Showing metabocard for Desaminotyrosine (LMDB00383)

IdentificationTaxonomyOntologyPhysical propertiesSpectraBiological propertiesConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-07-13 19:48:37 UTC
Update Date2016-09-23 18:45:18 UTC
LmdbLMDB00383
Secondary Accession NumbersNone
Metabolite Identification
Common NameDesaminotyrosine
DescriptionDesaminotyrosine, also known as phloretinic acid or dihydro-p-coumarate, belongs to the class of organic compounds known as phenylpropanoic acids. Phenylpropanoic acids are compounds with a structure containing a benzene ring conjugated to a propanoic acid. Desaminotyrosine is found, on average, in the highest concentration within olives (Olea europaea) and beer. Desaminotyrosine has also been detected, but not quantified in, several different foods, such as anatidaes (Anatidae), domestic pigs (Sus scrofa domestica), avocados (Persea americana), chickens (Gallus gallus), and peanuts (Arachis hypogaea). This could make desaminotyrosine a potential biomarker for the consumption of these foods. Desaminotyrosine is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Based on a literature review a significant number of articles have been published on Desaminotyrosine.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
3-(p-Hydroxyphenyl)propionic acidChEBI
4-Hydroxyphenylpropionic acidChEBI
beta-(p-Hydroxyphenyl)propionic acidChEBI
Dihydro-p-coumaric acidChEBI
HYDROXYPHENYL propionIC ACIDChEBI
p-Hydroxyhydrocinnamic acidChEBI
p-Hydroxyphenylpropionic acidChEBI
Phloretinic acidChEBI
3-(4-Hydroxyphenyl)propanoateKegg
3-(4-Hydroxyphenyl)propionateGenerator
3-(p-Hydroxyphenyl)propionateGenerator
4-HydroxyphenylpropionateGenerator
b-(p-Hydroxyphenyl)propionateGenerator
b-(p-Hydroxyphenyl)propionic acidGenerator
beta-(p-Hydroxyphenyl)propionateGenerator
Β-(p-hydroxyphenyl)propionateGenerator
Β-(p-hydroxyphenyl)propionic acidGenerator
Dihydro-p-coumarateGenerator
HYDROXYPHENYL propionateGenerator
p-HydroxyhydrocinnamateGenerator
p-HydroxyphenylpropionateGenerator
PhloretinateGenerator
PhloretateGenerator
3-(4-Hydroxyphenyl)propanoic acidGenerator
3-(4'-Hydroxyphenyl)-propionateHMDB
3-(4'-Hydroxyphenyl)-propionic acidHMDB
3-(4'-Hydroxyphenyl)propionic acidHMDB
3-(4-Hydroxy-phenyl)-propionateHMDB
3-(4-Hydroxy-phenyl)-propionic acidHMDB
3-(4-Hydroxyphenyl)-propionateHMDB
3-(4-Hydroxyphenyl)-propionic acidHMDB
3-(Para-hydroxyphenyl)propionateHMDB
3-(Para-hydroxyphenyl)propionic acidHMDB
4'-Hydroxyphenylpropionic acidHMDB
4-(4-HydroxyphenylpropanoateHMDB
4-(4-Hydroxyphenylpropanoic acidHMDB
4-Hydroxy-(9ci)benzenepropanoateHMDB
4-Hydroxy-(9ci)benzenepropanoic acidHMDB
4-Hydroxy-benzenepropanoateHMDB
4-Hydroxy-benzenepropanoic acidHMDB
4-HydroxybenzenepropanoateHMDB
4-Hydroxybenzenepropanoic acidHMDB
hydro-P-CoumarateHMDB
Hydro-p-coumaric acidHMDB
Hydroxy-hydrocinnamic acidHMDB
N-Hydroxysuccinimide esterHMDB
P-Hydroxy-benzene propionateHMDB
P-Hydroxy-benzene propionic acidHMDB
P-Hydroxy-hydrocinnamateHMDB
P-Hydroxy-hydrocinnamic acidHMDB
4-Hydroxyhydrocinnamic acidMeSH, HMDB
DesaminotyrosineChEBI
3-(4'-Hydroxyphenyl)propanoic acidPhytoBank
4-Hydroxybenzenepropionic acidPhytoBank
2,3-Dihydro-p-coumaric acidPhytoBank
3-(4’-Hydroxyphenyl)propanoic acidPhytoBank
3-(4’-Hydroxyphenyl)propionic acidPhytoBank
3-(p-Hydroxyphenyl)propanoic acidPhytoBank
4-(2-Carboxyethyl)phenolPhytoBank
4-(2-Carboxylethyl)phenolPhytoBank
4-Hydroxydihydrocinnamic acidPhytoBank
Dihydrocoumaric acidPhytoBank
p-Hydroxybenzene propanoic acidPhytoBank
p-Hydroxybenzene propionic acidPhytoBank
p-Hydroxyphenylpropanoic acidPhytoBank
beta-(4-Hydroxyphenyl)propanoic acidPhytoBank
beta-(4-Hydroxyphenyl)propionic acidPhytoBank
β-(4-Hydroxyphenyl)propanoic acidPhytoBank
β-(4-Hydroxyphenyl)propionic acidPhytoBank
beta-(p-Hydroxyphenyl)propanoic acidPhytoBank
β-(p-Hydroxyphenyl)propanoic acidPhytoBank
Chemical FormulaC9H10O3
Average Molecular Weight166.1739
Monoisotopic Molecular Weight166.062994186
IUPAC Name3-(4-hydroxyphenyl)propanoic acid
Traditional Namehydroxyphenyl propionic acid
CAS Registry Number501-97-3
SMILES
OC(=O)CCC1=CC=C(O)C=C1
InChI Identifier
InChI=1S/C9H10O3/c10-8-4-1-7(2-5-8)3-6-9(11)12/h1-2,4-5,10H,3,6H2,(H,11,12)
InChI KeyNMHMNPHRMNGLLB-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as phenylpropanoic acids. Phenylpropanoic acids are compounds with a structure containing a benzene ring conjugated to a propanoic acid.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassPhenylpropanoic acids
