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-0900000000-2d1aa5f80618f452686c2012-07-24View Spectrum
    MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-00di-0900000000-3326bcbee23b63dcc2302012-07-24View Spectrum
    MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-014l-9000000000-9824aef9dc2f13c24bcc2012-07-24View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-00e9-1900000000-9d0dde13bb1ce13e26442012-08-31View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-00fr-0900000000-1aa733a1b7e41b994d8d2012-08-31View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-00di-1900000000-190ff3302e9f5a37a72f2017-09-14View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-00fr-0900000000-1aa733a1b7e41b994d8d2017-09-14View Spectrum
    MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-0229-0900000000-729a2bed81ba15260ffa2017-09-14View Spectrum
    MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-0229-0900000000-18d0a9c63a1dfb683c9b2017-09-14View Spectrum
    MS/MSLC-MS/MS Spectrum - , negativesplash10-004i-0900000000-c52421f0ba1f462418532017-09-14View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-IT , positivesplash10-00di-0900000000-0bd6ed3d764e5a9b374e2017-09-14View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-00e9-1900000000-9d0dde13bb1ce13e26442017-09-14View Spectrum
    MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-0w29-0940000000-127f99d8e7324e01eb662017-09-14View Spectrum
    MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-0ik9-0930000000-fe234438cbe3be0b30f62017-09-14View Spectrum
    MS/MSLC-MS/MS Spectrum - , positivesplash10-00di-1900000000-190ff3302e9f5a37a72f2017-09-14View Spectrum
    MS/MSLC-MS/MS Spectrum - , positivesplash10-001i-0900000000-d6040ea84fe19d8c5cc62017-09-14View Spectrum
    MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-001i-0900000000-935e5a47dc1abe7b11962021-09-20View Spectrum
    MS/MSLC-MS/MS Spectrum - 35V, Positivesplash10-00di-3900000000-2f3998477ce19f3ff96f2021-09-20View Spectrum
    MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-00di-4900000000-c89111b73e8a9a1631112021-09-20View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0900000000-5e7c398698bb5c16617d2017-09-01View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-1900000000-522eaddc21ef92e70e622017-09-01View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0005-9200000000-d10a1141c0e21f56ec002017-09-01View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-1900000000-bc2d3cb520a4fcb815292017-09-01View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-2900000000-e2e2992ce9b1265af7902017-09-01View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-05am-9300000000-e1aefedceb8692ffe91f2017-09-01View Spectrum
    NMR
    TypeDescriptionView
    1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)Spectrum
    1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
    1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
    1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
    1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
    1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
    1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
    1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
    1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
    1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
    1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
    1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
    1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
    1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
    1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
    1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
    1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
    1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
    1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
    1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
    1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
    2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Spectrum
    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