Demethylphylloquinone (BioDeep_00000009440)

 

Secondary id: BioDeep_00001872486

human metabolite Endogenous


代谢物信息卡片


2-[(2E,7R,11R)-3,7,11,15-tetramethylhexadec-2-en-1-yl]-1,4-dihydronaphthalene-1,4-dione

化学式: C30H44O2 (436.3341124)
中文名称:
谱图信息: 最多检出来源 Viridiplantae(plant) 0.29%

分子结构信息

SMILES: CC(=CCC1=CC(=O)c2ccccc2C1=O)CCCC(C)CCCC(C)CCCC(C)C
InChI: InChI=1S/C30H44O2/c1-22(2)11-8-12-23(3)13-9-14-24(4)15-10-16-25(5)19-20-26-21-29(31)27-17-6-7-18-28(27)30(26)32/h6-7,17-19,21-24H,8-16,20H2,1-5H3/b25-19+

描述信息

Demethylphylloquinone is a form of vitamin K that occurs in nature as part of a series of compounds with a common 2-methyl-1,4 naphthoquinone nucleus and differing isoprenoid side chains at the 3 position. Vitamin K forms comprise a single major plant form, phylloquinone with a phytyl side chain and a family of bacterially synthesized menaquinones (MKs) with multiprenyl side chains. Bacterially produced menaquinones are biologically active forms of vitamin K that are present in high concentrations in the human lower bowel. Both phylloquinone and menaquinones are bioactive in hepatic gamma-carboxylation but long-chain MKs are less well absorbed. Liver stores of vitamin K are relatively small. The hepatic reserves of phylloquinone (approximately 10\\% of the total) are labile and turn over at a faster rate than menaquinones. Vitamin K is recognised as a factor required for normal blood coagulation, and in relation to its role in bone metabolism. Vitamin K is a substrate for a liver microsomal enzyme that catalyzes the conversion of specific glutamyl residues to gamma-carboxyglutamyl residues in a limited number of proteins. These include the vitamin K-dependent clotting factors: prothrombin (factor II), factor VII, factor IX, and factor X. In the absence of vitamin K, nonfunctional clotting factors are synthesized and hemorrhage can result. Vitamin K is a coenzyme for glutamate carboxylase, which mediates the conversion of glutamate to gamma-carboxyglutamate (Gla). There are at least three Gla proteins associated with bone tissue, of which osteocalcin is the most abundant and best known. Trabecular and cortical bone appear to contain substantial concentrations of both phylloquinone and menaquinones. (PMID: 8642453, 8527227, 15018483, 1573141) [HMDB]
Demethylphylloquinone is a form of vitamin K that occurs in nature as part of a series of compounds with a common 2-methyl-1,4 naphthoquinone nucleus and differing isoprenoid side chains at the 3 position. Vitamin K forms comprise a single major plant form, phylloquinone with a phytyl side chain and a family of bacterially synthesized menaquinones (MKs) with multiprenyl side chains. Bacterially produced menaquinones are biologically active forms of vitamin K that are present in high concentrations in the human lower bowel. Both phylloquinone and menaquinones are bioactive in hepatic gamma-carboxylation but long-chain MKs are less well absorbed. Liver stores of vitamin K are relatively small. The hepatic reserves of phylloquinone (approximately 10\\% of the total) are labile and turn over at a faster rate than menaquinones. Vitamin K is recognised as a factor required for normal blood coagulation, and in relation to its role in bone metabolism. Vitamin K is a substrate for a liver microsomal enzyme that catalyzes the conversion of specific glutamyl residues to gamma-carboxyglutamyl residues in a limited number of proteins. These include the vitamin K-dependent clotting factors: prothrombin (factor II), factor VII, factor IX, and factor X. In the absence of vitamin K, nonfunctional clotting factors are synthesized and hemorrhage can result. Vitamin K is a coenzyme for glutamate carboxylase, which mediates the conversion of glutamate to gamma-carboxyglutamate (Gla). There are at least three Gla proteins associated with bone tissue, of which osteocalcin is the most abundant and best known. Trabecular and cortical bone appear to contain substantial concentrations of both phylloquinone and menaquinones. (PMID: 8642453, 8527227, 15018483, 1573141).

同义名列表

9 个代谢物同义名

2-[(2E,7R,11R)-3,7,11,15-tetramethylhexadec-2-en-1-yl]-1,4-dihydronaphthalene-1,4-dione; 2-[(2E,7R,11R)-3,7,11,15-Tetramethyl-2-hexadecenyl]-1,4-naphthalenedione; 2-Phytyl-1,4-naphthoquinone; Nor-alpha-phylloquinone; Demethylphylloquinone; Nor-α-phylloquinone; SCHEMBL1533798; Norvitamin K; PHNQ CPD



数据库引用编号

16 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(0)

BioCyc(2)

PlantCyc(2)

代谢反应

249 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(3)

WikiPathways(0)

Plant Reactome(3)

INOH(0)

PlantCyc(243)

COVID-19 Disease Map(0)

PathBank(0)

PharmGKB(0)

1 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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文献列表

  • Beatrycze Nowicka, Jerzy Kruk. Occurrence, biosynthesis and function of isoprenoid quinones. Biochimica et biophysica acta. 2010 Sep; 1797(9):1587-605. doi: 10.1016/j.bbabio.2010.06.007. [PMID: 20599680]
  • Antje Lohmann, Mark Aurel Schöttler, Claire Bréhélin, Felix Kessler, Ralph Bock, Edgar B Cahoon, Peter Dörmann. Deficiency in phylloquinone (vitamin K1) methylation affects prenyl quinone distribution, photosystem I abundance, and anthocyanin accumulation in the Arabidopsis AtmenG mutant. The Journal of biological chemistry. 2006 Dec; 281(52):40461-72. doi: 10.1074/jbc.m609412200. [PMID: 17082184]