6-(Cyclopentylamino)-9-methyl-8-(4-hydroxyphenyl)-9H-purine

ID: ALA4174108

PubChem CID: 135438480

Max Phase: Preclinical

Molecular Formula: C17H19N5O

Molecular Weight: 309.37

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C17H19N5O/c1-22-16(11-6-8-13(23)9-7-11)21-14-15(18-10-19-17(14)22)20-12-4-2-3-5-12/h6-10,12,23H,2-5H2,1H3,(H,18,19,20)

Standard InChI Key:  OKFLBAVQKOJGFD-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 23 26  0  0  0  0  0  0  0  0999 V2000
    3.7007   -4.9279    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6996   -5.7474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4076   -6.1564    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.4058   -4.5190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1144   -4.9243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1147   -5.7474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8977   -6.0016    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.3814   -5.3355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8973   -4.6697    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.1953   -5.3338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6036   -6.0430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4200   -6.0430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8292   -5.3346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4159   -4.6247    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6009   -4.6282    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4034   -3.7018    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.1504   -6.7788    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6945   -3.2953    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6092   -2.4833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8094   -2.3158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4029   -3.0248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9516   -3.6303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6464   -5.3333    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
 13 23  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4174108

   ---

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: 309.37

Molecular Weight (Monoisotopic): 309.1590

AlogP: 3.09

#Rotatable Bonds: 3

Polar Surface Area: 75.86

Molecular Species: NEUTRAL

HBA: 6

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.62

CX Basic pKa: 3.48

CX LogP: 3.07

CX LogD: 3.07

Aromatic Rings: 3

Heavy Atoms: 23

QED Weighted: 0.78

Np Likeness Score: -0.65

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