Ketcher 05202016042D 1   1.00000     0.00000     0

 18 19  0     0  0            999 V2000
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   -1.8590    3.5750    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.7250    5.0750    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.9650    0.7962    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6372   -1.2729    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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  2  3  1  0     0  0
  3  4  1  0     0  0
  4  5  1  0     0  0
  5  6  2  0     0  0
  6  1  1  0     0  0
  7  4  1  1     0  0
  7  8  1  0     0  0
  8  9  1  0     0  0
  9 10  1  0     0  0
 10 11  2  0     0  0
 11  7  1  0     0  0
  1 12  1  0     0  0
  3 13  2  0     0  0
  8 14  1  6     0  0
  9 15  1  6     0  0
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 16 17  1  0     0  0
 11 18  1  0     0  0
M  END
> <ID>
CHEBI:147412

> <NAME>
roducitabine

> <DEFINITION>
A triol that is (1S,2R)-4-fluoro-3-(hydroxymethyl)cyclopent-3-ene-1,2-diol which is substituted by a 4-amino-2-oxopyrimidin-1(2H)-yl group at position 5. It is a cytidine analog which exhibits anticancer activity in several cancers, including gemcitabine-resistant tumours.

> <STAR>
3

> <SYNONYM>
TV-1360; RX3117; RX-3117; RX 3117; fluorocyclopentenylcytosine; fluorocyclopentenylcytosine; fluorocyclopentenyl-cytosine; fluorocyclopentenyl cytosine; 4-amino-1-[(1S,4R,5S)-2-fluoro-4,5-dihydroxy-3-(hydroxymethyl)cyclopent-2-en-1-yl]-1,2-dihydropyrimidin-2-one; 1-[(1S,4R,5S)-2-fluoro-3-(hydroxymethyl)-4,5-dihydroxy-2-cyclopentenyl]cytosine

> <IUPAC_NAME>
4-amino-1-[(1S,4R,5S)-2-fluoro-4,5-dihydroxy-3-(hydroxymethyl)cyclopent-2-en-1-yl]pyrimidin-2(1H)-one

> <FORMULA>
C10H12FN3O4

> <MASS>
257.221

> <MONOISOTOPIC_MASS>
257.08118

> <CHARGE>
0

> <SMILES>
C1(=NC(N(C=C1)[C@H]2[C@@H]([C@@H](C(=C2F)CO)O)O)=O)N

> <INCHI>
InChI=1S/C10H12FN3O4/c11-6-4(3-15)8(16)9(17)7(6)14-2-1-5(12)13-10(14)18/h1-2,7-9,15-17H,3H2,(H2,12,13,18)/t7-,8-,9+/m1/s1

> <INCHIKEY>
QLLGKCJUPWYJON-HLTSFMKQSA-N

> <CAS_REGISTRY_NUMBER>
865838-26-2

> <CHEMIDPLUS>
865838-26-2

> <KEGG_DRUG_ACCESSION>
D11740

> <PUBMED_CITATION>
22524616; 24048768; 24940694; 25503121; 27612203; 27906620; 27906622; 30663502; 30879349; 31262886; 32295203

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