1.0 2016-09-30 22:48:51 UTC 2020-06-04 18:58:59 UTC BMDB0001903 BMDB01903 Calcitriol Calcitriol, also known as 1a,25(OH)2D3 or calcitriol-nefro, 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. Thus, calcitriol is considered to be a secosteroid lipid molecule. Calcitriol is a drug which is used to treat vitamin d deficiency or insufficiency, refractory rickets (vitamin d resistant rickets), familial hypophosphatemia and hypoparathyroidism, and in the management of hypocalcemia and renal osteodystrophy in patients with chronic renal failure undergoing dialysis. also used in conjunction with calcium in the management and prevention of primary or corticosteroid-induced osteoporosis. Calcitriol exists as a solid, very hydrophobic, practically insoluble (in water), and relatively neutral molecule. Calcitriol is a potentially toxic compound. (1alpha,3beta,5Z,7E)-9,10-Secocholesta-5,7,10(19)-triene-1,3,25-triol (1S,3R,5Z,7E)-9,10-Secocholesta-5,7,10-triene-1,3,25-triol (5Z,7E)-(1S,3R)-9,10-Secocholesta-5,7,10(19)-triene-1,3,25-triol 1,25-DHCC 1-alpha-25-Dihydroxyvitamin D3 1alpha,25(OH)2D3 1alpha,25-Dihydroxycholecalciferol 1alpha,25-Dihydroxyvitamin D3 5-{2-[1-(5-hydroxy-1,5-dimethyl-hexyl)-7a-methyl-octahydro-inden-4-ylidene]-ethylidene}-4-methylene-cyclohexane-1,3-diol Calcijex Calcitriolum Decostriol Rocaltrol (1S,3R,5Z,7E)-9,10-Seco-5,7,10(19)-cholestatriene-1,3,25-triol (1a,3b,5Z,7E)-9,10-Secocholesta-5,7,10(19)-triene-1,3,25-triol (1Α,3β,5Z,7E)-9,10-secocholesta-5,7,10(19)-triene-1,3,25-triol 1-a-25-Dihydroxyvitamin D3 1-Α-25-dihydroxyvitamin D3 1a,25(OH)2D3 1Α,25(OH)2D3 1a,25-Dihydroxycholecalciferol 1Α,25-dihydroxycholecalciferol 1a,25-Dihydroxyvitamin D3 1Α,25-dihydroxyvitamin D3 (3b,5Z,7E)-9,10-Secocholesta-5,7,10(19)-trienetriol 1,25 Dihydroxycholecalciferol 1,25-Dihydroxycholecalciferol 1,25-Dihydroxyvitamin D 1,25-Dihydroxyvitamin D3 1-alpha,25-Dihydroxyvitamin D3 1a,25-(OH)2D3 25-Dihydroxycholecalciferol Dihydroxyvitamin D3 Ro 21-5535 Silkis Soltriol Topitriol Toptriol 1 alpha, 25-Dihydroxy-20-epi-vitamin D3 1 alpha,25-Dihydroxycholecalciferol 1,25(OH)2-20EPi-D3 Bocatriol Calcitriol alphapharm brand Calcitriol kyramed Calcitriol-nefro Hoffmann-la roche brand OF calcitriol KyraMed, calcitriol Tirocal alpha,25-Dihydroxyvitamin D3, 1 1,25-Dihydroxy-20-epi-vitamin D3 20 Epi 1alpha,25 dihydroxycholecaliferol Abbott brand OF calcitriol Calcitriol galderma brand Calcitriol jenapharm brand Calcitriol leo brand Cryopharma brand OF calcitriol Medice brand OF calcitriol Renatriol Roche brand OF calcitriol 1 alpha,25 Dihydroxycholecalciferol 1 alpha,25-Dihydroxyvitamin D3 20-Epi-1alpha,25-dihydroxycholecaliferol Calcitriol gry brand Calcitriol kyramed brand Calcitriol medice brand Calcitriol nefro Calcitriol renacare brand Calcitriol roche brand D3, 1,25-Dihydroxyvitamin D3, 1,25-Dihydroxy-20-epi-vitamin Galderma brand OF calcitriol Hoffmann la roche brand OF calcitriol KyraMed brand OF calcitriol Leo brand OF calcitriol