(4aS,4bR,5S,6aS,6bR,8R,9aR)-6b-Ethylsulfanyl-4b-fluoro-5-hydroxy-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: ALA143729

Chembl Id: CHEMBL143729

PubChem CID: 44363293

Max Phase: Preclinical

Molecular Formula: C25H35FO4S

Molecular Weight: 450.62

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(SCC)O1

Standard InChI:  InChI=1S/C25H35FO4S/c1-5-7-21-29-20-13-18-17-9-8-15-12-16(27)10-11-22(15,3)24(17,26)19(28)14-23(18,4)25(20,30-21)31-6-2/h10-12,17-21,28H,5-9,13-14H2,1-4H3/t17?,18?,19-,20+,21+,22-,23-,24-,25-/m0/s1

Standard InChI Key:  UPGFSDYCNLVAHR-MYBFCEEUSA-N

Alternative Forms

1. Parent:

   

   ALA143729

   (4R,6R,8R,9S,11S,12R,13S)-8-ethylsulfanyl-12-fluoro-11-hydroxy-9,13-dimethyl-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: 450.62

Molecular Weight (Monoisotopic): 450.2240

AlogP: 4.96

#Rotatable Bonds: 4

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: 13.64

CX Basic pKa: ┄

CX LogP: 5.05

CX LogD: 5.05

Aromatic Rings: ┄

Heavy Atoms: 31

QED Weighted: 0.66

Np Likeness Score: 1.93

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