2-Hydroxy-3-(4-hydroxyphenyl)propenoic acid (ECMDB24915) (M2MDB007032)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes (3)XML
Proteins (3)
Record Information
Version2.0
Creation Date2015-09-18 17:30:02 -0600
Update Date2015-09-18 17:30:02 -0600
Secondary Accession Numbers
  • ECMDB24915
Identification
Name:2-Hydroxy-3-(4-hydroxyphenyl)propenoic acid
Description
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms:
ValueSource
4,alpha-Dihydroxycinnamic acidChEBI
4-Hydroxy-enol-phenylpyruvateKegg
4,a-DihydroxycinnamateGenerator
4,a-Dihydroxycinnamic acidGenerator
4,alpha-DihydroxycinnamateGenerator
4,Α-dihydroxycinnamateGenerator
4,Α-dihydroxycinnamic acidGenerator
4-Hydroxy-enol-phenylpyruvic acidGenerator
2-Hydroxy-3-(4-hydroxyphenyl)propenoateGenerator
Chemical Formula:C9H8O4
Weight:Average: 180.1574
Monoisotopic: 180.042258744
InChI Key:GQYBCIHRWMPOOF-YVMONPNESA-N
InChI:InChI=1S/C9H8O4/c10-7-3-1-6(2-4-7)5-8(11)9(12)13/h1-5,10-11H,(H,12,13)/b8-5-
CAS number:Not Available
IUPAC Name:(2Z)-2-hydroxy-3-(4-hydroxyphenyl)prop-2-enoic acid
Traditional IUPAC Name:4,α-dihydroxycinnamic acid
SMILES:OC(=O)C(\O)=C\C1=CC=C(O)C=C1
Chemical Taxonomy
Description belongs to the class of organic compounds known as phenylpyruvic acid derivatives. Phenylpyruvic acid derivatives are compounds containing a phenylpyruvic acid moiety, which consists of a phenyl group substituted at the second position by an pyruvic acid.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassPhenylpyruvic acid derivatives
Direct ParentPhenylpyruvic acid derivatives
Alternative Parents
Substituents
  • Cinnamic acid
  • Cinnamic acid or derivatives
  • Coumaric acid
  • Coumaric acid or derivatives
  • Hydroxycinnamic acid
  • Hydroxycinnamic acid or derivatives
  • Enol-phenylpyruvate
  • Phenol
  • 1-hydroxy-2-unsubstituted benzenoid
  • Monocarboxylic acid or derivatives
  • Enol
  • Carboxylic acid
  • Carboxylic acid derivative
  • Carbonyl group
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Physical Properties
State:Not Available
Charge:-1
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility0.81 g/LALOGPS
logP1.28ALOGPS
logP1.31ChemAxon
logS-2.4ALOGPS
pKa (Strongest Acidic)3.16ChemAxon
pKa (Strongest Basic)-6ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area77.76 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity47.01 m³·mol⁻¹ChemAxon
Polarizability17.25 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
3-Hydroxycinnamic acid + Hydrogen ion + NADH + Oxygen > NAD + Water + 2-Hydroxy-3-(4-hydroxyphenyl)propenoic acid + 2-Hydroxy-3-(4-hydroxyphenyl)propenoic acid
NAD + cis-3-(3-Carboxyethenyl)-3,5-cyclohexadiene-1,2-diol > NADH + Hydrogen ion + 2-Hydroxy-3-(4-hydroxyphenyl)propenoic acid + 2-Hydroxy-3-(4-hydroxyphenyl)propenoic acid
2-Hydroxy-3-(4-hydroxyphenyl)propenoic acid + Oxygen + 2-Hydroxy-3-(4-hydroxyphenyl)propenoic acid > Hydrogen ion + 2-Hydroxy-6-ketononatrienedioate
Cis-3-(3-carboxyethyl)-3,5-cyclohexadiene-1,2-diol + NAD > 2-Hydroxy-3-(4-hydroxyphenyl)propenoic acid + NADH + Hydrogen ion
SMPDB Pathways:
2-Oxopent-4-enoate metabolismPW001890 ThumbThumb?image type=greyscaleThumb?image type=simple
2-Oxopent-4-enoate metabolism 2PW002035 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways:Not Available
EcoCyc Pathways:Not Available
