4-(6-(Cyclopentylamino)-9-methyl-9H-purin-8-yl)benzoic acid

ID: ALA4167197

PubChem CID: 145954995

Max Phase: Preclinical

Molecular Formula: C18H19N5O2

Molecular Weight: 337.38

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cn1c(-c2ccc(C(=O)O)cc2)nc2c(NC3CCCC3)ncnc21

Standard InChI:  InChI=1S/C18H19N5O2/c1-23-16(11-6-8-12(9-7-11)18(24)25)22-14-15(19-10-20-17(14)23)21-13-4-2-3-5-13/h6-10,13H,2-5H2,1H3,(H,24,25)(H,19,20,21)

Standard InChI Key:  LZRUOHXWFCFBQE-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 25 28  0  0  0  0  0  0  0  0999 V2000
    3.7709  -11.3498    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7697  -12.1694    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4778  -12.5783    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.4760  -10.9410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1846  -11.3462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1849  -12.1694    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9678  -12.4236    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.4515  -11.7574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9674  -11.0917    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.2655  -11.7557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6737  -12.4649    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4902  -12.4650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8993  -11.7566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4861  -11.0467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6710  -11.0501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4735  -10.1238    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.2206  -13.2007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7646   -9.7173    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6794   -8.9053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8795   -8.7377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4730   -9.4467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0217  -10.0523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7172  -11.7555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1270  -12.4625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.1246  -11.0471    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  6  2  0
  5  4  2  0
  4  1  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9  5  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 10  1  0
  8 10  1  0
  4 16  1  0
  7 17  1  0
 16 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 18  1  0
 23 24  1  0
 23 25  2  0
 13 23  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4167197

   ---

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: 337.38

Molecular Weight (Monoisotopic): 337.1539

AlogP: 3.08

#Rotatable Bonds: 4

Polar Surface Area: 92.93

Molecular Species: ACID

HBA: 6

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 2.83

CX Basic pKa: 4.55

CX LogP: 2.26

CX LogD: -0.18

Aromatic Rings: 3

Heavy Atoms: 25

QED Weighted: 0.76

Np Likeness Score: -0.81

References

1. Lambertucci C, Marucci G, Dal Ben D, Buccioni M, Spinaci A, Kachler S, Klotz KN, Volpini R..  (2018)  New potent and selective A1 adenosine receptor antagonists as potential tools for the treatment of gastrointestinal diseases.,  151  [PMID:29614417] [10.1016/j.ejmech.2018.03.067]

Source

Source(1):

• Scientific Literature