Livestock Metabolome Database: Showing metabocard for Caffeine (LMDB00354)

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-07-13 19:47:59 UTC

Update Date

2016-09-23 18:45:43 UTC

Lmdb

LMDB00354

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Caffeine

Description

Caffeine is a member of the methylxanthine family of drugs. A number of in vitro and in vivo studies have demonstrated that caffeine modulates both innate and adaptive immune responses. For instance studies indicate that caffeine and its major metabolite paraxanthine suppress neutrophil and monocyte chemotaxis, and also suppress production of the pro-inflammatory cytokine tumor necrosis factor (TNF) alpha. Caffeine has also been reported to suppress lymphocyte function as indicated by reduced T-cell proliferation and impaired production of Th1 (interleukin [IL]-2 and interferon [IFN]-gamma), Th2 (IL-4, IL-5) and Th3 (IL-10) cytokines. Studies also indicate that caffeine suppresses antibody production. The evidence suggests that at least some of the immunomodulatory actions of caffeine are mediated via inhibition of cyclic adenosine monophosphate (cAMP)-phosphodiesterase (PDE), and consequential increase in intracellular cAMP concentrations. Overall, these studies indicate that caffeine, like other members of the methylxanthine family, is largely anti-inflammatory in nature (PMID 16540173 ). Whether caffeine consumption contribute to the development of cardiovascular disease (CVD) is unclear. The literature indicates a strong relationship between caffeine consumption and elevated cholesterol levels. Available studies are limited by small samples sizes (PMID: 16856769 ). There is extensive evidence that caffeine at dietary doses increases blood pressure (BP). When considered comprehensively, findings from experimental and epidemiologic studies converge to show that BP remains reactive to the pressor effects of caffeine in the diet (PMID: 14747639 ). Caffeine is a purine alkaloid. At intake levels, caffeine appears to exert most of its biological effects through the antagonism of the A1 and A2A subtypes of the adenosine receptor. Adenosine is an endogenous neuromodulator with mostly inhibitory effects, and adenosine antagonism by caffeine results in effects that are generally stimulatory. Some physiological effects associated with caffeine administration include central nervous system stimulation, acute elevation of blood pressure, increased metabolic rate, and diuresis. Caffeine is rapidly and almost completely absorbed in the digestive system and distributed to all tissues, including the brain. Caffeine metabolism occurs primarily in the liver, where the activity of the cytochrome P450 isoform CYP1A2 accounts for almost 95% of the primary metabolism of caffeine. CYP1A2-catalyzed 3-demethylation of caffeine results in the formation of 1,7-dimethylxanthine (paraxanthine). Paraxanthine may be demethylated by CYP1A2 to form 1-methylxanthine, which may be oxidized to 1-methyluric acid by xanthine oxidase. Paraxanthine may also be hydroxylated by CYP2A6 to form 1,7-dimethyluric acid, or acetylated by N-acetyltransferase 2 (NAT2) to form 5-acetylamino-6-formylamino-3-methyluracil, an unstable compound that may be deformylated nonenzymatically to form 5-acetylamino-6-amino-3-methyluracil (PMID 16507475 ).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
1,3,7-Trimethyl-2,6-dioxopurine	ChEBI
1,3,7-Trimethylpurine-2,6-dione	ChEBI
1,3,7-Trimethylxanthine	ChEBI
1-Methyltheobromine	ChEBI
3,7-Dihydro-1,3,7-trimethyl-1H-purin-2,6-dion	ChEBI
7-Methyltheophylline	ChEBI
Anhydrous caffeine	ChEBI
Cafeina	ChEBI
Cafeine	ChEBI
Coffein	ChEBI
Guaranine	ChEBI
Koffein	ChEBI
Mateina	ChEBI
Methyltheobromine	ChEBI
Teina	ChEBI
Thein	ChEBI
Theine	ChEBI
Respia	Kegg
1,3,7-Trimethyl-3,7-dihydro-1H-purine-2,6-dione	HMDB
1-Methyl-theobromine	HMDB
3,7-Dihydro-1,3,7-trimethyl-1H-purine-2,6-dione	HMDB
7-Methyl theophylline	HMDB
Anhydrous caffeine (JP15)	HMDB
Hycomine	HMDB
Lanorinal	HMDB
Methyltheobromide	HMDB
Methylxanthine theophylline	HMDB
Monohydrate caffeine	HMDB
Propoxyphene	HMDB
Merck dura brand OF caffeine	HMDB
Thompson brand 1 OF caffeine	HMDB
Bristol-myers squibb brand OF caffeine	HMDB
Caffedrine	HMDB
Dexitac	HMDB
Percoffedrinol N	HMDB
Pierre fabre brand OF caffeine	HMDB
Republic drug brand OF caffeine	HMDB
Thompson brand 2 OF caffeine	HMDB
Vivarin	HMDB
Coffeinum N	HMDB
Coffeinum purrum	HMDB
Durvitan	HMDB
GlaxoSmithKline brand OF caffeine	HMDB
No doz	HMDB
Percutaféine	HMDB
Quick-pep	HMDB
Seid brand OF caffeine	HMDB
Berlin-chemie brand OF caffeine	HMDB
Passauer brand OF caffeine	HMDB
Quick pep	HMDB
QuickPep	HMDB

