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

ID: ALA2368785

Cas Number: 101527-45-1

PubChem CID: 127931

Max Phase: Preclinical

Molecular Formula: C10H13FN2O5

Molecular Weight: 260.22

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=c1[nH]c(=O)n([C@H]2C[C@H](O)[C@@H](CO)O2)cc1CF

Standard InChI:  InChI=1S/C10H13FN2O5/c11-2-5-3-13(10(17)12-9(5)16)8-1-6(15)7(4-14)18-8/h3,6-8,14-15H,1-2,4H2,(H,12,16,17)/t6-,7+,8+/m0/s1

Standard InChI Key:  BQLWSXSBUAEINE-XLPZGREQSA-N

Molfile:  

     RDKit          2D

 18 19  0  0  1  0  0  0  0  0999 V2000
    2.1081   -1.7445    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7726   -2.4981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2575   -3.1656    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6232   -1.0770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9286   -1.6582    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4135   -2.3257    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0780   -3.0793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8782   -0.2924    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7982   -1.0770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2107    0.1925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5433   -0.2924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9521   -2.5844    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5629   -3.7468    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2340   -2.2394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2413   -0.0375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7190   -2.9069    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    1.2107    1.0175    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4963    1.4300    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  2  1  0
  4  1  1  1
  5  1  1  0
  6  5  2  0
  7  6  1  0
  8  4  1  0
  4  9  1  0
 10  8  1  0
 11  9  1  0
 12  2  2  0
 13  7  2  0
 14  6  1  0
 11 15  1  6
 16 14  1  0
 10 17  1  1
 18 17  1  0
  3  7  1  0
 10 11  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2368785

   alpha-Fluorothymidine

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: 260.22

Molecular Weight (Monoisotopic): 260.0808

AlogP: -1.35

#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: 9.38

CX Basic pKa: ┄

CX LogP: -1.51

CX LogD: -1.51

Aromatic Rings: 1

Heavy Atoms: 18

QED Weighted: 0.62

Np Likeness Score: 0.75

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