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

ID: ALA144841

Chembl Id: CHEMBL144841

PubChem CID: 44363434

Max Phase: Preclinical

Molecular Formula: C28H34FNO4S

Molecular Weight: 499.65

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCC[C@@H]1O[C@@H]2CC3C4CCC5=CC(=O)C=C[C@]5(C)[C@@]4(F)[C@@H](O)C[C@]3(C)[C@]2(Sc2ccccn2)O1

Standard InChI:  InChI=1S/C28H34FNO4S/c1-4-7-24-33-22-15-20-19-10-9-17-14-18(31)11-12-25(17,2)27(19,29)21(32)16-26(20,3)28(22,34-24)35-23-8-5-6-13-30-23/h5-6,8,11-14,19-22,24,32H,4,7,9-10,15-16H2,1-3H3/t19?,20?,21-,22+,24+,25-,26-,27-,28-/m0/s1

Standard InChI Key:  VWMIKRRBVKACCN-KHTMAQAHSA-N

Alternative Forms

1. Parent:

   

   ALA144841

   (4R,6R,8R,9S,11S,12R,13S)-12-fluoro-11-hydroxy-9,13-dimethyl-6-propyl-8-pyridin-2-ylsulfanyl-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: 499.65

Molecular Weight (Monoisotopic): 499.2193

AlogP: 5.39

#Rotatable Bonds: 4

Polar Surface Area: 68.65

Molecular Species: NEUTRAL

HBA: 6

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 13.64

CX Basic pKa: 2.95

CX LogP: 5.55

CX LogD: 5.55

Aromatic Rings: 1

Heavy Atoms: 35

QED Weighted: 0.60

Np Likeness Score: 1.40

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