(4aS,4bR,5S,6aS,6bR,9aR)-4b-Fluoro-5-hydroxy-4a,6a,8,8-tetramethyl-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: ALA435878

Chembl Id: CHEMBL435878

PubChem CID: 44363544

Max Phase: Preclinical

Molecular Formula: C27H32FNO4S

Molecular Weight: 485.62

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC1(C)O[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/C27H32FNO4S/c1-23(2)32-21-14-19-18-9-8-16-13-17(30)10-11-24(16,3)26(18,28)20(31)15-25(19,4)27(21,33-23)34-22-7-5-6-12-29-22/h5-7,10-13,18-21,31H,8-9,14-15H2,1-4H3/t18?,19?,20-,21+,24-,25-,26-,27-/m0/s1

Standard InChI Key:  GEZGJHOQDFAPKQ-BBECVQEJSA-N

Alternative Forms

1. Parent:

   

   ALA435878

   (4R,8R,9S,11S,12R,13S)-12-fluoro-11-hydroxy-6,6,9,13-tetramethyl-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: 485.62

Molecular Weight (Monoisotopic): 485.2036

AlogP: 5.00

#Rotatable Bonds: 2

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: 4.72

CX LogD: 4.72

Aromatic Rings: 1

Heavy Atoms: 34

QED Weighted: 0.64

Np Likeness Score: 1.44

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