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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-12 00:53:27 UTC
Update Date2023-02-21 17:26:56 UTC
HMDB IDHMDB0039427
Secondary Accession Numbers
  • HMDB39427
Metabolite Identification
Common Name2-Hydroxy-3-(4-methoxyphenyl)propanoic acid
Description2-Hydroxy-3-(4-methoxyphenyl)propanoic acid 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. 2-Hydroxy-3-(4-methoxyphenyl)propanoic acid has been detected, but not quantified in, a few different foods, such as breakfast cereal, cereals and cereal products, and ryes (Secale cereale). This could make 2-hydroxy-3-(4-methoxyphenyl)propanoic acid a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on 2-Hydroxy-3-(4-methoxyphenyl)propanoic acid.
Structure
Data?1677000416
Synonyms
ValueSource
2-Hydroxy-3-(4-methoxyphenyl)propanoateGenerator
2-Hydroxy-4'-methoxyphloretateGenerator
Chemical FormulaC10H12O4
Average Molecular Weight196.1999
Monoisotopic Molecular Weight196.073558872
IUPAC Name2-hydroxy-3-(4-methoxyphenyl)propanoic acid
Traditional Name2-hydroxy-3-(4-methoxyphenyl)propanoic acid
CAS Registry Number28030-15-1
SMILES
COC1=CC=C(CC(O)C(O)=O)C=C1
InChI Identifier
InChI=1S/C10H12O4/c1-14-8-4-2-7(3-5-8)6-9(11)10(12)13/h2-5,9,11H,6H2,1H3,(H,12,13)
InChI KeyGEDLJGYFEOYKEG-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
  • Phenoxy compound
  • Anisole
  • Phenol ether
  • Methoxybenzene
  • Alkyl aryl ether
  • Alpha-hydroxy acid
  • Monocyclic benzene moiety
  • Hydroxy acid
  • Benzenoid
  • Secondary alcohol
  • Monocarboxylic acid or derivatives
  • Ether
  • Carboxylic acid
  • Carboxylic acid derivative
  • Alcohol
  • Carbonyl group
  • Organic oxygen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point104 - 105 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility39090 mg/L @ 25 °C (est)The Good Scents Company Information System
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility7.02 g/LALOGPS
logP0.92ALOGPS
logP1.03ChemAxon
logS-1.4ALOGPS
pKa (Strongest Acidic)3.68ChemAxon
pKa (Strongest Basic)-3.8ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area66.76 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity49.92 m³·mol⁻¹ChemAxon
Polarizability19.8 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+144.76131661259
DarkChem[M-H]-144.12131661259
DeepCCS[M+H]+141.60430932474
DeepCCS[M-H]-139.23630932474
DeepCCS[M-2H]-174.4630932474
DeepCCS[M+Na]+149.71430932474
AllCCS[M+H]+144.232859911
AllCCS[M+H-H2O]+140.132859911
AllCCS[M+NH4]+148.032859911
AllCCS[M+Na]+149.132859911
AllCCS[M-H]-143.532859911
AllCCS[M+Na-2H]-144.232859911
AllCCS[M+HCOO]-145.032859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
2-Hydroxy-3-(4-methoxyphenyl)propanoic acidCOC1=CC=C(CC(O)C(O)=O)C=C13190.9Standard polar33892256
2-Hydroxy-3-(4-methoxyphenyl)propanoic acidCOC1=CC=C(CC(O)C(O)=O)C=C11685.0Standard non polar33892256
2-Hydroxy-3-(4-methoxyphenyl)propanoic acidCOC1=CC=C(CC(O)C(O)=O)C=C11760.0Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
2-Hydroxy-3-(4-methoxyphenyl)propanoic acid,1TMS,isomer #1COC1=CC=C(CC(O[Si](C)(C)C)C(=O)O)C=C11816.7Semi standard non polar33892256
2-Hydroxy-3-(4-methoxyphenyl)propanoic acid,1TMS,isomer #2COC1=CC=C(CC(O)C(=O)O[Si](C)(C)C)C=C11756.2Semi standard non polar33892256
2-Hydroxy-3-(4-methoxyphenyl)propanoic acid,2TMS,isomer #1COC1=CC=C(CC(O[Si](C)(C)C)C(=O)O[Si](C)(C)C)C=C11812.8Semi standard non polar33892256
2-Hydroxy-3-(4-methoxyphenyl)propanoic acid,1TBDMS,isomer #1COC1=CC=C(CC(O[Si](C)(C)C(C)(C)C)C(=O)O)C=C12080.8Semi standard non polar33892256
2-Hydroxy-3-(4-methoxyphenyl)propanoic acid,1TBDMS,isomer #2COC1=CC=C(CC(O)C(=O)O[Si](C)(C)C(C)(C)C)C=C12003.8Semi standard non polar33892256
