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Identification
NameXanthine
Accession NumberDB02134  (EXPT03251)
TypeSmall Molecule
GroupsExperimental
DescriptionA 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
External Identifiers Not Available
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International BrandsNot Available
Brand mixturesNot Available
SaltsNot Available
Categories
UNII1AVZ07U9S7
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
Pharmacology
IndicationNot Available
Structured Indications Not Available
PharmacodynamicsNot Available
Mechanism of action
TargetKindPharmacological actionActionsOrganismUniProt ID
Purine nucleoside phosphorylase 2ProteinunknownNot AvailableEscherichia coli (strain K12)P45563 details
Xanthine phosphoribosyltransferaseProteinunknownNot AvailableEscherichia coli (strain K12)P0A9M5 details
Related Articles
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organismsNot Available
Pathways
PathwayCategorySMPDB ID
Lesch-Nyhan Syndrome (LNS)DiseaseSMP00364
Myoadenylate deaminase deficiencyDiseaseSMP00537
Gout or Kelley-Seegmiller SyndromeDiseaseSMP00365
Azathioprine Action PathwayDrug actionSMP00427
Xanthinuria type IIDiseaseSMP00513
Purine MetabolismMetabolicSMP00050
Adenosine Deaminase DeficiencyDiseaseSMP00144
Xanthine Dehydrogenase Deficiency (Xanthinuria)DiseaseSMP00220
Adenylosuccinate Lyase DeficiencyDiseaseSMP00167
Molybdenum Cofactor DeficiencyDiseaseSMP00203
Purine Nucleoside Phosphorylase DeficiencyDiseaseSMP00210
Adenine phosphoribosyltransferase deficiency (APRT)DiseaseSMP00535
Mitochondrial DNA depletion syndromeDiseaseSMP00536
AICA-RibosiduriaDiseaseSMP00168
Mercaptopurine Action PathwayDrug actionSMP00428
Thioguanine Action PathwayDrug actionSMP00430
Xanthinuria type IDiseaseSMP00512
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available
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 ReferencesNot Available
External Links
ATC CodesNot Available
AHFS CodesNot Available
PDB Entries
FDA labelNot Available
MSDSNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9923
Blood Brain Barrier+0.9833
Caco-2 permeable-0.7704
P-glycoprotein substrateNon-substrate0.6282
P-glycoprotein inhibitor INon-inhibitor0.9619
P-glycoprotein inhibitor IINon-inhibitor0.9953
Renal organic cation transporterNon-inhibitor0.9279
CYP450 2C9 substrateNon-substrate0.7781
CYP450 2D6 substrateNon-substrate0.7434
CYP450 3A4 substrateNon-substrate0.7417
CYP450 1A2 substrateInhibitor0.575
CYP450 2C9 inhibitorNon-inhibitor0.8946
CYP450 2D6 inhibitorNon-inhibitor0.9138
CYP450 2C19 inhibitorNon-inhibitor0.8748
CYP450 3A4 inhibitorNon-inhibitor0.8998
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9936
Ames testNon AMES toxic0.8008
CarcinogenicityNon-carcinogens0.9579
BiodegradationReady biodegradable0.5112
Rat acute toxicity2.1045 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.938
hERG inhibition (predictor II)Non-inhibitor0.9412
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
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 Solubility4.91 mg/mLALOGPS
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 FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)splash10-0f6t-0924000000-9b80e0a2a60c73ca0180View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MSNot Available
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0udi-0900000000-a70539989d121bfacee0View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0a4i-6900000000-b047b06406308dbaeda8View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0a4i-9300000000-ed480ed920c3e9b576ecView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-0zfr-0900000000-efb049914c9bce596267View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0900000000-2e9e069e2df414aed037View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0w29-0900000000-fa52193346bc456d89e8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a5i-9400000000-bbf70998e8b7515cb440View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0900000000-566d663553ce4f0ec207View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0zfr-1900000000-d0a5d2c0f89f8d42d903View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-351d9f8ee3470f911829View in MoNA
MSMass Spectrum (Electron Ionization)splash10-0udi-7900000000-2d5ab5d5db8ff4981467View in MoNA
1D NMR1H NMR SpectrumNot Available
1D NMR13C NMR SpectrumNot Available
1D NMR1H NMR SpectrumNot Available
1D NMR13C NMR SpectrumNot Available
2D NMR[1H,1H] 2D NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as alkaloids and derivatives. These are naturally occurring chemical compounds that contain mostly basic nitrogen atoms. This group also includes some related compounds with neutral and even weakly acidic properties. Also some synthetic compounds of similar structure are attributed to alkaloids. In addition to carbon, hydrogen and nitrogen, alkaloids may also contain oxygen, sulfur and more rarely other elements such as chlorine, bromine, and phosphorus.
KingdomOrganic compounds
Super ClassAlkaloids and derivatives
ClassNot Available
Sub ClassNot Available
Direct ParentAlkaloids and derivatives
Alternative Parents
Substituents
  • Alkaloid or derivatives
  • Xanthine
  • Purinone
  • Purine
  • Imidazopyrimidine
  • Hydroxypyrimidine
  • Pyrimidone
  • Pyrimidine
  • Heteroaromatic compound
  • Imidazole
  • Azole
  • Azacycle
  • Organoheterocyclic compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors

Targets

Kind
Protein
Organism
Escherichia coli (strain K12)
Pharmacological action
unknown
General Function:
Purine-nucleoside phosphorylase activity
Specific Function:
The purine nucleoside phosphorylases catalyze the phosphorolytic breakdown of the N-glycosidic bond in the beta-(deoxy)ribonucleoside molecules, with the formation of the corresponding free purine bases and pentose-1-phosphate. This protein can degrade all purine nucleosides including xanthosine, inosine and guanosine, but cannot cleave adenosine, deoxyadenosine or hypoxanthine arabinoside. Has...
Gene Name:
xapA
Uniprot ID:
P45563
Molecular Weight:
29834.38 Da
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:17139284 ]
  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:17016423 ]
Kind
Protein
Organism
Escherichia coli (strain K12)
Pharmacological action
unknown
General Function:
Xanthine phosphoribosyltransferase activity
Specific Function:
Acts on guanine, xanthine and to a lesser extent hypoxanthine.
Gene Name:
gpt
Uniprot ID:
P0A9M5
Molecular Weight:
16970.455 Da
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:17139284 ]
  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:17016423 ]
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Drug created on June 13, 2005 07:24 / Updated on August 17, 2016 12:23