CHEBI:66842 - 18-oxotryprostatin A

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ChEBI Name 18-oxotryprostatin A
ChEBI ID CHEBI:66842
Definition An indole alkaloid that is tryprostatin A substituted by an oxo substituent at position 18. Isolated from Aspergillus sydowii, it exhibits cytotoxicity.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula C22H25N3O4
Net Charge 0
Average Mass 395.45160
Monoisotopic Mass 395.18451
InChI InChI=1S/C22H25N3O4/c1-12(2)9-19(26)20-15(14-7-6-13(29-3)10-16(14)23-20)11-17-22(28)25-8-4-5-18(25)21(27)24-17/h6-7,9-10,17-18,23H,4-5,8,11H2,1-3H3,(H,24,27)/t17-,18-/m0/s1
InChIKey UJAJXFUZWQQKAG-ROUUACIJSA-N
SMILES [H][C@@]1(Cc2c([nH]c3cc(OC)ccc23)C(=O)C=C(C)C)NC(=O)[C@]2([H])CCCN2C1=O
Metabolite of Species Details
Aspergillus sydowii (NCBI:txid75750) of strain PFW 1-13 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): 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): antineoplastic agent
A substance that inhibits or prevents the proliferation of neoplasms.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing 18-oxotryprostatin A (CHEBI:66842) has functional parent brevianamide F (CHEBI:64530)
18-oxotryprostatin A (CHEBI:66842) has role Aspergillus metabolite (CHEBI:76956)
18-oxotryprostatin A (CHEBI:66842) has role antineoplastic agent (CHEBI:35610)
18-oxotryprostatin A (CHEBI:66842) is a aromatic ether (CHEBI:35618)
18-oxotryprostatin A (CHEBI:66842) is a aromatic ketone (CHEBI:76224)
18-oxotryprostatin A (CHEBI:66842) is a dipeptide (CHEBI:46761)
18-oxotryprostatin A (CHEBI:66842) is a enone (CHEBI:51689)
18-oxotryprostatin A (CHEBI:66842) is a indole alkaloid (CHEBI:38958)
18-oxotryprostatin A (CHEBI:66842) is a indoles (CHEBI:24828)
18-oxotryprostatin A (CHEBI:66842) is a pyrrolopyrazine (CHEBI:48337)
IUPAC Name
(3S,8aS)-3-{[6-methoxy-2-(3-methylbut-2-enoyl)-1H-indol-3-yl]methyl}hexahydropyrrolo[1,2-a]pyrazine-1,4-dione
Registry Number Type Source
18842461 Reaxys Registry Number Reaxys
Citation Waiting for Citations Type Source
18505285 PubMed citation Europe PMC
Last Modified
27 October 2016