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

ID: ALA3143929

PubChem CID: 90663649

Max Phase: Preclinical

Molecular Formula: C10H12F3N2O7P

Molecular Weight: 360.18

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)O2)cc1F

Standard InChI:  InChI=1S/C10H12F3N2O7P/c11-4-2-15(10(18)14-8(4)17)7-1-5(16)6(22-7)3-21-23(19,20)9(12)13/h2,5-7,9,16H,1,3H2,(H,19,20)(H,14,17,18)/t5-,6+,7+/m0/s1

Standard InChI Key:  XSCMSBRGGYQAHA-RRKCRQDMSA-N

Molfile:  

     RDKit          2D

 23 24  0  0  0  0  0  0  0  0999 V2000
    3.2202   -3.7274    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8846   -4.4811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3696   -5.1485    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7353   -3.0600    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0407   -3.6412    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5256   -4.3086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6083    0.2721    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    4.1900   -5.0623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9902   -2.2754    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9103   -3.0600    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3228   -1.7904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6083    1.0971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6083   -0.5529    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6553   -2.2754    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3228   -0.9654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0642   -4.5673    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4333    0.2721    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6750   -5.7297    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3461   -4.2224    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    0.7833    0.2721    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8938    1.5096    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    2.3228    1.5096    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    0.8707   -2.0204    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 13  1  0
  8  6  1  0
  9  4  1  0
 10  4  1  0
 11  9  1  0
 12  7  1  0
 13 15  1  0
 14 10  1  0
 11 15  1  1
 16  2  2  0
 17  7  2  0
 18  8  2  0
 19  6  1  0
 20  7  1  0
 21 12  1  0
 22 12  1  0
 14 23  1  6
  8  3  1  0
 14 11  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3143929

   difluoromethyl-[[(2R,3S,5R)-5-(5-fluoro-2,4-dioxopyrimidin-1-yl)-3-hydroxyoxolan-2-yl]methoxy]phosphinic acid

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: 360.18

Molecular Weight (Monoisotopic): 360.0334

AlogP: -0.25

#Rotatable Bonds: 5

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: 0.18

CX Basic pKa: ┄

CX LogP: -0.11

CX LogD: -2.50

Aromatic Rings: 1

Heavy Atoms: 23

QED Weighted: 0.62

Np Likeness Score: 0.43

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