brevianamide F (CHEBI:64530)

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ChEBI Name	brevianamide F

ChEBI ID	CHEBI:64530

Definition	A 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).

Stars	This entity has been manually annotated by the ChEBI Team.

Supplier Information

Download	Molfile XML SDF

Formula

C16H17N3O2

Net Charge

Average Mass

283.32510

Monoisotopic Mass

283.13208

InChI

InChI=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

InChIKey

RYFZBPVMVYTEKZ-KBPBESRZSA-N

SMILES

[H][C@@]12CCCN1C(=O)[C@H](Cc1c[nH]c3ccccc13)NC2=O

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):	metabolite Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.

ChEBI Ontology
Outgoing	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	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	Sources
brevianamide F	UniProt
cyclo-(Trp-Pro)	ChEBI
cyclo-L-Trp-L-Pro	ChEBI
cyclo-L-tryptophanyl-L-proline	ChEBI
L-prolyl-L-tryptophan anhydride	ChEBI
L-tryptophyl-L-proline cyclic anhydride	ChEBI
tryptophan-proline diketopiperazine	ChEBI

Last Modified

08 May 2013