Record Information
Version1.0
StatusDetected and Quantified
Creation Date2021-05-15 10:18:34 UTC
Update Date2024-10-17 16:15:01 UTC
Metabolite IDMMDBc0020318
Metabolite Identification
Common NameBrevianamide F
Descriptionbrevianamide F, also known as cyclo-(TRP-pro), belongs to the class of organic compounds known as alpha amino acids and derivatives. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon), or a derivative thereof. brevianamide F is a moderately basic compound (based on its pKa). A pyrrolopyrazine that is hexahydropyrrolopyrazine-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).
Structure
Synonyms
ValueSource
Cyclo-(TRP-pro)ChEBI
Cyclo-L-TRP-L-proChEBI
Cyclo-L-tryptophanyl-L-prolineChEBI
L-Prolyl-L-tryptophan anhydrideChEBI
L-Tryptophyl-L-proline cyclic anhydrideChEBI
Tryptophan-proline diketopiperazineChEBI
Cyclo(L-TRP-L-pro)Kegg
Molecular FormulaC16H17N3O2
Average Mass283.3251
Monoisotopic Mass283.132076803
IUPAC Name(3S,8aS)-1-hydroxy-3-(1H-indol-3-ylmethyl)-3H,4H,6H,7H,8H,8aH-pyrrolo[1,2-a]pyrazin-4-one
Traditional Name(3S,8aS)-1-hydroxy-3-(1H-indol-3-ylmethyl)-3H,6H,7H,8H,8aH-pyrrolo[1,2-a]pyrazin-4-one
CAS Registry NumberNot Available
SMILES
[H][C@@]12CCCN1C(=O)[C@]([H])(CC1=CNC3=CC=CC=C13)N=C2O
InChI Identifier
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
InChI KeyRYFZBPVMVYTEKZ-KBPBESRZSA-N