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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2012-09-11 17:29:33 UTC
Update Date2022-03-07 02:52:07 UTC
HMDB IDHMDB0029304
Secondary Accession Numbers
  • HMDB29304
Metabolite Identification
Common Name3,4-DHPEA-EA
Description3,4-DHPEA-EA 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. Based on a literature review a small amount of articles have been published on 3,4-DHPEA-EA.
Structure
Data?1582753399
Synonyms
ValueSource
3,4-DHPEA-elenolic acid mono-aldehydeHMDB
Oleuropein-aglycone mono-aldehydeHMDB
Methyl (2R,4S)-4-{2-[2-(3,4-dihydroxyphenyl)ethoxy]-2-oxoethyl}-3-ethylidene-2-hydroxy-3,4-dihydro-2H-pyran-5-carboxylic acidGenerator
3,4-Dixydroxyphenylethanol elenolic acidMeSH
3,4-DHPEA-eaMeSH
Chemical FormulaC19H22O8
Average Molecular Weight378.3732
Monoisotopic Molecular Weight378.13146768
IUPAC Namemethyl (2R,3Z,4S)-4-{2-[2-(3,4-dihydroxyphenyl)ethoxy]-2-oxoethyl}-3-ethylidene-2-hydroxy-3,4-dihydro-2H-pyran-5-carboxylate
Traditional Namemethyl (4S,5Z,6R)-4-{2-[2-(3,4-dihydroxyphenyl)ethoxy]-2-oxoethyl}-5-ethylidene-6-hydroxy-4,6-dihydropyran-3-carboxylate
CAS Registry NumberNot Available
SMILES
COC(=O)C1=CO[C@@H](O)\C(=C/C)[C@@H]1CC(=O)OCCC1=CC=C(O)C(O)=C1
InChI Identifier
InChI=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-SQOYHTLWSA-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
Ontology
Physiological effectNot Available
Disposition
Process
Role
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
PropertyValueSource
Water Solubility0.042 g/LALOGPS
logP2.16ALOGPS
logP1.88ChemAxon
logS-4ALOGPS
pKa (Strongest Acidic)9.28ChemAxon
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+190.34430932474
DeepCCS[M-H]-187.94830932474
DeepCCS[M-2H]-220.94130932474
DeepCCS[M+Na]+196.25630932474
AllCCS[M+H]+189.132859911
AllCCS[M+H-H2O]+186.332859911
AllCCS[M+NH4]+191.632859911
AllCCS[M+Na]+192.332859911
AllCCS[M-H]-186.932859911
AllCCS[M+Na-2H]-187.332859911
AllCCS[M+HCOO]-187.832859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
3,4-DHPEA-EACOC(=O)C1=CO[C@@H](O)\C(=C/C)[C@@H]1CC(=O)OCCC1=CC=C(O)C(O)=C14529.1Standard polar33892256
3,4-DHPEA-EACOC(=O)C1=CO[C@@H](O)\C(=C/C)[C@@H]1CC(=O)OCCC1=CC=C(O)C(O)=C12926.1Standard non polar33892256
3,4-DHPEA-EACOC(=O)C1=CO[C@@H](O)\C(=C/C)[C@@H]1CC(=O)OCCC1=CC=C(O)C(O)=C13015.4Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
3,4-DHPEA-EA,1TMS,isomer #1C/C=C1\[C@H](O[Si](C)(C)C)OC=C(C(=O)OC)[C@H]1CC(=O)OCCC1=CC=C(O)C(O)=C12939.3Semi standard non polar33892256
3,4-DHPEA-EA,1TMS,isomer #2C/C=C1/[C@H](CC(=O)OCCC2=CC=C(O[Si](C)(C)C)C(O)=C2)C(C(=O)OC)=CO[C@H]1O2926.5Semi standard non polar33892256
3,4-DHPEA-EA,1TMS,isomer #3C/C=C1/[C@H](CC(=O)OCCC2=CC=C(O)C(O[Si](C)(C)C)=C2)C(C(=O)OC)=CO[C@H]1O2923.4Semi standard non polar33892256
3,4-DHPEA-EA,2TMS,isomer #1C/C=C1\[C@H](O[Si](C)(C)C)OC=C(C(=O)OC)[C@H]1CC(=O)OCCC1=CC=C(O[Si](C)(C)C)C(O)=C12921.6Semi standard non polar33892256
3,4-DHPEA-EA,2TMS,isomer #2C/C=C1\[C@H](O[Si](C)(C)C)OC=C(C(=O)OC)[C@H]1CC(=O)OCCC1=CC=C(O)C(O[Si](C)(C)C)=C12923.6Semi standard non polar33892256
3,4-DHPEA-EA,2TMS,isomer #3C/C=C1/[C@H](CC(=O)OCCC2=CC=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C2)C(C(=O)OC)=CO[C@H]1O2960.2Semi standard non polar33892256
3,4-DHPEA-EA,3TMS,isomer #1C/C=C1\[C@H](O[Si](C)(C)C)OC=C(C(=O)OC)[C@H]1CC(=O)OCCC1=CC=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C12989.0Semi standard non polar33892256
3,4-DHPEA-EA,1TBDMS,isomer #1C/C=C1\[C@H](O[Si](C)(C)C(C)(C)C)OC=C(C(=O)OC)[C@H]1CC(=O)OCCC1=CC=C(O)C(O)=C13160.2Semi standard non polar33892256