Chemical Formula

C₈H₁₀N₄O₂

Average Molecular Weight

194.1906

Monoisotopic Molecular Weight

194.080375584

IUPAC Name

1,3,7-trimethyl-2,3,6,7-tetrahydro-1H-purine-2,6-dione

Traditional Name

caffeine

CAS Registry Number

58-08-2

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 Key

RYYVLZVUVIJVGH-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.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Imidazopyrimidines

Sub Class

Purines and purine derivatives

Direct Parent

Xanthines

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 Framework

Aromatic heteropolycyclic compounds

External Descriptors

purine alkaloid (CHEBI:27732 )
trimethylxanthine (CHEBI:27732 )
Purine alkaloids (C07481 )
a small molecule (1-3-7-TRIMETHYLXANTHINE )

Ontology

Status

Detected and Quantified

Origin

Not Available

Biofunction

Not Available

Application

Not Available

Cellular locations

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	-0.24	ALOGPS
logP	-0.55	ChemAxon
logS	-1.2	ALOGPS
pKa (Strongest Basic)	-0.92	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	58.44 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	49.83 m³·mol⁻¹	ChemAxon
Polarizability	18.95 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (0 TMS)	splash10-0536-3900000000-a9e112713ffae6dabdaa	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (0 TMS)	splash10-0536-2900000000-8cdcd005b2e7622a02a3	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)	splash10-052f-0900000000-f1084acfddb240696073	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)	splash10-05nf-6900000000-8670a644cee5d9de78d4	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-0536-3900000000-4430852b279a72e34822	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0006-0900000000-51898e93480e848d7da1	Spectrum
GC-MS	GC-MS Spectrum - CI-B (Non-derivatized)	splash10-0002-0900000000-2aed5d425b6a95add5db	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0a4l-4900000000-3ff72dace6687d242f1f	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0006-1900000000-2ba1fae6e27c7b836984	Spectrum
GC-MS	GC-MS Spectrum - CI-B (Non-derivatized)	splash10-0002-0900000000-fd859aeb416e320d6379	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0536-3900000000-a9e112713ffae6dabdaa	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0536-2900000000-8cdcd005b2e7622a02a3	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-052f-0900000000-f1084acfddb240696073	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-05nf-6900000000-8670a644cee5d9de78d4	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-0536-3900000000-4430852b279a72e34822	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-052r-0900000000-41f36d541d34d2088964	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-0006-0900000000-447fc72b2c709e2e18a9	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-000i-1900000000-5e3b29de16ad91c79fe0	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-0006-9100000000-d6f6c52ac36c8f25a500	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI M-80) , Positive	splash10-0006-0900000000-cddd24399d942b1ac97c	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - CI-B (Unknown) , Positive	splash10-0002-0900000000-2aed5d425b6a95add5db	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI M-60) , Positive	splash10-0a4l-4900000000-3ff72dace6687d242f1f	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI M-68) , Positive	splash10-0006-1900000000-2ba1fae6e27c7b836984	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - CI-B (HITACHI M-60) , Positive	splash10-0002-0900000000-63b9ef42a3e8d59e9997	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive	splash10-0002-0900000000-185b3d97d8857a0f269d	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive	splash10-0002-0900000000-f8a0c0dd9f5c4a272eaf	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive	splash10-000i-1900000000-dd8e35226d0704aa657d	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive	splash10-01x9-9800000000-70e3b0eb52481c39d191	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positive	splash10-001l-9100000000-6d428a5571beb0e3fed4	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive	splash10-0002-0900000000-98bec16f898808c3de68	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Positive	splash10-0002-0900000000-b112e4e059e1ecf98c5f	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - DI-ESI-qTof , Positive	splash10-00dr-0900000000-42c6f8fc7b924e9c64f3	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-qTof , Positive	splash10-000i-4900000000-a60a480f1340558740a2	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-000i-0900000000-695d910d49fc0beb1d54	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-0002-0900000000-094879886a2e72bf0c56	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-0002-0900000000-fa38c865089a3a05f287	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-000b-0900000000-0e82732a924c974dd0c8	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-000i-0900000000-bfc94c8091471847482b	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-000i-1900000000-c8fcf16986c494898203	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-000i-3900000000-9569e0552abb7ebd145a	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-0002-0900000000-3a924abd44877050c1c9	Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-052f-8900000000-68b5e9aa3404fb3d8d3a	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
2D NMR	[1H,1H] 2D NMR Spectrum	Not Available	Spectrum
2D NMR	[1H,13C] 2D NMR Spectrum	Not Available	Spectrum

