Calcitroic acid (BioDeep_00000012153)

 

Secondary id: BioDeep_00000637649

human metabolite Endogenous blood metabolite Volatile Flavor Compounds


代谢物信息卡片


(3R)-3-[(1R,3AR,4E,7ar)- 4-[(2Z)-2-[(3R,5R)-3,5- dihydroxy-2-methylene-cyclohexylidene]ethylidene] -7a-methyl-2,3,3a,5,6,7-hexahydro-1H -inden-1-yl]butanoic acid

化学式: C23H34O4 (374.24569640000004)
中文名称:
谱图信息: 最多检出来源 Homo sapiens(blood) 0.14%

分子结构信息

SMILES: C=C1C(=CC=C2CCCC3(C)C2CCC3C(C)CC(=O)O)CC(O)CC1O
InChI: InChI=1S/C23H34O4/c1-14(11-22(26)27)19-8-9-20-16(5-4-10-23(19,20)3)6-7-17-12-18(24)13-21(25)15(17)2/h6-7,14,18-21,24-25H,2,4-5,8-13H2,1,3H3,(H,26,27)/t14-,18-,19-,20+,21+,23-/m1/s1

描述信息

Calcitroic acid (1 alpha-hydroxy-23 carboxy-24,25,26,27-tetranorvitamin D(3)) is a metabolite of 1 alpha, 25-dihydroxyvitamin D(3) (calcitriol). It is soluble in water, and is excreted in urine. This deactivation process involves a series of oxidation reactions at C24 and C23 leading to side-chain cleavage and, ultimately, formation of the calcitroic acid. This deactivation involves the loss of carbons 24, 25, 26, and 27 and the oxidation of carbon 23 to a carboxylic acid. Calcitroic acid is also a major terminal product for the deactivation of 1α,25-dihydroxyvitamin D2. Both the kidney and the intestine metabolize 1,25-dihydroxyvitamin D3 through the C-24 oxidation pathway according to the following steps: 1,25-dihydroxyvitamin D3----1,24,25-trihydroxyvitamin D3----1,25-dihydroxy-24-oxovitamin D3-----1,23,25-trihydroxy-24-oxovitamin D3 (PMID: 2719932). The C-24 oxidation pathway leading to the formation of calcitroic acid has been reported to be present in bone cells, but the C-23 oxidation pathway leading to the formation of 1 alpha, 25-(OH)2D3-26,23-lactone has not been described in bone cells, even though 1 alpha, 25-(OH)2D3-26,23-lactone is noted to have a significant effect on bone formation. (PMID: 7664636) [HMDB]
Calcitroic acid (1 alpha-hydroxy-23 carboxy-24,25,26,27-tetranorvitamin D(3)) is a metabolite of 1 alpha, 25-dihydroxyvitamin D(3) (calcitriol). It is soluble in water, and is excreted in urine. This deactivation process involves a series of oxidation reactions at C24 and C23 leading to side-chain cleavage and, ultimately, formation of the calcitroic acid. This deactivation involves the loss of carbons 24, 25, 26, and 27 and the oxidation of carbon 23 to a carboxylic acid. Calcitroic acid is also a major terminal product for the deactivation of 1α,25-dihydroxyvitamin D2. Both the kidney and the intestine metabolize 1,25-dihydroxyvitamin D3 through the C-24 oxidation pathway according to the following steps: 1,25-dihydroxyvitamin D3----1,24,25-trihydroxyvitamin D3----1,25-dihydroxy-24-oxovitamin D3-----1,23,25-trihydroxy-24-oxovitamin D3 (PMID: 2719932). The C-24 oxidation pathway leading to the formation of calcitroic acid has been reported to be present in bone cells, but the C-23 oxidation pathway leading to the formation of 1 alpha, 25-(OH)2D3-26,23-lactone has not been described in bone cells, even though 1 alpha, 25-(OH)2D3-26,23-lactone is noted to have a significant effect on bone formation. (PMID: 7664636).
D018977 - Micronutrients > D014815 - Vitamins > D004100 - Dihydroxycholecalciferols
D018977 - Micronutrients > D014815 - Vitamins > D006887 - Hydroxycholecalciferols

