Acarbose Hydrate - Moligand™, ≥98% , Inhibitor of amylase alpha 2A;Inhibitor of maltase-glucoamylase, CAS No.56180-94-0, Inhibitor of amylase alpha 2A;Inhibitor of maltase-glucoamylase

CAS: 56180-94-0 Cat. No.: A129816 Formula: C₂₅H₄₃NO₁₈·xH₂O Molecular Weight: 645.61(as Anhydrous) EC Number: 260-030-7

GRADE & PURITY Moligand™, ≥98%

Synonyms

Bay-g 5421 | BAY g 5421 | Bay g 5421 | BRD-A16444946-001-07-1 | MLS001424056 | AB00639959-06 | HMS2093I22 | MFCD00869592 | Prandase; | SR-01000759407 | SBI-0206777.P001 | acarbose | MD-0230 | SR-01000759407-4 | Acarbose; O-4,6-Dideoxy-4-[[(1S,4R,5S,6S)-4,

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Overview

Acarbose, also known as BAY g 5421, is an α-glucosidase inhibitor that prevents absorption of sucrose and maltose. This compound has been found to delay digestion of complex disaccharides and carbohydrates. Further studies suggest that this compound can stimulate phosphorylase kinase (PhK) by binding to the glucoamylase-like domain new the amino termini and causing an alteration in the structure.
An α-glucosidase inhibitor

Application：

Acarbose, a derivitized maltotriose antidiabetic drug, is a reversible α-glucosidase inhibitor used in medical studies to control the effects of Type II diabetes. Acarbose is often used as a reference to which other α-glucosidase inhibitors are compared.

Specifications

Synonyms

Bay-g 5421 | BAY g 5421 | Bay g 5421 | BRD-A16444946-001-07-1 | MLS001424056 | AB00639959-06 | HMS2093I22 | MFCD00869592 | Prandase; | SR-01000759407 | SBI-0206777.P001 | acarbose | MD-0230 | SR-01000759407-4 | Acarbose; O-4,6-Dideoxy-4-[[(1S,4R,5S,6S)-4,

Specifications & Purity

Moligand™, ≥98%

Biochemical and Physiological Mechanisms

Potent α-glucosidase inhibitor (IC 50 = 11 nM). Orally active. Antidiabetic.

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.

Grade

Moligand™

Action Type

INHIBITOR

Mechanism of action

Inhibitor of amylase alpha 2A;Inhibitor of maltase-glucoamylase

Note

Wherever possible, you should prepare and use solutions on the same day. However, if you need to make up stock solutions in advance, we recommend that you store the solution as aliquots in tightly sealed vials at -20°C. Generally, these will be useable for up to one month. Before use, and prior to opening the vial we recommend that you allow your product to equilibrate to room temperature for at least 1 hour. Need more advice on solubility, usage and handling? Please visit our frequently asked questions (FAQ) page for more details.

Purity

≥98%

Names and Identifiers

• Pubchem Sid: 488183332
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/488183332
• Canonical Smiles: CC1C(C(C(C(O1)OC2C(OC(C(C2O)O)OC3C(OC(C(C3O)O)O)CO)CO)O)O)NC4C=C(C(C(C4O)O)O)CO
• IUPAC Name: (3R,4R,5S,6R)-5-[(2R,3R,4R,5S,6R)-5-[(2R,3R,4S,5S,6R)-3,4-dihydroxy-6-methyl-5-[[(1S,4R,5S,6S)-4,5,6-trihydroxy-3-(hydroxymethyl)cyclohex-2-en-1-yl]amino]oxan-2-yl]oxy-3,4-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-6-(hydroxymethyl)oxane-2,3,4-triol
• InChIKey: XUFXOAAUWZOOIT-UGEKTDRHSA-N
• INCHI: 1S/C25H43NO18/c1-6-11(26-8-2-7(3-27)12(30)15(33)13(8)31)14(32)19(37)24(40-6)43-22-10(5-29)42-25(20(38)17(22)35)44-21-9(4-28)41-23(39)18(36)16(21)34/h2,6,8-39H,3-5H2,1H3/t6-,8+,9-,10-,11-,12-,13+,14+,15+,16-,17-,18-,19-,20-,21-,22-,23?,24-,25-/m1/s1
• Isomeric SMILES: C[C@@H]1[C@H]([C@@H]([C@H]([C@H](O1)O[C@@H]2[C@H](O[C@@H]([C@@H]([C@H]2O)O)O[C@@H]3[C@H](OC([C@@H]([C@H]3O)O)O)CO)CO)O)O)N[C@H]4C=C([C@H]([C@@H]([C@H]4O)O)O)CO
• RTECS: LZ7153000
• Molecular Weight: 645.61(as Anhydrous)
• Reaxy-Rn: 24713589
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=24713589&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organic oxygen compounds
    • Class Organooxygen compounds
      • Subclass Carbohydrates and carbohydrate conjugates
        • Level5 Aminosaccharides
          • Level6 Aminoglycosides
            • Level7 Aminocyclitol glycosides

• Kingdom: Organic compounds
• Superclass: Organic oxygen compounds
• Class: Organooxygen compounds
• Subclass: Carbohydrates and carbohydrate conjugates
• Intermediate Tree Nodes: Aminosaccharides - Aminoglycosides
• Direct Parent: Aminocyclitol glycosides
• Alternative Parents: Oligosaccharides O-glycosyl compounds Oxanes Cyclitols and derivatives Secondary alcohols Hemiacetals 1,2-aminoalcohols Polyols Oxacyclic compounds Dialkylamines Acetals Primary alcohols Organopnictogen compounds Hydrocarbon derivatives
• Molecular Framework: Aliphatic heteromonocyclic compounds
• Substituents: Oligosaccharide - Amino cyclitol glycoside - Glycosyl compound - O-glycosyl compound - Cyclitol or derivatives - Oxane - 1,2-aminoalcohol - Hemiacetal - Secondary alcohol - Secondary amine - Organoheterocyclic compound - Acetal - Oxacycle - Secondary aliphatic amine - Polyol - Organonitrogen compound - Organic nitrogen compound - Hydrocarbon derivative - Organopnictogen compound - Amine - Primary alcohol - Alcohol - Aliphatic heteromonocyclic compound
• Description: This compound belongs to the class of organic compounds known as aminocyclitol glycosides. These are organic compounds containing an amicocyclitol moiety glycosidically linked to a carbohydrate moiety. There are two major classes of aminoglycosides containing a 2-streptamine core. They are called 4,5- and 4,6-disubstituted 2-deoxystreptamines.
• External Descriptors: tetrasaccharide derivative

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Associated Targets(Human)

MGAM Tclin Maltase-glucoamylase, intestinal (0 Activities)

Discover Target: MGAM

Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

AMY2A Tclin Pancreatic alpha-amylase (0 Activities)

Discover Target: AMY2A

Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

Chemical and Physical Properties

• Solubility: Soluble in water (100 mM), DMSO (100 mM), and methanol.
• x_specific_rotation: 176° (C=1,H2O)
• Molecular Weight: 645.600 g/mol
• XLogP3: -8.500
• Hydrogen Bond Donor Count: 14
• Hydrogen Bond Acceptor Count: 19
• Rotatable Bond Count: 9
• Exact Mass: 645.248 Da
• Monoisotopic Mass: 645.248 Da
• Topological Polar Surface Area: 321.000 Ų
• Heavy Atom Count: 44
• Formal Charge: 0
• Complexity: 962.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 18
• Undefined Atom Stereocenter Count: 1
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1