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Record Information
Version4.0
StatusPredicted
Creation Date2017-09-13 12:58:59 UTC
Update Date2019-11-12 17:21:02 UTC
HMDB IDHMDB0127490
Secondary Accession NumbersNone
Metabolite Identification
Common Name3-(3,4-dihydroxy-5-methoxyphenyl)prop-2-enoic acid
Description3-(3,4-dihydroxy-5-methoxyphenyl)prop-2-enoic acid, also known as 3,4-dihydroxy-5-methoxycinnamic acid or 3-methoxycaffeic acid, belongs to the class of organic compounds known as hydroxycinnamic acids. Hydroxycinnamic acids are compounds containing an cinnamic acid where the benzene ring is hydroxylated. 3-(3,4-dihydroxy-5-methoxyphenyl)prop-2-enoic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). Ferulic acid in which the ring hydrogen at position 5 is substituted by a hydroxy group.
Structure
Data?1563875257
Synonyms
ValueSource
3,4-Dihydroxy-5-methoxycinnamic acidChEBI
3-(3,4-Dihydroxy-5-methoxyphenyl)-2-propenoic acidChEBI
3-(3,4-Dihydroxy-5-methoxyphenyl)acrylic acidChEBI
3-Methoxycaffeic acidChEBI
3,4-Dihydroxy-5-methoxycinnamateGenerator
3-(3,4-Dihydroxy-5-methoxyphenyl)-2-propenoateGenerator
3-(3,4-Dihydroxy-5-methoxyphenyl)acrylateGenerator
3-MethoxycaffeateGenerator
3-(3,4-Dihydroxy-5-methoxyphenyl)prop-2-enoateGenerator
5-HydroxyferulateGenerator, HMDB
Chemical FormulaC10H10O5
Average Molecular Weight210.185
Monoisotopic Molecular Weight210.052823422
IUPAC Name3-(3,4-dihydroxy-5-methoxyphenyl)prop-2-enoic acid
Traditional Name5-hydroxyferulic acid
CAS Registry NumberNot Available
SMILES
COC1=CC(C=CC(O)=O)=CC(O)=C1O
InChI Identifier
InChI=1S/C10H10O5/c1-15-8-5-6(2-3-9(12)13)4-7(11)10(8)14/h2-5,11,14H,1H3,(H,12,13)
InChI KeyYFXWTVLDSKSYLW-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as hydroxycinnamic acids. Hydroxycinnamic acids are compounds containing an cinnamic acid where the benzene ring is hydroxylated.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassCinnamic acids and derivatives
Sub ClassHydroxycinnamic acids and derivatives
Direct ParentHydroxycinnamic acids
Alternative Parents
Substituents
  • Cinnamic acid
  • Hydroxycinnamic acid
  • Coumaric acid or derivatives
  • Methoxyphenol
  • Phenoxy compound
  • Anisole
  • Methoxybenzene
  • Styrene
  • Phenol ether
  • Catechol
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Alkyl aryl ether
  • Phenol
  • Monocyclic benzene moiety
  • Benzenoid
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Ether
  • Organic oxygen compound
  • Carbonyl group
  • Organic oxide
  • Organooxygen compound
  • Hydrocarbon derivative
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Disposition

Source:

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
logP1.41ALOGPS
logP1.37ChemAxon
logS-2.3ALOGPS
pKa (Strongest Acidic)3.69ChemAxon
pKa (Strongest Basic)-4.9ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area86.99 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity53.48 m³·mol⁻¹ChemAxon
Polarizability20.31 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-03di-6039700000-818fd1c6815f0b1bf5f0Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-03dl-0910000000-edb7cb180844171b184bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0920000000-f564c4894586484f0dadSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0i03-0900000000-8d26ecd57affde1cd3bbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0fl1-4900000000-4aa5db44a21ab96fd092Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0390000000-aa1385fc637bcada69ebSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4l-0930000000-40d88bdfff342881e1e4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4m-2900000000-e755136e3280fcff165eSpectrum
Biological Properties
Cellular LocationsNot Available
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 IDFDB086352
KNApSAcK IDC00007336
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia Link5-Hydroxyferulic_acid
METLIN IDNot Available
PubChem Compound160594
PDB IDNot Available
ChEBI ID20582
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB ID
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Djoumbou Feunang, Yannick (2017). Cheminformatics Tools for Enabling Metabolomics, 2017 (PhD thesis). University of Alberta.

Enzymes

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
3-(3,4-dihydroxy-5-methoxyphenyl)prop-2-enoic acid → 6-[4-(2-carboxyeth-1-en-1-yl)-2-hydroxy-6-methoxyphenoxy]-3,4,5-trihydroxyoxane-2-carboxylic aciddetails
3-(3,4-dihydroxy-5-methoxyphenyl)prop-2-enoic acid → 6-[5-(2-carboxyeth-1-en-1-yl)-2-hydroxy-3-methoxyphenoxy]-3,4,5-trihydroxyoxane-2-carboxylic aciddetails
3-(3,4-dihydroxy-5-methoxyphenyl)prop-2-enoic acid → 6-{[3-(3,4-dihydroxy-5-methoxyphenyl)prop-2-enoyl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic aciddetails
General function:
sulfotransferase activity
Specific function:
Sulfotransferase that utilizes 3'-phospho-5'-adenylyl sulfate (PAPS) as sulfonate donor to catalyze the sulfate conjugation of phenolic monoamines (neurotransmitters such as dopamine, norepinephrine and serotonin) and phenolic and catechol drugs.
Gene Name:
SULT1A3
Uniprot ID:
P0DMM9
Molecular weight:
34195.96
Reactions
3-(3,4-dihydroxy-5-methoxyphenyl)prop-2-enoic acid → 3-[3-hydroxy-5-methoxy-4-(sulfooxy)phenyl]prop-2-enoic aciddetails