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Trans-2,3-Dihydroxycinnamate (M2MDB001043)

Record Information
Version2.0
Creation Date2012-05-31 14:32:38 -0600
Update Date2015-09-17 16:24:21 -0600
Secondary Accession Numbers
  • ECMDB20197
Identification
Name:Trans-2,3-Dihydroxycinnamate
DescriptionTrans-2,3-dihydroxycinnamate is a member of the chemical class known as Hydroxycinnamic Acid Derivatives. These are compounds containing an cinnamic acid derivative where the benzene ring is hydroxylated.
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms:
  • (2E)-3-(2,3-dihydroxyphenyl)prop-2-enoate
  • (2E)-3-(2,3-dihydroxyphenyl)acrylate
  • (2E)-3-(2,3-dihydroxyphenyl)acrylic acid
  • (2E)-3-(2,3-dihydroxyphenyl)prop-2-enoate
  • (2E)-3-(2,3-dihydroxyphenyl)prop-2-enoic acid
  • 2,3-Dihydroxy-trans-cinnamate
  • 2,3-Dihydroxy-trans-cinnamic acid
  • 2,3-Dihydroxycinnamate
  • 2,3-Dihydroxycinnamic acid
  • 3-(2,3-Dihydroxyphenyl)-2-Propenoate
  • 3-(2,3-Dihydroxyphenyl)-2-Propenoic acid
  • 3-(2,3-Dihydroxyphenyl)acrylate
  • 3-(2,3-Dihydroxyphenyl)acrylic acid
  • 3-(2,3-Dihydroxyphenyl)prop-2-enoate
  • 3-(2,3-Dihydroxyphenyl)prop-2-enoic acid
  • Trans-2,3-Dihydroxycinnamic acid
Chemical Formula:C9H8O4
Weight:Average: 180.1574
Monoisotopic: 180.042258744
InChI Key:SIUKXCMDYPYCLH-UHFFFAOYSA-N
InChI:InChI=1S/C9H8O4/c10-7-3-1-2-6(9(7)13)4-5-8(11)12/h1-5,10,13H,(H,11,12)
CAS number:31082-90-3
IUPAC Name:(2E)-3-(2,3-dihydroxyphenyl)prop-2-enoic acid
Traditional IUPAC Name:trans-2,3-dihydroxycinnamate
SMILES:OC(=O)C=CC1=C(O)C(O)=CC=C1
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
  • Coumaric acid or derivatives
  • Hydroxycinnamic acid
  • Catechol
  • Styrene
  • 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
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • 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 Solubility1.66 g/LALOGPS
logP1.66ALOGPS
logP1.53ChemAxon
logS-2ALOGPS
pKa (Strongest Acidic)3.67ChemAxon
pKa (Strongest Basic)-6.3ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area77.76 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity47.02 m³·mol⁻¹ChemAxon
Polarizability17.21 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 > Trans-2,3-Dihydroxycinnamate + Water + NAD
Trans-2,3-Dihydroxycinnamate + Oxygen > Hydrogen ion + 2-Hydroxy-6-ketononatrienedioate
cis-3-(3-Carboxyethenyl)-3,5-cyclohexadiene-1,2-diol + NAD > Trans-2,3-Dihydroxycinnamate + Hydrogen ion + NADH
cis-3-(3-Carboxyethenyl)-3,5-cyclohexadiene-1,2-diol + NAD <> Trans-2,3-Dihydroxycinnamate + NADH + Hydrogen ion
3-Hydroxycinnamic acid + Oxygen + NADH + Hydrogen ion <> Trans-2,3-Dihydroxycinnamate + Water + NAD
Trans-2,3-Dihydroxycinnamate + Oxygen <> 2-Hydroxy-6-ketononatrienedioate
cis-3-(3-Carboxyethenyl)-3,5-cyclohexadiene-1,2-diol + NAD > Trans-2,3-Dihydroxycinnamate + NADH
trans-Cinnamic acid + NADH + Oxygen > Trans-2,3-Dihydroxycinnamate + NAD
3-Hydroxycinnamic acid + NADH + Oxygen > Trans-2,3-Dihydroxycinnamate + Water + NAD
Trans-2,3-Dihydroxycinnamate + Oxygen > 2-Hydroxy-6-ketononatrienedioate
3-(3-Hydroxyphenyl)propanoic acid + NADH + Hydrogen ion + Oxygen + 3-Hydroxycinnamic acid <> 3-(2,3-Dihydroxyphenyl)propionic acid + Water + NAD + Trans-2,3-Dihydroxycinnamate
3-(2,3-Dihydroxyphenyl)propionic acid + Oxygen + Trans-2,3-Dihydroxycinnamate <> 2-Hydroxy-6-ketononadienedicarboxylate + 2-Hydroxy-6-ketononatrienedioate
NADH + Hydrogen ion + Oxygen + Hydrocinnamic acid <> cis-3-(Carboxy-ethyl)-3,5-cyclo-hexadiene-1,2-diol + NAD + Trans-2,3-Dihydroxycinnamate
cis-3-(Carboxy-ethyl)-3,5-cyclo-hexadiene-1,2-diol + NAD + cis-3-(3-Carboxyethenyl)-3,5-cyclohexadiene-1,2-diol <> 3-(2,3-Dihydroxyphenyl)propionic acid + NADH + Hydrogen ion + Trans-2,3-Dihydroxycinnamate
SMPDB Pathways:
Phenylalanine metabolismPW000921 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways:
  • Microbial metabolism in diverse environments ec01120
  • Phenylalanine metabolism ec00360
EcoCyc Pathways:
  • cinnamate and 3-hydroxycinnamate degradation to 2-oxopent-4-enoate PWY-6690
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-00e9-5149000000-c43f9e3eea6dc7cf478fView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-01qi-1900000000-50cbd59f3add6f75304eView 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, Positivesplash10-01q9-0900000000-98aa50e6e9bf94a15e97View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01q0-1900000000-6c0321e0be42f1c0d8cfView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004i-9600000000-159d189c7ec4cba02568View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0900000000-26db0d20f46a97dc9315View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-0900000000-c444f8d8101c35e6ffe0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-4900000000-7ae416ed952d0efb152cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01q9-0900000000-50d20b5f719c942007ceView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00ri-0900000000-6ad36236445f0071fd66View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0kd0-9500000000-275e53c97be478ed2916View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-002r-0900000000-a54c94dd8b9d66011f76View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0900000000-a896ae42cec38ed3ac3eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001i-3900000000-fd7059f1532edf5f80b7View in MoNA
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
  • Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882
Synthesis Reference:Not Available
Material Safety Data Sheet (MSDS)Not Available
External Links:
ResourceLink
CHEBI ID32356
HMDB IDHMDB0140954
Pubchem Compound ID5282146
Kegg IDC12623
ChemSpider ID4445343
Wikipedia ID2,3-Dihydroxycinnamic acid
BioCyc IDCPD-10796
EcoCyc IDCPD-10796

