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CHEBI:74921 - L-685,458

Default Structure
ChEBI IDCHEBI:74921
ChEBI NameL-685,458
Stars
DefinitionA peptide and carboxamide that is L-leucyl-L-phenylalaninamide, L-Leu-L-Phe-NH2, which has been acylated on the N-terminus by a Phe-Phe hydroxyethylene dipeptide isotere, 2R-benzyl-5S-tert-butoxycarbonylamino-4R-hydroxy-6-phenylhexanoic acid. Compounds based on the structure of L-685,458 are potent inhibitors of γ-secretase, which mediates the final catalytic step that generates the amyloid β-peptide (Aβ), which assembles into the neurotoxic aggregates in the brains of sufferers of Alzheimer's disease.
Last Modified6 March 2014
SubmitterGareth Owen
DownloadsMolfile
FormulaC39H52N4O6
Net Charge0
Average Mass672.867
Monoisotopic Mass672.38869
SMILESCC(C)C[C@H](NC(=O)[C@H](Cc1ccccc1)C[C@@H](O)[C@H](Cc1ccccc1)NC(=O)OC(C)(C)C)C(=O)N[C@@H](Cc1ccccc1)C(N)=O
InChIInChI=1S/C39H52N4O6/c1-26(2)21-33(37(47)41-32(35(40)45)24-29-19-13-8-14-20-29)42-36(46)30(22-27-15-9-6-10-16-27)25-34(44)31(23-28-17-11-7-12-18-28)43-38(48)49-39(3,4)5/h6-20,26,30-34,44H,21-25H2,1-5H3,(H2,40,45)(H,41,47)(H,42,46)(H,43,48)/t30-,31+,32+,33+,34-/m1/s1
InChIKeyMURCDOXDAHPNRQ-ZJKZPDEISA-N
Roles Classification
Chemical Role:
Bronsted base  A molecular entity capable of accepting a hydron from a donor (Brønsted acid).
Biological Roles:
peptidomimetic  A small protein-like chain designed to mimic a peptide.
EC 3.4.23.46 (memapsin 2) inhibitor  An EC 3.4.23.* (aspartic endopeptidase) inhibitor that interferes with the activity of memapsin 2 (EC 3.4.23.46).
ChEBI Ontology
Outgoing Relation(s)
L-685,458 (CHEBI:74921) has part tert-butoxycarbonyl group (CHEBI:48502)
L-685,458 (CHEBI:74921) has role EC 3.4.23.46 (memapsin 2) inhibitor (CHEBI:74925)
L-685,458 (CHEBI:74921) has role peptidomimetic (CHEBI:63175)
L-685,458 (CHEBI:74921) is a carbamate ester (CHEBI:23003)
L-685,458 (CHEBI:74921) is a monocarboxylic acid amide (CHEBI:29347)
L-685,458 (CHEBI:74921) is a peptide (CHEBI:16670)
L-685,458 (CHEBI:74921) is a secondary alcohol (CHEBI:35681)
Incoming Relation(s)
GCB (CHEBI:74858) has functional parent L-685,458 (CHEBI:74921)
IUPAC Name 
N-{(2R,4R,5S)-2-benzyl-5-[(tert-butoxycarbonyl)amino]-4-hydroxy-6-phenylhexanoyl}-L-leucyl-L-phenylalaninamide
Synonyms  Source
(1S,2R,4R)-{1-benzyl-4-[1-(1S)-carbamoyl-(2-phenylethylcarbamoyl)-(1S)-3-methylbutylcarbamoyl]-2-hydroxy-5-phenylpentyl}carbamic acid tert-butyl esterChEBI
{(1S)-benzyl-(4R)-[1-((1S)-carbamoyl-2-phenyl-ethylcarbamoyl)-(1S)-3-methyl-butyl-carbamoyl]-(2R)-hydroxy-5-phenyl-pentyl} carbamic acid tert-butyl esterChEBI
{1(S)-benzyl-4(R)-[1-(1(S)-carbamoyl-2-phenylethylcarbamoyl)-1(S)-3-methyl-butylcarbamoyl]-2(R)-hydroxy-5-phenylpentyl}carbamic acid tert-butyl esterChEBI
(5S)-[tert-butoxycarbonylamino-6-phenyl-(4R)-hydroxy-(2R)-benzylhexanoyl]-L-Leu-L-Phe-NH2ChEBI
L-685458ChEBI
Registry NumbersSources
Reaxys:8816919Reaxys
Citations