(1S,2R,5R)-5-(4-amino-6-fluoro-1H-imidazo[4,5-c]pyridin-1-yl)-3-(2-hydroxyethyl)cyclopent-3-ene-1,2-diol

ID: ALA3604364

PubChem CID: 122185650

Max Phase: Preclinical

Molecular Formula: C13H15FN4O3

Molecular Weight: 294.29

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Nc1nc(F)cc2c1ncn2[C@@H]1C=C(CCO)[C@@H](O)[C@H]1O

Standard InChI:  InChI=1S/C13H15FN4O3/c14-9-4-7-10(13(15)17-9)16-5-18(7)8-3-6(1-2-19)11(20)12(8)21/h3-5,8,11-12,19-21H,1-2H2,(H2,15,17)/t8-,11-,12+/m1/s1

Standard InChI Key:  STALKTAKPTUXFI-FXAINCCUSA-N

Molfile:  

     RDKit          2D

 21 23  0  0  0  0  0  0  0  0999 V2000
   -1.0028    1.5132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3155    0.7475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3155   -0.7475    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0028   -1.5132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2917    0.7475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2917   -0.7475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7138   -1.2033    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5889    0.0182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7138    1.2033    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1749    2.6315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6243    2.9682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7308    4.4645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3406    5.0280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3751    3.8801    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0517    6.1927    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1776    3.9578    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0039    5.2543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9991   -2.7132    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3560    1.3452    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    6.3272    4.5462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3469    5.1788    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  1  1  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  6  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9  5  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 14 10  1  0
 10  9  1  1
 13 15  1  6
 14 16  1  6
 12 17  1  0
  4 18  1  0
  2 19  1  0
 17 20  1  0
 20 21  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3604364

   ---

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: 294.29

Molecular Weight (Monoisotopic): 294.1128

AlogP: -0.26

#Rotatable Bonds: 3

Polar Surface Area: 117.42

Molecular Species: NEUTRAL

HBA: 7

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.11

CX Basic pKa: 4.11

CX LogP: -1.03

CX LogD: -1.03

Aromatic Rings: 2

Heavy Atoms: 21

QED Weighted: 0.46

Np Likeness Score: 0.54

References

1. Liu C, Chen Q, Gorden JD, Schneller SW..  (2015)  2- and 3-Fluoro-3-deazaneplanocins, 2-fluoro-3-deazaaristeromycins, and 3-methyl-3-deazaneplanocin: Synthesis and antiviral properties.,  23  (17): [PMID:26260336] [10.1016/j.bmc.2015.07.039]

Source

Source(1):

• Scientific Literature