(1R,2S,3R)-3-(4-amino-7-fluoro-1H-imidazo[4,5-c]pyridin-1-yl)cyclopentane-1,2-diol

ID: ALA3290657

PubChem CID: 46174640

Max Phase: Preclinical

Molecular Formula: C11H13FN4O2

Molecular Weight: 252.25

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Nc1ncc(F)c2c1ncn2[C@@H]1CC[C@@H](O)[C@H]1O

Standard InChI:  InChI=1S/C11H13FN4O2/c12-5-3-14-11(13)8-9(5)16(4-15-8)6-1-2-7(17)10(6)18/h3-4,6-7,10,17-18H,1-2H2,(H2,13,14)/t6-,7-,10+/m1/s1

Standard InChI Key:  RMSDZLLFAYEYCD-XSSZXYGBSA-N

Molfile:  

     RDKit          2D

 18 20  0  0  0  0  0  0  0  0999 V2000
    6.2875   -4.4819    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.5185   -4.7300    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9201   -4.9220    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5734   -3.6486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2593   -5.4776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8398   -4.2226    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6607   -4.3769    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0013   -5.7661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4378   -3.6528    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.4343   -5.4776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5070   -6.2677    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1809   -4.6949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4098   -4.7062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7918   -6.1223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1709   -6.2635    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5064   -5.5971    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.0696   -4.2188    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.3160   -6.2570    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1
  1  3  1  0
  1  4  1  0
  5  2  1  0
  2  6  1  0
  3  7  2  0
  3  8  1  0
  4  9  2  0
  5 10  1  0
  5 11  1  6
  6 12  1  0
  7 13  1  0
  8 14  2  0
 10 15  1  6
 13 16  2  0
 13 17  1  0
  7  9  1  0
 10 12  1  0
 14 16  1  0
  8 18  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3290657

   (1R,2S,3R)-3-(4-amino-7-fluoro-1H-imidazo[4,5-c]pyridin-1-yl)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: 252.25

Molecular Weight (Monoisotopic): 252.1023

AlogP: 0.21

#Rotatable Bonds: 1

Polar Surface Area: 97.19

Molecular Species: NEUTRAL

HBA: 6

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.42

CX Basic pKa: 4.08

CX LogP: -0.62

CX LogD: -0.62

Aromatic Rings: 2

Heavy Atoms: 18

QED Weighted: 0.67

Np Likeness Score: 0.53

References

1. Converso A, Hartingh T, Fraley ME, Garbaccio RM, Hartman GD, Huang SY, Majercak JM, McCampbell A, Na SJ, Ray WJ, Savage MJ, Wolffe C, Yeh S, Yu Y, White R, Zhang R..  (2014)  Adenosine analogue inhibitors of S-adenosylhomocysteine hydrolase.,  24  (12): [PMID:24813734] [10.1016/j.bmcl.2014.04.034]

Source

Source(1):

• Scientific Literature