ChEBI logo

ChEBI


    The database and ontology of Chemical Entities of Biological Interest

spacer

caffeine (CHEBI:27732)

Search for only All in ChEBI

Main     ChEBI Ontology     Automatic Xrefs      
ChEBI Name caffeine
ChEBI ID CHEBI:27732
Definition A trimethylxanthine in which the three methyl groups are located at positions 1, 3, and 7.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:41472, CHEBI:22982, CHEBI:3295
Supplier Information
See structure as:  Image  Applet
Save molfile Download Molfile
more structures >>
Wikipedia License
Waiting for wikipedia content
Read full article at Wikipedia
Formula Source
C8H10N4O2 KEGG COMPOUND
Net Charge 0
Average Mass 194.19076
InChI
InChI=1S/C8H10N4O2/c1-10-4-9-6-5(10)7(13)12(3)8(14)11(6)2/h4H,1-3H3
InChIKey
RYYVLZVUVIJVGH-UHFFFAOYSA-N
SMILES
Cn1cnc2n(C)c(=O)n(C)c(=O)c12
Roles Classification
Chemical Role(s): EC 3.1.4.* (phosphoric diester hydrolase) inhibitor
An EC 3.1.* (ester hydrolase) inhibitor that interferes with the action of a phosphoric diester hydrolase (EC 3.1.4.*).
EC 2.7.11.1 (non-specific serine/threonine protein kinase) inhibitor
An EC 2.7.11.* (protein-serine/threonine kinase) inhibitor that interferes with the action of non-specific serine/threonine protein kinase (EC 2.7.11.1), a kinase enzyme involved in phosphorylation of hydroxy group of serine or threonine.
Biological Role(s): EC 3.1.4.* (phosphoric diester hydrolase) inhibitor
An EC 3.1.* (ester hydrolase) inhibitor that interferes with the action of a phosphoric diester hydrolase (EC 3.1.4.*).
EC 2.7.11.1 (non-specific serine/threonine protein kinase) inhibitor
An EC 2.7.11.* (protein-serine/threonine kinase) inhibitor that interferes with the action of non-specific serine/threonine protein kinase (EC 2.7.11.1), a kinase enzyme involved in phosphorylation of hydroxy group of serine or threonine.
ryanodine receptor agonist
A ryanodine receptor modulator which activates the receptor. Ryanodine receptors (RyRs) act as selective ion channels, modulating the release of calcium. Activating the receptors causes the release of calcium, so depleting internal calcium and ultimately preventing further muscle contraction.
fungal secondary metabolite
Any fungal metabolite that is not directly involved in the normal growth, development or reproduction of fungi.
adenosine A2A receptor antagonist
An antagonist at the A2A receptor.
adenosine receptor antagonist
An antagonist at any adenosine receptor.
ryanodine receptor modulator

