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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2021-09-24 04:20:45 UTC
Update Date2021-09-24 04:20:45 UTC
HMDB IDHMDB0303749
Secondary Accession NumbersNone
Metabolite Identification
Common Name7-Epi-12-hydroxyjasmonic acid
Description7-epi-12-hydroxyjasmonic acid, also known as (+)-12-hydroxy-7-isojasmonate, is a member of the class of compounds known as jasmonic acids. Jasmonic acids are lipids containing or derived from a jasmonic acid, with a structure characterized by the presence of an alkene chain linked to a 2-(3-oxocyclopentyl)acetic acid moiety. Thus, 7-epi-12-hydroxyjasmonic acid is considered to be an octadecanoid lipid molecule. 7-epi-12-hydroxyjasmonic acid is slightly soluble (in water) and a weakly acidic compound (based on its pKa). 7-epi-12-hydroxyjasmonic acid can be synthesized from (+)-7-isojasmonic acid. 7-epi-12-hydroxyjasmonic acid can also be synthesized into N-[(+)-12-hydroxy-7-isojasmonyl]-L-isoleucine and methyl tuberonate. 7-epi-12-hydroxyjasmonic acid can be found in potato, which makes 7-epi-12-hydroxyjasmonic acid a potential biomarker for the consumption of this food product.
Structure
Thumb
Synonyms
ValueSource
(+)-12-Hydroxy-7-isojasmonic acidChEBI
(1R,2S)-3-oxo-2-(5'-Hydroxy-2'z-pentenyl)-cyclopentaneacetic acidChEBI
12-Hydroxy-epi-jasmonic acidChEBI
(+)-12-Hydroxy-7-isojasmonateGenerator
(1R,2S)-3-oxo-2-(5'-Hydroxy-2'z-pentenyl)-cyclopentaneacetateGenerator
12-Hydroxy-epi-jasmonateGenerator
TuberonateGenerator
7-Epi-12-hydroxyjasmonateGenerator
Chemical FormulaC12H18O4
Average Molecular Weight226.2689
Monoisotopic Molecular Weight226.120509064
IUPAC Name2-[(1R,2S)-2-[(2Z)-5-hydroxypent-2-en-1-yl]-3-oxocyclopentyl]acetic acid
Traditional Nametuberonic acid
CAS Registry NumberNot Available
SMILES
OCC\C=C/C[C@H]1[C@@H](CC(O)=O)CCC1=O
InChI Identifier
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
InChI KeyRZGFUGXQKMEMOO-SZXTZRQCSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as jasmonic acids. These are lipids containing or derived from a jasmonic acid, with a structure characterized by the presence of an alkene chain linked to a 2-(3-oxocyclopentyl)acetic acid moiety.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassLineolic acids and derivatives
Direct ParentJasmonic acids
Alternative Parents
Substituents
  • Jasmonic acid
  • Fatty alcohol
  • Cyclic ketone
  • Ketone
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Primary alcohol
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB020508
KNApSAcK IDC00000221
Chemspider ID4947920
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound6443968
PDB IDNot Available
ChEBI ID133220
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available