2-(6-methyl-5,7-dioxo-2,3,4,5,6,7-hexahydro-1H-pyrrolo[3,4-b]pyridin-1-yl)-N-(4-(thiazol-2-yl)phenyl)acetamide

ID: ALA4094309

PubChem CID: 118174156

Max Phase: Preclinical

Molecular Formula: C19H18N4O3S

Molecular Weight: 382.45

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CN1C(=O)C2=C(C1=O)N(CC(=O)Nc1ccc(-c3nccs3)cc1)CCC2

Standard InChI:  InChI=1S/C19H18N4O3S/c1-22-18(25)14-3-2-9-23(16(14)19(22)26)11-15(24)21-13-6-4-12(5-7-13)17-20-8-10-27-17/h4-8,10H,2-3,9,11H2,1H3,(H,21,24)

Standard InChI Key:  VTOSQZJXSCCBQX-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 27 30  0  0  0  0  0  0  0  0999 V2000
   15.7095   -5.2728    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.7082   -4.4515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4194   -4.0376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4181   -3.2163    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.1277   -4.4492    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.8389   -4.0353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5503   -4.4509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2610   -4.0377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2602   -3.2155    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5427   -2.8082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8349   -3.2196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9721   -2.8014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.7238   -3.1315    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.2688   -2.5185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8581   -1.8078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0552   -1.9843    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   15.7055   -6.9152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4185   -6.5026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4208   -5.6787    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9948   -6.4998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9972   -5.6817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2196   -5.4279    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7350   -6.0892    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.2158   -6.7491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9611   -7.5297    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.9693   -4.6458    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.9137   -6.0869    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
  3  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11  6  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 12  1  0
  9 12  1  0
  1 21  1  0
  1 19  1  0
 20 17  1  0
 17 18  1  0
 18 19  1  0
 20 21  2  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 20  1  0
 24 25  2  0
 22 26  2  0
 23 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4094309

   2-(6-methyl-5,7-dioxo-3,4-dihydro-2H-pyrrolo[3,4-b]pyridin-1-yl)-N-[4-(1,3-thiazol-2-yl)phenyl]acetamide

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: 382.45

Molecular Weight (Monoisotopic): 382.1100

AlogP: 2.10

#Rotatable Bonds: 4

Polar Surface Area: 82.61

Molecular Species: NEUTRAL

HBA: 6

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.06

CX Basic pKa: 2.64

CX LogP: 1.21

CX LogD: 1.21

Aromatic Rings: 2

Heavy Atoms: 27

QED Weighted: 0.82

Np Likeness Score: -1.58

References

1. Ho SY, Alam J, Jeyaraj DA, Wang W, Lin GR, Ang SH, Tan ESW, Lee MA, Ke Z, Madan B, Virshup DM, Ding LJ, Manoharan V, Chew YS, Low CB, Pendharkar V, Sangthongpitag K, Hill J, Keller TH, Poulsen A..  (2017)  Scaffold Hopping and Optimization of Maleimide Based Porcupine Inhibitors.,  60  (15): [PMID:28671458] [10.1021/acs.jmedchem.7b00662]

2. Liu Z, Wang P, Wold EA, Song Q, Zhao C, Wang C, Zhou J..  (2021)  Small-Molecule Inhibitors Targeting the Canonical WNT Signaling Pathway for the Treatment of Cancer.,  64  (8.0): [PMID:33822624] [10.1021/acs.jmedchem.0c01799]

Source

Source(1):

• Scientific Literature