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

ID: ALA362396

Chembl Id: CHEMBL362396

Cas Number: 64109-72-4

PubChem CID: 23622130

Max Phase: Preclinical

Molecular Formula: C20H28O2

Molecular Weight: 300.44

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC[C@H]1C[C@]2(C)[C@@H](O)CC[C@H]2[C@@H]2CCc3cc(O)ccc3[C@@H]12

Standard InChI:  InChI=1S/C20H28O2/c1-3-12-11-20(2)17(8-9-18(20)22)16-6-4-13-10-14(21)5-7-15(13)19(12)16/h5,7,10,12,16-19,21-22H,3-4,6,8-9,11H2,1-2H3/t12-,16-,17-,18-,19+,20-/m0/s1

Standard InChI Key:  QUXNMGWLKZIPHL-QCUBTISBSA-N

Alternative Forms

1. Parent:

   

   ALA362396

   11-beta-Ethylestradiol

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: 300.44

Molecular Weight (Monoisotopic): 300.2089

AlogP: 4.25

#Rotatable Bonds: 1

Polar Surface Area: 40.46

Molecular Species: NEUTRAL

HBA: 2

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 2

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 10.31

CX Basic pKa: ┄

CX LogP: 4.48

CX LogD: 4.48

Aromatic Rings: 1

Heavy Atoms: 22

QED Weighted: 0.81

Np Likeness Score: 2.12

References

1. Napolitano E, Fiaschi R, Carlson KE, Katzenellenbogen JA..  (1995)  11 beta-substituted estradiol derivatives. 2. Potential carbon-11- and iodine-labeled probes for the estrogen receptor.,  38  (14): [PMID:7629815] [10.1021/jm00014a028]

2. Tedesco R, Katzenellenbogen JA, Napolitano E.  (1997)  7,11-Disubstituted estrogens: Probes for the shape of the ligand binding pocket in the estrogen receptor,  7  (22): [10.1016/S0960-894X(97)10099-3]

3. 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]

4. Hanson RN, Napolitano E, Fiaschi R..  (1990)  Synthesis and estrogen receptor binding of novel 11 beta-substituted estra-1,3,5(10)-triene-3,17 beta-diols.,  33  (12): [PMID:2258901] [10.1021/jm00174a010]

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

6. 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]

7. 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]

8. Poupaert JH, Lambert DM, Vamecq J, Abul-Hajj YJ.  (1995)  Molecular modeling studies on 11-aminoethoxyphenyl and 7-aminoethoxyphenyl estradiols. evidence suggesting a common hydrophobic pocket in estrogen receptor,  5  (8): [10.1016/0960-894X(95)00128-G]

Source

Source(1):

• Scientific Literature