Showing metabocard for 3,4-Dihydroxyhydrocinnamic acid (BMDB0000423)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-09-30 22:30:29 UTC
Update Date2020-04-22 15:03:31 UTC
BMDB IDBMDB0000423
Secondary Accession Numbers
  • BMDB00423
Metabolite Identification
Common Name3,4-Dihydroxyhydrocinnamic acid
Description3,4-Dihydroxyhydrocinnamic acid, also known as 3,4-dihydroxy-b-phenylpropionate or dihydrocaffeic 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. 3,4-Dihydroxyhydrocinnamic acid is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
3,4-Dihydroxy-beta-phenylpropionic acidChEBI
3,4-Dihydroxybenzenepropionic acidChEBI
3,4-Dihydroxydihydrocinnamic acidChEBI
3,4-Dihydroxyphenylpropionic acidChEBI
3-(3,4-Dihydroxyphenyl)propanoateKegg
3,4-Dihydroxy-b-phenylpropionateGenerator
3,4-Dihydroxy-b-phenylpropionic acidGenerator
3,4-Dihydroxy-beta-phenylpropionateGenerator
3,4-Dihydroxy-β-phenylpropionateGenerator
3,4-Dihydroxy-β-phenylpropionic acidGenerator
3,4-DihydroxybenzenepropanoateGenerator
3,4-DihydroxybenzenepropionateGenerator
3,4-DihydroxydihydrocinnamateGenerator
3,4-DihydroxyphenylpropionateGenerator
3-(3,4-Dihydroxyphenyl)propionateGenerator
DihydrocaffeateGenerator
HydrocaffeateGenerator
3-(3,4-Dihydroxyphenyl)propanoic acidGenerator
3,4-DihydroxyhydrocinnamateGenerator
3,4-Dihydroxy-(6ci,7ci,8ci)hydrocinnamateHMDB
3,4-Dihydroxy-(6ci,7ci,8ci)hydrocinnamic acidHMDB
3,4-Dihydroxyphenylpropionic acid, potassium saltHMDB
DHCHMDB
3,4-Dihydroxyhydrocinnamic acidHMDB
3-(3',4'-Dihydroxyphenyl)propanoic acidHMDB
Chemical FormulaC9H10O4
Average Molecular Weight182.1733
Monoisotopic Molecular Weight182.057908808
IUPAC Name3-(3,4-dihydroxyphenyl)propanoic acid
Traditional Namedihydrocaffeic acid
CAS Registry Number1078-61-1
SMILES
OC(=O)CCC1=CC(O)=C(O)C=C1
InChI Identifier
InChI=1S/C9H10O4/c10-7-3-1-6(5-8(7)11)2-4-9(12)13/h1,3,5,10-11H,2,4H2,(H,12,13)
InChI KeyDZAUWHJDUNRCTF-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
  • Catechol
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Monocyclic benzene moiety
  • Benzenoid
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Organic oxide
  • Organic oxygen compound
  • Carbonyl group
  • Organooxygen compound
  • Hydrocarbon derivative
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
StatusExpected but not Quantified
Origin
  • Exogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cytoplasm
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point136 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility428 mg/mLNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP1.04ALOGPS
logP1.45ChemAxon
logS-1.8ALOGPS
pKa (Strongest Acidic)3.84ChemAxon
pKa (Strongest Basic)-6.3ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area77.76 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity45.93 m³·mol⁻¹ChemAxon
Polarizability17.85 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
HMDB IDHMDB0000423
DrugBank IDNot Available
Phenol Explorer Compound ID579
FooDB IDFDB008857
KNApSAcK IDC00002735
Chemspider ID308986
KEGG Compound IDC10447
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID5412
PubChem Compound348154
PDB IDNot Available
ChEBI ID48400
References
Synthesis ReferenceSabally Kebba; Karboune Salwa; St-Louis Richard; Kermasha Selim Lipase-catalyzed transesterification of dihydrocaffeic acid with flaxseed oil for the synthesis of phenolic lipids. Journal of biotechnology (2006), 127(1), 167-76.
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available