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

ID: ALA1627636

Chembl Id: CHEMBL1627636

PubChem CID: 10522696

Max Phase: Preclinical

Molecular Formula: C21H27ClO3

Molecular Weight: 362.90

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C21H27ClO3/c1-20-12-18(25-2)19-15-6-4-14(23)11-13(15)3-5-16(19)17(20)7-8-21(20,24)9-10-22/h4,6,9-11,16-19,23-24H,3,5,7-8,12H2,1-2H3/b10-9-/t16-,17-,18-,19+,20-,21+/m0/s1

Standard InChI Key:  WYSGEJWYPOTZIV-JFWLHBMXSA-N

Alternative Forms

1. Parent:

   

   ALA1627636

   (8S,9S,11S,13S,14S,17R)-17-[(Z)-2-chloroethenyl]-11-methoxy-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: 362.90

Molecular Weight (Monoisotopic): 362.1649

AlogP: 4.36

#Rotatable Bonds: 2

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: 4.05

CX LogD: 4.05

Aromatic Rings: 1

Heavy Atoms: 25

QED Weighted: 0.82

Np Likeness Score: 1.92

References

1. 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