Record Information
Version 1.0
Update Date 1/22/2018 12:54:54 PM
Metabolite IDPAMDB000610
Identification
Name: Menaquinone
Description:Menaquinone is a naphthoquinone without the isoprenoid side chain and biological activity. 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.
Structure
Thumb
Synonyms:
  • 2-Methyl-1,4-naftochinon
  • 2-Methyl-1,4-naphthalendione
  • 2-Methyl-1,4-naphthalenedione
  • 2-Methyl-1,4-naphthochinon
  • 2-Methyl-1,4-naphthodione
  • 2-Methyl-1,4-naphthoquinone
  • 2-Methylnaphthoquinone
  • 3-Methyl-1,4-naphthoquinone
  • Aquakay
  • Aquinone
  • Hemodal
  • Juva-K
  • K-Thrombyl
  • K-Vitan
  • Kaergona
  • Kanone
  • Kappaxan
  • Kappaxin
  • Karcon
  • Kareon
  • Kativ-G
  • Kayklot
  • Kaykot
  • Kaynone
  • Kayquinone
  • Kipca
  • Kipca-Oil Soluble
  • Klottone
  • Koaxin
  • Kolklot
  • Menadion
  • Menadione
  • Menaphthene
  • Menaphthon
  • Menaphthone
  • Menaphtone
  • Menaquinone
  • Menaquinone O
  • Mitenon
  • Mitenone
  • MK-8
  • MNQ
  • Panosine
  • Prokayvit
  • Synkay
  • Thyloquinone
  • Vitamin K0
  • Vitamin K2
  • Vitamin K3
  • Vitamin K3: 1,4-Dihydro-1,4-dioxo-2-methylnaphthalene
  • Vitamin K2
Chemical Formula: C11H8O2
Average Molecular Weight: 172.18
Monoisotopic Molecular Weight: 172.0524295
InChI Key: MJVAVZPDRWSRRC-UHFFFAOYSA-N
InChI:InChI=1S/C11H8O2/c1-7-6-10(12)8-4-2-3-5-9(8)11(7)13/h2-6H,1H3
CAS number: 58-27-5
IUPAC Name:2-methyl-1,4-dihydronaphthalene-1,4-dione
Traditional IUPAC Name: menadione
SMILES:CC1=CC(=O)C2=CC=CC=C2C1=O
Chemical Taxonomy
Taxonomy DescriptionThis compound belongs to the class of organic compounds known as naphthoquinones. These are compounds containing a naphthohydroquinone moiety, which consists of a benzene ring linearly fused to a bezene-1,4-dione (quinone).
Kingdom Organic compounds
Super ClassBenzenoids
Class Naphthalenes
Sub ClassNaphthoquinones
Direct Parent Naphthoquinones
Alternative Parents
Substituents
  • Naphthoquinone
  • Aryl ketone
  • Quinone
  • Ketone
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aromatic homopolycyclic compound
Molecular Framework Aromatic homopolycyclic compounds
External Descriptors
Physical Properties
State: Solid
Charge:0
Melting point: 107 °C
Experimental Properties:
PropertyValueSource
Water Solubility:4 mg/mL [HMP experimental]; 0.160 mg/mL at 30 oC [YALKOWSKY,SH & DANNENFELSER,RM (1992)]PhysProp
LogP:2.20 [HANSCH,C ET AL. (1995)]PhysProp
Predicted Properties
PropertyValueSource
Water Solubility0.504 mg/mLALOGPS
logP1.91ALOGPS
logP1.89ChemAxon
logS-2.5ALOGPS
pKa (Strongest Acidic)12.94ChemAxon
pKa (Strongest Basic)-7.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area34.14 Å2ChemAxon
Rotatable Bond Count0ChemAxon
Refractivity50.54 m3·mol-1ChemAxon
Polarizability17.64 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Cytoplasm
Reactions:
Pathways:
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MSsplash10-0gk9-3900000000-ad6c0e599173ba802f73View in MoNA
GC-MSGC-MS Spectrum - GC-MSsplash10-0ufr-2910000000-bbd6cf78055e623046a6View in MoNA
GC-MSGC-MS Spectrum - GC-MSsplash10-0ufr-2910000000-5db665917b8c152a80b2View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-074j-1900000000-a62dd17c23ac6e7fa95dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0aor-1900000000-ce35b89eaf766c9398e8View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-004i-9100000000-65a9c21d7aa7be21de3aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80) , Positivesplash10-0g4i-6900000000-0c6c7737ff416205089cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0900000000-ea17be197704c13eba82View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-2900000000-2d0b65ea01fe9dd6b4feView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001i-7900000000-509fb00927321d93a529View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0900000000-252f2831b39763f805b4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-0900000000-cea08e3f258cdd275a55View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00dr-6900000000-b84149529316a1f0987fView in MoNA
MSMass Spectrum (Electron Ionization)splash10-0gk9-5900000000-48fb5ac08ce624a689ccView in MoNA
1D NMR1H NMR SpectrumNot Available
1D NMR1H NMR SpectrumNot Available
1D NMR13C NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
References
References:
  • 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
  • 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
  • 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
  • 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
  • Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
  • Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882
  • 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
  • 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
  • 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
  • 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
  • Robertson DG, Bailey DL, Martin RA: Species differences in response to photohemolytic agents. Photochem Photobiol. 1991 Apr;53(4):455-61. Pubmed: 1857739
  • 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
  • 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
  • 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
  • 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
  • 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
  • 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
  • Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948. Pubmed: 18331064
Synthesis Reference: Minami, Ryohei; Nishizaki, Tadao; Kumagai, Yoshitoshi. Menadione. Jpn. Kokai Tokkyo Koho (1986), 4 pp.
Material Safety Data Sheet (MSDS) Download (PDF)
External Links:
ResourceLink
CHEBI ID28869
HMDB IDHMDB01892
Pubchem Compound ID4055
Kegg IDC00828
ChemSpider ID3915
WikipediaMenadione
BioCyc IDCPD-9728
EcoCyc IDCPD-9728
Ligand ExpoVK3