Record Information
Version1.0
Creation date2011-09-21 00:18:21 UTC
Update date2020-09-17 15:41:40 UTC
Primary IDFDB022714
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameParaxanthine
DescriptionParaxanthine, also known as p-xanthine, 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. A dimethylxanthine having the two methyl groups located at positions 1 and 7. Paraxanthine is an extremely weak basic (essentially neutral) compound (based on its pKa). Paraxanthine exists in all living organisms, ranging from bacteria to humans. Within humans, paraxanthine participates in a number of enzymatic reactions. In particular, paraxanthine and formaldehyde can be biosynthesized from caffeine through the action of the enzyme cytochrome P450 1A2. In addition, paraxanthine and acetyl-CoA can be converted into 5-acetylamino-6-formylamino-3-methyluracil; which is catalyzed by the enzyme arylamine N-acetyltransferase 2. In humans, paraxanthine is involved in caffeine metabolism.
CAS Number611-59-6
Structure
Thumb
Synonyms
SynonymSource
3,7-Dihydro-1,7-dimethyl-1H-purine-2,6-dioneChEBI
p-XanthineChEBI
1,7-Dimethyl-xanthineHMDB
1,7-DimethylxanthineHMDB, MeSH
1,7-dimethyl-Xanthinehmdb
3,7-dihydro-1,7-Dimethyl-1H-purine-2,6-dioneChEBI
P-XanthineChEBI
Predicted Properties
PropertyValueSource
Water Solubility9.13 g/LALOGPS
logP-0.63ALOGPS
logP0.24ChemAxon
logS-1.3ALOGPS
pKa (Strongest Acidic)10.76ChemAxon
pKa (Strongest Basic)-0.87ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area67.23 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity46.72 m³·mol⁻¹ChemAxon
Polarizability16.87 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC7H8N4O2
IUPAC name1,7-dimethyl-2,3,6,7-tetrahydro-1H-purine-2,6-dione
InChI IdentifierInChI=1S/C7H8N4O2/c1-10-3-8-5-4(10)6(12)11(2)7(13)9-5/h3H,1-2H3,(H,9,13)
InChI KeyQUNWUDVFRNGTCO-UHFFFAOYSA-N
Isomeric SMILESCN1C=NC2=C1C(=O)N(C)C(=O)N2
Average Molecular Weight180.164
Monoisotopic Molecular Weight180.06472552
Classification
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
  • Hydroxypyrimidine
  • N-substituted imidazole
  • Pyrimidine
  • Imidazole
  • Azole
  • Heteroaromatic compound
  • Lactam
  • Azacycle
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic nitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Source:

Biological location:

Process

Naturally occurring process:

Role

Biological role:

Foods
  • Cocoa and cocoa products
  • Beverages:

