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3-(2,3-Dihydroxyphenyl)propanoate (M2MDB000913)

Record Information
Version2.0
Creation Date2012-05-31 14:25:34 -0600
Update Date2015-06-03 17:19:14 -0600
Secondary Accession Numbers
  • ECMDB20064
Identification
Name:3-(2,3-Dihydroxyphenyl)propanoate
Description3-(2,3-dihydroxyphenyl)propanoate is a member of the chemical class known as Catechols. These are compounds containing a 1,2-benzenediol moeity. 3-(2,3-dihydroxyphenyl)propanoate is invovled in Phenylpropionic acid degradation. The compound 3-(2,3-dihydroxyphenyl)propionate (DHPP) is a common intermediate of both pathways which must be cleaved by the MhpB dioxygenase before entering into the primary cell metabolism. (PMID 19520845)
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms:
  • (3R)-3-(2,4-dimethoxyphenyl)chroman-7-ol
  • 2,3-Dhppa
  • 2,3-DIHYDROXY-b-phenylproprionate
  • 2,3-DIHYDROXY-B-PHENYLPROPRIONIC ACID
  • 2,3-Dihydroxy-Benzenepropanoate
  • 2,3-Dihydroxy-Benzenepropanoic acid
  • 2,3-Dihydroxyphenylpropanoate
  • 2,3-Dihydroxyphenylpropanoic acid
  • 2,3-Dihydroxyphenylpropionate
  • 2,3-Dihydroxyphenylpropionic acid
  • 2-3-DIHYDROXYPHENYL-PROPIONATE
  • 2-3-DIHYDROXYPHENYL-propionic acid
  • 3,4-Dihydroxy-Benzenepropanoate
  • 3,4-Dihydroxy-Benzenepropanoic acid
  • 3,4-Dihydroxy-Hydrocinnamate
  • 3,4-Dihydroxy-Hydrocinnamic acid
  • 3,4-Dihydroxybenzenepropanoate
  • 3,4-Dihydroxybenzenepropanoic acid
  • 3,4-Dihydroxyhydrocinnamate
  • 3,4-Dihydroxyhydrocinnamic acid
  • 3,4-Dihydroxyphenylpropionate
  • 3,4-Dihydroxyphenylpropionic acid
  • 3-(2,3-Dihydroxyphenyl)propanoate
  • 3-(2,3-Dihydroxyphenyl)propanoic acid
  • 3-(2,3-Dihydroxyphenyl)propionate
  • 3-(2,3-Dihydroxyphenyl)propionic acid
  • 3-(3,4-Dihydroxyphenyl)propionate
  • 3-(3,4-Dihydroxyphenyl)propionic acid
  • Benzenepropanoate, 3,4-dihydroxy- (9CI)
  • Benzenepropanoic acid, 3,4-dihydroxy- (9CI)
  • Dihydrocaffeate
  • Dihydrocaffeic acid
  • Hydrocaffeate
  • Hydrocaffeic acid
Chemical Formula:C9H10O4
Weight:Average: 182.1733
Monoisotopic: 182.057908808
InChI Key:QZDSXQJWBGMRLU-UHFFFAOYSA-N
InChI:InChI=1S/C9H10O4/c10-7-3-1-2-6(9(7)13)4-5-8(11)12/h1-3,10,13H,4-5H2,(H,11,12)
CAS number:3714-73-6
IUPAC Name:3-(2,3-dihydroxyphenyl)propanoic acid
Traditional IUPAC Name:2,3-dhppa
SMILES:OC(=O)CCC1=C(O)C(O)=CC=C1
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
Physical Properties
State:Not Available
Charge:-1
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility3.02 g/LALOGPS
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
Polarizability17.68 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
cis-3-(Carboxy-ethyl)-3,5-cyclo-hexadiene-1,2-diol + NAD > 3-(2,3-Dihydroxyphenyl)propanoate + NADH
3-(3-Hydroxyphenyl)propanoic acid + NADH + Oxygen > 3-(2,3-Dihydroxyphenyl)propanoate + Water + NAD
3-(2,3-Dihydroxyphenyl)propanoate + Oxygen > 2-Hydroxy-6-oxonona-2,4-diene-1,9-dioate
SMPDB Pathways:
Phenylalanine metabolismPW000921 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways:
  • Microbial metabolism in diverse environments ec01120
  • Phenylalanine metabolism ec00360
EcoCyc Pathways:Not Available
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-00ai-8169000000-57d099213b80f74754f0View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00dr-0900000000-42307d872084e0a43967View 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, Positivesplash10-014i-0900000000-843dd549d47692169f19View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00ri-1900000000-4c55ee3c98ded47a7c93View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004i-9400000000-715c4800f53e00770beaView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0900000000-b898849ef0adfdcc8ba6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01qi-1900000000-d3f406f1106a548a81a4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9700000000-06658447e99ab7e422b5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0900000000-d450fceaa753730689bcView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0bu9-0900000000-dd7ac8bdd1c9a01f90a2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-05no-6900000000-2004de093c4ed2588082View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0900000000-85d7a58f912ce2360f62View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0abj-5900000000-afd351c121906895b1a4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0fsa-9200000000-3e44754ea683742401acView 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:
  • Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
  • Manso, I., Torres, B., Andreu, J. M., Menendez, M., Rivas, G., Alfonso, C., Diaz, E., Garcia, J. L., Galan, B. (2009). "3-Hydroxyphenylpropionate and phenylpropionate are synergistic activators of the MhpR transcriptional regulator from Escherichia coli." J Biol Chem 284:21218-21228. Pubmed: 19520845
Synthesis Reference:Not Available
Material Safety Data Sheet (MSDS)Not Available
External Links:
ResourceLink
CHEBI ID18136
HMDB IDHMDB0134042
Pubchem Compound ID20
Kegg IDC04044
ChemSpider ID19
Wikipedia IDNot Available
BioCyc IDCPD-9367
EcoCyc IDCPD-9367

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(+).