User Survey : Help improve ChEBI - please click here to take part in our quick User Survey.

CHEBI:5855 - ibuprofen

Main ChEBI Ontology Automatic Xrefs Reactions Pathways Models
ChEBI Name ibuprofen
ChEBI ID CHEBI:5855
Definition A monocarboxylic acid that is propionic acid in which one of the hydrogens at position 2 is substituted by a 4-(2-methylpropyl)phenyl group.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
Save molfile Download Molfile
Wikipedia License
Waiting for wikipedia content
Read full article at Wikipedia
Formula C13H18O2
Net Charge 0
Average Mass 206.28082
Monoisotopic Mass 206.131
InChI InChI=1S/C13H18O2/c1-9(2)8-11-4-6-12(7-5-11)10(3)13(14)15/h4-7,9-10H,8H2,1-3H3,(H,14,15)
InChIKey HEFNNWSXXWATRW-UHFFFAOYSA-N
SMILES CC(C)Cc1ccc(cc1)C(C)C(O)=O
Roles Classification
Chemical Role(s): radical scavenger
A role played by a substance that can react readily with, and thereby eliminate, radicals.
environmental contaminant
Any minor or unwanted substance introduced into the environment that can have undesired effects.
Bronsted acid
A molecular entity capable of donating a hydron to an acceptor (Bronsted base).
(via oxoacid )
Biological Role(s): cyclooxygenase 2 inhibitor
A cyclooxygenase inhibitor that interferes with the action of cyclooxygenase 2.
cyclooxygenase 1 inhibitor
A cyclooxygenase inhibitor that interferes with the action of cyclooxygenase 1.
xenobiotic
A xenobiotic (Greek, xenos "foreign"; bios "life") is a compound that is foreign to a living organism. Principal xenobiotics include: drugs, carcinogens and various compounds that have been introduced into the environment by artificial means.
non-narcotic analgesic
A drug that has principally analgesic, antipyretic and anti-inflammatory actions. Non-narcotic analgesics do not bind to opioid receptors.
Application(s): antipyretic
A drug that prevents or reduces fever by lowering the body temperature from a raised state. An antipyretic will not affect the normal body temperature if one does not have fever. Antipyretics cause the hypothalamus to override an interleukin-induced increase in temperature. The body will then work to lower the temperature and the result is a reduction in fever.
non-steroidal anti-inflammatory drug
An anti-inflammatory drug that is not a steroid. In addition to anti-inflammatory actions, non-steroidal anti-inflammatory drugs have analgesic, antipyretic, and platelet-inhibitory actions. They act by blocking the synthesis of prostaglandins by inhibiting cyclooxygenase, which converts arachidonic acid to cyclic endoperoxides, precursors of prostaglandins.
non-narcotic analgesic
A drug that has principally analgesic, antipyretic and anti-inflammatory actions. Non-narcotic analgesics do not bind to opioid receptors.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing ibuprofen (CHEBI:5855) has functional parent propionic acid (CHEBI:30768)
ibuprofen (CHEBI:5855) has role antipyretic (CHEBI:35493)
ibuprofen (CHEBI:5855) has role cyclooxygenase 1 inhibitor (CHEBI:50630)
ibuprofen (CHEBI:5855) has role cyclooxygenase 2 inhibitor (CHEBI:50629)
ibuprofen (CHEBI:5855) has role environmental contaminant (CHEBI:78298)
ibuprofen (CHEBI:5855) has role non-narcotic analgesic (CHEBI:35481)
ibuprofen (CHEBI:5855) has role non-steroidal anti-inflammatory drug (CHEBI:35475)
ibuprofen (CHEBI:5855) has role radical scavenger (CHEBI:48578)
ibuprofen (CHEBI:5855) has role xenobiotic (CHEBI:35703)
ibuprofen (CHEBI:5855) is a monocarboxylic acid (CHEBI:25384)
ibuprofen (CHEBI:5855) is conjugate acid of ibuprofen(1−) (CHEBI:132922)
Incoming carboxyibuprofen (CHEBI:133199) has functional parent ibuprofen (CHEBI:5855)
ibuproxam (CHEBI:76160) has functional parent ibuprofen (CHEBI:5855)
dexibuprofen (CHEBI:43415) is a ibuprofen (CHEBI:5855)
levibuprofen (CHEBI:47835) is a ibuprofen (CHEBI:5855)
ibuprofen(1−) (CHEBI:132922) is conjugate base of ibuprofen (CHEBI:5855)
IUPAC Name
2-[4-(2-methylpropyl)phenyl]propanoic acid
Synonyms Sources
(±)-2-(p-isobutylphenyl)propionic acid ChemIDplus
(±)-α-methyl-4-(2-methylpropyl)benzeneacetic acid ChemIDplus
(±)-ibuprofen ChemIDplus
(±)-p-isobutylhydratropic acid ChemIDplus
(4-isobutylphenyl)-α-methylacetic acid ChemIDplus
(RS)-ibuprofen ChemIDplus
2-(4-isobutylphenyl)propanoic acid NIST Chemistry WebBook
4-isobutylhydratropic acid ChemIDplus
α-(4-isobutylphenyl)propionic acid NIST Chemistry WebBook
α-(p-isobutylphenyl)propionic acid NIST Chemistry WebBook
Ibuprofen KEGG COMPOUND
Motrin ChemIDplus
Brand Names Sources
Adran DrugBank
Advil DrugBank
Amibufen DrugBank
Anco DrugBank
Anflagen DrugBank
Apsifen DrugBank
Bluton DrugBank
Brufen DrugBank
Brufort DrugBank
Buburone DrugBank
Butylenin DrugBank
Dolgin DrugBank
Dolgirid DrugBank
Dolgit DrugBank
Dolo-Dolgit DrugBank
Ebufac DrugBank
Epobron DrugBank
Femadon DrugBank
Haltran DrugBank
Ibu-Attritin DrugBank
Ibumetin DrugBank
Ibuprocin DrugBank
Ibutid DrugBank
Inabrin DrugBank
Inoven DrugBank
Lamidon DrugBank
Lebrufen DrugBank
Liptan DrugBank
Medipren DrugBank
Motrin DrugBank
Mynosedin DrugBank
Nobfen DrugBank
Nobgen DrugBank
Nuprin DrugBank
Nurofen DrugBank
Pediaprofen DrugBank
Roidenin DrugBank
Rufen DrugBank
Seclodin DrugBank
Suspren DrugBank
Tabalon DrugBank
Trendar DrugBank
Urem DrugBank
Database Links Databases
C01588 KEGG COMPOUND
D00126 KEGG DRUG
DB01050 DrugBank
GB971700 Patent
HMDB01925 HMDB
Ibuprofen Wikipedia
LSM-1354 LINCS
US3228831 Patent
US3385886 Patent
US5215755 Patent
US6727286 Patent
View more database links
Registry Numbers Types Sources
15687-27-1 CAS Registry Number KEGG COMPOUND
15687-27-1 CAS Registry Number ChemIDplus
15687-27-1 CAS Registry Number NIST Chemistry WebBook
2049713 Beilstein Registry Number ChemIDplus
2049713 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
11433218 PubMed citation Europe PMC
12723739 PubMed citation Europe PMC
14562167 PubMed citation Europe PMC
15506544 PubMed citation Europe PMC
16176022 PubMed citation Europe PMC
18335846 PubMed citation Europe PMC
18697608 PubMed citation Europe PMC
21368281 PubMed citation Europe PMC
24168233 PubMed citation Europe PMC
25708941 PubMed citation Europe PMC
25915907 PubMed citation Europe PMC
Last Modified
09 September 2016