N-[4-(butan-2-yl)phenyl]-4-(8-butoxy-1,3-dimethyl-2,6-dioxo-2,3,6,7-tetrahydro-1H-purin-7-yl)butanamide

ID: ALA4292772

PubChem CID: 145989417

Max Phase: Preclinical

Molecular Formula: C25H35N5O4

Molecular Weight: 469.59

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCCOc1nc2c(c(=O)n(C)c(=O)n2C)n1CCCC(=O)Nc1ccc(C(C)CC)cc1

Standard InChI:  InChI=1S/C25H35N5O4/c1-6-8-16-34-24-27-22-21(23(32)29(5)25(33)28(22)4)30(24)15-9-10-20(31)26-19-13-11-18(12-14-19)17(3)7-2/h11-14,17H,6-10,15-16H2,1-5H3,(H,26,31)

Standard InChI Key:  AVWJLYSWXDFACL-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 34 36  0  0  0  0  0  0  0  0999 V2000
   30.1124  -21.5347    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   30.6006  -20.8792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.1255  -20.2112    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   29.3377  -21.2747    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.3493  -20.4580    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.6517  -20.0418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.9380  -20.4378    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   27.9263  -21.2545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.6284  -21.6753    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   28.6178  -22.4924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.2368  -20.0182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.6645  -19.2247    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.2124  -21.6523    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   31.4178  -20.8882    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   31.8186  -21.6003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.3844  -19.4361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.1851  -19.2728    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.4440  -18.4977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.2447  -18.3344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.5035  -17.5593    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   32.7865  -18.9461    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   33.3042  -17.3959    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.8410  -18.0086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.6410  -17.8457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.9006  -17.0699    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.3540  -16.4567    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.5560  -16.6227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.6357  -21.6093    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.7011  -16.9055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.2437  -17.5165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.0365  -22.3214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.9589  -16.1301    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.0442  -17.3521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.8537  -22.3304    0.0000 C   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  1  0
 18 19  1  0
 19 20  1  0
 19 21  2  0
 20 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
 15 28  1  0
 25 29  1  0
 29 30  1  0
 28 31  1  0
 29 32  1  0
 30 33  1  0
 31 34  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4292772

   ---

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: 469.59

Molecular Weight (Monoisotopic): 469.2689

AlogP: 3.55

#Rotatable Bonds: 11

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: ┄

CX Basic pKa: ┄

CX LogP: 4.43

CX LogD: 4.43

Aromatic Rings: 3

Heavy Atoms: 34

QED Weighted: 0.43

Np Likeness Score: -1.33

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]

2. Dąbrowska M, Starek M, Chłoń-Rzepa G, Zagórska A, Komsta Ł, Jankowska A, Ślusarczyk M, Pawłowski M..  (2021)  Estimation of the lipophilicity of purine-2,6-dione-based TRPA1 antagonists and PDE4/7 inhibitors with analgesic activity.,  49  [PMID:34391892] [10.1016/j.bmcl.2021.128318]

Source

Source(1):

• Scientific Literature