4-Amino-1-(3,4-dihydroxy-5-methyl-tetrahydro-furan-2-yl)-5-fluoro-1H-pyrimidin-2-one

ID: ALA3244492

Cas Number: 66335-38-4

PubChem CID: 10037499

Product Number: D135998, Order Now?

Max Phase: Preclinical

Molecular Formula: C9H12FN3O4

Molecular Weight: 245.21

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C[C@H]1O[C@@H](n2cc(F)c(N)nc2=O)[C@H](O)[C@@H]1O

Standard InChI:  InChI=1S/C9H12FN3O4/c1-3-5(14)6(15)8(17-3)13-2-4(10)7(11)12-9(13)16/h2-3,5-6,8,14-15H,1H3,(H2,11,12,16)/t3-,5-,6-,8-/m1/s1

Standard InChI Key:  YSNABXSEHNLERR-ZIYNGMLESA-N

Molfile:  

     RDKit          2D

 17 18  0  0  0  0  0  0  0  0999 V2000
    3.2209  -14.3081    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7065  -13.6519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5273  -13.6519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4652  -12.8693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7684  -12.8533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1295  -12.3799    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6850  -12.6163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4963  -12.4577    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.1961  -12.8811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9198  -12.4861    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.9390  -11.6644    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2310  -11.2424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5154  -11.6359    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0134  -14.3159    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1802  -13.6981    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6595  -11.2742    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.2452  -10.4253    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  0
  2  4  1  0
  3  5  1  0
  4  6  1  0
  5  6  1  0
  2  1  1  6
  4  7  1  1
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13  8  1  0
  5  8  1  1
  3 14  1  6
  9 15  2  0
 11 16  1  0
 12 17  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3244492

   5'-Deoxy-5-fluorocytidine

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: 245.21

Molecular Weight (Monoisotopic): 245.0812

AlogP: -1.40

#Rotatable Bonds: 1

Polar Surface Area: 110.60

Molecular Species: NEUTRAL

HBA: 7

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.59

CX Basic pKa: ┄

CX LogP: -1.55

CX LogD: -1.55

Aromatic Rings: 1

Heavy Atoms: 17

QED Weighted: 0.56

Np Likeness Score: 0.89

References

1. Hattori K, Kohchi Y, Oikawa N, Suda H, Ura M, Ishikawa T, Miwa M, Endoh M, Eda H, Tanimura H, Kawashima A, Horii I, Ishitsuka H, Shimma N..  (2003)  Design and synthesis of the tumor-activated prodrug of dihydropyrimidine dehydrogenase (DPD) inhibitor, RO0094889 for combination therapy with capecitabine.,  13  (5): [PMID:12617910] [10.1016/s0960-894x(02)01082-x]

2. Cook AF, Holman MJ, Kramer MJ, Trown PW..  (1979)  Fluorinated pyrimidine nucleosides. 3. Synthesis and antitumor activity of a series of 5'-deoxy-5-fluoropyrimidine nucleosides.,  22  (11): [PMID:533880] [10.1021/jm00197a010]

Source

Source(1):

• Scientific Literature