1.0 2011-09-21 00:38:53 UTC 2015-07-21 06:57:58 UTC FDB024038 23S,25-Dihydroxyvitamin D3 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] (3beta,5Z,7E)-9,10-Secocholesta-5,7,10(19)-triene-3,23,25-triol 23,25-Dihydroxycholecalciferol 23,25-Dihydroxyvitamin D3 23S,25-Dihydroxyvitamin D 23S,25-Dihydroxyvitamin D3 C27H44O3 416.6365 416.329045274 (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 23,25-dihydroxyvitamin d3 77733-16-5 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=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 JVBPQHSRTHJMLM-UXHBOMOISA-N belongs to the class of organic compounds known as vitamin d and derivatives. Vitamin D and derivatives are compounds containing a secosteroid backbone, usually secoergostane or secocholestane. Vitamin D and derivatives Organic compounds Lipids and lipid-like molecules Steroids and steroid derivatives Vitamin D and derivatives Aliphatic homopolycyclic compounds Cyclic alcohols and derivatives Hydrocarbon derivatives Secondary alcohols Tertiary alcohols Triterpenoids Alcohol Aliphatic homopolycyclic compound Cyclic alcohol Hydrocarbon derivative Organic oxygen compound Organooxygen compound Secondary alcohol Tertiary alcohol Triterpenoid Solid logp 5.17 ALOGPS logs -4.62 ALOGPS solubility 9.98e-03 g/l ALOGPS logp 4.19 ChemAxon pka_strongest_acidic 14.93 ChemAxon pka_strongest_basic -1.3 ChemAxon iupac (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 ChemAxon average_mass 416.6365 ChemAxon mono_mass 416.329045274 ChemAxon smiles 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 ChemAxon formula C27H44O3 ChemAxon 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 ChemAxon inchikey JVBPQHSRTHJMLM-UXHBOMOISA-N ChemAxon polar_surface_area 60.69 ChemAxon refractivity 126.69 ChemAxon polarizability 50.88 ChemAxon rotatable_bond_count 6 ChemAxon acceptor_count 3 ChemAxon donor_count 3 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Specdb::CMs 25034 Specdb::CMs 39062 Specdb::CMs 164103 Specdb::MsMs 321463 Specdb::MsMs 321464 Specdb::MsMs 321465 Specdb::MsMs 369100 Specdb::MsMs 369101 Specdb::MsMs 369102 Specdb::MsMs 2790500 Specdb::MsMs 2790501 Specdb::MsMs 2790502 Specdb::MsMs 2915453 Specdb::MsMs 2915454 Specdb::MsMs 2915455 HMDB06720 #<Reference:0x000055ce31eb9790> Anatidae Type 1 specific Anatidae 8830 Beefalo Type 1 specific Bos taurus X Bison bison 297284 Bison Type 1 specific Bison bison 9901 Buffalo Type 1 specific Bubalus bubalis 89462 Cattle (Beef, Veal) Type 1 specific Bos taurus 9913 Chicken Type 1 specific Gallus gallus 9031 Columbidae (Dove, Pigeon) Type 1 specific Columbidae 8930 Deer Type 1 specific Cervidae 9850 Domestic goat Type 1 specific Capra aegagrus hircus 9925 Domestic pig Type 1 specific Sus scrofa domestica 9825 Elk Type 1 specific Cervus canadensis 1574408 Emu Type 1 specific Dromaius novaehollandiae 8790 European rabbit Type 1 specific Oryctolagus 9984 Greylag goose Type 1 specific Anser anser 8843 Guinea hen Type 1 specific Numida meleagris 8996 Horse Type 1 specific Equus caballus 9796 Mallard duck Type 1 specific Anas platyrhynchos 8839 Mountain hare Type 1 specific Lepus timidus 62621 Mule deer Type 1 specific Odocoileus 9871 Ostrich Type 1 specific Struthio camelus 8801 Pheasant Type 1 specific Phasianus colchicus 9054 Quail Type 1 specific Phasianidae 9005 Rabbit Type 1 specific Leporidae 9979 Rock ptarmigan Type 1 specific Lagopus muta 64668 Sheep (Mutton, Lamb) Type 1 specific Ovis aries 9940 Squab Type 1 specific Columba 8931 Turkey Type 1 specific Meleagris gallopavo 9103 Velvet duck Type 1 specific Melanitta fusca 371864 Wild boar Type 1 specific Sus scrofa 9823