Showing metabocard for Vitamin K1 (BMDB0003555)

IdentificationTaxonomyPhysical propertiesSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-09-30 23:05:17 UTC
Update Date2020-06-04 20:41:12 UTC
MCDB ID BMDB0003555
Secondary Accession Numbers
  • BMDB03555
Metabolite Identification
Common NameVitamin K1
DescriptionPhylloquinone, also known as mephyton or vitamin K1, 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. Phylloquinone exists as a solid, possibly soluble (in water), and an extremely weak basic (essentially neutral) compound (based on its pKa) molecule. Phylloquinone exists in all living species, ranging from bacteria to humans.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
PhytonadioneKegg
2-Methyl-3-phytyl-1,4-naphthoquinoneKegg
PhytomenadioneKegg
MephytonKegg
2',3'-trans-Vitamin K1HMDB
2-Methyl-3-phythyl-1,4-naphthochinonHMDB
2-Methyl-3-phytyl-1,4-naphthochinonHMDB
2-Methyl-3-phytyl-1,4-napthoquinoneHMDB
2-Methyl-3-[(2E,7R,11R)-3,7,11,15-tetramethylhexadec-2-en-1-yl]naphthalene-1,4-dioneHMDB
3-PhytylmenadioneHMDB
a-PhylloquinoneHMDB
alpha-PhylloquinoneHMDB
Antihemorrhagic vitaminHMDB
Aqua mephytonHMDB
Aqua-mephytinHMDB
AquamephytonHMDB, MeSH
Combinal K1HMDB
FitomenadionaHMDB
FitomenadioneHMDB
K-JectHMDB
Kativ NHMDB
KephtonHMDB
KinadionHMDB
KonakionHMDB, MeSH
mono-KayHMDB
MonodionHMDB
PhyllochinonHMDB
PhyllochinonumHMDB
PhylloquinoneHMDB
Phythyl-menadionHMDB
PhytomenadionumHMDB
PhytonadionumHMDB
PhytylmenadioneHMDB
Synthex PHMDB
trans-PhylloquinoneHMDB
Vitamin K 1MeSH, HMDB
PhyllohydroquinoneMeSH, HMDB
Vitamin K1KEGG
Vitamin KMeSH, HMDB
Chemical FormulaC31H46O2
Average Molecular Weight450.6957
Monoisotopic Molecular Weight450.349780716
IUPAC Name2-methyl-3-[(2E)-3,7,11,15-tetramethylhexadec-2-en-1-yl]-1,4-dihydronaphthalene-1,4-dione
Traditional Namevitamin k1
CAS Registry Number12001-79-5
SMILES
CC(C)CCCC(C)CCCC(C)CCC\C(C)=C\CC1=C(C)C(=O)C2=CC=CC=C2C1=O
InChI Identifier
InChI=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/b25-20+
InChI KeyMBWXNTAXLNYFJB-LKUDQCMESA-N
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
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
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 FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-000i-6895400000-254b168b019b1fc92c972017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0121900000-22d50aa41f7e3fa9b9da2016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0apr-1679100000-60b28d715716b428496d2016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4j-6592000000-1898f88b8876c5be2ea32016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0000900000-20c987b9d7c887aaedea2016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-0101900000-ad51a9cf10696cc2c1cc2016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0089-2924500000-7863f3ba8e25eb26d7e02016-08-03View Spectrum
MSMass Spectrum (Electron Ionization)splash10-0ug0-9860500000-a5cd1646f1fc838bc7d72014-09-20View Spectrum
1D NMR1H NMR Spectrum (1D, 90 MHz, CDCl3, experimental)Not Available2014-09-20View Spectrum
Concentrations
StatusValueReferenceDetails
Detected and Quantified0.0109 uM details
Detected and Quantified0.00888 - 0.0399 uM
  • NRC. 1989. Recomm...
 details
Detected and Quantified0.0178 uM details
Detected and Quantified0.00222 uM details
Detected and Quantified0.00666 uM details
Detected and Quantified0.00222 uM details
Detected and Quantified0.00222 uM details
Detected and Quantified0.00444 uM details
Detected and Quantified0.00444 uM details
Detected and Quantified0.00666 uM details
Detected and Quantified0.00666 uM details
Detected and Quantified0.00888 - 0.0399 uM details
Detected and Quantified0.002 +/- 0.001 uM details
Detected and Quantified0.004 +/- 0.001 uM details
Detected and Quantified0.0042 +/- 0.0004 uM details
Detected and Quantified0.002 +/- 0.001 uM details
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB012357
KNApSAcK IDC00002868
Chemspider IDNot Available
KEGG Compound IDC02059
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkPhytomenadione
METLIN IDNot Available
PubChem Compound5280483
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceAraki, Shin; Murasawa, Hisashi; Tamura, Masanori. Manufacture of vitamin K with Bacillus natto and liquid media for it. Jpn. Kokai Tokkyo Koho (2002), 5 pp.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Haroon Y, Shearer MJ, Rahim S, Gunn WG, McEnery G, Barkhan P: The content of phylloquinone (vitamin K1) in human milk, cows' milk and infant formula foods determined by high-performance liquid chromatography. J Nutr. 1982 Jun;112(6):1105-17. doi: 10.1093/jn/112.6.1105. [PubMed:7086539 ]
  2. Gaucheron F: Milk and dairy products: a unique micronutrient combination. J Am Coll Nutr. 2011 Oct;30(5 Suppl 1):400S-9S. [PubMed:22081685 ]
  3. NA (1989). NRC. 1989. Recommended Dietary Allowances. 10th ed. Natl. Acad. Press, Washington, DC.. The National Academies Press.
  4. A. Foroutan et al. (2019). A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation). Journal of Agricultural and Food Chemistry.
  5. USDA Food Composition Databases [Link]