5-(6-Amino-2-fluoro-purin-9-yl)-2-methyl-tetrahydro-furan-3-ol

ID: ALA2079578

PubChem CID: 10399998

Max Phase: Preclinical

Molecular Formula: C10H12FN5O2

Molecular Weight: 253.24

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C[C@H]1O[C@@H](n2cnc3c(N)nc(F)nc32)C[C@@H]1O

Standard InChI:  InChI=1S/C10H12FN5O2/c1-4-5(17)2-6(18-4)16-3-13-7-8(12)14-10(11)15-9(7)16/h3-6,17H,2H2,1H3,(H2,12,14,15)/t4-,5+,6-/m1/s1

Standard InChI Key:  CHNFJOKKVCYPMU-NGJCXOISSA-N

Molfile:  

     RDKit          2D

 18 20  0  0  0  0  0  0  0  0999 V2000
    8.4960   -1.2874    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.7431   -1.0365    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7431   -0.2138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4960   -3.0443    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0320   -1.4548    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.4960    0.0279    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.3209   -0.2138    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.9840   -0.6135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0320    0.2045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3209   -1.0365    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3248   -2.4029    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.0498   -3.9598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6137   -3.9598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1768   -3.0443    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0320    1.0039    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.5958   -1.4408    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    6.1257   -4.7406    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1768   -2.4029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  2  2  0
  4  1  1  1
  5  2  1  0
  6  8  2  0
  7 10  1  0
  8  1  1  0
  9  3  1  0
 10  5  2  0
 11  4  1  0
 12  4  1  0
 13 12  1  0
 14 11  1  0
 15  9  1  0
 16 10  1  0
 13 17  1  6
 14 18  1  1
  6  3  1  0
 14 13  1  0
  7  9  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA2079578

   (2R,3S,5R)-5-(6-amino-2-fluoropurin-9-yl)-2-methyloxolan-3-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: 253.24

Molecular Weight (Monoisotopic): 253.0975

AlogP: 0.22

#Rotatable Bonds: 1

Polar Surface Area: 99.08

Molecular Species: NEUTRAL

HBA: 7

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 0.79

CX LogP: 0.48

CX LogD: 0.48

Aromatic Rings: 2

Heavy Atoms: 18

QED Weighted: 0.70

Np Likeness Score: 0.40

References

1. Ye S, Rezende MM, Deng WP, Herbert B, Daly JW, Johnson RA, Kirk KL..  (2004)  Synthesis of 2',5'-dideoxy-2-fluoroadenosine and 2',5'-dideoxy-2,5'-difluoroadenosine: potent P-site inhibitors of adenylyl cyclase.,  47  (5): [PMID:14971900] [10.1021/jm0303599]

2. Ye S, Rezende MM, Deng WP, Herbert B, Daly JW, Johnson RA, Kirk KL..  (2004)  Synthesis of 2',5'-dideoxy-2-fluoroadenosine and 2',5'-dideoxy-2,5'-difluoroadenosine: potent P-site inhibitors of adenylyl cyclase.,  47  (5): [PMID:14971900] [10.1021/jm0303599]

Source

Source(1):

• Scientific Literature