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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-12 00:53:27 UTC
Update Date2019-07-23 06:29:33 UTC
HMDB IDHMDB0039427
Secondary Accession Numbers
  • HMDB39427
Metabolite Identification
Common Name2-Hydroxy-3-(4-methoxyphenyl)propanoic acid
Description2-Hydroxy-3-(4-methoxyphenyl)propanoic acid is found in cereals and cereal products. 2-Hydroxy-3-(4-methoxyphenyl)propanoic acid is a constituent of wheat, rye (Secale cereale), and barley (Hordeum vulgore).
Structure
Data?1563863373
SynonymsNot Available
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
DescriptionThis compound belongs to the class of organic compounds known as phenylpropanoic acids. These 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
Disposition

Route of exposure:

Source:

Biological location:

Role

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point104 - 105 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted 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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0fkc-3900000000-89f7497ce29140e69b71JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-0100-9362000000-a9b7fc61dc2b5ea348d1JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-002b-0900000000-6ccbe4588ea44935fe6cJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ufs-0900000000-b29089901e38719e69d7JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-4900000000-d2af3de1cc46914070c2JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-1900000000-74676802bd7f6840f11fJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0fdk-1900000000-5e2c775322a1993e89e9JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0abi-3900000000-cfe6f037808518919f3eJSpectraViewer | MoNA
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
FoodDB 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 IDNot Available
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