1.0 2011-09-21 00:35:41 UTC 2015-07-21 06:57:54 UTC FDB023845 Ercalcitriol Ercalcitriol is the active circulating metabolite of vitamin D2. Vitamin D2 is modified by 25-hydroxylase in the liver and 25-hydroxyvitamin D *-hydroxylase in the kidney to form the active metabolite, ercalcitriol, which is then metabolized by 25-hydroxyvitamin D-24-hydroxylase (24-OHase, CYP24A1, EC 1.14.13.13). The binding of ercalcitriol or their analogs to Vitamin D receptor (VDR), a nuclear receptor, activates VDR to interact with retinoid X receptor (RXR) and forms the VDR/RXR/cofactor complex, which binds to Vitamin D response elements in the promoter region of target genes to regulate gene transcription. The kidney is the major site of 25-hydroxyvitamin D*-hydroxylase (CYP27B1, EC 1.14.13.13), which is responsible for the activation of 25-hydroxyvitamin D. Of all the steroid hormones, ercalcitriol represents the most difficult challenge to the analytical biochemist with respect to quantization. Ercalcitriol circulates at pmol concentrations, is highly lipophilic and its precursor, 25-hydroxyvitamin D2, circulates at nmol levels. (PMID: 16242929, 17867378, 17197173) [HMDB] 1,25-Dihydroxycalciferol 1,25-Dihydroxyergocalciferol 1,25-Dihydroxyvitamin D2 1a,25-Dihydroxycalciferol 1a,25-Dihydroxyergocalciferol 1a,25-Dihydroxyvitamin D2 Ro 17-6218 C28H44O3 428.6472 428.329045274 (1R,3S,5Z)-5-{2-[(1R,3aS,7aR)-1-[(2R,5S)-6-hydroxy-5,6-dimethylhept-3-en-2-yl]-7a-methyl-octahydro-1H-inden-4-ylidene]ethylidene}-4-methylidenecyclohexane-1,3-diol (1R,3S,5Z)-5-{2-[(1R,3aS,7aR)-1-[(2R,5S)-6-hydroxy-5,6-dimethylhept-3-en-2-yl]-7a-methyl-hexahydro-1H-inden-4-ylidene]ethylidene}-4-methylidenecyclohexane-1,3-diol 60133-18-8 [H]C(=C[C@@](C)([H])C(C)(C)O)[C@](C)([H])[C@@]1([H])CC[C@@]2([H])C(CCC[C@]12C)=C\C=C1\C[C@](O)([H])C[C@@](O)([H])C1=C InChI=1S/C28H44O3/c1-18(9-10-19(2)27(4,5)31)24-13-14-25-21(8-7-15-28(24,25)6)11-12-22-16-23(29)17-26(30)20(22)3/h9-12,18-19,23-26,29-31H,3,7-8,13-17H2,1-2,4-6H3/b10-9?,21-11?,22-12-/t18-,19+,23-,24-,25+,26+,28-/m1/s1 ZGLHBRQAEXKACO-FNCRLDAWSA-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 5.45 ALOGPS logs -4.79 ALOGPS solubility 7.03e-03 g/l ALOGPS logp 4.35 ChemAxon pka_strongest_acidic 14.39 ChemAxon pka_strongest_basic -1 ChemAxon iupac (1R,3S,5Z)-5-{2-[(1R,3aS,7aR)-1-[(2R,5S)-6-hydroxy-5,6-dimethylhept-3-en-2-yl]-7a-methyl-octahydro-1H-inden-4-ylidene]ethylidene}-4-methylidenecyclohexane-1,3-diol ChemAxon average_mass 428.6472 ChemAxon mono_mass 428.329045274 ChemAxon smiles [H]C(=C[C@@](C)([H])C(C)(C)O)[C@](C)([H])[C@@]1([H])CC[C@@]2([H])C(CCC[C@]12C)=C\C=C1\C[C@](O)([H])C[C@@](O)([H])C1=C ChemAxon formula C28H44O3 ChemAxon inchi InChI=1S/C28H44O3/c1-18(9-10-19(2)27(4,5)31)24-13-14-25-21(8-7-15-28(24,25)6)11-12-22-16-23(29)17-26(30)20(22)3/h9-12,18-19,23-26,29-31H,3,7-8,13-17H2,1-2,4-6H3/b10-9?,21-11?,22-12-/t18-,19+,23-,24-,25+,26+,28-/m1/s1 ChemAxon inchikey ZGLHBRQAEXKACO-FNCRLDAWSA-N ChemAxon polar_surface_area 60.69 ChemAxon refractivity 132.12 ChemAxon polarizability 52.31 ChemAxon rotatable_bond_count 5 ChemAxon acceptor_count 3 ChemAxon donor_count 3 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon HMDB06225 #<Reference:0x000055ce33175d70> #<Reference:0x000055ce33175bb8> #<Reference:0x000055ce33175a00> 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