expanded CAG repeats in the huntingtin gene: unaltered vulnerability to excitotoxins and other insults. Neuroscience. 2003;120(3):617-25. Pubmed: 12895502 Link_out
  8. Usui Y, Tanimura H, Nishimura N, Kobayashi N, Okanoue T, Ozawa K: Vitamin K concentrations in the plasma and liver of surgical patients. Am J Clin Nutr. 1990 May;51(5):846-52. Pubmed: 2333843 Link_out
  9. Ono M, Ohta H, Ohhira M, Sekiya C, Namiki M: Measurement of immunoreactive prothrombin, des-gamma-carboxy prothrombin, and vitamin K in human liver tissues: overproduction of immunoreactive prothrombin in hepatocellular carcinoma. Am J Gastroenterol. 1990 Sep;85(9):1149-54. Pubmed: 1697141 Link_out
  10. Suzuki S, Iwata G, Sutor AH: Vitamin K deficiency during the perinatal and infantile period. Semin Thromb Hemost. 2001;27(2):93-8. Pubmed: 11372776 Link_out
  11. Wermuth B, Platts KL, Seidel A, Oesch F: Carbonyl reductase provides the enzymatic basis of quinone detoxication in man. Biochem Pharmacol. 1986 Apr 15;35(8):1277-82. Pubmed: 3083821 Link_out
  12. Price RJ, Mistry H, Wield PT, Renwick AB, Beamand JA, Lake BG: Comparison of the toxicity of allyl alcohol, coumarin and menadione in precision-cut rat, guinea-pig, cynomolgus monkey and human liver slices. Arch Toxicol. 1996;71(1-2):107-11. Pubmed: 9010592 Link_out
  13. Thijssen HH, Drittij-Reijnders MJ: Vitamin K status in human tissues: tissue-specific accumulation of phylloquinone and menaquinone-4. Br J Nutr. 1996 Jan;75(1):121-7. Pubmed: 8785182 Link_out
  14. Iioka H, Moriyama IS, Morimoto K, Akada S, Hisanaga H, Ishihara Y, Ichijo M: Pharmacokinetics of vitamin K in mothers and children in the perinatal period: transplacental transport of vitamin K2 (MK-4). Asia Oceania J Obstet Gynaecol. 1991 Mar;17(1):97-100. Pubmed: 2064595 Link_out
  15. Strunnikova N, Hilmer S, Flippin J, Robinson M, Hoffman E, Csaky KG: Differences in gene expression profiles in dermal fibroblasts from control and patients with age-related macular degeneration elicited by oxidative injury. Free Radic Biol Med. 2005 Sep 15;39(6):781-96. Pubmed: 16109308 Link_out
Enzymes
Name: Dehydrogenase/reductase SDR family member 4
Reactions:
  • R-CHOH-R' + NADP+ = R-CO-R' + NADPH + H+ [RN:R03557]
Gene Name: DHRS4
Uniprot ID: Q9BTZ2 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Aldehyde oxidase
Reactions:
  • an aldehyde + H2O + O2 = a carboxylic acid + H2O2 [RN:R00635]
Gene Name: AOX1
Uniprot ID: Q06278 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Ribosyldihydronicotinamide dehydrogenase [quinone]
Reactions:
  • 1-(beta-D-ribofuranosyl)-1,4-dihydronicotinamide + a quinone = 1-(beta-D-ribofuranosyl)nicotinamide + a hydroquinone [RN:R07361]
Gene Name: NQO2
Uniprot ID: P16083 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Xanthine dehydrogenase/oxidase
Reactions:
  • xanthine + H2O + O2 = urate + H2O2 [RN:R02107]
Gene Name: XDH
Uniprot ID: P47989 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: NADPH--cytochrome P450 reductase
Reactions:
  • NADPH + H+ + n oxidized hemoprotein = NADP+ + n reduced hemoprotein
Gene Name: POR
Uniprot ID: P16435 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Methylenetetrahydrofolate reductase
Reactions:
  • 5-methyltetrahydrofolate + NAD(P)+ = 5,10-methylenetetrahydrofolate + NAD(P)H + H+ [RN:R01224 R07168]
Gene Name: MTHFR
Uniprot ID: P42898 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Activin receptor type-1
Reactions:
  • ATP + [receptor-protein] = ADP + [receptor-protein] phosphate