Biological Properties

Cellular Locations

Not Available

Biofluid Locations and Tissue Locations

Ruminal Fluid

Concentrations

Biofluid	Status	Value	Condition	Species	Reference	Details
Ruminal Fluid	Detected and Quantified	16 +/- 4 uM	Not Available	Bovine	Saleem F, Bouatra...	details
Ruminal Fluid	Detected and Quantified	17 +/- 7 uM	Not Available	Bovine	Saleem F, Bouatra...	details
Ruminal Fluid	Detected and Quantified	23 +/- 8 uM	Not Available	Bovine	Saleem F, Bouatra...	details
Ruminal Fluid	Detected and Quantified	23 +/- 8 uM	Not Available	Bovine	Saleem F, Bouatra...	details
Ruminal Fluid	Detected and Quantified	26 +/- 6 uM	Not Available	Bovine	Saleem F, Bouatra...	details
Ruminal Fluid	Detected and Quantified	65 +/- 12 uM	Not Available	Bovine	Saleem F, Bouatra...	details
Ruminal Fluid	Detected and Quantified	16.2 uM	Not Available	Bovine	22959937	details
Ruminal Fluid	Detected and Quantified	16.6 uM	Not Available	Bovine	22959937	details
Ruminal Fluid	Detected and Quantified	10.8 uM	Not Available	Bovine	Burim NA, Qendrim...	details
Ruminal Fluid	Detected and Quantified	22.8 uM	Not Available	Bovine	22959937	details
Ruminal Fluid	Detected and Quantified	13.7 uM	Not Available	Bovine	Burim NA, Qendrim...	details
Ruminal Fluid	Detected and Quantified	25.5 uM	Not Available	Bovine	22959937	details
Ruminal Fluid	Detected and Quantified	15.3 uM	Not Available	Bovine	Burim NA, Qendrim...	details
Ruminal Fluid	Detected and Quantified	15.7 uM	Not Available	Bovine	Burim NA, Qendrim...	details

External Links

DrugBank ID

DB00201

HMDB ID

HMDB0001847

FooDB ID

FDB002100

Phenol Explorer ID

Not Available

KNApSAcK ID

C00001492

BiGG ID

Not Available

BioCyc ID

1-3-7-TRIMETHYLXANTHINE

METLIN ID

1455

PDB ID

Not Available

Wikipedia Link

Chemspider ID

ChEBI ID

PubChem Compound ID

Kegg Compound ID

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Rodrigues IM, Klein LC: Boiled or filtered coffee? Effects of coffee and caffeine on cholesterol, fibrinogen and C-reactive protein. Toxicol Rev. 2006;25(1):55-69. [16856769 ]
Lamarine RJ: Selected health and behavioral effects related to the use of caffeine. J Community Health. 1994 Dec;19(6):449-66. [7844249 ]
James JE: Critical review of dietary caffeine and blood pressure: a relationship that should be taken more seriously. Psychosom Med. 2004 Jan-Feb;66(1):63-71. [14747639 ]
Higdon JV, Frei B: Coffee and health: a review of recent human research. Crit Rev Food Sci Nutr. 2006;46(2):101-23. [16507475 ]
Horrigan LA, Kelly JP, Connor TJ: Immunomodulatory effects of caffeine: friend or foe? Pharmacol Ther. 2006 Sep;111(3):877-92. Epub 2006 Mar 15. [16540173 ]

Showing metabocard for Caffeine (LMDB00354)

Structure for LMDB00354 (Caffeine)