2,3-Epoxyphylloquinone (BioDeep_00000173527)

   

human metabolite blood metabolite


代谢物信息卡片


Naphth[2,3-b]oxirene-2,7-dione, 1a,7a-dihydro-1a-methyl-7a-(3,7,11,15-tetramethyl-2-hexadecenyl)-phylloquinone oxide

化学式: C31H46O3 (466.3447)
中文名称: 维生素K1 2,3-环氧
谱图信息: 最多检出来源 Salix miyabeana(blood) 4.82%

分子结构信息

SMILES: CC(C)CCCC(C)CCCC(C)CCCC(=CCC12C(=O)C3=CC=CC=C3C(=O)C1(O2)C)C
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

描述信息

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]

同义名列表

21 个代谢物同义名

Naphth[2,3-b]oxirene-2,7-dione, 1a,7a-dihydro-1a-methyl-7a-(3,7,11,15-tetramethyl-2-hexadecenyl)-phylloquinone oxide; 1a-methyl-7a-(3,7,11,15-tetramethylhexadec-2-en-1-yl)-1aH,2H,7H,7aH-naphtho[2,3-b]oxirene-2,7-dione; 1a,7a-Dihydro-1a-methyl-7a-(3,7,11,15-tetramethyl-2-hexadecenyl)-naphth[2,3-b]oxirene-2,7-dione; 1,4-Naphthoquinone, 2,3-epoxy-2,3-dihydro-2-methyl-3-phytyl-2,3-epoxyphylloquinone; 2,3-Epoxy-2,3-dihydro-2-methyl-3-phytyl-1,4-naphthoquinone; (2,3-Epoxyphytyl)menaquinone; Phylloquinone-2,3-epoxide; Phylloquinone 2,3-epoxide; Vitamin K1 2,3-epoxide; 2,3-epoxyphylloquinone; Phylloquinone, epoxide; Phylloquinone epoxide; Vitamin K 2,3-epoxide; Vitamin K1 2,3-Oxide; Vitamin K1, epoxide; Phylloquinone oxide; Vitamin K(1) oxide; Vitamin K1 epoxide; Vitamin K epoxide; Vitamin K1 oxide; Vitamin K1 epoxide



数据库引用编号

10 个数据库交叉引用编号

分类词条

相关代谢途径

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代谢反应

0 个相关的代谢反应过程信息。

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2 个相关的物种来源信息

在这里通过桑基图来展示出与当前的这个代谢物在我们的BioDeep知识库中具有相关联信息的其他代谢物。在这里进行关联的信息来源主要有：

  • PubMed: 来源于PubMed文献库中的文献信息，我们通过自然语言数据挖掘得到的在同一篇文献中被同时提及的相关代谢物列表，这个列表按照代谢物同时出现的文献数量降序排序，取前10个代谢物作为相关研究中关联性很高的代谢物集合展示在桑基图中。
  • NCBI Taxonomy: 通过文献数据挖掘，得到的代谢物物种来源信息关联。这个关联信息同样按照出现的次数降序排序，取前10个代谢物作为高关联度的代谢物集合展示在桑吉图上。
  • Chemical Taxonomy: 在物质分类上处于同一个分类集合中的其他代谢物
  • Chemical Reaction: 在化学反应过程中，存在为当前代谢物相关联的生化反应过程中的反应底物或者反应产物的关联代谢物信息。

