CHEBI:90903 - asperlicin E

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ChEBI Name asperlicin E
ChEBI ID CHEBI:90903
Definition A member of the class of asperlicins that is asperlicin C in which the lactam nitrogen of the benzodiazepineone moiety has undergone addition to the 2-position of the 2-3 double bond of the indole moeity, and in which the hydrogen at the 3-position of the indole moiety has been replaced by a hydroxy group.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 C25H18N4O3
Net Charge 0
Average Mass 422.436
Monoisotopic Mass 422.13789
InChI InChI=1S/C25H18N4O3/c30-22-14-7-1-4-10-17(14)26-21-20-13-25(32)16-9-3-5-11-18(16)27-24(25)29(20)23(31)15-8-2-6-12-19(15)28(21)22/h1-12,20,24,27,32H,13H2/t20-,24+,25-/m0/s1
InChIKey HYHLSEUXMRFVND-AMDXRBSFSA-N
SMILES C12=C(C(N3[C@H](C=4N1C(C5=C(N4)C=CC=C5)=O)C[C@]6([C@@]3(NC=7C=CC=CC67)[H])O)=O)C=CC=C2
Metabolite of Species Details
Aspergillus alliaceus (NCBI:txid209559) of strain ATCC20655 and 20656 See: PubMed
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): 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 E (CHEBI:90903) has role Aspergillus metabolite (CHEBI:76956)
asperlicin E (CHEBI:90903) has role cholecystokinin antagonist (CHEBI:73296)
asperlicin E (CHEBI:90903) is a aminal (CHEBI:35412)
asperlicin E (CHEBI:90903) is a asperlicins (CHEBI:91003)
asperlicin E (CHEBI:90903) is a organic heteroheptacyclic compound (CHEBI:52157)
asperlicin E (CHEBI:90903) is a tertiary alcohol (CHEBI:26878)
IUPAC Name
(12aR,17bS,18aS)-17b-hydroxy-13,17b,18,18a-tetrahydro-11H-indolo[3',2':4,5]pyrrolo[2,1-c]quinazolino[3,2-a][1,4]benzodiazepine-5,11(12aH)-dione
Synonyms Sources
(+)-asperlicin E ChEBI
asperlicin E UniProt
Manual Xref Database
CPD-17023 MetaCyc
View more database links
Registry Numbers Types Sources
23125539 Reaxys Registry Number Reaxys
93413-05-9 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
16323862 PubMed citation Europe PMC
23030663 PubMed citation SUBMITTER
25180619 PubMed citation Europe PMC
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.