1.0 2016-09-30 22:20:15 UTC 2020-06-04 18:59:02 UTC BMDB0000153 BMDB00153 Estriol Estriol, also known as 16a,17b-estriol or ovestin, belongs to the class of organic compounds known as estrogens and derivatives. These are steroids with a structure containing a 3-hydroxylated estrane. Thus, estriol is considered to be a steroid lipid molecule. Estriol is a drug which is used as a test to determine the general health of an unborn fetus. Estriol exists as a solid, very hydrophobic, practically insoluble (in water), and relatively neutral molecule. Estriol participates in a number of enzymatic reactions, within cattle. In particular, Estriol can be biosynthesized from 16a-hydroxyestrone; which is mediated by the enzyme estradiol 17-beta-dehydrogenase 1. In addition, Estriol can be biosynthesized from estradiol; which is mediated by the enzyme cytochrome P450 3A5. In cattle, estriol is involved in the metabolic pathway called the estrone metabolism pathway. Estriol is a potentially toxic compound. (16alpha,17beta)-Estra-1,3,5(10)-triene-3,16,17-triol 1,3,5(10)-Estratriene-3,16-alpha,17beta-triol 16alpha,17beta-Estriol 16alpha-Hydroxyestradiol 3,16alpha,17beta-Trihydroxy-Delta(1,3,5)-estratriene Deuslon-a Estriel Oestriol Trihydroxyestrin (16a,17b)-Estra-1,3,5(10)-triene-3,16,17-triol (16Α,17β)-estra-1,3,5(10)-triene-3,16,17-triol 1,3,5(10)-Estratriene-3,16-a,17b-triol 1,3,5(10)-Estratriene-3,16-α,17β-triol 16a,17b-Estriol 16Α,17β-estriol 16a-Hydroxyestradiol 16Α-hydroxyestradiol 3,16a,17b-Trihydroxy-delta(1,3,5)-estratriene 3,16Α,17β-trihydroxy-δ(1,3,5)-estratriene 3,16a,17b-Trihydroxy-δ(1,3,5)-estratriene 13b-Methyl-1,3,5(10)-gonatriene-3,16a,17b-triol 16-alpha,17-beta-Estriol 16-alpha,17-beta-Oestriol 16-alpha-Hydroxyestradiol 16a-Estriol 16alpha,17beta-Oestriol 16alpha-Hydroxy-17beta-estradiol 16alpha-Hydroxyoestradiol 3,16a,17b-Estriol 3,16a,17b-Trihydroxyestra-1,3,5(10)-triene 3,16alpha,17beta-Trihydroxy-1,3,5(10)-estratriene 3,16alpha,17beta-Trihydroxyestra-1,3,5(10)-triene Aacifemine Colpogyn Colpovister Destriol Deuslon a Estra-1,3,5(10)-triene-3,16a,17b-triol Estratriol Follicular hormone hydrate Gynasan Hemostyptanon Holin V Hormomed Incurin Klimax e Klimoral Oekolp Oestratriol Oestriolum Orestin Orgastyptin Ortho-gynest Ovesterin Ovestin Ovestinon Ovestrion Ovo-vinces Theelol Tridestrin Triovex 16-alpha-Hydroxy-estradiol (16beta,17beta)-Estra-1,3,5(10)-triene-3,16,17-triol 16beta Hydroxy estradiol 16beta-Hydroxy-estradiol Epiestriol 16 alpha Hydroxy estradiol 16alpha,17beta Estriol Estra-1,3,5(10)-triene-3,16beta,17beta-triol 13beta-Methyl-1,3,5(10)-gonatriene-3,16alpha,17beta-triol 13β-Methyl-1,3,5(10)-gonatriene-3,16α,17β-triol 16alpha-Estriol 16α-Estriol 3,16alpha,17beta-Estriol 3,16α,17β-Estriol 3,16α,17β-Trihydroxyestra-1,3,5(10)-triene Estriol C18H24O3 288.3814 288.172544634 (1S,10R,11S,13R,14R,15S)-15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-2(7),3,5-triene-5,13,14-triol (1S,10R,11S,13R,14R,15S)-15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-2(7),3,5-triene-5,13,14-triol 50-27-1 [H][C@@]12C[C@@H](O)[C@H](O)[C@@]1(C)CC[C@]1([H])C3=C(CC[C@@]21[H])C=C(O)C=C3 InChI=1S/C18H24O3/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/h3,5,8,13-17,19-21H,2,4,6-7,9H2,1H3/t13-,14-,15+,16-,17+,18+/m1/s1 PROQIPRRNZUXQM-ZXXIGWHRSA-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 1,2-diols 1-hydroxy-2-unsubstituted benzenoids 16-alpha-hydroxysteroids 17-hydroxysteroids 3-hydroxysteroids Cyclic alcohols and derivatives Hydrocarbon derivatives Phenanthrenes and derivatives Secondary alcohols Tetralins 1,2-diol 1-hydroxy-2-unsubstituted benzenoid 16-alpha-hydroxysteroid 16-hydroxysteroid 17-hydroxysteroid 3-hydroxysteroid Alcohol Aromatic homopolycyclic compound Benzenoid Cyclic alcohol Estrogen-skeleton Hydrocarbon derivative Hydroxysteroid Organic oxygen compound Organooxygen compound Phenanthrene Polyol Secondary alcohol Tetralin Aromatic homopolycyclic compounds 16alpha-hydroxy steroid 17beta-hydroxy steroid 3-hydroxy steroid C18 steroids (estrogens) and derivatives