trans-4-(2-(2-Fluorophenyl)acetamido)-N-(4-methoxycyclohexyl)-1Hpyrazole-3-carboxamide

ID: ALA3335121

Max Phase: Preclinical

Molecular Formula: C19H23FN4O3

Molecular Weight: 374.42

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CO[C@H]1CC[C@H](NC(=O)c2n[nH]cc2NC(=O)Cc2ccccc2F)CC1

Standard InChI:  InChI=1S/C19H23FN4O3/c1-27-14-8-6-13(7-9-14)22-19(26)18-16(11-21-24-18)23-17(25)10-12-4-2-3-5-15(12)20/h2-5,11,13-14H,6-10H2,1H3,(H,21,24)(H,22,26)(H,23,25)/t13-,14-

Standard InChI Key:  IZJDKDDRAYOTGH-HDJSIYSDSA-N

Molfile:  

     RDKit          2D

 27 29  0  0  0  0  0  0  0  0999 V2000
    5.0599   -7.3057    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7404   -7.7723    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.3956   -7.2709    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.1192   -6.4908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2952   -6.5162    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8746   -5.8066    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.5340   -5.7776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3590   -5.7805    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.1239   -5.0619    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7739   -5.0673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6002   -5.0740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0149   -4.3650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6084   -3.6466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7824   -3.6419    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3631   -4.3555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0259   -2.9351    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.8509   -2.9410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0496   -5.8155    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6295   -5.1055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6447   -6.5343    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8045   -5.1143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3873   -4.4033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5631   -4.4118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1575   -5.1312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5821   -5.8436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4049   -5.8316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8280   -6.5398    0.0000 F   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  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 21  1  0
 26 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3335121

   ---

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: 374.42

Molecular Weight (Monoisotopic): 374.1754

AlogP: 2.42

#Rotatable Bonds: 6

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: 10.84

CX Basic pKa: 0.01

CX LogP: 2.66

CX LogD: 2.66

Aromatic Rings: 2

Heavy Atoms: 27

QED Weighted: 0.72

Np Likeness Score: -1.74

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