(R)-3-((2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-3,8-dihydroimidazo[4,5-d][1,3]diazepin-8-ol

ID: ALA1651378

PubChem CID: 53323498

Max Phase: Preclinical

Molecular Formula: C11H14N4O4

Molecular Weight: 266.26

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  OC[C@H]1O[C@@H](n2cnc3c2N=CN=C[C@@H]3O)C[C@@H]1O

Standard InChI:  InChI=1S/C11H14N4O4/c16-3-8-6(17)1-9(19-8)15-5-14-10-7(18)2-12-4-13-11(10)15/h2,4-9,16-18H,1,3H2/t6-,7-,8+,9+/m0/s1

Standard InChI Key:  RTSRXQQKWGEUQK-RBXMUDONSA-N

Molfile:  

     RDKit          2D

 19 21  0  0  0  0  0  0  0  0999 V2000
    4.1388    0.7241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9638    0.7241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2188    1.5088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5513    1.9938    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8839    1.5088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1672    1.9250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4516    1.5143    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7172    0.0138    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9263    1.9297    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.6590    3.0421    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.8885    2.7519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7155    0.6849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4049    1.1286    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.4728    1.9020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9621    0.9557    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.7174    1.7091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1729    2.3989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9312    2.4650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1987    3.1777    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  9 16  1  0
  4  5  1  0
  5  1  1  0
 17 10  1  0
 10 11  2  0
 11  9  1  0
  1  2  1  0
  5  6  1  1
  6  7  1  0
  2  3  1  0
  1  8  1  6
  3  4  1  0
 12 13  1  0
 13 14  2  0
 12 15  2  0
 16 17  2  0
 17 18  1  0
 18 14  1  0
 15 16  1  0
  3  9  1  1
 18 19  1  1
M  END

Alternative Forms

1. Parent:

   

   ALA1651378

   (8R)-3-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-8H-imidazo[4,5-d][1,3]diazepin-8-ol

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: 266.26

Molecular Weight (Monoisotopic): 266.1015

AlogP: -0.70

#Rotatable Bonds: 2

Polar Surface Area: 112.46

Molecular Species: NEUTRAL

HBA: 8

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.50

CX Basic pKa: 3.94

CX LogP: -1.81

CX LogD: -1.81

Aromatic Rings: 1

Heavy Atoms: 19

QED Weighted: 0.65

Np Likeness Score: 1.15

References

1. Gillerman I, Fischer B..  (2011)  Investigations into the origin of the molecular recognition of several adenosine deaminase inhibitors.,  54  (1): [PMID:21138280] [10.1021/jm101286g]

Source

Source(1):

• Scientific Literature