C18 steroids (estrogens) and derivatives Estrane and derivatives Estrogens Solid melting_point 282 °C logp 2.45 HANSCH,C ET AL. (1995) logp 2.54 ALOGPS logs -3.38 ALOGPS logp 2.67 ChemAxon pka_strongest_acidic 10.33 ChemAxon pka_strongest_basic -3.2 ChemAxon iupac (1S,10R,11S,13R,14R,15S)-15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-2(7),3,5-triene-5,13,14-triol ChemAxon average_mass 288.3814 ChemAxon mono_mass 288.172544634 ChemAxon smiles [H][C@@]12C[C@@H](O)[C@H](O)[C@@]1(C)CC[C@]1([H])C3=C(CC[C@@]21[H])C=C(O)C=C3 ChemAxon formula C18H24O3 ChemAxon inchi InChI=1S/C18H24O3/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/h3,5,8,13-17,19-21H,2,4,6-7,9H2,1H3/t13-,14-,15+,16-,17+,18+/m1/s1 ChemAxon inchikey PROQIPRRNZUXQM-ZXXIGWHRSA-N ChemAxon polar_surface_area 60.69 ChemAxon refractivity 81.27 ChemAxon polarizability 33.08 ChemAxon rotatable_bond_count 0 ChemAxon acceptor_count 3 ChemAxon donor_count 3 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::EiMs 127 Specdb::NmrOneD 1114 Specdb::NmrTwoD 1173 Specdb::CMs 2191 Specdb::CMs 8866 Specdb::CMs 27517 Specdb::CMs 31028 Specdb::CMs 37325 Specdb::CMs 168636 Specdb::CMs 1051680 Specdb::CMs 1051682 Specdb::CMs 1051684 Specdb::CMs 1051686 Specdb::CMs 1051688 Specdb::CMs 1051690 Specdb::CMs 1051692 Specdb::CMs 1051694 Specdb::CMs 1051695 Specdb::CMs 1051697 Specdb::CMs 1051699 Specdb::CMs 1051701 Specdb::CMs 1051703 Specdb::MsMs 236 Specdb::MsMs 237 Specdb::MsMs 238 Specdb::MsMs 3118 Specdb::MsMs 262296 Specdb::MsMs 262297 Specdb::MsMs 262298 Specdb::MsMs 282228 Specdb::MsMs 282229 Specdb::MsMs 282230 Specdb::MsMs 439748 Specdb::MsMs 2244040 Specdb::MsMs 2246065 Specdb::MsMs 2248144 Specdb::MsMs 2248255 Specdb::MsMs 2250137 Specdb::MsMs 2250289 Specdb::MsMs 2252088 Specdb::MsMs 2442742 Specdb::MsMs 2442743 Specdb::MsMs 2442744 Specdb::MsMs 2519139 Specdb::MsMs 2519140 Specdb::MsMs 2519141 Adrenal Cortex 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 Adrenal Gland 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 8 multiparous Chinese Holstein dairy cows fed in the Hangzhou Hangjiang Dairy Farm based on the milk production under corn stover based diets. Detection used gas chromatography time-of-flight/mass spectrometry (GC-TOF/MS) platform. Sun HZ, Zhou M, Wang O, Chen Y, Liu JX, Guan LL: Multi-omics reveals functional genomic and metabolic mechanisms of milk production and quality in dairy cows. Bioinformatics. 2020 Apr 15;36(8):2530-2537. doi: 10.1093/bioinformatics/btz951. 31873721 Liver 8 multiparous Chinese Holstein dairy cows fed in the Hangzhou Hangjiang Dairy Farm based on the milk production under alfalfa hay based diets. Detection used gas chromatography time-of-flight/mass spectrometry (GC-TOF/MS) platform. Sun HZ, Zhou M, Wang O, Chen Y, Liu JX, Guan LL: Multi-omics reveals functional genomic and metabolic mechanisms of milk production and quality in dairy cows. Bioinformatics. 2020 Apr 15;36(8):2530-2537. doi: 10.1093/bioinformatics/btz951. 31873721 Milk 0.00002843 +/- 0.00001 uM commercial skim milk Wolford ST, Argoudelis CJ: Measurement of estrogens in cow's milk, human milk, and dairy products. J Dairy Sci. 1979 Sep;62(9):1458-63. doi: 10.3168/jds.S0022-0302(79)83446-3. 512140 Milk 0.00003121 +/- 0.000006935 uM Commercial whole milk Wolford ST, Argoudelis CJ: Measurement of estrogens in cow's milk, human milk, and dairy products. J Dairy Sci. 1979 Sep;62(9):1458-63. doi: 10.3168/jds.S0022-0302(79)83446-3. 512140 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 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 C05141 5553 DB04573 FDB006781 5756 27974 ESTRIOL Estriol 45207 2581 Leeds, Norma S.; Fukushima, David K.; Gallagher, T. F. Studies of steroid ring D epoxides of enol acetates; a new synthesis of estriol and of androstane-3b,16a,17b-triol. Journal of the American Chemical Society (1954), 76 2943-8. Wolford ST, Argoudelis CJ: Measurement of estrogens in cow's milk, human milk, and dairy products. J Dairy Sci. 1979 Sep;62(9):1458-63. doi: 10.3168/jds.S0022-0302(79)83446-3. 512140