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Record Information
Version	2.0
Creation Date	2012-05-31 14:22:16 -0600
Update Date	2015-09-17 15:41:51 -0600
Secondary Accession Numbers	ECMDB20002
Identification
Name:	(1R,6R)-6-Hydroxy-2-succinylcyclohexa-2,4-diene-1-carboxylate
Description	2-succinyl-6-hydroxy-2,4-cyclohexadiene-1-carboxylic acid (SHCHC) is the first identified intermediate in the menaquinone biosynthetic pathway. This pathway requires two reactions. They are the decarboxylation of alpha-ketoglutarate by an alpha-ketoglutarate decarboxylase, which results in the formation of succinic semialdehyde-thiamine PPi (TPP) anion, and the addition of the succinic semialdehyde-TPP anion to isochorismate carried out by the enzyme SHCHC synthase. In E. coli, addition of succinic semialdehyde-TPP anion (from 2-oxoglutarate) to isochorismate results in the formation of 2-succinyl-5-enolpyruvyl-6-hydroxy-3-cyclohexene-1-carboxylate (SEPHCHC). In the subsequent reaction, the pyruvoyl group is eliminated, resulting in the prearomatic compound (1R,6R)-6-hydroxy-2-succinylcyclohexa-2,4-diene-1-carboxylate (SHCHC). This is then aromatized to the benzenoid aromatic compound o-succinylbenzoate (OSB) and used as the framework for the construction of the rest of the menaquinone molecule. In this pathway, prenylation in the last step leads to the formation of 1,4-dihydroxy-2-naphtoic acid (DHNA). Subsequently OSB and DHNA formed in this pathway are incorporated into the naphthoquinone ring of menaquinone. SEPHCHC is an unstable compound and in mildly basic solutions, spontaneously undergoes a 2,5-elimination reaction resulting in the formation SHCHC and pyruvate. But the in vivo conversion of SEPHCHC to SHCHC is carried out by SHCHC synthase MenH. Dehydration from SHCHC by the enzyme OSB synthase (MenC) leads to the formation of the benzenoid aromatic compound OSB. The conversion of the benzenoid aromatic compound OSB to the naphthalenoid aromatic compound DHNA is catalyzed by the enzyme OSB-CoA synthetase (MenE). The process has been shown to have an absolute requirement for ATP and CoA. OSB-CoA is suggested as an intermediate. During the formation of OSB-CoA, ATP is hydrolyzed to AMP and PPi.
Structure	MOLSDFPDBSMILESInChI × Structure for #<Compound:0x67422810> Close
Synonyms:	(1R,6R)-2-succinyl-6-hydroxy-2,4-cyclohexadiene-1-carboxylate (1R,6R)-2-succinyl-6-hydroxy-2,4-cyclohexadiene-1-carboxylate (1R,6R)-2-succinyl-6-hydroxy-2,4-cyclohexadiene-1-carboxylic acid (1R,6R)-6-Hydroxy-2-succinylcyclohexa-2,4-diene-1-carboxylic acid 2-(3-CARBOXYPROPIONYL)-6-hydroxy-cyclohexa-2,4-diene carboxylate 2-(3-CARBOXYPROPIONYL)-6-HYDROXY-CYCLOHEXA-2,4-DIENE CARBOXYLIC ACID 2-Succinyl-6-hydroxy-2,4-cyclohexadiene-1-carboxylate 2-Succinyl-6-hydroxy-2,4-cyclohexadiene-1-carboxylic acid NChemBio.2007.11-comp3 Shchc SucCycHexCA
Chemical Formula:	C11H10O6
Weight:	Average: 238.196 Monoisotopic: 238.048835202
InChI Key:	QJYRAJSESKVEAE-PSASIEDQSA-L
InChI:	InChI=1S/C11H12O6/c12-7(4-5-9(14)15)6-2-1-3-8(13)10(6)11(16)17/h1-3,8,10,13H,4-5H2,(H,14,15)(H,16,17)/p-2/t8-,10-/m1/s1
CAS number:	Not Available
IUPAC Name:	(1R,6R)-2-(3-carboxypropanoyl)-6-hydroxycyclohexa-2,4-diene-1-carboxylic acid
Traditional IUPAC Name:	shchc
SMILES:	[H][C@@]1(O)C=CC=C(C(=O)CCC([O-])=O)[C@@]1([H])C([O-])=O
Chemical Taxonomy
Description	belongs to the class of organic compounds known as gamma-keto acids and derivatives. These are organic compounds containing an aldehyde substituted with a keto group on the C4 carbon atom.
