CHEBI:156292 - tilivalline

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ChEBI Name tilivalline
ChEBI ID CHEBI:156292
Definition A 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.
Stars This entity has been manually annotated by the ChEBI Team.
Submitter Martin Larralde
Supplier Information
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Formula C20H19N3O2
Net Charge 0
Average Mass 333.391
Monoisotopic Mass 333.14773
InChI InChI=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
InChIKey AJZNARCWDDMOPL-WMZOPIPTSA-N
SMILES [H][C@@]12CCCN1C(=O)C1=C(N[C@@]2([H])C2=CNC3=CC=CC=C23)C(O)=CC=C1
Metabolite of Species Details
Xenorhabdus eapokensis (NCBI:txid1873482) See: PubMed
Klebsiella oxytoca (NCBI:txid571) See: PubMed
Klebsiella pneumoniae (NCBI:txid573) See: PubMed
Roles Classification
Biological Role(s): 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.
bacterial metabolite
Any prokaryotic metabolite produced during a metabolic reaction in bacteria.
metabolite
Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
(via alkaloid )
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ChEBI Ontology
Outgoing 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 Sources
(7S,8S)-11-hydroxy-8-(1H-indol-3-yl)-3,9-diazatricyclo[8.4.0.03,7]tetradeca-1(10),11,13-trien-2-one ChEBI
epitilivalline ChemIDplus
Registry Number Type Source
80279-24-9 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
11672297 PubMed citation Europe PMC
25057966 PubMed citation Europe PMC
25157164 PubMed citation SUBMITTER
28970173 PubMed citation Europe PMC
28972161 PubMed citation Europe PMC
28977734 PubMed citation SUBMITTER
29389112 PubMed citation SUBMITTER
29596433 PubMed citation Europe PMC
30808763 PubMed citation SUBMITTER
31717457 PubMed citation Europe PMC
7666357 PubMed citation Europe PMC
7710637 PubMed citation Europe PMC
Last Modified
13 August 2020