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Record Information
Version1.0
Creation Date2009-07-21 20:28:11 UTC
Update Date2016-10-28 10:03:09 UTC
Accession NumberCHEM002322
Identification
Common NamePhytonadione
ClassSmall Molecule
DescriptionPhylloquinone is often called vitamin K1. It is a fat-soluble vitamin that is stable to air and moisture but decomposes in sunlight. It is found naturally in a wide variety of green plants. Phylloquinone is also an antidote for coumatetralyl. Vitamin K is needed for the posttranslational modification of certain proteins, mostly required for blood coagulation.
Contaminant Sources
  • Cosmetic Chemicals
  • FooDB Chemicals
  • HMDB Contaminants - Urine
  • IARC Carcinogens Group 3
  • STOFF IDENT Compounds
  • T3DB toxins
  • ToxCast & Tox21 Chemicals
Contaminant Type
  • Antifibrinolytic Agent
  • Drug
  • Ester
  • Food Toxin
  • Metabolite
  • Organic Compound
  • Synthetic Compound
  • Vitamin
  • Vitamin K
Chemical Structure
Thumb
Synonyms
ValueSource
2-Methyl-3-(3,7,11,15-tetramethyl-2-hexadecenyl)-1,4-naphthalenedioneChEBI
2-Methyl-3-[(2E)-3,7,11,15-tetramethyl-2-hexadecenyl]naphthoquinoneChEBI
2-Methyl-3-phytyl-1,4-naphthochinonChEBI
2-Methyl-3-phytyl-1,4-naphthoquinoneChEBI
3-PhytylmenadioneChEBI
alpha-PhylloquinoneChEBI
FitomenadionaChEBI
PhyllochinonChEBI
PhyllochinonumChEBI
PhytomenadioneChEBI
PhytomenadionumChEBI
PhytonadioneChEBI
PhytonadionumChEBI
PhytylmenadioneChEBI
trans-PhylloquinoneChEBI
a-PhylloquinoneGenerator
Α-phylloquinoneGenerator
Vitamin K hydroquinone (phylloquinone)HMDB
PhyllohydroquinoneHMDB
PhylloquinoneHMDB
AquamephytonHMDB
KonakionHMDB
Vitamin K 1HMDB
2',3'-trans-Vitamin K1HMDB
2’,3’-trans-vitamin K1HMDB
Vitamin K1ChEBI
Chemical FormulaC31H46O2
Average Molecular Mass450.696 g/mol
Monoisotopic Mass450.350 g/mol
CAS Registry Number84-80-0
IUPAC Name2-methyl-3-[(2E,7R,11R)-3,7,11,15-tetramethylhexadec-2-en-1-yl]-1,4-dihydronaphthalene-1,4-dione
Traditional Namevitamin K
SMILESCC(C)CCC[C@@H](C)CCC[C@@H](C)CCC\C(C)=C\CC1=C(C)C(=O)C2=C(C=CC=C2)C1=O
InChI IdentifierInChI=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+/t23-,24-/m1/s1
InChI KeyMBWXNTAXLNYFJB-NKFFZRIASA-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
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Extracellular
  • Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological Roles
Chemical RolesNot Available
Physical Properties
StateLiquid
AppearanceNot Available
Experimental Properties
PropertyValue
Melting Point-20°C
Boiling Point142.5°C at 1.00E-03 mm Hg
SolubilityInsoluble in water
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
Polarizability55.92 ųChemAxon
Number of Rings2ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MSsplash10-002r-2930000000-2b32596edebbe7e02cf7View in MoNA
GC-MSGC-MS Spectrum - GC-MS (1 TMS)splash10-0002-1290000000-fa752c2db990f115c3c6View in MoNA
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-0002-8269080000-4bdc9b3a41d7d08b7265View in MoNA
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-0002-7379080000-ba90762b738ee84b3151View in MoNA
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-014i-6749020000-c4e58ef0e538e224dad4View in MoNA
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-0g4i-3149020000-ad93d4a26002eefa74ceView in MoNA
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-00xr-5397040000-221a2f93d46494325e33View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MSsplash10-000i-6895400000-254b168b019b1fc92c97View in MoNA
GC-MSGC-MS Spectrum - EI-Bsplash10-0udl-9740400000-e47d11ed7b15a667d611View in MoNA
GC-MSGC-MS Spectrum - EI-Bsplash10-0udi-2540900000-d08585615fbc2418786aView in MoNA
GC-MSGC-MS Spectrum - GC-MSsplash10-002r-2930000000-2b32596edebbe7e02cf7View in MoNA
GC-MSGC-MS Spectrum - GC-MSsplash10-0002-1290000000-fa752c2db990f115c3c6View in MoNA
GC-MSGC-MS Spectrum - GC-MSsplash10-0002-8269080000-4bdc9b3a41d7d08b7265View in MoNA
GC-MSGC-MS Spectrum - GC-MSsplash10-0002-7379080000-ba90762b738ee84b3151View in MoNA
GC-MSGC-MS Spectrum - GC-MSsplash10-014i-6749020000-c4e58ef0e538e224dad4View in MoNA
GC-MSGC-MS Spectrum - GC-MSsplash10-0g4i-3149020000-ad93d4a26002eefa74ceView in MoNA
GC-MSGC-MS Spectrum - GC-MSsplash10-00xr-5397040000-221a2f93d46494325e33View in MoNA
GC-MSGC-MS Spectrum - GC-MSsplash10-002r-2930000000-2b32596edebbe7e02cf7View in MoNA
GC-MSGC-MS Spectrum - GC-MSsplash10-0002-1290000000-fa752c2db990f115c3c6View in MoNA
GC-MSGC-MS Spectrum - GC-MSsplash10-0002-8269080000-4bdc9b3a41d7d08b7265View in MoNA
GC-MSGC-MS Spectrum - GC-MSsplash10-0002-7379080000-ba90762b738ee84b3151View in MoNA
GC-MSGC-MS Spectrum - GC-MSsplash10-014i-6749020000-c4e58ef0e538e224dad4View in MoNA
