AMP-Deoxynojirimycin - A solution in ethanol , CAS No.216758-20-2

CAS: 216758-20-2 Cat. No.: A338640 Summenformel: C22H39NO5 Molekulargewicht: 397.6
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GRADE & PURITY A solution in ethanol
Synonyms
AMP-dNM
Storage
Store at -20°C
Shipped In
Ice chest + Ice pads
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Size
Deutschland (EU)
USA*
Price
Qty
1mg
A338640-1mg
Auf Bestellung · 8–12 Wochen
246,35€
500μg
A338640-500μg
Auf Bestellung · 8–12 Wochen
124,00€
Enter a quantity for the sizes you want to add.
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Why this grade

A solution in ethanol for sensitive chromatographic and analytical workflows requiring minimal baseline interference.

🌡

Storage & shipping

Store at -20°C Ships Ice chest + Ice pads Check lot-specific COA for exact specifications.

📋

Quality documents

SDS, COA, datasheet, and spec sheet available for download. Lot-specific COA accessible via lot number lookup.

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Literature proof

Cited in 0 peer-reviewed publications across chromatography, organic synthesis, and cross-coupling reactions.

Übersicht

AMP-Deoxynojirimycin (AMP-dNM) is a hydrophobic derivative of dNM that potently inhibits β-glucosidase 2 (BGD, IC|50|= 0.3 nM), less potently antagonizes glucosylceramide synthase (GCS, IC|50|= 25 nM), and only poorly inhibits other GCase isoforms. The lipid messenger ceramide is converted to glucosylceramide by GCS. In the reverse direction, BGD cleaves the glucosyl moiety from glucosylceramide, liberating ceramide, which can be converted into sphingomyelin. AMP-dNM has been shown to induce sterol regulatory element-binding protein-regulated gene expression and cholesterol synthesis in Hep-G2 cells, strongly suppress inflammation in a murine model of hapten-induced colitis, and enhance insulin sensitivity in murine and rat models of insulin resistance.

Specifications

Synonyme
AMP-dNM
Spezifikationen & Reinheit
A solution in ethanol
Storage
Store at -20°C
Verschickt in
Ice chest + Ice pads
Dieses Produkt erfordert Kühlkettenversand. Grundversand und andere Economy-Optionen sind nicht verfügbar.
Produkteigenschaften
pKapKₐ: 13.72 (Predicted), pKₐ: 6.86 (Predicted)
Namen und Kennungen
Kanonisches LächelnC1C2CC3CC1CC(C2)(C3)COCCCCCN4CC(C(C(C4CO)O)O)O
IUPAC Name(2R,3R,4R,5S)-1-[5-(1-adamantylmethoxy)pentyl]-2-(hydroxymethyl)piperidine-3,4,5-triol
InChIKeyXVYLNHVEAOOEGI-FAIWKWDXSA-N
INCHI1S/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
Isomere SMILES C1[C@@H]([C@H]([C@@H]([C@H](N1CCCCCOCC23CC4CC(C2)CC(C4)C3)CO)O)O)O
UN-Nummer 1170
Verpackungsgruppe II
Molekulargewicht 397.6
Reaxy-Rn 26024209
Reaxys-RN_link_address https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=26024209&ln=

Documentation

📋 Safety Data Sheet (SDS)

Comprehensive hazard, handling, storage, and regulatory compliance document.

Download SDS →

✅ Certificate of Analysis (COA)

Lot-specific quality data. Enter your lot number to retrieve the exact COA.

Look up COA →

📊 Datasheet

Quick-reference summary of product specifications and applications.

View datasheet →

🔬 Specification Sheet

Full quality attributes and acceptance criteria for this grade.

