MiMeDB: Showing metabocard for Menaquinone (MMDBc0029791)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-17 23:41:48 UTC

Update Date

2024-10-09 20:09:38 UTC

Metabolite ID

MMDBc0029791

Metabolite Identification

Common 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

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 170                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1  O   UNK     0       5.747  -3.080   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0       5.747   3.080   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       7.080  -0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.080   0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.413  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.747  -1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.747   1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.413   0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.457  -1.593   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.457   1.593   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.080  -1.540   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       9.852  -0.802   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       9.852   0.802   0.000  0.00  0.00           C+0
CONECT    1    6                                                            
CONECT    2    7                                                            
CONECT    3    4    6    9                                                  
CONECT    4    3    7   10                                                  
CONECT    5    6    8   11                                                  
CONECT    6    1    3    5                                                  
CONECT    7    2    4    8                                                  
CONECT    8    5    7                                                       
CONECT    9    3   12                                                       
CONECT   10    4   13                                                       
CONECT   11    5                                                            
CONECT   12    9   13                                                       
CONECT   13   10   12                                                       
MASTER        0    0    0    0    0    0    0    0   13    0   28    0
END

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

Molecular Formula

C₁₁H₈O₂

Average Mass

172.18

Monoisotopic Mass

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 )

Functional Ontology

Not Available

Physical Properties

State

Solid

Predicted Properties

Property	Value	Source
Water Solubility	0.5 g/L	ALOGPS
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	No	ChemAxon

Spectra

Not Available

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood
Fibroblasts
Kidney
Liver
Neuron
Pancreas
Placenta
Platelet
Prostate
Urine

Tissue Locations

Fibroblasts
Kidney
Liver
Neuron
Pancreas
Placenta
Platelet
Prostate

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species
MMDBp0191749	Dehydrogenase/reductase SDR family member 4	Enzyme	Q9BTZ2	Homo sapiens
MMDBp0191797	Aldehyde oxidase	Unknown	Q06278	Homo sapiens
MMDBp0191809	Ribosyldihydronicotinamide dehydrogenase [quinone]	Unknown	P16083	Homo sapiens
MMDBp0191852	Xanthine dehydrogenase/oxidase	Unknown	P47989	Homo sapiens
MMDBp0191854	NADPH--cytochrome P450 reductase	Unknown	P16435	Homo sapiens
MMDBp0191859	Methylenetetrahydrofolate reductase	Unknown	P42898	Homo sapiens
MMDBp0192775	Activin receptor type-1	Unknown	Q04771	Homo sapiens
MMDBp0193099	Cytochrome P450 2E1	Unknown	P05181	Homo sapiens
MMDBp0193110	Cytochrome P450 1A1	Unknown	P04798	Homo sapiens
MMDBp0193115	Cytochrome P450 1A2	Unknown	P05177	Homo sapiens
MMDBp0193122	Cytochrome P450 2A6	Unknown	P11509	Homo sapiens
MMDBp0193201	NAD(P)H dehydrogenase [quinone] 1	Unknown	P15559	Homo sapiens
MMDBp0193203	Vitamin K-dependent gamma-carboxylase	Unknown	P38435	Homo sapiens
MMDBp0193228	Coagulation factor IX	Unknown	P00740	Homo sapiens
MMDBp0193371	Vitamin K-dependent protein C	Unknown	P04070	Homo sapiens
MMDBp0193372	Vitamin K-dependent protein S	Enzyme	P07225	Homo sapiens
MMDBp0193373	Vitamin K-dependent protein Z	Enzyme	P22891	Homo sapiens
MMDBp0193374	Osteocalcin	Unknown	P02818	Homo sapiens
MMDBp0193377	Coagulation factor X	Unknown	P00742	Homo sapiens
MMDBp0193379	Coagulation factor VII	Unknown	P08709	Homo sapiens
MMDBp0193465	Vitamin K epoxide reductase complex subunit 1	Enzyme	Q9BQB6	Homo sapiens
MMDBp0195049	NADPH-dependent diflavin oxidoreductase 1	Unknown	Q9UHB4	Homo sapiens
MMDBp0196222	Vitamin K epoxide reductase complex subunit 1-like protein 1	Enzyme	Q8N0U8	Homo sapiens

