4-Methylumbelliferyl α-L-iduronide (free acid) , CAS No.66966-09-4

CAS: 66966-09-4 Cat. No.: M331620 Molecular Weight: 352.29 EC Number: 266-527-5

Synonyms

4-Methylumbelliferyl iduronide | alpha-L-Idopyranosiduronic acid, 4-methyl-2-oxo-2H-1-benzopyran-7-yl | 8U8 | 4-Methylumbelliferyl alpha-L-iduronide (free acid) | SCHEMBL308321 | 4-Methylumbelliferyl alpha -L-iduronide (free acid) | 4-methylumbelliferyl-a

Storage

Store at -20°C,Desiccated

Shipped In

Ice chest + Ice pads

Overview

4-Methylumbelliferyl α-L-iduronide (free acid) is a fluorogenic substrate for α-L-iduronidase. This is found in cell lysosomes, which is involved in the degradation of glycosaminoglycans. 4-Methylumbelliferyl-α-L-iduronide is cleaved by α-L-iduronidase to release the fluorescent moiety 4-methylumbelliferyl (4-MU). This 4-Methylumbelliferyl α-L-iduronide form is the free acid, which offers a considerable weight for weight advantage over the 4-MU iduronide salt in terms of its application dose.|For further studies, use α-L-iduronidase gene silencing|siRNA and shRNA|reagents and α-L-iduronidase gene editing|CRISPR|knockout and activation products.

Specifications

Synonyms

4-Methylumbelliferyl iduronide | alpha-L-Idopyranosiduronic acid, 4-methyl-2-oxo-2H-1-benzopyran-7-yl | 8U8 | 4-Methylumbelliferyl alpha-L-iduronide (free acid) | SCHEMBL308321 | 4-Methylumbelliferyl alpha -L-iduronide (free acid) | 4-methylumbelliferyl-a

Storage

Store at -20°C, Desiccated

Shipped In

Ice chest + Ice pads

This product requires cold chain shipping. Ground and other economy services are not available.

Note

4-Methylumbelliferyl α-L-iduronide (free acid) can be used in assays that measure the activity of α-L-iduronidase.

Names and Identifiers

• Canonical Smiles: CC1=CC(=O)OC2=C1C=CC(=C2)OC3C(C(C(C(O3)C(=O)O)O)O)O
• IUPAC Name: (2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-(4-methyl-2-oxochromen-7-yl)oxyoxane-2-carboxylic acid
• InChIKey: ARQXEQLMMNGFDU-ZHMBSYLPSA-N
• INCHI: 1S/C16H16O9/c1-6-4-10(17)24-9-5-7(2-3-8(6)9)23-16-13(20)11(18)12(19)14(25-16)15(21)22/h2-5,11-14,16,18-20H,1H3,(H,21,22)/t11-,12-,13+,14+,16+/m0/s1
• Isomeric SMILES: CC1=CC(=O)OC2=C1C=CC(=C2)O[C@H]3[C@@H]([C@H]([C@@H]([C@@H](O3)C(=O)O)O)O)O
• Molecular Weight: 352.29
• Reaxy-Rn: 24881770
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=24881770&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Phenylpropanoids and polyketides
    • Class Coumarins and derivatives
      • Subclass Coumarin glycosides

• Kingdom: Organic compounds
• Superclass: Phenylpropanoids and polyketides
• Class: Coumarins and derivatives
• Subclass: Coumarin glycosides
• Intermediate Tree Nodes: Not available
• Direct Parent: Coumarin glycosides
• Alternative Parents: Phenolic glycosides O-glucuronides O-glycosyl compounds 1-benzopyrans Pyranones and derivatives Beta hydroxy acids and derivatives Benzenoids Monosaccharides Oxanes Heteroaromatic compounds Lactones Secondary alcohols Acetals Monocarboxylic acids and derivatives Carboxylic acids Polyols Oxacyclic compounds Hydrocarbon derivatives Carbonyl compounds Organic oxides
• Molecular Framework: Aromatic heteropolycyclic compounds
• Substituents: Coumarin-7-o-glycoside - Coumarin o-glycoside - Phenolic glycoside - 1-o-glucuronide - O-glucuronide - Glucuronic acid or derivatives - O-glycosyl compound - Glycosyl compound - Benzopyran - 1-benzopyran - Pyranone - Beta-hydroxy acid - Benzenoid - Pyran - Oxane - Hydroxy acid - Monosaccharide - Heteroaromatic compound - Secondary alcohol - Lactone - Oxacycle - Organoheterocyclic compound - Polyol - Carboxylic acid derivative - Carboxylic acid - Acetal - Monocarboxylic acid or derivatives - Organic oxygen compound - Organic oxide - Organooxygen compound - Alcohol - Carbonyl group - Hydrocarbon derivative - Aromatic heteropolycyclic compound
• Description: This compound belongs to the class of organic compounds known as coumarin glycosides. These are aromatic compounds containing a carbohydrate moiety glycosidically bound to a coumarin moiety.
• External Descriptors: Not available

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

Chemical and Physical Properties

• Refractive Index: n20D1.66
• Boil Point(°C): 683.1° C at 760 mmHg
• Molecular Weight: 352.290 g/mol
• XLogP3: -0.500
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 3
• Exact Mass: 352.079 Da
• Monoisotopic Mass: 352.079 Da
• Topological Polar Surface Area: 143.000 Ų
• Heavy Atom Count: 25
• Formal Charge: 0
• Complexity: 574.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 5
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1