Oxypurinol - ≥98%(HPLC) , Xanthine dehydrogenase inhibitor, CAS No.2465-59-0, Xanthine dehydrogenase inhibitor

CAS: 2465-59-0 Cat. No.: O168987 Molecular Weight: 152.11 EC Number: 219-570-9

GRADE & PURITY ≥98%(HPLC)

Synonyms

(1R,2R,4S,5S,7s)-9-methyl-3-oxa-9-azatricyclo[3.3.1.02,4]nonan-7-yl (S)-3-hydroxy-2-phenylpropanoate | Alloxanthin (VAN) | B. W. 55-5 | 1H,3H,9H-Alloxanthine | Oxipurinolum [INN-Latin] | CCG-321461 | DTXSID4035209 | Oxipurinol | Oxipurinol [INN] | D02365

Storage

Room temperature

Shipped In

Normal

Overview

Oxypurinol has been used as a xanthine oxidase inhibitor, to evaluate its effects on hepatocellular carcinoma cell proliferation. It has also been used as a xanthine inhibitor to elucidate its contribution in the induction of hpv16 late gene expression. Oxypurinol, an allopurinol metabolite, is used as an inhibitor to study the specificity and kinetics of of xanthine oxidase(s). Oxypurinol is also used as an anti-inflammatory agent via inhibition of xanthine oxidase.

Specifications

Synonyms

(1R, 2R, 4S, 5S, 7s)-9-methyl-3-oxa-9-azatricyclo[3.3.1.02, 4]nonan-7-yl (S)-3-hydroxy-2-phenylpropanoate | Alloxanthin (VAN) | B. W. 55-5 | 1H, 3H, 9H-Alloxanthine | Oxipurinolum [INN-Latin] | CCG-321461 | DTXSID4035209 | Oxipurinol | Oxipurinol [INN] | D02365

Specifications & Purity

≥98%(HPLC)

Storage

Room temperature

Shipped In

Normal

Action Type

INHIBITOR

Mechanism of action

Xanthine dehydrogenase inhibitor

Purity

≥98%(HPLC)

Names and Identifiers

• Pubchem Sid: 488202828
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/488202828
• Canonical Smiles: C1=NNC2=C1C(=O)NC(=O)N2
• IUPAC Name: 1,7-dihydropyrazolo[3,4-d]pyrimidine-4,6-dione
• InChIKey: HXNFUBHNUDHIGC-UHFFFAOYSA-N
• INCHI: 1S/C5H4N4O2/c10-4-2-1-6-9-3(2)7-5(11)8-4/h1H,(H3,6,7,8,9,10,11)
• Isomeric SMILES: C1=NNC2=C1C(=O)NC(=O)N2
• Molecular Weight: 152.11
• Reaxy-Rn: 139956
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=139956&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organoheterocyclic compounds
    • Class Imidazopyrimidines
      • Subclass Purines and purine derivatives

• Kingdom: Organic compounds
• Superclass: Organoheterocyclic compounds
• Class: Imidazopyrimidines
• Subclass: Purines and purine derivatives
• Intermediate Tree Nodes: Not available
• Direct Parent: Xanthines
• Alternative Parents: Pyrazolo[3,4-d]pyrimidines Alkaloids and derivatives Pyrimidones Vinylogous amides Pyrazoles Heteroaromatic compounds Lactams Azacyclic compounds Organopnictogen compounds Organooxygen compounds Organonitrogen compounds Organic oxides Hydrocarbon derivatives
• Molecular Framework: Aromatic heteropolycyclic compounds
• Substituents: Xanthine - Pyrazolopyrimidine - Pyrazolo[3,4-d]pyrimidine - Alkaloid or derivatives - Pyrimidone - Pyrimidine - Azole - Pyrazole - Vinylogous amide - Heteroaromatic compound - Lactam - Azacycle - Organic oxide - Organopnictogen compound - Organic oxygen compound - Organic nitrogen compound - Organooxygen compound - Hydrocarbon derivative - Organonitrogen compound - Aromatic heteropolycyclic compound
• Description: This compound belongs to the class of organic compounds known as xanthines. These are purine derivatives with a ketone group conjugated at carbons 2 and 6 of the purine moiety.
• External Descriptors: C40 isoprenoids (tetraterpenes)

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)

XDH Tclin Xanthine dehydrogenase/oxidase (2 Activities)

Discover Target: XDH

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

XDH Tclin Xanthine dehydrogenase (1038 Activities)

Discover Target: XDH

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

GMNN Tbio Geminin (128009 Activities)

Discover Target: GMNN

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

Associated Targets(non-human)

ampC Beta-lactamase AmpC (62480 Activities)

Discover Target: ampC

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

Pnp Purine nucleoside phosphorylase (4 Activities)

Discover Target: Pnp

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

rep Replicase polyprotein 1ab (378 Activities)

Discover Target: rep

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

Txnrd1 Thioredoxin reductase 1, cytoplasmic (45279 Activities)

Discover Target: Txnrd1

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 DMSO
• Melt Point(°C): >300℃
• Molecular Weight: 152.110 g/mol
• XLogP3: -0.900
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 152.033 Da
• Monoisotopic Mass: 152.033 Da
• Topological Polar Surface Area: 86.900 Ų
• Heavy Atom Count: 11
• Formal Charge: 0
• Complexity: 217.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• 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. Xue-Ting Shao, Yue-Tong Zhao, Bing Jiang, Yan-Ying Li, Jian-Guo Lin, De-Gao Wang.  (2023)  Evaluation of Three Chronic Diseases by Selected Biomarkers in Wastewater.  ACS ES&T Water,      [PMID:] [10.1021/acsestwater.2c00452]