Gene Name: ACVR1
Uniprot ID: Q04771 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cytochrome P450 2E1
Reactions:
  • --- []
Gene Name: CYP2E1
Uniprot ID: P05181 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cytochrome P450 1A1
Reactions:
  • RH + reduced flavoprotein + O2 = ROH + oxidized flavoprotein + H2O [RN:R04122]
Gene Name: CYP1A1
Uniprot ID: P04798 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cytochrome P450 1A2
Reactions:
  • RH + reduced flavoprotein + O2 = ROH + oxidized flavoprotein + H2O [RN:R04122]
Gene Name: CYP1A2
Uniprot ID: P05177 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cytochrome P450 2A6
Reactions:
  • RH + reduced flavoprotein + O2 = ROH + oxidized flavoprotein + H2O [RN:R04122]
Gene Name: CYP2A6
Uniprot ID: P11509 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: NAD(P)H dehydrogenase [quinone] 1
Reactions:
  • NAD(P)H + H+ + a quinone = NAD(P)+ + a hydroquinone [RN:R07358 R07359]
Gene Name: NQO1
Uniprot ID: P15559 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Vitamin K-dependent gamma-carboxylase
Reactions:
  • peptidyl-4-carboxyglutamate + 2,3-epoxyphylloquinone + H2O = peptidyl-glutamate + CO2 + O2 + phylloquinone
Gene Name: GGCX
Uniprot ID: P38435 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Coagulation factor IX
Reactions:
  • Selective cleavage of Arg!Ile bond in factor X to form factor Xa
Gene Name: F9
Uniprot ID: P00740 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Vitamin K-dependent protein C
Reactions:
  • Degradation of blood coagulation factors Va and VIIIa
Gene Name: PROC
Uniprot ID: P04070 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Vitamin K-dependent protein S
Reactions:
    Gene Name: PROS1
    Uniprot ID: P07225 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: Vitamin K-dependent protein Z
    Reactions:
      Gene Name: PROZ
      Uniprot ID: P22891 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: Osteocalcin
      Reactions:
        Gene Name: BGLAP
        Uniprot ID: P02818 Link_out
        Protein Sequence: FASTA
        Gene Sequence: FASTA
        Name: Coagulation factor X
        Reactions:
        • Selective cleavage of Arg!Thr and then Arg!Ile bonds in prothrombin to form thrombin
        Gene Name: F10
        Uniprot ID: P00742 Link_out
        Protein Sequence: FASTA
        Gene Sequence: FASTA
        Name: Coagulation factor VII
        Reactions:
        • Selective cleavage of Arg!Ile bond in factor X to form factor Xa INHIBITOR Isoflurophate [CPD:C00202]
        Gene Name: F7
        Uniprot ID: P08709 Link_out
        Protein Sequence: FASTA
        Gene Sequence: FASTA
        Name: Vitamin K epoxide reductase complex subunit 1
        Reactions:
        • 2-methyl-3-phytyl-1,4-naphthoquinone + oxidized dithiothreitol = 2,3-epoxy-2,3-dihydro-2-methyl-3-phytyl-1,4-naphthoquinone + 1,4-dithiothreitol [RN:R03511]
        Gene Name: VKORC1
        Uniprot ID: Q9BQB6 Link_out
        Protein Sequence: FASTA
        Gene Sequence: FASTA
        Name: NADPH-dependent diflavin oxidoreductase 1
        Reactions:
          Gene Name: NDOR1
          Uniprot ID: Q9UHB4 Link_out
          Protein Sequence: FASTA
          Gene Sequence: FASTA
          Name: Vitamin K epoxide reductase complex subunit 1-like protein 1
          Reactions:
            Gene Name: VKORC1L1
            Uniprot ID: Q8N0U8 Link_out
            Protein Sequence: FASTA
            Gene Sequence: FASTA