(4aS,4bR,5S,6aS,6bR,8R,9aR,12S)-4b,12-Difluoro-5-hydroxy-4a,6a-dimethyl-6b-methylsulfanyl-8-propyl-4a,4b,5,6,6a,6b,9a,10,10a,10b,11,12-dodecahydro-7,9-dioxa-pentaleno[2,1-a]phenanthren-2-one

ID: ALA342304

Chembl Id: CHEMBL342304

PubChem CID: 44363419

Max Phase: Preclinical

Molecular Formula: C24H32F2O4S

Molecular Weight: 454.58

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCC[C@@H]1O[C@@H]2CC3C4C[C@H](F)C5=CC(=O)C=C[C@]5(C)[C@@]4(F)[C@@H](O)C[C@]3(C)[C@]2(SC)O1

Standard InChI:  InChI=1S/C24H32F2O4S/c1-5-6-20-29-19-11-14-15-10-17(25)16-9-13(27)7-8-21(16,2)23(15,26)18(28)12-22(14,3)24(19,30-20)31-4/h7-9,14-15,17-20,28H,5-6,10-12H2,1-4H3/t14?,15?,17-,18-,19+,20+,21-,22-,23-,24-/m0/s1

Standard InChI Key:  BWYBHULDGDXZAO-AUXVOCDASA-N

Alternative Forms

1. Parent:

   

   ALA342304

   (4R,6R,8R,9S,11S,12R,13S,19S)-12,19-difluoro-11-hydroxy-9,13-dimethyl-8-methylsulfanyl-6-propyl-5,7-dioxapentacyclo[10.8.0.02,9.04,8.013,18]icosa-14,17-dien-16-one

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: 454.58

Molecular Weight (Monoisotopic): 454.1989

AlogP: 4.52

#Rotatable Bonds: 3

Polar Surface Area: 55.76

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.61

CX Basic pKa: ┄

CX LogP: 4.46

CX LogD: 4.46

Aromatic Rings: ┄

Heavy Atoms: 31

QED Weighted: 0.68

Np Likeness Score: 1.80

References

1. Ashton MJ, Lawrence C, Karlsson JA, Stuttle KA, Newton CG, Vacher BY, Webber S, Withnall MJ..  (1996)  Anti-inflammatory 17beta-thioalkyl-16alpha,17alpha-ketal and -acetal androstanes: a new class of airway selective steroids for the treatment of asthma.,  39  (25): [PMID:8960547] [10.1021/jm9604639]

Source

Source(1):

• Scientific Literature