Vitamin K2 (CHEM023635)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 21:11:53 UTC
Update Date2016-11-09 01:17:45 UTC
Accession NumberCHEM023635
Identification
Common NameVitamin K2
ClassSmall Molecule
DescriptionA menaquinone whose side-chain contains 4 isoprene units in an all-trans-configuration.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
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
MenatetrenonaChEBI
MenatetrenonumChEBI
MK-4ChEBI
MK4ChEBI
Vitamin K2(20)ChEBI
Vitamin MK 4ChEBI
Vitamin K2Kegg
Menaquinone-4ChEBI
(e,e,e)-Isomer OF menatetrenoneMeSH, HMDB
2-Methyl-3-all-trans-tetraprenyl-1,4-naphthoquinoneMeSH, HMDB
Kefton-2MeSH, HMDB
Vitamin MK-4MeSH, HMDB
Vitamin K 2MeSH
Vitamin K quinoneMeSH
MenaquinoneMeSH
MenaquinonesMeSH
Chemical FormulaC41H56O2
Average Molecular Mass580.882 g/mol
Monoisotopic Mass580.428 g/mol
CAS Registry NumberNot Available
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
SMILESCC(C)=CCC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CC1=C(C)C(=O)C2=CC=CC=C2C1=O
InChI IdentifierInChI=1S/C41H56O2/c1-30(2)16-11-17-31(3)18-12-19-32(4)20-13-21-33(5)22-14-23-34(6)24-15-25-35(7)28-29-37-36(8)40(42)38-26-9-10-27-39(38)41(37)43/h9-10,16,18,20,22,24,26-28H,11-15,17,19,21,23,25,29H2,1-8H3/b31-18+,32-20+,33-22+,34-24+,35-28+
InChI KeyPFRQBZFETXBLTP-RCIYGOBDSA-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
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.00049 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
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
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 GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
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
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-2137900000-9bfb9ad4ac1145915e57Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0019-3419100000-17e116bda37eb38893dcSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-007a-3901000000-9c3d341cbd4ad0feec93Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0000900000-87177730a5d4e2d424bbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000f-0902700000-70d2be403d22d9bb2275Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-002s-2923100000-7822153ffca689168909Spectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDDB12148
HMDB IDHMDB0030017
FooDB IDFDB029792
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDCPD-9726
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkMenatetrenone
Chemspider ID4445530
ChEBI ID78277
PubChem Compound ID5282367
Kegg Compound IDC00828
YMDB IDNot Available
ECMDB IDECMDB21552
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=22692649
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=23169578
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=23346882
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=23702931
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=23832575
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=24085302
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=24138531
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=24342502
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=24426779
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=24489112
11. https://www.ncbi.nlm.nih.gov/pubmed/?term=24508562
12. https://www.ncbi.nlm.nih.gov/pubmed/?term=24630057
13. https://www.ncbi.nlm.nih.gov/pubmed/?term=24737747
14. https://www.ncbi.nlm.nih.gov/pubmed/?term=24841104
15. https://www.ncbi.nlm.nih.gov/pubmed/?term=24975215
16. https://www.ncbi.nlm.nih.gov/pubmed/?term=30753659
17. https://www.ncbi.nlm.nih.gov/pubmed/?term=31018587
18. https://www.ncbi.nlm.nih.gov/pubmed/?term=31083359
19. https://www.ncbi.nlm.nih.gov/pubmed/?term=31579595
20. https://www.ncbi.nlm.nih.gov/pubmed/?term=32086127
21. https://www.ncbi.nlm.nih.gov/pubmed/?term=32150581
22. https://www.ncbi.nlm.nih.gov/pubmed/?term=32412060
23. https://www.ncbi.nlm.nih.gov/pubmed/?term=32448576
24. https://www.ncbi.nlm.nih.gov/pubmed/?term=33051011
25. https://www.ncbi.nlm.nih.gov/pubmed/?term=33542347
26. https://www.ncbi.nlm.nih.gov/pubmed/?term=34202933
27. https://www.ncbi.nlm.nih.gov/pubmed/?term=PMC7259074
28. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9.
29. 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.
30. 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.
31. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621.
32. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.
33. The lipid handbook with CD-ROM