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Identification
NameXanthine
Accession NumberDB02134  (EXPT03251)
TypeSmall Molecule
GroupsExperimental
Description

A purine base found in most body tissues and fluids, certain plants, and some urinary calculi. It is an intermediate in the degradation of adenosine monophosphate to uric acid, being formed by oxidation of hypoxanthine. The methylated xanthine compounds caffeine, theobromine, and theophylline and their derivatives are used in medicine for their bronchodilator effects. (Dorland, 28th ed)

Structure
Thumb
SynonymsNot Available
SaltsNot Available
Brand namesNot Available
Brand mixturesNot Available
CategoriesNot Available
CAS number69-89-6
WeightAverage: 152.1109
Monoisotopic: 152.033425392
Chemical FormulaC5H4N4O2
InChI KeyLRFVTYWOQMYALW-UHFFFAOYSA-N
InChI
InChI=1S/C5H4N4O2/c10-4-2-3(7-1-6-2)8-5(11)9-4/h1H,(H3,6,7,8,9,10,11)
IUPAC Name
2,3,6,7-tetrahydro-1H-purine-2,6-dione
SMILES
O=C1NC2=C(NC=N2)C(=O)N1
Mass SpecNot Available
Taxonomy
KingdomOrganic Compounds
SuperclassHeterocyclic Compounds
ClassImidazopyrimidines
SubclassPurines and Purine Derivatives
Direct parentXanthines
Alternative parentsPurinones; Pyrimidones; Imidazoles; Polyamines
Substituentspyrimidone; pyrimidine; imidazole; azole; polyamine; organonitrogen compound
Classification descriptionThis compound belongs to the xanthines. These are purine derivatives with a ketone group conjugated at carbons 2 and 6 of the purine moiety.
Pharmacology
IndicationNot Available
PharmacodynamicsNot Available
Mechanism of actionNot Available
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
Metabolism
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organismsNot Available
Pathways
PathwayCategorySMPDB ID
Molybdenium Cofactor DeficiencyDiseaseSMP00203
Purine Nucleoside Phosphorylase DeficiencyDiseaseSMP00210
Mitochondrial DNA depletion syndromeDiseaseSMP00536
Purine MetabolismMetabolicSMP00050
Adenylosuccinate Lyase DeficiencyDiseaseSMP00167
Gout or Kelley-Seegmiller SyndromeDiseaseSMP00365
Xanthinuria type IDiseaseSMP00512
Lesch-Nyhan Syndrome (LNS)DiseaseSMP00364
Xanthine Dehydrogenase Deficiency (Xanthinuria)DiseaseSMP00220
Xanthinuria type IIDiseaseSMP00513
Adenine phosphoribosyltransferase deficiency (APRT)DiseaseSMP00535
Adenosine Deaminase DeficiencyDiseaseSMP00144
AICA-RibosiduriaDiseaseSMP00168
Myoadenylate deaminase deficiencyDiseaseSMP00537
Azathioprine Action PathwayDrug actionSMP00427
Mercaptopurine Action PathwayDrug actionSMP00428
Thioguanine Action PathwayDrug actionSMP00430
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
Property Value Probability
Human Intestinal Absorption + 0.9923
Blood Brain Barrier + 0.9833
Caco-2 permeable - 0.7704
P-glycoprotein substrate Non-substrate 0.6282
P-glycoprotein inhibitor I Non-inhibitor 0.9619
P-glycoprotein inhibitor II Non-inhibitor 0.9953
Renal organic cation transporter Non-inhibitor 0.9279
CYP450 2C9 substrate Non-substrate 0.7781
CYP450 2D6 substrate Non-substrate 0.7434
CYP450 3A4 substrate Non-substrate 0.7417
CYP450 1A2 substrate Inhibitor 0.575
CYP450 2C9 substrate Non-inhibitor 0.8946
CYP450 2D6 substrate Non-inhibitor 0.9138
CYP450 2C19 substrate Non-inhibitor 0.8748
CYP450 3A4 substrate Non-inhibitor 0.8998
CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9936
Ames test Non AMES toxic 0.8008
Carcinogenicity Non-carcinogens 0.9579
Biodegradation Ready biodegradable 0.5112
Rat acute toxicity 2.1045 LD50, mol/kg Not applicable
hERG inhibition (predictor I) Weak inhibitor 0.938
hERG inhibition (predictor II) Non-inhibitor 0.9412
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
Statesolid
Experimental Properties
PropertyValueSource
water solubility69 mg/L (at 16 °C)MERCK INDEX (1996)
logP-0.73HANSCH,C ET AL. (1995)
pKa7.53KORTUM,G ET AL (1961)
Predicted Properties
PropertyValueSource
Water Solubility4.91ALOGPS
logP-0.65ALOGPS
logP-0.21ChemAxon
logS-1.5ALOGPS
pKa (Strongest Acidic)7.95ChemAxon
pKa (Strongest Basic)-0.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area86.88 Å2ChemAxon
Rotatable Bond Count0ChemAxon
Refractivity36.92 m3·mol-1ChemAxon
Polarizability12.7 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
SpectraGC-MSMS/MSLC-MS1D NMR2D NMR
References
Synthesis Reference

John P. Zikakis, “Preparation of high purity xanthine oxidase from bovine milk.” U.S. Patent US4172763, issued October 30, 1979.

US4172763
General ReferenceNot Available
External Links
ResourceLink
KEGG CompoundC00385
PubChem Compound1188
PubChem Substance46507575
ChemSpider1151
ChEBI17712
ChEMBL
Therapeutic Targets DatabaseDCL000293
HETXAN
WikipediaXanthine
ATC CodesNot Available
AHFS CodesNot Available
PDB Entries
FDA labelNot Available
MSDSNot Available
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

Targets

1. Purine nucleoside phosphorylase 2

Kind: protein

Organism: Escherichia coli (strain K12)

Pharmacological action: unknown

Components

Name UniProt ID Details
Purine nucleoside phosphorylase 2 P45563 Details

References:

  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed

2. Xanthine phosphoribosyltransferase

Kind: protein

Organism: Escherichia coli (strain K12)

Pharmacological action: unknown

Components

Name UniProt ID Details
Xanthine phosphoribosyltransferase P0A9M5 Details

References:

  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed

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Drug created on June 13, 2005 07:24 / Updated on September 16, 2013 17:17