RenaCare brand OF calcitriol Sitriol 1 alpha, 25 Dihydroxy 20 epi vitamin D3 1 alpha,25 Dihydroxyvitamin D3 1,25 Dihydroxyvitamin D3 1,25 Dihydroxy 20 epi vitamin D3 Alphapharm brand OF calcitriol Calcitriol abbott brand Calcitriol cryopharma brand CalcitriolNefro D3, 1 alpha,25-Dihydroxyvitamin Gry brand OF calcitriol Jenapharm brand OF calcitriol Osteotriol 1a,25-Dihydroxyvitamin D3 / 1a,25-dihydroxycholecalciferol / calcitriol 1Α,25-dihydroxyvitamin D3 / 1α,25-dihydroxycholecalciferol / calcitriol Calcitriol C27H44O3 416.6365 416.329045274 (1R,3S,5Z)-5-{2-[(1R,3aS,4E,7aR)-1-[(2R)-6-hydroxy-6-methylheptan-2-yl]-7a-methyl-octahydro-1H-inden-4-ylidene]ethylidene}-4-methylidenecyclohexane-1,3-diol calcitriol 32222-06-3 C[C@H](CCCC(C)(C)O)[C@@]1([H])CC[C@@]2([H])\C(CCC[C@]12C)=C\C=C1\C[C@@H](O)C[C@H](O)C1=C InChI=1S/C27H44O3/c1-18(8-6-14-26(3,4)30)23-12-13-24-20(9-7-15-27(23,24)5)10-11-21-16-22(28)17-25(29)19(21)2/h10-11,18,22-25,28-30H,2,6-9,12-17H2,1,3-5H3/b20-10+,21-11-/t18-,22-,23-,24+,25+,27-/m1/s1 GMRQFYUYWCNGIN-NKMMMXOESA-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. Organic compounds Lipids and lipid-like molecules Steroids and steroid derivatives Vitamin D and derivatives Vitamin D and derivatives 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 Aliphatic homopolycyclic compounds D3 vitamins Steroid hormones Vitamin D3 and derivatives hydroxycalciol triol Solid melting_point 113 °C logp 5.51 ALOGPS logs -4.80 ALOGPS logp 4.35 ChemAxon pka_strongest_acidic 14.39 ChemAxon pka_strongest_basic -1.3 ChemAxon iupac (1R,3S,5Z)-5-{2-[(1R,3aS,4E,7aR)-1-[(2R)-6-hydroxy-6-methylheptan-2-yl]-7a-methyl-octahydro-1H-inden-4-ylidene]ethylidene}-4-methylidenecyclohexane-1,3-diol ChemAxon average_mass 416.6365 ChemAxon mono_mass 416.329045274 ChemAxon smiles C[C@H](CCCC(C)(C)O)[C@@]1([H])CC[C@@]2([H])\C(CCC[C@]12C)=C\C=C1\C[C@@H](O)C[C@H](O)C1=C ChemAxon formula C27H44O3 ChemAxon inchi InChI=1S/C27H44O3/c1-18(8-6-14-26(3,4)30)23-12-13-24-20(9-7-15-27(23,24)5)10-11-21-16-22(28)17-25(29)19(21)2/h10-11,18,22-25,28-30H,2,6-9,12-17H2,1,3-5H3/b20-10+,21-11-/t18-,22-,23-,24+,25+,27-/m1/s1 ChemAxon inchikey GMRQFYUYWCNGIN-NKMMMXOESA-N ChemAxon polar_surface_area 60.69 ChemAxon refractivity 126.53 ChemAxon polarizability 51.02 ChemAxon rotatable_bond_count 6 ChemAxon acceptor_count 3 ChemAxon donor_count 3 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 3 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon Specdb::MsMs 81324 Specdb::MsMs 81325 Specdb::MsMs 81326 Specdb::MsMs 142413 Specdb::MsMs 142414 Specdb::MsMs 142415 Specdb::MsMs 2288514 Specdb::MsMs 2288515 Specdb::MsMs 2288516 Specdb::MsMs 2647332 Specdb::MsMs 2647333 Specdb::MsMs 2647334 Specdb::CMs 25450 Specdb::CMs 38179 Specdb::CMs 172771 Adrenal Medulla Wishart DS, Feunang YD, Marcu A, Guo AC, Liang K, Vazquez-Fresno R, Sajed T, Johnson D, Li C, Karu N, Sayeeda Z, Lo E, Assempour N, Berjanskii M, Singhal S, Arndt D, Liang Y, Badran H, Grant J, Serra-Cayuela A, Liu Y, Mandal R, Neveu V, Pon A, Knox C, Wilson M, Manach C, Scalbert A: HMDB 4.0: the human metabolome database for 2018. Nucleic Acids Res. 2018 Jan 4;46(D1):D608-D617. doi: 10.1093/nar/gkx1089. 