11-Methoxy-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthrene-3,17-diol

ID: ALA368703

Chembl Id: CHEMBL368703

Cas Number: 21507-14-2

PubChem CID: 68568

Max Phase: Preclinical

Molecular Formula: C19H26O3

Molecular Weight: 302.41

Molecule Type: Small molecule

Names and Identifiers

Synonyms: 11Beta-Methoxy Estradiol | 11beta-Methoxyestradiol|R3M9HHJ34D|21507-14-2|CCRIS 7201|11Beta-Methoxy Estradiol|UNII-R3M9HHJ34D|11.BETA.-MEOE2|CHEMBL368703|SCHEMBL6854847|11.BETA.-METHOXYESTRADIOL|RU-2504|11.BETA.-METHOXYESTRA-1,3,5(10)-TRIENE-3,17-DIOL|11.BETA.-METHOXYESTRA-1,3,5(10)-TRIENE-3,17.BETA.-DIOL|ESTRA-1,3,5(10)-TRIENE-3,17.BETA.-DIOL, 11.BETA.-METHOXY-|(11.BETA.,17.BETA.)-11-METHOXYESTRA-1,3,5(10)-TRIENE-3,17-DIOL|ESTRA-1,3,5(10)-TRIENE-3,17-DIOL, 11-METHOXY-, (11.BETA.,17.BETA.)-

Canonical SMILES:  CO[C@H]1C[C@]2(C)[C@@H](O)CC[C@H]2[C@@H]2CCc3cc(O)ccc3[C@H]21

Standard InChI:  InChI=1S/C19H26O3/c1-19-10-16(22-2)18-13-6-4-12(20)9-11(13)3-5-14(18)15(19)7-8-17(19)21/h4,6,9,14-18,20-21H,3,5,7-8,10H2,1-2H3/t14-,15-,16-,17-,18+,19-/m0/s1

Standard InChI Key:  OAHDOJSNKCCHJM-VIUKOLAESA-N

Alternative Forms

1. Parent:

   

   ALA368703

   11beta-Methoxyestradiol

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 302.41

Molecular Weight (Monoisotopic): 302.1882

AlogP: 3.23

#Rotatable Bonds: 1

Polar Surface Area: 49.69

Molecular Species: NEUTRAL

HBA: 3

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 3

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 10.21

CX Basic pKa: ┄

CX LogP: 3.08

CX LogD: 3.08

Aromatic Rings: 1

Heavy Atoms: 22

QED Weighted: 0.84

Np Likeness Score: 2.31

References

1. VanBrocklin HF, Carlson KE, Katzenellenbogen JA, Welch MJ..  (1993)  16 beta-([18F]fluoro)estrogens: systematic investigation of a new series of fluorine-18-labeled estrogens as potential imaging agents for estrogen-receptor-positive breast tumors.,  36  (11): [PMID:7684451] [10.1021/jm00063a012]

2. Pomper MG, VanBrocklin H, Thieme AM, Thomas RD, Kiesewetter DO, Carlson KE, Mathias CJ, Welch MJ, Katzenellenbogen JA..  (1990)  11 beta-methoxy-, 11 beta-ethyl- and 17 alpha-ethynyl-substituted 16 alpha-fluoroestradiols: receptor-based imaging agents with enhanced uptake efficiency and selectivity.,  33  (12): [PMID:1701833] [10.1021/jm00174a009]

3. Spradau TW, Katzenellenbogen JA..  (1998)  Ligands for the estrogen receptor, containing cyclopentadienyltricarbonylrhenium units.,  8  (22): [PMID:9873709] [10.1016/s0960-894x(98)00592-7]

4. Gantchev TG, Ali H, van Lier JE..  (1994)  Quantitative structure-activity relationships/comparative molecular field analysis (QSAR/CoMFA) for receptor-binding properties of halogenated estradiol derivatives.,  37  (24): [PMID:7990116] [10.1021/jm00050a013]

5. Napolitano E, Fiaschi R, Carlson KE, Katzenellenbogen JA..  (1995)  11 beta-Substituted estradiol derivatives, potential high-affinity carbon-11-labeled probes for the estrogen receptor: a structure-affinity relationship study.,  38  (3): [PMID:7853335] [10.1021/jm00003a005]

6. Hanson RN, Hua E, Hendricks JA, Labaree D, Hochberg RB..  (2012)  Synthesis and evaluation of 11β-(4-substituted phenyl) estradiol analogs: transition from estrogen receptor agonists to antagonists.,  20  (12): [PMID:22608920] [10.1016/j.bmc.2012.04.041]

Source

Source(1):

• Scientific Literature