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CHEBI:147412 - roducitabine

ChEBI IDCHEBI:147412
ChEBI Nameroducitabine
Stars
DefinitionA 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.
Last Modified21 May 2020
SubmitterAnne Morgat
DownloadsMolfile
FormulaC10H12FN3O4
Net Charge0
Average Mass257.221
Monoisotopic Mass257.08118
SMILESNc1ccn([C@@H]2C(F)=C(CO)[C@@H](O)[C@H]2O)c(=O)n1
InChIInChI=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
InChIKeyQLLGKCJUPWYJON-HLTSFMKQSA-N
Roles Classification
Biological Roles:
apoptosis inducer  Any substance that induces the process of apoptosis (programmed cell death) in multi-celled organisms.
DNA synthesis inhibitor  Any substance that inhibits the synthesis of DNA.
antimetabolite  A substance which is structurally similar to a metabolite but which competes with it or replaces it, and so prevents or reduces its normal utilization.
Applications:
antineoplastic agent  A substance that inhibits or prevents the proliferation of neoplasms.
prodrug  A compound that, on administration, must undergo chemical conversion by metabolic processes before becoming the pharmacologically active drug for which it is a prodrug.
ChEBI Ontology
Outgoing Relation(s)
roducitabine (CHEBI:147412) has role antimetabolite (CHEBI:35221)
roducitabine (CHEBI:147412) has role antineoplastic agent (CHEBI:35610)
roducitabine (CHEBI:147412) has role apoptosis inducer (CHEBI:68495)
roducitabine (CHEBI:147412) has role DNA synthesis inhibitor (CHEBI:59517)
roducitabine (CHEBI:147412) has role prodrug (CHEBI:50266)
roducitabine (CHEBI:147412) is a organofluorine compound (CHEBI:37143)
roducitabine (CHEBI:147412) is a primary allylic alcohol (CHEBI:134394)
roducitabine (CHEBI:147412) is a triol (CHEBI:27136)
IUPAC Name 
4-amino-1-[(1S,4R,5S)-2-fluoro-4,5-dihydroxy-3-(hydroxymethyl)cyclopent-2-en-1-yl]pyrimidin-2(1H)-one
Synonyms  Source
RX-3117ChemIDplus
fluorocyclopentenylcytosineChEBI
TV-1360ChEBI
fluorocyclopentenyl-cytosineChEBI
fluorocyclopentenyl cytosineChEBI
RX3117ChemIDplus
UniProt Name  Source
fluorocyclopentenylcytosineUniProt
Manual XrefsDatabases
D11740KEGG DRUG
Registry NumbersSources
CAS:865838-26-2ChemIDplus
Citations