N-[(2-chlorophenyl)methyl]-2-(8-ethoxy-1,3-dimethyl-2,6-dioxo-2,3,6,7-tetrahydro-1H-purin-7-yl)acetamide

ID: ALA4280678

PubChem CID: 145981946

Max Phase: Preclinical

Molecular Formula: C18H20ClN5O4

Molecular Weight: 405.84

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCOc1nc2c(c(=O)n(C)c(=O)n2C)n1CC(=O)NCc1ccccc1Cl

Standard InChI:  InChI=1S/C18H20ClN5O4/c1-4-28-17-21-15-14(16(26)23(3)18(27)22(15)2)24(17)10-13(25)20-9-11-7-5-6-8-12(11)19/h5-8H,4,9-10H2,1-3H3,(H,20,25)

Standard InChI Key:  AXLHWHOGICMUBE-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 28 30  0  0  0  0  0  0  0  0999 V2000
    6.5831  -13.1151    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.0713  -12.4597    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5961  -11.7917    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.8083  -12.8552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8200  -12.0384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1224  -11.6223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4087  -12.0182    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.3970  -12.8350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0990  -13.2557    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.0885  -14.0729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7074  -11.5986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1352  -10.8052    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6831  -13.2327    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8884  -12.4686    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.2893  -13.1808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8550  -11.0166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6557  -10.8533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1975  -11.4650    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9146  -10.0782    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.1064  -13.1897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7153   -9.9148    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9742   -9.1397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7748   -8.9808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0338   -8.2066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4918   -7.5939    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6874   -7.7606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4322   -8.5347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3149   -9.5942    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  4  1  1  0
  1  2  2  0
  2  3  1  0
  3  5  1  0
  4  5  2  0
  4  9  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  7 11  1  0
  6 12  2  0
  8 13  2  0
  2 14  1  0
 14 15  1  0
  3 16  1  0
 16 17  1  0
 17 18  2  0
 17 19  1  0
 15 20  1  0
 19 21  1  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 22  1  0
 23 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4280678

   ---

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: 405.84

Molecular Weight (Monoisotopic): 405.1204

AlogP: 0.80

#Rotatable Bonds: 6

Polar Surface Area: 100.15

Molecular Species: NEUTRAL

HBA: 8

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.51

CX Basic pKa: ┄

CX LogP: 1.56

CX LogD: 1.56

Aromatic Rings: 3

Heavy Atoms: 28

QED Weighted: 0.65

Np Likeness Score: -1.92

References

1. Chłoń-Rzepa G, Ślusarczyk M, Jankowska A, Gawalska A, Bucki A, Kołaczkowski M, Świerczek A, Pociecha K, Wyska E, Zygmunt M, Kazek G, Sałat K, Pawłowski M..  (2018)  Novel amide derivatives of 1,3-dimethyl-2,6-dioxopurin-7-yl-alkylcarboxylic acids as multifunctional TRPA1 antagonists and PDE4/7 inhibitors: A new approach for the treatment of pain.,  158  [PMID:30245393] [10.1016/j.ejmech.2018.09.021]

Source

Source(1):

• Scientific Literature