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

ID: ALA2368781

PubChem CID: 15608759

Max Phase: Preclinical

Molecular Formula: C10H11F3N2O5

Molecular Weight: 296.20

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)cc1C(F)F

Standard InChI:  InChI=1S/C10H11F3N2O5/c11-5-6(17)4(2-16)20-9(5)15-1-3(7(12)13)8(18)14-10(15)19/h1,4-7,9,16-17H,2H2,(H,14,18,19)/t4-,5+,6-,9-/m1/s1

Standard InChI Key:  JURCDKOMRODTHK-FMDIHHLLSA-N

Molfile:  

     RDKit          2D

 20 21  0  0  1  0  0  0  0  0999 V2000
    9.2154   -1.4764    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.2154   -2.3014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9299   -1.0639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9299   -0.2389    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.5010   -0.2389    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5010   -1.0639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2154    0.1736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8829   -2.7863    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5480   -2.7863    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.6279   -3.5709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8029   -3.5709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7865    0.1736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6444   -1.4764    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2154    0.9986    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.6675   -2.5314    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   10.1129   -4.2384    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7865    0.9986    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    7.0720   -0.2389    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    8.3180   -4.2384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6536   -4.9921    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  6  2  0
  6  1  1  0
  7  5  1  0
  2  8  1  0
  9  2  1  0
 10  8  1  0
 11  9  1  0
 12  5  1  0
 13  3  2  0
 14  7  2  0
  8 15  1  1
 10 16  1  6
 17 12  1  0
 18 12  1  0
 11 19  1  1
 20 19  1  0
  4  7  1  0
 11 10  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2368781

   5-(difluoromethyl)-1-[(2R,3S,4R,5R)-3-fluoro-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]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: 296.20

Molecular Weight (Monoisotopic): 296.0620

AlogP: -0.94

#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: 8.94

CX Basic pKa: ┄

CX LogP: -1.25

CX LogD: -1.27

Aromatic Rings: 1

Heavy Atoms: 20

QED Weighted: 0.67

Np Likeness Score: 0.32

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