CHEBI:90904 - asperlicin C

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ChEBI Name asperlicin C
ChEBI ID CHEBI:90904
Definition A member of the class of asperlicins in which the core 6,7-dihydroquinazolino[3,2-a][1,4]benzodiazepine-5,13-dione skeleton is substituted at the 7 pro-S position by an indol-3-ylmethyl group. It is a cholecystokinin antagonist.
Stars This entity has been manually annotated by the ChEBI Team.
Submitter Kristian Axelsen
Supplier Information
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Formula C25H18N4O2
Net Charge 0
Average Mass 406.437
Monoisotopic Mass 406.14298
InChI InChI=1S/C25H18N4O2/c30-24-18-9-3-6-12-22(18)29-23(27-20-11-5-2-8-17(20)25(29)31)21(28-24)13-15-14-26-19-10-4-1-7-16(15)19/h1-12,14,21,26H,13H2,(H,28,30)/t21-/m0/s1
InChIKey BUTFEAMXSRJHIM-NRFANRHFSA-N
SMILES C=1C=CC2=C(C1)C(N3C=4C=CC=CC4C(N[C@H](C3=N2)CC=5C=6C=CC=CC6NC5)=O)=O
Metabolite of Species Details
Aspergillus alliaceus (NCBI:txid209559) of strain ATCC20655 and 20656 See: PubMed
Roles Classification
Biological Role(s): cholecystokinin antagonist
A hormone antagonist that inhibits the action of the peptide hormone cholecystokinin.
Aspergillus metabolite
Any fungal metabolite produced during a metabolic reaction in the mould, Aspergillus .
metabolite
Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
(via alkaloid )
Application(s): cholecystokinin antagonist
A hormone antagonist that inhibits the action of the peptide hormone cholecystokinin.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing asperlicin C (CHEBI:90904) has role Aspergillus metabolite (CHEBI:76956)
asperlicin C (CHEBI:90904) has role cholecystokinin antagonist (CHEBI:73296)
asperlicin C (CHEBI:90904) is a asperlicins (CHEBI:91003)
asperlicin C (CHEBI:90904) is a indoles (CHEBI:24828)
asperlicin C (CHEBI:90904) is a organic heterotetracyclic compound (CHEBI:38163)
IUPAC Name
(7S)-7-(1H-indol-3-ylmethyl)-6,7-dihydroquinazolino[3,2-a][1,4]benzodiazepine-5,13-dione
Synonyms Sources
(−)-asperlicin C ChEBI
asperlicin C UniProt
Manual Xref Database
CPD-17021 MetaCyc
View more database links
Registry Numbers Types Sources
8016853 Reaxys Registry Number Reaxys
93413-06-0 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
19137180 PubMed citation Europe PMC
20066279 PubMed citation Europe PMC
23030663 PubMed citation SUBMITTER
3417561 PubMed citation Europe PMC
3417562 PubMed citation Europe PMC
Last Modified
27 January 2016
General Comment
2016-01-27 For an enantioselective total synthesis, see P.-Q. Huang et al., Tetrahedron Letters, 2015, 56, 1255-1258.