1.0 2016-09-30 22:28:57 UTC 2020-06-04 20:42:14 UTC BMDB0000343 BMDB00343 2-Hydroxyestrone 2-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, 2-hydroxyestrone is considered to be a steroid lipid molecule. 2-Hydroxyestrone is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. 2-Hydroxyestrone participates in a number of enzymatic reactions, within cattle. In particular, 2-Hydroxyestrone can be biosynthesized from estrone; which is catalyzed by the enzyme cytochrome P450 1A1. In addition, S-Adenosylmethionine and 2-hydroxyestrone can be converted into 2-methoxyestrone and S-adenosylhomocysteine through its interaction with the enzyme catechol O-methyltransferase. In cattle, 2-hydroxyestrone is involved in the metabolic pathway called the estrone metabolism pathway. 2,3-Dihydroxyestra-1,3,5(10)-trien-17-one 2-OHE1 Catecholestrone 2-Hydroxyestrone, 4-(14)C-labeled C18H22O3 286.3655 286.15689457 (1S,10R,11S,15S)-4,5-dihydroxy-15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-2(7),3,5-trien-14-one (1S,10R,11S,15S)-4,5-dihydroxy-15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-2(7),3,5-trien-14-one 362-06-1 [H][C@@]12CCC(=O)[C@@]1(C)CC[C@]1([H])C3=C(CC[C@@]21[H])C=C(O)C(O)=C3 InChI=1S/C18H22O3/c1-18-7-6-11-12(14(18)4-5-17(18)21)3-2-10-8-15(19)16(20)9-13(10)11/h8-9,11-12,14,19-20H,2-7H2,1H3/t11-,12+,14-,18-/m0/s1 SWINWPBPEKHUOD-JPVZDGGYSA-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-oxosteroids 3-hydroxysteroids Hydrocarbon derivatives Ketones Organic oxides Phenanthrenes and derivatives Tetralins 1-hydroxy-2-unsubstituted benzenoid 17-oxosteroid 2-hydroxysteroid 3-hydroxysteroid Aromatic homopolycyclic compound Benzenoid Carbonyl group Estrogen-skeleton Hydrocarbon derivative Hydroxysteroid Ketone Organic oxide Organic oxygen compound Organooxygen compound Oxosteroid Phenanthrene Tetralin Aromatic homopolycyclic compounds 2-hydroxy steroid C18 steroids (estrogens) and derivatives C18 steroids (estrogens) and derivatives Solid logp 3.03 ALOGPS logs -4.09 ALOGPS logp 4.01 ChemAxon pka_strongest_acidic 9.67 ChemAxon pka_strongest_basic -6.3 ChemAxon iupac (1S,10R,11S,15S)-4,5-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@@]12CCC(=O)[C@@]1(C)CC[C@]1([H])C3=C(CC[C@@]21[H])C=C(O)C(O)=C3 ChemAxon formula C18H22O3 ChemAxon inchi InChI=1S/C18H22O3/c1-18-7-6-11-12(14(18)4-5-17(18)21)3-2-10-8-15(19)16(20)9-13(10)11/h8-9,11-12,14,19-20H,2-7H2,1H3/t11-,12+,14-,18-/m0/s1 ChemAxon inchikey SWINWPBPEKHUOD-JPVZDGGYSA-N ChemAxon polar_surface_area 57.53 ChemAxon refractivity 81.06 ChemAxon polarizability 32.23 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 1280 Specdb::CMs 20421 Specdb::CMs 37447 Specdb::CMs 167397 Specdb::CMs 1059054 Specdb::CMs 1059056 Specdb::CMs 1059058 Specdb::CMs 1059060 Specdb::CMs 1059061 Specdb::CMs 1059063 Specdb::CMs 1059065 Specdb::CMs 1059067 Specdb::CMs 1059069 Specdb::CMs 1059071 Specdb::CMs 1059073 Specdb::NmrOneD 1338 Specdb::MsMs 552 Specdb::MsMs 553 Specdb::MsMs 554 Specdb::MsMs 311467 Specdb::MsMs 311468 Specdb::MsMs 311469 Specdb::MsMs 356479 Specdb::MsMs 356480 Specdb::MsMs 356481 Specdb::MsMs 2320280 Specdb::MsMs 2320281 Specdb::MsMs 2320282 Specdb::MsMs 2618801 Specdb::MsMs 2618802 Specdb::MsMs 2618803 Blood 0.000243 uM Detected by HPLC-MS/MS 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 Blood 0.0138 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 FDB021966 1156 C05298 2-Hydroxyestrone Kovacs, Katalin; Rakonczay, Z.; Matkovics, B. Steroids. XXIII. Synthesis of 2- and 4-hydroxy and 2,4-dihydroxy derivatives of estrone and estradiol. Acta Physica et Chemica (1973), 19(3), 287-90. BMDBP00421 Catechol O-methyltransferase A7MBI7 COMT Enzyme