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Record Information
Version3.6
Creation Date2006-05-22 14:17:41 UTC
Update Date2017-08-16 03:55:57 UTC
HMDB IDHMDB0002199
Secondary Accession Numbers
  • HMDB02199
  • HMDB61145
Metabolite Identification
Common NameDesaminotyrosine
DescriptionDesaminotyrosine is a normal constituent of human urine. A product of tyrosine metabolism; concentration in urine increases in patients with gastrointestinal diseases. (Dictionary of Organic Compounds). It is considered also that may result from metabolism to phenolic acids by colonic bacteria. (PMID 15315398 ).
Structure
Thumb
Synonyms
ValueSource
3-(4-Hydroxyphenyl)propionic acidChEBI
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)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
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-(4-Hydroxyphenyl)propanoateHMDB
3-(4-Hydroxyphenyl)propanoic 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
PhloretateHMDB
Phloretic acidHMDB
4-Hydroxyhydrocinnamic acidMeSH
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
DescriptionThis compound belongs to the class of chemical entities known as phenylpropanoic acids. These are compounds with a structure containing a benzene ring conjugated to a propanoic acid.
KingdomChemical entities
Super ClassOrganic compounds
ClassPhenylpropanoids and polyketides
Sub ClassPhenylpropanoic acids
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 and Quantified
Origin
  • Drug metabolite
  • Endogenous
  • Microbial
Biofunction
  • Waste products
ApplicationNot Available
Cellular locations
  • Cytoplasm
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point129 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP1.16HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
Water Solubility2.71 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity43.95 m3·mol-1ChemAxon
Polarizability16.97 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MSNot Available
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-00kv-5900000000-db98339dadc21116c7aaView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-052r-9400000000-7d2340d4f6981ee8aecbView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-00bi-9100000000-cac6ca239c2cbe36238dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-014i-0900000000-e131522c5a7352167afbView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-014i-3900000000-5c5920f4693d31baa640View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-0a4i-9500000000-49bd07916272cdc49e68View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-0a6u-9100000000-683b03c9384a9a750863View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-00di-9000000000-d4af6cba1b370fd620edView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-014i-0900000000-514be816ed648e5588b7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
1D NMR1H NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
Biological Properties
Cellular Locations
  • Cytoplasm
Biofluid Locations
  • Blood
  • Feces
  • Saliva
  • Urine
Tissue Location
  • Kidney
  • Liver
  • Spleen
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry details
BloodDetected and Quantified0.664 +/- 0.089 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified0.628 +/- 0.075 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified0.712 +/- 0.088 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified0.705 +/- 0.1 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified0.701 +/- 0.071 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified0.69 +/- 0.099 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified0.574 +/- 0.078 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified3.189 +/- 2.633 uMAdult (>18 years old)Male
Normal
details
BloodExpected but not Quantified Not AvailableNot Available
Normal
    details
    FecesDetected but not Quantified Adult (>18 years old)Both
    Normal
    details
    FecesDetected and Quantified76.426 nmol/g of fecesAdult (>18 years old)Both
    Normal
    details
    FecesDetected and Quantified131.790 +/- 93.878 nmol/g of fecesAdult (>18 years old)Both
    Normal
    details
    FecesDetected and Quantified143.825 +/- 106.515 nmol/g of fecesAdult (>18 years old)Both
    Normal
    details
    FecesDetected and Quantified184.746 +/- 169.702 nmol/g of fecesAdult (>18 years old)Both
    Normal
    details
    FecesDetected but not Quantified Adult (>18 years old)Male
    Normal
    details
    FecesDetected but not Quantified Adult (>18 years old)Male
    Normal
    details
    FecesDetected but not Quantified Adult (>18 years old)BothNormal details
    FecesDetected but not Quantified Not SpecifiedNot Specified
    Normal
    details
    FecesDetected but not Quantified Not SpecifiedBoth
    Normal
    details
    FecesDetected and Quantified16.128 +/- 15.165 uMNot SpecifiedNot Specified
    Normal
    details
    FecesDetected but not Quantified Adult (>18 years old)Both
    Normal
    details
    FecesDetected and Quantified25.877 +/- 30.0890 uMNot SpecifiedNot Specified
    Normal
    details
    FecesDetected but not Quantified Not SpecifiedNot Specified
    Normal
    details
    FecesDetected but not Quantified Infant (0-1 year old)Both
    Normal
    details
    SalivaDetected but not Quantified Adult (>18 years old)Male
    Normal
    details
    SalivaDetected but not Quantified Adult (>18 years old)Male
    Normal
    details
    SalivaDetected but not Quantified Adult (>18 years old)Male
    Normal
    details
    SalivaDetected but not Quantified Adult (>18 years old)Male
    Normal
    details
    SalivaDetected but not Quantified Adult (>18 years old)Male
    Normal
    details
    SalivaDetected but not Quantified Adult (>18 years old)Male
    Normal
    details
    SalivaDetected but not Quantified Adult (>18 years old)Male
    Normal
    details
    SalivaDetected but not Quantified Adult (>18 years old)Male
    Normal
    details
    SalivaDetected but not Quantified Adult (>18 years old)Male
    Normal
    details
    SalivaDetected but not Quantified Adult (>18 years old)Male
    Normal
    details
    SalivaDetected but not Quantified Adult (>18 years old)Not SpecifiedNormal details
    SalivaDetected and Quantified1.03 +/- 1.26 uMAdult (>18 years old)Not Specified
    Normal
      • Sugimoto et al. (...
