1.0 2016-09-30 22:30:36 UTC 2020-06-04 20:43:46 UTC BMDB0000429 BMDB00429 17a-Estradiol 17a-Estradiol, also known as alpha-estradiol or estradiol-17alpha, belongs to the class of organic compounds known as estrogens and derivatives. These are steroids with a structure containing a 3-hydroxylated estrane. Thus, 17a-estradiol is considered to be a steroid lipid molecule. 17a-Estradiol exists as a solid, very hydrophobic, practically insoluble (in water), and relatively neutral molecule. 17a-Estradiol is a potentially toxic compound. 17a-Estradiol has been linked to the inborn metabolic disorders including glutaryl-coa dehydrogenase deficiency (gdhd). Alfatradiol alpha-Estradiol Estra-1,3,5(10)trien-3,17alpha-diol Estradiol-17alpha a-Estradiol Α-estradiol Estra-1,3,5(10)trien-3,17a-diol Estra-1,3,5(10)trien-3,17α-diol Estradiol-17a Estradiol-17α 17a-Estradiol 17Α-estradiol 1,3,5-Estratriene-3,17a-diol 13b-Methyl-1,3,5(10)-gonatriene-3,17a-diol 17-Epiestradiol 17a-Oestradiol 3,17-Dihydroxyestratriene 3,17a-Dihydroxyestra-1,3,5(10)-triene 3,17a-Dihydroxyoestra-1,3,5(10)-triene Epiestradiol Epiestrol Estra-1,3,5(10)-triene-3,17a-diol Oestra-1,3,5(10)-triene-3,17a-diol 17alpha-Estradiol C18H24O2 272.382 272.177630012 (1S,10R,11S,14R,15S)-15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-2(7),3,5-triene-5,14-diol (1S,10R,11S,14R,15S)-15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-2(7),3,5-triene-5,14-diol 57-91-0 [H][C@@]12CC[C@@H](O)[C@@]1(C)CC[C@]1([H])C3=C(CC[C@@]21[H])C=C(O)C=C3 InChI=1S/C18H24O2/c1-18-9-8-14-13-5-3-12(19)10-11(13)2-4-15(14)16(18)6-7-17(18)20/h3,5,10,14-17,19-20H,2,4,6-9H2,1H3/t14-,15-,16+,17-,18+/m1/s1 VOXZDWNPVJITMN-SFFUCWETSA-N belongs to the class of organic compounds known as estrogens and derivatives. These are steroids with a structure containing a 3-hydroxylated estrane. Organic compounds Lipids and lipid-like molecules Steroids and steroid derivatives Estrane steroids Estrogens and derivatives 1-hydroxy-2-unsubstituted benzenoids 17-hydroxysteroids 3-hydroxysteroids Cyclic alcohols and derivatives Hydrocarbon derivatives Phenanthrenes and derivatives Secondary alcohols Tetralins 1-hydroxy-2-unsubstituted benzenoid 17-hydroxysteroid 3-hydroxysteroid Alcohol Aromatic homopolycyclic compound Benzenoid Cyclic alcohol Estrogen-skeleton Hydrocarbon derivative Hydroxysteroid Organic oxygen compound Organooxygen compound Phenanthrene Secondary alcohol Tetralin Aromatic homopolycyclic compounds 17alpha-hydroxy steroid 3-hydroxy steroid C18 steroids (estrogens) and derivatives C18 steroids (estrogens) and derivatives Estrane and derivatives estradiol Solid melting_point 216 - 219 °C water_solubility 0.0039 mg/mL logp 3.57 ALOGPS logs -4.11 ALOGPS logp 3.75 ChemAxon pka_strongest_acidic 10.33 ChemAxon pka_strongest_basic -0.88 ChemAxon iupac (1S,10R,11S,14R,15S)-15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-2(7),3,5-triene-5,14-diol ChemAxon average_mass 272.382 ChemAxon mono_mass 272.177630012 ChemAxon smiles [H][C@@]12CC[C@@H](O)[C@@]1(C)CC[C@]1([H])C3=C(CC[C@@]21[H])C=C(O)C=C3 ChemAxon formula C18H24O2 ChemAxon inchi InChI=1S/C18H24O2/c1-18-9-8-14-13-5-3-12(19)10-11(13)2-4-15(14)16(18)6-7-17(18)20/h3,5,10,14-17,19-20H,2,4,6-9H2,1H3/t14-,15-,16+,17-,18+/m1/s1 ChemAxon inchikey VOXZDWNPVJITMN-SFFUCWETSA-N ChemAxon polar_surface_area 40.46 ChemAxon refractivity 79.9 ChemAxon polarizability 31.93 ChemAxon rotatable_bond_count 0 ChemAxon acceptor_count 