同义名列表

21 个代谢物同义名

(3R)-3-[(1R,3AR,4E,7ar)- 4-[(2Z)-2-[(3R,5R)-3,5- dihydroxy-2-methylene-cyclohexylidene]ethylidene] -7a-methyl-2,3,3a,5,6,7-hexahydro-1H -inden-1-yl]butanoic acid; (3R)-3-[(1R,3AS,4E,7ar)-4-[(2Z)-2-[(3R,5S)-3,5-dihydroxy-2 methylidenecyclohexylidene]ethylidene]-7a-methyl-2,3,3a,5,6,7-hexahydro-1H-inden-1-yl]butanoic acid; (3R)-3-[(1R,3AR,4E,7ar)- 4-[(2Z)-2-[(3R,5R)-3,5- dihydroxy-2-methylene-cyclohexylidene]ethylidene] -7a-methyl-2,3,3a,5,6,7-hexahydro-1H -inden-1-yl]butanoate; (3R)-3-[(1R,3AS,4E,7ar)-4-[(2Z)-2-[(3R,5S)-3,5-dihydroxy-2 methylidenecyclohexylidene]ethylidene]-7a-methyl-2,3,3a,5,6,7-hexahydro-1H-inden-1-yl]butanoate; (3R)-3-[(1R,3aS,4E,7aR)-4-{2-[(1E,3S,5R)-3,5-dihydroxy-2-methylidenecyclohexylidene]ethylidene}-7a-methyl-octahydro-1H-inden-1-yl]butanoic acid; (3R)-3-[(1R,3aS,4E,7aR)-4-{2-[(1E,3S,5R)-3,5-dihydroxy-2-methylidenecyclohexylidene]ethylidene}-7a-methyl-hexahydro-1H-inden-1-yl]butanoic acid; (3R)-3-[(1R,3AS,4E,7ar)-4-{2-[(1E,3S,5R)-3,5-dihydroxy-2-methylidenecyclohexylidene]ethylidene}-7a-methyl-octahydro-1H-inden-1-yl]butanoate; 1α-hydroxy-24,25,26,27-tetranorvitamin D3 23-carboxylic acid / calcitroic acid; (5Z,7E)-(1S,3R)-1,3-dihydroxy-24-nor- 9,10-seco-5,7,10(19)-cholatrien-23-oic acid; 1 alpha,3 beta-Dihydroxy-24-nor-9,10- seco-5,7,10(19)-cholatrien-23-Oic acid; 1alpha,3beta-Dihydroxy-24-nor-9,10-seco-5,7,10(19)-cholatrien-23-Oic acid; 1alpha,3beta-Dihydroxy-24-nor-9,10-seco-5,7,10(19)-cholatrien-23-Oate; 1 alpha-Hydroxy-23 carboxy-24,25,26,27-tetranorvitamin D(3); 1 alpha-Hydroxy-23-carboxytetranorvitamin D; 1alpha-Hydroxy-23-carboxytetranorvitamin D; 1a-Hydroxycalcioic acid; Calcitroic acid (D3); 1a-Hydroxycalcioate; Calcitroic acid; Calcitroate; Calcitroic acid



数据库引用编号

17 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(4)

BioCyc(0)

PlantCyc(0)

代谢反应

32 个相关的代谢反应过程信息。

Reactome(32)

BioCyc(0)

WikiPathways(0)

Plant Reactome(0)

INOH(0)

PlantCyc(0)

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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。

点击图上的相关代谢物的名称，可以跳转到相关代谢物的信息页面。



文献列表

  • Martin Kaufmann, Corine Martineau, Alice Arabian, Mary Traynor, René St-Arnaud, Glenville Jones. Calcioic acid: In vivo detection and quantification of the terminal C24-oxidation product of 25-hydroxyvitamin D3 and related intermediates in serum of mice treated with 24,25-dihydroxyvitamin D3. The Journal of steroid biochemistry and molecular biology. 2019 04; 188(?):23-28. doi: 10.1016/j.jsbmb.2018.12.001. [PMID: 30553931]
  • Olivia B Yu, Leggy A Arnold. Calcitroic Acid-A Review. ACS chemical biology. 2016 10; 11(10):2665-2672. doi: 10.1021/acschembio.6b00569. [PMID: 27574921]
  • Maryam Goudarzi, Siddheshwar Chauthe, Steven J Strawn, Waylon M Weber, David J Brenner, Albert J Fornace. Quantitative Metabolomic Analysis of Urinary Citrulline and Calcitroic Acid in Mice after Exposure to Various Types of Ionizing Radiation. International journal of molecular sciences. 2016 May; 17(5):. doi: 10.3390/ijms17050782. [PMID: 27213362]
  • R L Horst, J A Omdahl, S Reddy. Rat cytochrome P450C24 (CYP24) does not metabolize 1,25-dihydroxyvitamin D2 to calcitroic acid. Journal of cellular biochemistry. 2003 Feb; 88(2):282-5. doi: 10.1002/jcb.10359. [PMID: 12520527]
  • D R Zimmerman, T A Reinhardt, R Kremer, D C Beitz, G S Reddy, R L Horst. Calcitroic acid is a major catabolic metabolite in the metabolism of 1 alpha-dihydroxyvitamin D(2). Archives of biochemistry and biophysics. 2001 Aug; 392(1):14-22. doi: 10.1006/abbi.2001.2419. [PMID: 11469789]
  • G Makin, D Lohnes, V Byford, R Ray, G Jones. Target cell metabolism of 1,25-dihydroxyvitamin D3 to calcitroic acid. Evidence for a pathway in kidney and bone involving 24-oxidation. The Biochemical journal. 1989 Aug; 262(1):173-80. doi: 10.1042/bj2620173. [PMID: 2818561]
  • G S Reddy, K Y Tserng. Calcitroic acid, end product of renal metabolism of 1,25-dihydroxyvitamin D3 through C-24 oxidation pathway. Biochemistry. 1989 Feb; 28(4):1763-9. doi: 10.1021/bi00430a051. [PMID: 2719932]
  • R P Esvelt, H F De Luca. Calcitroic acid: biological activity and tissue distribution studies. Archives of biochemistry and biophysics. 1981 Feb; 206(2):403-13. doi: 10.1016/0003-9861(81)90107-7. [PMID: 6261697]
  • H K Schnoes, H F DeLuca. Recent progress in vitamin D metabolism and the chemistry of vitamin D metabolites. Federation proceedings. 1980 Aug; 39(10):2723-9. doi: NULL. [PMID: 6250910]