CHEBI:76204 - (2S)-2-(4-{[(1R,2S)-2-hydroxycyclopentyl]methyl}phenyl)propanoic acid

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ChEBI Name (2S)-2-(4-{[(1R,2S)-2-hydroxycyclopentyl]methyl}phenyl)propanoic acid
ChEBI ID CHEBI:76204
ChEBI ASCII Name (2S)-2-(4-{[(1R,2S)-2-hydroxycyclopentyl]methyl}phenyl)propanoic acid
Definition A monocarboxylic acid that is propionic acid in which one of the hydrogens at position 2 is substituted by a 4-[(2-hydroxycyclopentyl)methyl]phenyl group (the 2S,1'R,2'S-stereoisomer. The active metabolite of loxoprofen.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula C15H20O3
Net Charge 0
Average Mass 248.31750
Monoisotopic Mass 248.14124
InChI InChI=1S/C15H20O3/c1-10(15(17)18)12-7-5-11(6-8-12)9-13-3-2-4-14(13)16/h5-8,10,13-14,16H,2-4,9H2,1H3,(H,17,18)/t10-,13+,14-/m0/s1
InChIKey SHAHPWSYJFYMRX-GDLCADMTSA-N
SMILES C[C@H](C(O)=O)c1ccc(C[C@H]2CCC[C@@H]2O)cc1
Roles Classification
Chemical Role(s): Bronsted acid
A molecular entity capable of donating a hydron to an acceptor (Bronsted base).
(via oxoacid )
Biological Role(s): non-narcotic analgesic
A drug that has principally analgesic, antipyretic and anti-inflammatory actions. Non-narcotic analgesics do not bind to opioid receptors.
EC 1.14.99.1 (prostaglandin-endoperoxide synthase) inhibitor
A compound or agent that combines with cyclooxygenases (EC 1.14.99.1) and thereby prevents its substrate-enzyme combination with arachidonic acid and the formation of icosanoids, prostaglandins, and thromboxanes.
xenobiotic metabolite
Any metabolite produced by metabolism of a xenobiotic compound.
human metabolite
Any mammalian metabolite produced during a metabolic reaction in humans (Homo sapiens).
drug metabolite

Application(s): 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.
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.
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ChEBI Ontology
Outgoing (2S)-2-(4-{[(1R,2S)-2-hydroxycyclopentyl]methyl}phenyl)propanoic acid (CHEBI:76204) has functional parent loxoprofen (CHEBI:76172)
(2S)-2-(4-{[(1R,2S)-2-hydroxycyclopentyl]methyl}phenyl)propanoic acid (CHEBI:76204) has functional parent propionic acid (CHEBI:30768)
(2S)-2-(4-{[(1R,2S)-2-hydroxycyclopentyl]methyl}phenyl)propanoic acid (CHEBI:76204) has role antipyretic (CHEBI:35493)
(2S)-2-(4-{[(1R,2S)-2-hydroxycyclopentyl]methyl}phenyl)propanoic acid (CHEBI:76204) has role drug metabolite (CHEBI:49103)
(2S)-2-(4-{[(1R,2S)-2-hydroxycyclopentyl]methyl}phenyl)propanoic acid (CHEBI:76204) has role EC 1.14.99.1 (prostaglandin-endoperoxide synthase) inhibitor (CHEBI:35544)
(2S)-2-(4-{[(1R,2S)-2-hydroxycyclopentyl]methyl}phenyl)propanoic acid (CHEBI:76204) has role human metabolite (CHEBI:77746)
(2S)-2-(4-{[(1R,2S)-2-hydroxycyclopentyl]methyl}phenyl)propanoic acid (CHEBI:76204) has role non-narcotic analgesic (CHEBI:35481)
(2S)-2-(4-{[(1R,2S)-2-hydroxycyclopentyl]methyl}phenyl)propanoic acid (CHEBI:76204) has role non-steroidal anti-inflammatory drug (CHEBI:35475)
(2S)-2-(4-{[(1R,2S)-2-hydroxycyclopentyl]methyl}phenyl)propanoic acid (CHEBI:76204) has role xenobiotic metabolite (CHEBI:76206)
(2S)-2-(4-{[(1R,2S)-2-hydroxycyclopentyl]methyl}phenyl)propanoic acid (CHEBI:76204) is a cyclopentanols (CHEBI:23495)
(2S)-2-(4-{[(1R,2S)-2-hydroxycyclopentyl]methyl}phenyl)propanoic acid (CHEBI:76204) is a monocarboxylic acid (CHEBI:25384)
IUPAC Name
(2S)-2-(4-{[(1R,2S)-2-hydroxycyclopentyl]methyl}phenyl)propanoic acid
Synonyms Sources
loxoprofen active metabolite ChEBI
loxoprofen-SRS ChEBI
Registry Number Type Source
5745713 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
14980665 PubMed citation Europe PMC
15501405 PubMed citation Europe PMC
16272692 PubMed citation Europe PMC
16406342 PubMed citation Europe PMC
9650852 PubMed citation Europe PMC
9831331 PubMed citation Europe PMC
Last Modified
05 November 2013