CHEBI:133220 - tuberonic acid

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ChEBI Name tuberonic acid
ChEBI ID CHEBI:133220
Definition An oxo monocarboxylic acid that is (+)-7-isojasmonic acid in which one of the hydrogens of the side-chain methyl group is replaced by a hydroxy group.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula C12H18O4
Net Charge 0
Average Mass 226.269
Monoisotopic Mass 226.12051
InChI InChI=1S/C12H18O4/c13-7-3-1-2-4-10-9(8-12(15)16)5-6-11(10)14/h1-2,9-10,13H,3-8H2,(H,15,16)/b2-1-/t9-,10+/m1/s1
InChIKey RZGFUGXQKMEMOO-SZXTZRQCSA-N
SMILES C(=O)(O)C[C@@H]1[C@@H](C(CC1)=O)C/C=C\CCO
Metabolite of Species Details
Solanum lycopersicum (NCBI:txid4081) Found in fruit (BTO:0000486). See: MetaboLights Study
Solanum lycopersicum (NCBI:txid4081) Found in fruit (BTO:0000486). See: MetaboLights Study
Solanum lycopersicum (NCBI:txid4081) Found in fruit (BTO:0000486). See: MetaboLights Study
Solanum lycopersicum (NCBI:txid4081) Found in fruit (BTO:0000486). See: MetaboLights Study
Solanum lycopersicum (NCBI:txid4081) Found in fruit (BTO:0000486). See: MetaboLights Study
Solanum lycopersicum (NCBI:txid4081) Found in fruit (BTO:0000486). See: DOI
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): jasmonates
The jasmonates (JAs) are a group of plant hormones which help regulate plant growth and development.
plant metabolite
Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
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ChEBI Ontology
Outgoing tuberonic acid (CHEBI:133220) has functional parent (+)-7-isojasmonic acid (CHEBI:18435)
tuberonic acid (CHEBI:133220) has role jasmonates (CHEBI:24937)
tuberonic acid (CHEBI:133220) has role plant metabolite (CHEBI:76924)
tuberonic acid (CHEBI:133220) is a cyclopentanones (CHEBI:36140)
tuberonic acid (CHEBI:133220) is a homoallylic alcohol (CHEBI:134362)
tuberonic acid (CHEBI:133220) is a oxo monocarboxylic acid (CHEBI:35871)
tuberonic acid (CHEBI:133220) is a primary alcohol (CHEBI:15734)
tuberonic acid (CHEBI:133220) is conjugate acid of tuberonate (CHEBI:136182)
Incoming N-[(+)-12-hydroxy-7-isojasmonyl]isoleucine (CHEBI:137044) has functional parent tuberonic acid (CHEBI:133220)
methyl tuberonate (CHEBI:133219) has functional parent tuberonic acid (CHEBI:133220)
tuberonate (CHEBI:136182) is conjugate base of tuberonic acid (CHEBI:133220)
IUPAC Name
{(1R,2S)-2-[(2Z)-5-hydroxypent-2-en-1-yl]-3-oxocyclopentyl}acetic acid
Synonyms Sources
(+)-12-hydroxy-7-isojasmonic acid ChEBI
(1R,2S)-3-oxo-2-(5'-hydroxy-2'Z-pentenyl)-cyclopentaneacetic acid LIPID MAPS
12-hydroxy-epi-jasmonic acid ChEBI
Manual Xrefs Databases
4947920 ChemSpider
C00000221 KNApSAcK
LMFA02020007 LIPID MAPS
View more database links
Registry Numbers Types Sources
11073168 Reaxys Registry Number Reaxys
124649-26-9 CAS Registry Number ChemIDplus
Last Modified
22 August 2017