Xanthosine - ≥98%(HPLC) , CAS No.146-80-5

CAS: 146-80-5 Cat. No.: X131750 Molecular Weight: 284.23 PubChem CID: 64959

GRADE & PURITY ≥98%(HPLC)

Synonyms

9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-3H-purine-2,6-dione | beta-D-Ribofuranoside, xanthine-9 | 3,9-Dihydro-9-beta-delta-ribofuranosyl-1H-purine-2,6-dione | 9 beta-D-ribofuranosylxanthine

Storage

Store at 2-8°C,Argon charged

Shipped In

Wet ice

Specifications

Synonyms

9-[(2R, 3R, 4S, 5R)-3, 4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-3H-purine-2, 6-dione | beta-D-Ribofuranoside, xanthine-9 | 3, 9-Dihydro-9-beta-delta-ribofuranosyl-1H-purine-2, 6-dione | 9 beta-D-ribofuranosylxanthine

Specifications & Purity

≥98%(HPLC)

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.

Purity

≥98%(HPLC)

Names and Identifiers

• Pubchem Sid: 504753936
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/504753936
• Canonical Smiles: C1=NC2=C(N1C3C(C(C(O3)CO)O)O)NC(=O)NC2=O
• IUPAC Name: 9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-3H-purine-2,6-dione
• InChIKey: UBORTCNDUKBEOP-UUOKFMHZSA-N
• INCHI: 1S/C10H12N4O6/c15-1-3-5(16)6(17)9(20-3)14-2-11-4-7(14)12-10(19)13-8(4)18/h2-3,5-6,9,15-17H,1H2,(H2,12,13,18,19)/t3-,5-,6-,9-/m1/s1
• Isomeric SMILES: C1=NC2=C(N1[C@H]3[C@@H]([C@@H]([C@H](O3)CO)O)O)NC(=O)NC2=O
• PubChem CID: 64959
• Molecular Weight: 284.23
• Reaxy-Rn: 625906

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: Xanthines Glycosylamines 6-oxopurines Pentoses Alkaloids and derivatives Pyrimidones N-substituted imidazoles Vinylogous amides Tetrahydrofurans Heteroaromatic compounds Ureas Secondary alcohols Lactams Oxacyclic compounds Azacyclic compounds Hydrocarbon derivatives Organic oxides Organonitrogen compounds Organopnictogen compounds Primary alcohols
• Molecular Framework: Aromatic heteropolycyclic compounds
• Substituents: Purine nucleoside - Glycosyl compound - N-glycosyl compound - Xanthine - 6-oxopurine - Purinone - Pentose monosaccharide - Purine - Imidazopyrimidine - Alkaloid or derivatives - Pyrimidone - Pyrimidine - Monosaccharide - N-substituted imidazole - Imidazole - Heteroaromatic compound - Tetrahydrofuran - Azole - Vinylogous amide - Lactam - Urea - Secondary alcohol - Organoheterocyclic compound - Azacycle - Oxacycle - Organooxygen compound - Organonitrogen compound - Organic nitrogen compound - Hydrocarbon derivative - Organic oxide - Organopnictogen compound - Organic oxygen compound - Alcohol - Primary alcohol - 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: Purine alkaloids

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(non-human)

J774.A1 (2436 Activities)

Explore this target

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

Mechanisms of Action

Chemical and Physical Properties

• Sensitivity: Hygroscopic
• Specific Rotation[α]: -59° (C=1,0.1mol/L NaOH sol.)
• Molecular Weight: 284.230 g/mol
• XLogP3: -2.400
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 2
• Exact Mass: 284.076 Da
• Monoisotopic Mass: 284.076 Da
• Topological Polar Surface Area: 146.000 Ų
• Heavy Atom Count: 20
• Formal Charge: 0
• Complexity: 434.000
• 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

References

1. Ran Xin, Meng Dong, Yu-Ying Zhang, Xu-Hui Huang, Xiu-Ping Dong, Lei Qin.  (2023)  Development and validation of a HILIC-MS/MS method for simultaneous quantitative of taste-active compounds in foods.  JOURNAL OF FOOD COMPOSITION AND ANALYSIS,      [PMID:] [10.1016/j.jfca.2023.105302]

2. Guorong Cheng, Zhiqiang Liu, Zhong Zheng, Fengrui Song, Xiaoyu Zhuang, Shu Liu.  (2022)  Cell Metabolomics Reveals the Potential Mechanism of Aloe Emodin and Emodin Inhibiting Breast Cancer Metastasis.  INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES,  23  (22): (13738).  [PMID:36430215] [10.3390/ijms232213738]

3. Ting Yang, Bangbang Wei, Jing Liu, Xinxin Si, Lulu Wang, Chunming Jiang.  (2024)  A landscape of metabolic variation among clinical outcomes of peritoneal dialysis in end-stage renal disease.  CLINICA CHIMICA ACTA,      [PMID:38342423] [10.1016/j.cca.2024.117826]

4. Wen Xie, Yajing Zhang, Yu He, Hang Su, Jinni Zhang, Canrong Chen, Peisi Xie, Jing Chen, Zian Lin, Zongwei Cai.  (2025)  Dietary Exposure to Imidacloprid at Environmental Doses Induces Renal Injury in Mice via P-AMPK Inhibition and Subsequent Purine Metabolism Dysregulation.  ENVIRONMENTAL SCIENCE & TECHNOLOGY,      [PMID:40899512] [10.1021/acs.est.5c05893]