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CHEBI:156292 - tilivalline

ChEBI IDCHEBI:156292
ChEBI Nametilivalline
Stars
DefinitionA pyrrolobenzodiazepine that is (11aS)-2,3,5,10,11,11a-hexahydro-1H-pyrrolo[2,1-c][1,4]benzodiazepine substituted by an oxo group at position 5, by a hydroxy group at position 9, and by a 1H-indol-3-yl group at position 11S. It is a natural product discovered in Klebsiella oxytoca which is the causative toxin in antibiotic associated hemorrhagic colitis. It exhibits a microtubule-stabilizing activity that leads to mitotic arrest in the host cells.
Last Modified13 August 2020
SubmitterMartin Larralde
DownloadsMolfile
FormulaC20H19N3O2
Net Charge0
Average Mass333.391
Monoisotopic Mass333.14773
SMILES[H][C@@]1(c2cnc3ccccc23)Nc2c(O)cccc2C(=O)N2CCC[C@]21[H]
InChIInChI=1S/C20H19N3O2/c24-17-9-3-6-13-19(17)22-18(16-8-4-10-23(16)20(13)25)14-11-21-15-7-2-1-5-12(14)15/h1-3,5-7,9,11,16,18,21-22,24H,4,8,10H2/t16-,18-/m0/s1
InChIKeyAJZNARCWDDMOPL-WMZOPIPTSA-N
Species of MetaboliteComponentSourceComments
Klebsiella oxytoca (ncbitaxon:571) - PubMed (29389112)
Xenorhabdus eapokensis (ncbitaxon:1873482) - PubMed (29596433)
Klebsiella pneumoniae (ncbitaxon:573) - PubMed (11672297)
Roles Classification
Biological Roles:
toxin  Poisonous substance produced by a biological organism such as a microbe, animal or plant.
bacterial metabolite  Any prokaryotic metabolite produced during a metabolic reaction in bacteria.
microtubule-stabilising agent  Any substance that interacts with tubulin to promote polymerisation of microtubules.
metabolite  Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
ChEBI Ontology
Outgoing Relation(s)
tilivalline (CHEBI:156292) has role bacterial metabolite (CHEBI:76969)
tilivalline (CHEBI:156292) has role microtubule-stabilising agent (CHEBI:61950)
tilivalline (CHEBI:156292) has role toxin (CHEBI:27026)
tilivalline (CHEBI:156292) is a indole alkaloid (CHEBI:38958)
tilivalline (CHEBI:156292) is a indoles (CHEBI:24828)
tilivalline (CHEBI:156292) is a phenols (CHEBI:33853)
tilivalline (CHEBI:156292) is a pyrrolobenzodiazepine (CHEBI:131437)
IUPAC Name 
(11S,11aS)-9-hydroxy-11-(1H-indol-3-yl)-1,2,3,10,11,11a-hexahydro-5H-pyrrolo[2,1-c][1,4]benzodiazepin-5-one
Synonyms  Source
epitilivallineChemIDplus
(7S,8S)-11-hydroxy-8-(1H-indol-3-yl)-3,9-diazatricyclo[8.4.0.03,7]tetradeca-1(10),11,13-trien-2-oneChEBI
Registry NumbersSources
CAS:80279-24-9ChemIDplus
Citations