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria/Eubacteria	Proteobacteria	1	Human ; Human feces; Human feces; pleural fluid plaque; bal; Human stool	Unknown

Exposure Sources

Other Exposures

Source Type	Data Source	Reference
Drugs	U.S. Environmental Protection Agency	CompTox
Drugs - Antimicrobial	U.S. Environmental Protection Agency	CompTox
Cosmetics	U.S. Environmental Protection Agency	CompTox
Domestics	U.S. Environmental Protection Agency	CompTox
Domestics	U.S. Environmental Protection Agency	CompTox
Cosmetics	U.S. Environmental Protection Agency	CompTox

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference
Human Urine	Detected and Quantified	0.000411	0.0001	0.0011	umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	15722567
Human Urine	Detected and Quantified	0.00108	0.0003	0.025	umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	15722567
Human Fibroblasts	Detected but not Quantified					Not Specified	Not Specified	Normal	HMDB	34986597
Human Kidney	Detected but not Quantified					Not Specified	Not Specified	Normal	HMDB	34986597
Human Liver	Detected but not Quantified					Not Specified	Not Specified	Normal	HMDB	34986597
Human Neuron	Detected but not Quantified					Not Specified	Not Specified	Normal	HMDB	34986597
Human Pancreas	Detected but not Quantified					Not Specified	Not Specified	Normal	HMDB	34986597
Human Placenta	Detected but not Quantified					Not Specified	Not Specified	Normal	HMDB	34986597
Human Platelet	Detected but not Quantified					Not Specified	Not Specified	Normal	HMDB	34986597
Human Prostate	Detected but not Quantified					Not Specified	Not Specified	Normal	HMDB	34986597
Human Blood	Detected but not Quantified								HMDB

External Links

HMDB ID

HMDB0001892

DrugBank ID

DB00170

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB000953

KNApSAcK ID

Not Available

Chemspider ID

3915

KEGG Compound ID

C05377

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Menadione

METLIN ID

3910

PubChem Compound

4055

PDB ID

Not Available

ChEBI ID

28869

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

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 ]
Robertson DG, Bailey DL, Martin RA: Species differences in response to photohemolytic agents. Photochem Photobiol. 1991 Apr;53(4):455-61. doi: 10.1111/j.1751-1097.1991.tb03656.x. [PubMed:1857739 ]
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. doi: 10.1111/j.1447-0756.1991.tb00257.x. [PubMed:2064595 ]
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. doi: 10.1093/ajcn/51.5.846. [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. doi: 10.1016/0006-2952(86)90271-6. [PubMed:3083821 ]
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. doi: 10.1079/bjn19960115. [PubMed:8785182 ]
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. doi: 10.1007/s002040050364. [PubMed:9010592 ]
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 ]
Suzuki S, Iwata G, Sutor AH: Vitamin K deficiency during the perinatal and infantile period. Semin Thromb Hemost. 2001;27(2):93-8. doi: 10.1055/s-2001-14066. [PubMed:11372776 ]
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. doi: 10.1385/mo:20:1:45. [PubMed:12665684 ]
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. doi: 10.1016/s0306-4522(03)00382-8. [PubMed:12895502 ]
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. doi: 10.1001/jama.292.3.358. [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. doi: 10.1194/jlr.D400033-JLR200. Epub 2005 Feb 1. [PubMed:15722567 ]
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. doi: 10.1016/j.freeradbiomed.2005.04.029. [PubMed:16109308 ]
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. doi: 10.1016/j.bbrc.2005.08.129. [PubMed:16140270 ]

Showing metabocard for Menaquinone (MMDBc0029791)

MOL for #<Metabolite:0x00007f9226100490>

3D MOL for #<Metabolite:0x00007f9226100490>

3D SDF for #<Metabolite:0x00007f9226100490>

3D-SDF for #<Metabolite:0x00007f9226100490>

PDB for #<Metabolite:0x00007f9226100490>

3D PDB for #<Metabolite:0x00007f9226100490>

SMILES for #<Metabolite:0x00007f9226100490>

INCHI for #<Metabolite:0x00007f9226100490>

Structure for #<Metabolite:0x00007f9226100490>

3D Structure for #<Metabolite:0x00007f9226100490>