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Record Information
Version	2.0
Creation Date	2012-05-31 14:24:50 -0600
Update Date	2015-06-03 17:19:12 -0600
Secondary Accession Numbers	ECMDB20050
Identification
Name:	2-Succinyl-5-enolpyruvyl-6-hydroxy-3-cyclohexene-1-carboxylate
Description	2-succinyl-5-enolpyruvyl-6-hydroxy-3-cyclohexene-1-carboxylate is a member of the chemical class known as Tricarboxylic Acids and Derivatives. These are organic compounds containing three carboxylic acid groups (or salt/ester derivatives thereof).
Structure	MOLSDFPDBSMILESInChI × Structure for #<Compound:0xb116d058> Close
Synonyms:	2-Succinyl-5-enolpyruvyl-6-hydroxy-3-cyclohexene-1-carboxylic acid 5-Enolpyruvoyl-6-hydroxy-2-succinyl-cyclohex-3-ene-1-carboxylate 5-Enolpyruvoyl-6-hydroxy-2-succinyl-cyclohex-3-ene-1-carboxylic acid Sephchc
Chemical Formula:	C14H16O9
Weight:	Average: 328.2714 Monoisotopic: 328.07943211
InChI Key:	XYCATPIYKOARSZ-OAIFWDMCSA-N
InChI:	InChI=1S/C14H16O9/c1-6(13(19)20)23-9-4-2-7(8(15)3-5-10(16)17)11(12(9)18)14(21)22/h2,4,7,9,11-12,18H,1,3,5H2,(H,16,17)(H,19,20)(H,21,22)/t7-,9+,11-,12-/m1/s1
CAS number:	Not Available
IUPAC Name:	(1R,2S,5S,6S)-5-[(1-carboxyeth-1-en-1-yl)oxy]-2-(3-carboxypropanoyl)-6-hydroxycyclohex-3-ene-1-carboxylic acid
Traditional IUPAC Name:	sephchc
SMILES:	[H][C@@]1(O)[C@@]([H])(OC(=C)C(O)=O)C=C[C@]([H])(C(=O)CCC(O)=O)[C@@]1([H])C(O)=O
Chemical Taxonomy
Description	belongs to the class of organic compounds known as tricarboxylic acids and derivatives. These are carboxylic acids containing exactly three carboxyl groups.
Kingdom	Organic compounds
Super Class	Organic acids and derivatives
Class	Carboxylic acids and derivatives
Sub Class	Tricarboxylic acids and derivatives
Direct Parent	Tricarboxylic acids and derivatives
Alternative Parents	Gamma-keto acids and derivatives Beta hydroxy acids and derivatives Secondary alcohols Ketones Carboxylic acids Organic oxides Hydrocarbon derivatives
Substituents	Tricarboxylic acid or derivatives Gamma-keto acid Beta-hydroxy acid Keto acid Hydroxy acid Secondary alcohol Ketone Carboxylic acid Organic oxygen compound Organic oxide Hydrocarbon derivative Organooxygen compound Carbonyl group Alcohol Aliphatic homomonocyclic compound
Molecular Framework	Aliphatic homomonocyclic compounds
External Descriptors	tricarboxylic acid (CHEBI:50271 )
Physical Properties
State:	Not Available
Charge:	-3
Melting point:	Not Available
Experimental Properties:	Property Value Source
Predicted Properties	Property Value Source Water Solubility 4.52 g/L ALOGPS logP 0.24 ALOGPS logP -0.6 ChemAxon logS -1.9 ALOGPS pKa (Strongest Acidic) 3.19 ChemAxon pKa (Strongest Basic) -3.4 ChemAxon Physiological Charge -3 ChemAxon Hydrogen Acceptor Count 9 ChemAxon Hydrogen Donor Count 4 ChemAxon Polar Surface Area 158.43 Ų ChemAxon Rotatable Bond Count 8 ChemAxon Refractivity 74.12 m³·mol⁻¹ ChemAxon Polarizability 29.9 ų 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:	2-Succinyl-5-enolpyruvyl-6-hydroxy-3-cyclohexene-1-carboxylate <> (1R,6R)-6-Hydroxy-2-succinylcyclohexa-2,4-diene-1-carboxylate + Pyruvic acid alpha-Ketoglutarate + Hydrogen ion + Isochorismate <> 2-Succinyl-5-enolpyruvyl-6-hydroxy-3-cyclohexene-1-carboxylate + Carbon dioxide Isochorismate + alpha-Ketoglutarate <> 2-Succinyl-5-enolpyruvyl-6-hydroxy-3-cyclohexene-1-carboxylate + Carbon dioxide Hydrogen ion + Isochorismate + Oxoglutaric acid > 2-Succinyl-5-enolpyruvyl-6-hydroxy-3-cyclohexene-1-carboxylate + Carbon dioxide 2-Succinyl-5-enolpyruvyl-6-hydroxy-3-cyclohexene-1-carboxylate > (1R,6R)-6-Hydroxy-2-succinylcyclohexa-2,4-diene-1-carboxylate + Pyruvic acid Isochorismate + Oxoglutaric acid > 2-Succinyl-5-enolpyruvyl-6-hydroxy-3-cyclohexene-1-carboxylate + Carbon dioxide isochorismate + Oxoglutaric acid + Hydrogen ion + Isochorismate > Carbon dioxide + 2-Succinyl-5-enolpyruvyl-6-hydroxy-3-cyclohexene-1-carboxylate 2-Succinyl-5-enolpyruvyl-6-hydroxy-3-cyclohexene-1-carboxylate > (1R,6R)-6-hydroxy-2-succinylcyclohexa-2,4-diene-1-carboxylate + Pyruvic acid + (1R,6R)-6-Hydroxy-2-succinylcyclohexa-2,4-diene-1-carboxylate
SMPDB Pathways:	Menaquinol biosythesis PW001897
KEGG Pathways:	Metabolic pathways eco01100 Ubiquinone and other terpenoid-quinone biosynthesis ec00130
EcoCyc Pathways:	1,4-dihydroxy-2-naphthoate biosynthesis I PWY-5837
Concentrations
	Not Available
Spectra
Spectra:	Spectrum Type Description Splash Key Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TMS_3_13) - 70eV, Positive Not Available View in JSpectraViewer Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Positive splash10-03dl-0098000000-14bdaa9a9455fe4d407f View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Positive splash10-07bf-1091000000-cec52fd060868fa686ff View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Positive splash10-059i-7890000000-5f9e789819d019b75236 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Negative splash10-057i-2079000000-6c32ab6338bc028ff83a View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Negative splash10-0apr-2092000000-0748719002feb8fe53b1 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Negative splash10-01p9-9280000000-3fe98505389ab23310bb 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
Synthesis Reference:	Not Available
Material Safety Data Sheet (MSDS)	Not Available
Links
External Links:	Resource Link CHEBI ID 50271 HMDB ID Not Available Pubchem Compound ID 24883454 Kegg ID C16519 ChemSpider ID 21865723 Wikipedia ID Not Available BioCyc ID CPD-9924 EcoCyc ID CPD-9924

Enzymes