2-Hydroxy-3-(4-methoxyphenyl)propanoic acid,2TBDMS,isomer #1COC1=CC=C(CC(O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C)C=C12310.3Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 2-Hydroxy-3-(4-methoxyphenyl)propanoic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-0fkc-3900000000-89f7497ce29140e69b712017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Hydroxy-3-(4-methoxyphenyl)propanoic acid GC-MS (2 TMS) - 70eV, Positivesplash10-0100-9362000000-a9b7fc61dc2b5ea348d12017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Hydroxy-3-(4-methoxyphenyl)propanoic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Hydroxy-3-(4-methoxyphenyl)propanoic acid 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 - 2-Hydroxy-3-(4-methoxyphenyl)propanoic acid 10V, Positive-QTOFsplash10-002b-0900000000-6ccbe4588ea44935fe6c2016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Hydroxy-3-(4-methoxyphenyl)propanoic acid 20V, Positive-QTOFsplash10-0ufs-0900000000-b29089901e38719e69d72016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Hydroxy-3-(4-methoxyphenyl)propanoic acid 40V, Positive-QTOFsplash10-0a4i-4900000000-d2af3de1cc46914070c22016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Hydroxy-3-(4-methoxyphenyl)propanoic acid 10V, Negative-QTOFsplash10-0002-1900000000-74676802bd7f6840f11f2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Hydroxy-3-(4-methoxyphenyl)propanoic acid 20V, Negative-QTOFsplash10-0fdk-1900000000-5e2c775322a1993e89e92016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Hydroxy-3-(4-methoxyphenyl)propanoic acid 40V, Negative-QTOFsplash10-0abi-3900000000-cfe6f037808518919f3e2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Hydroxy-3-(4-methoxyphenyl)propanoic acid 10V, Negative-QTOFsplash10-00di-9200000000-7dd61f7a544cfbeea2a22021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Hydroxy-3-(4-methoxyphenyl)propanoic acid 20V, Negative-QTOFsplash10-00di-9300000000-95b440432758389c7f472021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Hydroxy-3-(4-methoxyphenyl)propanoic acid 40V, Negative-QTOFsplash10-0a70-8900000000-152ee7d9babd0a7ff13d2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Hydroxy-3-(4-methoxyphenyl)propanoic acid 10V, Positive-QTOFsplash10-0f92-0900000000-5c27ea8c1ae5475e73ef2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Hydroxy-3-(4-methoxyphenyl)propanoic acid 20V, Positive-QTOFsplash10-00di-3900000000-157ec5bc8dedd58b7f492021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Hydroxy-3-(4-methoxyphenyl)propanoic acid 40V, Positive-QTOFsplash10-00bc-9500000000-a0faf64a91f6d7cbdeee2021-09-24Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)2023-02-04FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)2023-02-04FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)2023-02-04FELIX labView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
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 IDFDB019022
KNApSAcK IDNot Available
Chemspider ID14060380
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound14868260
PDB IDNot Available
ChEBI ID173970
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1622281
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Enzymes

General function:
Involved in sulfotransferase activity
Specific function:
Sulfotransferase that utilizes 3'-phospho-5'-adenylyl sulfate (PAPS) as sulfonate donor to catalyze the sulfate conjugation of many hormones, neurotransmitters, drugs and xenobiotic compounds. Sulfonation increases the water solubility of most compounds, and therefore their renal excretion, but it can also result in bioactivation to form active metabolites. Sulfates hydroxysteroids like DHEA. Isoform 1 preferentially sulfonates cholesterol, and isoform 2 avidly sulfonates pregnenolone but not cholesterol.
Gene Name:
SULT2B1
Uniprot ID:
O00204
Molecular weight:
39598.595
Reactions
2-Hydroxy-3-(4-methoxyphenyl)propanoic acid → 3-(4-methoxyphenyl)-2-(sulfooxy)propanoic aciddetails
General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone.
Gene Name:
UGT1A1
Uniprot ID:
P22309
Molecular weight:
59590.91
Reactions
2-Hydroxy-3-(4-methoxyphenyl)propanoic acid → 6-[1-carboxy-2-(4-methoxyphenyl)ethoxy]-3,4,5-trihydroxyoxane-2-carboxylic aciddetails
2-Hydroxy-3-(4-methoxyphenyl)propanoic acid → 3,4,5-trihydroxy-6-{[2-hydroxy-3-(4-methoxyphenyl)propanoyl]oxy}oxane-2-carboxylic aciddetails