CHEBI:177413 - plinabulin

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ChEBI Name plinabulin
ChEBI ID CHEBI:177413
Definition A member of the class of 2,5-diketopiperazines that is piperazine-2,5-dione substituted by benzylidene and (5-tert-butyl-1H-imidazol-4-yl)methylidene groups at positions 3 and 6, respectively. It is a vascular disrupting agent and a microtubule destabalising agent which was in clinical trials (now discontinued) for the treatment of non-small cell lung cancer.
Stars This entity has been manually annotated by the ChEBI Team.
Submitter MetaboLights
Supplier Information
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Formula C19H20N4O2
Net Charge 0
Average Mass 336.395
Monoisotopic Mass 336.15863
InChI InChI=1S/C19H20N4O2/c1-19(2,3)16-13(20-11-21-16)10-15-18(25)22-14(17(24)23-15)9-12-7-5-4-6-8-12/h4-11H,1-3H3,(H,20,21)(H,22,25)(H,23,24)/b14-9-,15-10-
InChIKey UNRCMCRRFYFGFX-TYPNBTCFSA-N
SMILES CC(C)(C)C1=C(\C=C2/NC(=O)\C(NC2=O)=C\C2=CC=CC=C2)N=CN1
Metabolite of Species Details
Sus scrofa (NCBI:txid9823) Found in sausage (ENVO:00002166). See: MetaboLights Study
Roles Classification
Chemical Role(s): Bronsted base
A molecular entity capable of accepting a hydron from a donor (Bronsted acid).
(via organic amino compound )
Biological Role(s): microtubule-destabilising agent
Any substance that interacts with tubulin to inhibit polymerisation of microtubules.
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.
angiogenesis inhibitor
An agent and endogenous substances that antagonize or inhibit the development of new blood vessels.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing plinabulin (CHEBI:177413) has role angiogenesis inhibitor (CHEBI:48422)
plinabulin (CHEBI:177413) has role antineoplastic agent (CHEBI:35610)
plinabulin (CHEBI:177413) has role apoptosis inducer (CHEBI:68495)
plinabulin (CHEBI:177413) has role microtubule-destabilising agent (CHEBI:61951)
plinabulin (CHEBI:177413) is a 2,5-diketopiperazines (CHEBI:65061)
plinabulin (CHEBI:177413) is a benzenes (CHEBI:22712)
plinabulin (CHEBI:177413) is a imidazoles (CHEBI:24780)
plinabulin (CHEBI:177413) is a olefinic compound (CHEBI:78840)
IUPAC Name
(3Z,6Z)-3-benzylidene-6-[(5-tert-butyl-1H-imidazol-4-yl)methylidene]piperazine-2,5-dione
INNs Sources
plinabulin WHO MedNet
plinabulina WHO MedNet
plinabuline WHO MedNet
plinabulinum WHO MedNet
Synonyms Sources
BPI 2358 ChEBI
BPI-2358 ChEBI
NPI 2358 ChemIDplus
NPI-2358 ChemIDplus
NPI2358 ChEBI
Manual Xrefs Databases
8125252 ChemSpider
D09655 KEGG DRUG
DB05992 DrugBank
LSM-43250 LINCS
Plinabulin Wikipedia
PN6 PDBeChem
View more database links
Registry Number Type Source
714272-27-2 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
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Last Modified
08 June 2022