Xanthine

Identification

Name
Xanthine
Accession Number
DB02134  (EXPT03251)
Type
Small Molecule
Groups
Experimental
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
Synonyms
Not Available
External IDs
NSC-14664
Categories
UNII
1AVZ07U9S7
CAS number
69-89-6
Weight
Average: 152.1109
Monoisotopic: 152.033425392
Chemical Formula
C5H4N4O2
InChI Key
LRFVTYWOQMYALW-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

Indication
Not Available
Structured Indications
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UPurine nucleoside phosphorylase 2Not AvailableEscherichia coli (strain K12)
UXanthine phosphoribosyltransferaseNot AvailableEscherichia coli (strain K12)
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity
Not Available
Affected organisms
Not Available
Pathways
PathwayCategory
Lesch-Nyhan Syndrome (LNS)Disease
Myoadenylate deaminase deficiencyDisease
Gout or Kelley-Seegmiller SyndromeDisease
Azathioprine Action PathwayDrug action
Xanthinuria type IIDisease
Purine MetabolismMetabolic
Adenosine Deaminase DeficiencyDisease
Xanthine Dehydrogenase Deficiency (Xanthinuria)Disease
AICA-RibosiduriaDisease
Mercaptopurine Action PathwayDrug action
Thioguanine Action PathwayDrug action
Xanthinuria type IDisease
Adenylosuccinate Lyase DeficiencyDisease
Molybdenum Cofactor DeficiencyDisease
Purine Nucleoside Phosphorylase DeficiencyDisease
Adenine phosphoribosyltransferase deficiency (APRT)Disease
Mitochondrial DNA depletion syndromeDisease
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not 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 References
Not Available
External Links
Human Metabolome Database
HMDB00292
KEGG Compound
C00385
PubChem Compound
1188
PubChem Substance
46507575
ChemSpider
1151
BindingDB
82009
ChEBI
17712
ChEMBL
CHEMBL1424
Therapeutic Targets Database
DCL000293
HET
XAN
Wikipedia
Xanthine
ATC Codes
Not Available
AHFS Codes
Not Available
PDB Entries
FDA label
Not Available
MSDS
Not Available

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
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 FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
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 )

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)GC-MSsplash10-0f6t-0924000000-9b80e0a2a60c73ca0180
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-0f6t-0924000000-9b80e0a2a60c73ca0180
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-0f6t-0924000000-30dc5892eecde860846a
Mass Spectrum (Electron Ionization)MSsplash10-0udi-7900000000-2d5ab5d5db8ff4981467
MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)LC-MS/MSsplash10-0udi-0900000000-a70539989d121bfacee0
MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)LC-MS/MSsplash10-0a4i-6900000000-b047b06406308dbaeda8
MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)LC-MS/MSsplash10-0a4i-9300000000-ed480ed920c3e9b576ec
LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , NegativeLC-MS/MSsplash10-0zfr-0900000000-efb049914c9bce596267
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0udi-0900000000-2e9e069e2df414aed037
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0w29-0900000000-fa52193346bc456d89e8
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0a5i-9400000000-bbf70998e8b7515cb440
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0udi-0900000000-566d663553ce4f0ec207
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0zfr-1900000000-d0a5d2c0f89f8d42d903
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0006-9000000000-351d9f8ee3470f911829
LC-MS/MS Spectrum - LC-ESI-QTOF , negativeLC-MS/MSsplash10-0zfr-0900000000-efb049914c9bce596267
MS/MS Spectrum - , negativeLC-MS/MSsplash10-0udi-0900000000-5fee91293851bb02193e
LC-MS/MS Spectrum - LC-ESI-IT , positiveLC-MS/MSsplash10-000i-0900000000-4568a814903ff411923a
1H NMR Spectrum1D NMRNot Applicable
13C NMR Spectrum1D NMRNot Applicable
1H NMR Spectrum1D NMRNot Applicable
13C NMR Spectrum1D NMRNot Applicable
[1H,1H] 2D NMR Spectrum2D NMRNot Applicable
[1H,13C] 2D NMR Spectrum2D NMRNot Applicable

Taxonomy

Description
This compound belongs to the class of chemical entities known as xanthines. These are purine derivatives with a ketone group conjugated at carbons 2 and 6 of the purine moiety.
Kingdom
Chemical entities
Super Class
Organic compounds
Class
Organoheterocyclic compounds
Sub Class
Imidazopyrimidines
Direct Parent
Xanthines
Alternative Parents
6-oxopurines / Alkaloids and derivatives / Pyrimidones / Vinylogous amides / Imidazoles / Heteroaromatic compounds / Ureas / Lactams / Azacyclic compounds / Organopnictogen compounds
show 4 more
Substituents
Xanthine / 6-oxopurine / Purinone / Alkaloid or derivatives / Pyrimidone / Pyrimidine / Azole / Imidazole / Heteroaromatic compound / Vinylogous amide
show 11 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
xanthine (CHEBI:17712 ) / Purine alkaloids (C00385 ) / a small molecule (XANTHINE )

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 ...
Gene Name
xapA
Uniprot ID
P45563
Uniprot Name
Purine nucleoside phosphorylase 2
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
Uniprot Name
Xanthine phosphoribosyltransferase
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 ]

Drug created on June 13, 2005 07:24 / Updated on October 02, 2017 05:07