roducitabine (CHEBI:147412)

ChEBI > Main

Main

ChEBI Ontology

Automatic Xrefs

Reactions

Pathways

Models

ChEBI Name	roducitabine

ChEBI ID	CHEBI:147412

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.

Stars	This entity has been manually annotated by the ChEBI Team.

Submitter	Anne Morgat

Supplier Information

Download	Molfile XML SDF

Formula

C10H12FN3O4

Net Charge

Average Mass

257.221

Monoisotopic Mass

257.08118

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

SMILES

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

Roles Classification
Biological Role(s):	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. DNA synthesis inhibitor Any substance that inhibits the synthesis of DNA. apoptosis inducer Any substance that induces the process of apoptosis (programmed cell death) in multi-celled organisms.

Application(s):	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	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	Sources
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
fluorocyclopentenylcytosine	UniProt
RX 3117	ChemIDplus
RX-3117	ChemIDplus
RX3117	ChemIDplus
TV-1360	ChEBI

Registry Number	Type	Source
865838-26-2	CAS Registry Number	ChemIDplus

Last Modified

21 May 2020