(S)-3-(5-bromoindolin-1-yl)-N-(3-chloro-4-cyanophenyl)-2-hydroxy-2-methylpropanamide

ID: ALA4449952

PubChem CID: 122640134

Max Phase: Preclinical

Molecular Formula: C19H17BrClN3O2

Molecular Weight: 434.72

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  C[C@](O)(CN1CCc2cc(Br)ccc21)C(=O)Nc1ccc(C#N)c(Cl)c1

Standard InChI:  InChI=1S/C19H17BrClN3O2/c1-19(26,11-24-7-6-12-8-14(20)3-5-17(12)24)18(25)23-15-4-2-13(10-22)16(21)9-15/h2-5,8-9,26H,6-7,11H2,1H3,(H,23,25)/t19-/m0/s1

Standard InChI Key:  PYSZYNJVLIZJGH-IBGZPJMESA-N

Molfile:  

 
     RDKit          2D

 26 28  0  0  0  0  0  0  0  0999 V2000
   27.9661  -20.1656    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.4318  -20.5866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.4306  -21.4061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.1387  -21.8151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.8483  -21.4056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.8455  -20.5830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.1369  -20.1777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.5517  -20.1717    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   27.2609  -20.5776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.2640  -21.3948    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.6763  -20.5723    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.3826  -20.1612    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   23.7226  -21.8142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.0146  -22.2222    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   27.5534  -19.4558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.3706  -19.4558    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   30.2646  -19.1712    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.4659  -19.3440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.6757  -19.8774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.1312  -20.4855    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.3858  -21.2590    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.1846  -21.4257    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.7283  -20.8127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.4708  -20.0415    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.1385  -22.6323    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   32.5290  -20.9764    0.0000 Br  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
 23 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4449952

   ---

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: 434.72

Molecular Weight (Monoisotopic): 433.0193

AlogP: 3.73

#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: 1.63

CX LogP: 4.22

CX LogD: 4.22

Aromatic Rings: 2

Heavy Atoms: 26

QED Weighted: 0.77

Np Likeness Score: -1.60

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