[1-(2',5',6'-trideoxy-beta-D-ribo-hexofuranosyl)-5-fluoro-uracil]-6'-phosphonic acid

ID: ALA3230503

PubChem CID: 21125857

Max Phase: Preclinical

Molecular Formula: C10H14FN2O7P

Molecular Weight: 324.20

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C10H14FN2O7P/c11-5-4-13(10(16)12-9(5)15)8-3-6(14)7(20-8)1-2-21(17,18)19/h4,6-8,14H,1-3H2,(H,12,15,16)(H2,17,18,19)/t6-,7+,8+/m0/s1

Standard InChI Key:  AVQMCZOTCNTEPR-XLPZGREQSA-N

Molfile:  

     RDKit          2D

 21 22  0  0  0  0  0  0  0  0999 V2000
    7.4376   -8.4252    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7251   -8.0127    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    6.7242   -8.8360    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.2127   -3.4417    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.2127   -4.2668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9247   -4.6751    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.6367   -4.2668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6367   -3.4417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9247   -3.0251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9280   -5.4976    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2606   -5.9826    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5155   -6.7673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3406   -6.7673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5954   -5.9826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0306   -7.4347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8256   -7.4347    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2101   -7.3485    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9046   -7.9297    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.9247   -2.2001    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4988   -4.6803    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.3524   -3.0314    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  2  1  0
  4  5  1  0
  4  9  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 10  1  0
 10  6  1  1
 12 15  1  1
 13 16  1  6
 15 17  1  0
 17  2  1  0
  2 18  2  0
  9 19  2  0
  5 20  2  0
  8 21  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3230503

   2-[(2R,3S,5R)-5-(5-fluoro-2,4-dioxopyrimidin-1-yl)-3-hydroxyoxolan-2-yl]ethylphosphonic 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: 324.20

Molecular Weight (Monoisotopic): 324.0523

AlogP: -1.11

#Rotatable Bonds: 4

Polar Surface Area: 141.85

Molecular Species: ACID

HBA: 6

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 1.81

CX Basic pKa: ┄

CX LogP: -1.81

CX LogD: -4.25

Aromatic Rings: 1

Heavy Atoms: 21

QED Weighted: 0.51

Np Likeness Score: 0.52

References

1. Montgomery JA, Thomas HJ, Kisliuk RL, Gaumont Y..  (1979)  Phosphonate analogue of 2'-deoxy-5-fluorouridylic acid.,  22  (1): [PMID:423172] [10.1021/jm00187a024]

Source

Source(1):

• Scientific Literature