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

ID: ALA1229920

Cas Number: 21679-12-9

PubChem CID: 447864

Product Number: F337973, Order Now?

Max Phase: Preclinical

Molecular Formula: C10H12FN5O3

Molecular Weight: 269.24

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C10H12FN5O3/c11-10-14-8(12)7-9(15-10)16(3-13-7)6-1-4(18)5(2-17)19-6/h3-6,17-18H,1-2H2,(H2,12,14,15)/t4-,5+,6+/m0/s1

Standard InChI Key:  ZWPYUXAXLRFWQC-KVQBGUIXSA-N

Molfile:  

     RDKit          2D

 19 21  0  0  0  0  0  0  0  0999 V2000
   -0.9563    3.1245    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4043    2.5114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6592    1.7268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1743    1.0594    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6592    0.3919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4043   -0.3927    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3803   -0.6476    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0948   -0.2351    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8093   -0.6476    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5237   -0.2351    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    1.8093   -1.4726    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0948   -1.8851    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0948   -2.7101    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3803   -1.4726    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4043   -1.7276    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8892   -1.0601    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4439    0.6469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4439    1.4719    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1113    1.9568    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  2  1  1
  3  4  1  0
 18  3  1  0
  5  4  1  0
  5  6  1  1
  5 17  1  0
  7  6  1  0
 16  6  1  0
  7  8  2  0
  7 14  1  0
  9  8  1  0
  9 10  1  0
  9 11  2  0
 12 11  1  0
 12 13  1  0
 14 12  2  0
 14 15  1  0
 16 15  2  0
 17 18  1  0
 18 19  1  6
M  END

Alternative Forms

1. Parent:

   

   ALA1229920

   2-Fluoro-2′-deoxyadenosine

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: 269.24

Molecular Weight (Monoisotopic): 269.0924

AlogP: -0.81

#Rotatable Bonds: 2

Polar Surface Area: 119.31

Molecular Species: NEUTRAL

HBA: 8

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.89

CX Basic pKa: 0.79

CX LogP: -0.57

CX LogD: -0.57

Aromatic Rings: 2

Heavy Atoms: 19

QED Weighted: 0.61

Np Likeness Score: 0.80

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]

3. Montgomery JA, Shortnacy-Fowler AT, Clayton SD, Riordan JM, Secrist JA..  (1992)  Synthesis and biologic activity of 2'-fluoro-2-halo derivatives of 9-beta-D-arabinofuranosyladenine.,  35  (2): [PMID:1732556] [10.1021/jm00080a029]

Source

Source(1):

• Scientific Literature