(S)-N-(3-chloro-4-cyanophenyl)-3-(4-fluoroindolin-1-yl)-2-hydroxy-2-methylpropanamide

ID: ALA4527241

PubChem CID: 122640139

Max Phase: Preclinical

Molecular Formula: C19H17ClFN3O2

Molecular Weight: 373.81

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  C[C@](O)(CN1CCc2c(F)cccc21)C(=O)Nc1ccc(C#N)c(Cl)c1

Standard InChI:  InChI=1S/C19H17ClFN3O2/c1-19(26,11-24-8-7-14-16(21)3-2-4-17(14)24)18(25)23-13-6-5-12(10-22)15(20)9-13/h2-6,9,26H,7-8,11H2,1H3,(H,23,25)/t19-/m0/s1

Standard InChI Key:  BOONXORHRXYEMO-IBGZPJMESA-N

Molfile:  

 
     RDKit          2D

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    6.5747  -20.0996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0403  -20.5205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0392  -21.3401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7472  -21.7490    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4569  -21.3396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4541  -20.5169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7455  -20.1117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1602  -20.1057    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.8695  -20.5116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8726  -21.3288    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2849  -20.5063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9911  -20.0952    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3312  -21.7481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6231  -22.1562    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.1620  -19.3897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9791  -19.3897    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.8732  -19.1051    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0745  -19.2780    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2843  -19.8114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7397  -20.4194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9944  -21.1930    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7932  -21.3597    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3369  -20.7467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0794  -19.9755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7471  -22.5662    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   10.6219  -19.3644    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  2  1  0
  6  8  1  0
  8  9  1  0
  9  1  1  0
  9 10  2  0
  1 11  1  0
 11 12  1  0
  3 13  1  0
 13 14  3  0
  1 15  1  0
  1 16  1  1
 12 20  1  0
 19 17  1  0
 17 18  1  0
 18 12  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 19  1  0
  4 25  1  0
 24 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4527241

   ---

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: 373.81

Molecular Weight (Monoisotopic): 373.0993

AlogP: 3.10

#Rotatable Bonds: 4

Polar Surface Area: 76.36

Molecular Species: NEUTRAL

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.14

CX Basic pKa: 0.42

CX LogP: 3.59

CX LogD: 3.59

Aromatic Rings: 2

Heavy Atoms: 26

QED Weighted: 0.86

Np Likeness Score: -1.66

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