Adenosine - PharmPure™,USP,Endotoxin

CAS: 58-61-7 Cat. No.: GMP1508325 Formula: C₁₀H₁₃N₅O₄ Molecular Weight: 267.24 Beilstein Registry Number: 93029 EC Number: 200-389-9

GRADE & PURITY PharmPure™, USP, Endotoxin<1000EU/g;Microbial Limit≤100cfu/g

Synonyms

9-β-D-Ribofuranosyladenine | Adenine riboside | Adenine-9-β-D-ribofuranoside | D-Adenosine

Storage

Store at 2-8°C,Argon charged

Shipped In

Wet ice

Application

836,837

Overview

Adenosine is a nucleoside formed by the attachment of adenine to a ribose sugar. Adenosine is a ubiquitous and BBB-permeable endogenous autacoid, acts through the enrollment of four G protein-coupled receptors: A1, A2A, A2B, and A3. Adenosine affects almost all aspects of cellular physiology, including neuronal activity, vascular function, platelet aggregation, and blood cell regulation.These products are for test and assay use only. They are not meant for administration to humans or animals and cannot be used to diagnose, treat, or cure diseases of any kind. ​

Specifications

Synonyms

9-β-D-Ribofuranosyladenine | Adenine riboside | Adenine-9-β-D-ribofuranoside | D-Adenosine

Specifications & Purity

PharmPure™,USP,Endotoxin<1000EU/g;Microbial Limit≤100cfu/g

Biochemical and Physiological Mechanisms

Neurotransmitter that acts as the preferred endogenous agonist at all adenosine receptor subtypes.

Storage

Store at 2-8°C,Argon charged

Shipped In

Wet ice

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

Grade

PharmPure™, USP

Names and Identifiers

Canonical Smiles

C1=NC(=C2C(=N1)N(C=N2)C3C(C(C(O3)CO)O)O)N

IUPAC Name

(2R,3R,4S,5R)-2-(6-aminopurin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol

InChIKey

OIRDTQYFTABQOQ-KQYNXXCUSA-N

INCHI

1S/C10H13N5O4/c11-8-5-9(13-2-12-8)15(3-14-5)10-7(18)6(17)4(1-16)19-10/h2-4,6-7,10,16-18H,1H2,(H2,11,12,13)/t4-,6-,7-,10-/m1/s1

Isomeric SMILES

C1=NC(=C2C(=N1)N(C=N2)[C@H]3[C@@H]([C@@H]([C@H](O3)CO)O)O)N

WGK Germany

2

RTECS

AU7175000

Molecular Weight

267.24

Beilstein

93029

Reaxy-Rn

1224871

Reaxys-RN_link_address

https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=1224871&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Nucleosides, nucleotides, and analogues
    • Class Purine nucleosides

• Kingdom: Organic compounds
• Superclass: Nucleosides, nucleotides, and analogues
• Class: Purine nucleosides
• Subclass: Not available
• Intermediate Tree Nodes: Not available
• Direct Parent: Purine nucleosides
• Alternative Parents: Glycosylamines Pentoses 6-aminopurines Aminopyrimidines and derivatives N-substituted imidazoles Imidolactams Tetrahydrofurans Heteroaromatic compounds Secondary alcohols Oxacyclic compounds Azacyclic compounds Primary amines Primary alcohols Organopnictogen compounds Hydrocarbon derivatives
• Molecular Framework: Aromatic heteropolycyclic compounds
• Substituents: Purine nucleoside - Glycosyl compound - N-glycosyl compound - 6-aminopurine - Pentose monosaccharide - Imidazopyrimidine - Purine - Aminopyrimidine - Monosaccharide - N-substituted imidazole - Pyrimidine - Imidolactam - Tetrahydrofuran - Azole - Imidazole - Heteroaromatic compound - Secondary alcohol - Organoheterocyclic compound - Azacycle - Oxacycle - Organic oxygen compound - Organic nitrogen compound - Alcohol - Organonitrogen compound - Hydrocarbon derivative - Organopnictogen compound - Organooxygen compound - Amine - Primary alcohol - Primary amine - Aromatic heteropolycyclic compound
• Description: This compound belongs to the class of organic compounds known as purine nucleosides. These are compounds comprising a purine base attached to a ribosyl or deoxyribosyl moiety.
• External Descriptors: Ribonucleosides

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

• Solubility: Solvent:water, Max Conc. mg/mL: 2.67, Max Conc. mM: 10; Solvent:DMSO, Max Conc. mg/mL: 20.04, Max Conc. mM: 75
• Sensitivity: Air sensitive
• Specific Rotation[α]: -70 ° (C=2, 5% NaOH)
• Melt Point(°C): 234-236°C
• Molecular Weight: 267.240 g/mol
• XLogP3: -1.100
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 2
• Exact Mass: 267.097 Da
• Monoisotopic Mass: 267.097 Da
• Topological Polar Surface Area: 140.000 Ų
• Heavy Atom Count: 19
• Formal Charge: 0
• Complexity: 335.000
• 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