L-685,458 - ≥98% , CAS No.292632-98-5

CAS: 292632-98-5 Cat. No.: L275059 Molecular Weight: 672.85

GRADE & PURITY ≥98%

Synonyms

NCGC00165962-01 | HY-19369 | L 458 | (5S)-[tert-butoxycarbonylamino-6-phenyl-(4R)-hydroxy-(2R)-benzylhexanoyl]-L-Leu-L-Phe-NH2 | CHEBI:74921 | L-68458 | BCP22749 | tert-butyl ((2S,3R,5R)-6-(((S)-1-(((S)-1-amino-1-oxo-3-phenylpropan-2-yl)amino)-4-methyl-1-

Storage

Store at -20°C,Desiccated

Shipped In

Ice chest + Ice pads

Overview

Store at -20°C (desiccating conditions).

application

L-685,458 has been used to attenuate Notch signalling in ovary culture. It has also been used to analyze the specificity of the γ-secretase activity in brain tissue samples.

Specifications

Synonyms

NCGC00165962-01 | HY-19369 | L 458 | (5S)-[tert-butoxycarbonylamino-6-phenyl-(4R)-hydroxy-(2R)-benzylhexanoyl]-L-Leu-L-Phe-NH2 | CHEBI:74921 | L-68458 | BCP22749 | tert-butyl ((2S, 3R, 5R)-6-(((S)-1-(((S)-1-amino-1-oxo-3-phenylpropan-2-yl)amino)-4-methyl-1-

Specifications & Purity

≥98%

Biochemical and Physiological Mechanisms

Potent, selective and non-competitive γ-secretase inhibitor (IC 50 = 17 nM). Shows 50-fold selectivity over a range of aspartyl, serine and cysteine proteases. Inhibits Aβ40 and Aβ42 peptides (IC 50 values are 48 and 67 nM respectively). Active in vivo.

Storage

Store at -20°C, Desiccated

Shipped In

Ice chest + Ice pads

This product requires cold chain shipping. Ground and other economy services are not available.

Note

Wherever possible, you should prepare and use solutions on the same day. However, if you need to make up stock solutions in advance, we recommend that you store the solution as aliquots in tightly sealed vials at -20°C. Generally, these will be useable for up to one month. Before use, and prior to opening the vial we recommend that you allow your product to equilibrate to room temperature for at least 1 hour. Need more advice on solubility, usage and handling? Please visit our frequently asked questions (FAQ) page for more details.

Purity

≥98%

Names and Identifiers

• Pubchem Sid: 504763867
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/504763867
• Canonical Smiles: CC(C)CC(C(=O)NC(CC1=CC=CC=C1)C(=O)N)NC(=O)C(CC2=CC=CC=C2)CC(C(CC3=CC=CC=C3)NC(=O)OC(C)(C)C)O
• IUPAC Name: tert-butyl N-[(2S,3R,5R)-6-[[(2S)-1-[[(2S)-1-amino-1-oxo-3-phenylpropan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]amino]-5-benzyl-3-hydroxy-6-oxo-1-phenylhexan-2-yl]carbamate
• InChIKey: MURCDOXDAHPNRQ-ZJKZPDEISA-N
• 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
• Isomeric SMILES: CC(C)C[C@@H](C(=O)N[C@@H](CC1=CC=CC=C1)C(=O)N)NC(=O)[C@H](CC2=CC=CC=C2)C[C@H]([C@H](CC3=CC=CC=C3)NC(=O)OC(C)(C)C)O
• Molecular Weight: 672.85
• Reaxy-Rn: 30052937
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=30052937&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organic acids and derivatives
    • Class Peptidomimetics
      • Subclass Hybrid peptides

• Kingdom: Organic compounds
• Superclass: Organic acids and derivatives
• Class: Peptidomimetics
• Subclass: Hybrid peptides
• Intermediate Tree Nodes: Not available
• Direct Parent: Hybrid peptides
• Alternative Parents: Dipeptides Phenylalanine and derivatives Leucine and derivatives N-acyl-alpha amino acids and derivatives Alpha amino acid amides Amphetamines and derivatives N-acyl amines Carbamate esters Organic carbonic acids and derivatives Secondary alcohols Secondary carboxylic acid amides Primary carboxylic acid amides Organopnictogen compounds Organonitrogen compounds Organic oxides Hydrocarbon derivatives Carbonyl compounds
• Molecular Framework: Aromatic homomonocyclic compounds
• Substituents: Hybrid peptide - Alpha-dipeptide - Phenylalanine or derivatives - Leucine or derivatives - N-acyl-alpha amino acid or derivatives - Alpha-amino acid amide - N-substituted-alpha-amino acid - Alpha-amino acid or derivatives - Amphetamine or derivatives - Monocyclic benzene moiety - Fatty acyl - Benzenoid - Fatty amide - N-acyl-amine - Carbamic acid ester - Carbonic acid derivative - Primary carboxylic acid amide - Secondary alcohol - Secondary carboxylic acid amide - Carboxamide group - Carboxylic acid derivative - Alcohol - Organonitrogen compound - Organooxygen compound - Carbonyl group - Hydrocarbon derivative - Organic oxide - Organopnictogen compound - Organic oxygen compound - Organic nitrogen compound - Aromatic homomonocyclic compound
• Description: This compound belongs to the class of organic compounds known as hybrid peptides. These are compounds containing at least two different types of amino acids (alpha, beta, gamma, delta) linked to each other through a peptide bond.
• External Descriptors: carbamate ester - monocarboxylic acid amide - secondary alcohol - peptide

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Associated Targets(Human)

PSENEN Tchem Gamma-secretase subunit PEN-2 (1 Activities)

Discover Target: PSENEN

Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

PSEN1 Tchem Presenilin 1 (302 Activities)

Discover Target: PSEN1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

PSENEN Tchem Gamma-secretase subunit PEN-2 (38 Activities)

Discover Target: PSENEN

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

MEN1 Tchem Menin/Histone-lysine N-methyltransferase MLL (48157 Activities)

Discover Target: MEN1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

APH1A Tbio Gamma-secretase (4915 Activities)

Discover Target: APH1A

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Associated Targets(non-human)

rep Replicase polyprotein 1ab (378 Activities)

Discover Target: rep

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Rorc Nuclear receptor ROR-gamma (89407 Activities)

Discover Target: Rorc

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Mechanisms of Action

Chemical and Physical Properties

• Solubility: Supplied in DMSO (1 mM),Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly)
• Melt Point(°C): 209-211°C
• Molecular Weight: 672.900 g/mol
• XLogP3: 5.900
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 19
• Exact Mass: 672.389 Da
• Monoisotopic Mass: 672.389 Da
• Topological Polar Surface Area: 160.000 Ų
• Heavy Atom Count: 49
• Formal Charge: 0
• Complexity: 1030.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 5
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1