3,4-DHPEA-EA,1TBDMS,isomer #2C/C=C1/[C@H](CC(=O)OCCC2=CC=C(O[Si](C)(C)C(C)(C)C)C(O)=C2)C(C(=O)OC)=CO[C@H]1O3168.4Semi standard non polar33892256
3,4-DHPEA-EA,1TBDMS,isomer #3C/C=C1/[C@H](CC(=O)OCCC2=CC=C(O)C(O[Si](C)(C)C(C)(C)C)=C2)C(C(=O)OC)=CO[C@H]1O3164.8Semi standard non polar33892256
3,4-DHPEA-EA,2TBDMS,isomer #1C/C=C1\[C@H](O[Si](C)(C)C(C)(C)C)OC=C(C(=O)OC)[C@H]1CC(=O)OCCC1=CC=C(O[Si](C)(C)C(C)(C)C)C(O)=C13371.7Semi standard non polar33892256
3,4-DHPEA-EA,2TBDMS,isomer #2C/C=C1\[C@H](O[Si](C)(C)C(C)(C)C)OC=C(C(=O)OC)[C@H]1CC(=O)OCCC1=CC=C(O)C(O[Si](C)(C)C(C)(C)C)=C13361.5Semi standard non polar33892256
3,4-DHPEA-EA,2TBDMS,isomer #3C/C=C1/[C@H](CC(=O)OCCC2=CC=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C2)C(C(=O)OC)=CO[C@H]1O3404.5Semi standard non polar33892256
3,4-DHPEA-EA,3TBDMS,isomer #1C/C=C1\[C@H](O[Si](C)(C)C(C)(C)C)OC=C(C(=O)OC)[C@H]1CC(=O)OCCC1=CC=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C13594.5Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 3,4-DHPEA-EA GC-MS (Non-derivatized) - 70eV, Positivesplash10-0002-3924000000-a774df901c6e416aa9792017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3,4-DHPEA-EA GC-MS (3 TMS) - 70eV, Positivesplash10-0059-6040090000-2e8e4c02704c1060b4582017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3,4-DHPEA-EA GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,4-DHPEA-EA 10V, Positive-QTOFsplash10-004i-0769000000-44f59fc6a7f7eccf78b12016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,4-DHPEA-EA 20V, Positive-QTOFsplash10-000i-0922000000-cfa03854b1f3f2e1d6922016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,4-DHPEA-EA 40V, Positive-QTOFsplash10-000i-6910000000-af8e65043b5cc4bd20272016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,4-DHPEA-EA 10V, Negative-QTOFsplash10-00b9-1549000000-0f8a81848af23892f8242016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,4-DHPEA-EA 20V, Negative-QTOFsplash10-00dm-1984000000-400bc643c703ff71eca92016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,4-DHPEA-EA 40V, Negative-QTOFsplash10-0abi-1900000000-af441007a9141cc14c962016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,4-DHPEA-EA 10V, Negative-QTOFsplash10-004i-0129000000-3f25a8adebbfe0f30b8e2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,4-DHPEA-EA 20V, Negative-QTOFsplash10-00vi-0926000000-196f5729bb68656d092a2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,4-DHPEA-EA 40V, Negative-QTOFsplash10-00di-1911000000-aefd6a7daecc217d4d112021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,4-DHPEA-EA 10V, Positive-QTOFsplash10-03fr-0129000000-6f49095caa9d91c93b252021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,4-DHPEA-EA 20V, Positive-QTOFsplash10-000i-0903000000-43a413396c8163d27ce72021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,4-DHPEA-EA 40V, Positive-QTOFsplash10-01di-5902000000-66e3b9f0e854cf50afa22021-09-24Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen Locations
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound ID688
FooDB IDFDB000346
KNApSAcK IDNot Available
Chemspider ID30776771
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound56842347
PDB IDNot Available
ChEBI ID89421
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 References
  1. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  2. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
  3. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
  4. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
  5. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.