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Record Information
Version3.6
Creation Date2006-08-12 23:40:55 UTC
Update Date2016-02-11 01:06:22 UTC
HMDB IDHMDB03555
Secondary Accession Numbers
  • HMDB03596
Metabolite Identification
Common NameVitamin K1
DescriptionVitamin K1 or Phylloquinone is a polycyclic aromatic ketone, based on 1,4-naphthoquinone, with 2-methyl and 3-phytyl substituents. Vitamin K is a family of phylloquinones that contains a ring of 2-methyl-1,4-naphthoquinone and an isoprenoid side chain. Several forms of vitamin K have been identified: vitamin K 1 (vitamin K 1) derived from plants, vitamin K 2 (menaquinone) from bacteria, and synthetic naphthoquinone provitamins, vitamin K 3 (menadione). Vitamin K1 has only one double bond on the proximal isoprene unit. Vitamin K1 possesses the same type and degree of activity as does naturally-occurring vitamin K, which is necessary for the production via the liver of active prothrombin (factor II), proconvertin (factor VII), plasma thromboplastin component (factor IX), and Stuart factor (factor X). Rich sources of vitamin K 1 include green plants, algae, and photosynthetic bacteria. Vitamin K1 has antihemorrhagic and prothrombogenic activity. Vitamin K1 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.
Structure
Thumb
Synonyms
ValueSource
Vitamin K1Kegg
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
Combinal K1HMDB
FitomenadionaHMDB
FitomenadioneHMDB
K-JectHMDB
Kativ NHMDB
KephtonHMDB
KinadionHMDB
KonakionHMDB
mono-KayHMDB
MonodionHMDB
PhyllochinonHMDB
PhyllochinonumHMDB
PhylloquinoneHMDB
Phythyl-menadionHMDB
PhytomenadionumHMDB
PhytonadionumHMDB
PhytylmenadioneHMDB
Synthex PHMDB
trans-PhylloquinoneHMDB
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 KeyInChIKey=MBWXNTAXLNYFJB-LKUDQCMESA-N
Chemical Taxonomy
DescriptionThis compound 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
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aromatic homopolycyclic compound
Molecular FrameworkAromatic homopolycyclic compounds
External Descriptors
Ontology
StatusDetected and Quantified
Origin
  • Drug
  • Food
  • Plant
Biofunction
  • Cell signaling
  • Essential vitamins
  • Fuel and energy storage
  • Fuel or energy source
  • Membrane integrity/stability
Application
  • Nutrients
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Cytoplasm
  • Extracellular
  • Membrane (predicted from logP)
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility5.92e-05 mg/mLALOGPS
logP8.48ALOGPS
logP9.7ChemAxon
logS-6.9ALOGPS
pKa (Strongest Basic)-7.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area34.14 Å2ChemAxon
Rotatable Bond Count14ChemAxon
Refractivity142.96 m3·mol-1ChemAxon
Polarizability56.8 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
MSMass Spectrum (Electron Ionization)splash10-0ug0-9860500000-a5cd1646f1fc838bc7d7View in MoNA
1D NMR1H NMR SpectrumNot Available
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane (predicted from logP)
Biofluid Locations
  • Blood
Tissue Location
  • Liver
Pathways
NameSMPDB LinkKEGG Link
Vitamin K MetabolismSMP00464Not Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.00049 (0.00009-0.0022) uMAdolescent (13-18 years old)BothNormal details
BloodDetected and Quantified0.0011 +/- 0.0042 uMAdult (>18 years old)FemaleNormal details
BloodDetected and Quantified0.0058 (0.0020-0.017) uMAdult (>18 years old)BothNormal
    • Geigy Scientific ...
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB01022
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB012357
KNApSAcK IDC00002868
Chemspider ID4444124
KEGG Compound IDC02059
BioCyc ID3-HYDROXY-2-METHYL-3-PHYTYL-23-DIHYDRONA
BiGG ID39000
Wikipedia LinkVitamin K
NuGOwiki LinkHMDB03555
Metagene LinkHMDB03555
METLIN ID6952
PubChem Compound5280483
PDB IDNot Available
ChEBI ID583972
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. 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. [2851012 ]
  2. 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. [5511811 ]
  3. 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. [10701947 ]
  4. 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. [10893417 ]
  5. de Moerloose P, Boehlen F: [Haemostasis. A search for an ideal antithrombotics agent] Rev Med Suisse. 2005 Jan 5;1(1):35-8. [15773196 ]
  6. 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. [1009028 ]

Enzymes

General function:
Involved in electron carrier activity
Specific function:
The enzyme apparently serves as a quinone reductase in connection with conjugation reactions of hydroquinons involved in detoxification pathways as well as in biosynthetic processes such as the vitamin K-dependent gamma-carboxylation of glutamate residues in prothrombin synthesis.
Gene Name:
NQO1
Uniprot ID:
P15559
Molecular weight:
30867.405
Reactions
Vitamin K1 + NADH + Hydrogen Ion → Phylloquinol + NADdetails
General function:
Involved in 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
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 ]
  6. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [11752352 ]
General function:
Involved in regulation of bone mineralization
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:
10962.4
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:
Involved in vitamin-K-epoxide reductase (warfarin-sensi
Specific function:
Involved in vitamin K metabolism. Catalytic subunit of the vitamin K epoxide reductase (VKOR) complex which reduces inactive vitamin K 2,3-epoxide to active vitamin K.
Gene Name:
VKORC1
Uniprot ID:
Q9BQB6
Molecular weight:
18234.3
Reactions
Vitamin K1 + Oxidized dithiothreitol + Water → Vitamin K1 2,3-epoxide + 1,4-Dithiothreitoldetails