29140435 Bladder Wishart DS, Feunang YD, Marcu A, Guo AC, Liang K, Vazquez-Fresno R, Sajed T, Johnson D, Li C, Karu N, Sayeeda Z, Lo E, Assempour N, Berjanskii M, Singhal S, Arndt D, Liang Y, Badran H, Grant J, Serra-Cayuela A, Liu Y, Mandal R, Neveu V, Pon A, Knox C, Wilson M, Manach C, Scalbert A: HMDB 4.0: the human metabolome database for 2018. Nucleic Acids Res. 2018 Jan 4;46(D1):D608-D617. doi: 10.1093/nar/gkx1089. 29140435 Epidermis Wishart DS, Feunang YD, Marcu A, Guo AC, Liang K, Vazquez-Fresno R, Sajed T, Johnson D, Li C, Karu N, Sayeeda Z, Lo E, Assempour N, Berjanskii M, Singhal S, Arndt D, Liang Y, Badran H, Grant J, Serra-Cayuela A, Liu Y, Mandal R, Neveu V, Pon A, Knox C, Wilson M, Manach C, Scalbert A: HMDB 4.0: the human metabolome database for 2018. Nucleic Acids Res. 2018 Jan 4;46(D1):D608-D617. doi: 10.1093/nar/gkx1089. 29140435 Fibroblasts Wishart DS, Feunang YD, Marcu A, Guo AC, Liang K, Vazquez-Fresno R, Sajed T, Johnson D, Li C, Karu N, Sayeeda Z, Lo E, Assempour N, Berjanskii M, Singhal S, Arndt D, Liang Y, Badran H, Grant J, Serra-Cayuela A, Liu Y, Mandal R, Neveu V, Pon A, Knox C, Wilson M, Manach C, Scalbert A: HMDB 4.0: the human metabolome database for 2018. Nucleic Acids Res. 2018 Jan 4;46(D1):D608-D617. doi: 10.1093/nar/gkx1089. 29140435 Intestine Wishart DS, Feunang YD, Marcu A, Guo AC, Liang K, Vazquez-Fresno R, Sajed T, Johnson D, Li C, Karu N, Sayeeda Z, Lo E, Assempour N, Berjanskii M, Singhal S, Arndt D, Liang Y, Badran H, Grant J, Serra-Cayuela A, Liu Y, Mandal R, Neveu V, Pon A, Knox C, Wilson M, Manach C, Scalbert A: HMDB 4.0: the human metabolome database for 2018. Nucleic Acids Res. 2018 Jan 4;46(D1):D608-D617. doi: 10.1093/nar/gkx1089. 29140435 Kidney Wishart DS, Feunang YD, Marcu A, Guo AC, Liang K, Vazquez-Fresno R, Sajed T, Johnson D, Li C, Karu N, Sayeeda Z, Lo E, Assempour N, Berjanskii M, Singhal S, Arndt D, Liang Y, Badran H, Grant J, Serra-Cayuela A, Liu Y, Mandal R, Neveu V, Pon A, Knox C, Wilson M, Manach C, Scalbert A: HMDB 4.0: the human metabolome database for 2018. Nucleic Acids Res. 2018 Jan 4;46(D1):D608-D617. doi: 10.1093/nar/gkx1089. 29140435 Milk 0.00001296 +/- 0.00000288 uM Raw milk Hollis BW, Roos BA, Draper HH, Lambert PW: Vitamin D and its metabolites in human and bovine milk. J Nutr. 1981 Jul;111(7):1240-8. doi: 10.1093/jn/111.7.1240. 6788913 Ovary Wishart DS, Feunang YD, Marcu A, Guo AC, Liang K, Vazquez-Fresno R, Sajed T, Johnson D, Li C, Karu N, Sayeeda Z, Lo E, Assempour N, Berjanskii M, Singhal S, Arndt D, Liang Y, Badran H, Grant J, Serra-Cayuela A, Liu Y, Mandal R, Neveu V, Pon A, Knox C, Wilson M, Manach C, Scalbert A: HMDB 4.0: the human metabolome database for 2018. Nucleic Acids Res. 2018 Jan 4;46(D1):D608-D617. doi: 10.1093/nar/gkx1089. 