4-(6-Amino-purin-9-yl)-cyclopentane-1,2,3-triol

ID: ALA405082

PubChem CID: 469184

Max Phase: Preclinical

Molecular Formula: C10H13N5O3

Molecular Weight: 251.25

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Nc1ncnc2c1ncn2[C@@H]1C[C@@H](O)[C@@H](O)[C@H]1O

Standard InChI:  InChI=1S/C10H13N5O3/c11-9-6-10(13-2-12-9)15(3-14-6)4-1-5(16)8(18)7(4)17/h2-5,7-8,16-18H,1H2,(H2,11,12,13)/t4-,5-,7+,8-/m1/s1

Standard InChI Key:  VFKHECGAEJNAMV-HXOWADHMSA-N

Molfile:  

     RDKit          2D

 18 20  0  0  1  0  0  0  0  0999 V2000
   -3.2412  -20.1613    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5724  -19.6781    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8252  -18.8928    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6503  -18.8905    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9073  -19.6745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2435  -20.9863    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7885  -19.9353    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4980  -18.1373    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4798  -16.8053    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9727  -17.4646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7003  -17.0705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7142  -17.8922    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0107  -18.3134    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2928  -17.9140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2827  -17.0890    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9869  -16.6717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9764  -15.8466    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6926  -19.9273    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  4  1  0
  4  5  1  0
 11  9  1  0
  9 10  2  0
 10  8  1  0
  5  1  1  0
  1  2  1  0
 11 12  2  0
  1  6  1  6
 12 13  1  0
 13 14  2  0
  2  7  1  6
 14 15  1  0
  2  3  1  0
 15 16  2  0
 16 11  1  0
  3  8  1  1
 16 17  1  0
  8 12  1  0
  5 18  1  6
M  END

Alternative Forms

1. Parent:

   

   ALA405082

   (1R,2R,3S,4R)-4-(6-aminopurin-9-yl)cyclopentane-1,2,3-triol

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: 251.25

Molecular Weight (Monoisotopic): 251.1018

AlogP: -1.56

#Rotatable Bonds: 1

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: 12.95

CX Basic pKa: 3.69

CX LogP: -2.25

CX LogD: -2.25

Aromatic Rings: 2

Heavy Atoms: 18

QED Weighted: 0.48

Np Likeness Score: 0.93

References

1. Siddiqi SM, Chen X, Schneller SW, Ikeda S, Snoeck R, Andrei G, Balzarini J, De Clercq E..  (1994)  An epimer of 5'-noraristeromycin and its antiviral properties.,  37  (9): [PMID:8176716] [10.1021/jm00035a020]

2. Ando T, Kojima K, Chahota P, Kozaki A, Milind ND, Kitade Y..  (2008)  Synthesis of 4'-modified noraristeromycins to clarify the effect of the 4'-hydroxyl groups for inhibitory activity against S-adenosyl-L-homocysteine hydrolase.,  18  (8): [PMID:18374570] [10.1016/j.bmcl.2008.03.029]

Source

Source(1):

• Scientific Literature