(S)-N-(1-((4-acetylphenyl)amino)-1-oxo-3-phenylpropan-2-yl)-4-(aminomethyl)cyclohexanecarboxamide

ID: ALA5283915

Max Phase: Preclinical

Molecular Formula: C25H31N3O3

Molecular Weight: 421.54

Names and Identifiers

Canonical SMILES:  CC(=O)c1ccc(NC(=O)[C@H](Cc2ccccc2)NC(=O)C2CCC(CN)CC2)cc1

Standard InChI:  InChI=1S/C25H31N3O3/c1-17(29)20-11-13-22(14-12-20)27-25(31)23(15-18-5-3-2-4-6-18)28-24(30)21-9-7-19(16-26)8-10-21/h2-6,11-14,19,21,23H,7-10,15-16,26H2,1H3,(H,27,31)(H,28,30)/t19?,21-,23-/m0/s1

Standard InChI Key:  DLFGZBZOIOZRSV-FLJXZVEISA-N

Molfile:  

 
     RDKit          2D

 31 33  0  0  0  0  0  0  0  0999 V2000
    2.1355   -1.2348    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1355   -0.4098    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8471    0.0006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5560   -0.4095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5560   -1.2311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8489   -1.6412    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2674   -1.6419    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9789   -1.2311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2674   -2.4633    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4241    0.0008    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7128   -0.4098    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7128   -1.2313    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0013    0.0008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0013    0.8223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7128    1.2330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4272    0.8205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1358    1.2351    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1358    2.0525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4226    2.4633    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7128    2.0545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7100   -0.4098    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4214    0.0008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4214    0.8223    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1328   -0.4098    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1328   -1.2315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8444   -1.6424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5560   -1.2315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2675   -1.6423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9789   -1.2315    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5560   -0.4098    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8444    0.0009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  2  2  0
  4  3  1  0
  5  4  2  0
  1  6  2  0
  6  5  1  0
  5  7  1  0
  7  8  1  0
  7  9  2  0
 10  2  1  0
 11 10  1  0
 11 12  2  0
 13 11  1  0
 13 14  1  1
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 15  2  0
 21 13  1  0
 22 21  1  0
 22 23  2  0
 24 22  1  6
 25 24  1  0
 26 25  1  0
 27 26  1  0
 27 28  1  0
 28 29  1  0
 30 27  1  0
 24 31  1  0
 30 31  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA5283915

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type:

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 421.54

Molecular Weight (Monoisotopic): 421.2365

AlogP: 3.32

#Rotatable Bonds: 8

Polar Surface Area: 101.29

Molecular Species: BASE

HBA: 4

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.42

CX Basic pKa: 10.22

CX LogP: 2.82

CX LogD: 0.21

Aromatic Rings: 2

Heavy Atoms: 31

QED Weighted: 0.57

Np Likeness Score: -0.86

References

1. Xie Z, Li Z, Shao Y, Liao C..  (2020)  Discovery and development of plasma kallikrein inhibitors for multiple diseases.,  190  [PMID:32066009] [10.1016/j.ejmech.2020.112137]

Source

Source(1):

• Scientific Literature