US8609833, 91

ID: ALA3642984

PubChem CID: 91808703

Max Phase: Preclinical

Molecular Formula: C15H21N5O6S

Molecular Weight: 399.43

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=S(=O)(O)C[C@H]1O[C@@H](n2cnc3c(NC4CCCC4)ncnc32)[C@H](O)[C@@H]1O

Standard InChI:  InChI=1S/C15H21N5O6S/c21-11-9(5-27(23,24)25)26-15(12(11)22)20-7-18-10-13(16-6-17-14(10)20)19-8-3-1-2-4-8/h6-9,11-12,15,21-22H,1-5H2,(H,16,17,19)(H,23,24,25)/t9-,11-,12-,15-/m1/s1

Standard InChI Key:  KOJCBXLMZVHBHI-SDBHATRESA-N

Molfile:  

     RDKit          2D

 27 30  0  0  1  0  0  0  0  0999 V2000
   -2.0533   -7.3748    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8348   -6.1949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4810   -5.5489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5772   -6.1149    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6928   -4.0817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1519   -3.7886    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8675   -5.1069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3533   -5.2996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2654   -4.1077    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4554   -4.2620    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8043   -2.9998    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9942   -3.1544    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3114   -2.9665    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8032   -3.1233    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4133   -1.7530    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2990   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2990    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5972    1.5031    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5951    3.0039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8056    3.8680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3371    5.2929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8371    5.2877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3786    3.8595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.5000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990   -0.7500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6
  2  3  1  0
  3  4  1  6
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  2  1  0
  7  8  1  1
  8  9  1  0
  9 10  2  0
  9 11  2  0
  9 12  1  0
  5 13  1  1
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 19  1  0
 17 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 13  1  0
 27 16  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3642984

   [(2S,3S,4R,5R)-5-[6-(cyclopentylamino)purin-9-yl]-3,4-dihydroxyoxolan-2-yl]methanesulfonic acid

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: 399.43

Molecular Weight (Monoisotopic): 399.1213

AlogP: -0.31

#Rotatable Bonds: 5

Polar Surface Area: 159.69

Molecular Species: ACID

HBA: 10

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 11

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 1

CX Acidic pKa: -1.29

CX Basic pKa: 4.71

CX LogP: -3.82

CX LogD: -3.10

Aromatic Rings: 2

Heavy Atoms: 27

QED Weighted: 0.49

Np Likeness Score: 0.41

References

1.  (2013)  Purine derivatives as adenosine A1 receptor agonists and methods of use thereof, 

Source

Source(1):

• BindingDB Database