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Record Information
Version	2.0
Creation Date	2012-08-09 09:25:25 -0600
Update Date	2015-06-03 17:21:46 -0600
Secondary Accession Numbers	ECMDB21550
Identification
Name:	Menadiol
Description	Menadiol 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	MOLSDF3D-SDFPDBSMILESInChI View 3D Structure × Structure for #<Compound:0xa97db460> Close
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.
Kingdom	Organic compounds
Super Class	Benzenoids
Class	Naphthalenes
Sub Class	Naphthols and derivatives
Direct Parent	Naphthols and derivatives
Alternative Parents	Hydroquinones 1-hydroxy-2-unsubstituted benzenoids Organooxygen compounds Hydrocarbon derivatives
Substituents	1-naphthol Hydroquinone 1-hydroxy-2-unsubstituted benzenoid Organic oxygen compound Hydrocarbon derivative Organooxygen compound Aromatic homopolycyclic compound
Molecular Framework	Aromatic homopolycyclic compounds
External Descriptors	naphthalenediols (CHEBI:6746 ) methylnaphthalenes (CHEBI:6746 ) a small molecule (MENADIOL )
Physical Properties
State:	Solid
Charge:	0
Melting point:	169 °C
Experimental Properties:	Property Value Source
Predicted Properties	Property Value Source Water Solubility 0.55 g/L ALOGPS logP 2.22 ALOGPS logP 2.87 ChemAxon logS -2.5 ALOGPS pKa (Strongest Acidic) 9.53 ChemAxon pKa (Strongest Basic) -6 ChemAxon Physiological Charge 0 ChemAxon Hydrogen Acceptor Count 2 ChemAxon Hydrogen Donor Count 2 ChemAxon Polar Surface Area 40.46 Ų ChemAxon Rotatable Bond Count 0 ChemAxon Refractivity 51.51 m³·mol⁻¹ ChemAxon Polarizability 18.51 ų ChemAxon Number of Rings 2 ChemAxon Bioavailability 1 ChemAxon Rule of Five Yes ChemAxon Ghose Filter Yes ChemAxon Veber's Rule Yes ChemAxon MDDR-like Rule Yes ChemAxon
Biological Properties
Cellular Locations:	Cytoplasm
Reactions:
SMPDB Pathways:	Not Available
KEGG Pathways:	Not Available
EcoCyc Pathways:	Not Available
Concentrations
	Not Available
Spectra
Spectra:	Spectrum Type Description Splash Key Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive splash10-00dj-0900000000-5b5f5ac3cd44f748261f View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Positive splash10-004i-0900000000-45fab1adbc3349caf7ec View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Positive splash10-004i-0900000000-78fb25492d61c5751ab1 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Positive splash10-0a6r-3900000000-7a70329d04eab6b3b211 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Negative splash10-00di-0900000000-74ddb6c2474c7681732b View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Negative splash10-00di-0900000000-08a687e6c7b2c405b1a1 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Negative splash10-0ab9-3900000000-454259da17a2f0ae9b95 View in MoNA 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View 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
Links
External Links:	Resource Link CHEBI ID 6746 HMDB ID HMDB0166920 Pubchem Compound ID 10209 Kegg ID C07126 ChemSpider ID 9794 Wikipedia menadiol BioCyc ID Not Available

Enzymes