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phytomenadione; vitamin k 1; vitamin k1 epoxide-1,4-diol


Name(s) phytomenadione; vitamin k 1; vitamin k1 epoxide-1,4-diol
Scientific name(s) phylloquinone; vitamin k1; phytonadione; 84-80-0; phytylmenadione; 3-phytylmenadione; aquamephyton; phytomenadione
Formula C31H46O2
Molecular mass 450.7
IUPAC name 2-methyl-3-[(E,7R,11R)-3,7,11,15-tetramethylhexadec-2-enyl]naphthalene-1,4-dione
INCHI InChI=1S/C31H50O3/c1-22(2)12-9-13-23(3)14-10-15-24(4)16-11-17-25(5)20-21-31-29(33)27-19-8-7-18-26(27)28(32)30(31,6)34-31/h7-8,18-20,22-24,28-29,32-33H,9-17,21H2,1-6H3
SMILE CC(C)CCCC(C)CCCC(C)CCCC(C)=CCC12OC1(C)C(O)C1=CC=CC=C1C2O
CAS ID 79083-00-4; 81382-12-9
PubChem ID 5284607
DrugBank ID DB01022
CHEBI ID Not available
Description Vitamin K is a family of fat-soluble compounds with a common chemical structure, 2, methyl-1,4-napthoquinone. Phylloquinone is present in food of plant origin, such as green, leafy vegetables and certain plant oils, and is the predominant form in the diet. Bacterial and other forms of vitamin K, referred to as the menaquinones, differ in structure from phylloquinone in their 3-substituted lipophilic side chain. Menaquinone-4 (MK-4), which is alkylated from menadione, is present in animal feeds or is the product of tissue-specific conversion directly from dietary phylloquinone. Vitamin K is a cofactor specific to the formation of gamma-carboxyglutamyl (Gla) residues in certain proteins, including prothrombin necessary for normal hemostatic function. The naturally occurring forms of vitamin K are quinones (i.e. phylloquinone and menaquinones) so vitamin K is reduced to the vitamin K hydroquinone prior to catalyzing the gamma-carboxylation reaction. The active site for the carboxylation reaction is on the napthoquinone ring, which is identical for all forms of vitamin K, including phylloquinone and MK-4. (PMID 16857056) [HMDB]