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Record Information
Version2.0
Creation Date2012-08-09 09:25:25 -0600
Update Date2015-06-03 17:21:46 -0600
Secondary Accession Numbers
  • ECMDB21550
Identification
Name:Menadiol
DescriptionMenadiol is a naphthoquinone. These are compounds containing a naphthalene moiety, which consists of two fused benzene rings. Menadiol can be converted to menadione. Menadione is reduced by the two-electron reduction pathway to menadiol, the induction of this enzyme is likely to be an adaptive response of E. coli to partially alleviate the toxicity of menadione.
Structure
Thumb
Synonyms:
  • 2-Methyl-1,4-naphthohydroquinone
  • 2-Methyl-1,4-naphthoquinol
  • 2-Methylhydronaphthoquinone
  • 2-Methylnaphthalene-1,4-diol
  • Dihydrovitamin K3
  • Menadiol
  • Menadiol sodium diphosphate
  • Menadiol sodium diphosphate hexahydrate
  • Menadiol sodium diphosphoric acid
  • Menadiol sodium diphosphoric acid hexahydric acid
  • Methylnaphthohydroquinone
  • Reduced menadione
  • Reduced vitamin K3
  • Vitamin K3H2
Chemical Formula:C11H10O2
Weight:Average: 174.1959
Monoisotopic: 174.068079564
InChI Key:ZJTLZYDQJHKRMQ-UHFFFAOYSA-N
InChI:InChI=1S/C11H10O2/c1-7-6-10(12)8-4-2-3-5-9(8)11(7)13/h2-6,12-13H,1H3
CAS number:481-85-6
IUPAC Name:2-methylnaphthalene-1,4-diol
Traditional IUPAC Name:menadiol
SMILES:CC1=C(O)C2=CC=CC=C2C(O)=C1
Chemical Taxonomy
Description belongs to the class of organic compounds known as naphthols and derivatives. These are naphthalene derivatives carrying one or more hydroxyl (-OH) groups at any ring position.
KingdomOrganic compounds
Super ClassBenzenoids
ClassNaphthalenes
Sub ClassNaphthols and derivatives
Direct ParentNaphthols and derivatives
Alternative Parents
Substituents
  • 1-naphthol
  • Hydroquinone
  • 1-hydroxy-2-unsubstituted benzenoid
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic homopolycyclic compound
Molecular FrameworkAromatic homopolycyclic compounds
External Descriptors
Physical Properties
State:Solid
Charge:0
Melting point:169 °C
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility0.55 g/LALOGPS
logP2.22ALOGPS
logP2.87ChemAxon
logS-2.5ALOGPS
pKa (Strongest Acidic)9.53ChemAxon
pKa (Strongest Basic)-6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area40.46 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity51.51 m³·mol⁻¹ChemAxon
Polarizability18.51 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
SMPDB Pathways:Not Available
KEGG Pathways:Not Available
EcoCyc Pathways:Not Available
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00dj-0900000000-5b5f5ac3cd44f748261fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0900000000-45fab1adbc3349caf7ecView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-0900000000-78fb25492d61c5751ab1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a6r-3900000000-7a70329d04eab6b3b211View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0900000000-74ddb6c2474c7681732bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-0900000000-08a687e6c7b2c405b1a1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0ab9-3900000000-454259da17a2f0ae9b95View in MoNA
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
References
References:
  • 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:Not Available
Material Safety Data Sheet (MSDS)Not Available
External Links:
ResourceLink
CHEBI ID6746
HMDB IDHMDB0166920
Pubchem Compound ID10209
Kegg IDC07126
ChemSpider ID9794
Wikipediamenadiol
BioCyc IDNot Available

Enzymes

General function:
Involved in oxidoreductase activity
Specific function:
Can oxidize menadiol to menadione
Gene Name:
ygiN
Uniprot ID:
P0ADU2
Molecular weight:
11532