Showing Compound Card for Paraxanthine (CDB005291)

Jump To Section:
IdentificationTaxonomyOntologyPhysical propertiesSpectraProtein targetPathwaysConcentrationsLinksReferencesenzymes (4) Show 28 proteinsXML
Record Information
Version1.0
Created at2020-04-17 19:28:27 UTC
Updated at2020-12-07 19:11:54 UTC
CannabisDB IDCDB005291
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common 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. Paraxanthine is expected to be in Cannabis as all living plants are known to produce and metabolize it.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
3,7-Dihydro-1,7-dimethyl-1H-purine-2,6-dioneChEBI
p-XanthineChEBI
1,7-Dimethyl-xanthineHMDB
1,7-DimethylxanthineHMDB, MeSH
Chemical FormulaC7H8N4O2
Average Molecular Weight180.16
Monoisotopic Molecular Weight180.0647
IUPAC Name1,7-dimethyl-2,3,6,7-tetrahydro-1H-purine-2,6-dione
Traditional Nameparaxanthine
CAS Registry Number611-59-6
SMILES
CN1C=NC2=C1C(=O)N(C)C(=O)N2
InChI Identifier
InChI=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
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
  • 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:

Role

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point351 - 352 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
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
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
Pathways
Pathways
Protein Targets
Enzymes
Protein NameGene NameLocusUniprot IDDetails
Arylamine N-acetyltransferase 1NAT18p22P18440 details
Arylamine N-acetyltransferase 2NAT28p22P11245 details
Xanthine dehydrogenase/oxidaseXDH2p23.1P47989 details
Cytochrome P450, family 1, subfamily A, polypeptide 1CYP1A115q24.1A0N0X8 details
TransportersNot Available
Metal Bindings
Protein NameGene NameLocusUniprot IDDetails
Xanthine dehydrogenase/oxidaseXDH2p23.1P47989 details
Cytochrome P450 3A4CYP3A47q21.1P08684 details
Cytochrome P450 2C9CYP2C910q24P11712 details
Cytochrome P450 2C19CYP2C1910q24P33261 details
Cytochrome P450 2E1CYP2E110q24.3-qterP05181 details
Cytochrome P450 3A43CYP3A437q21.1Q9HB55 details
Cytochrome P450 1B1CYP1B12p22.2Q16678 details
Cytochrome P450 2C18CYP2C1810q24P33260 details
Cytochrome P450 2F1CYP2F119q13.2P24903 details
Cytochrome P450 4X1CYP4X11Q8N118 details
Cytochrome P450 2B6CYP2B619q13.2P20813 details
Cytochrome P450 3A5CYP3A57q21.1P20815 details
Cytochrome P450 2A13CYP2A1319q13.2Q16696 details
Cytochrome P450 3A7CYP3A77q21-q22.1P24462 details
Cytochrome P450 4B1CYP4B11p34-p12P13584 details
Cytochrome P450 4Z1CYP4Z11p33Q86W10 details
Cytochrome P450 1A2CYP1A215q24.1P05177 details
Cytochrome P450 19A1CYP19A115q21.1P11511 details
Cytochrome P450 2C8CYP2C810q23.33P10632 details
Cytochrome P450 2S1CYP2S119q13.1Q96SQ9 details
Cytochrome P450 2J2CYP2J21p31.3-p31.2P51589 details
Cytochrome P450 2A7CYP2A719q13.2P20853 details
Cytochrome P450 2A6CYP2A619q13.2P11509 details
Cytochrome P450, family 1, subfamily A, polypeptide 1CYP1A115q24.1A0N0X8 details
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0001860
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB022714
KNApSAcK IDC00039930
Chemspider ID4525
KEGG Compound IDC13747
BioCyc ID1-7-DIMETHYLXANTHINE
BiGG IDNot Available
Wikipedia LinkParaxanthine
METLIN ID1457
PubChem Compound4687
PDB IDNot Available
ChEBI ID25858
References
General ReferencesNot Available

Only showing the first 10 proteins. There are 28 proteins in total.

Show All

Enzymes

Enzyme Details
1. Arylamine N-acetyltransferase 1
General function:
Involved in acetyltransferase activity
Specific function:
Participates in the detoxification of a plethora of hydrazine and arylamine drugs. Catalyzes the N- or O-acetylation of various arylamine and heterocyclic amine substrates and is able to bioactivate several known carcinogens.
Gene Name:
NAT1
Uniprot ID:
P18440
Molecular weight:
33898.445
Enzyme Details
2. Arylamine N-acetyltransferase 2
General function:
Involved in acetyltransferase activity
Specific function:
Participates in the detoxification of a plethora of hydrazine and arylamine drugs. Catalyzes the N- or O-acetylation of various arylamine and heterocyclic amine substrates and is able to bioactivate several known carcinogens.
Gene Name:
NAT2
Uniprot ID:
P11245
Molecular weight:
33570.245
Enzyme Details
3. Xanthine dehydrogenase/oxidase
General function:
Involved in oxidoreductase activity
Specific function:
Key enzyme in purine degradation. Catalyzes the oxidation of hypoxanthine to xanthine. Catalyzes the oxidation of xanthine to uric acid. Contributes to the generation of reactive oxygen species. Has also low oxidase activity towards aldehydes (in vitro).
Gene Name:
XDH
Uniprot ID:
P47989
Molecular weight:
146422.99
Enzyme Details
4. Cytochrome P450, family 1, subfamily A, polypeptide 1
General function:
Involved in monooxygenase activity
Specific function:
Not Available
Gene Name:
CYP1A1
Uniprot ID:
A0N0X8
Molecular weight:
58164.8

Only showing the first 10 proteins. There are 28 proteins in total.

Show All