(S)-N-(3-chloro-4-cyanophenyl)-3-(5-fluoro-6-phenyl-1H-indol-1-yl)-2-hydroxy-2-methylpropanamide

ID: ALA4447959

PubChem CID: 122640109

Max Phase: Preclinical

Molecular Formula: C25H19ClFN3O2

Molecular Weight: 447.90

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  C[C@](O)(Cn1ccc2cc(F)c(-c3ccccc3)cc21)C(=O)Nc1ccc(C#N)c(Cl)c1

Standard InChI:  InChI=1S/C25H19ClFN3O2/c1-25(32,24(31)29-19-8-7-18(14-28)21(26)12-19)15-30-10-9-17-11-22(27)20(13-23(17)30)16-5-3-2-4-6-16/h2-13,32H,15H2,1H3,(H,29,31)/t25-/m0/s1

Standard InChI Key:  SPLRKZJEQXTCAM-VWLOTQADSA-N

Molfile:  

 
     RDKit          2D

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   12.6816   -8.8983    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   13.3885  -10.1268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   13.3867   -8.4894    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8015   -8.4834    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.5107   -8.8893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5138   -9.7065    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   17.6323   -8.4729    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.9724  -10.1258    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2643  -10.5339    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.8032   -7.7674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6203   -7.7674    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   18.3809   -8.7972    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6356   -9.5707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4344   -9.7374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9781   -9.1244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7206   -8.3532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3883  -10.9440    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   20.7787   -9.2881    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   19.6913  -10.5132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1457  -11.1215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4020  -11.8966    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2030  -12.0627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.7472  -11.4474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4881  -10.6747    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  1 15  1  0
  1 16  1  1
 12 20  1  0
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 22 23  1  0
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  4 25  1  0
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 29 30  2  0
 30 31  1  0
 31 32  2  0
 32 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4447959

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 447.90

Molecular Weight (Monoisotopic): 447.1150

AlogP: 5.36

#Rotatable Bonds: 5

Polar Surface Area: 78.05

Molecular Species: NEUTRAL

HBA: 4

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 12.07

CX Basic pKa: ┄

CX LogP: 5.41

CX LogD: 5.41

Aromatic Rings: 4

Heavy Atoms: 32

QED Weighted: 0.43

Np Likeness Score: -1.34

References

1. Hwang DJ, He Y, Ponnusamy S, Mohler ML, Thiyagarajan T, McEwan IJ, Narayanan R, Miller DD..  (2019)  New Generation of Selective Androgen Receptor Degraders: Our Initial Design, Synthesis, and Biological Evaluation of New Compounds with Enzalutamide-Resistant Prostate Cancer Activity.,  62  (2): [PMID:30525603] [10.1021/acs.jmedchem.8b00973]

Source

Source(1):

• Scientific Literature