xanthinol (CED0020302)

Record Information
Version1.0
Creation Date2016-06-03 10:04:07 UTC
Update Date2026-08-19 02:25:21 UTC
Accession NumberCHEM042665
Identification
Common Namexanthinol
ClassSmall Molecule
Description
Xanthinol is an organic compound with the chemical formula C13H21N5O4 and an average molecular weight of 311.34 g/mol. It is classified as an organoheterocyclic compound. Specifically, xanthinol belongs to the purines and purine derivatives, a subclass of imidazopyrimidines within the organic compounds. The compound is found in or released from six recorded sources. These include healthcare, pharmaceuticals, and veterinary products, where it is used as a peripheral vasodilator. It is also associated with electrical and electronic equipment, specifically electrically stimulated smoking devices, as well as household cleaning and consumer products such as perfumes within detergents and soaps, non-electric simulated smoking devices, and tobacco smoke filters. Additionally, it is present in indoor air, dust, and atmospheric transport. Recorded routes of exposure for xanthinol include oral and inhalation. In terms of biological activity, xanthinol interacts with six recorded protein targets. It serves as a binder or cofactor for the large ribosomal subunit protein uL3 (RPL3) and the mitochondrial NAD(P) transhydrogenase (NNT). Other protein targets include glyceraldehyde-3-phosphate dehydrogenase (GAPDH), the mitochondrial isocitrate dehydrogenase [NAD] subunit alpha (IDH3A), and two other proteins.
Contaminant TypeNot Available
Chemical Structure
Synonyms
ValueSource
JupalMeSH
Chemical FormulaC13H21N5O4
Average Molecular Mass311.342 g/mol
Monoisotopic Mass311.159 g/mol
CAS Registry Number2530-97-4
IUPAC Name7-{2-hydroxy-3-[(2-hydroxyethyl)(methyl)amino]propyl}-1,3-dimethyl-2,3,6,7-tetrahydro-1H-purine-2,6-dione
Traditional Namexanthinol
SMILESCN(CCO)CC(O)CN1C=NC2=C1C(=O)N(C)C(=O)N2C
InChI IdentifierInChI=1S/C13H21N5O4/c1-15(4-5-19)6-9(20)7-18-8-14-11-10(18)12(21)17(3)13(22)16(11)2/h8-9,19-20H,4-7H2,1-3H3
InChI KeyDSFGXPJYDCSWTA-UHFFFAOYSA-N
Chemical Taxonomy
Description 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.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassImidazopyrimidines
Sub ClassPurines and purine derivatives
Direct ParentXanthines
Alternative Parents
Substituents
  • Xanthine
  • 6-oxopurine
  • Purinone
  • Alkaloid or derivatives
  • Pyrimidone
  • N-substituted imidazole
  • Pyrimidine
  • Heteroaromatic compound
  • Azole
  • Imidazole
  • Vinylogous amide
  • Lactam
  • Urea
  • 1,2-aminoalcohol
  • Secondary alcohol
  • Tertiary amine
  • Tertiary aliphatic amine
  • Azacycle
  • Alkanolamine
  • Primary alcohol
  • Organooxygen compound
  • Organonitrogen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Organic nitrogen compound
  • Alcohol
  • Amine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Organoleptic EffectsNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility17.3 g/LALOGPS
logP-1ALOGPS
logP-1.8ChemAxon
logS-1.2ALOGPS
pKa (Strongest Acidic)14.38ChemAxon
pKa (Strongest Basic)8.86ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area102.14 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity80.11 m³·mol⁻¹ChemAxon
Polarizability31.95 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrumsplash10-052o-9440000000-a8d9629fcf2b57351e3dNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-03e9-1943000000-ea52103100f00cdc7b49Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-03dl-0098000000-0d0454c61c58ee3d3707Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-000f-2191000000-58d56af52994b6086825Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0080-5940000000-98bb262e668a27d708e7Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-03dl-1298000000-568ebc36338536f74734Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-004i-2920000000-7313907d0b900b1de739Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-03k9-6900000000-589ae3ea2272ef9ee74dNot AvailableView Spectrum
1D NMR13C NMR Spectrum (1D, D2O, predicted)Not AvailableNot AvailableView Spectrum
1D NMR1H NMR Spectrum (1D, D2O, predicted)Not AvailableNot AvailableView Spectrum
Toxicity Profile
Mechanism of ToxicityNot Available
Carcinogenicity (IARC Classification)Not Available
Minimum Risk LevelNot Available
