2-(1,3-Dimethyl-2,6-dioxo-1,2,3,6-tetrahydro-7H-purin-7-yl)-N-(4-(thiazol-2-yl)phenyl)acetamide

ID: ALA4066798

Cas Number: 877950-06-6

PubChem CID: 9114840

Max Phase: Preclinical

Molecular Formula: C18H16N6O3S

Molecular Weight: 396.43

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cn1c(=O)c2c(ncn2CC(=O)Nc2ccc(-c3nccs3)cc2)n(C)c1=O

Standard InChI:  InChI=1S/C18H16N6O3S/c1-22-15-14(17(26)23(2)18(22)27)24(10-20-15)9-13(25)21-12-5-3-11(4-6-12)16-19-7-8-28-16/h3-8,10H,9H2,1-2H3,(H,21,25)

Standard InChI Key:  XEXMFSSSINTTTQ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 28 31  0  0  0  0  0  0  0  0999 V2000
    2.9881  -13.8757    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9881  -14.6929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6934  -15.0974    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6934  -13.4630    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3987  -13.8757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4032  -14.6939    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1827  -14.9425    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.6601  -14.2779    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1754  -13.6187    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.4236  -12.8401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2220  -12.6658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4702  -11.8872    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7722  -13.2700    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.5706  -13.0957    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6934  -12.6458    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6918  -15.9146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2792  -13.4692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2810  -15.1026    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1185  -13.7034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9162  -13.5296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1651  -12.7503    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6102  -12.1447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8145  -12.3217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9656  -12.5721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5766  -13.1146    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.2815  -12.7012    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1061  -11.9030    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2929  -11.8233    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  1  4  1  0
  2  3  1  0
  3  6  1  0
  5  4  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9  5  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  1  0
  4 15  2  0
  3 16  1  0
  1 17  1  0
  2 18  2  0
 14 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 14  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 28 24  1  0
 21 24  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4066798

   2-(1,3-dimethyl-2,6-dioxo-2,3,6,7-tetrahydro-1H-purin-7-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: 396.43

Molecular Weight (Monoisotopic): 396.1005

AlogP: 1.20

#Rotatable Bonds: 4

Polar Surface Area: 103.81

Molecular Species: NEUTRAL

HBA: 9

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.93

CX Basic pKa: 2.64

CX LogP: 1.05

CX LogD: 1.05

Aromatic Rings: 4

Heavy Atoms: 28

QED Weighted: 0.56

Np Likeness Score: -2.06

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