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亚细胞结构定位 关联基因列表
Cytoplasm 8 ALB, BGLAP, CAT, CYP2C9, GAS6, HPGDS, NQO1, TXN
Peripheral membrane protein 1 HSD17B6
Endoplasmic reticulum membrane 6 CALU, CYP2C9, HSP90B1, PROS1, VKORC1, VKORC1L1
Nucleus 4 ALB, HSP90B1, NQO1, TXN
cytosol 7 ALB, CAT, EHHADH, HPGDS, HSP90B1, NQO1, TXN
dendrite 2 BGLAP, NQO1
centrosome 1 ALB
nucleoplasm 2 HPGDS, TXN
Cell membrane 1 AXL
Early endosome membrane 1 HSD17B6
Multi-pass membrane protein 2 VKORC1, VKORC1L1
Synapse 1 NQO1
cell surface 1 AXL
Golgi apparatus 2 ALB, CALU
Golgi membrane 1 PROS1
neuronal cell body 1 NQO1
smooth endoplasmic reticulum 1 HSP90B1
Cytoplasm, cytosol 1 NQO1
plasma membrane 6 AXL, CYP2C9, F2, F7, F9, PROS1
Membrane 5 AXL, CALU, CAT, HSP90B1, NQO1
extracellular exosome 10 ALB, AXL, CAT, F2, F9, GAS6, HSP90B1, MGP, PROS1, TXN
Lumenal side 1 HSD17B6
endoplasmic reticulum 7 ALB, CALU, HSD17B6, HSP90B1, PROS1, VKORC1, VKORC1L1
extracellular space 8 ALB, AXL, BGLAP, F2, F7, F9, GAS6, PROS1
perinuclear region of cytoplasm 1 HSP90B1
mitochondrion 1 CAT
protein-containing complex 3 ALB, CAT, HSP90B1
intracellular membrane-bounded organelle 5 AXL, CAT, CYP2C9, HPGDS, HSD17B6
Microsome membrane 2 CYP2C9, HSD17B6
Single-pass type I membrane protein 1 AXL
Secreted 9 ALB, BGLAP, CALU, F2, F7, F9, GAS6, PROS1, TXN
extracellular region 11 ALB, BGLAP, CALU, CAT, F2, F7, F9, GAS6, HSP90B1, PROS1, TXN
mitochondrial matrix 1 CAT
anchoring junction 1 ALB
actin cytoskeleton 1 AXL
perikaryon 1 BGLAP
midbody 1 HSP90B1
vesicle 2 BGLAP, F7
focal adhesion 2 CAT, HSP90B1
extracellular matrix 1 MGP
Peroxisome 2 CAT, EHHADH
Peroxisome matrix 1 CAT
peroxisomal matrix 2 CAT, EHHADH
peroxisomal membrane 1 CAT
collagen-containing extracellular matrix 5 F2, F7, F9, HSP90B1, MGP
receptor complex 1 AXL
ciliary basal body 1 ALB
centriole 1 ALB
spindle pole 1 ALB
blood microparticle 3 ALB, F2, PROS1
Melanosome 2 CALU, HSP90B1
sperm plasma membrane 1 HSP90B1
ficolin-1-rich granule lumen 1 CAT
secretory granule lumen 1 CAT
Golgi lumen 6 BGLAP, F2, F7, F9, GAS6, PROS1
endoplasmic reticulum lumen 8 ALB, BGLAP, CALU, F2, F7, F9, GAS6, HSP90B1
platelet alpha granule lumen 3 ALB, GAS6, PROS1
Sarcoplasmic reticulum lumen 2 CALU, HSP90B1
endocytic vesicle lumen 1 HSP90B1
catalase complex 1 CAT
endoplasmic reticulum chaperone complex 1 HSP90B1
serine-type peptidase complex 1 F7
ciliary transition fiber 1 ALB


