(2R,3R,4S,5R)-2-((R)-8-hydroxyimidazo[4,5-d][1,3]diazepin-3(8H)-yl)-5-(hydroxymethyl)tetrahydrofuran-3,4-diol

ID: ALA1651377

PubChem CID: 53318756

Max Phase: Preclinical

Molecular Formula: C11H14N4O5

Molecular Weight: 282.26

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C11H14N4O5/c16-2-6-8(18)9(19)11(20-6)15-4-14-7-5(17)1-12-3-13-10(7)15/h1,3-6,8-9,11,16-19H,2H2/t5-,6+,8+,9+,11+/m0/s1

Standard InChI Key:  XGANFQBJMNBMCZ-DANLAGSESA-N

Molfile:  

     RDKit          2D

 20 22  0  0  0  0  0  0  0  0999 V2000
   -3.8868    0.7975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0618    0.7975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8068    1.5822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4743    2.0672    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1417    1.5822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8584    1.9984    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5739    1.5877    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3084    0.0871    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6584    0.0871    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0992    2.0029    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3666    3.1155    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1370    2.8253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3101    0.7582    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3794    1.2020    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4473    1.9754    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0634    1.0290    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3081    1.7825    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8526    2.4723    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0943    2.5384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1730    3.2511    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3 10  1  1
 10 17  1  0
  5  1  1  0
  1  2  1  0
 18 11  1  0
 11 12  2  0
 12 10  1  0
  5  6  1  1
  6  7  1  0
  2  3  1  0
  1  8  1  6
  3  4  1  0
  2  9  1  6
 13 14  1  0
 14 15  2  0
 13 16  2  0
 17 18  2  0
 18 19  1  0
 19 15  1  0
 16 17  1  0
  4  5  1  0
 19 20  1  1
M  END

Alternative Forms

1. Parent:

   

   ALA1651377

   (2R,3R,4S,5R)-2-[(8R)-8-hydroxy-8H-imidazo[4,5-d][1,3]diazepin-3-yl]-5-(hydroxymethyl)oxolane-3,4-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: 282.26

Molecular Weight (Monoisotopic): 282.0964

AlogP: -1.73

#Rotatable Bonds: 2

Polar Surface Area: 132.69

Molecular Species: NEUTRAL

HBA: 9

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.18

CX Basic pKa: 3.90

CX LogP: -2.71

CX LogD: -2.71

Aromatic Rings: 1

Heavy Atoms: 20

QED Weighted: 0.51

Np Likeness Score: 1.32

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