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CHEBI:133220 - tuberonic acid

ChEBI IDCHEBI:133220
ChEBI Nametuberonic acid
Stars
DefinitionAn 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.
Last Modified22 August 2017
Submittermwilliams
DownloadsMolfile
FormulaC12H18O4
Net Charge0
Average Mass226.272
Monoisotopic Mass226.12051
SMILESO=C(O)C[C@H]1CCC(=O)[C@H]1C/C=C\CCO
InChIInChI=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
InChIKeyRZGFUGXQKMEMOO-SZXTZRQCSA-N
Species of MetaboliteComponentSourceComments
Solanum lycopersicum (ncbitaxon:4081)
fruit (BTO:0000486) MetaboLights (MTBLS108)
fruit (BTO:0000486) MetaboLights (MTBLS111)
fruit (BTO:0000486) DOI (10.1007/s11306-014-0728-9)
fruit (BTO:0000486) MetaboLights (MTBLS107)
fruit (BTO:0000486) MetaboLights (MTBLS109)
fruit (BTO:0000486) MetaboLights (MTBLS110)
Roles Classification
Chemical Role:
Bronsted acid  A molecular entity capable of donating a hydron to an acceptor (Brønsted base).
Biological Roles:
plant metabolite  Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
jasmonates  The jasmonates (JAs) are a group of plant hormones which help regulate plant growth and development.
ChEBI Ontology
Outgoing Relation(s)
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 Relation(s)
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  Source
(1R,2S)-3-oxo-2-(5'-hydroxy-2'Z-pentenyl)-cyclopentaneacetic acidLIPID MAPS
12-hydroxy-epi-jasmonic acidChEBI
(+)-12-hydroxy-7-isojasmonic acidChEBI
Manual XrefsDatabases
4947920ChemSpider
LMFA02020007LIPID MAPS
C00000221KNApSAcK
Registry NumbersSources
Reaxys:11073168Reaxys
CAS:124649-26-9ChemIDplus