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216758-20-2

216758-20-2 Structure

216758-20-2 Structure
IdentificationBack Directory
[Name]

N-(5-ADAMANTANE-1-YL-METHOXY)-PENTYL-DEOXYNOJIRIMYCIN
[CAS]

216758-20-2
[Synonyms]

AMP-DEOXYNOJIRIMYCIN
ADAMANTANE-PENTYL-DNM
AMP-Deoxynojirimycin Exclusive
AMP-Deoxynojirimycin - Solution in ethanol
N-(5-AdaMant-1-yl-Methoxy)pentyl DeoxynojiriMycin
N-(5-ADAMANTANE-1-YL-METHOXY)-PENTYL-DEOXYNOJIRIMYCIN
2R-(HYDROXYMETHYL)-1-[5-(TRICYCLO[3.3.2.13,7]DEC-1-YLMETHOXY)PENTYL]-3R,4R,5S-PIPERIDINETRIOL
3,4,5-Piperidinetriol, 2-(hydroxymethyl)-1-[5-(tricyclo[3.3.1.13,7]dec-1-ylmethoxy)pentyl]-, (2R,3R,4R,5S)-
[Molecular Formula]

C22H39NO5
[MDL Number]

MFCD01863330
[MOL File]

216758-20-2.mol
[Molecular Weight]

397.55
Chemical PropertiesBack Directory
[Boiling point ]

569.9±50.0 °C(Predicted)
[density ]

1.214±0.06 g/cm3(Predicted)
[storage temp. ]

Store at -20°C
[solubility ]

DMF: 50 mg/ml; DMSO: 50 mg/ml; Ethanol: 30 mg/ml; Ethanol:PBS(pH 7.2) (1:1): 0.5 mg/ml
[form ]

powder
[pka]

13.72±0.70(Predicted)
[color ]

white to beige
[InChI]

1S/C22H39NO5/c24-13-18-20(26)21(27)19(25)12-23(18)4-2-1-3-5-28-14-22-9-15-6-16(10-22)8-17(7-15)11-22/h15-21,24-27H,1-14H2/t15-,16+,17-,18-,19+,20-,21-,22?/m1/s1
[InChIKey]

XVYLNHVEAOOEGI-OIPNBASOSA-N
[SMILES]

O[C@@H]1[C@H](N(C[C@@H]([C@H]1O)O)CCCCCOCC2(C3)C[C@@H](C4)C[C@H]3C[C@@H]4C2)CO
Safety DataBack Directory
[Symbol(GHS) ]

GHS hazard pictogramsGHS hazard pictograms
GHS02,GHS07
[Signal word ]

Danger
[Hazard statements ]

H225-H319
[Precautionary statements ]

P210-P233-P240-P241-P242-P243-P264-P280-P303+P361+P353-P305+P351+P338-P337+P313-P370+P378-P403+P235-P501
[WGK Germany ]

WGK 3
[Storage Class]

11 - Combustible Solids
Hazard InformationBack Directory
[Chemical Properties]

Off White Foam
[Uses]

A powerful inhibitor of the non-lysomal glucoceramidase at nanomolar concentrations. At these low concentrations, the lysosomal glucocerebrosidase and a-glucosidase, the glucoceramide synthetase, and the N-linked glycantrimming a-glucosidases of the endoplasmic reticulum are not affected.
[Biological Activity]

AMP-deoxynojirimycin (AMP-DNM) is an orally available iminosugar th at acts as a reversiblepotent and selective inhibitor against the non-lysosomal glucosylceramidase GBA2 (IC50 = 1.7 nM) over the glucosylceramide synthase (GCSUGCG)ER alpha-glucosidasesthe lysosomal glucocerebrosidase GBA (IC50 = 0.16 μM) and alpha-glucosidase GAA (IC50 = 0.87 μM). AMP-DNM selectively inhibits cellular GBA2 in cultures (GBA2/GBA IC50 = 0.3 nM/100 nM; human melanoma cells) and exhibits in vivo therapeutic efficacy in murine models of obesity (100 mg/kg/day p.o.) and colitis (10-50 mg/kg/day via i.p. or 1.25-6.25g/kg chow).
Spectrum DetailBack Directory
[Spectrum Detail]

N-(5-ADAMANTANE-1-YL-METHOXY)-PENTYL-DEOXYNOJIRIMYCIN(216758-20-2)1HNMR
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