4-Methylumbelliferyl β-D-glucopyranoside - ≥99% , CAS No.18997-57-4

CAS: 18997-57-4 Cat. No.: M103899 Molecular Weight: 338.31 Beilstein Registry Number: 94672 EC Number: 242-736-7

GRADE & PURITY ≥99%

Synonyms

A813381 | HY-123633 | YUDPTGPSBJVHCN-YMILTQATSA-N | 4-methyl-2-oxo-2H-1-benzopyran-7-yl beta-D-glucopyranoside | BDBM18352 | 4-methylumbelliferyl beta-D-glucoside | (4-Methylumbelliferone)-beta-D-glucopyranoside | 4-Methylumbelliferyl beta-D-glucopyranosi

Storage

Protected from light,Store at -20°C

Shipped In

Ice chest + Ice pads

Overview

4-Methylumbelliferyl β-D-glucopyranoside is a synthetic enzymatic substrate for glycosidase. It has been used as substrate for the β- glucosidase from enterococci.

Specifications

Synonyms

A813381 | HY-123633 | YUDPTGPSBJVHCN-YMILTQATSA-N | 4-methyl-2-oxo-2H-1-benzopyran-7-yl beta-D-glucopyranoside | BDBM18352 | 4-methylumbelliferyl beta-D-glucoside | (4-Methylumbelliferone)-beta-D-glucopyranoside | 4-Methylumbelliferyl beta-D-glucopyranosi

Specifications & Purity

≥99%

Biochemical and Physiological Mechanisms

Fluorogenic substrate of β-glucosidase and β-glucocerebrosidase (also known as glucosylceramidase). Used for characterizing novel β-glucosidases. Also used in assays to evaluate deficiency in β-glucocerebrosidase activity related to Gaucher disease.

Storage

Protected from light, Store at -20°C

Shipped In

Ice chest + Ice pads

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

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

≥99%

Names and Identifiers

• Pubchem Sid: 504761031
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/504761031
• Canonical Smiles: CC1=CC(=O)OC2=C1C=CC(=C2)OC3C(C(C(C(O3)CO)O)O)O
• IUPAC Name: 4-methyl-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-2-one
• InChIKey: YUDPTGPSBJVHCN-YMILTQATSA-N
• INCHI: 1S/C16H18O8/c1-7-4-12(18)23-10-5-8(2-3-9(7)10)22-16-15(21)14(20)13(19)11(6-17)24-16/h2-5,11,13-17,19-21H,6H2,1H3/t11-,13-,14+,15-,16-/m1/s1
• Isomeric SMILES: CC1=CC(=O)OC2=C1C=CC(=C2)O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O
• WGK Germany: 3
• Molecular Weight: 338.31
• Beilstein: 94672
• Reaxy-Rn: 24926198
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=24926198&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 Hexoses O-glycosyl compounds 1-benzopyrans Pyranones and derivatives Benzenoids Oxanes Heteroaromatic compounds Secondary alcohols Lactones Acetals Polyols Oxacyclic compounds Primary alcohols Organic oxides Hydrocarbon derivatives
• Molecular Framework: Aromatic heteropolycyclic compounds
• Substituents: Coumarin-7-o-glycoside - Coumarin o-glycoside - Phenolic glycoside - Hexose monosaccharide - Glycosyl compound - O-glycosyl compound - Benzopyran - 1-benzopyran - Pyranone - Monosaccharide - Oxane - Benzenoid - Pyran - Heteroaromatic compound - Lactone - Secondary alcohol - Polyol - Organoheterocyclic compound - Acetal - Oxacycle - Alcohol - Organooxygen compound - Hydrocarbon derivative - Organic oxide - Primary alcohol - Organic oxygen compound - 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

Associated Targets(Human)

CA1 Tclin Carbonic anhydrase 1 (1 Activities)

Discover Target: CA1

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

CA12 Tclin Carbonic anhydrase 12 (1 Activities)

Discover Target: CA12

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

CA9 Tclin Carbonic anhydrase 9 (1 Activities)

Discover Target: CA9

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

CA2 Tclin Carbonic anhydrase II (17698 Activities)

Discover Target: CA2

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

CA1 Tclin Carbonic anhydrase I (13240 Activities)

Discover Target: CA1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

CA12 Tclin Carbonic anhydrase XII (6231 Activities)

Discover Target: CA12

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

CA9 Tclin Carbonic anhydrase IX (8255 Activities)

Discover Target: CA9

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Mechanisms of Action

Chemical and Physical Properties

• Solubility: Soluble in DMF or water
• Sensitivity: Heat sensitive；light sensitive
• Specific Rotation[α]: -97.5 to -108.0 deg(C=0.3, water)
• Melt Point(°C): 216 °C(dec.)
• Molecular Weight: 338.310 g/mol
• XLogP3: -0.800
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 3
• Exact Mass: 338.1 Da
• Monoisotopic Mass: 338.1 Da
• Topological Polar Surface Area: 126.000 Ų
• Heavy Atom Count: 24
• Formal Charge: 0
• Complexity: 506.000
• 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

References

1. Yu-Xi Feng, Xin Chen, Yan-Wen Li, Hai-Ming Zhao, Lei Xiang, Hui Li, Quan-Ying Cai, Nai-Xian Feng, Ce-Hui Mo, Ming-Hung Wong.  (2020)  A Visual Leaf Zymography Technique for the In Situ Examination of Plant Enzyme Activity under the Stress of Environmental Pollution.  JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY,      [PMID:32822176] [10.1021/acs.jafc.0c03815]