Kingdom	Organic compounds
Super Class	Organic acids and derivatives
Class	Keto acids and derivatives
Sub Class	Gamma-keto acids and derivatives
Direct Parent	Gamma-keto acids and derivatives
Alternative Parents	Short-chain keto acids and derivatives Beta hydroxy acids and derivatives Dicarboxylic acids and derivatives Secondary alcohols Ketones Carboxylic acids Organic oxides Hydrocarbon derivatives
Substituents	Gamma-keto acid Beta-hydroxy acid Short-chain keto acid Dicarboxylic acid or derivatives Hydroxy acid Ketone Secondary alcohol Carboxylic acid Carboxylic acid derivative Organooxygen compound Organic oxide Alcohol Carbonyl group Organic oxygen compound Hydrocarbon derivative Aliphatic homomonocyclic compound
Molecular Framework	Aliphatic homomonocyclic compounds
External Descriptors	2-succinyl-6-hydroxycyclohexa-2,4-diene-1-carboxylic acid (CHEBI:39564 )
Physical Properties
State:	Not Available
Charge:	-2
Melting point:	Not Available
Experimental Properties:	Property Value Source
Predicted Properties	Property Value Source Water Solubility 2.73 g/L ALOGPS logP -0.41 ALOGPS logP -0.32 ChemAxon logS -1.9 ALOGPS pKa (Strongest Acidic) 3.63 ChemAxon pKa (Strongest Basic) -3.1 ChemAxon Physiological Charge -2 ChemAxon Hydrogen Acceptor Count 6 ChemAxon Hydrogen Donor Count 3 ChemAxon Polar Surface Area 111.9 Ų ChemAxon Rotatable Bond Count 5 ChemAxon Refractivity 57.88 m³·mol⁻¹ ChemAxon Polarizability 22.36 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:	(1R,6R)-6-Hydroxy-2-succinylcyclohexa-2,4-diene-1-carboxylate <> Water + 2-Succinylbenzoate 2-Succinyl-5-enolpyruvyl-6-hydroxy-3-cyclohexene-1-carboxylate <> (1R,6R)-6-Hydroxy-2-succinylcyclohexa-2,4-diene-1-carboxylate + Pyruvic acid 2-Succinylbenzoate + Water <> (1R,6R)-6-Hydroxy-2-succinylcyclohexa-2,4-diene-1-carboxylate (1R,6R)-6-Hydroxy-2-succinylcyclohexa-2,4-diene-1-carboxylate > 2-Succinylbenzoate + Water 2-Succinyl-5-enolpyruvyl-6-hydroxy-3-cyclohexene-1-carboxylate > (1R,6R)-6-Hydroxy-2-succinylcyclohexa-2,4-diene-1-carboxylate + Pyruvic acid 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 (1R,6R)-6-hydroxy-2-succinylcyclohexa-2,4-diene-1-carboxylate + (1R,6R)-6-Hydroxy-2-succinylcyclohexa-2,4-diene-1-carboxylate > 2-succinylbenzoate + Water + 2-Succinylbenzoate
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 LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Positive splash10-05fr-0490000000-37505c4f192c710ecbdd View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Positive splash10-05dj-1930000000-0ccde18fc3075d5de1db View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Positive splash10-0fba-6900000000-bb7e8d68ddedc2ae3c32 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Negative splash10-007a-0790000000-0c85a3ccb30906916a7f View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Negative splash10-004j-1920000000-ecbb05382b6022769f05 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Negative splash10-054w-5900000000-64762261e0a1410c1df8 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Positive splash10-0095-0980000000-b49a6f77798946f0b1ba View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Positive splash10-0kor-2940000000-3a30aea0722211361a06 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Positive splash10-0ukj-9700000000-4e419d6f1a3b4d06cde0 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Negative splash10-00g0-0790000000-336b6842611dcb1f850b View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Negative splash10-00di-3900000000-92eba81c88d70bc51a87 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Negative splash10-00dl-5900000000-d2ff63b73db8fd6374c1 View in MoNA
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 39564 HMDB ID HMDB0303951 Pubchem Compound ID 5287432 Kegg ID C05817 ChemSpider ID 4449817 Wikipedia ID Not Available BioCyc ID CPD-9923 EcoCyc ID CPD-9923 Ligand Expo 164

Enzymes