Showing Metabocard for 2,3-epoxyphylloquinone (BASm0000424)

Common Name2,3-epoxyphylloquinone
DescriptionVitamin K1 2,3-epoxide (CAS: 25486-55-9) is a vitamin K derivative. Vitamin K is needed for the posttranslational modification of certain proteins, mostly required for blood coagulation. Within the cell, vitamin K undergoes electron reduction to a reduced form of vitamin K (called vitamin K hydroquinone) by the enzyme vitamin K epoxide reductase (or VKOR). Another enzyme then oxidizes vitamin K hydroquinone to allow carboxylation of glutamate into gamma-carboxyglutamate (Gla). This enzyme is called the gamma-glutamyl carboxylase or the vitamin K-dependent carboxylase. The carboxylation reaction will only proceed if the carboxylase enzyme is able to oxidize vitamin K hydroquinone into vitamin K epoxide at the same time; the carboxylation and epoxidation reactions are said to be coupled reactions. Vitamin K epoxide is then re-converted into vitamin K by the vitamin K epoxide reductase. These two enzymes comprise the so-called vitamin K cycle. One of the reasons why vitamin K is rarely deficient in a human diet is because vitamin K is continually recycled in our cells. Vitamin K 2,3-epoxide is the substrate for vitamin K 2,3-epoxide reductase (VKOR) complex. Significantly increased level of serum vitamin K epoxide has been found in patients with familial multiple coagulation factor deficiency (PMID: 12384421 ). Accumulation of vitamin K1-2,3-epoxide in plasma is also a sensitive marker of the coumarin-like activity of drugs (PMID: 2401753 ).
Structure
Molecular FormulaC31H46O3
Average Mass466.70600
Monoisotopic Mass466.34470
IUPAC Name1a-methyl-7a-(3,7,11,15-tetramethylhexadec-2-en-1-yl)-1aH,2H,7H,7aH-naphtho[2,3-b]oxirene-2,7-dione
Traditional NameVitamin k epoxide
CAS Registry Number85955-78-8
SMILESC/C(=C\CC12OC1(C)C(=O)c1ccccc1C2=O)CCC[C@H](C)CCC[C@H](C)CCCC(C)C
InChI IdentifierInChI=1S/C31H46O3/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/h7-8,18-20,22-24H,9-17,21H2,1-6H3/b25-20+/t23-,24-,30-,31+/m1/s1
InChI KeyKUTXFBIHPWIDJQ-BTPXSFBUSA-N
CHEBI IDCHEBI:15759
HMDB IDHMDB0002972
Pathways
NameSMPDB/PathBank
Warfarin Action Pathway
Acenocoumarol Action Pathway
Dicumarol Action Pathway
Phenprocoumon Action Pathway
Enoxaparin Action Pathway
Fondaparinux Action Pathway
Heparin Action Pathway
Ardeparin Action Pathway
Argatroban Action Pathway
Bivalirudin Action Pathway
Lepirudin Action Pathway
Ximelagatran Action Pathway
Alteplase Action Pathway
Anistreplase Action Pathway
Streptokinase Action Pathway
Tenecteplase Action Pathway
Urokinase Action Pathway
Reteplase Action Pathway
Aminocaproic Acid Action Pathway
Tranexamic Acid Action Pathway
Aprotinin Action Pathway
Vitamin K Metabolism
Coagulation
Phenindione Action Pathway
Dicoumarol Action Pathway
StateSolid
Water Solubility2.24e-05 g/l
logP8.28
logS-7.32
pKa (Strongest Acidic)Not Available
pKa (Strongest Basic)-4.37
Hydrogen Acceptor Count3
Hydrogen Donor Count0
Polar Surface Area46.67 Ų
Rotatable Bond Count14
Physiological Charge0
Formal Charge0
Refractivity141.69 m³·mol⁻¹
Polarizability57.54

We require the use of cookies for essential features like storing your previously submitted BASys2 queries. Rejecting the usage of cookies will result in certain features being disabled. By clicking ACCEPT or continuing to use the website you are agreeing to our use of cookies.

ACCEPT