(S)-N-(3-chloro-4-cyanophenyl)-3-(5,6-difluoroindolin-1-yl)-2-hydroxy-2-methylpropanamide

ID: ALA4521365

PubChem CID: 122640093

Max Phase: Preclinical

Molecular Formula: C19H16ClF2N3O2

Molecular Weight: 391.81

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  C[C@](O)(CN1CCc2cc(F)c(F)cc21)C(=O)Nc1ccc(C#N)c(Cl)c1

Standard InChI:  InChI=1S/C19H16ClF2N3O2/c1-19(27,18(26)24-13-3-2-12(9-23)14(20)7-13)10-25-5-4-11-6-15(21)16(22)8-17(11)25/h2-3,6-8,27H,4-5,10H2,1H3,(H,24,26)/t19-/m0/s1

Standard InChI Key:  UPTPZDHQUUSVAL-IBGZPJMESA-N

Molfile:  

 
     RDKit          2D

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    6.9420  -25.4237    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4077  -25.8447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4065  -26.6642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1146  -27.0732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8242  -26.6637    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8214  -25.8411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1128  -25.4358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5276  -25.4298    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.2368  -25.8357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2399  -26.6529    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6522  -25.8304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3585  -25.4193    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6985  -27.0722    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9905  -27.4803    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.5293  -24.7138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3465  -24.7138    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2405  -24.4292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4418  -24.6021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6516  -25.1355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1071  -25.7436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3617  -26.5171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1605  -26.6838    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7042  -26.0708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4467  -25.2996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1144  -27.8904    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   10.4174  -27.4596    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   11.5048  -26.2345    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
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  6  7  2  0
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  9  1  1  0
  9 10  2  0
  1 11  1  0
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  3 13  1  0
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  1 15  1  0
  1 16  1  1
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 17 18  1  0
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 20 21  1  0
 21 22  2  0
 22 23  1  0
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 24 19  1  0
  4 25  1  0
 22 26  1  0
 23 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4521365

   ---

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: 391.81

Molecular Weight (Monoisotopic): 391.0899

AlogP: 3.24

#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: ┄

CX LogP: 3.73

CX LogD: 3.73

Aromatic Rings: 2

Heavy Atoms: 27

QED Weighted: 0.84

Np Likeness Score: -1.68

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