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Record Information

Version

2.0

Creation Date

2012-05-31 14:29:05 -0600

Update Date

2015-06-03 17:19:22 -0600

Secondary Accession Numbers

ECMDB20130

Identification

Name:

cis-3-(Carboxy-ethyl)-3,5-cyclo-hexadiene-1,2-diol

Description

Cis-3-(carboxy-ethyl)-3,5-cyclo-hexadiene-1,2-diol (also known as 3-(cis-5,6-Dihydroxycyclohexa-1,3-dien-1-yl)propanoate) is an intermediate invovled in Phenylpropionic acid degradation. It is a substrate for the enzyme 3-phenylpropionate-dihydrodiol/cinnamic acid-dihydrodiol dehydrogenase (hcaB). This enzyme normally 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. Cis-3-(carboxy-ethyl)-3,5-cyclo-hexadiene-1,2-diol is also a substrate for 3-phenylpropionate/cinnamic acid dioxygenase (hcaE and hcaF), which is also part of the phentylpropionic acid degradatioin pathway. This enzyme catalyzes the reaction 3-phenylpropanoate + NADH + O2 = 3-(cis-5,6-dihydroxycyclohexa-1,3-dien-1-yl)propanoate + NAD+

Structure

MOL SDF PDB SMILES InChI

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
3-[(5S,6R)-5,6-Dihydroxycyclohexa-1,3-dienyl]propanoate
3-[(5S,6R)-5,6-Dihydroxycyclohexa-1,3-dienyl]propanoic acid
cis-3-(3-carboxyethyl)-3,5-cyclohexadiene-1,2-diol
cis-3-(carboxyethyl)-3,5-cyclohexadiene-1,2-diol
Cis-3-(2-Carboxy-ethyl)-3,5-cyclo-hexadiene-1,2-diol
Cis-3-(2-Carboxyethyl)-3,5-cyclohexadiene-1,2-diol
Cis-3-(3-Carboxyethyl)-3,5-cyclohexadiene-1,2-diol
Cis-3-(Carboxyethyl)-3,5-cyclohexadiene-1,2-diol

Chemical Formula:

C₉H₁₂O₄

Weight:

Average: 184.1892
Monoisotopic: 184.073558872

InChI Key:

RKDFGWAXBBGKMR-IONNQARKSA-N

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)/t7-,9+/m0/s1

CAS number:

Not Available

IUPAC Name:

3-[(5S,6R)-5,6-dihydroxycyclohexa-1,3-dien-1-yl]propanoic acid

Traditional IUPAC Name:

3-[(5S,6R)-5,6-dihydroxycyclohexa-1,3-dien-1-yl]propanoic acid

SMILES:

[H][C@]1(O)C=CC=C(CCC(O)=O)[C@@]1([H])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.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Alcohols and polyols

Direct Parent

1,2-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 Framework

Aliphatic homomonocyclic compounds

External Descriptors

3-(cis-5,6-dihydroxycyclohexa-1,3-dienyl)propanoic acid (CHEBI:10472 )

Physical Properties

State:

Not Available

Charge:

-1

Melting point:

Not Available

Experimental Properties:

Property	Value	Source

Predicted Properties

Property	Value	Source
Water Solubility	33.6 g/L	ALOGPS
logP	-0.14	ALOGPS
logP	-0.39	ChemAxon
logS	-0.74	ALOGPS
pKa (Strongest Acidic)	4.38	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	77.76 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	47.71 m³·mol⁻¹	ChemAxon
Polarizability	18.16 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Biological Properties

Cellular Locations:

Cytoplasm

Reactions:

SMPDB Pathways:

Phenylalanine metabolism

PW000921

KEGG Pathways:

Microbial metabolism in diverse environments ec01120
Phenylalanine metabolism ec00360

EcoCyc Pathways:

3-phenylpropionate and 3-(3-hydroxyphenyl)propionate degradation to 2-oxopent-4-enoate HCAMHPDEG-PWY

Concentrations

Not Available

Spectra

Spectra:

Spectrum Type	Description	Splash Key
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014r-0900000000-68e07151df852738f9c0	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00kr-4900000000-6bb5856c535dd23ee710	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0uxu-9100000000-4798b393b5e44011fe0d	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001i-0900000000-61f1547e06b25af272ec	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00m0-1900000000-0f21a3ab1b243d30eef8	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4l-9600000000-2bf48d77b8e2205957d6	View in MoNA
MS	Mass Spectrum (Electron Ionization)	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View 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
Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948. Pubmed: 18331064
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

Links

External Links:

Resource	Link
CHEBI ID	10472
HMDB ID	Not Available
Pubchem Compound ID	443290
Kegg ID	C11588
ChemSpider ID	391536
Wikipedia ID	Not Available
BioCyc ID	CARBOXYETHYL-3-5-CYCLOHEXADIENE-1-2-DIOL
EcoCyc ID	CARBOXYETHYL-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.

Structural search and advanced query search is temporarily unavailable. We are working to fix this issue. Thank you for your support and patience.

cis-3-(Carboxy-ethyl)-3,5-cyclo-hexadiene-1,2-diol (M2MDB000978)

Structure for #<Compound:0xaada2f00>

Enzymes

Reactions

Reactions

Reactions

Reactions