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Record Information
Version1.0
Creation Date2016-09-30 22:48:07 UTC
Update Date2020-05-11 20:48:47 UTC
BMDB IDBMDB0001847
Secondary Accession Numbers
  • BMDB01847
Metabolite Identification
Common NameCaffeine
DescriptionCaffeine, also known as caffeine or caffeine, 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. Caffeine is a drug which is used for management of fatigue, orthostatic hypotension, and for the short term treatment of apnea of prematurity in infants. Caffeine exists as a solid, possibly soluble (in water), and an extremely weak basic (essentially neutral) compound (based on its pKa) molecule. Caffeine participates in a number of enzymatic reactions, within cattle. In particular, Caffeine can be converted into paraxanthine and formaldehyde through its interaction with the enzyme cytochrome P450 1A2. In addition, Caffeine can be converted into theobromine and formaldehyde; which is mediated by the enzymes cytochrome P450 1A2 and cytochrome P450 2E1. In cattle, caffeine is involved in the metabolic pathway called the caffeine metabolism pathway. Caffeine is a potentially toxic compound.
Structure
Thumb
Synonyms
ValueSource
1,3,7-Trimethyl-2,6-dioxopurineChEBI
1,3,7-Trimethylpurine-2,6-dioneChEBI
1,3,7-TrimethylxanthineChEBI
1-MethyltheobromineChEBI
3,7-Dihydro-1,3,7-trimethyl-1H-purin-2,6-dionChEBI
7-MethyltheophyllineChEBI
Anhydrous caffeineChEBI
CafeinaChEBI
CafeineChEBI
CoffeinChEBI
GuaranineChEBI
KoffeinChEBI
MateinaChEBI
MethyltheobromineChEBI
TeinaChEBI
TheinChEBI
TheineChEBI
RespiaKegg
1,3,7-Trimethyl-3,7-dihydro-1H-purine-2,6-dioneHMDB
1-Methyl-theobromineHMDB
3,7-Dihydro-1,3,7-trimethyl-1H-purine-2,6-dioneHMDB
7-Methyl theophyllineHMDB
Anhydrous caffeine (JP15)HMDB
HycomineHMDB
LanorinalHMDB
MethyltheobromideHMDB
Methylxanthine theophyllineHMDB
Monohydrate caffeineHMDB
PropoxypheneHMDB
Merck dura brand OF caffeineHMDB
Thompson brand 1 OF caffeineHMDB
Bristol-myers squibb brand OF caffeineHMDB
CaffedrineHMDB
DexitacHMDB
Percoffedrinol NHMDB
Pierre fabre brand OF caffeineHMDB
Republic drug brand OF caffeineHMDB
Thompson brand 2 OF caffeineHMDB
VivarinHMDB
Coffeinum NHMDB
Coffeinum purrumHMDB
DurvitanHMDB
GlaxoSmithKline brand OF caffeineHMDB
No dozHMDB
PercutaféineHMDB
Quick-pepHMDB
Seid brand OF caffeineHMDB
Berlin-chemie brand OF caffeineHMDB
Passauer brand OF caffeineHMDB
Quick pepHMDB
QuickPepHMDB
Chemical FormulaC8H10N4O2
Average Molecular Weight194.1906
Monoisotopic Molecular Weight194.080375584
IUPAC Name1,3,7-trimethyl-2,3,6,7-tetrahydro-1H-purine-2,6-dione
Traditional Namecaffeine
CAS Registry Number58-08-2
SMILES
CN1C=NC2=C1C(=O)N(C)C(=O)N2C
InChI Identifier
InChI=1S/C8H10N4O2/c1-10-4-9-6-5(10)7(13)12(3)8(14)11(6)2/h4H,1-3H3
InChI KeyRYYVLZVUVIJVGH-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
  • Purinone
  • 6-oxopurine
  • Alkaloid or derivatives
  • Pyrimidone
  • Pyrimidine
  • N-substituted imidazole
  • Heteroaromatic compound
  • Vinylogous amide
  • Imidazole
  • Azole
  • Urea
  • Lactam
  • Azacycle
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
  • Exogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cytoplasm
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point238 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility21.6 mg/mL at 25 °CNot Available
LogP-0.07HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
logP-0.24ALOGPS
logP-0.55ChemAxon
logS-1.2ALOGPS
pKa (Strongest Basic)-0.92ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area58.44 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity49.83 m³·mol⁻¹ChemAxon
Polarizability18.95 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (0 TMS)splash10-0536-3900000000-a9e112713ffae6dabdaaView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (0 TMS)splash10-0536-2900000000-8cdcd005b2e7622a02a3View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-052f-0900000000-f1084acfddb240696073View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-05nf-6900000000-8670a644cee5d9de78d4View in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0536-3900000000-4430852b279a72e34822View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-0900000000-51898e93480e848d7da1View in MoNA
GC-MSGC-MS Spectrum - CI-B (Non-derivatized)splash10-0002-0900000000-2aed5d425b6a95add5dbView in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a4l-4900000000-3ff72dace6687d242f1fView in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-1900000000-2ba1fae6e27c7b836984View in MoNA
