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CHEBI:90225 - rubitecan

ChEBI IDCHEBI:90225
ChEBI Namerubitecan
Stars
DefinitionA pyranoindolizinoquinoline that is camptothecin in which the hydrogen at position 9 has been replaced by a nitro group. It is a prodrug for 9-aminocamptothecin.
Last Modified22 February 2017
SubmitterGareth Owen
DownloadsMolfile
FormulaC20H15N3O6
Net Charge0
Average Mass393.355
Monoisotopic Mass393.09609
SMILESCC[C@@]1(O)C(=O)OCc2c1cc1n(c2=O)Cc2cc3c([N+](=O)[O-])cccc3nc2-1
InChIInChI=1S/C20H15N3O6/c1-2-20(26)13-7-16-17-10(8-22(16)18(24)12(13)9-29-19(20)25)6-11-14(21-17)4-3-5-15(11)23(27)28/h3-7,26H,2,8-9H2,1H3/t20-/m0/s1
InChIKeyVHXNKPBCCMUMSW-FQEVSTJZSA-N
Wikipedia
Roles Classification
Biological Role:
EC 5.99.1.2 (DNA topoisomerase) inhibitor  A topoisomerase inhibitor that inhibits the bacterial enzymes of the DNA topoisomerases, Type I class (EC 5.99.1.2) that catalyze ATP-independent breakage of one of the two strands of DNA, passage of the unbroken strand through the break, and rejoining of the broken strand. These bacterial enzymes reduce the topological stress in the DNA structure by relaxing negatively, but not positively, supercoiled DNA.
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)
rubitecan (CHEBI:90225) has role antineoplastic agent (CHEBI:35610)
rubitecan (CHEBI:90225) has role EC 5.99.1.2 (DNA topoisomerase) inhibitor (CHEBI:50276)
rubitecan (CHEBI:90225) has role prodrug (CHEBI:50266)
rubitecan (CHEBI:90225) is a C-nitro compound (CHEBI:35716)
rubitecan (CHEBI:90225) is a pyranoindolizinoquinoline (CHEBI:48626)
rubitecan (CHEBI:90225) is a semisynthetic derivative (CHEBI:72588)
rubitecan (CHEBI:90225) is a tertiary alcohol (CHEBI:26878)
rubitecan (CHEBI:90225) is a δ-lactone (CHEBI:18946)
IUPAC Name 
(4S)-4-ethyl-4-hydroxy-10-nitro-1H-pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14(4H,12H)-dione
INNs  Source
rubitecanChemIDplus
rubitecanumWHO MedNet
rubitecánWHO MedNet
rubitécanWHO MedNet
Synonyms  Source
RFS 2000ChemIDplus
9-nitrocamptothecinChemIDplus
9-nitro-(20S)-camptothecinChEBI
9-nitro-20(S)-camptothecinChemIDplus
9-NCChemIDplus
Brand Names  Source
CamptogenChemIDplus
OrathecinChemIDplus
Manual XrefsDatabases
RubitecanWikipedia
D04031KEGG DRUG
2411DrugCentral
Registry NumbersSources
Reaxys:5365063Reaxys
CAS:91421-42-0ChemIDplus
CAS:91421-42-0KEGG DRUG
Citations