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

ID: ALA2368768

PubChem CID: 3007909

Max Phase: Preclinical

Molecular Formula: C10H13FN2O6

Molecular Weight: 276.22

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)cc1CO

Standard InChI:  InChI=1S/C10H13FN2O6/c11-6-7(16)5(3-15)19-9(6)13-1-4(2-14)8(17)12-10(13)18/h1,5-7,9,14-16H,2-3H2,(H,12,17,18)/t5-,6+,7-,9-/m1/s1

Standard InChI Key:  QQGGRUHEDAEEQQ-JVZYCSMKSA-N

Molfile:  

     RDKit          2D

 19 20  0  0  1  0  0  0  0  0999 V2000
    8.9669   -1.4594    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.9669   -2.2844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6814   -1.0469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6814   -0.2219    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.2525   -1.0469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6344   -2.7693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2995   -2.7693    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.2525   -0.2219    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9669    0.1906    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3794   -3.5539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5544   -3.5539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3959   -1.4594    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.9669    1.0156    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.4190   -2.5144    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    9.8644   -4.2214    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5380    0.1906    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0695   -4.2214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5380    1.0156    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.4051   -4.9750    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  1  1  0
  2  6  1  0
  7  2  1  0
  8  5  2  0
  9  8  1  0
 10  6  1  0
 11  7  1  0
 12  3  2  0
 13  9  2  0
  6 14  1  1
 10 15  1  6
 16  8  1  0
 11 17  1  1
 18 16  1  0
 19 17  1  0
  4  9  1  0
 11 10  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2368768

   1-(3-Fluoro-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-5-hydroxymethyl-1H-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: 276.22

Molecular Weight (Monoisotopic): 276.0758

AlogP: -2.38

#Rotatable Bonds: 3

Polar Surface Area: 124.78

Molecular Species: NEUTRAL

HBA: 7

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.74

CX Basic pKa: ┄

CX LogP: -2.41

CX LogD: -2.41

Aromatic Rings: 1

Heavy Atoms: 19

QED Weighted: 0.49

Np Likeness Score: 0.72

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