ECMDB: cis-3-(3-Carboxyethenyl)-3,5-cyclohexadiene-1,2-diol (ECMDB20129) (M2MDB000977)

Identification Taxonomy Physical Properties Biological Properties Spectra Concentrations Links References Enzymes (5)XML

Proteins (226)

Record Information

Version

2.0

Creation Date

2012-05-31 14:29:01 -0600

Update Date

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

Secondary Accession Numbers

ECMDB20129

Identification

Name:

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

Description

Cis-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

MOL SDF PDB SMILES InChI

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.

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-[(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:

Property	Value	Source

Predicted Properties

Property	Value	Source
Water Solubility	8.65 g/L	ALOGPS
logP	0.22	ALOGPS
logP	-0.4	ChemAxon
logS	-1.3	ALOGPS
pKa (Strongest Acidic)	4.45	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	2	ChemAxon
Refractivity	48.8 m³·mol⁻¹	ChemAxon
Polarizability	17.71 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:

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 metabolism	PW001890
Phenylalanine metabolism	PW000921

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 Type	Description	Splash Key
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001i-0900000000-ccbff341ae73666fa73b	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-01qi-1900000000-5ccb9b79c971454d53e3	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-06rf-7900000000-c29d91db275a61f25d16	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014i-0900000000-26e5345d8825749c0023	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-01bi-3900000000-0564d83ddf2238ad3e2b	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0gbc-9200000000-62518c2e69f097044747	View in MoNA
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
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	61462
HMDB ID	Not Available
Pubchem Compound ID	5282145
Kegg ID	C12622
ChemSpider ID	4445342
Wikipedia ID	Not Available
BioCyc ID	CPD-13034
EcoCyc ID	CPD-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.

cis-3-(3-Carboxyethenyl)-3,5-cyclohexadiene-1,2-diol (ECMDB20129) (M2MDB000977)

Structure for #<Compound:0xa8ed73dc>

Enzymes

Reactions

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