    Physico-Chemical Properties - Experimental
    Physico-Chemical Properties - Experimental
    PropertyValueReference
    Physical stateSolid
    Physical DescriptionNot Available
    Mass CompositionNot Available
    Melting PointNot Available
    Boiling PointNot Available
    Experimental Water SolubilityNot Available
    Experimental logPNot Available
    Experimental pKaNot Available
    Isoelectric pointNot Available
    ChargeNot Available
    Optical RotationNot Available
    Spectroscopic UV DataNot Available
    DensityNot Available
    Refractive IndexNot Available
    Spectra
    Spectra
    EI-MS/GC-MS
    TypeDescriptionSplash KeyView
    GC-MSParaxanthine, non-derivatized, GC-MS Spectrumsplash10-000i-2980000000-6ee5dc3100885f205536Spectrum
    GC-MSParaxanthine, non-derivatized, GC-MS Spectrumsplash10-000i-2980000000-6ee5dc3100885f205536Spectrum
    Predicted GC-MSParaxanthine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0uka-3900000000-d979badf45de391835d4Spectrum
    Predicted GC-MSParaxanthine, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
    MS/MS
    TypeDescriptionSplash KeyView
    MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-001i-0900000000-2d1aa5f80618f452686cSpectrum
    MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-00di-0900000000-3326bcbee23b63dcc230Spectrum
    MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-014l-9000000000-9824aef9dc2f13c24bccSpectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-00e9-1900000000-9d0dde13bb1ce13e2644Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-00fr-0900000000-1aa733a1b7e41b994d8dSpectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-00di-1900000000-190ff3302e9f5a37a72fSpectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-00fr-0900000000-1aa733a1b7e41b994d8dSpectrum
    MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-0229-0900000000-729a2bed81ba15260ffaSpectrum
    MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-0229-0900000000-18d0a9c63a1dfb683c9bSpectrum
    MS/MSLC-MS/MS Spectrum - , negativesplash10-004i-0900000000-c52421f0ba1f46241853Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-IT , positivesplash10-00di-0900000000-0bd6ed3d764e5a9b374eSpectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-00e9-1900000000-9d0dde13bb1ce13e2644Spectrum
    MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-0w29-0940000000-127f99d8e7324e01eb66Spectrum
    MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-0ik9-0930000000-fe234438cbe3be0b30f6Spectrum
    MS/MSLC-MS/MS Spectrum - , positivesplash10-00di-1900000000-190ff3302e9f5a37a72fSpectrum
    MS/MSLC-MS/MS Spectrum - , positivesplash10-001i-0900000000-d6040ea84fe19d8c5cc6Spectrum
    MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-001i-0900000000-935e5a47dc1abe7b1196Spectrum
    MS/MSLC-MS/MS Spectrum - 35V, Positivesplash10-00di-3900000000-2f3998477ce19f3ff96fSpectrum
    MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-00di-4900000000-c89111b73e8a9a163111Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0900000000-5e7c398698bb5c16617dSpectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-1900000000-522eaddc21ef92e70e62Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0005-9200000000-d10a1141c0e21f56ec00Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-1900000000-bc2d3cb520a4fcb81529Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-2900000000-e2e2992ce9b1265af790Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-05am-9300000000-e1aefedceb8692ffe91fSpectrum
    NMR
    TypeDescriptionView
    1D NMR1H NMR SpectrumSpectrum
    1D NMR13C NMR SpectrumSpectrum
    1D NMR1H NMR SpectrumSpectrum
    1D NMR13C NMR SpectrumSpectrum
    1D NMR1H NMR SpectrumSpectrum
    1D NMR13C NMR SpectrumSpectrum
    1D NMR1H NMR SpectrumSpectrum
    1D NMR13C NMR SpectrumSpectrum
    1D NMR1H NMR SpectrumSpectrum
    1D NMR13C NMR SpectrumSpectrum
    1D NMR1H NMR SpectrumSpectrum
    1D NMR13C NMR SpectrumSpectrum
    1D NMR1H NMR SpectrumSpectrum
    1D NMR13C NMR SpectrumSpectrum
    1D NMR1H NMR SpectrumSpectrum
    1D NMR13C NMR SpectrumSpectrum
    1D NMR1H NMR SpectrumSpectrum
    1D NMR13C NMR SpectrumSpectrum
    1D NMR1H NMR SpectrumSpectrum
    1D NMR13C NMR SpectrumSpectrum
    1D NMR1H NMR SpectrumSpectrum
    2D NMR[1H,13C] 2D NMR SpectrumSpectrum
    ChemSpider ID4525
    ChEMBL IDCHEMBL1158
    KEGG Compound IDC13747
    Pubchem Compound ID4687
    Pubchem Substance IDNot Available
    ChEBI ID25858
    Phenol-Explorer IDNot Available
    DrugBank IDNot Available
    HMDB IDHMDB01860
    CRC / DFC (Dictionary of Food Compounds) IDNot Available
    EAFUS IDNot Available
    Dr. Duke IDNot Available
    BIGG IDNot Available
    KNApSAcK IDNot Available
    HET IDNot Available
    Food Biomarker OntologyNot Available
    VMH IDNot Available
    Flavornet IDNot Available
    GoodScent IDNot Available
    SuperScent IDNot Available
    Wikipedia IDParaxanthine
    Phenol-Explorer Metabolite IDNot Available
    Duplicate IDSNot Available
    Old DFC IDSNot Available
    Associated Foods
    FoodContent Range AverageReference
    FoodReference
    Biological Effects and Interactions
    Health Effects / BioactivitiesNot Available
    Enzymes
    NameGene NameUniProt ID
    Cytochrome P450, family 1, subfamily A, polypeptide 1CYP1A1A0N0X8
    Cytochrome P450 2D6CYP2D6Q6NWU0
    Arylamine N-acetyltransferase 1NAT1P18440
    Arylamine N-acetyltransferase 2NAT2P11245
    Pathways
    NameSMPDB LinkKEGG Link
    Caffeine MetabolismSMP00028 map00232
    MetabolismNot Available
    BiosynthesisNot Available
    Organoleptic Properties
    FlavoursNot Available
    Files
    MSDSshow
    References
    Synthesis ReferenceNot Available
    General ReferenceNot Available
    Content Reference