Bovine Metabolome Database: Showing metabocard for Menadione (BMDB0001892)

Identification Taxonomy Physical properties Pathways Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-09-30 22:48:42 UTC

Update Date

2020-05-11 20:48:51 UTC

BMDB ID

BMDB0001892

Secondary Accession Numbers

BMDB01892

Metabolite Identification

Common Name

Menadione

Description

Menadione, also known as aquinone or vitamin K3, 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). Menadione is an extremely weak basic (essentially neutral) compound (based on its pKa). Menadione exists in all living organisms, ranging from bacteria to humans. Menadione is a potentially toxic compound.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
2-Methyl-1,4-naphthalenedione	ChEBI
2-Methyl-1,4-naphthochinon	ChEBI
2-Methyl-1,4-naphthoquinone	ChEBI
Vitamin K3	ChEBI
Kappaxin	Kegg
2-Methyl-1,4-naftochinon	HMDB
2-Methyl-1,4-naphthalendione	HMDB
2-Methyl-1,4-naphthodione	HMDB
2-Methylnaphthoquinone	HMDB
3-Methyl-1,4-naphthoquinone	HMDB
Aquakay	HMDB
Aquinone	HMDB
Hemodal	HMDB
Juva-K	HMDB
K-Thrombyl	HMDB
K-Vitan	HMDB
Kaergona	HMDB
Kanone	HMDB
Kappaxan	HMDB
Karcon	HMDB
Kareon	HMDB
Kativ-g	HMDB
Kayklot	HMDB
Kaykot	HMDB
Kaynone	HMDB
Kayquinone	HMDB
Kipca	HMDB
Kipca-oil soluble	HMDB
Klottone	HMDB
Koaxin	HMDB
Kolklot	HMDB
Menadion	HMDB
Menaphthene	HMDB
Menaphthon	HMDB
Menaphthone	HMDB
Menaphtone	HMDB
Menaquinone	HMDB
Menaquinone O	HMDB
Mitenon	HMDB
Mitenone	HMDB
MNQ	HMDB
Panosine	HMDB
Prokayvit	HMDB
Synkay	HMDB
Thyloquinone	HMDB
Vitamin K0	HMDB
Vitamin K2	HMDB
Vitamin K3: 1,4-dihydro-1,4-dioxo-2-methylnaphthalene	HMDB
Bisulfite, menadione	HMDB
Vicasol	HMDB
Bisulfite, menadione sodium	HMDB
Menadione sodium bisulfite	HMDB
Vikasol	HMDB
Vitamin K 3	HMDB
Menadione sodium bisulfite, trihydrate	HMDB
Vitamin K3 sodium bisulfite	HMDB
Menadione bisulfite	HMDB
Sodium bisulfite, menadione	HMDB

Chemical Formula

C₁₁H₈O₂

Average Molecular Weight

172.18

Monoisotopic Molecular Weight

172.0524295

IUPAC Name

2-methyl-1,4-dihydronaphthalene-1,4-dione

Traditional 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

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).

Kingdom

Super Class

Class

Sub Class

Direct Parent

Alternative Parents

Substituents

Naphthoquinone
Aryl ketone
Quinone
Ketone
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic compounds

External Descriptors

naphthoquinone (CHEBI:28869 )
vitamin K (C05377 )
Fat-soluble vitamins (C05377 )
a vitamin K (CPD-3766 )

Ontology

Status

Expected but not Quantified

Origin

Endogenous

Biofunction

Not Available

Application

Not Available

Cellular locations

Cytoplasm
Mitochondria

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	2.2	HANSCH,C ET AL. (1995)

Predicted Properties

Property	Value	Source
logP	1.91	ALOGPS
logP	1.89	ChemAxon
logS	-2.5	ALOGPS
pKa (Strongest Acidic)	12.94	ChemAxon
pKa (Strongest Basic)	-7.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	34.14 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	50.54 m³·mol⁻¹	ChemAxon
Polarizability	17.64 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-0gk9-3900000000-ad6c0e599173ba802f73	View in MoNA
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-0ufr-2910000000-bbd6cf78055e623046a6	View in MoNA
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-0ufr-2910000000-5db665917b8c152a80b2	View in MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0g4i-6900000000-0c6c7737ff416205089c	View in MoNA
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-0gk9-3900000000-ad6c0e599173ba802f73	View in MoNA
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-0ufr-2910000000-bbd6cf78055e623046a6	View in MoNA
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-0ufr-2910000000-5db665917b8c152a80b2	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-006x-1900000000-3c2bf459bf04eae7701d	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	View in JSpectraViewer
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-074j-1900000000-a62dd17c23ac6e7fa95d	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-0aor-1900000000-ce35b89eaf766c9398e8	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-004i-9100000000-65a9c21d7aa7be21de3a	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI M-80) , Positive	splash10-0g4i-6900000000-0c6c7737ff416205089c	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-qTof , Positive	splash10-00di-1900000000-b489978f8a44b156f0f3	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - , positive	splash10-00di-1900000000-b489978f8a44b156f0f3	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00di-0900000000-ea17be197704c13eba82	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00di-2900000000-2d0b65ea01fe9dd6b4fe	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-001i-7900000000-509fb00927321d93a529	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00di-0900000000-252f2831b39763f805b4	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00di-0900000000-cea08e3f258cdd275a55	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00dr-6900000000-b84149529316a1f0987f	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00di-0900000000-4b93b7dbc3df04aab3c2	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-05fr-0900000000-8106d06f0716bb26e582	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-056r-9800000000-8d82921b8e80d22359e4	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00di-0900000000-3f44d5db68c8c3181750	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00di-0900000000-3f44d5db68c8c3181750	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-01dl-9400000000-2f2a9aa33ad848811ec2	View in MoNA
MS	Mass Spectrum (Electron Ionization)	splash10-0gk9-5900000000-48fb5ac08ce624a689cc	View in MoNA
1D NMR	¹H NMR Spectrum (1D, 600 MHz, 100%_DMSO, experimental)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 90 MHz, CDCl₃, experimental)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 25.16 MHz, CDCl₃, experimental)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, 100%_DMSO, experimental)	Not Available	View in JSpectraViewer

Biological Properties

Cellular Locations

Cytoplasm
Mitochondria

Biospecimen Locations

Fibroblasts
Kidney
Liver
Neuron
Pancreas
Placenta
Platelet
Prostate Tissue

Pathways

Not Available

Name	SMPDB/Pathwhiz	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Fibroblasts	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Kidney	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Liver	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Neuron	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Pancreas	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Placenta	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Platelet	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Prostate Tissue	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details