2-[N-(7-Nitrobenz-2-oxa-1,3-diazol-4-yl)amino]-2-deoxy-D-glucose（2-NBDG） - ≥97% , CAS No.186689-07-6

CAS: 186689-07-6 Cat. No.: N121715 Peso molecular: 342.26 Beilstein Registry Number: 7603370 Número EC: 811-648-6

GRADE & PURITY ≥97%

Synonyms

2-NBDG | UNII-JE4F4P486R | MolMap_000037 | PD102201 | HY-116215 | JE4F4P486R | 2-(N-(7-nitrobenz-2-oxa-1,3-diazol-4-yl)amino)-2-deoxy-D-glucose | (2R,3R,4S,5R)-3,4,5,6-tetrahydroxy-2-[(4-nitro-2,1,3-benzoxadiazol-7-yl)amino]hexanal

Storage

Protected from light,Store at -20°C,Argon charged

Shipped In

Ice chest + Ice pads

Descripción general

fluorescent indicator for monotoring of glucose uptake into living cells

Specifications

Sinónimos

2-NBDG | UNII-JE4F4P486R | MolMap_000037 | PD102201 | HY-116215 | JE4F4P486R | 2-(N-(7-nitrobenz-2-oxa-1, 3-diazol-4-yl)amino)-2-deoxy-D-glucose | (2R, 3R, 4S, 5R)-3, 4, 5, 6-tetrahydroxy-2-[(4-nitro-2, 1, 3-benzoxadiazol-7-yl)amino]hexanal

Especificaciones y pureza

≥97%

Mecanismos bioquímicos y fisiológicos

Fluorescent glucose analog for visualizing glucose uptake into living cells.

Condiciones de almacenamiento de almacenamiento

Protected from light, Store at -20°C, Argon charged

Enviado en

Ice chest + Ice pads

Este producto requiere envío en cadena de frío. Los servicios terrestres y otros servicios económicos no están disponibles.

Pureza

≥97%

Nombres e identificadores

• Sonrisas canónicas: C1=C(C2=NON=C2C(=C1)[N+](=O)[O-])NC(C=O)C(C(C(CO)O)O)O
• IUPAC Name: (2R,3R,4S,5R)-3,4,5,6-tetrahydroxy-2-[(4-nitro-2,1,3-benzoxadiazol-7-yl)amino]hexanal
• InChIKey: QUTFFEUUGHUPQC-ILWYWAAHSA-N
• INCHI: 1S/C12H14N4O8/c17-3-6(11(20)12(21)8(19)4-18)13-5-1-2-7(16(22)23)10-9(5)14-24-15-10/h1-3,6,8,11-13,18-21H,4H2/t6-,8+,11+,12+/m0/s1
• Isómeros SMILES: C1=C(C2=NON=C2C(=C1)[N+](=O)[O-])N[C@@H](C=O)[C@H]([C@@H]([C@@H](CO)O)O)O
• WGK Alemania: 3
• Peso molecular: 342.26
• Beilstein: 7603370
• Reaxy-Rn: 31645326
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=31645326&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organoheterocyclic compounds
    • Clase Benzoxadiazoles

• Kingdom: Organic compounds
• Superclass: Organoheterocyclic compounds
• Clase: Benzoxadiazoles
• Subclass: Not available
• Intermediate Tree Nodes: Not available
• Direct Parent: Benzoxadiazoles
• Alternative Parents: Nitroaromatic compounds Secondary alkylarylamines Aminosaccharides Benzenoids Beta-hydroxy aldehydes Monosaccharides 1,3-aminoalcohols Furazans Heteroaromatic compounds Secondary alcohols Propargyl-type 1,3-dipolar organic compounds Azacyclic compounds Polyols Oxacyclic compounds Organic oxoazanium compounds Organic zwitterions Organic salts Hydrocarbon derivatives Primary alcohols Organic oxides
• Molecular Framework: Aromatic heteropolycyclic compounds
• Substituents: Benzoxadiazole - Nitroaromatic compound - Secondary aliphatic/aromatic amine - Amino saccharide - Beta-hydroxy aldehyde - Monosaccharide - Benzenoid - 1,3-aminoalcohol - Azole - Heteroaromatic compound - Furazan - Oxadiazole - C-nitro compound - Organic nitro compound - Secondary alcohol - Organic 1,3-dipolar compound - Secondary amine - Allyl-type 1,3-dipolar organic compound - Propargyl-type 1,3-dipolar organic compound - Oxacycle - Polyol - Azacycle - Organic oxoazanium - Organic salt - Organonitrogen compound - Organooxygen compound - Organic nitrogen compound - Alcohol - Primary alcohol - Carbonyl group - Hydrocarbon derivative - Organic oxide - Organic oxygen compound - Amine - Organic zwitterion - Aldehyde - Aromatic heteropolycyclic compound
• Descripción: This compound belongs to the class of organic compounds known as benzoxadiazoles. These are organic compounds containing a benzene fused to an oxadiazole ring (a five-membered ring with two carbon atoms, one nitrogen atom, and one oxygen atom).
• 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

