Identification
YMDB IDYMDB01526
NamePhylloquinone
SpeciesSaccharomyces cerevisiae
StrainBrewer's yeast
DescriptionVitamin K1, also known as phytonadione or mephyton, belongs to the class of organic compounds known as vitamin k compounds. These are quinone lipids containing a methylated naphthoquinone ring structure, and vary in the aliphatic side chain attached at the 3-position. Vitamin K1 is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Thumb
Synonyms
  • 1,4-Naphthoquinone, 2-methyl-3-phytyl-
  • 2-Methyl-3-phythyl-1,4-naphthochinon
  • 2-Methyl-3-phytyl-1,4-naphthochinon
  • 2-methyl-3-phytyl-1,4-naphthoquinone
  • 2-Methyl-3-phytyl-1,4-napthoquinone
  • 2', 3'-trans-Vitamin K1
  • 2',3'-trans-Vitamin K1
  • 3-Phytylmenadione
  • a-Phylloquinone
  • alpha-Phylloquinone
  • Fitomenadiona
  • Fitomenadione
  • Kephton
  • Kinadion
  • Konakion
  • Mephyton
  • Mono-Kay
  • Monodion
  • Phyllochinon
  • Phyllochinonum
  • Phylloquinone
  • Phythyl-menadion
  • Phytomenadione
  • Phytomenadionum
  • Phytonadione
  • Phytonadionum
  • Phytylmenadione
  • trans-Phylloquinone
  • Vitamin K
  • vitamin k1
  • Vitamin K1 (VAN)
  • Vitamin K1(20)
  • 2-Methyl-3-[(2E,7R,11R)-3,7,11,15-tetramethylhexadec-2-en-1-yl]naphthalene-1,4-dione
  • Antihemorrhagic vitamin
  • Aqua mephyton
  • Aqua-mephytin
  • Aquamephyton
  • Combinal K1
  • K-Ject
  • Kativ N
  • Synthex P
  • Vitamin K 1
  • Phyllohydroquinone
CAS number84-80-0
WeightAverage: 450.6957
Monoisotopic: 450.349780716
InChI KeyMBWXNTAXLNYFJB-UHFFFAOYSA-N
InChIInChI=1S/C31H46O2/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/h7-8,18-20,22-24H,9-17,21H2,1-6H3
IUPAC Name2-methyl-3-[(2E)-3,7,11,15-tetramethylhexadec-2-en-1-yl]-1,4-dihydronaphthalene-1,4-dione
Traditional IUPAC Namevitamin k1
Chemical FormulaC31H46O2
SMILESCC(C)CCCC(C)CCCC(C)CCCC(C)=CCC1=C(C)C(=O)C2=CC=CC=C2C1=O
Chemical Taxonomy
Description belongs to the class of organic compounds known as vitamin k compounds. These are quinone lipids containing a methylated naphthoquinone ring structure, and vary in the aliphatic side chain attached at the 3-position.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassQuinone and hydroquinone lipids
Direct ParentVitamin K compounds
Alternative Parents
Substituents
  • 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
Physical Properties
StateSolid
Charge0
Melting point-20 °C
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility5.9e-05 g/LALOGPS
logP8.48ALOGPS
logP9.7ChemAxon
logS-6.9ALOGPS
pKa (Strongest Basic)-7.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area34.14 ŲChemAxon
Rotatable Bond Count14ChemAxon
Refractivity142.96 m³·mol⁻¹ChemAxon
Polarizability56.8 ųChemAxon
Number of Rings2ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular LocationsNot Available
Organoleptic PropertiesNot Available
SMPDB PathwaysNot Available
KEGG PathwaysNot Available
SMPDB ReactionsNot Available
KEGG ReactionsNot Available
Concentrations
Intracellular ConcentrationsNot Available
Extracellular Concentrations
Intracellular ConcentrationSubstrateGrowth ConditionsStrainCitation
0.009 ± 0.0 µM grape juiceanaerobicBrewer's yeastAlcoholic beverage, wine, table, red - U.S. Department of Agriculture, Agricultural Research Service. 2010. USDA National Nutrient Database for Standard Reference, Release 23. Nutrient Data Laboratory Home Page
Conversion Details Here
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-000i-6895400000-254b168b019b1fc92c97JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0121900000-22d50aa41f7e3fa9b9daJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0apr-1679100000-60b28d715716b428496dJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4j-6592000000-1898f88b8876c5be2ea3JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0000900000-20c987b9d7c887aaedeaJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-0101900000-ad51a9cf10696cc2c1ccJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0089-2924500000-7863f3ba8e25eb26d7e0JSpectraViewer
MSMass Spectrum (Electron Ionization)splash10-0ug0-9860500000-a5cd1646f1fc838bc7d7JSpectraViewer | MoNA
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
References
References:
  • Alcoholic beverage, wine, table, red - U.S. Department of Agriculture, Agricultural Research Service. 2010. USDA National Nutrient Database for Standard Reference, Release 23. Nutrient Data Laboratory Home Page
Synthesis Reference:Araki, Shin; Murasawa, Hisashi; Tamura, Masanori. Manufacture of vitamin K with Bacillus natto and liquid media for it. Jpn. Kokai Tokkyo Koho (2002), 5 pp.
External Links:
ResourceLink
CHEBI ID18067
HMDB IDHMDB03555
Pubchem Compound ID5280483
Kegg IDC02059
ChemSpider ID4647
FOODB IDFDB012357
Wikipedia IDPhytomenadione
BioCyc ID3-HYDROXY-2-METHYL-3-PHYTYL-23-DIHYDRONA