N-(4-Cyano-3-(trifluoromethyl)phenyl)-4-(4-cyanophenyl)-2-hydroxy-2-methylbutanamide

ID: ALA4871808

PubChem CID: 164623876

Max Phase: Preclinical

Molecular Formula: C20H16F3N3O2

Molecular Weight: 387.36

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  C[C@](O)(CCc1ccc(C#N)cc1)C(=O)Nc1ccc(C#N)c(C(F)(F)F)c1

Standard InChI:  InChI=1S/C20H16F3N3O2/c1-19(28,9-8-13-2-4-14(11-24)5-3-13)18(27)26-16-7-6-15(12-25)17(10-16)20(21,22)23/h2-7,10,28H,8-9H2,1H3,(H,26,27)/t19-/m0/s1

Standard InChI Key:  JCTPUKOIDARXSK-IBGZPJMESA-N

Molfile:  

 
     RDKit          2D

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    4.1166  -28.8416    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    3.2916  -28.8416    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7041  -29.5560    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    5.7333  -25.6373    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1500  -26.3540    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5623  -25.6349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5819  -26.7790    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5807  -27.6064    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2956  -28.0193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0120  -27.6059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0091  -26.7754    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2938  -26.3662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7221  -26.3602    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.4380  -26.7700    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4412  -27.5950    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8660  -28.0183    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1512  -28.4303    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.8670  -26.7646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5808  -29.2566    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    7.5800  -26.3496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2959  -26.7595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2960  -27.5843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0110  -27.9941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7250  -27.5790    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7194  -26.7498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0038  -26.3436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4415  -27.9880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1559  -28.4005    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  2  1  0
  5  4  1  1
  6  5  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12  7  1  0
 11 13  1  0
 13 14  1  0
 14  5  1  0
 14 15  2  0
  8 16  1  0
 16 17  3  0
  5 18  1  0
  9  2  1  0
  2 19  1  0
 18 20  1  0
 20 21  1  0
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 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 21  1  0
 24 27  1  0
 27 28  3  0
M  END

Alternative Forms

1. Parent:

   

   ALA4871808

   ---

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: 387.36

Molecular Weight (Monoisotopic): 387.1195

AlogP: 3.77

#Rotatable Bonds: 5

Polar Surface Area: 96.91

Molecular Species: NEUTRAL

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.30

CX Basic pKa: ┄

CX LogP: 4.09

CX LogD: 4.09

Aromatic Rings: 2

Heavy Atoms: 28

QED Weighted: 0.82

Np Likeness Score: -1.12

References

1. He Y, Hwang DJ, Ponnusamy S, Thiyagarajan T, Mohler ML, Narayanan R, Miller DD..  (2021)  Exploration and Biological Evaluation of Basic Heteromonocyclic Propanamide Derivatives as SARDs for the Treatment of Enzalutamide-Resistant Prostate Cancer.,  64  (15.0): [PMID:34269581] [10.1021/acs.jmedchem.1c00439]

Source

Source(1):

• Scientific Literature