1-(3-Fluoro-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-5-fluoromethyl-1H-pyrimidine-2,4-dione

ID: ALA2368799

PubChem CID: 15608756

Max Phase: Preclinical

Molecular Formula: C10H12F2N2O5

Molecular Weight: 278.21

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=c1[nH]c(=O)n([C@@H]2O[C@H](CO)[C@@H](O)[C@@H]2F)cc1CF

Standard InChI:  InChI=1S/C10H12F2N2O5/c11-1-4-2-14(10(18)13-8(4)17)9-6(12)7(16)5(3-15)19-9/h2,5-7,9,15-16H,1,3H2,(H,13,17,18)/t5-,6+,7-,9-/m1/s1

Standard InChI Key:  WEPKIVCZNIVAHU-JVZYCSMKSA-N

Molfile:  

     RDKit          2D

 19 20  0  0  1  0  0  0  0  0999 V2000
    8.9669   -1.4594    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.9669   -2.2844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6814   -1.0469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6814   -0.2219    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.2525   -1.0469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6344   -2.7693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2995   -2.7693    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.2525   -0.2219    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9669    0.1906    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3794   -3.5539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5544   -3.5539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3959   -1.4594    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.9669    1.0156    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.4190   -2.5144    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    9.8644   -4.2214    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5380    0.1906    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0695   -4.2214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5380    1.0156    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    8.4051   -4.9750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1
  3  1  1  0
  4  3  1  0
  5  1  1  0
  2  6  1  0
  7  2  1  0
  8  5  2  0
  9  8  1  0
 10  6  1  0
 11  7  1  0
 12  3  2  0
 13  9  2  0
  6 14  1  1
 10 15  1  6
 16  8  1  0
 11 17  1  1
 18 16  1  0
 19 17  1  0
  4  9  1  0
 11 10  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2368799

   1-[(2R,3S,4R,5R)-3-fluoro-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-(fluoromethyl)pyrimidine-2,4-dione

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: 278.21

Molecular Weight (Monoisotopic): 278.0714

AlogP: -1.41

#Rotatable Bonds: 3

Polar Surface Area: 104.55

Molecular Species: NEUTRAL

HBA: 6

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.42

CX Basic pKa: ┄

CX LogP: -1.52

CX LogD: -1.52

Aromatic Rings: 1

Heavy Atoms: 19

QED Weighted: 0.63

Np Likeness Score: 0.61

References

1. Matulic-Adamic J, Takahashi K, Chou TC, Gadler H, Price RW, Reddy AR, Kalman TI, Watanabe KA..  (1988)  Nucleosides. 150. Synthesis and some biological properties of 5-monofluoromethyl, 5-difluoromethyl, and 5-trifluoromethyl derivatives of 2'-deoxyuridine and 2'-deoxy-2'-fluoro-beta-D-arabinofuranosyluracil.,  31  (8): [PMID:2840503] [10.1021/jm00403a026]

Source

Source(1):

• Scientific Literature