(4aS,4bR,5S,6aS,6bR,8R,9aR)-4b-Fluoro-5-hydroxy-6b-isopropylsulfanyl-4a,6a-dimethyl-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: ALA146781

Chembl Id: CHEMBL146781

PubChem CID: 44363382

Max Phase: Preclinical

Molecular Formula: C26H37FO4S

Molecular Weight: 464.64

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(SC(C)C)O1

Standard InChI:  InChI=1S/C26H37FO4S/c1-6-7-22-30-21-13-19-18-9-8-16-12-17(28)10-11-23(16,4)25(18,27)20(29)14-24(19,5)26(21,31-22)32-15(2)3/h10-12,15,18-22,29H,6-9,13-14H2,1-5H3/t18?,19?,20-,21+,22+,23-,24-,25-,26-/m0/s1

Standard InChI Key:  DUHMEXGGVGTKKD-NFRRBDOJSA-N

Alternative Forms

1. Parent:

   

   ALA146781

   (4R,6R,8R,9S,11S,12R,13S)-12-fluoro-11-hydroxy-9,13-dimethyl-8-propan-2-ylsulfanyl-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: 464.64

Molecular Weight (Monoisotopic): 464.2397

AlogP: 5.35

#Rotatable Bonds: 4

Polar Surface Area: 55.76

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 13.64

CX Basic pKa: ┄

CX LogP: 5.37

CX LogD: 5.37

Aromatic Rings: ┄

Heavy Atoms: 32

QED Weighted: 0.61

Np Likeness Score: 1.81

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