Phenyl β-D-glucopyranoside - Moligand™, ≥98% , Agonist of TAS2R16, CAS No.1464-44-4, Agonist of TAS2R16

CAS: 1464-44-4 Cat. No.: P103807 Molecular Weight: 256.25 Beilstein Registry Number: 87517 EC Number: 215-978-6

GRADE & PURITY Moligand™, ≥98%

Synonyms

BDBM36025 | beta-D-Glucopyranoside, phenyl | 5-17-07-00046 (Beilstein Handbook Reference) | AS-59078 | SCHEMBL1004929 | Glucopyranoside, phenyl-, .beta.-D- | (2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-phenoxy-tetrahydropyran-3,4,5-triol | AKOS001669140 | Glucop

Storage

Room temperature

Shipped In

Normal

Specifications

Synonyms

BDBM36025 | beta-D-Glucopyranoside, phenyl | 5-17-07-00046 (Beilstein Handbook Reference) | AS-59078 | SCHEMBL1004929 | Glucopyranoside, phenyl-, .beta.-D- | (2R, 3S, 4S, 5R, 6S)-2-(hydroxymethyl)-6-phenoxy-tetrahydropyran-3, 4, 5-triol | AKOS001669140 | Glucop

Specifications & Purity

Moligand™, ≥98%

Storage

Room temperature

Shipped In

Normal

Grade

Moligand™

Action Type

AGONIST

Mechanism of action

Agonist of TAS2R16

Purity

≥98%

Names and Identifiers

• Pubchem Sid: 488183658
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/488183658
• Canonical Smiles: C1=CC=C(C=C1)OC2C(C(C(C(O2)CO)O)O)O
• IUPAC Name: (2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-phenoxyoxane-3,4,5-triol
• InChIKey: NEZJDVYDSZTRFS-RMPHRYRLSA-N
• INCHI: 1S/C12H16O6/c13-6-8-9(14)10(15)11(16)12(18-8)17-7-4-2-1-3-5-7/h1-5,8-16H,6H2/t8-,9-,10+,11-,12-/m1/s1
• Isomeric SMILES: C1=CC=C(C=C1)O[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CO)O)O)O
• WGK Germany: 3
• RTECS: LZ5985510
• Alternate CAS: 1464-44-4
• MeSH Entry Terms: phenyl beta-D-glucopyranoside;phenyl-beta-glucoside;phenylglucoside;phenylglucoside, (alpha-(D))-isomer;phenylglucoside, (alpha-(L))-isomer
• Molecular Weight: 256.25
• Beilstein: 87517
• Reaxy-Rn: 24712299
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=24712299&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organic oxygen compounds
    • Class Organooxygen compounds
      • Subclass Carbohydrates and carbohydrate conjugates
        • Level5 Glycosyl compounds
          • Level6 Phenolic glycosides

• Kingdom: Organic compounds
• Superclass: Organic oxygen compounds
• Class: Organooxygen compounds
• Subclass: Carbohydrates and carbohydrate conjugates
• Intermediate Tree Nodes: Glycosyl compounds
• Direct Parent: Phenolic glycosides
• Alternative Parents: O-glycosyl compounds Phenoxy compounds Phenol ethers Oxanes Monosaccharides Secondary alcohols Polyols Oxacyclic compounds Acetals Primary alcohols Hydrocarbon derivatives
• Molecular Framework: Aromatic heteromonocyclic compounds
• Substituents: Phenolic glycoside - O-glycosyl compound - Phenoxy compound - Phenol ether - Monocyclic benzene moiety - Monosaccharide - Benzenoid - Oxane - Secondary alcohol - Acetal - Oxacycle - Organoheterocyclic compound - Polyol - Alcohol - Primary alcohol - Hydrocarbon derivative - Aromatic heteromonocyclic compound
• Description: This compound belongs to the class of organic compounds known as phenolic glycosides. These are organic compounds containing a phenolic structure attached to a glycosyl moiety. Some examples of phenolic structures include lignans, and flavonoids. Among the sugar units found in natural glycosides are D-glucose, L-Fructose, and L rhamnose.
• External Descriptors: beta-D-glucoside

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)

TAS2R16 Tchem Taste receptor type 2 member 16 (0 Activities)

Discover Target: TAS2R16

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

Homo sapiens (32628 Activities)

Explore this target

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

TAS2R16 Tchem Taste receptor type 2 member 16 (102 Activities)

Discover Target: TAS2R16

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 water
• Specific Rotation[α]: -70.5 ° (C=2, H2O)
• Melt Point(°C): 176-178°C
• Molecular Weight: 256.250 g/mol
• XLogP3: -0.900
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 3
• Exact Mass: 256.095 Da
• Monoisotopic Mass: 256.095 Da
• Topological Polar Surface Area: 99.400 Ų
• Heavy Atom Count: 18
• Formal Charge: 0
• Complexity: 255.000
• 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. Kunya Cheng, Binchen Wang, Lin Xiao, Yuxiang Bao, Xianbing Xu, Sufang Zhang, Zhaofang Liu, Liang Dong.  (2022)  Comprehensive metabolite analysis of wheat dough in a continuous heating process.  FOOD RESEARCH INTERNATIONAL,      [PMID:35227483] [10.1016/j.foodres.2022.110972]

2. Zhao Xinchi, Li Chongwei, Jiang Yumeng, Wang Meiting, Wang Binchen, Xiao Lin, Xu Xianbing, Chai Duo, Dong Liang.  (2020)  Metabolite fingerprinting of buckwheat in the malting process.  Journal of Food Measurement and Characterization,  15  (2): (1475-1486).  [PMID:] [10.1007/s11694-020-00737-1]

3. Binchen Wang, Lin Xiao, Duo Chai, Yumeng Jiang, Meiting Wang, Xianbing Xu, Chongwei Li, Liang Dong.  (2020)  Metabolite analysis of wheat dough fermentation incorporated with buckwheat.  Food Science & Nutrition,  8  (8): (4242-4251).  [PMID:32884705] [10.1002/fsn3.1720]

4. Xilin Jiang, Jian Tang, Zhiqiang Gao, Caixia Chen, Wenjun Li, Lu Peng, Hongwei Li, Hongying Zhao, Yun Zhao.  (2024)  Exploring the protection on islet β-cells and hypoglycemic effect of Moringa oleifera stem based on network pharmacology and experimental validation.  Journal of Functional Foods,      [PMID:] [10.1016/j.jff.2024.106499]