(1R,2S,3R,5R)-3-(6-Amino-9H-purin-9-yl)-5-((R)-2-hydroxypropyl)cyclopentane-1,2-diol

ID: ALA2397387

PubChem CID: 71723319

Max Phase: Preclinical

Molecular Formula: C13H19N5O3

Molecular Weight: 293.33

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C[C@@H](O)C[C@H]1C[C@@H](n2cnc3c(N)ncnc32)[C@H](O)[C@@H]1O

Standard InChI:  InChI=1S/C13H19N5O3/c1-6(19)2-7-3-8(11(21)10(7)20)18-5-17-9-12(14)15-4-16-13(9)18/h4-8,10-11,19-21H,2-3H2,1H3,(H2,14,15,16)/t6-,7+,8-,10-,11+/m1/s1

Standard InChI Key:  GKBQORWUVIAVKO-BEBVASNESA-N

Molfile:  

     RDKit          2D

 21 23  0  0  0  0  0  0  0  0999 V2000
   19.1717   -6.9427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.6375   -2.6971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.6359   -3.5238    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.3461   -3.9364    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   23.0614   -3.5272    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.0630   -2.7078    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.3564   -2.2969    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8573   -2.4388    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.3644   -3.0997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8500   -3.7752    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.5902   -4.5585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7995   -4.8112    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8000   -5.6351    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5826   -5.8955    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.0760   -5.2435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.8991   -5.2466    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.8284   -6.6830    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.3559   -1.4722    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.1301   -6.1188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4780   -7.3910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9045   -7.3222    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  2  2  0
  2  8  1  0
  8  9  2  0
  9 10  1  0
 10  3  1  0
 11 10  1  1
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 11  1  0
 15 16  1  6
 14 17  1  6
  7 18  1  0
 13 19  1  1
 19  1  1  0
  1 20  1  0
  1 21  1  6
M  END

Alternative Forms

1. Parent:

   

   ALA2397387

   (1R,2S,3R,5R)-3-(6-aminopurin-9-yl)-5-[(2R)-2-hydroxypropyl]cyclopentane-1,2-diol

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: 293.33

Molecular Weight (Monoisotopic): 293.1488

AlogP: -0.54

#Rotatable Bonds: 3

Polar Surface Area: 130.31

Molecular Species: NEUTRAL

HBA: 8

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.35

CX Basic pKa: 3.69

CX LogP: -1.31

CX LogD: -1.31

Aromatic Rings: 2

Heavy Atoms: 21

QED Weighted: 0.60

Np Likeness Score: 1.06

References

1. Yang M, Ye W, Schneller SW..  (2013)  6'-Methyl-5'-homoaristeromycin: a structural variation of the anti-orthopox virus candidate 5'-homoaristeromycin.,  21  (14): [PMID:23727195] [10.1016/j.bmc.2013.04.070]

Source

Source(1):

• Scientific Literature