Trifluoromethyl-phosphonic acid mono-[5-(5-fluoro-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-3-hydroxy-tetrahydro-furan-2-ylmethyl] ester

ID: ALA3143930

Cas Number: 149894-51-9

PubChem CID: 90663650

Max Phase: Preclinical

Molecular Formula: C10H11F4N2O7P

Molecular Weight: 378.17

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=c1[nH]c(=O)n([C@H]2C[C@H](O)[C@@H](COP(=O)(O)C(F)(F)F)O2)cc1F

Standard InChI:  InChI=1S/C10H11F4N2O7P/c11-4-2-16(9(19)15-8(4)18)7-1-5(17)6(23-7)3-22-24(20,21)10(12,13)14/h2,5-7,17H,1,3H2,(H,20,21)(H,15,18,19)/t5-,6+,7+/m0/s1

Standard InChI Key:  GZDLQMAGLXOIPV-RRKCRQDMSA-N

Molfile:  

     RDKit          2D

 24 25  0  0  0  0  0  0  0  0999 V2000
    2.4539   -3.9321    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1183   -4.6858    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6032   -5.3532    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9690   -3.2647    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2744   -3.8459    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2709    0.0674    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    3.7593   -4.5133    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4237   -5.2670    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2709    0.8924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2239   -2.4800    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1440   -3.2647    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5565   -1.9951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2709   -0.7576    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8890   -2.4800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5565   -1.1701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2978   -4.7720    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0959    0.0674    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9086   -5.9344    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5798   -4.4271    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    1.4459    0.0674    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2709    1.7174    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    3.0959    0.8924    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    1.4459    0.8924    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    0.1044   -2.2251    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 13  1  0
  7  5  2  0
  8  7  1  0
  9  6  1  0
 10  4  1  0
 11  4  1  0
 12 10  1  0
 13 15  1  0
 14 11  1  0
 12 15  1  1
 16  2  2  0
 17  6  2  0
 18  8  2  0
 19  7  1  0
 20  6  1  0
 21  9  1  0
 22  9  1  0
 23  9  1  0
 14 24  1  6
  8  3  1  0
 14 12  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3143930

   Uridine, 2'-deoxy-5-fluoro-, 5'-[hydrogen (trifluoromethyl)phosphonate]

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: 378.17

Molecular Weight (Monoisotopic): 378.0240

AlogP: 0.05

#Rotatable Bonds: 4

Polar Surface Area: 130.85

Molecular Species: ACID

HBA: 7

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: -0.51

CX Basic pKa: ┄

CX LogP: 0.54

CX LogD: -1.88

Aromatic Rings: 1

Heavy Atoms: 24

QED Weighted: 0.50

Np Likeness Score: 0.45

References

1. Casara PJ, Jund KC, Clauss A, Nave J, Snyder RD.  (1992)  Synthesis of acid stable 5-o-fluoromethyl phosphonates of nucleosides. Evaluation as inhibitors of reverse transcriptase.,  2  (2): [10.1016/S0960-894X(01)80437-6]

Source

Source(1):

• Scientific Literature