GC-MSGC-MS Spectrum - CI-B (Non-derivatized)splash10-0002-0900000000-fd859aeb416e320d6379View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0536-3900000000-a9e112713ffae6dabdaaView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0536-2900000000-8cdcd005b2e7622a02a3View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-052f-0900000000-f1084acfddb240696073View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-05nf-6900000000-8670a644cee5d9de78d4View in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0536-3900000000-4430852b279a72e34822View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-052r-0900000000-41f36d541d34d2088964View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0006-0900000000-447fc72b2c709e2e18a9View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-000i-1900000000-5e3b29de16ad91c79fe0View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0006-9100000000-d6f6c52ac36c8f25a500View in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80) , Positivesplash10-0006-0900000000-cddd24399d942b1ac97cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - CI-B (Unknown) , Positivesplash10-0002-0900000000-2aed5d425b6a95add5dbView in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-60) , Positivesplash10-0a4l-4900000000-3ff72dace6687d242f1fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-68) , Positivesplash10-0006-1900000000-2ba1fae6e27c7b836984View in MoNA
LC-MS/MSLC-MS/MS Spectrum - CI-B (HITACHI M-60) , Positivesplash10-0002-0900000000-63b9ef42a3e8d59e9997View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-0002-0900000000-185b3d97d8857a0f269dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positivesplash10-0002-0900000000-f8a0c0dd9f5c4a272eafView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positivesplash10-000i-1900000000-dd8e35226d0704aa657dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positivesplash10-01x9-9800000000-70e3b0eb52481c39d191View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positivesplash10-001l-9100000000-6d428a5571beb0e3fed4View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-0002-0900000000-98bec16f898808c3de68View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Positivesplash10-0002-0900000000-b112e4e059e1ecf98c5fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - DI-ESI-qTof , Positivesplash10-00dr-0900000000-42c6f8fc7b924e9c64f3View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-000i-4900000000-a60a480f1340558740a2View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-000i-0900000000-695d910d49fc0beb1d54View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0002-0900000000-094879886a2e72bf0c56View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0900000000-761710441aa2c1c3ac68View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000b-0900000000-c10af6eda9a9a4094715View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01p9-3900000000-141118b1a93b4d48b2d4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0900000000-c8bd8cccb7dd6c66bb42View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-0900000000-2c8c1760161edd358026View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4r-5900000000-260de4a79007e853e4bbView in MoNA
MSMass Spectrum (Electron Ionization)splash10-052f-8900000000-68b5e9aa3404fb3d8d3aView in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,1H] 2D NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Epidermis
  • Kidney
  • Liver
  • Placenta
  • Prostate Tissue
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
EpidermisExpected but not QuantifiedNot ApplicableNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
KidneyExpected but not QuantifiedNot ApplicableNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
LiverExpected but not QuantifiedNot ApplicableNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
PlacentaExpected but not QuantifiedNot ApplicableNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
Prostate TissueExpected but not QuantifiedNot ApplicableNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
Abnormal Concentrations
Not Available
HMDB IDHMDB0001847
DrugBank IDDB00201
Phenol Explorer Compound IDNot Available
FooDB IDFDB002100
KNApSAcK IDC00001492
Chemspider ID2424
KEGG Compound IDC07481
BioCyc ID1-3-7-TRIMETHYLXANTHINE
BiGG IDNot Available
Wikipedia LinkCaffeine
METLIN ID1455
PubChem Compound2519
PDB IDNot Available
ChEBI ID27732
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available