(S)-N-(3-(Naphthalen-1-yl)-1-oxo-1-(pyridin-4-ylamino)propan-2-yl)cyclohexanecarboxamide

ID: ALA2431639

PubChem CID: 72703689

Max Phase: Preclinical

Molecular Formula: C25H27N3O2

Molecular Weight: 401.51

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(N[C@@H](Cc1cccc2ccccc12)C(=O)Nc1ccncc1)C1CCCCC1

Standard InChI:  InChI=1S/C25H27N3O2/c29-24(19-8-2-1-3-9-19)28-23(25(30)27-21-13-15-26-16-14-21)17-20-11-6-10-18-7-4-5-12-22(18)20/h4-7,10-16,19,23H,1-3,8-9,17H2,(H,28,29)(H,26,27,30)/t23-/m0/s1

Standard InChI Key:  QQWJNBNFBWBZBF-QHCPKHFHSA-N

Molfile:  

     RDKit          2D

 30 33  0  0  0  0  0  0  0  0999 V2000
    6.9470  -10.5600    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2326  -10.1475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5181  -10.5600    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5181  -11.3850    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2326  -11.7975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9470  -11.3850    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6615  -10.1475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3760  -10.5600    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6615   -9.3225    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.0905   -9.3225    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3760   -8.9100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3760   -8.0850    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8049   -8.9100    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.2339  -10.5600    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5194  -10.1475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5194   -9.3225    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2339   -8.9100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9483   -9.3225    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9483  -10.1475    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.0905  -10.1475    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6615   -7.6725    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9470   -8.0850    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2326   -7.6725    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2326   -6.8475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9470   -6.4350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9470   -5.6100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6615   -5.1975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3760   -5.6100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3760   -6.4350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6615   -6.8475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  1  6  1  0
  7  8  2  0
  7  9  1  0
  1  7  1  0
 10 11  1  0
 11 12  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 14 19  2  0
 13 16  1  0
 10 13  1  0
 10 20  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 28 29  2  0
 29 30  1  0
 21 30  2  0
 25 30  1  0
 12 21  1  0
 11  9  1  1
M  END

Alternative Forms

1. Parent:

   

   ALA2431639

   N-[(2S)-3-naphthalen-1-yl-1-oxo-1-(pyridin-4-ylamino)propan-2-yl]cyclohexanecarboxamide

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 401.51

Molecular Weight (Monoisotopic): 401.2103

AlogP: 4.48

#Rotatable Bonds: 6

Polar Surface Area: 71.09

Molecular Species: NEUTRAL

HBA: 3

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.41

CX Basic pKa: 5.63

CX LogP: 4.22

CX LogD: 4.21

Aromatic Rings: 3

Heavy Atoms: 30

QED Weighted: 0.64

Np Likeness Score: -1.07

References

1. Choi JY, Calvet CM, Gunatilleke SS, Ruiz C, Cameron MD, McKerrow JH, Podust LM, Roush WR..  (2013)  Rational development of 4-aminopyridyl-based inhibitors targeting Trypanosoma cruzi CYP51 as anti-chagas agents.,  56  (19): [PMID:24079662] [10.1021/jm401067s]

Source

Source(1):

• Scientific Literature