2 ChemAxon donor_count 2 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 4 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon Specdb::EiMs 155 Specdb::NmrOneD 1367 Specdb::NmrTwoD 1311 Specdb::CMs 2059 Specdb::CMs 16289 Specdb::CMs 31143 Specdb::CMs 37528 Specdb::CMs 155771 Specdb::CMs 1062350 Specdb::CMs 1062352 Specdb::CMs 1062353 Specdb::CMs 1062355 Specdb::CMs 1062357 Specdb::MsMs 632 Specdb::MsMs 633 Specdb::MsMs 634 Specdb::MsMs 302086 Specdb::MsMs 302087 Specdb::MsMs 302088 Specdb::MsMs 344722 Specdb::MsMs 344723 Specdb::MsMs 344724 Specdb::MsMs 2236098 Specdb::MsMs 2237301 Specdb::MsMs 2238170 Specdb::MsMs 2239392 Specdb::MsMs 2240315 Specdb::MsMs 2241408 Specdb::MsMs 2242400 Specdb::MsMs 2243444 Specdb::MsMs 2248658 Specdb::MsMs 2249715 Specdb::MsMs 2428351 Specdb::MsMs 2428352 Specdb::MsMs 2428353 Specdb::MsMs 2506529 Specdb::MsMs 2506530 Specdb::MsMs 2506531 Milk Milk from Friesuan Holstein cows (n=1035) Melzer N, Wittenburg D, Hartwig S, Jakubowski S, Kesting U, Willmitzer L, Lisec J, Reinsch N, Repsilber D: Investigating associations between milk metabolite profiles and milk traits of Holstein cows. J Dairy Sci. 2013 Mar;96(3):1521-34. doi: 10.3168/jds.2012-5743. 23438684 Milk 0.000145 +/- 0.00003928 uM Whole milk (commercial) Courant F, Antignac JP, Maume D, Monteau F, Andre F, Le Bizec B: Determination of naturally occurring oestrogens and androgens in retail samples of milk and eggs. Food Addit Contam. 2007 Dec;24(12):1358-66. doi: 10.1080/02652030701329637. 17852390 Milk 0.000111 uM Half skim milk Colazo MG, Ambrose DJ, Kastelic JP, Small JA: Comparison of 2 enzyme immunoassays and a radioimmunoassay for measurement of progesterone concentrations in bovine plasma, skim milk, and whole milk. Can J Vet Res. 2008 Jan;72(1):32-6. 18214159 Milk 0.000116 uM Whole milk Courant F, Antignac JP, Laille J, Monteau F, Andre F, Le Bizec B: Exposure assessment of prepubertal children to steroid endocrine disruptors. 2. Determination of steroid hormones in milk, egg, and meat samples. J Agric Food Chem. 2008 May 14;56(9):3176-84. doi: 10.1021/jf800096f. Epub 2008 Apr 16. 18412364 FDB112198 C02537 61840 17160 68570 17α-Estradiol 5418 Gardi, Rinaldo; Pedrali, Cesare; Ercoli, Alberto. 3-Cyclopentyl ethers of 16,17-oxygenated estrogens. New synthesis of 17a-estradiol. Gazzetta Chimica Italiana (1963), 93(8-9), 1028-43. Courant F, Antignac JP, Maume D, Monteau F, Andre F, Le Bizec B: Determination of naturally occurring oestrogens and androgens in retail samples of milk and eggs. Food Addit Contam. 2007 Dec;24(12):1358-66. doi: 10.1080/02652030701329637. 17852390 Colazo MG, Ambrose DJ, Kastelic JP, Small JA: Comparison of 2 enzyme immunoassays and a radioimmunoassay for measurement of progesterone concentrations in bovine plasma, skim milk, and whole milk. Can J Vet Res. 2008 Jan;72(1):32-6. 18214159 Courant F, Antignac JP, Laille J, Monteau F, Andre F, Le Bizec B: Exposure assessment of prepubertal children to steroid endocrine disruptors. 2. Determination of steroid hormones in milk, egg, and meat samples. J Agric Food Chem. 2008 May 14;56(9):3176-84. doi: 10.1021/jf800096f. Epub 2008 Apr 16. 18412364 Melzer N, Wittenburg D, Hartwig S, Jakubowski S, Kesting U, Willmitzer L, Lisec J, Reinsch N, Repsilber D: Investigating associations between milk metabolite profiles and milk traits of Holstein cows. J Dairy Sci. 2013 Mar;96(3):1521-34. doi: 10.3168/jds.2012-5743. 23438684