US8470800, D::US8609833, 93

ID: ALA3642152

PubChem CID: 49784884

Max Phase: Preclinical

Molecular Formula: C14H18N6O7

Molecular Weight: 382.33

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=[N+]([O-])OC[C@H]1O[C@@H](n2cnc3c(NC4CCOC4)ncnc32)[C@H](O)[C@@H]1O

Standard InChI:  InChI=1S/C14H18N6O7/c21-10-8(4-26-20(23)24)27-14(11(10)22)19-6-17-9-12(15-5-16-13(9)19)18-7-1-2-25-3-7/h5-8,10-11,14,21-22H,1-4H2,(H,15,16,18)/t7?,8-,10-,11-,14-/m1/s1

Standard InChI Key:  QKLWYFLDTCIMJQ-HVMNINKTSA-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
   -2.8675   -5.1069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3525   -5.3058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9246   -6.6933    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4122   -6.8924    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8697   -8.0018    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1445   -5.9418    0.0000 O   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
   -0.6928   -4.0817    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
    0.3114   -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 O   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  1
  4  5  1  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  3  9  1  0
  9 10  1  0
 10 11  1  0
 11  2  1  0
 11 12  1  6
 10 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  CHG  2   6   1   8  -1
M  END

Alternative Forms

1. Parent:

   

   ALA3642152

   [(2R,3S,4R,5R)-3,4-dihydroxy-5-[6-(oxolan-3-ylamino)purin-9-yl]oxolan-2-yl]methyl nitrate

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: 382.33

Molecular Weight (Monoisotopic): 382.1237

AlogP: -1.15

#Rotatable Bonds: 6

Polar Surface Area: 166.92

Molecular Species: NEUTRAL

HBA: 12

HBD: 3

#RO5 Violations: 1

HBA (Lipinski): 13

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 12.45

CX Basic pKa: 3.71

CX LogP: -1.19

CX LogD: -1.19

Aromatic Rings: 2

Heavy Atoms: 27

QED Weighted: 0.41

Np Likeness Score: 0.43

References

1.  (2013)  Method of reducing intraocular pressure in humans, 

2.  (2013)  Purine derivatives as adenosine A1 receptor agonists and methods of use thereof, 

Source

Source(1):

• BindingDB Database