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3094-09-5 molecular structure
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1-[(3R,4S,5R)-3,4-dihydroxy-5-methyloxolan-2-yl]-5-fluoro-1,2,3,4-tetrahydropyrimidine-2,4-dione hydrochloride

ChemBase ID: 120168
Molecular Formular: C9H12ClFN2O5
Molecular Mass: 282.6533832
Monoisotopic Mass: 282.04187739
SMILES and InChIs

SMILES:
n1(C2[C@@H]([C@@H]([C@H](O2)C)O)O)c(=O)[nH]c(=O)c(c1)F.Cl
Canonical SMILES:
C[C@H]1OC([C@@H]([C@@H]1O)O)n1cc(F)c(=O)[nH]c1=O.Cl
InChI:
InChI=1S/C9H11FN2O5.ClH/c1-3-5(13)6(14)8(17-3)12-2-4(10)7(15)11-9(12)16;/h2-3,5-6,8,13-14H,1H3,(H,11,15,16);1H/t3-,5-,6-,8?;/m1./s1
InChIKey:
QLUHBFPFKMSHMP-COAGBBGMSA-N

Cite this record

CBID:120168 http://www.chembase.cn/molecule-120168.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
1-[(3R,4S,5R)-3,4-dihydroxy-5-methyloxolan-2-yl]-5-fluoro-1,2,3,4-tetrahydropyrimidine-2,4-dione hydrochloride
IUPAC Traditional name
1-[(3R,4S,5R)-3,4-dihydroxy-5-methyloxolan-2-yl]-5-fluoro-3H-pyrimidine-2,4-dione hydrochloride
1-[(3R,4S,5R)-3,4-dihydroxy-5-methyloxolan-2-yl]-5-fluoro-1,2,3,4-tetrahydropyrimidine-2,4-dione hydrochloride
Synonyms
1-((3R,4S,5R)-3,4-dihydroxy-5-methyltetrahydrofuran-2-yl)-5-fluoropyrimidine-2,4(1H,3H)-dione hydrochloride
Doxifluridine Hydrochloride
CAS Number
3094-09-5
PubChem SID
162214521
PubChem CID
51052078

DATA SOURCES

DATA SOURCES

All Sources Commercial Sources Non-commercial Sources
Data Source Data ID
PubChem 51052078 external link

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem
Acid pKa 7.6742187  H Acceptors
H Donor LogD (pH = 5.5) -1.1717542 
LogD (pH = 7.4) -1.3514775  Log P -1.1688893 
Molar Refractivity 51.2248 cm3 Polarizability 20.08188 Å3
Polar Surface Area 99.1 Å2 Rotatable Bonds
Lipinski's Rule of Five true 

PROPERTIES

PROPERTIES

Pharmacology Properties Product Information Bioassay(PubChem)
Mechanism of Action
Prodrug of 5-Fluoro-2,4(1 H ,3 H) -pyrimidinedione expand Show data source
Salt Data
HCl expand Show data source
Application(s)
Antineoplastic agent expand Show data source

DETAILS

DETAILS

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • Cook, A.F. et al., J. Med. Chem., 1979, 22, 1330, (synth, pharmacol)
  • • Schwarz, B. et al., Coll. Czech. Chem. Comm., 1980, 45, 3217, (synth)
  • • Bollag, W. et al., Eur. J. Cancer, 1980, 16, 427, (pharmacol)
  • • Scott, J.W. et al., J. Carbohydr., Nucleosides, Nucleotides, 1981, 8, 171, (synth)
  • • Kiss, J. et al., Helv. Chim. Acta, 1982, 65, 1522, (synth)
  • • Sommadossi, J.P. et al., Cancer Res., 1983, 43, 930, (metab)
  • • Kono, A. et al., Chem. Pharm. Bull., 1983, 31, 1666, (hplc)
  • • Sommadossi, J.P. et al., Int. Congr. Ser. Excerpta Med., 1984, 647, 108, (pharmacol, metab)
  • • Meynial, D. et al., J. Pharm. Pharmacol., 1986, 38, 426, (metab)
  • • Au, J.L.S. et al., J. Pharm. Sci., 1987, 76, 699, (metab)
  • • Guerrieri, A. et al., J. Chromatogr., 1993, 617, 71, (hplc)
  • • Martindale, The Extra Pharmacopoeia, 30th edn., Pharmaceutical Press, 1993, 475
  • • Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, DYE415
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PATENTS

PATENTS

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INTERNET

INTERNET

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