Enzymes

Protein Details
1. 3-phenylpropionate/cinnamic acid dioxygenase subunit alpha
General function:
Involved in iron ion binding
Specific function:
Part of the multicomponent 3-phenylpropionate dioxygenase. Converts 3-phenylpropionic acid (PP) and cinnamic acid (CI) into 3-phenylpropionate-dihydrodiol (PP-dihydrodiol) and cinnamic acid-dihydrodiol (CI-dihydrodiol), respectively
Gene Name:
hcaE
Uniprot ID:
P0ABR5
Molecular weight:
51109
Reactions
3-phenylpropanoate + NADH + O(2) = 3-(cis-5,6-dihydroxycyclohexa-1,3-dien-1-yl)propanoate + NAD(+).
(2E)-3-phenylprop-2-enoate + NADH + O(2) = (2E)-3-(2,3-dihydroxyphenyl)prop-2-enoate + NAD(+).
Protein Details
2. 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
3. 3-phenylpropionate/cinnamic acid dioxygenase subunit beta
General function:
Involved in 3-phenylpropionate dioxygenase activity
Specific function:
Part of the multicomponent 3-phenylpropionate dioxygenase. Converts 3-phenylpropionic acid (PP) and cinnamic acid (CI) into 3-phenylpropionate-dihydrodiol (PP-dihydrodiol) and cinnamic acid-dihydrodiol (CI-dihydrodiol), respectively
Gene Name:
hcaF
Uniprot ID:
Q47140
Molecular weight:
20579
Reactions
3-phenylpropanoate + NADH + O(2) = 3-(cis-5,6-dihydroxycyclohexa-1,3-dien-1-yl)propanoate + NAD(+).
(2E)-3-phenylprop-2-enoate + NADH + O(2) = (2E)-3-(2,3-dihydroxyphenyl)prop-2-enoate + NAD(+).
Protein Details
4. 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
5. 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(+).