Compound: 2-Methoxyestradiol
SMILES: O(c1c(O)cc2CC[C@@H]3[C@@H](c2c1)CC[C@]4([C@H]3CC[C@@H]4O)C)C
InChIKey: CQOQDQWUFQDJMK-SSTWWWIQSA-N
Synonyms: 2-Methoxyestradiol, 362-07-2, Panzem, 2-Methoxyestradiol-17beta, 2-Hydroxyestradol 2-methyl ether, 2-ME2, 2ME2, 2-methoxy-17beta-estradiol, 2-methoxyoestradiol, (17beta)-2-Methoxyestra-1,3,5(10)-triene-3,17-diol, NSC-659853, 2-Methoxyestra-1,3,5(10)-triene-3,17beta-diol, 6I2QW73SR5, DTXSID3040938, Estra-1,3,5(10)-triene-3,17-diol, 2-methoxy-, (17beta)-, 2-methoxy-estra-1,3,5(10)-triene-3,17beta-diol, (8R,9S,13S,14S,17S)-2-methoxy-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthrene-3,17-diol, CHEBI:28955, 2 Methoxyestradiol, 2 Methoxyoestradiol, 2 Methoxyestradiol 17 beta, (8R,9S,13S,14S,17S)-2-methoxy-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta(a)phenanthrene-3,17-diol, RefChem:388747, DTXCID1020938, (17 beta)-2-methoxyestra-1,3,5(10)-triene-3,17-diol, 636-846-8, 2-Methoxyestradiol (2-MeOE2), Estradiol, 2-methoxy-, 2-Hydroxyestradiol 2-methyl ether, 2-Methoxy-beta-estradiol, MFCD00010489, 2-Methoxy-estradiol, (8R,9S,13S,14S,17S)-2-methoxy-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthrene-3,17-diol, 2-Methoxy 17b-Estradiol, MLS000028819, CHEMBL299613, Panzem NCD, 1,3,5(10)-ESTRATRIEN-2,3,17-BETA-TRIOL 2-METHYL ETHER, Estra-1,3,5(10)-triene-3,17beta-diol, 2-methoxy-, 2-MeOE2, SMR000058478, PulmoLAR, 2-Methoxy-.beta.-estradiol, NSC 659853, UNII-6I2QW73SR5, CCRIS 9405, 1lhw, 2-methoxy Estradiol, 2-Methoxyestradiol?, Opera_ID_634, Estra-1,3,5(10)-triene-3,17-diol, 2-methoxy-, (17b)-, 2-Methoxyestradiol Powder, 2-Methoxyestradiol, powder, 2-Methoxy 17?-Estradiol, M 6383, SCHEMBL8796, 2-MeO-E2, 2-Methoxy 17beta-Estradiol, Lopac0_000739, MLS001076279, MLS006010142, orb1306072, orb3141073, SCHEMBL29357742, GTPL12058, MSK2646, HMS2230L22, HMS3262C20, HMS3412H22, HMS3676H22, HMS6018B16, 2-METHOXYESTRADIOL [WHO-DD], 2-METHOXYOESTRADIOL [MART.], Tox21_500739, BDBM50060957, EBC-17051, LMST02010035, MSK2646-100A, s1233, AKOS015901723, 2-Methoxyestradiol, analytical standard, CCG-204824, CS-0176, DB02342, FM25168, LP00739, SDCCGSBI-0050717.P002, SMP2_000045, NCGC00094082-03, NCGC00094082-04, NCGC00094082-13, NCGC00261424-01, (1S,3aS,3bR,9bS,11aS)-8-methoxy-11a-methyl-1H,2H,3H,3aH,3bH,4H,5H,9bH,10H,11H,11aH-cyclopenta[a]phenanthrene-1,7-diol, AC-32086, AS-19175, BP-25393, DA-69803, HY-12033, SY108908, EU-0100739, M2530, NS00014681, C05302, C74863, 2-Methoxyestra-1,3,5(10)-triene-3,17b-diol, AB00639611-09, AB00639611_10, SR-01000076000, 2-methoxy-1,3,5 (10)-estratriene-3,17beta-diol, 2-Methoxyestra-1(10),2,4-triene-3,17beta-diol, 2-Methoxyestra-1,3,5(10)-triene-3,17-diol #, Q4596897, SR-01000076000-1, 2-Methoxyestradiol Solution in Acetonitrile, 100ug/mL, BRD-K44408410-001-17-6, BRD-K44408410-001-20-0, (17|A)-2-Methoxyestra-1,3,5(10)-triene-3,17-diol, (17b)-2-Methoxyestra-1,3,5(10)-triene-3,17-diol, 17beta-2-methoxyestra-1,3,5(10)-triene-3,17-diol, (17|_)-2-Methoxyestra-1,3,5(10)-triene-3,17-diol, Estra-1,3,5(10)-triene-3,17.beta.-diol, 2-methoxy-, estra-1(10),2,4-triene-3,17-diol, 2-methoxy-, (17beta)-, (14beta,17beta)-2-methoxyestra-1(10),2,4-triene-3,17-diol, (17.BETA.)-2-METHOXYESTRA-1,3,5(10)-TRIENE-3,17-DIOL, B3C40B85-1733-48FE-8418-A39011910D19, Estra-1,3,5(10)-triene-3,17-diol, 2-methoxy-, (17.beta.)-, 2-Methoxyestradiol; (8R,9S,13S,14S,17S)-2-methoxy-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthrene-3,17-diol
Theoretical properties:
molecular_formula: C19H26O3
molecular_weight: 302.4 g/mol
exact_mass: 302.18819469 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 2
hydrogen_bond_acceptor_count: 3
rotatable_bond_count: 1
heavy_atom_count: 22
topological_polar_surface_area: 49.7 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
melting_point: 189 - 190 °C
Descriptions:
pubchem: 2-methoxy-17beta-estradiol is a 17beta-hydroxy steroid, being 17beta-estradiol methoxylated at C-2. It has a role as a metabolite, an antineoplastic agent, an angiogenesis modulating agent, an antimitotic, a mouse metabolite and a human metabolite. It is a 17beta-hydroxy steroid and a 3-hydroxy steroid. It is functionally related to a 17beta-estradiol.
chebi: A 17β-hydroxy steroid, being 17β-estradiol methoxylated at C-2.
chembl: 2-METHOXYESTRADIOL is a small molecule listed in the ChEMBL database and has reached clinical trial phase 2.0.
wikipedia: 2-Methoxyestradiol (2-ME2, 2-MeO-E2) is a natural metabolite of estradiol and 2-hydroxyestradiol (2-OHE2). It is specifically the 2-methyl ether of 2-hydroxyestradiol. 2-Methoxyestradiol prevents the formation of new blood vessels that tumors need in order to grow (angiogenesis), hence it is an angiogenesis inhibitor. It also acts as a vasodilator and induces apoptosis in some cancer cell lines. 2-Methoxyestradiol is derived from estradiol, although it interacts poorly with the estrogen receptors (2,000-fold lower activational potency relative to estradiol). However, it retains activity as a high-affinity agonist of the G protein-coupled estrogen receptor (GPER) (10 nM, relative to 3–6 nM for estradiol). It can also be used to treat alveolar echinococcosis when combined with albendazole.