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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 20:28:54 UTC
Update Date2019-07-23 06:18:47 UTC
HMDB IDHMDB0035484
Secondary Accession Numbers
  • HMDB35484
Metabolite Identification
Common Name3-(3,4-Dihydroxy-5-methoxy)-2-propenoic acid
Description3-(3,4-Dihydroxy-5-methoxy)-2-propenoic acid is found in green vegetables. 3-(3,4-Dihydroxy-5-methoxy)-2-propenoic acid is isolated from bamboo (Phyllostachys edulis
Structure
Data?1563862727
Synonyms
ValueSource
3,4-Dihydroxy-5-methoxycinnamoic acidHMDB
3-(3,4-Dihydroxy-5-methoxy)-2-propenoic acid, 9ciHMDB
3-(3,4-Dihydroxy-5-methoxyphenyl)-2-propenoic acidHMDB
3-Methoxycaffeic acidHMDB
5-HydroxyferulateHMDB
5-Hydroxyferulic acidHMDB
HFLHMDB
Chemical FormulaC10H10O5
Average Molecular Weight210.1834
Monoisotopic Molecular Weight210.05282343
IUPAC Name(2E)-3-(3,4-dihydroxy-5-methoxyphenyl)prop-2-enoic acid
Traditional Name5-hydroxyferulate
CAS Registry Number1782-55-4
SMILES
COC1=CC(\C=C\C(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)/b3-2+
InChI KeyYFXWTVLDSKSYLW-NSCUHMNNSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as hydroxycinnamic acids. These 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

Route of exposure:

Source:

Biological location:

Role

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point182 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility1.04 g/LALOGPS
logP1.41ALOGPS
logP1.37ChemAxon
logS-2.3ALOGPS
pKa (Strongest Acidic)3.49ChemAxon
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
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, Positivesplash10-03dl-0910000000-edb7cb180844171b184bJSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-03di-6039700000-818fd1c6815f0b1bf5f0JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03dl-0970000000-6f1608973608646a6815JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-02tc-1910000000-99bedde5d4b95d2a72eaJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4s-3900000000-db5c30fefbe69f4bf23aJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0290000000-25c9e8b31be5cda28840JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-0950000000-6b6628733be09dd12decJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000g-2900000000-426d3db7318485c7e916JSpectraViewer | 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 IDFDB014170
KNApSAcK IDC00007336
Chemspider ID394087
KEGG Compound IDC05619
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound446834
PDB IDNot Available
ChEBI ID2069
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.. .