Sub ClassNot Available
Direct ParentPhenylpropanoic acids
Alternative Parents
Substituents
  • 3-phenylpropanoic-acid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Benzenoid
  • Monocyclic benzene moiety
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
StatusDetected but not Quantified
OriginNot Available
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP1.15ALOGPS
logP1.75ChemAxon
logS-1.8ALOGPS
pKa (Strongest Acidic)4.21ChemAxon
pKa (Strongest Basic)-6ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity43.95 m³·mol⁻¹ChemAxon
Polarizability16.97 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-066r-9800000000-44e113d8fc2602ffba88Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-004l-0900000000-5ae3f727b5218398aa83Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-066r-9800000000-44e113d8fc2602ffba88Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-004l-0900000000-5ae3f727b5218398aa83Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0ab9-3900000000-424e95de0b8037c4aa20Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-00g0-9660000000-261dcfd72b0dbd1c03dfSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-00kv-5900000000-db98339dadc21116c7aaSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-052r-9400000000-7d2340d4f6981ee8aecbSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-00bi-9100000000-cac6ca239c2cbe36238dSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-014i-0900000000-e131522c5a7352167afbSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-014i-3900000000-5c5920f4693d31baa640Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-0a4i-9500000000-49bd07916272cdc49e68Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-0a6u-9100000000-683b03c9384a9a750863Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-00di-9000000000-d4af6cba1b370fd620edSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-014i-0900000000-514be816ed648e5588b7Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-014i-3900000000-5c5920f4693d31baa640Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0a4i-9500000000-49bd07916272cdc49e68Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0a6u-9100000000-683b03c9384a9a750863Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-00di-9000000000-d4af6cba1b370fd620edSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014j-0900000000-3603746465916eaf1e98Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0601-1900000000-a85683e512fff2c291ddSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0kdi-9500000000-dbb0fa659379ccf4eb26Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0900000000-17bb794e8bbfe1aad6b3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01b9-1900000000-9708817125183e0214a3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9400000000-d9a164ed2938481885d9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-066r-5900000000-6672a989c0ad56cb1697Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-05fu-8900000000-f2a5c52c26b284a94a51Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9300000000-179e6648decb5dd31953Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0aba-0900000000-3631ad60fd3a5053aacfSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-2900000000-28c2e194d667a26ec152Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004i-9300000000-20c3b533b0eccb02601eSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableSpectrum
Biological Properties
Cellular LocationsNot Available
Biofluid Locations and Tissue Locations
  • Ruminal Fluid
Concentrations
BiofluidStatusValueConditionSpeciesReferenceDetails
Ruminal FluidDetected but not QuantifiedNot ApplicableNot AvailableBovine details
DrugBank IDDB03897
HMDB IDHMDB0002199
FooDB IDFDB000849
Phenol Explorer ID578
KNApSAcK IDC00029471
BiGG IDNot Available
BioCyc ID2-3-DIHYDROXYPHENYL-PROPIONATE
METLIN ID4148
PDB IDNot Available
Wikipedia LinkPhloretic acid
Chemspider ID9965
ChEBI ID32980
PubChem Compound ID10394
Kegg Compound IDC01744
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Ward NC, Croft KD, Puddey IB, Hodgson JM: Supplementation with grape seed polyphenols results in increased urinary excretion of 3-hydroxyphenylpropionic Acid, an important metabolite of proanthocyanidins in humans. J Agric Food Chem. 2004 Aug 25;52(17):5545-9. [15315398 ]