View spec sheet →

Advanced Data

Taxonomic Classification

Taxonomy Tree

KingdomOrganic compounds
SuperclassOrganoheterocyclic compounds
KlassePiperidines
SubclassNot available
Intermediate Tree Nodes Not available
Direct ParentPiperidines
Alternative Parents Trialkylamines  Secondary alcohols  1,2-aminoalcohols  Polyols  Dialkyl ethers  Azacyclic compounds  Primary alcohols  Hydrocarbon derivatives  
Molecular FrameworkAliphatic heteropolycyclic compounds
Substituents Piperidine - 1,2-aminoalcohol - Secondary alcohol - Tertiary amine - Tertiary aliphatic amine - Dialkyl ether - Ether - Polyol - Azacycle - Organic oxygen compound - Organooxygen compound - Organonitrogen compound - Alcohol - Organic nitrogen compound - Primary alcohol - Hydrocarbon derivative - Amine - Aliphatic heteropolycyclic compound
BeschreibungThis compound belongs to the class of organic compounds known as piperidines. These are compounds containing a piperidine ring, which is a saturated aliphatic six-member ring with one nitrogen atom and five carbon atoms.
External Descriptors Not available
3D-Struktur
Interaktives chemisches Strukturmodell





Zugehörige Ziele (menschlich)
UGCG Tclin Ceramide glucosyltransferase (5 Activities)
Activity TypeActivity Value -log(M)Mechanism of ActionActivity ReferencePublications (PubMed IDs)
GBA2 Tchem Non-lysosomal glucosylceramidase (8 Activities)
Activity TypeActivity Value -log(M)Mechanism of ActionActivity ReferencePublications (PubMed IDs)
GAA Tclin Lysosomal alpha-glucosidase (2 Activities)
Activity TypeActivity Value -log(M)Mechanism of ActionActivity ReferencePublications (PubMed IDs)
SI Tchem Sucrase-isomaltase, intestinal (2 Activities)
Activity TypeActivity Value -log(M)Mechanism of ActionActivity ReferencePublications (PubMed IDs)
GBA Tclin Glucosylceramidase (2 Activities)
Activity TypeActivity Value -log(M)Mechanism of ActionActivity ReferencePublications (PubMed IDs)
MGAM Tclin Maltase-glucoamylase (654 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
UGCG Tclin Ceramide glucosyltransferase (308 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
GLB1 Tchem Beta-galactosidase (339 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
GBA1 Tclin Beta-glucocerebrosidase (14647 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
GAA Tclin Lysosomal alpha-glucosidase (35701 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
GBA2 Tchem Beta-glucosidase (258 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
SI Tchem Sucrase-isomaltase (84 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
AGL Tbio Glycogen debranching enzyme (27 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
LCT Tbio Lactase-phlorizin hydrolase (37 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Zugehörige Ziele (nicht menschlich)
Mus musculus (284745 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Rattus norvegicus (775804 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Wirkungsmechanismen
Zertifikate (CoA, COO, BSE/TSE und Analyse-Diagramm)
C of A & Other Certificates(BSE/TSE, COO):
Analytical Chart:
Chemische und physikalische Eigenschaften
LöslichkeitSoluble in ethanol (~30 mg/ml), DMSO (~50 mg/ml), DMF (~50 mg/ml), aqueous buffers (sparingly), and chloroform.
Brechungsindexn20D1.57 (Predicted)
Siedepunkt (°C)78° C
Molekulargewicht397.500 g/mol
XLogP31.900
Hydrogen Bond Donor Count4
Hydrogen Bond Acceptor Count6
Rotatable Bond Count9
Exact Mass397.283 Da
Monoisotopic Mass397.283 Da
Topological Polar Surface Area93.400 Ų
Heavy Atom Count28
Formal Charge0
Complexity474.000
Isotope Atom Count0
Defined Atom Stereocenter Count4
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
The total count of all stereochemical bonds0
Covalently-Bonded Unit Count1
Lösungsrechner
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Häufig gestellte Fragen

How should this product be stored?
Store at ?20 °C. Freezer storage is required to maintain the specified shelf life.
How is this product shipped?
This product ships in an insulated container with ice pads. Unpack on arrival and transfer it to the storage condition stated above.
What are the CAS number, molecular formula and molecular weight?
The CAS Number is 216758-20-2, the molecular formula is C22H39NO5, and the molecular weight is 397.6 g/mol. InChIKey XVYLNHVEAOOEGI-FAIWKWDXSA-N.
What documentation is provided?
Available product documentation, including Certificates of Analysis (COA), Safety Data Sheets (SDS), and specification sheets, is shown in the product document area. Document availability and access follow the current site policy.

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