1.0 2016-09-30 22:28:49 UTC 2020-06-04 20:40:02 UTC BMDB0000335 BMDB00335 16a-Hydroxyestrone 16a-Hydroxyestrone, also known as 16a-hydroxyestrone or 16a-hydroxyestrone, belongs to the class of organic compounds known as estrogens and derivatives. These are steroids with a structure containing a 3-hydroxylated estrane. Thus, 16a-hydroxyestrone is considered to be a steroid lipid molecule. 16a-Hydroxyestrone is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. 16a-Hydroxyestrone participates in a number of enzymatic reactions, within cattle. In particular, 16a-Hydroxyestrone can be biosynthesized from estrone; which is catalyzed by the enzyme cytochrome P450 3A5. In addition, 16a-Hydroxyestrone can be converted into estriol through its interaction with the enzyme estradiol 17-beta-dehydrogenase 1. In cattle, 16a-hydroxyestrone is involved in the metabolic pathway called the estrone metabolism pathway. 16 alpha OHE 3,16alpha-Dihydroxy-1,3,5(10)-estratrien-17-one 3,16alpha-Dihydroxyestra-1,3,5(10)-trien-17-one Estra-1,3,5(10)-triene-3,16alpha-diol-17-one 16 a OHE 16 Α ohe 3,16a-Dihydroxy-1,3,5(10)-estratrien-17-one 3,16Α-dihydroxy-1,3,5(10)-estratrien-17-one 3,16a-Dihydroxyestra-1,3,5(10)-trien-17-one 3,16Α-dihydroxyestra-1,3,5(10)-trien-17-one Estra-1,3,5(10)-triene-3,16a-diol-17-one Estra-1,3,5(10)-triene-3,16α-diol-17-one 16 alpha-Hydroxyestrone 3,16a-Dihydroxy-estra-1,3,5(10)-trien-17-one 16 beta-Hydroxyestrone 16-alpha-Hydroxyestrone 16-Hydroxyestrone C18H22O3 286.3655 286.15689457 (1S,10R,11S,13R,15S)-5,13-dihydroxy-15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-2(7),3,5-trien-14-one (1S,10R,11S,13R,15S)-5,13-dihydroxy-15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-2(7),3,5-trien-14-one 566-76-7 [H][C@@]12C[C@@H](O)C(=O)[C@@]1(C)CC[C@]1([H])C3=C(CC[C@@]21[H])C=C(O)C=C3 InChI=1S/C18H22O3/c1-18-7-6-13-12-5-3-11(19)8-10(12)2-4-14(13)15(18)9-16(20)17(18)21/h3,5,8,13-16,19-20H,2,4,6-7,9H2,1H3/t13-,14-,15+,16-,18+/m1/s1 WPOCIZJTELRQMF-QFXBJFAPSA-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 16-alpha-hydroxysteroids 17-oxosteroids 3-hydroxysteroids Cyclic alcohols and derivatives Hydrocarbon derivatives Ketones Organic oxides Phenanthrenes and derivatives Secondary alcohols Tetralins 1-hydroxy-2-unsubstituted benzenoid 16-alpha-hydroxysteroid 16-hydroxysteroid 17-oxosteroid 3-hydroxysteroid Alcohol Aromatic homopolycyclic compound Benzenoid Carbonyl group Cyclic alcohol Estrogen-skeleton Hydrocarbon derivative Hydroxysteroid Ketone Organic oxide Organic oxygen compound Organooxygen compound Oxosteroid Phenanthrene Secondary alcohol Tetralin Aromatic homopolycyclic compounds 16alpha-hydroxy steroid C18 steroids (estrogens) and derivatives Solid logp 2.45 ALOGPS logs -3.79 ALOGPS logp 3.44 ChemAxon pka_strongest_acidic 10.33 ChemAxon pka_strongest_basic -3.5 ChemAxon iupac (1S,10R,11S,13R,15S)-5,13-dihydroxy-15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-2(7),3,5-trien-14-one ChemAxon average_mass 286.3655 ChemAxon mono_mass 286.15689457 ChemAxon smiles [H][C@@]12C[C@@H](O)C(=O)[C@@]1(C)CC[C@]1([H])C3=C(CC[C@@]21[H])C=C(O)C=C3 ChemAxon formula C18H22O3 ChemAxon inchi InChI=1S/C18H22O3/c1-18-7-6-13-12-5-3-11(19)8-10(12)2-4-14(13)15(18)9-16(20)17(18)21/h3,5,8,13-16,19-20H,2,4,6-7,9H2,1H3/t13-,14-,15+,16-,18+/m1/s1 ChemAxon inchikey WPOCIZJTELRQMF-QFXBJFAPSA-N ChemAxon polar_surface_area 57.53 ChemAxon refractivity 80.57 ChemAxon polarizability 32.06 ChemAxon rotatable_bond_count 0 ChemAxon acceptor_count 3 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 Estrone Metabolism SMP0087272 Specdb::NmrTwoD 1276 Specdb::NmrOneD 1333 Specdb::MsMs 310075 Specdb::MsMs 310076 Specdb::MsMs 310077 Specdb::MsMs 354667 Specdb::MsMs 354668 Specdb::MsMs 354669 Specdb::MsMs 2453569 Specdb::MsMs 2453570 Specdb::MsMs 2453571 Specdb::MsMs 2484648 Specdb::MsMs 2484649 Specdb::MsMs 2484650 Specdb::CMs 2146 Specdb::CMs 2155 Specdb::CMs 19794 Specdb::CMs 31127 Specdb::CMs 31128 Specdb::CMs 37440 Specdb::CMs 154728 Specdb::CMs 1058842 Specdb::CMs 1058844 Specdb::CMs 1058846 Specdb::CMs 1058848 Specdb::CMs 1058850 Specdb::CMs 1058851 Specdb::CMs 1058853 Specdb::CMs 1058855 Specdb::CMs 1058857 Specdb::CMs 1058859 Specdb::CMs 1058860 Blood 0.00151 uM Detected by HPLC-MS/MS in Holstein cows. Regal P, Nebot C, Diaz-Bao M, Barreiro R, Cepeda A, Fente C: Disturbance in sex-steroid serum profiles of cattle in response to exogenous estradiol: a screening approach to detect forbidden treatments. Steroids. 2011 Mar;76(4):365-75. doi: 10.1016/j.steroids.2010.12.005. Epub 2010 Dec 21. 21172370 FDB021959 103012 115116 C05300 776 2580 Knuppen, R.; Breuer, H. Biogenesis of 11b-hydroxyestrone and 16a-hydroxyestrone by adrenal tissue. Biochimica et Biophysica Acta (1962), 58 147-8.