Tmic
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Record Information
Version2.0
Creation Date2009-07-21 20:28:11 UTC
Update Date2014-12-24 20:25:54 UTC
Accession NumberT3D2959
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.
Compound Type
  • Antifibrinolytic Agent
  • Drug
  • Ester
  • Food Toxin
  • Metabolite
  • Organic Compound
  • Synthetic Compound
  • Vitamin
  • Vitamin K
Chemical Structure
Thumb
Synonyms
Synonym
2', 3'-trans-Vitamin K1
2-Methyl-3-(3,7,11,15-tetramethyl-2-hexadecenyl)-1,4-naphthalenedione
2-Methyl-3-phythyl-1,4-naphthochinon
2-Methyl-3-phytyl-1,4-naphthochinon
2-Methyl-3-phytyl-1,4-naphthoquinone
2-Methyl-3-[(2e)-3,7,11,15-tetramethyl-2-hexadecenyl]naphthoquinone
3-Phytylmenadione
alpha-Phylloquinone
Antihemorrhagic vitamin
Aqua-Mephyton
Fitomenadiona
Konakion
Mephyton
Phyllochinon
Phyllochinonum
Phylloquinone
Phythyl-menadion
Phytomenadione
Phytomenadionum
Phytonadionum
Phytylmenadione
trans-Phylloquinone
Vitamin K
Vitamin K1
α-phylloquinone
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
SMILES[H]\C(CC1=C(C)C(=O)C2=CC=CC=C2C1=O)=C(\C)CCC[C@]([H])(C)CCC[C@]([H])(C)CCCC(C)C
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 KeyInChIKey=MBWXNTAXLNYFJB-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
LogP9.3
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-MS (Non-derivatized)splash10-002r-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
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0udl-9740400000-e47d11ed7b15a667d611View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0udi-2540900000-d08585615fbc2418786aView in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-002r-2930000000-2b32596edebbe7e02cf7View in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0002-1290000000-fa752c2db990f115c3c6View in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0002-8269080000-4bdc9b3a41d7d08b7265View in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0002-7379080000-ba90762b738ee84b3151View in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-014i-6749020000-c4e58ef0e538e224dad4View in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0g4i-3149020000-ad93d4a26002eefa74ceView in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-00xr-5397040000-221a2f93d46494325e33View in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-002r-2930000000-2b32596edebbe7e02cf7View in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0002-1290000000-fa752c2db990f115c3c6View in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0002-8269080000-4bdc9b3a41d7d08b7265View in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0002-7379080000-ba90762b738ee84b3151View in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-014i-6749020000-c4e58ef0e538e224dad4View in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0g4i-3149020000-ad93d4a26002eefa74ceView in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-00xr-5397040000-221a2f93d46494325e33View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-000i-6895400000-254b168b019b1fc92c97View 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
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
DrugBank IDDB01022
HMDB IDHMDB15157
PubChem Compound ID5284607
ChEMBL IDCHEMBL1550
ChemSpider ID4447652
KEGG IDC02059
UniProt IDNot Available
OMIM ID118650 , 122700 , 176860 , 176880 , 176930 , 188055 , 215100 , 227600 , 277450 , 306900 , 607473
ChEBI ID18067
BioCyc ID3-HYDROXY-2-METHYL-3-PHYTYL-23-DIHYDRONA
CTD IDNot Available
Stitch IDPhytonadione
PDB IDPQN
ACToR IDNot Available
Wikipedia LinkPhytonadione
References
Synthesis Reference

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

MSDSLink
General References
  1. Wishart DS, Knox C, Guo AC, Cheng D, Shrivastava S, Tzur D, Gautam B, Hassanali M: DrugBank: a knowledgebase for drugs, drug actions and drug targets. Nucleic Acids Res. 2008 Jan;36(Database issue):D901-6. Epub 2007 Nov 29. [18048412 ]
  2. Drugs.com [Link]
  3. International Agency for Research on Cancer (2014). IARC Monographs on the Evaluation of Carcinogenic Risks to Humans. [Link]
Gene Regulation
Up-Regulated GenesNot Available
Down-Regulated GenesNot Available

Targets

General Function:
Structural molecule activity
Specific Function:
Constitutes 1-2% of the total bone protein. It binds strongly to apatite and calcium.
Gene Name:
BGLAP
Uniprot ID:
P02818
Molecular Weight:
10962.445 Da
References
  1. Sato Y, Tsuru T, Oizumi K, Kaji M: Vitamin K deficiency and osteopenia in disuse-affected limbs of vitamin D-deficient elderly stroke patients. Am J Phys Med Rehabil. 1999 Jul-Aug;78(4):317-22. [10418836 ]
  2. Schurgers LJ, Dissel PE, Spronk HM, Soute BA, Dhore CR, Cleutjens JP, Vermeer C: Role of vitamin K and vitamin K-dependent proteins in vascular calcification. Z Kardiol. 2001;90 Suppl 3:57-63. [11374034 ]
  3. Vermeer C, Wolf J, Craciun AM, Knapen MH: Bone markers during a 6-month space flight: effects of vitamin K supplementation. J Gravit Physiol. 1998 Oct;5(2):65-9. [11541904 ]
  4. Askim M: [Vitamin K in the Norwegian diet and osteoporosis]. Tidsskr Nor Laegeforen. 2001 Sep 20;121(22):2614-6. [11668761 ]
  5. Kawana K, Takahashi M, Hoshino H, Kushida K: Circulating levels of vitamin K1, menaquinone-4, and menaquinone-7 in healthy elderly Japanese women and patients with vertebral fractures and patients with hip fractures. Endocr Res. 2001 Aug;27(3):337-43. [11678581 ]
General Function:
Gamma-glutamyl carboxylase activity
Specific Function:
Mediates the vitamin K-dependent carboxylation of glutamate residues to calcium-binding gamma-carboxyglutamate (Gla) residues with the concomitant conversion of the reduced hydroquinone form of vitamin K to vitamin K epoxide.
Gene Name:
GGCX
Uniprot ID:
P38435
Molecular Weight:
87560.065 Da
References
  1. Morris DP, Soute BA, Vermeer C, Stafford DW: Characterization of the purified vitamin K-dependent gamma-glutamyl carboxylase. J Biol Chem. 1993 Apr 25;268(12):8735-42. [8473318 ]
  2. Tuan RS: Vitamin K-dependent gamma-glutamyl carboxylase activity in the chick embryonic chorioallantoic membrane. J Biol Chem. 1979 Feb 25;254(4):1356-64. [105006 ]
  3. Reedstrom CK, Suttie JW: Comparative distribution, metabolism, and utilization of phylloquinone and menaquinone-9 in rat liver. Proc Soc Exp Biol Med. 1995 Sep;209(4):403-9. [7638250 ]
  4. Tasatargil A, Cadir B, Dalaklioglu S, Yurdakonar E, Caglar S, Turkay C: Effects of vitamin K1 supplementation on vascular responsiveness and oxidative stress in a rat femoral osteotomy model. Cell Biochem Funct. 2007 Sep-Oct;25(5):485-90. [16929463 ]
  5. Olson RE: The function and metabolism of vitamin K. Annu Rev Nutr. 1984;4:281-337. [6380538 ]