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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:34:11 UTC
Update Date2019-07-23 06:05:25 UTC
HMDB IDHMDB0030017
Secondary Accession Numbers
  • HMDB30017
Metabolite Identification
Common NameMenatetrenone
DescriptionMenatetrenone, also known as MK-4, is a vitamin K compound used as a hemostatic agent, and also as adjunctive therapy for the pain of osteoporosis. Menatetrenone is one of the nine forms of vitamin K2 and is a short-chain menaquinone. MK-4 is produced via conversion of vitamin K1 in the body, in the testes, pancreas and arterial walls (Wikipedia). Vitamin K2 is found in brassicas. Vitamin K2 is widely distributed in green leaves and vegetables. It is a fat-soluble dietary factor effective in controlling blood coagulation. All members of the vitamin K group of vitamins share a methylated naphthoquinone ring structure and vary in the aliphatic side chain attached at the 3-position. Phylloquinone (also known as vitamin K1) invariably contains in its side chain four isoprenoid residues, one of which is unsaturated. Human milk contains between 1 and 4 micrograms/litre of vitamin K1, while formula-derived milk can contain up to 100 micrograms/litre in supplemented formulas. Vitamin K2 concentrations in human milk appear to be much lower than those of vitamin K1. It is estimated that there is a 0.25 to 1.7 percent occurrence of vitamin K deficiency bleeding in the first week of the infant's life with a prevalence of 2-10 cases per 100,000 births. The biochemistry of how vitamin K is used to convert glutamic acid (Glu) to gamma-carboxyglutamic acid (Gla) has been elucidated over the past thirty years in academic laboratories throughout the world. Within the cell, vitamin K undergoes electron reduction to a reduced form of vitamin K (called vitamin K hydroquinone) by the enzyme vitamin K epoxide reductase (or VKOR). Another enzyme then oxidizes vitamin K hydroquinone to allow carboxylation of Glu to Gla; this enzyme is called the gamma-glutamyl carboxylase or the vitamin K-dependent carboxylase. The carboxylation reaction will only proceed if the carboxylase enzyme is able to oxidize vitamin K hydroquinone to vitamin K epoxide at the same time. The carboxylation and epoxidation reactions are said to be coupled reactions. Vitamin K epoxide is then re-converted into vitamin K by the vitamin K epoxide reductase. These two enzymes comprise the so-called vitamin K cycle. Vitamin K2 is one of the reasons why vitamin K is rarely deficient in a human diet (vitamin K is continually recycled in our cells). Vitamin K1 is also known as phylloquinone or phytomenadione (also called phytonadione). Vitamin K2 (menaquinone, menatetrenone) is normally produced by bacteria in the large intestine, and dietary deficiency is extremely rare unless the intestines are heavily damaged or are unable to absorb the molecule, or due to decreased production by normal flora, as seen in broad spectrum antibiotic use.
