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CHEBI:156292 - tilivalline

Default Structure
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)
Klebsiella pneumoniae (ncbitaxon:573) - PubMed (11672297)
Xenorhabdus eapokensis (ncbitaxon:1873482) - PubMed (29596433)
Roles Classification
Biological Roles:
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.
toxin  Poisonous substance produced by a biological organism such as a microbe, animal or plant.
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
(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
epitilivallineChemIDplus
Registry NumbersSources
CAS:80279-24-9ChemIDplus
Citations