(alfa,16-F-17-alfa-ethynyl-E2)17-Ethynyl-16-fluoro-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthrene-3,17-diol

ID: ALA1627452

Chembl Id: CHEMBL1627452

Cas Number: 92817-14-6

PubChem CID: 67376

Max Phase: Preclinical

Molecular Formula: C20H23FO2

Molecular Weight: 314.40

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C#C[C@]1(O)[C@H](F)C[C@H]2[C@@H]3CCc4cc(O)ccc4[C@H]3CC[C@@]21C

Standard InChI:  InChI=1S/C20H23FO2/c1-3-20(23)18(21)11-17-16-6-4-12-10-13(22)5-7-14(12)15(16)8-9-19(17,20)2/h1,5,7,10,15-18,22-23H,4,6,8-9,11H2,2H3/t15-,16-,17+,18-,19+,20+/m1/s1

Standard InChI Key:  IFDRGXJMFGLUCN-NADOGSGZSA-N

Alternative Forms

1. Parent:

   

   ALA1627452

   17-Ethynyl-16-fluoroestradiol

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: 314.40

Molecular Weight (Monoisotopic): 314.1682

AlogP: 3.56

#Rotatable Bonds: ┄

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: 3.71

CX LogD: 3.71

Aromatic Rings: 1

Heavy Atoms: 23

QED Weighted: 0.72

Np Likeness Score: 1.60

References

1. Liu A, Carlson KE, Katzenellenbogen JA..  (1992)  Synthesis of high affinity fluorine-substituted ligands for the androgen receptor. Potential agents for imaging prostatic cancer by positron emission tomography.,  35  (11): [PMID:1597861] [10.1021/jm00089a024]

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]

Source

Source(1):

• Scientific Literature