23S,25-Dihydroxyvitamin D3
IUPAC 名称
(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
描述
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]
异构
OC(C[C@@H](C)[C@H]1CCC2([H])\C(CCC[C@]12C)=C\C=C1\C[C@H](O)CCC1=C)CC(O)(C)C
InChI标识符
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
键
JVBPQHSRTHJMLM-UXHBOMOISA-N