29140435 Pancreas Wishart DS, Feunang YD, Marcu A, Guo AC, Liang K, Vazquez-Fresno R, Sajed T, Johnson D, Li C, Karu N, Sayeeda Z, Lo E, Assempour N, Berjanskii M, Singhal S, Arndt D, Liang Y, Badran H, Grant J, Serra-Cayuela A, Liu Y, Mandal R, Neveu V, Pon A, Knox C, Wilson M, Manach C, Scalbert A: HMDB 4.0: the human metabolome database for 2018. Nucleic Acids Res. 2018 Jan 4;46(D1):D608-D617. doi: 10.1093/nar/gkx1089. 29140435 Placenta Wishart DS, Feunang YD, Marcu A, Guo AC, Liang K, Vazquez-Fresno R, Sajed T, Johnson D, Li C, Karu N, Sayeeda Z, Lo E, Assempour N, Berjanskii M, Singhal S, Arndt D, Liang Y, Badran H, Grant J, Serra-Cayuela A, Liu Y, Mandal R, Neveu V, Pon A, Knox C, Wilson M, Manach C, Scalbert A: HMDB 4.0: the human metabolome database for 2018. Nucleic Acids Res. 2018 Jan 4;46(D1):D608-D617. doi: 10.1093/nar/gkx1089. 29140435 Prostate Tissue Wishart DS, Feunang YD, Marcu A, Guo AC, Liang K, Vazquez-Fresno R, Sajed T, Johnson D, Li C, Karu N, Sayeeda Z, Lo E, Assempour N, Berjanskii M, Singhal S, Arndt D, Liang Y, Badran H, Grant J, Serra-Cayuela A, Liu Y, Mandal R, Neveu V, Pon A, Knox C, Wilson M, Manach C, Scalbert A: HMDB 4.0: the human metabolome database for 2018. Nucleic Acids Res. 2018 Jan 4;46(D1):D608-D617. doi: 10.1093/nar/gkx1089. 29140435 Skeletal Muscle Wishart DS, Feunang YD, Marcu A, Guo AC, Liang K, Vazquez-Fresno R, Sajed T, Johnson D, Li C, Karu N, Sayeeda Z, Lo E, Assempour N, Berjanskii M, Singhal S, Arndt D, Liang Y, Badran H, Grant J, Serra-Cayuela A, Liu Y, Mandal R, Neveu V, Pon A, Knox C, Wilson M, Manach C, Scalbert A: HMDB 4.0: the human metabolome database for 2018. Nucleic Acids Res. 2018 Jan 4;46(D1):D608-D617. doi: 10.1093/nar/gkx1089. 29140435 Spleen Wishart DS, Feunang YD, Marcu A, Guo AC, Liang K, Vazquez-Fresno R, Sajed T, Johnson D, Li C, Karu N, Sayeeda Z, Lo E, Assempour N, Berjanskii M, Singhal S, Arndt D, Liang Y, Badran H, Grant J, Serra-Cayuela A, Liu Y, Mandal R, Neveu V, Pon A, Knox C, Wilson M, Manach C, Scalbert A: HMDB 4.0: the human metabolome database for 2018. Nucleic Acids Res. 2018 Jan 4;46(D1):D608-D617. doi: 10.1093/nar/gkx1089. 29140435 Testis Wishart DS, Feunang YD, Marcu A, Guo AC, Liang K, Vazquez-Fresno R, Sajed T, Johnson D, Li C, Karu N, Sayeeda Z, Lo E, Assempour N, Berjanskii M, Singhal S, Arndt D, Liang Y, Badran H, Grant J, Serra-Cayuela A, Liu Y, Mandal R, Neveu V, Pon A, Knox C, Wilson M, Manach C, Scalbert A: HMDB 4.0: the human metabolome database for 2018. Nucleic Acids Res. 2018 Jan 4;46(D1):D608-D617. doi: 10.1093/nar/gkx1089. 29140435 DB00136 FDB021822 4444108 C01673 5280453 17823 CALCITRIOL 2289241 Calcitriol 6382 Chen, Yang-sheng; Zhai, Cui-yun; Ren, Li. Synthesis of calcitriol. Zhongguo Xinyao Zazhi (2005), 14(1), 69-72. Hollis BW, Roos BA, Draper HH, Lambert PW: Vitamin D and its metabolites in human and bovine milk. J Nutr. 1981 Jul;111(7):1240-8. doi: 10.1093/jn/111.7.1240. 6788913 BMDBP01912 Vitamin D3 receptor Q28037 VDR Enzyme