4-benzamido-N-((trans)-4-methoxycyclohexyl)-1H-pyrazole-3-carboxamide

ID: ALA3335124

Max Phase: Preclinical

Molecular Formula: C18H22N4O3

Molecular Weight: 342.40

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CO[C@H]1CC[C@H](NC(=O)c2n[nH]cc2NC(=O)c2ccccc2)CC1

Standard InChI:  InChI=1S/C18H22N4O3/c1-25-14-9-7-13(8-10-14)20-18(24)16-15(11-19-22-16)21-17(23)12-5-3-2-4-6-12/h2-6,11,13-14H,7-10H2,1H3,(H,19,22)(H,20,24)(H,21,23)/t13-,14-

Standard InChI Key:  VPYBJHYVRIXQPO-HDJSIYSDSA-N

Molfile:  

     RDKit          2D

 25 27  0  0  0  0  0  0  0  0999 V2000
    8.7101  -13.8601    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3904  -14.3266    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.0457  -13.8252    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.7692  -13.0451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9452  -13.0705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5246  -12.3609    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.1842  -12.3320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0091  -12.3347    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.7740  -11.6161    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.4240  -11.6216    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2503  -11.6282    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6651  -10.9192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2584  -10.2009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4325  -10.1963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0131  -10.9098    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6760   -9.4895    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.5010   -9.4953    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6997  -12.3698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2795  -11.6597    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2949  -13.0887    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6869  -10.9425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2675  -10.2330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4417  -10.2414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0370  -10.9653    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4588  -11.6719    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  2  0
  4  5  1  0
  5  1  2  0
  5  6  1  0
  4  7  1  0
  7  8  1  0
  7  9  2  0
 10  8  1  1
 10 11  1  0
 10 15  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 13 16  1  6
 16 17  1  0
  6 18  1  0
 18 19  1  0
 18 20  2  0
 19 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 19  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3335124

   ---

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: 342.40

Molecular Weight (Monoisotopic): 342.1692

AlogP: 2.35

#Rotatable Bonds: 5

Polar Surface Area: 96.11

Molecular Species: NEUTRAL

HBA: 4

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 10.77

CX Basic pKa: 0.01

CX LogP: 2.54

CX LogD: 2.53

Aromatic Rings: 2

Heavy Atoms: 25

QED Weighted: 0.78

Np Likeness Score: -1.25

References

1. Urich R, Grimaldi R, Luksch T, Frearson JA, Brenk R, Wyatt PG..  (2014)  The design and synthesis of potent and selective inhibitors of Trypanosoma brucei glycogen synthase kinase 3 for the treatment of human african trypanosomiasis.,  57  (18): [PMID:25198388] [10.1021/jm500239b]

Source

Source(1):

• Scientific Literature