Showing Compound Card for 1,3,7-Trimethyluric acid (CDB005293)

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Record Information
Version1.0
Created at2020-04-17 19:28:39 UTC
Updated at2020-12-07 19:11:54 UTC
CannabisDB IDCDB005293
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common Name1,3,7-Trimethyluric acid
Description1,3,7-Trimethyluric acid, also known as 8-oxy-caffeine or 1,3,7-trimethylate, 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. 1,3,7-Trimethyluric acid is an extremely weak basic (essentially neutral) compound (based on its pKa). 1,3,7-Trimethyluric acid exists in all living organisms, ranging from bacteria to humans. 1,3,7-trimethyluric acid can be biosynthesized from caffeine; which is catalyzed by the enzymes cytochrome P450 1A2, cytochrome P450 3A4, cytochrome P450 2C8, cytochrome P450 2C9, and cytochrome P450 2E1. In humans, 1,3,7-trimethyluric acid is involved in caffeine metabolism. Outside of the human body, 1,3,7-Trimethyluric acid has been detected, but not quantified in, several different foods, such as rubus (blackberry, raspberry), passion fruits, mountain yams, wasabis, and pigeon pea. This could make 1,3,7-trimethyluric acid a potential biomarker for the consumption of these foods. An oxopurine in which the purine ring is substituted by oxo groups at positions 2, 6, and 8, and the nitrogens at positions 1, 3, and 7 are substituted by methyl groups. 1,3,7-Trimethyluric acid is expected to be in Cannabis as all living plants are known to produce and metabolize it.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
1,3,7-Trimethyl-2,3,6,7,8,9-hexahydro-1H-purine-2,6,8-trioneChEBI
1,3,7-TrimethylurateChEBI
7,9-Dihydro-1,3,7-trimethyl-1H-purine-2,6,8(3H)-trioneChEBI
8-OxocaffeineChEBI
8-Oxy-caffeineChEBI
1,3,7-TrimethylateGenerator
1,3,7-Trimethylic acidGenerator
1,3, 7-Trimethyluric acidHMDB
1,3,7-Trimethyl-7,9-dihydro-1H-purine-2,6,8(3H)-trioneHMDB
2,6,8-Trihydroxy-1,3,7-trimethylpurineHMDB
8-Hydroxy-1,3,7-trimethyl-3,7-dihydro-1H-purine-2,6-dioneHMDB
Trimethyl uric acidHMDB
Chemical FormulaC8H10N4O3
Average Molecular Weight210.19
Monoisotopic Molecular Weight210.0753
IUPAC Name1,3,7-trimethyl-2,3,6,7,8,9-hexahydro-1H-purine-2,6,8-trione
Traditional Name1,3,7-trimethyluric acid
CAS Registry Number5415-44-1
SMILES
CN1C(=O)NC2=C1C(=O)N(C)C(=O)N2C
InChI Identifier
InChI=1S/C8H10N4O3/c1-10-4-5(9-7(10)14)11(2)8(15)12(3)6(4)13/h1-3H3,(H,9,14)
InChI KeyBYXCFUMGEBZDDI-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
  • Azole
  • Imidazole
  • Heteroaromatic compound
  • Vinylogous amide
  • Lactam
  • Urea
  • Azacycle
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Role

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility5.5 mg/mL at 15 °CNot Available
logP-0.37GASPARI,F & BONATI,M (1987)
Predicted Properties
PropertyValueSource
logP-0.49ALOGPS
logP-0.87ChemAxon
logS-0.87ALOGPS
pKa (Strongest Acidic)8.46ChemAxon
pKa (Strongest Basic)-5.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area72.96 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity60.32 m³·mol⁻¹ChemAxon
Polarizability19.82 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MS1,3,7-Trimethyluric acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0udi-1900000000-7ceff209b1b0d4f92cf0Spectrum
Predicted GC-MS1,3,7-Trimethyluric acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, N/A (Annotated)splash10-03di-0090000000-c6489ab09ec74614db4c2012-07-25View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, N/A (Annotated)splash10-001a-6900000000-ac2e74a460c865c0636b2012-07-25View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, N/A (Annotated)splash10-067l-9100000000-cbac42dd288a8ef44fd82012-07-25View Spectrum
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-0006-0900000000-a9bff7d94cd5ffe280b92017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-0udj-0900000000-5316637dfdcce19f087a2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-0imj-3930000000-0593f0aaec496efc76962021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-000f-9500000000-fb28fd8903d55811b0a12021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-000f-0910000000-eca560d36d14fb72dfe92021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0190000000-6d4b9f5e8e42f3040e5e2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-000l-7900000000-2ba0d4f876fceab5182f2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-000f-9700000000-a42f3584a2bad7add22d2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-052o-1920000000-53b778bbd3181f2ed83a2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 30V, Negativesplash10-000l-3900000000-4305cd286c077e5210792021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0690000000-62dc7eb029289b61c3b12021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-000f-0900000000-3eb9fdcfd2e67d0f4e2c2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-0006-9100000000-f438ad2b70b2e97356432021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-03di-0190000000-42add8be62bbafed200c2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-03dj-2930000000-2855ca36942d5e8f069e2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-066u-9200000000-708fd95bbe618c2ace7d2021-09-20View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0090000000-153ea9ea8b4fe3692bfb2015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ik9-1790000000-2d17afbf34659471f5242015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0m2a-4900000000-c783d40d7ed0c6ae44a92015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0190000000-9858aab04a40f6286f932015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-1790000000-2089332ab35983ee2c772015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-066u-8900000000-53f14da0e8f43679f03f2015-05-27View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 600 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
EnzymesNot Available
TransportersNot Available
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0002123
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB022854
KNApSAcK IDC00051957
Chemspider ID71754
KEGG Compound IDC16361
BioCyc IDCPD-12480
BiGG IDNot Available
Wikipedia Link1,3,7-Trimethyluric_acid
METLIN IDNot Available
PubChem Compound79437
PDB IDNot Available
ChEBI ID691622
References
General ReferencesNot Available