1.0 2016-09-30 22:28:35 UTC 2020-05-11 18:23:18 UTC BMDB0000322 BMDB00322 16-Oxoandrostenediol (3b,17b)-3b,17b-Dihydroxyandrost-5-en-16-one 3b,17b-Dihydroxy-androst-5-en-16-one 3b,17b-Dihydroxyandrost-5-en-16-one 3beta,17beta-Dihydroxy-androst-5-en-16-one 5-Androsten-3b,17b-diol-16-one Androst-5-ene-3b,17b-diol-16-one C19H28O3 304.4238 304.203844762 (2R,5S,14R,15S)-5,14-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-13-one 5-androsten-3b,17b-diol-16-one 1159-66-6 C[C@]12CCC3C(CC=C4C[C@@H](O)CC[C@]34C)C1CC(=O)[C@@H]2O InChI=1S/C19H28O3/c1-18-7-5-12(20)9-11(18)3-4-13-14(18)6-8-19(2)15(13)10-16(21)17(19)22/h3,12-15,17,20,22H,4-10H2,1-2H3/t12-,13?,14?,15?,17-,18-,19-/m0/s1 AKRBLZKRYPEVIK-IACDPKRHSA-N belongs to the class of organic compounds known as androgens and derivatives. These are 3-hydroxylated C19 steroid hormones. They are known to favor the development of masculine characteristics. They also show profound effects on scalp and body hair in humans. Organic compounds Lipids and lipid-like molecules Steroids and steroid derivatives Androstane steroids Androgens and derivatives 16-oxosteroids 17-hydroxysteroids 3-beta-hydroxy delta-5-steroids 3-beta-hydroxysteroids Cyclic alcohols and derivatives Cyclic ketones Delta-5-steroids Hydrocarbon derivatives Organic oxides Secondary alcohols 16-oxosteroid 17-hydroxysteroid 3-beta-hydroxy-delta-5-steroid 3-beta-hydroxysteroid 3-hydroxy-delta-5-steroid 3-hydroxysteroid Alcohol Aliphatic homopolycyclic compound Androgen-skeleton Carbonyl group Cyclic alcohol Cyclic ketone Delta-5-steroid Hydrocarbon derivative Hydroxysteroid Ketone Organic oxide Organic oxygen compound Organooxygen compound Oxosteroid Secondary alcohol Aliphatic homopolycyclic compounds Solid melting_point 203 - 205 °C logp 2.39 ALOGPS logs -3.39 ALOGPS logp 2.13 ChemAxon pka_strongest_acidic 12.97 ChemAxon pka_strongest_basic -1.4 ChemAxon iupac (2R,5S,14R,15S)-5,14-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-13-one ChemAxon average_mass 304.4238 ChemAxon mono_mass 304.203844762 ChemAxon smiles C[C@]12CCC3C(CC=C4C[C@@H](O)CC[C@]34C)C1CC(=O)[C@@H]2O ChemAxon formula C19H28O3 ChemAxon inchi InChI=1S/C19H28O3/c1-18-7-5-12(20)9-11(18)3-4-13-14(18)6-8-19(2)15(13)10-16(21)17(19)22/h3,12-15,17,20,22H,4-10H2,1-2H3/t12-,13?,14?,15?,17-,18-,19-/m0/s1 ChemAxon inchikey AKRBLZKRYPEVIK-IACDPKRHSA-N ChemAxon polar_surface_area 57.53 ChemAxon refractivity 85.95 ChemAxon polarizability 34.66 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 Specdb::MsMs 25241 Specdb::MsMs 25242 Specdb::MsMs 25243 Specdb::MsMs 31799 Specdb::MsMs 31800 Specdb::MsMs 31801 Specdb::MsMs 3058483 Specdb::MsMs 3058484 Specdb::MsMs 3058485 Specdb::MsMs 3108151 Specdb::MsMs 3108152 Specdb::MsMs 3108153 Specdb::CMs 18927 Specdb::CMs 37430 Specdb::CMs 137408 Specdb::CMs 145142 Specdb::CMs 1058408 Specdb::CMs 1058410 Specdb::CMs 1058412 Specdb::CMs 1058414 Specdb::CMs 1058416 Specdb::CMs 1058418 Specdb::CMs 1058420 Specdb::CMs 1058422 Specdb::CMs 1058424 Specdb::CMs 1058427 Specdb::CMs 1058429 Specdb::CMs 1058431 Specdb::CMs 1058433 Specdb::CMs 1058435 Specdb::CMs 1058437 Specdb::CMs 1058439 Specdb::CMs 1058441 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 FDB021948 53477682 5311 Aoki, Terumi; Yamamura, Hiroko; Takei, Kyoko; Mori, Hiromu. Synthesis of 16-oxygenated androst-5-en-3b-ol derivatives. Chemical & Pharmaceutical Bulletin (1964), 12(7), 808-12.