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CHEBI:66842 - 18-oxotryprostatin A

ChEBI IDCHEBI:66842
ChEBI Name18-oxotryprostatin A
Stars
DefinitionAn indole alkaloid that is tryprostatin A substituted by an oxo substituent at position 18. Isolated from Aspergillus sydowii, it exhibits cytotoxicity.
Last Modified27 October 2016
DownloadsMolfile
FormulaC22H25N3O4
Net Charge0
Average Mass395.459
Monoisotopic Mass395.18451
SMILES[H][C@@]12CCCN1C(=O)[C@]([H])(Cc1c(C(=O)C=C(C)C)nc3cc(OC)ccc13)NC2=O
InChIInChI=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
InChIKeyUJAJXFUZWQQKAG-ROUUACIJSA-N
Species of MetaboliteComponentSourceComments
Aspergillus sydowii (ncbitaxon:75750) - PubMed (18505285) Strain: PFW 1-13
Roles Classification
Chemical Role:
Bronsted base  A molecular entity capable of accepting a hydron from a donor (Brønsted acid).
Biological Roles:
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.
Application:
antineoplastic agent  A substance that inhibits or prevents the proliferation of neoplasms.
ChEBI Ontology
Outgoing Relation(s)
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 NumbersSources
Reaxys:18842461Reaxys
Citations