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cis-3-(3-Carboxyethenyl)-3,5-cyclohexadiene-1,2-diol (M2MDB000977)

Record Information
Version2.0
Creation Date2012-05-31 14:29:01 -0600
Update Date2015-06-03 17:19:22 -0600
Secondary Accession Numbers
  • ECMDB20129
Identification
Name:cis-3-(3-Carboxyethenyl)-3,5-cyclohexadiene-1,2-diol
DescriptionCis-3-(3-carboxyethenyl)-3,5-cyclohexadiene-1,2-diol belongs to the class of Unsaturated Fatty Acids. These are fatty acids whose chain contains at least one CC double bond. (inferred from compound structure)
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms:
  • (2E)-3-[(5R,6S)-5,6-dihydroxycyclohexa-1,3-dien-1-yl]prop-2-enoate
  • (2E)-3-[(5R,6S)-5,6-dihydroxycyclohexa-1,3-dien-1-yl]prop-2-enoate
  • (2E)-3-[(5R,6S)-5,6-dihydroxycyclohexa-1,3-dien-1-yl]prop-2-enoic acid
  • 3-(cis-5,6-dihydroxycyclohexa-1,3-dien-1-yl)prop-2-enoate
  • 3-(cis-5,6-Dihydroxycyclohexa-1,3-dien-1-yl)prop-2-enoate
  • 3-(cis-5,6-Dihydroxycyclohexa-1,3-dien-1-yl)prop-2-enoic acid
  • 3-[(5S,6R)-5,6-Dihydroxycyclohexa-1,3-dienyl]acrylate
  • 3-[(5S,6R)-5,6-Dihydroxycyclohexa-1,3-dienyl]acrylic acid
  • cis-3-(3-carboxyethenyl)-3,5-cyclohexadiene-1,2-diol
  • Cis-3-(3-carboxyethenyl)-3,5-cyclohexadiene-1,2-diol
Chemical Formula:C9H10O4
Weight:Average: 182.1733
Monoisotopic: 182.057908808
InChI Key:AEUBLTTWYCDTGM-HXOXMVQHSA-N
InChI:InChI=1S/C9H10O4/c10-7-3-1-2-6(9(7)13)4-5-8(11)12/h1-5,7,9-10,13H,(H,11,12)/b5-4+/t7-,9+/m0/s1
CAS number:Not Available
IUPAC Name:(2E)-3-[(5S,6R)-5,6-dihydroxycyclohexa-1,3-dien-1-yl]prop-2-enoic acid
Traditional IUPAC Name:(2E)-3-[(5S,6R)-5,6-dihydroxycyclohexa-1,3-dien-1-yl]prop-2-enoic acid
SMILES:[H]\C(=C(\[H])C1=CC=C[C@]([H])(O)[C@]1([H])O)C(O)=O
Chemical Taxonomy
Description belongs to the class of organic compounds known as 1,2-diols. These are polyols containing an alcohol group at two adjacent positions.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassAlcohols and polyols
Direct Parent1,2-diols
Alternative Parents
Substituents
  • Secondary alcohol
  • 1,2-diol
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxide
  • Hydrocarbon derivative
  • Carbonyl group
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External Descriptors
  • 3-[(5S,6R)-5,6-dihydroxycyclohexa-1,3-dienyl]acrylic acid (CHEBI:61462 )
Physical Properties
State:Not Available
Charge:-1
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility8.65 g/LALOGPS
logP0.22ALOGPS
logP-0.4ChemAxon
logS-1.3ALOGPS
pKa (Strongest Acidic)4.45ChemAxon
pKa (Strongest Basic)-3.3ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area77.76 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity48.8 m³·mol⁻¹ChemAxon
Polarizability17.71 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
trans-Cinnamic acid + Hydrogen ion + NADH + Oxygen > cis-3-(3-Carboxyethenyl)-3,5-cyclohexadiene-1,2-diol + NAD
cis-3-(3-Carboxyethenyl)-3,5-cyclohexadiene-1,2-diol + NAD > Trans-2,3-Dihydroxycinnamate + Hydrogen ion + NADH
trans-Cinnamic acid + Oxygen + NADH + Hydrogen ion <> cis-3-(3-Carboxyethenyl)-3,5-cyclohexadiene-1,2-diol + NAD
cis-3-(3-Carboxyethenyl)-3,5-cyclohexadiene-1,2-diol + NAD <> Trans-2,3-Dihydroxycinnamate + NADH + Hydrogen ion
cis-3-(3-Carboxyethenyl)-3,5-cyclohexadiene-1,2-diol + NAD > Trans-2,3-Dihydroxycinnamate + NADH
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
Cinnamic acid + NADH + Oxygen <> cis-3-(3-Carboxyethenyl)-3,5-cyclohexadiene-1,2-diol + NAD
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
SMPDB Pathways:
2-Oxopent-4-enoate metabolismPW001890 ThumbThumb?image type=greyscaleThumb?image type=simple
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 (TMS_1_1) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0900000000-26e5345d8825749c0023View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01bi-3900000000-0564d83ddf2238ad3e2bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0gbc-9200000000-62518c2e69f097044747View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0900000000-ccbff341ae73666fa73bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01qi-1900000000-5ccb9b79c971454d53e3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-06rf-7900000000-c29d91db275a61f25d16View 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
  • 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
  • Yurtsever D. (2007). Fatty acid methyl ester profiling of Enterococcus and Esherichia coli for microbial source tracking. M.sc. Thesis. Villanova University: U.S.A
Synthesis Reference:Not Available
Material Safety Data Sheet (MSDS)Not Available
External Links:
ResourceLink
CHEBI ID61462
HMDB IDNot Available
Pubchem Compound ID5282145
Kegg IDC12622
ChemSpider ID4445342
Wikipedia IDNot Available
BioCyc IDCPD-13034
EcoCyc IDCPD-13034

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. 3-phenylpropionate/cinnamic acid dioxygenase ferredoxin subunit
General function:
Involved in oxidoreductase activity
Specific function:
Part of the multicomponent 3-phenylpropionate dioxygenase, that converts 3-phenylpropionic acid (PP) and cinnamic acid (CI) into 3-phenylpropionate-dihydrodiol (PP- dihydrodiol) and cinnamic acid-dihydrodiol (CI-dihydrodiol), respectively. This protein seems to be a 2Fe-2S ferredoxin
Gene Name:
hcaC
Uniprot ID:
P0ABW0
Molecular weight:
11329
Protein Details
3. 3-phenylpropionate/cinnamic acid dioxygenase ferredoxin--NAD(+) reductase component
General function:
Involved in oxidoreductase activity
Specific function:
Part of the multicomponent 3-phenylpropionate dioxygenase, that converts 3-phenylpropionic acid (PP) and cinnamic acid (CI) into 3-phenylpropionate-dihydrodiol (PP- dihydrodiol) and cinnamic acid-dihydrodiol (CI-dihydrodiol), respectively
Gene Name:
hcaD
Uniprot ID:
P77650
Molecular weight:
43978
Reactions
Reduced ferredoxin + NAD(+) = oxidized ferredoxin + NADH.
Protein Details
4. 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
5. 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.