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Cis-3-(3-carboxyethyl)-3,5-cyclohexadiene-1,2-diol (M2MDB001722)

Record Information
Version2.0
Creation Date2012-07-30 14:55:17 -0600
Update Date2015-06-03 17:21:09 -0600
Secondary Accession Numbers
  • ECMDB21320
Identification
Name:Cis-3-(3-carboxyethyl)-3,5-cyclohexadiene-1,2-diol
DescriptionCis-3-(3-carboxyethyl)-3,5-cyclohexadiene-1,2-diol is a member of the chemical class known as Cyclic Alcohols and Derivatives. These are organic compounds containing an aliphatic ring substituted with at least one hydroxyl group. Cis-3-(3-carboxyethyl)-3,5-cyclohexadiene-1,2-diol is invovled in Phenylpropionic acid degradation. r 15;80(8):2939-48.)
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms:
  • 3-(cis-5,6-dihydroxycyclohexa-1,3-dien-1-yl)propanoate
  • 3-(cis-5,6-Dihydroxycyclohexa-1,3-dien-1-yl)propanoate
  • 3-(cis-5,6-Dihydroxycyclohexa-1,3-dien-1-yl)propanoic acid
  • cis-3-(3-carboxyethyl)-3,5-cyclohexadiene-1,2-diol
  • cis-3-(carboxyethyl)-3,5-cyclohexadiene-1,2-diol
  • Cis-3-(Carboxyethyl)-3,5-cyclohexadiene-1,2-diol
Chemical Formula:C9H11O4
Weight:Average: 183.1812
Monoisotopic: 183.06573384
InChI Key:RKDFGWAXBBGKMR-APPZFPTMSA-M
InChI:InChI=1S/C9H12O4/c10-7-3-1-2-6(9(7)13)4-5-8(11)12/h1-3,7,9-10,13H,4-5H2,(H,11,12)/p-1/t7-,9+/m1/s1
CAS number:Not Available
IUPAC Name:3-[(5R,6S)-5,6-dihydroxycyclohexa-1,3-dien-1-yl]propanoate
Traditional IUPAC Name:3-[(5R,6S)-5,6-dihydroxycyclohexa-1,3-dien-1-yl]propanoate
SMILES:[H]O[C@]1([H])C([H])=C([H])C([H])=C(C([H])([H])C([H])([H])C([O-])=O)[C@]1([H])O[H]
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
  • Organic anion
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External Descriptors
Physical Properties
State:Not Available
Charge:-1
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility110 g/LALOGPS
logP0.11ALOGPS
logP-0.39ChemAxon
logS-0.26ALOGPS
pKa (Strongest Acidic)4.38ChemAxon
pKa (Strongest Basic)-3.3ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area80.59 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity58.55 m³·mol⁻¹ChemAxon
Polarizability17.77 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
Hydrogen ion + NADH + Oxygen + Hydrocinnamic acid > Cis-3-(3-carboxyethyl)-3,5-cyclohexadiene-1,2-diol + NAD
Cis-3-(3-carboxyethyl)-3,5-cyclohexadiene-1,2-diol + NAD > 3-(2,3-Dihydroxyphenyl)propionic acid + Hydrogen ion + NADH
NADH + Oxygen + 3-phenylpropanoate <> NAD + Cis-3-(3-carboxyethyl)-3,5-cyclohexadiene-1,2-diol
trans-Cinnamic acid + Hydrogen ion + Oxygen + NADH > Cis-3-(3-carboxyethyl)-3,5-cyclohexadiene-1,2-diol + NAD
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 metabolism 2PW002035 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways:Not Available
EcoCyc Pathways:
  • 3-phenylpropionate and 3-(3-hydroxyphenyl)propionate degradation to 2-oxopent-4-enoate HCAMHPDEG-PWY
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0900000000-cc2c9931c60d508f8019View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00e9-2900000000-cf8bb3986b08d1ccb57cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9100000000-e271782d2112ea3e2d7bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0900000000-c741fa27abb7d9fb835eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-1900000000-a367f068c9ccca892187View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-6900000000-e50087b55d65486dac49View in MoNA
References
References:
  • 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 ID60087
HMDB IDNot Available
Pubchem Compound ID9543127
Kegg IDC11588
ChemSpider ID7822100
Wikipedia IDNot Available
BioCyc IDCARBOXYETHYL-3-5-CYCLOHEXADIENE-1-2-DIOL
EcoCyc IDCARBOXYETHYL-3-5-CYCLOHEXADIENE-1-2-DIOL

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.