Compound: Erteberel
SMILES: O1c2c(cc(O)cc2)[C@@H]3CCC[C@@H]3[C@@H]1c4ccc(O)cc4
InChIKey: XIESSJVMWNJCGZ-VKJFTORMSA-N
Synonyms: Erteberel, 533884-09-2, LY500307, SERBA-1, LY-500307, 2ZUL6758TZ, DTXSID70201547, (3aS,4R,9bR)-1,2,3,3a,4,9b-Hexahydro-4-(4-hydroxyphenyl)cyclopenta[c][1]benzopyran-8-ol, Cyclopenta(c)(1)benzopyran-8-ol, 1,2,3,3a,4,9b-hexahydro-4-(4-hydroxyphenyl)-, (3aS,4R,9bR)-, erteberelum, (3aS,4R,9bR)-1,2,3,3a,4,9b-Hexahydro-4-(4-hydroxyphenyl)cyclopenta(c)(1)benzopyran-8-ol, RefChem:591094, DTXCID00124038, (2R,6S,7R)-7-(4-hydroxyphenyl)-8-oxatricyclo(7.4.0.02,?)trideca-1(9),10,12-trien-12-ol, (3aS,4R,9bR)-4-(4-hydroxyphenyl)-1,2,3,3a,4,9b-hexahydrocyclopenta[c]chromen-8-ol, Erteberel (LY500307), Benzopyran derivative., 4b(racemate), (3aS,4R,9bR)-4-(4-Hydroxyphenyl)-1,2,3,3a,4,9b-hexahydrocyclopenta(c)(1) benzopyran-8-ol, I0G, Erteberel [USAN], Erteberel [USAN:INN], UNII-2ZUL6758TZ, 2i0g, 2i0j, ERTEBEREL [INN], Erteberel (USAN/INN), LY 500307, ERTEBEREL [WHO-DD], CHEMBL278703, orb1300884, SCHEMBL14102383, BDBM19968, EX-A157, GLXC-15787, MFCD22495234, AKOS027323752, DB07933, NCGC00346557-01, NCGC00346557-02, AC-36799, HY-18295, MS-24010, CS-0007402, NS00070542, D09899, BRD-K80608265-001-01-6, Q27097167, (3aS,4R,9bR)-4-(4-Hydroxyphenyl)-1,2,3,3a,4,9b-hexahydrobenzo[b]cyclopenta[d]pyran-8-ol, (2R,6S,7R)-7-(4-hydroxyphenyl)-8-oxatricyclo[7.4.0.0;{2,6}]trideca-1(13),9,11-trien-12-ol, (2R,6S,7R)-7-(4-hydroxyphenyl)-8-oxatricyclo[7.4.0.0;{2,6}]trideca-1(9),10,12-trien-12-ol, (3AS,4R,9BR)-4-(4-HYDROXYPHENYL)-1,2,3,3A,4,9B-HEXAHYDROCYCLOPENTA(C)(1)BENZOPYRAN-8-OL
Theoretical properties:
molecular_formula: C18H18O3
molecular_weight: 282.3 g/mol
exact_mass: 282.125594432 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 2
hydrogen_bond_acceptor_count: 3
rotatable_bond_count: 1
heavy_atom_count: 21
topological_polar_surface_area: 49.7 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
Descriptions:
{"pubchem": null, "chebi": "An organic heterotricyclic compound that is 1,2,3,3a,4,9b-hexahydrocyclopenta[<em>c</em>]chromene substituted by 4-hydroxyphenyl and hydroxy groups at positions 4 and 8, respectively (the 3a<i>S</i>,4<i>R</i>,9b<i>R</i>-stereoisomer). It is an estrogen receptor \u03b2 agonist and exhibits antineoplastic activity.", "chembl": "ERTEBEREL is a small molecule listed in the ChEMBL database and has reached clinical trial phase 2.0.", "wikipedia": "Erteberel (INNTooltip International Nonproprietary Name, USANTooltip United States Adopted Name; former developmental code name LY-500307; also known as selective estrogen receptor beta agonist-1 or SERBA-1) is a synthetic, nonsteroidal estrogen which acts as a selective ER\u03b2 agonist and was under development by Eli Lilly for the treatment of schizophrenia. It was specifically under investigation for the treatment of negative symptoms and cognitive impairment associated with the condition. It managed to reach phase II clinical trials for this indication in the United States in 2015. As of 2021 development has been discontinued. Erteberel was also under investigation for the treatment of benign prostatic hyperplasia and reached phase II clinical studies for this use but failed to improve symptoms in men with the condition and development for this indication was discontinued. The drug has also been proposed as a potential novel treatment for glioblastoma.\nErteberel has 14-fold binding selectivity for the ER\u03b2 over the ER\u03b1 (Ki = 0.19 nM versus 2.68 nM, respectively). However, it shows 32-fold functional selectivity for activation of the ER\u03b2 over the ER\u03b1 (EC50 = 0.66 nM versus 19.4 nM, respectively). It is roughly a full agonist of both the ER\u03b2 and ER\u03b1 (Emax = 101% versus 94%, respectively). Although selective for the ER\u03b2, erteberel loses its selectivity at high dosages and activates the ER\u03b1 as well, producing effects such as suppression of gonadal testosterone production in men."}