Record Information
Version2.0
Creation Date2012-05-31 14:05:03 -0600
Update Date2015-09-13 12:56:14 -0600
Secondary Accession Numbers
  • ECMDB04102
Identification
Name:Menaquinone
DescriptionMenaquinone 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
Weight:Average: 172.18
Monoisotopic: 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
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).
KingdomOrganic compounds
Super ClassBenzenoids
ClassNaphthalenes
Sub ClassNaphthoquinones
Direct ParentNaphthoquinones
Alternative Parents
Substituents
  • Naphthoquinone
  • Aryl ketone
  • Quinone
  • Ketone
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic homopolycyclic compound
Molecular FrameworkAromatic 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 Solubility0.5 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity50.54 m³·mol⁻¹ChemAxon
Polarizability17.64 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
SMPDB Pathways:
Sulfur metabolismPW000922 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways:
EcoCyc Pathways:Not Available
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0gk9-3900000000-ad6c0e599173ba802f73View in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0ufr-2910000000-bbd6cf78055e623046a6View in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0ufr-2910000000-5db665917b8c152a80b2View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0g4i-6900000000-0c6c7737ff416205089cView in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0gk9-3900000000-ad6c0e599173ba802f73View in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0ufr-2910000000-bbd6cf78055e623046a6View in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0ufr-2910000000-5db665917b8c152a80b2View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-006x-1900000000-3c2bf459bf04eae7701dView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
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
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-00di-1900000000-b489978f8a44b156f0f3View in MoNA
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-00di-1900000000-b489978f8a44b156f0f3View 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
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0900000000-4b93b7dbc3df04aab3c2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05fr-0900000000-8106d06f0716bb26e582View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-056r-9800000000-8d82921b8e80d22359e4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0900000000-3f44d5db68c8c3181750View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-0900000000-3f44d5db68c8c3181750View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-01dl-9400000000-2f2a9aa33ad848811ec2View in MoNA
MSMass Spectrum (Electron Ionization)splash10-0gk9-5900000000-48fb5ac08ce624a689ccView in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
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

Enzymes

General function:
Involved in FMN binding
Specific function:
Catalyzes the 6-electron oxidation of protoporphyrinogen-IX to form protoporphyrin-IX. Does not use oxygen directly. Is coupled to the respiratory chain
Gene Name:
hemG
Uniprot ID:
P0ACB4
Molecular weight:
21226
Reactions
Protoporphyrinogen IX + 3 menaquinone = protoporphyrin IX + 3 menaquinol.
General function:
Involved in dimethyl sulfoxide reductase activity
Specific function:
Terminal reductase during anaerobic growth on various sulfoxide and N-oxide compounds. Allows E.coli to grow anaerobically on Me(2)SO as respiratory oxidant
Gene Name:
dmsA
Uniprot ID:
P18775
Molecular weight:
90398
Reactions
Dimethylsulfide + menaquinone + H(2)O = dimethylsulfoxide + menaquinol.
General function:
Involved in electron carrier activity
Specific function:
Electron transfer subunit of the terminal reductase during anaerobic growth on various sulfoxide and N-oxide compounds
Gene Name:
dmsB
Uniprot ID:
P18776
Molecular weight:
22869
General function:
Involved in anaerobic electron transport chain
Specific function:
Terminal reductase during anaerobic growth on various sulfoxide and N-oxide compounds. DmsC anchors the dmsAB dimer to the membrane and stabilizes it
Gene Name:
dmsC
Uniprot ID:
P18777
Molecular weight:
30826
General function:
Involved in methyltransferase activity
Specific function:
Methyltransferase required for the conversion of dimethylmenaquinone (DMKH2) to menaquinone (MKH2) and the conversion of 2-polyprenyl-6-methoxy-1,4-benzoquinol (DDMQH2) to 2-polyprenyl-3-methyl-6-methoxy-1,4-benzoquinol (DMQH2)
Gene Name:
ubiE
Uniprot ID:
P0A887
Molecular weight:
28073
Reactions
A demethylmenaquinone + S-adenosyl-L-methionine = a menaquinol + S-adenosyl-L-homocysteine.
S-adenosyl-L-methionine + 2-methoxy-6-all-trans-polyprenyl-1,4-benzoquinol = S-adenosyl-L-homocysteine + 6-methoxy-3-methyl-2-all-trans-polyprenyl-1,4-benzoquinol.

Transporters

General function:
respiratory electron transport chain
Specific function:
Not Available
Gene Name:
ydhU
Uniprot ID:
P77409
Molecular weight:
29582
Reactions
=