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CHEBI:64530 - brevianamide F

Default Structure
ChEBI IDCHEBI:64530
ChEBI Namebrevianamide F
Stars
DefinitionA pyrrolopyrazine that is hexahydropyrrolo[1,2-a]pyrazine-1,4-dione bearing an indol-3-ylmethyl substituent at position 3 (the 3S,8aS-diastereomer, obtained by formal cyclocondensation of L-tryptophan and L-proline).
Last Modified8 May 2013
SubmitterSteve
DownloadsMolfile
FormulaC16H17N3O2
Net Charge0
Average Mass283.331
Monoisotopic Mass283.13208
SMILES[H][C@@]12CCCN1C(=O)[C@H](Cc1cnc3ccccc13)NC2=O
InChIInChI=1S/C16H17N3O2/c20-15-14-6-3-7-19(14)16(21)13(18-15)8-10-9-17-12-5-2-1-4-11(10)12/h1-2,4-5,9,13-14,17H,3,6-8H2,(H,18,20)/t13-,14-/m0/s1
InChIKeyRYFZBPVMVYTEKZ-KBPBESRZSA-N
Roles Classification
Chemical Role:
Bronsted base  A molecular entity capable of accepting a hydron from a donor (Brønsted acid).
Biological Role:
metabolite  Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
ChEBI Ontology
Outgoing Relation(s)
brevianamide F (CHEBI:64530) has role metabolite (CHEBI:25212)
brevianamide F (CHEBI:64530) is a dipeptide (CHEBI:46761)
brevianamide F (CHEBI:64530) is a indoles (CHEBI:24828)
brevianamide F (CHEBI:64530) is a pyrrolopyrazine (CHEBI:48337)
Incoming Relation(s)
18-oxotryprostatin A (CHEBI:66842) has functional parent brevianamide F (CHEBI:64530)
6-hydroxytryprostatin B (CHEBI:72762) has functional parent brevianamide F (CHEBI:64530)
deoxybrevianamide E (CHEBI:72948) has functional parent brevianamide F (CHEBI:64530)
tryprostatin A (CHEBI:72761) has functional parent brevianamide F (CHEBI:64530)
tryprostatin B (CHEBI:72760) has functional parent brevianamide F (CHEBI:64530)
IUPAC Name 
(3S,8aS)-3-(1H-indol-3-ylmethyl)hexahydropyrrolo[1,2-a]pyrazine-1,4-dione
Synonyms  Source
cyclo-L-Trp-L-ProChEBI
cyclo-L-tryptophanyl-L-prolineChEBI
cyclo-(Trp-Pro)ChEBI
L-prolyl-L-tryptophan anhydrideChEBI
L-tryptophyl-L-proline cyclic anhydrideChEBI
tryptophan-proline diketopiperazineChEBI
UniProt Name  Source
brevianamide FUniProt
Registry NumbersSources
Reaxys:625131Reaxys
CAS:38136-70-8ChemIDplus
Citations