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

ID: ALA2079579

PubChem CID: 11357731

Max Phase: Preclinical

Molecular Formula: C10H11F2N5O2

Molecular Weight: 271.23

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Nc1nc(F)nc2c1ncn2[C@H]1C[C@H](O)[C@@H](CF)O1

Standard InChI:  InChI=1S/C10H11F2N5O2/c11-2-5-4(18)1-6(19-5)17-3-14-7-8(13)15-10(12)16-9(7)17/h3-6,18H,1-2H2,(H2,13,15,16)/t4-,5+,6+/m0/s1

Standard InChI Key:  FLPYAKWFUWVFFT-KVQBGUIXSA-N

Molfile:  

     RDKit          2D

 19 21  0  0  0  0  0  0  0  0999 V2000
    7.8965   -1.1201    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.1435   -0.8692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1435   -0.0465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8965   -2.8770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4324   -1.2874    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.8965    0.1952    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.7213   -0.0465    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.3845   -0.4462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4324    0.3718    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7213   -0.8692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7252   -2.2356    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4503   -3.7925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5772   -2.8770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0141   -3.7925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4324    1.1712    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.9963   -1.2735    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    5.5261   -4.5733    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5772   -2.2356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0242   -1.9149    0.0000 F   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 11  1  0
 14 12  1  0
 15  9  1  0
 16 10  1  0
 14 17  1  6
 13 18  1  1
 19 18  1  0
  6  3  1  0
 13 14  1  0
  7  9  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA2079579

   (2S,3S,5R)-5-(6-amino-2-fluoropurin-9-yl)-2-(fluoromethyl)oxolan-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: 271.23

Molecular Weight (Monoisotopic): 271.0881

AlogP: 0.17

#Rotatable Bonds: 2

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: 13.97

CX Basic pKa: 0.79

CX LogP: 0.32

CX LogD: 0.32

Aromatic Rings: 2

Heavy Atoms: 19

QED Weighted: 0.76

Np Likeness Score: 0.47

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