<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <id type="integer">3001</id>
  <title>T3D2959</title>
  <common-name>Phytonadione</common-name>
  <description>Phylloquinone 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.</description>
  <cas>84-80-0</cas>
  <pubchem-id>5284607</pubchem-id>
  <chemical-formula>C31H46O2</chemical-formula>
  <weight>450.349780</weight>
  <appearance nil="true"/>
  <melting-point>-20°C</melting-point>
  <boiling-point>142.5°C at 1.00E-03 mm Hg</boiling-point>
  <density nil="true"/>
  <solubility>Insoluble in water</solubility>
  <specific-gravity nil="true"/>
  <flash-point nil="true"/>
  <vapour-pressure nil="true"/>
  <route-of-exposure>Subcutaneous, 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.</route-of-exposure>
  <target nil="true"/>
  <mechanism-of-toxicity>Vitamin 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.</mechanism-of-toxicity>
  <metabolism>Route of Elimination: Almost no free unmetabolized vitamin K appears in bile or urine.</metabolism>
  <toxicity>LD50: 41.5 mL/kg at 0.2% (Intravenous, Mouse) (A308)LD50: 52 mL/kg at 1% (Intravenous, Mouse) (A308)</toxicity>
  <lethaldose nil="true"/>
  <carcinogenicity>3, not classifiable as to its carcinogenicity to humans. (L135)</carcinogenicity>
  <use-source>For the treatment of haemorrhagic conditions in infants, antidote for coumarin anticoagulants in hypoprothrombinaemia.</use-source>
  <min-risk-level nil="true"/>
  <health-effects nil="true"/>
  <symptoms></symptoms>
  <treatment nil="true"/>
  <created-at type="dateTime">2009-07-21T20:28:11Z</created-at>
  <updated-at type="dateTime">2014-12-24T20:25:54Z</updated-at>
  <interacting-proteins nil="true"/>
  <wikipedia>Phytonadione</wikipedia>
  <uniprot-id></uniprot-id>
  <kegg-compound-id>C02059</kegg-compound-id>
  <omim-id>118650
122700
176860
176880
176930
188055
215100
227600
277450
306900
607473</omim-id>
  <chebi-id>18067</chebi-id>
  <biocyc-id>3-HYDROXY-2-METHYL-3-PHYTYL-23-DIHYDRONA</biocyc-id>
  <ctd-id nil="true"/>
  <stitch-id>Phytonadione</stitch-id>
  <drugbank-id>DB01022</drugbank-id>
  <pdb-id>PQN</pdb-id>
  <actor-id nil="true"/>
  <organism nil="true"/>
  <export type="boolean">true</export>
  <metabolizing-proteins nil="true"/>
  <transporting-proteins nil="true"/>
  <moldb-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</moldb-smiles>
  <moldb-formula>C31H46O2</moldb-formula>
  <moldb-inchi>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+/t23-,24-/m1/s1</moldb-inchi>
  <moldb-inchikey>InChIKey=MBWXNTAXLNYFJB-NKFFZRIASA-N</moldb-inchikey>
  <moldb-average-mass type="decimal">450.6957</moldb-average-mass>
  <moldb-mono-mass type="decimal">450.349780716</moldb-mono-mass>
  <origin>Exogenous</origin>
  <state>Liquid</state>
  <logp>9.3</logp>
  <hmdb-id>HMDB15157</hmdb-id>
  <chembl-id>CHEMBL1550</chembl-id>
  <chemspider-id>4447652</chemspider-id>
  <structure-image-file-name nil="true"/>
  <structure-image-content-type nil="true"/>
  <structure-image-file-size type="integer" nil="true"/>
  <structure-image-updated-at type="dateTime" nil="true"/>
  <biodb-id nil="true"/>
  <synthesis-reference>&lt;p&gt;Manfred Dorner, &amp;#8220;Method of making vitamin K1.&amp;#8221; U.S. Patent US5744624, issued June, 1964.&lt;/p&gt;</synthesis-reference>
  <structure-image-caption nil="true"/>
</compound>
