CHEBI:74921 - L-685,458

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ChEBI Name L-685,458
ChEBI ID CHEBI:74921
Definition A 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.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula C39H52N4O6
Net Charge 0
Average Mass 672.85340
Monoisotopic Mass 672.38869
InChI InChI=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
InChIKey MURCDOXDAHPNRQ-ZJKZPDEISA-N
SMILES CC(C)C[C@H](NC(=O)[C@@H](C[C@@H](O)[C@H](Cc1ccccc1)NC(=O)OC(C)(C)C)Cc1ccccc1)C(=O)N[C@@H](Cc1ccccc1)C(N)=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): 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).
View more via ChEBI Ontology
ChEBI Ontology
Outgoing 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 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 Sources
(1S,2R,4R)-{1-benzyl-4-[1-(1S)-carbamoyl-(2-phenylethylcarbamoyl)-(1S)-3-methylbutylcarbamoyl]-2-hydroxy-5-phenylpentyl}carbamic acid tert-butyl ester ChEBI
(5S)-[tert-butoxycarbonylamino-6-phenyl-(4R)-hydroxy-(2R)-benzylhexanoyl]-L-Leu-L-Phe-NH2 ChEBI
L-685458 ChEBI
{(1S)-benzyl-(4R)-[1-((1S)-carbamoyl-2-phenyl-ethylcarbamoyl)-(1S)-3-methyl-butyl-carbamoyl]-(2R)-hydroxy-5-phenyl-pentyl} carbamic acid tert-butyl ester ChEBI
{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 ester ChEBI
Registry Number Type Source
8816919 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
10801983 PubMed citation Europe PMC
10864326 PubMed citation Europe PMC
10913280 PubMed citation Europe PMC
Last Modified
06 March 2014
General Comment
2013-07-25 For a stereocontrolled synthesis, see Nadin, A. et al., Tetrahedron, 2001, 57, 1861-1864.