Home Carbonyls L-Phenylalaninamide, N-[(2R,4R,5S)-5-[[(1,1-dimethylethoxy)carbonyl]amino]-4-hydroxy-1-oxo-6-phenyl-2-(phenylmethyl)hexyl]-L-leucyl-

L-Phenylalaninamide, N-[(2R,4R,5S)-5-[[(1,1-dimethylethoxy)carbonyl]amino]-4-hydroxy-1-oxo-6-phenyl-2-(phenylmethyl)hexyl]-L-leucyl-

CAS No.:
292632-98-5
Catalog Number:
AG002XWC
Molecular Formula:
C39H52N4O6
Molecular Weight:
672.8534
Pack Size
Purity
Availability
Location
Price(USD)
Quantity
  
1mg
99%
1 week
United States
$290
- +
5mg
99%
1 week
United States
$790
- +
10mg
99%
1 week
United States
$1457
- +
Product Description
Catalog Number:
AG002XWC
Chemical Name:
L-Phenylalaninamide, N-[(2R,4R,5S)-5-[[(1,1-dimethylethoxy)carbonyl]amino]-4-hydroxy-1-oxo-6-phenyl-2-(phenylmethyl)hexyl]-L-leucyl-
CAS Number:
292632-98-5
Molecular Formula:
C39H52N4O6
Molecular Weight:
672.8534
MDL Number:
MFCD03093402
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
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
InChI Key:
MURCDOXDAHPNRQ-ZJKZPDEISA-N
SMILES:
CC(C[C@@H](C(=O)N[C@H](C(=O)N)Cc1ccccc1)NC(=O)[C@@H](C[C@H]([C@@H](NC(=O)OC(C)(C)C)Cc1ccccc1)O)Cc1ccccc1)C
Properties
Complexity:
1030  
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
5  
Defined Bond Stereocenter Count:
0
Exact Mass:
672.389g/mol
Formal Charge:
0
Heavy Atom Count:
49  
Hydrogen Bond Acceptor Count:
6  
Hydrogen Bond Donor Count:
5  
Isotope Atom Count:
0
Molecular Weight:
672.867g/mol
Monoisotopic Mass:
672.389g/mol
Rotatable Bond Count:
19  
Topological Polar Surface Area:
160A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
5.9  
Literature
Title Journal
Biological significance and therapeutic implication of resveratrol-inhibited Wnt, Notch and STAT3 signaling in cervical cancer cells. Genes & cancer 20140501
Dopamine induces apoptosis in APPswe-expressing Neuro2A cells following Pepstatin-sensitive proteolysis of APP in acid compartments. Brain research 20120830
Development of clickable active site-directed photoaffinity probes for γ-secretase. Bioorganic & medicinal chemistry letters 20120415
First and second generation γ-secretase modulators (GSMs) modulate amyloid-β (Aβ) peptide production through different mechanisms. The Journal of biological chemistry 20120406
Inhibition of the Notch-Hey1 axis blocks embryonal rhabdomyosarcoma tumorigenesis. Clinical cancer research : an official journal of the American Association for Cancer Research 20111201
Presenilin-1 regulates neural progenitor cell differentiation in the adult brain. The Journal of neuroscience : the official journal of the Society for Neuroscience 20110216
Surface expression and limited proteolysis of ADAM10 are increased by a dominant negative inhibitor of dynamin. BMC cell biology 20110101
Characterization of a Drosophila Alzheimer's disease model: pharmacological rescue of cognitive defects. PloS one 20110101
Human ROBO1 is cleaved by metalloproteinases and gamma-secretase and migrates to the nucleus in cancer cells. FEBS letters 20100702
Design, synthesis, and biological evaluation of a novel class of gamma-secretase modulators with PPARgamma activity. Journal of medicinal chemistry 20100624
A GPCR/secretase complex regulates beta- and gamma-secretase specificity for Abeta production and contributes to AD pathogenesis. Cell research 20100201
Recent advances in the identification of gamma-secretase inhibitors to clinically test the Abeta oligomer hypothesis of Alzheimer's disease. Journal of medicinal chemistry 20091022
Nitrous oxide plus isoflurane induces apoptosis and increases beta-amyloid protein levels. Anesthesiology 20091001
The common inhalational anesthetic sevoflurane induces apoptosis and increases beta-amyloid protein levels. Archives of neurology 20090501
Nutlin-3 up-regulates the expression of Notch1 in both myeloid and lymphoid leukemic cells, as part of a negative feedback antiapoptotic mechanism. Blood 20090430
Plasmodium falciparum signal peptide peptidase is a promising drug target against blood stage malaria. Biochemical and biophysical research communications 20090313
Suppression of Notch signaling in the neonatal mouse ovary decreases primordial follicle formation. Endocrinology 20090201
The cytotoxicity of gamma-secretase inhibitor I to breast cancer cells is mediated by proteasome inhibition, not by gamma-secretase inhibition. Breast cancer research : BCR 20090101
The inhalation anesthetic desflurane induces caspase activation and increases amyloid beta-protein levels under hypoxic conditions. The Journal of biological chemistry 20080502
In vitro validation of gamma-secretase inhibitors alone or in combination with other anti-cancer drugs for the treatment of T-cell acute lymphoblastic leukemia. Haematologica 20080401
Identification of gamma-secretase inhibitor potency determinants on presenilin. The Journal of biological chemistry 20080201