GC-MSGC-MS Spectrum - GC-MSsplash10-0g4i-3149020000-ad93d4a26002eefa74ceView in MoNA
GC-MSGC-MS Spectrum - GC-MSsplash10-00xr-5397040000-221a2f93d46494325e33View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0121900000-22d50aa41f7e3fa9b9daView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0apr-1679100000-60b28d715716b428496dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4j-6592000000-1898f88b8876c5be2ea3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0000900000-20c987b9d7c887aaedeaView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-0101900000-ad51a9cf10696cc2c1ccView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0089-2924500000-7863f3ba8e25eb26d7e0View in MoNA
Toxicity Profile
Route of ExposureSubcutaneous, Intramuscular, Intravenous injection. Oral phylloquinone is adequately absorbed from the gastrointestinal tract only if bile salts are present. After absorption, phylloquinone is initially concentrated in the liver, but the concentration declines rapidly. Very little vitamin K accumulates in tissues.
Mechanism of ToxicityVitamin K is an essential cofactor for the gamma-carboxylase enzymes which catalyze the posttranslational gamma-carboxylation of glutamic acid residues in inactive hepatic precursors of coagulation factors II (prothrombin), VII, IX and X. Gamma-carboxylation converts these inactive precursors into active coagulation factors which are secreted by hepatocytes into the blood. Supplementing with Phylloquinone results in a relief of vitamin K deficiency symptoms which include easy bruisability, epistaxis, gastrointestinal bleeding, menorrhagia and hematuria.
Metabolism Route of Elimination: Almost no free unmetabolized vitamin K appears in bile or urine.
Toxicity ValuesLD50: 41.5 mL/kg at 0.2% (Intravenous, Mouse) (1) LD50: 52 mL/kg at 1% (Intravenous, Mouse) (1)
Lethal DoseNot Available
Carcinogenicity (IARC Classification)3, not classifiable as to its carcinogenicity to humans. (3)
Uses/SourcesFor the treatment of haemorrhagic conditions in infants, antidote for coumarin anticoagulants in hypoprothrombinaemia.
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDDB01022
HMDB IDHMDB0003555
FooDB IDFDB023333
Phenol Explorer IDNot Available
KNApSAcK IDC00002868
BiGG IDNot Available
BioCyc IDNot Available
METLIN ID7027
PDB IDNot Available
Wikipedia LinkPhytonadione
Chemspider ID4444392
ChEBI ID18067
PubChem Compound ID5284607
Kegg Compound IDC05850
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis Reference

Manfred Dorner, “Method of making vitamin K1.” U.S. Patent US5744624, issued June, 1964.

MSDSLink
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=11003724
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=15686525
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=19588895
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=19996170
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=21169510
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=21645693
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=21844348
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=21914559
9. 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.
10. Hirauchi K, Sakano T, Nagaoka T, Morimoto A: Simultaneous determination of vitamin K1, vitamin K1 2,3-epoxide and menaquinone-4 in human plasma by high-performance liquid chromatography with fluorimetric detection. J Chromatogr. 1988 Aug 19;430(1):21-9.
11. Shearer MJ, Mallinson CN, Webster GR, Barkhan P: Absorption of tritiated vitamin K1 in patients with fat malabsorption. Gut. 1970 Dec;11(12):1063-4.
12. Huang Y, Zhang C, Zhang X, Zhang Z: Chemiluminescence analysis of menadione sodium bisulfite and analgin in pharmaceutical preparations and biological fluids. J Pharm Biomed Anal. 1999 Dec;21(4):817-25.
13. Begley GS, Furie BC, Czerwiec E, Taylor KL, Furie GL, Bronstein L, Stenflo J, Furie B: A conserved motif within the vitamin K-dependent carboxylase gene is widely distributed across animal phyla. J Biol Chem. 2000 Nov 17;275(46):36245-9.
14. de Moerloose P, Boehlen F: [Haemostasis. A search for an ideal antithrombotics agent]. Rev Med Suisse. 2005 Jan 5;1(1):35-8.
15. Gover PA, Ingram GI, Cork MS, Holland L, Hopkins RP, Callaghan P, Barkhan P, Shearer MJ: Bleeding from self-administration of phenindione: a detailed case study. Br J Haematol. 1976 Aug;33(4):551-64.
16. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9.
17. 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.
18. 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.
19. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621.
20. The lipid handbook with CD-ROM