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

CAS: 216758-20-2 Cat. No.: A338640 Molecular Weight: 397.6
AVAILABLE TO ORDER
GRADE & PURITY A solution in ethanol
Synonyms
AMP-dNM
Storage
Store at -20°C
Shipped In
Ice chest + Ice pads
 ·  off list, applied to all prices below.
Size
Status
Price
Qty
1mg
A338640-1mg
8-12 wks(?) Production requires sourcing of materials. We appreciate your patience and understanding.
$283.90
500μg
A338640-500μg
8-12 wks(?) Production requires sourcing of materials. We appreciate your patience and understanding.
$142.90
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Why this grade

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

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Storage & shipping

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

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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.

Overview

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

Synonyms
AMP-dNM
Specifications & Purity
A solution in ethanol
Storage
Store at -20°C
Shipped In
Ice chest + Ice pads
This product requires cold chain shipping. Ground and other economy services are not available.
Product Properties
pKapKₐ: 13.72 (Predicted), pKₐ: 6.86 (Predicted)
Names and Identifiers
Canonical SmilesC1C2CC3CC1CC(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
Isomeric SMILES C1[C@@H]([C@H]([C@@H]([C@H](N1CCCCCOCC23CC4CC(C2)CC(C4)C3)CO)O)O)O
UN Number 1170
Packing Group II
Molecular Weight 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
ClassPiperidines
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
DescriptionThis 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 Structure
Interactive Chemical Structure Model





Associated Targets(Human)
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
Associated Targets(non-human)
Mus musculus (284745 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Rattus norvegicus (775804 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Mechanisms of Action
Certificates(CoA,COO,BSE/TSE and Analysis Chart)
C of A & Other Certificates(BSE/TSE, COO):
Analytical Chart:
Chemical and Physical Properties
SolubilitySoluble in ethanol (~30 mg/ml), DMSO (~50 mg/ml), DMF (~50 mg/ml), aqueous buffers (sparingly), and chloroform.
Refractive Indexn20D1.57 (Predicted)
Boil Point(°C)78° C
Molecular Weight397.500 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
Solution Calculators
Reviews

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