Abeta46 is processed to Abeta40 and Abeta43, but not to Abeta42, in the low density membrane domains. The Journal of biological chemistry 20080111
Signal peptide peptidase and gamma-secretase share equivalent inhibitor binding pharmacology. The Journal of biological chemistry 20071221
Gamma-secretase inhibitors exerts antitumor activity via down-regulation of Notch and Nuclear factor kappa B in human tongue carcinoma cells. Oral diseases 20071101
Insensitivity to Abeta42-lowering nonsteroidal anti-inflammatory drugs and gamma-secretase inhibitors is common among aggressive presenilin-1 mutations. The Journal of biological chemistry 20070824
The same gamma-secretase accounts for the multiple intramembrane cleavages of APP. Journal of neurochemistry 20070301
Novel processing of Notch 1 within its intracellular domain by a cysteine protease. Neuro-degenerative diseases 20070101
A novel tricyclic pyrone compound ameliorates cell death associated with intracellular amyloid-beta oligomeric complexes. Journal of neurochemistry 20060701
C-terminal fragment of presenilin is the molecular target of a dipeptidic gamma-secretase-specific inhibitor DAPT (N-[N-(3,5-difluorophenacetyl)-L-alanyl]-S-phenylglycine t-butyl ester). The Journal of biological chemistry 20060526
Up-regulation of the Notch ligand Delta-like 4 inhibits VEGF-induced endothelial cell function. Blood 20060201
A presenilin-independent aspartyl protease prefers the gamma-42 site cleavage. Journal of neurochemistry 20060101
Eosinophilic differentiation is promoted by blockage of Notch signaling with a gamma-secretase inhibitor. European journal of immunology 20051001
Cell-autonomous notch signaling regulates endothelial cell branching and proliferation during vascular tubulogenesis. FASEB journal : official publication of the Federation of American Societies for Experimental Biology 20050601
Inhibition of angiogenesis and tumor growth by beta and gamma-secretase inhibitors. European journal of pharmacology 20050502
Transition-state analogue gamma-secretase inhibitors stabilize a 900 kDa presenilin/nicastrin complex. Biochemistry 20050322
Presenilin-dependent processing and nuclear function of gamma-protocadherins. The Journal of biological chemistry 20050311
Presenilin attenuates receptor-mediated signaling and synaptic function. The Journal of neuroscience : the official journal of the Society for Neuroscience 20050209
Stereoselective synthesis of photoreactive peptidomimetic gamma-secretase inhibitors. The Journal of organic chemistry 20041015
PEN-2 enhances gamma-cleavage after presenilin heterodimer formation. Journal of neurochemistry 20040901
JLK isocoumarin inhibitors: selective gamma-secretase inhibitors that do not interfere with notch pathway in vitro or in vivo. Journal of neuroscience research 20031101
The mechanism of gamma-secretase: multiple inhibitor binding sites for transition state analogs and small molecule inhibitors. The Journal of biological chemistry 20030801
Catalytic site-directed gamma-secretase complex inhibitors do not discriminate pharmacologically between Notch S3 and beta-APP cleavages. Biochemistry 20030624
Presenilin-dependent gamma-secretase activity mediates the intramembranous cleavage of CD44. Oncogene 20030313
Distinct mechanisms by mutant presenilin 1 and 2 leading to increased intracellular levels of amyloid beta-protein 42 in Chinese hamster ovary cells. Biochemistry 20030204
Synthesis and gamma-secretase activity of APP substrate-based hydroxyethylene dipeptide isosteres. Bioorganic & medicinal chemistry letters 20030106
Presenilin-dependent intramembrane proteolysis of CD44 leads to the liberation of its intracellular domain and the secretion of an Abeta-like peptide. The Journal of biological chemistry 20021122
Linear non-competitive inhibition of solubilized human gamma-secretase by pepstatin A methylester, L685458, sulfonamides, and benzodiazepines. The Journal of biological chemistry 20020830
Presenilin-dependent gamma-secretase activity modulates neurite outgrowth. Neurobiology of disease 20020201
gamma-Secretase: characterization and implication for Alzheimer disease therapy. Neurobiology of aging 20020101
gamma -Secretase cleavage and nuclear localization of ErbB-4 receptor tyrosine kinase. Science (New York, N.Y.) 20011207
Gamma-secretase: a catalyst of Alzheimer disease and signal transduction. Molecular interventions 20011001
Endoproteolysis of the ER stress transducer ATF6 in the presence of functionally inactive presenilins. Neurobiology of disease 20010801
Secretase targets for Alzheimer's disease: identification and therapeutic potential. Journal of medicinal chemistry 20010621
L-685,458, an aspartyl protease transition state mimic, is a potent inhibitor of amyloid beta-protein precursor gamma-secretase activity. Biochemistry 20000801
Properties