    details
    SalivaDetected and Quantified1.32 +/- 2.81 uMAdult (>18 years old)Both
    Normal
      • Sugimoto et al. (...
    details
    SalivaDetected but not Quantified Adult (>18 years old)Male
    Normal
    details
    SalivaDetected and Quantified1.59 +/- 2.05 uMAdult (>18 years old)Not Specified
    Normal
      • Sugimoto et al. (...
    details
    SalivaDetected and Quantified1.64 +/- 1.89 uMAdult (>18 years old)Female
    Normal
      • Sugimoto et al. (...
    details
    SalivaDetected and Quantified2.02 +/- 2.48 uMAdult (>18 years old)Not Specified
    Normal
      • Sugimoto et al. (...
    details
    SalivaDetected and Quantified3.11 +/- 5.21 uMAdult (>18 years old)Not Specified
    Normal
      • Sugimoto et al. (...
    details
    UrineExpected but not Quantified Not AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry details
    UrineDetected and Quantified0.089 +/- 0.016 umol/mmol creatinineAdult (>18 years old)Male
    Normal
    details
    UrineDetected and Quantified0.2 +/- 0.041 umol/mmol creatinineAdult (>18 years old)Male
    Normal
    details
    UrineDetected and Quantified0.078 +/- 0.009 umol/mmol creatinineAdult (>18 years old)Male
    Normal
    details
    UrineDetected but not Quantified Not AvailableNot AvailableNormal details
    Abnormal Concentrations
    BiofluidStatusValueAgeSexConditionReferenceDetails
    FecesDetected but not Quantified Adult (>18 years old)Both
    Irritable bowel syndrome
    details
    FecesDetected but not Quantified Adult (>18 years old)Both
    Ulcerative colitis
    details
    FecesDetected but not Quantified Adult (>18 years old)BothICD details
    FecesDetected but not Quantified Adult (>18 years old)BothCCD details
    FecesDetected but not Quantified Adult (>18 years old)BothCCD details
    FecesDetected but not Quantified Adult (>18 years old)Both
    Irritable bowel syndrome
    details
    FecesDetected but not Quantified Adult (>18 years old)BothColorectal Cancer details
    Associated Disorders and Diseases
    Disease ReferencesNone
    Associated OMIM IDsNone
    DrugBank IDNot Available
    DrugBank Metabolite IDDBMET00869
    Phenol Explorer Compound ID578
    Phenol Explorer Metabolite IDNot Available
    FoodDB IDFDB000849
    KNApSAcK IDC00029471
    Chemspider ID9965
    KEGG Compound IDC01744
    BioCyc ID2-3-DIHYDROXYPHENYL-PROPIONATE
    BiGG IDNot Available
    Wikipedia LinkNot Available
    NuGOwiki LinkHMDB0002199
    METLIN ID4148
    PubChem Compound10394
    PDB IDHPP
    ChEBI ID32980
    References
    Synthesis ReferenceJin, Enqing. Preparation of 4-hydroxyphenylpropionic acid. Faming Zhuanli Shenqing Gongkai Shuomingshu (1998), 5 pp.
    Material Safety Data Sheet (MSDS)Download (PDF)
    General References
    1. Vickers S, Stuart EK, Hucker HB: Further studies on the metabolism of carbidopa, (minus)-L-alpha-hydrazino-3,4-dihydroxy-alpha-methylbenzenepropanoic acid monohydrate, in the human, Rhesus monkey, dog, and rat. J Med Chem. 1975 Feb;18(2):134-8. [PubMed:804550 ]
    2. Mel'nikova YaI, Kravchuk ZI, Preygerzon VA, Martsev SP: Functional activation of antibodies on modification with Pd(II) coproporphyrin I N-Hydroxysuccinimide ester. Biochemistry (Mosc). 1997 Aug;62(8):924-7. [PubMed:9360305 ]
    3. Herr JC, Woodward MP: An enzyme-linked immunosorbent assay (ELISA) for human semen identification based on a biotinylated monoclonal antibody to a seminal vesicle-specific antigen. J Forensic Sci. 1987 Mar;32(2):346-56. [PubMed:3572333 ]
    4. 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. [PubMed:15315398 ]
    5. Neurath AR, Strick N, Szmuness W, Stevens CE, Harley EJ: Radioimmunoassay of hepatitis B e-antigen (HBeAg): identification of HBeAg not associated with immunoglobulins. J Gen Virol. 1979 Mar;42(3):493-504. [PubMed:107272 ]
    6. Fargeas C, Hommel M, Maingon R, Dourado C, Monsigny M, Mayer R: Synthetic peptide-based enzyme-linked immunosorbent assay for serodiagnosis of visceral leishmaniasis. J Clin Microbiol. 1996 Feb;34(2):241-8. [PubMed:8788994 ]