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

ID: ALA4483663

PubChem CID: 122640094

Max Phase: Preclinical

Molecular Formula: C19H15ClFN3O2

Molecular Weight: 371.80

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/C19H15ClFN3O2/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/h2-9,26H,11H2,1H3,(H,23,25)/t19-/m0/s1

Standard InChI Key:  MVBCFXQHDXSGME-IBGZPJMESA-N

Molfile:  

 
     RDKit          2D

 26 28  0  0  0  0  0  0  0  0999 V2000
   16.0425   -2.9345    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5082   -3.3554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5071   -4.1749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2151   -4.5839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9248   -4.1745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9219   -3.3518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2133   -2.9465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6281   -2.9405    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.3374   -3.3465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3404   -4.1637    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.7528   -3.3411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4590   -2.9300    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.7990   -4.5830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0910   -4.9910    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.6298   -2.2246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4470   -2.2246    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.3410   -1.9400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5424   -2.1128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7522   -2.6463    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2076   -3.2543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4622   -4.0279    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2610   -4.1945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8048   -3.5816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5472   -2.8104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2149   -5.4011    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   20.0898   -2.1993    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  2  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:

   

   ALA4483663

   ---

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: 371.80

Molecular Weight (Monoisotopic): 371.0837

AlogP: 3.70

#Rotatable Bonds: 4

Polar Surface Area: 78.05

Molecular Species: NEUTRAL

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.07

CX Basic pKa: ┄

CX LogP: 3.77

CX LogD: 3.77

Aromatic Rings: 3

Heavy Atoms: 26

QED Weighted: 0.73

Np Likeness Score: -1.76

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