Structure
Data?1563861925
Synonyms
ValueSource
2-Methyl-3-(3,7,11,15-tetramethyl-2,6,10,14-hexadecatetraenyl)-1,4-naphthoquinoneChEBI
2-Methyl-3-geranylgeranyl-1,4-naphthoquinoneChEBI
2-Methyl-3-trans-tetraprenyl-1,4-naphthoquinoneChEBI
Menaquinone 4ChEBI
Menaquinone K4ChEBI
Menaquinone-4ChEBI
MenatetrenonaChEBI
MenatetrenonumChEBI
MK-4ChEBI
MK4ChEBI
Vitamin K2ChEBI
Vitamin MK 4ChEBI
2-Methyl-3-all-trans-tetraprenyl-1,4-naphthoquinoneHMDB
Vitamin K2(20)HMDB
Kefton-2HMDB
(e,e,e)-Isomer OF menatetrenoneHMDB
Vitamin MK-4HMDB
Vitamin K 2MeSH
Vitamin K quinoneMeSH
MenaquinoneMeSH
MenaquinonesMeSH
Chemical FormulaC31H40O2
Average Molecular Weight444.659
Monoisotopic Molecular Weight444.302830528
IUPAC Name2-methyl-3-[(2E,6E,10E)-3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraen-1-yl]-1,4-dihydronaphthalene-1,4-dione
Traditional Namemenatetrenone
CAS Registry Number863-61-6
SMILES
CC(C)=CCC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CC1=C(C)C(=O)C2=CC=CC=C2C1=O
InChI Identifier
InChI=1S/C31H40O2/c1-22(2)12-9-13-23(3)14-10-15-24(4)16-11-17-25(5)20-21-27-26(6)30(32)28-18-7-8-19-29(28)31(27)33/h7-8,12,14,16,18-20H,9-11,13,15,17,21H2,1-6H3/b23-14+,24-16+,25-20+
InChI KeyDKHGMERMDICWDU-GHDNBGIDSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as menaquinones. These are vitamin K2 compounds consisting of a naphtho-1,4-quinone ring system, which is substituted at the 2-position by an isoprenyl side-chain, and usually, at the 3-position by a methyl group.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassQuinone and hydroquinone lipids
Direct ParentMenaquinones
Alternative Parents
Substituents
  • Menaquinone
  • Diterpenoid
  • Naphthoquinone
  • Naphthalene
  • Aryl ketone
  • Quinone
  • Benzenoid
  • Ketone
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic homopolycyclic compound
Molecular FrameworkAromatic homopolycyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Biological location:

Source:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.00027 g/LALOGPS
logP7.24ALOGPS
logP8.48ChemAxon
logS-6ALOGPS
pKa (Strongest Basic)-7.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area34.14 ŲChemAxon
Rotatable Bond Count11ChemAxon
Refractivity145.51 m³·mol⁻¹ChemAxon
Polarizability54.92 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-014l-9430000000-936e4020e35c79ab80a8Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-014l-9430000000-936e4020e35c79ab80a8Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-003r-7891050000-fb45abd0445fd13b3287Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0221900000-da2fa06091b3f02f7f62Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0550-0968100000-d9351f8233d2638c6648Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014i-9673000000-f5a80c46af487a0ae786Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0000900000-a5b1daed1e13ae9cdc49Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-0101900000-63826c82750026b58641Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00fr-2925400000-e48e5e86379a4048f95eSpectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB12148
Phenol Explorer Compound IDNot Available
FooDB IDFDB029792
KNApSAcK IDNot Available
Chemspider ID4445530
KEGG Compound IDC00828
BioCyc IDCPD-9726
BiGG IDNot Available
Wikipedia LinkMenatetrenone
METLIN IDNot Available
PubChem Compound5282367
PDB IDNot Available
ChEBI ID78277
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  2. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
  3. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
  4. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
  5. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
  6. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Enzymes

General function:
Involved in electron carrier activity
Specific function:
The enzyme apparently serves as a quinone reductase in connection with conjugation reactions of hydroquinons involved in detoxification pathways as well as in biosynthetic processes such as the vitamin K-dependent gamma-carboxylation of glutamate residues in prothrombin synthesis.
Gene Name:
NQO1
Uniprot ID:
P15559
Molecular weight:
30867.405
Reactions
Menatetrenone + Hydrogen Ion + NADH → Menaquinol + NADdetails
General function:
Involved in vitamin-K-epoxide reductase (warfarin-sensi
Specific function:
Involved in vitamin K metabolism. Catalytic subunit of the vitamin K epoxide reductase (VKOR) complex which reduces inactive vitamin K 2,3-epoxide to active vitamin K.
Gene Name:
VKORC1
Uniprot ID:
Q9BQB6
Molecular weight:
18234.3
Reactions
2,3-Epoxymenaquinone + 1,4-Dithiothreitol → Menatetrenone + Oxidized dithiothreitol + Waterdetails