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-053r-1900000000-10c51d0329cb2a35dbb8View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-00gi-6259000000-cdf2744454615081e02fView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0bu0-0900000000-a08730e02c84f43e7926View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-0900000000-2eb4f2eaa5d547249a3eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a6r-7900000000-63f2942443ac7bfdce48View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0900000000-8576bdecf0b58e989df6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-0900000000-46e515a63da5ddf92de9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-0900000000-3c0a27f480b5bb59093cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0900000000-02f0fa9241cf4b1591c7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-9800000000-0e7b12140d77aa62a512View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0api-4900000000-6f21f2ecdec85109e7d5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01qi-0900000000-28cf4812bb35ce056a15View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4r-1900000000-bd40f97e341181046c0fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004i-9200000000-c7f40face58730829b4aView in MoNA
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
References
References:Not Available
Synthesis Reference:Not Available
Material Safety Data Sheet (MSDS)Not Available
External Links:
ResourceLink
CHEBI ID27683
HMDB IDHMDB0006915
Pubchem Compound ID636708
Kegg IDC05350
ChemSpider ID552441
Wikipedia IDNot Available
BioCyc IDNot Available

Enzymes

Protein Details
1. 2,3-dihydroxyphenylpropionate/2,3-dihydroxicinnamic acid 1,2-dioxygenase
General function:
Involved in iron ion binding
Specific function:
Catalyzes the non-heme iron(II)-dependent oxidative cleavage of 2,3-dihydroxyphenylpropionic acid and 2,3- dihydroxicinnamic acid into 2-hydroxy-6-ketononadienedioate and 2- hydroxy-6-ketononatrienedioate, respectively
Gene Name:
mhpB
Uniprot ID:
P0ABR9
Molecular weight:
34196
Reactions
3-(2,3-dihydroxyphenyl)propanoate + O(2) = 2-hydroxy-6-oxonona-2,4-diene-1,9-dioate.
(2E)-3-(2,3-dihydroxyphenyl)prop-2-enoate + O(2) = 2-hydroxy-6-oxonona-2,4,7-triene-1,9-dioate.
Protein Details
2. 3-phenylpropionate-dihydrodiol/cinnamic acid-dihydrodiol dehydrogenase
General function:
Not Available
Specific function:
Converts 3-phenylpropionate-dihydrodiol (PP-dihydrodiol) and cinnamic acid-dihydrodiol (CI-dihydrodiol) into 3-(2,3-dihydroxylphenyl)propanoic acid (DHPP) and 2,3-dihydroxicinnamic acid (DHCI), respectively (By similarity). Converts 3-phenylpropionate-dihydrodiol (PP-dihydrodiol) and cinnamic acid-dihydrodiol (CI-dihydrodiol) into 3-(2,3-dihydroxylphenyl)propanoic acid (DHPP) and 2,3-dihydroxicinnamic acid (DHCI), respectively (By similarity).
Gene Name:
hcaB
Uniprot ID:
P0CI31
Molecular weight:
Not Available
Reactions
3-(cis-5,6-dihydroxycyclohexa-1,3-dien-1-yl)propanoate + NAD(+) = 3-(2,3-dihydroxyphenyl)propanoate + NADH.
3-(cis-5,6-dihydroxycyclohexa-1,3-dien-1-yl)propanoate + NAD(+) = 3-(2,3-dihydroxyphenyl)propanoate + NADH.
(2E)-3-(cis-5,6-dihydroxycyclohexa-1,3-dien-1-yl)prop-2-enoate + NAD(+) = (2E)-3-(2,3-dihydroxyphenyl)prop-2-enoate + NADH.
Protein Details
3. 3-(3-hydroxy-phenyl)propionate/3-hydroxycinnamic acid hydroxylase
General function:
Involved in 3-(3-hydroxyphenyl)propionate hydroxylase activity
Specific function:
Catalyzes the insertion of one atom of molecular oxygen into position 2 of the phenyl ring of 3-(3- hydroxyphenyl)propionate (3-HPP) and hydroxycinnamic acid (3HCI)
Gene Name:
mhpA
Uniprot ID:
P77397
Molecular weight:
62185
Reactions
3-(3-hydroxyphenyl)propanoate + NADH + O(2) = 3-(2,3-dihydroxyphenyl)propanoate + H(2)O + NAD(+).
(2E)-3-(3-hydroxyphenyl)prop-2-enoate + NADH + O(2) = (2E)-3-(2,3-dihydroxyphenyl)prop-2-enoate + H(2)O + NAD(+).