Oleuropein-aglycone (CHEM023028)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 20:47:27 UTC
Update Date2016-11-09 01:17:37 UTC
Accession NumberCHEM023028
Identification
Common NameOleuropein-aglycone
ClassSmall Molecule
DescriptionA secoiridoid that is the methyl ester of 3,4-dihydro-2H-pyran-5-carboxylic acid which is substituted at positions 2, 3, and 4 by hydroxy, ethylidene, and carboxymethyl groups, respectively and in which the carboxylic acid moiety of the carboxymethyl substituent has been converted to the corresponding 3,4-dihydroxyphenethyl ester (the 2R,3E,4S stereoisomer). The most important phenolic compound present in olive cultivars.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
SynonymsNot Available
Chemical FormulaC19H22O8
Average Molecular Mass378.373 g/mol
Monoisotopic Mass378.131 g/mol
CAS Registry NumberNot Available
IUPAC Namemethyl (2R,3E,4S)-4-{2-[2-(3,4-dihydroxyphenyl)ethoxy]-2-oxoethyl}-3-ethylidene-2-hydroxy-3,4-dihydro-2H-pyran-5-carboxylate
Traditional Namemethyl (4S,5E,6R)-4-{2-[2-(3,4-dihydroxyphenyl)ethoxy]-2-oxoethyl}-5-ethylidene-6-hydroxy-4,6-dihydropyran-3-carboxylate
SMILESCOC(=O)C1=CO[C@@H](O)\C(=C\C)[C@@H]1CC(=O)OCCC1=CC(O)=C(O)C=C1
InChI IdentifierInChI=1S/C19H22O8/c1-3-12-13(14(18(23)25-2)10-27-19(12)24)9-17(22)26-7-6-11-4-5-15(20)16(21)8-11/h3-5,8,10,13,19-21,24H,6-7,9H2,1-2H3/b12-3+/t13-,19+/m0/s1
InChI KeyBIWKXNFEOZXNLX-BBHIFXBUSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as iridoids and derivatives. These are monoterpenes containing a skeleton structurally characterized by the presence of a cylopentane fused to a pyran ( forming a 4,7-dimethylcyclopenta[c]pyran), or a derivative where the pentane moiety is open.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassMonoterpenoids
Direct ParentIridoids and derivatives
Alternative Parents
Substituents
  • Secoiridoid-skeleton
  • Aromatic monoterpenoid
  • Monocyclic monoterpenoid
  • Tyrosol derivative
  • Catechol
  • 1-hydroxy-4-unsubstituted benzenoid
  • Phenol
  • 1-hydroxy-2-unsubstituted benzenoid
  • Monocyclic benzene moiety
  • Benzenoid
  • Dicarboxylic acid or derivatives
  • Vinylogous ester
  • Alpha,beta-unsaturated carboxylic ester
  • Enoate ester
  • Methyl ester
  • Carboxylic acid ester
  • Hemiacetal
  • Oxacycle
  • Carboxylic acid derivative
  • Organoheterocyclic compound
  • Organic oxide
  • Hydrocarbon derivative
  • Carbonyl group
  • Organooxygen compound
  • Organic oxygen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.042 g/LALOGPS
logP2.16ALOGPS
logP1.88ChemAxon
logS-4ALOGPS
pKa (Strongest Acidic)4.95ChemAxon
pKa (Strongest Basic)-4.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area122.52 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity95.8 m³·mol⁻¹ChemAxon
Polarizability37.88 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0769000000-44f59fc6a7f7eccf78b1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0922000000-cfa03854b1f3f2e1d692Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-6910000000-af8e65043b5cc4bd2027Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00b9-1549000000-0f8a81848af23892f824Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00dm-1984000000-400bc643c703ff71eca9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0abi-1900000000-af441007a9141cc14c96Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01t9-0129000000-5d8114d30567f0aa72eaSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0904000000-fd10d111a98b9def4285Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-1900000000-ab856294531d2f1942fbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0149000000-e40656840775b87aa431Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004r-0926000000-2ee29f79bfb02793782bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00di-2911000000-d2f7d792663a2720efd0Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0301749
FooDB IDFDB000351
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDCPD-20219
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID25936979
ChEBI ID139162
PubChem Compound IDNot Available
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=15715252
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=21411195
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=21880869
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=22342994
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=23233730
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=23520540
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=23951225
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=24211687
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=25293421
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=25649656
11. https://www.ncbi.nlm.nih.gov/pubmed/?term=25697790
12. https://www.ncbi.nlm.nih.gov/pubmed/?term=26278640
13. https://www.ncbi.nlm.nih.gov/pubmed/?term=26474288
14. https://www.ncbi.nlm.nih.gov/pubmed/?term=27012632
15. https://www.ncbi.nlm.nih.gov/pubmed/?term=27131215
16. https://www.ncbi.nlm.nih.gov/pubmed/?term=27455905
17. https://www.ncbi.nlm.nih.gov/pubmed/?term=27567859
18. https://www.ncbi.nlm.nih.gov/pubmed/?term=27951473
19. https://www.ncbi.nlm.nih.gov/pubmed/?term=28483880
20. https://www.ncbi.nlm.nih.gov/pubmed/?term=29160876