Propiedades químicas y físicas

• Solubilidad: Solvent:DMSO, Max Conc. mg/mL: 34.23, Max Conc. mM: 100
• Sensibilidad: Light sensitive;Moisture sensitive;heat sensitive
• Peso molecular: 342.260 g/mol
• XLogP3: -1.400
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 11
• Rotatable Bond Count: 7
• Exact Mass: 342.081 Da
• Monoisotopic Mass: 342.081 Da
• Topological Polar Surface Area: 195.000 Ų
• Heavy Atom Count: 24
• Formal Charge: 0
• Complexity: 449.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 4
• 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

Referencias

1. Qin Fei, Zeng Huicong, Zhou Li, Zhou Zhenhua, Mao Yongxin, Zeng Youyan, Guo Rongxiang, Chen Kaixian, Zhao Dongyu, Yao Weiwei, Zhang Bin, Zhou Qian, Li Bo.  (2025)  Identification of novel small molecules as potential SGLT2 inhibitors through combined virtual screening and experimental validation.  MOLECULAR DIVERSITY,      [PMID:41021175] [10.1007/s11030-025-11367-4]

2. Zhu Chao-wei, Lü Han, Du Lan-lan, Li Jing, Chen Han, Zhao Hui-fang, Wu Wen-long, Chen Jian, Li Wei-lin.  (2023)  Five blueberry anthocyanins and their antioxidant, hypoglycemic, and hypolipidemic effects in vitro.  Frontiers in Nutrition,      [PMID:37275633] [10.3389/fnut.2023.1172982]

3. Meimei Zhao, Ziteng Yu, Xinyi Zhao, Ruijiao Zhu, Mengcong Li, Lu Yu, Ziwei Song, Jiangwei Lv.  (2025)  Inhibition of RAGE-mediated inflammatory signaling by Boletus edulis Bull: Fr. Polysaccharide alleviates lipotoxicity-induced metabolic dysfunction.  BIOCHEMICAL PHARMACOLOGY,      [PMID:41115475] [10.1016/j.bcp.2025.117439]

4. Guixiang Zeng, Jingjing Lian, Jiajia Shen, Yuan Shi.  (2025)  The effect of Klotho protein on biological behavior of JEG-3 cells.  TISSUE & CELL,      [PMID:41161232] [10.1016/j.tice.2025.103198]

5. Yaoqi Wu, Wenkai Lv, Shaofeng Xiong, Guosheng Cao, Longsheng Fu, Wen Liu, Feng Shao, Yanqin Mei, Yanni Lv.  (2025)  Dalbergia odorifera T.C. Chen Leaf Extract Promotes Microglial Energy Expenditure to Phagocytize Neutrophils After Cerebral Ischemia-reperfusion.  PHYTOMEDICINE,      [PMID:41253024] [10.1016/j.phymed.2025.157508]

6. Cheng Li, Ruihang Zhang, Yuhan Zhang, Hongxi Yu, Yu Zheng, Yifei Du, Shiyi Hong, Lihua Hu, Chaoyang Wang, Guang Jia, Guiping Hu.  (2026)  Chromium(VI) Modulates Macrophage Polarization and Metabolic Reprogramming to Impair Immune Function.  Toxics,  14  (2): (160).  [PMID:41745834] [10.3390/toxics14020160]