roducitabine (CHEBI:147412)

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CHEBI:147412 - roducitabine

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ChEBI ID	CHEBI:147412
ChEBI Name	roducitabine
Stars
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.
Last Modified	21 May 2020
Submitter	Anne Morgat
Downloads	Molfile

Formula	C10H12FN3O4
Net Charge	0
Average Mass	257.221
Monoisotopic Mass	257.08118
SMILES	Nc1ccn([C@@H]2C(F)=C(CO)[C@@H](O)[C@H]2O)c(=O)n1
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

Roles Classification

Biological Roles:	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. apoptosis inducer Any substance that induces the process of apoptosis (programmed cell death) in multi-celled organisms.
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
1-[(1S,4R,5S)-2-fluoro-3-(hydroxymethyl)-4,5-dihydroxy-2-cyclopentenyl]cytosine	ChEBI
4-amino-1-[(1S,4R,5S)-2-fluoro-4,5-dihydroxy-3-(hydroxymethyl)cyclopent-2-en-1-yl]-1,2-dihydropyrimidin-2-one	ChEBI
fluorocyclopentenyl cytosine	ChEBI
fluorocyclopentenyl-cytosine	ChEBI
fluorocyclopentenylcytosine	ChEBI
RX 3117	ChemIDplus

UniProt Name	Source
fluorocyclopentenylcytosine	UniProt

Manual Xrefs	Databases
D11740	KEGG DRUG

Registry Numbers	Sources
CAS:865838-26-2	ChemIDplus

Citations