mutagen
An agent that increases the frequency of mutations above the normal background level, usually by interacting directly with DNA and causing it damage, including base substitution.
secondary metabolite
A metabolite that is not directly involved in the normal growth, development or reproduction of an organism.
(via alkaloid )
Application(s): psychotropic drug
A loosely defined grouping of drugs that have effects on psychological function.
diuretic
An agent that promotes the excretion of urine through its effects on kidney function.
food additive
Any substance which is added to food to preserve or enhance its flavour and/or appearance.
adjuvant
Any pharmacological or immunological agent that modifies the effect of other agents such as drugs or vaccines while having few if any direct effects when given by itself.
central nervous system stimulant
Any drug that enhances the activity of the central nervous system.
View more on the ChEBI Ontology
ChEBI Ontology
Outgoing caffeine (CHEBI:27732) has role adenosine A2A receptor antagonist (CHEBI:53121)
caffeine (CHEBI:27732) has role adenosine receptor antagonist (CHEBI:71232)
caffeine (CHEBI:27732) has role adjuvant (CHEBI:60809)
caffeine (CHEBI:27732) has role central nervous system stimulant (CHEBI:35337)
caffeine (CHEBI:27732) has role diuretic (CHEBI:35498)
caffeine (CHEBI:27732) has role EC 2.7.11.1 (non-specific serine/threonine protein kinase) inhibitor (CHEBI:50925)
caffeine (CHEBI:27732) has role EC 3.1.4.* (phosphoric diester hydrolase) inhibitor (CHEBI:50218)
caffeine (CHEBI:27732) has role food additive (CHEBI:64047)
caffeine (CHEBI:27732) has role fungal secondary metabolite (CHEBI:75765)
caffeine (CHEBI:27732) has role mutagen (CHEBI:25435)
caffeine (CHEBI:27732) has role psychotropic drug (CHEBI:35471)
caffeine (CHEBI:27732) has role ryanodine receptor agonist (CHEBI:67114)
caffeine (CHEBI:27732) has role ryanodine receptor modulator (CHEBI:38809)
caffeine (CHEBI:27732) is a alkaloid (CHEBI:22315)
caffeine (CHEBI:27732) is a purine alkaloid (CHEBI:26385)
caffeine (CHEBI:27732) is a trimethylxanthine (CHEBI:27134)
Incoming 8-(3-chlorostyryl)caffeine (CHEBI:53115) has functional parent caffeine (CHEBI:27732)
caffeine monohydrate (CHEBI:31332) has part caffeine (CHEBI:27732)
IUPAC Name
1,3,7-trimethyl-3,7-dihydro-1H-purine-2,6-dione
Synonyms Sources
1,3,7-trimethyl-2,6-dioxopurine ChemIDplus
1,3,7-trimethylpurine-2,6-dione IUPHAR
1,3,7-trimethylxanthine NIST Chemistry WebBook
1-methyltheobromine ChemIDplus
3,7-Dihydro-1,3,7-trimethyl-1H-purin-2,6-dion NIST Chemistry WebBook
7-methyltheophylline NIST Chemistry WebBook
anhydrous caffeine KEGG DRUG
cafeína ChemIDplus
caféine ChEBI
Caffeine KEGG COMPOUND
CAFFEINE PDBeChem
Coffein ChemIDplus
guaranine IUPHAR
Koffein ChemIDplus
mateína ChemIDplus
methyltheobromine IUPHAR
teína ChEBI
Thein ChemIDplus
theine NIST Chemistry WebBook
Database Links Databases
1-3-7-TRIMETHYLXANTHINE MetaCyc
C07481 KEGG COMPOUND
Caffeine Wikipedia
CFF PDBeChem
D00528 KEGG DRUG
DB00201 DrugBank
HMDB01847 HMDB
View more database links
Registry Numbers Types Sources
103040 Gmelin Registry Number Gmelin
17705 Beilstein Registry Number Beilstein
17705 Reaxys Registry Number Reaxys
58-08-2 CAS Registry Number KEGG COMPOUND
58-08-2 CAS Registry Number NIST Chemistry WebBook
58-08-2 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
10510174 PubMed citation CiteXplore
10796597 PubMed citation CiteXplore
10803761 PubMed citation CiteXplore
10822912 PubMed citation CiteXplore
10884512 PubMed citation CiteXplore
10924888 PubMed citation CiteXplore
10983026 PubMed citation CiteXplore
11014293 PubMed citation CiteXplore
11022879 PubMed citation CiteXplore
11209966 PubMed citation CiteXplore
11312039 PubMed citation CiteXplore
11410911 PubMed citation CiteXplore
11431501 PubMed citation CiteXplore
11815511 PubMed citation CiteXplore
11949272 PubMed citation CiteXplore
12397877 PubMed citation CiteXplore
12457274 PubMed citation CiteXplore
12574990 PubMed citation CiteXplore
12915014 PubMed citation CiteXplore
12943586 PubMed citation CiteXplore
14521986 PubMed citation CiteXplore
14607010 PubMed citation CiteXplore
15257305 PubMed citation CiteXplore
15280431 PubMed citation CiteXplore
15681408 PubMed citation CiteXplore
15718055 PubMed citation CiteXplore
15840517 PubMed citation CiteXplore
16143823 PubMed citation CiteXplore
16391865 PubMed citation CiteXplore
16528931 PubMed citation CiteXplore
16644114 PubMed citation CiteXplore
16709440 PubMed citation CiteXplore
16805851 PubMed citation CiteXplore
16856769 PubMed citation CiteXplore
17132260 PubMed citation CiteXplore
17387608 PubMed citation CiteXplore
17508167 PubMed citation CiteXplore
17724925 PubMed citation CiteXplore
17932622 PubMed citation CiteXplore
18258404 PubMed citation CiteXplore
18421070 PubMed citation CiteXplore
18625110 PubMed citation CiteXplore
18647558 PubMed citation CiteXplore
19007524 PubMed citation CiteXplore
19047957 PubMed citation CiteXplore
19084078 PubMed citation CiteXplore
19088793 PubMed citation CiteXplore
19418355 PubMed citation CiteXplore
19879252 PubMed citation CiteXplore
20164568 PubMed citation CiteXplore
20470411 PubMed citation CiteXplore
22770225 PubMed citation CiteXplore
7441110 PubMed citation CiteXplore
7689104 PubMed citation CiteXplore
8332255 PubMed citation CiteXplore
8347173 PubMed citation CiteXplore
8679661 PubMed citation CiteXplore
9063686 PubMed citation CiteXplore
9067318 PubMed citation CiteXplore
9132918 PubMed citation CiteXplore
9218278 PubMed citation CiteXplore
Last Modified
13 January 2014

spacer
spacer