1.0 2011-09-21 00:24:29 UTC 2015-07-21 06:57:30 UTC FDB023087 Vitamin K1 2,3-epoxide Vitamin K1 2,3-epoxide is a vitamin K derivative. Vitamin K 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 to Gamma-cabroxygluatmate (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 to 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 to 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 coumarin-like activity of drugs. (PMID 2401753) [HMDB] (2,3-Epoxyphytyl)menaquinone 1,4-Naphthoquinone, 2,3-epoxy-2,3-dihydro-2-methyl-3-phytyl-2,3-Epoxyphylloquinone 1a,7a-dihydro-1a-Methyl-7a-(3,7,11,15-tetramethyl-2-hexadecenyl)-naphth[2,3-b]oxirene-2,7-dione 2,3-epoxy-2,3-dihydro-2-methyl-3-phytyl-1,4-naphthoquinone 2,3-Epoxyphylloquinone Naphth[2,3-b]oxirene-2,7-dione, 1a,7a-dihydro-1a-methyl-7a-(3,7,11,15-tetramethyl-2-hexadecenyl)-Phylloquinone oxide Phylloquinone 2,3-epoxide Phylloquinone epoxide Phylloquinone oxide Phylloquinone-2,3-epoxide Vitamin K 2,3-epoxide Vitamin K epoxide Vitamin K1 oxide C31H46O3 466.6951 466.344695338 1a-methyl-7a-(3,7,11,15-tetramethylhexadec-2-en-1-yl)-1aH,2H,7H,7aH-naphtho[2,3-b]oxirene-2,7-dione vitamin k epoxide 25486-55-9 CC(C)CCCC(C)CCCC(C)CCCC(C)=CCC12OC1(C)C(=O)C1=CC=CC=C1C2=O InChI=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 KUTXFBIHPWIDJQ-UHFFFAOYSA-N 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. Vitamin K compounds Organic compounds Lipids and lipid-like molecules Prenol lipids Quinone and hydroquinone lipids Aromatic heteropolycyclic compounds Aryl alkyl ketones Dialkyl ethers Diterpenoids Epoxides Hydrocarbon derivatives Naphthoquinones Organic oxides Oxacyclic compounds Quinones Tetralins Aromatic heteropolycyclic compound Aryl alkyl ketone Aryl ketone Benzenoid Dialkyl ether Diterpenoid Ether Hydrocarbon derivative Ketone Naphthalene Naphthoquinone Organic oxide Organic oxygen compound Organoheterocyclic compound Organooxygen compound Oxacycle Oxirane Quinone Tetralin a small molecule epoxide phytylnaphthoquinone Solid logp 8.28 ALOGPS logs -7.32 ALOGPS solubility 2.24e-05 g/l ALOGPS logp 9.22 ChemAxon pka_strongest_basic -4.4 ChemAxon iupac 1a-methyl-7a-(3,7,11,15-tetramethylhexadec-2-en-1-yl)-1aH,2H,7H,7aH-naphtho[2,3-b]oxirene-2,7-dione ChemAxon average_mass 466.6951 ChemAxon mono_mass 466.344695338 ChemAxon smiles CC(C)CCCC(C)CCCC(C)CCCC(C)=CCC12OC1(C)C(=O)C1=CC=CC=C1C2=O ChemAxon formula C31H46O3 ChemAxon inchi InChI=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 ChemAxon inchikey KUTXFBIHPWIDJQ-UHFFFAOYSA-N ChemAxon polar_surface_area 46.67 ChemAxon refractivity 141.69 ChemAxon polarizability 57.54 ChemAxon rotatable_bond_count 14 ChemAxon acceptor_count 3 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Vitamin K Metabolism SMP00464 Specdb::CMs 17608 Specdb::CMs 123986 Specdb::MsMs 304975 Specdb::MsMs 304976 Specdb::MsMs 304977 Specdb::MsMs 348307 Specdb::MsMs 348308 Specdb::MsMs 348309 Specdb::MsMs 3400876 Specdb::MsMs 3400877 Specdb::MsMs 3400878 Specdb::MsMs 3400879 Specdb::MsMs 3400880 Specdb::MsMs 3400881 HMDB02972 28371 #<Reference:0x000055ce32c19138> #<Reference:0x000055ce32c18f80> #<Reference:0x000055ce32c18da0> #<Reference:0x000055ce32c18be8> #<Reference:0x000055ce32c18a30> Anatidae Type 1 specific Anatidae 8830 Beefalo Type 1 specific Bos taurus X Bison bison 297284 Bison Type 1 specific Bison bison 9901 Buffalo Type 1 specific Bubalus bubalis 89462 Cattle (Beef, Veal) Type 1 specific Bos taurus 9913 Chicken Type 1 specific Gallus gallus 9031 Columbidae (Dove, Pigeon) Type 1 specific Columbidae 8930 Deer Type 1 specific Cervidae 9850 Domestic goat Type 1 specific Capra aegagrus hircus 9925 Domestic pig Type 1 specific Sus scrofa domestica 9825 Elk Type 1 specific Cervus canadensis 1574408 Emu Type 1 specific Dromaius novaehollandiae 8790 European rabbit Type 1 specific Oryctolagus 9984 Greylag goose Type 1 specific Anser anser 8843 Guinea hen Type 1 specific Numida meleagris 8996 Horse Type 1 specific Equus caballus 9796 Mallard duck Type 1 specific Anas platyrhynchos 8839 Mountain hare Type 1 specific Lepus timidus 62621 Mule deer Type 1 specific Odocoileus 9871 Ostrich Type 1 specific Struthio camelus 8801 Pheasant Type 1 specific Phasianus colchicus 9054 Quail Type 1 specific Phasianidae 9005 Rabbit Type 1 specific Leporidae 9979 Rock ptarmigan Type 1 specific Lagopus muta 64668 Sheep (Mutton, Lamb) Type 1 specific Ovis aries 9940 Squab Type 1 specific Columba 8931 Turkey Type 1 specific Meleagris gallopavo 9103 Velvet duck Type 1 specific Melanitta fusca 371864 Wild boar Type 1 specific Sus scrofa 9823 Vitamin K epoxide reductase complex subunit 1 Q9BQB6 VKORC1