(9R,10S,11S,13S,17R)-17-Ethylsulfanyl-9-fluoro-11-hydroxy-10,13-dimethyl-17-methylsulfanyl-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-cyclopenta[a]phenanthren-3-one

ID: ALA1908322

Chembl Id: CHEMBL1908322

Cas Number: 85197-77-9

PubChem CID: 6917939

Max Phase: Phase

Molecular Formula: C22H31FO2S2

Molecular Weight: 410.62

Molecule Type: Small molecule

Names and Identifiers

Synonyms: SQ 27,239 | SQ-27239 | TIPREDANE|85197-77-9|SQ-27239|SQ 27,239|Tipredane (USAN)|169D68E13P|TIPREDANE [USAN]|Tipredanum|Tipredano|Tipredanum [Latin]|Tipredano [Spanish]|Tipredane [USAN:INN:BAN]|UNII-169D68E13P|TIPREDANE [INN]|SCHEMBL9569097|CHEMBL1908322|CHEBI:175291|DTXSID101318657|BDBM50369181|9-Fluoro-11beta-hydroxyandrosta-1,4-diene-3,17-dione (17R)-17-(ethyl methyl mercaptole)|(11-beta,17-alpha)-17-(Ethylthio)-9-fluoro-11-hydroxy-17-(methylthio)androsta-1,4-dien-3-one|(8S,9R,10S,11S,13S,14S,Show More⌵

Canonical SMILES:  CCS[C@]1(SC)CC[C@H]2[C@@H]3CCC4=CC(=O)C=C[C@]4(C)[C@@]3(F)[C@@H](O)C[C@@]21C

Standard InChI:  InChI=1S/C22H31FO2S2/c1-5-27-21(26-4)11-9-16-17-7-6-14-12-15(24)8-10-19(14,2)22(17,23)18(25)13-20(16,21)3/h8,10,12,16-18,25H,5-7,9,11,13H2,1-4H3/t16-,17-,18-,19-,20-,21+,22-/m0/s1

Standard InChI Key:  DXEXNWDGDYUITL-FXSSSKFRSA-N

Alternative Forms

1. Parent:

   

   ALA1908322

   TIPREDANE

Molecule Features

Natural Product: Yes

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: Yes

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 410.62

Molecular Weight (Monoisotopic): 410.1750

AlogP: 5.17

#Rotatable Bonds: 3

Polar Surface Area: 37.30

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 2

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 13.64

CX Basic pKa: ┄

CX LogP: 4.79

CX LogD: 4.79

Aromatic Rings: ┄

Heavy Atoms: 27

QED Weighted: 0.65

Np Likeness Score: 1.87

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]

2. USP Dictionary of USAN and International Names (2010 edition) and USAN registrations 2007-date, 

3. Warner DJ, Chen H, Cantin LD, Kenna JG, Stahl S, Walker CL, Noeske T..  (2012)  Mitigating the inhibition of human bile salt export pump by drugs: opportunities provided by physicochemical property modulation, in silico modeling, and structural modification.,  40  (12): [PMID:22961681] [10.1124/dmd.112.047068]

Source

Source(2):

• Scientific Literature
• USP Dictionary of USAN and International Drug Names