SymptomsNot Available
TreatmentNot Available
Toxicity Values
Toxicity ValueUnitValue RangeOrganismDose DescriptorRoute of ExposurePredicted or ExperimentalReference
3171.0Log mg/kg[1800:5600]RatLD50oralpredictedNot Available
Health Effects
Health EffectRelationshipDirectionReference
Exposure Sources
Source IDSourceSectorReference
19Indoor airAir, dust & atmospheric transportNot Available
291Peripheral vasodilatorsHealthcare, pharmaceuticals & veterinary productsNot Available
518Electrically Stimulated Smoking DevicesElectrical & Electronic EquipmentNot Available
559Non Electric Simulated Smoking DevicesHousehold cleaning & consumer productsNot Available
561Perfumes Within Detergents And SoapsHousehold cleaning & consumer productsNot Available
569Tobacco Smoke FiltersHousehold cleaning & consumer productsNot Available
580Manufacture Preparation Of Tobacco ProductsIndustrial manufacturing & chemical processingNot Available
611Anti Perspirants Or Body DeoderantsPersonal care & cosmeticsNot Available
Pathways
1 pathway
Targets
StructureProteinUniProt IDOrganismRelationshipDetails
Adenosine receptor A2b structureClick to view 3D structureAdenosine receptor A2bP29275HumansPredicted (SEA)42.1164
Click to view 3D structureAdenosine receptor A2aP46616Cavia porcellusPredicted (SEA)13.3901
Click to view 3D structureAdenosine receptor A1P25099Rattus norvegicusPredicted (SEA)68.8187
Click to view 3D structureAdenosine receptor A2aP30543Rattus norvegicusPredicted (SEA)65.6269
Click to view 3D structure5-hydroxytryptamine receptor 1AP19327Rattus norvegicusPredicted (SEA)259.316
5-hydroxytryptamine receptor 7 structureClick to view 3D structure5-hydroxytryptamine receptor 7P34969HumansPredicted (SEA)274.73
Click to view 3D structureD(2) dopamine receptorP61169RatPredicted (SEA)364.957
Adenosine receptor A2a structureClick to view 3D structureAdenosine receptor A2aP29274HumansPredicted (SEA)161.537
CCR4-NOT transcription complex subunit 7 structureClick to view 3D structureCCR4-NOT transcription complex subunit 7Q9UIV1HumansPredicted (SEA)2.17978
Amine oxidase [flavin-containing] B structureClick to view 3D structureAmine oxidase [flavin-containing] BP27338HumansPredicted (SEA)258.459
Adenosine receptor A1 structureClick to view 3D structureAdenosine receptor A1P30542HumansPredicted (SEA)159.902
Click to view 3D structure5-hydroxytryptamine receptor 2AP14842Rattus norvegicusPredicted (SEA)358.34
Amine oxidase [flavin-containing] A structureClick to view 3D structureAmine oxidase [flavin-containing] AP21397HumansPredicted (SEA)208.247
Click to view 3D structureAdenosine receptor A2bP29276Rattus norvegicusPredicted (SEA)23.1212
Adenosine receptor A3 structureClick to view 3D structureAdenosine receptor A3P0DMS8HumansPredicted (SEA)437.046
5'-3' exonuclease PLD3 structureClick to view 3D structure5'-3' exonuclease PLD3Q8IV08HumansPredicted (SEA)13.5458
5-hydroxytryptamine receptor 6 structureClick to view 3D structure5-hydroxytryptamine receptor 6P50406HumansPredicted (SEA)856.03
Endochitinase B1 structureClick to view 3D structureEndochitinase B1Q873X9Neosartorya fumigataPredicted (SEA)1.40129
G-protein coupled receptor 55 structureClick to view 3D structureG-protein coupled receptor 55Q9Y2T6HumansPredicted (SEA)249.585
Click to view 3D structureN-arachidonyl glycine receptorQ14330HumansPredicted (SEA)46.7095
Acetylcholinesterase structureClick to view 3D structureAcetylcholinesteraseP22303HumansPredicted (SEA)1333.25
Muscarinic acetylcholine receptor M2 structureClick to view 3D structureMuscarinic acetylcholine receptor M2P08172HumansPredicted (SEA)1425.73
Click to view 3D structureActin nucleation-promoting factor WASLO08816Rattus norvegicusPredicted (SEA)5.60514
D(2) dopamine receptor structureClick to view 3D structureD(2) dopamine receptorP14416HumansPredicted (SEA)3016.66
Muscarinic acetylcholine receptor M1 structureClick to view 3D structureMuscarinic acetylcholine receptor M1P11229HumansPredicted (SEA)1686.45
Concentrations
Not Available
External Links
DrugBank IDDB09092
HMDB IDHMDB0259919
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDC00023037
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkXanthinol
Chemspider ID9526
ChEBI IDNot Available
PubChem Compound IDNot Available
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References