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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:34:12 UTC
Update Date2019-07-23 06:05:25 UTC
HMDB IDHMDB0030020
Secondary Accession Numbers
  • HMDB30020
Metabolite Identification
Common NameWithanolide B
DescriptionMenatetrenone, also known as vitamin K2 or menaquinone 4, 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. Menatetrenone is an extremely weak basic (essentially neutral) compound (based on its pKa).
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
MenaquinonesMeSH
Vitamin K quinoneMeSH
Vitamin K 2MeSH
MenaquinoneMeSH
Lycium substance bHMDB
Chemical FormulaC28H38O5
Average Molecular Weight454.5983
Monoisotopic Molecular Weight454.271924326
IUPAC Name15-[1-(4,5-dimethyl-6-oxo-3,6-dihydro-2H-pyran-2-yl)ethyl]-5-hydroxy-10,14-dimethyl-3-oxapentacyclo[9.7.0.0²,⁴.0⁵,¹⁰.0¹⁴,¹⁸]octadec-7-en-9-one
Traditional Name15-[1-(4,5-dimethyl-6-oxo-2,3-dihydropyran-2-yl)ethyl]-5-hydroxy-10,14-dimethyl-3-oxapentacyclo[9.7.0.0²,⁴.0⁵,¹⁰.0¹⁴,¹⁸]octadec-7-en-9-one
CAS Registry Number56973-41-2
SMILES
CC(C1CCC2C3C4OC4C4(O)CC=CC(=O)C4(C)C3CCC12C)C1CC(C)=C(C)C(=O)O1
InChI Identifier
InChI=1S/C28H38O5/c1-14-13-20(32-25(30)15(14)2)16(3)17-8-9-18-22-19(10-12-26(17,18)4)27(5)21(29)7-6-11-28(27,31)24-23(22)33-24/h6-7,16-20,22-24,31H,8-13H2,1-5H3
InChI KeyZTEVDTFJUUJBLP-UHFFFAOYSA-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

Biological location:

Route of exposure:

Source:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point260 - 265 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.004 g/LALOGPS
logP3.51ALOGPS
logP4.78ChemAxon
logS-5.1ALOGPS
pKa (Strongest Acidic)13.1ChemAxon
pKa (Strongest Basic)-3.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area76.13 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity125.5 m³·mol⁻¹ChemAxon
Polarizability51.52 ųChemAxon
Number of Rings6ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-02br-3594800000-342201064ab3ced44f46Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-03dr-7395750000-310dbfd34ec4e713cd0dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0005900000-688ecb047eeaf70aecd1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000l-4019400000-c975545f7209b4f8488aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0uy3-8439300000-f0185769a0d0164097ddSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0005900000-688ecb047eeaf70aecd1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000l-4019400000-c975545f7209b4f8488aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0uy3-8439300000-f0185769a0d0164097ddSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0001900000-88b2d268530467097752Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0zfr-1002900000-fdadf8b6714187301cf8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014r-9104200000-bdd23549b698a72f5ac1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0001900000-88b2d268530467097752Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0zfr-1002900000-fdadf8b6714187301cf8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014r-9104200000-bdd23549b698a72f5ac1Spectrum
Biological Properties
Cellular Locations
  • Extracellular
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
MarkerDB ID
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.