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SML0181

S 17092

≥98% (HPLC)

Synonym(s):

(2S,3aS,7aS)-1-(((R,R)-2-Phenylcyclopropyl)carbonyl)-2-((thiazolidin-3-yl)carbonyl)octahydro-1H-indole, [(2S,3aS,7aS)-Octahydro-1-[[(1R,2R)-2-phenylcyclopropyl]carbonyl]-1H-indol-2-yl]-3-thiazolidinyl--methanone

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About This Item

Empirical Formula (Hill Notation):
C22H28N2O2S
CAS Number:
176797-26-5
Molecular Weight:
384.53
NACRES:
NA.77
PubChem Substance ID:
329825210
UNSPSC Code:
12352200
MDL number:
MFCD00948255
Assay:
≥98% (HPLC)
Form:
powder
Quality level:
100
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Quality Level

100

assay

≥98% (HPLC)

form

powder

optical activity

[α]/D -140 to -170° in dichloromethane

color

white to tan

solubility

DMSO: ≥10 mg/mL

storage temp.

2-8°C

SMILES string

O=C([C@@H]1C[C@@H]2CCCC[C@@H]2N1C(=O)[C@@H]3C[C@H]3c4ccccc4)N5CCSC5

InChI

1S/C22H28N2O2S/c25-21(18-13-17(18)15-6-2-1-3-7-15)24-19-9-5-4-8-16(19)12-20(24)22(26)23-10-11-27-14-23/h1-3,6-7,16-20H,4-5,8-14H2/t16-,17-,18+,19-,20-/m0/s1

InChI key

NXSXRIHXEQSYEZ-KNJMJIDISA-N

Application

S 17092 may be used in prolyl endopeptidase-mediated cell signaling studies.

Biochem/physiol Actions

Potent selective inhibitor of Prolyl oligopeptidase (POP), also known as prolyl endopeptidase (PEP or PE). Nootropic.
S-17092 is a potent, selective inhibitor of Prolyl oligopeptidase (POP), also known as prolyl endopeptidase (PEP or PE). Ki=1.5 nM. Nootropic.

S-17092 inhibition of POP prevents breakdown and thus increases the activity of a number of neuropeptides, which is likely the basis for its nootropic activity. S 17092 has been shown to improve cognition. It improved cognitive task performance in chronic low dose MPTP-treated monkeys. S-17092 was recently used to inhibit the formation of AcSDKP from its precursor 43-mer thymosin ?4 (T?4). Ac-SDKP is involved in hemopoietic stem cell differentiation, is pro-angiogenic and antifibrogenic.

Features and Benefits

This compound is featured on the Neuropeptidases page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

pictograms

Exclamation mark
GHS07

signalword

Warning

hcodes

H302

Hazard Classifications

Acute Tox. 4 Oral

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
0000219878
0000219878
0000137292
0000078573
0000054448

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Articles

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Tommi P Kilpeläinen et al.
Biomedicine & pharmacotherapy = Biomedecine & pharmacotherapie, 128, 110253-110253 (2020-05-25)
Previous studies have shown that prolyl oligopeptidase (PREP) negatively regulates autophagy and increases the aggregation of alpha-synuclein (αSyn), linking it to the pathophysiology of Parkinson's disease. Our earlier results have revealed that the potent small molecular PREP inhibitor KYP-2047 is
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Kim JD, Toda C, D'Agostino G, et al.
Proceedings of the National Academy of Sciences of the USA, 111(32), 11876-11881 (2014)

Global Trade Item Number

SKUGTIN
SML0181-5MG04061832982311