23S,25-dihydroxyvitamin D3 (BioDeep_00000023541)

   

human metabolite Endogenous


代谢物信息卡片


(6R)-6-[(1R,4E,7aR)-4-{2-[(1Z,5R)-5-hydroxy-2-methylidenecyclohexylidene]ethylidene}-7a-methyl-octahydro-1H-inden-1-yl]-2-methylheptane-2,4-diol

化学式: C27H44O3 (416.3290274)
中文名称:
谱图信息: 最多检出来源 () 0%

分子结构信息

SMILES: C=C1CCC(O)CC1=CC=C1CCCC2(C)C1CCC2C(C)CC(O)CC(C)(C)O
InChI: InChI=1S/C27H44O3/c1-18-8-11-22(28)16-21(18)10-9-20-7-6-14-27(5)24(12-13-25(20)27)19(2)15-23(29)17-26(3,4)30/h9-10,19,22-25,28-30H,1,6-8,11-17H2,2-5H3/b20-9+,21-10-/t19-,22-,23?,24-,25?,27-/m1/s1

描述信息

23S,25-dihydroxyvitamin D3 (23S,25-(OH)2D3) is a circulating metabolite of vitamin D3 during vitamin D excess. During hypocalcemia or hypovitaminosis D, 25-OH-D3 is 1alpha-hydroxylated, primarily in kidney, to produce 1,25-(OH)2D3. 1,25-(OH)2D3 is a hormonally active form of vitamin D3 that enhances intestinal calcium transport and promotes mobilization of calcium from bone. In states of vitamin D excess, other pathways of 25-OH-D3 metabolism emerge as alternatives to 1-and 24-hydroxylation. Recently, 25-hydroxyvitamin D3-26,23-lactone (lactone) was identified as a major plasma metabolite in animals receiving large doses of vitamin D. Although the function of the lactone is not known, its 5-fold greater potency of binding to the plasma vitamin D carrier protein, relative to 25-OH-D3, suggests that it may, perhaps indirectly, contribute to vitamin D toxicity. This indicates the existence of an alternate route to lactone formation through a new 25-OH-D3 metabolite, 23,25-(OH)2D3. (PMID: 6286629) [HMDB]
23S,25-dihydroxyvitamin D3 (23S,25-(OH)2D3) is a circulating metabolite of vitamin D3 during vitamin D excess. During hypocalcemia or hypovitaminosis D, 25-OH-D3 is 1alpha-hydroxylated, primarily in kidney, to produce 1,25-(OH)2D3. 1,25-(OH)2D3 is a hormonally active form of vitamin D3 that enhances intestinal calcium transport and promotes mobilization of calcium from bone. In states of vitamin D excess, other pathways of 25-OH-D3 metabolism emerge as alternatives to 1-and 24-hydroxylation. Recently, 25-hydroxyvitamin D3-26,23-lactone (lactone) was identified as a major plasma metabolite in animals receiving large doses of vitamin D. Although the function of the lactone is not known, its 5-fold greater potency of binding to the plasma vitamin D carrier protein, relative to 25-OH-D3, suggests that it may, perhaps indirectly, contribute to vitamin D toxicity. This indicates the existence of an alternate route to lactone formation through a new 25-OH-D3 metabolite, 23,25-(OH)2D3. (PMID: 6286629).
D018977 - Micronutrients > D014815 - Vitamins > D004100 - Dihydroxycholecalciferols
D018977 - Micronutrients > D014815 - Vitamins > D006887 - Hydroxycholecalciferols

同义名列表

10 个代谢物同义名

(6R)-6-[(1R,4E,7aR)-4-{2-[(1Z,5R)-5-hydroxy-2-methylidenecyclohexylidene]ethylidene}-7a-methyl-octahydro-1H-inden-1-yl]-2-methylheptane-2,4-diol; (3beta,5Z,7E)-9,10-Secocholesta-5,7,10(19)-triene-3,23,25-triol; 23,25-Dihydroxyvitamin D3, (3beta,5Z,7E,23S)-isomer; 23,25-Dihydroxyvitamin D3, (3beta,5Z,7E,23R)-isomer; 23,25-Dihydroxycholecalciferol; 23, 25-Dihydroxy Vitamin D3; 23S,25-dihydroxyvitamin D3; 23S, 25 Dihydroxyvitamin D; 23,25-Dihydroxyvitamin D3; 23S,25-Dihydroxyvitamin D



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代谢反应

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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：

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文献列表

  • J I Pedersen, Y Hagenfeldt, I Björkhem. Assay and properties of 25-hydroxyvitamin D3 23-hydroxylase. Evidence that 23,25-dihydroxyvitamin D3 is a major metabolite in 1,25-dihydroxyvitamin D3-treated or fasted guinea pigs. The Biochemical journal. 1988 Mar; 250(2):527-32. doi: 10.1042/bj2500527. [PMID: 3355535]
  • S Shany, J Rapoport, I Zuili, N Yankowitz, C Chaimovitz. Enhancement of 24,25-dihydroxyvitamin D levels in patients treated with continuous ambulatory peritoneal dialysis. Nephron. 1986; 42(2):141-5. doi: 10.1159/000183653. [PMID: 3003603]
  • S Ishizuka, A W Norman. Stereo-retained and stereo-selective lactonization of four diastereoisomers of 23,25,26-trihydroxyvitamin D3 in homogenates of kidney from vitamin D-supplemented chicks. Archives of biochemistry and biophysics. 1984 Jan; 228(1):179-84. doi: 10.1016/0003-9861(84)90059-6. [PMID: 6546486]
  • R L Horst, T A Reinhardt, B C Pramanik, J L Napoli. 23-Keto-25-hydroxyvitamin D3: a vitamin D3 metabolite with high affinity for the 1,25-dihydroxyvitamin D specific cytosol receptor. Biochemistry. 1983 Jan; 22(2):245-50. doi: 10.1021/bi00271a002. [PMID: 6297543]
  • J L Napoli, B C Pramanik, J J Partridge, M R Uskoković, R L Horst. 23S,25-dihydroxyvitamin D3 as a circulating metabolite of vitamin D3. Its role in 25-hydroxyvitamin D3-26,23-lactone biosynthesis. The Journal of biological chemistry. 1982 Aug; 257(16):9634-9. doi: 10.1016/s0021-9258(18)34119-x. [PMID: 6286629]
  • S Ishizuka, S Ishimoto, A W Norman. Metabolic pathway to 25-hydroxyvitamin D3-26,23-lactone from 25-hydroxyvitamin D3. FEBS letters. 1982 Feb; 138(1):83-7. doi: 10.1016/0014-5793(82)80400-6. [PMID: 7067832]
  • Y Tanaka, J K Wichmann, H K Schnoes, H F DeLuca. Isolation and identification of 23,25-dihydroxyvitamin D3, an in vivo metabolite of vitamin D3. Biochemistry. 1981 Jun; 20(13):3875-9. doi: 10.1021/bi00516a032. [PMID: 6268149]