17-(2-Chloro-vinyl)-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthrene-3,17-diol

ID: ALA1627811

Chembl Id: CHEMBL1627811

PubChem CID: 53323832

Max Phase: Preclinical

Molecular Formula: C20H25ClO2

Molecular Weight: 332.87

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C[C@]12CC[C@@H]3c4ccc(O)cc4CC[C@H]3[C@@H]1CC[C@@]2(O)/C=C/Cl

Standard InChI:  InChI=1S/C20H25ClO2/c1-19-8-6-16-15-5-3-14(22)12-13(15)2-4-17(16)18(19)7-9-20(19,23)10-11-21/h3,5,10-12,16-18,22-23H,2,4,6-9H2,1H3/b11-10+/t16-,17-,18+,19+,20-/m1/s1

Standard InChI Key:  FXTAPPARPABPIO-XTJNFZKPSA-N

Alternative Forms

1. Parent:

   

   ALA1627811

   (8R,9S,13S,14S,17R)-17-[(E)-2-chloroethenyl]-13-methyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthrene-3,17-diol

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: 332.87

Molecular Weight (Monoisotopic): 332.1543

AlogP: 4.73

#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: 10.33

CX Basic pKa: ┄

CX LogP: 4.72

CX LogD: 4.72

Aromatic Rings: 1

Heavy Atoms: 23

QED Weighted: 0.78

Np Likeness Score: 1.80

References

1. Napolitano E, Fiaschi R, Hanson RN..  (1991)  Structure-activity relationships of estrogenic ligands: synthesis and evaluation of (17 alpha, 20E)- and (17 alpha, 20Z)-21-halo-19-norpregna-1,3,5(10),20-tetraene-3,17 beta-diols.,  34  (9): [PMID:1895295] [10.1021/jm00113a012]

2. Hanson RN, Napolitano E, Fiaschi R..  (1998)  Synthesis and evaluation of 11beta-substituted 21-chloro/iodo-(17alpha,20E/Z)-19-norpregna-1,3,5(10),20-te traene-3, 17beta-diols: high-affinity ligands for the estrogen receptor.,  41  (24): [PMID:9822539] [10.1021/jm9801051]

Source

Source(1):

• Scientific Literature