1.0 2016-09-30 22:38:19 UTC 2020-06-04 20:39:02 UTC BMDB0000900 BMDB00900 Ergocalciferol Ergocalciferol, also known as vitamin D2 or viosterol, 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, ergocalciferol is considered to be a secosteroid lipid molecule. Ergocalciferol is a drug which is used for use in the management of hypocalcemia and its clinical manifestations in patients with hypoparathyroidism, as well as for the treatment of familial hypophosphatemia (vitamin d resistant rickets). this drug has also been used in the treatment of nutritional rickets or osteomalacia, vitamin d dependent rickets, rickets or osteomalacia secondary to long-term high dose anticonvulsant therapy, early renal osteodystrophy, osteoporosis (in conjunction with calcium), and hypophosphatemia associated with fanconi syndrome (with treatment of acidosis). Ergocalciferol exists as a solid, very hydrophobic, practically insoluble (in water), and relatively neutral molecule. Ergocalciferol is a potentially toxic compound. (3beta,5Z,7E,22E)-9,10-Secoergosta-5,7,10(19),22-tetraen-3-ol (5Z,7E,22E)-(3S)-9,10-Seco-5,7,10(19),22-ergostatetraen-3-ol (5Z,7E,22E)-(3S)-9,10-Secoergosta-5,7,10(19),22-tetraen-3-ol Activated ergosterol Calciferol Ercalciol Ergocalciferolum Oleovitamin D2 Viosterol Vitamina D2 Vitamin D2 Drisdol (3b,5Z,7E,22E)-9,10-Secoergosta-5,7,10(19),22-tetraen-3-ol (3Β,5Z,7E,22E)-9,10-secoergosta-5,7,10(19),22-tetraen-3-ol (+)-Vitamin D2 (5E,7E,22E)-9,10-Secoergosta-5,7,10,22-tetraen-3-ol 22-Tetraen 3beta 9,10,secoergosta-5,7,10(19)-ol 4-Methylene-3-[2-[tetrahydro-7a-methyl-1-(1,4,5-trimethyl-2-hexenyl)-4(3ah)-indanylidene]ethylidene]-cyclohexanol 9,10-Secoergosta-5,7,10(19),22-tetraen-3b-ol beta-Ol Buco-D Calciferon 2 Condacaps Condocaps Condol Crtron Crystallina D-Arthin D-Tracetten Daral Davitamon D Davitin De-rat concentrate Decaps Dee-osterol Dee-ron Dee-ronal Dee-roual delta-Arthin delta-Tracetten Deltalin Deratol Detalup Diactol Divit urto Doral Ergocalciferol oil Ergorone Ergosterol activated Ergosterol irradiated Ertron Fortodyl Geltabs Hi-deratol Infron Irradiated ergosta-5,7,22-trien-3beta-ol Metadee Mina D2 Mulsiferol Mykostin Novovitamin-D Oleovitamin D Osteil Ostelin Radiostol Radstein Radsterin Rodine C Shock-ferol Shock-ferol sterogyl Sterogyl Synthetic vitamin D Uvesterol D Uvesterol-D Vio D Vio-D Viostdrol Viosterol in oil Vitavel-D Calciferols Ergocalciferols D2, Vitamin Vitamin D 2 Ergocalciferol C28H44O 396.6484 396.33921603 (1S,3Z)-3-{2-[(1R,3aS,4E,7aR)-1-[(2R,3E,5R)-5,6-dimethylhept-3-en-2-yl]-7a-methyl-octahydro-1H-inden-4-ylidene]ethylidene}-4-methylidenecyclohexan-1-ol ergocalciferol 50-14-6 [H][C@@]1(CC[C@@]2([H])\C(CCC[C@]12C)=C\C=C1\C[C@@H](O)CCC1=C)[C@H](C)\C=C\[C@H](C)C(C)C InChI=1S/C28H44O/c1-19(2)20(3)9-10-22(5)26-15-16-27-23(8-7-17-28(26,27)6)12-13-24-18-25(29)14-11-21(24)4/h9-10,12-13,19-20,22,25-27,29H,4,7-8,11,14-18H2,1-3,5-6H3/b10-9+,23-12+,24-13-/t20-,22+,25-,26+,27-,28+/m0/s1 MECHNRXZTMCUDQ-RKHKHRCZSA-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 Triterpenoids Alcohol Aliphatic homopolycyclic compound Cyclic alcohol Hydrocarbon derivative Organic oxygen compound Organooxygen compound Secondary alcohol Triterpenoid Aliphatic homopolycyclic compounds Fat-soluble vitamins Vitamin D2 and derivatives Vitamin D2 and derivatives hydroxy seco-steroid seco-ergostane vitamin D Solid melting_point 116.5 °C water_solubility 0.05 mg/mL logp 7.59 ALOGPS logs -5.96 ALOGPS logp 7.05 ChemAxon pka_strongest_acidic 18.38 ChemAxon pka_strongest_basic -1.3 ChemAxon iupac (1S,3Z)-3-{2-[(1R,3aS,4E,7aR)-1-[(2R,3E,5R)-5,6-dimethylhept-3-en-2-yl]-7a-methyl-octahydro-1H-inden-4-ylidene]ethylidene}-4-methylidenecyclohexan-1-ol ChemAxon average_mass 396.6484 ChemAxon mono_mass 396.33921603 ChemAxon smiles [H][C@@]1(CC[C@@]2([H])\C(CCC[C@]12C)=C\C=C1\C[C@@H](O)CCC1=C)[C@H](C)\C=C\[C@H](C)C(C)C ChemAxon formula C28H44O ChemAxon inchi InChI=1S/C28H44O/c1-19(2)20(3)9-10-22(5)26-15-16-27-23(8-7-17-28(26,27)6)12-13-24-18-25(29)14-11-21(24)4/h9-10,12-13,19-20,22,25-27,29H,4,7-8,11,14-18H2,1-3,5-6H3/b10-9+,23-12+,24-13-/t20-,22+,25-,26+,27-,28+/m0/s1 ChemAxon inchikey