3-Fluoro-5-(((1S,2S)-2-fluoro-1-hydroxy-7-(methylsulfonyl)-2,3-dihydro-1H-inden-4-yl)oxy)benzonitrile

ID: ALA4170809

Chembl Id: CHEMBL4170809

PubChem CID: 117947043

Max Phase: Preclinical

Molecular Formula: C17H13F2NO4S

Molecular Weight: 365.36

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CS(=O)(=O)c1ccc(Oc2cc(F)cc(C#N)c2)c2c1[C@H](O)[C@@H](F)C2

Standard InChI:  InChI=1S/C17H13F2NO4S/c1-25(22,23)15-3-2-14(12-7-13(19)17(21)16(12)15)24-11-5-9(8-20)4-10(18)6-11/h2-6,13,17,21H,7H2,1H3/t13-,17+/m0/s1

Standard InChI Key:  GTHLUQQEKIJSME-SUMWQHHRSA-N

Alternative Forms

1. Parent:

   

   ALA4170809

   3-fluoro-5-[[(1S,2S)-2-fluoro-1-hydroxy-7-methylsulfonyl-2,3-dihydro-1H-inden-4-yl]oxy]benzonitrile

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: 365.36

Molecular Weight (Monoisotopic): 365.0533

AlogP: 2.82

#Rotatable Bonds: 3

Polar Surface Area: 87.39

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.72

CX Basic pKa: ┄

CX LogP: 1.91

CX LogD: 1.91

Aromatic Rings: 2

Heavy Atoms: 25

QED Weighted: 0.90

Np Likeness Score: -0.87

References

1. Wehn PM, Rizzi JP, Dixon DD, Grina JA, Schlachter ST, Wang B, Xu R, Yang H, Du X, Han G, Wang K, Cao Z, Cheng T, Czerwinski RM, Goggin BS, Huang H, Halfmann MM, Maddie MA, Morton EL, Olive SR, Tan H, Xie S, Wong T, Josey JA, Wallace EM..  (2018)  Design and Activity of Specific Hypoxia-Inducible Factor-2α (HIF-2α) Inhibitors for the Treatment of Clear Cell Renal Cell Carcinoma: Discovery of Clinical Candidate ( S)-3-((2,2-Difluoro-1-hydroxy-7-(methylsulfonyl)-2,3-dihydro-1 H-inden-4-yl)oxy)-5-fluorobenzonitrile (PT2385).,  61  (21): [PMID:30289716] [10.1021/acs.jmedchem.8b01196]

2. Xu R, Wang K, Rizzi JP, Huang H, Grina JA, Schlachter ST, Wang B, Wehn PM, Yang H, Dixon DD, Czerwinski RM, Du X, Ged EL, Han G, Tan H, Wong T, Xie S, Josey JA, Wallace EM..  (2019)  3-[(1S,2S,3R)-2,3-Difluoro-1-hydroxy-7-methylsulfonylindan-4-yl]oxy-5-fluorobenzonitrile (PT2977), a Hypoxia-Inducible Factor 2α (HIF-2α) Inhibitor for the Treatment of Clear Cell Renal Cell Carcinoma.,  62  (15): [PMID:31282155] [10.1021/acs.jmedchem.9b00719]

Source

Source(1):

• Scientific Literature