文献列表

  • Kuan Hu, Yan Li, Ru Ding, Yu Zhai, Lin Chen, Wei Qian, Jin Yang. A simple, sensitive, and high-throughput LC-APCI-MS/MS method for simultaneous determination of vitamin K1, vitamin K1 2,3-epoxide in human plasma and its application to a clinical pharmacodynamic study of warfarin. Journal of pharmaceutical and biomedical analysis. 2018 Sep; 159(?):82-91. doi: 10.1016/j.jpba.2018.06.041. [PMID: 29980023]
  • Alessandra Gentili, Arturo Cafolla, Tecla Gasperi, Simona Bellante, Fulvia Caretti, Roberta Curini, Virginia Pérez Fernández. Rapid, high performance method for the determination of vitamin K(1), menaquinone-4 and vitamin K(1) 2,3-epoxide in human serum and plasma using liquid chromatography-hybrid quadrupole linear ion trap mass spectrometry. Journal of chromatography. A. 2014 Apr; 1338(?):102-10. doi: 10.1016/j.chroma.2014.02.065. [PMID: 24630057]
  • Simone Rost, Andreas Fregin, Mirja Hünerberg, Carville G Bevans, Clemens R Müller, Johannes Oldenburg. Site-directed mutagenesis of coumarin-type anticoagulant-sensitive VKORC1: evidence that highly conserved amino acids define structural requirements for enzymatic activity and inhibition by warfarin. Thrombosis and haemostasis. 2005 Oct; 94(4):780-6. doi: 10.1160/th05-02-0082. [PMID: 16270630]
  • Andreas Fregin, Simone Rost, Werner Wolz, Alice Krebsova, Clemens R Muller, Johannes Oldenburg. Homozygosity mapping of a second gene locus for hereditary combined deficiency of vitamin K-dependent clotting factors to the centromeric region of chromosome 16. Blood. 2002 Nov; 100(9):3229-32. doi: 10.1182/blood-2002-03-0698. [PMID: 12384421]
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  • F Kamali, C Edwards, T J Butler, H A Wynne. The influence of (R)- and (S)-warfarin, vitamin K and vitamin K epoxide upon warfarin anticoagulation. Thrombosis and haemostasis. 2000 Jul; 84(1):39-42. doi: . [PMID: 10928467]
  • M E Camilo, A Jatoi, M O'Brien, K Davidson, L Sokoll, J A Sadowski, J B Mason. Bioavailability of phylloquinone from an intravenous lipid emulsion. The American journal of clinical nutrition. 1998 Apr; 67(4):716-21. doi: 10.1093/ajcn/67.4.716. [PMID: 9537619]
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  • E G Bovill, R F Soll, M Lynch, F Bhushan, M Landesman, M Freije, W Church, T McAuliffe, K Davidson, J Sadowski. Vitamin K1 metabolism and the production of des-carboxy prothrombin and protein C in the term and premature neonate. Blood. 1993 Jan; 81(1):77-83. doi: . [PMID: 8417804]
  • M Guillaumont, H Weiser, L Sann, B Vignal, M Leclercq, A Frederich. Hepatic concentration of vitamin K active compounds after application of phylloquinone to chickens on a vitamin K deficient or adequate diet. International journal for vitamin and nutrition research. Internationale Zeitschrift fur Vitamin- und Ernahrungsforschung. Journal international de vitaminologie et de nutrition. 1992; 62(1):15-20. doi: NULL. [PMID: 1587702]
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  • B Brenner, S Tavori, A Zivelin, C B Keller, J W Suttie, I Tatarsky, U Seligsohn. Hereditary deficiency of all vitamin K-dependent procoagulants and anticoagulants. British journal of haematology. 1990 Aug; 75(4):537-42. doi: 10.1111/j.1365-2141.1990.tb07795.x. [PMID: 2145029]
  • D Trenk, F Wagner, H Bechtold, B Nies, E Jähnchen. Lack of effect of cefixime on the metabolism of vitamin K1. Journal of clinical pharmacology. 1990 Aug; 30(8):737-42. doi: 10.1002/j.1552-4604.1990.tb03636.x. [PMID: 2401753]
  • Y Yamanaka, M Yamano, K Yasunaga, T Shike, K Uchida. Effect of warfarin on plasma and liver vitamin K levels and vitamin K epoxide reductase activity in relation to plasma clotting factor levels in rats. Thrombosis research. 1990 Jan; 57(2):205-14. doi: 10.1016/0049-3848(90)90320-c. [PMID: 2315885]
  • G Soulban, G Labrecque, P M Bélanger. Temporal variation in the effects of warfarin on the vitamin K cycle. Chronobiology international. 1990; 7(5-6):403-11. doi: 10.3109/07420529009059151. [PMID: 2097073]
  • M E Mount, P H Kass. Diagnostic importance of vitamin K1 and its epoxide measured in serum of dogs exposed to an anticoagulant rodenticide. American journal of veterinary research. 1989 Oct; 50(10):1704-9. doi: . [PMID: 2802299]
  • F Moussa, L Dufour, J R Didry, P Aymard. Determination of trans-phylloquinone in children's serum. Clinical chemistry. 1989 May; 35(5):874-8. doi: 10.1093/clinchem/35.5.874. [PMID: 2720986]
  • M J Winn, P M White, A K Scott, S K Pratt, B K Park. The bioavailability of a mixed micellar preparation of vitamin K1, and its procoagulant effect in anticoagulated rabbits. The Journal of pharmacy and pharmacology. 1989 Apr; 41(4):257-60. doi: 10.1111/j.2042-7158.1989.tb06446.x. [PMID: 2568466]
  • K Hirauchi, T Sakano, T Nagaoka, A Morimoto. Simultaneous determination of vitamin K1, vitamin K1 2,3-epoxide and menaquinone-4 in human plasma by high-performance liquid chromatography with fluorimetric detection. Journal of chromatography. 1988 Aug; 430(1):21-9. doi: 10.1016/s0378-4347(00)83130-8. [PMID: 2851012]
  • S E Hazelett, P C Preusch. Tissue distribution and warfarin sensitivity of vitamin K epoxide reductase. Biochemical pharmacology. 1988 Mar; 37(5):929-34. doi: 10.1016/0006-2952(88)90183-9. [PMID: 3345202]
  • M J Shearer, H Bechtold, K Andrassy, J Koderisch, P T McCarthy, D Trenk, E Jähnchen, E Ritz. Mechanism of cephalosporin-induced hypoprothrombinemia: relation to cephalosporin side chain, vitamin K metabolism, and vitamin K status. Journal of clinical pharmacology. 1988 Jan; 28(1):88-95. doi: 10.1002/j.1552-4604.1988.tb03106.x. [PMID: 3350995]
  • R M Pauli, J B Lian, D F Mosher, J W Suttie. Association of congenital deficiency of multiple vitamin K-dependent coagulation factors and the phenotype of the warfarin embryopathy: clues to the mechanism of teratogenicity of coumarin derivatives. American journal of human genetics. 1987 Oct; 41(4):566-83. doi: . [PMID: 3499071]
  • I A Choonara, B P Haynes, S Cholerton, A M Breckenridge, B K Park. Enantiomers of warfarin and vitamin K1 metabolism. British journal of clinical pharmacology. 1986 Dec; 22(6):729-32. doi: 10.1111/j.1365-2125.1986.tb02966.x. [PMID: 3567019]
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  • H Bechtold, D Trenk, T Meinertz, M Rowland, E Jähnchen. Cyclic interconversion of vitamin K1 and vitamin K1 2,3-epoxide in man. British journal of clinical pharmacology. 1983 Dec; 16(6):683-9. doi: 10.1111/j.1365-2125.1983.tb02241.x. [PMID: 6661354]
  • A C Wilson, B K Park. Quantitative analysis of pharmacological levels of vitamin K1 and vitamin K1 2,3-epoxide in rabbit plasma by high-performance liquid chromatography. Journal of chromatography. 1983 Oct; 277(?):292-9. doi: 10.1016/s0378-4347(00)84847-1. [PMID: 6643613]
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  • . . . . doi: . [PMID: 24489112]