MECHNRXZTMCUDQ-RKHKHRCZSA-N ChemAxon polar_surface_area 20.23 ChemAxon refractivity 128.89 ChemAxon polarizability 50.72 ChemAxon rotatable_bond_count 5 ChemAxon acceptor_count 1 ChemAxon donor_count 1 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::NmrTwoD 1534 Specdb::NmrOneD 1593 Specdb::CMs 2233 Specdb::CMs 12356 Specdb::CMs 31259 Specdb::CMs 37831 Specdb::CMs 148015 Specdb::CMs 1081137 Specdb::MsMs 1277 Specdb::MsMs 1278 Specdb::MsMs 1279 Specdb::MsMs 4826 Specdb::MsMs 254724 Specdb::MsMs 254725 Specdb::MsMs 254726 Specdb::MsMs 274665 Specdb::MsMs 274666 Specdb::MsMs 274667 Specdb::MsMs 448217 Specdb::MsMs 2295135 Specdb::MsMs 2295136 Specdb::MsMs 2295137 Specdb::MsMs 2640622 Specdb::MsMs 2640623 Specdb::MsMs 2640624 Adipose 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 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 Brain 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 Liver 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 0.000126 uM Milk, partly skim, conventional (not organic), 1.5 % fat Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/ShowFood.php?foodid=33&2 Milk 0.000126 uM Milk, partly skim, organic, 1.5 % fat Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/ShowFood.php?foodid=1154&2 Milk 0.000176 uM Milk, s Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/ShowFood.php?foodid=1049&2 Milk 0.00192 uM Milk, skim, 0.5 % fat Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/ShowFood.php?foodid=1066&2 Milk 0.000176 uM Skim milk, organic Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/ShowFood.php?foodid=1048&2 Milk 0.00252 uM Milk, whole, 3.5, (UHT), % fat Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/ShowFood.php?foodid=1265&2 Milk 0.000227 uM Milk, whole, conventional (not organic), 3.5 % fat Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/ShowFood.php?foodid=6&2 Milk 0.000202 uM Milk, whole, organic, 3.5 % fat Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/ShowFood.php?foodid=1266&2 Milk 0.0003 +/- 0.0001 uM Quantified by LC-MS/MS in 1% milk Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204. 30994344 Milk 0.0003 +/- 0.0002 uM Quantified by LC-MS/MS in 2% milk Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204. 30994344 Milk 0.0003 +/- 0.0001 uM Quantified by LC-MS/MS in 3.25% milk Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204. 30994344 Milk 0.0003 +/- 0.0001 uM Quantified by LC-MS/MS in skim milk Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204. 30994344 Milk 0.000504 uM Pirjo H. Mattila, Vieno I. Piironen, Esko J. Uusi-Rauva, and Pekka E. Koivistoinen. 1995. Contents of Cholecalciferol, Ergocalciferol, and Their 25-Hydroxylated Metabolites in Milk Products and Raw Meat and Liver As Determined by HPLC. J. Agric. Food Chem. 43 (9), pp 2394–2399 Neuron 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 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 C05441 5280793 4444351 DB00153 FDB012811 28934 VITAMIN_D2 Ergocalciferol 2289183 5856 Okabe, Masami. Vitamin D2 from ergosterol (9,10-secoergosta-5,7,10(19),22-tetraen-3-ol,(3b)- from ergosta-5,7,22-trien-3-ol,(3b)-). Organic Syntheses (1999), 76 275-286. A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation) Pirjo H. Mattila, Vieno I. Piironen, Esko J. Uusi-Rauva, and Pekka E. Koivistoinen. 1995. Contents of Cholecalciferol, Ergocalciferol, and Their 25-Hydroxylated Metabolites in Milk Products and Raw Meat and Liver As Determined by HPLC. J. Agric. Food Chem. 43 (9), pp 2394–2399 Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/ShowFood.php?foodid=33&2 Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/ShowFood.php?foodid=1154&2 Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/ShowFood.php?foodid=1049&2 Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/ShowFood.php?foodid=1066&2 Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/ShowFood.php?foodid=1048&2 Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/ShowFood.php?foodid=1265&2 Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/ShowFood.php?foodid=6&2 Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/ShowFood.php?foodid=1266&2