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Record Information
Version	2.0
Creation Date	2012-05-31 14:03:28 -0600
Update Date	2015-06-03 15:54:40 -0600
Secondary Accession Numbers	ECMDB04049
Identification
Name:	3-Dehydroquinate
Description	3-dehydroquinate is a member of the chemical class known as Cyclitols and Derivatives. These are compounds containing a cycloalkane moiety with one hydroxyl group on each of three or more ring atoms. 3-dehydroquinate is invovled in phenylalanine, tyrosine and tryptophan biosynthesis, and the biosynthesis of secondary metabolites. Dehydroquinate is involved in the shikimate pathway. The aroB-encoded enzyme dehydroquinate synthase is the second enzyme of this pathway, and it catalyzes the cyclization of 3-deoxy-D-arabino-heptulosonate-7-phosphate in 3-dehydroquinate. The aroB-encoded enzyme dehydroquinate synthase is the second enzyme of this pathway, and it catalyzes the cyclization of 3-deoxy-D-arabino-heptulosonate-7-phosphate in 3-dehydroquinate. (PMID 17586643) The aroB gene encoding dehydroquinate synthase (DHQS), which is a potential antibiotic target, was identified from the plant-pathogenic bacterium Xanthomonas oryzae pv. (PMID 19052366)
Structure	MOLSDFPDBSMILESInChI × Structure for #<Compound:0xaae89284> Close
Synonyms:	3-Dehydroquinic acid 3DQA 5-De-H-quinate 5-De-H-quinic acid 5-Dehydroquinate 5-Dehydroquinic acid Cyclohexan-1,4,5-triol-3-one-1-carboxylate Cyclohexan-1,4,5-triol-3-one-1-carboxylic acid
Chemical Formula:	C7H10O6
Weight:	Average: 190.1507 Monoisotopic: 190.047738052
InChI Key:	WVMWZWGZRAXUBK-SYTVJDICSA-N
InChI:	InChI=1S/C7H10O6/c8-3-1-7(13,6(11)12)2-4(9)5(3)10/h3,5,8,10,13H,1-2H2,(H,11,12)/t3-,5+,7-/m1/s1
CAS number:	Not Available
IUPAC Name:	(1R,3R,4S)-1,3,4-trihydroxy-5-oxocyclohexane-1-carboxylic acid
Traditional IUPAC Name:	3-dehydroquinic acid
SMILES:	O[C@@H]1C[C@@](O)(CC(=O)[C@H]1O)C(O)=O
Chemical Taxonomy
Description	belongs to the class of organic compounds known as alpha hydroxy acids and derivatives. These are organic compounds containing a carboxylic acid substituted with a hydroxyl group on the adjacent carbon.
Kingdom	Organic compounds
Super Class	Organic acids and derivatives
Class	Hydroxy acids and derivatives
Sub Class	Alpha hydroxy acids and derivatives
Direct Parent	Alpha hydroxy acids and derivatives
Alternative Parents	Cyclitols and derivatives Tertiary alcohols Secondary alcohols Cyclic ketones Polyols Monocarboxylic acids and derivatives Carboxylic acids Organic oxides Hydrocarbon derivatives
Substituents	Alpha-hydroxy acid Cyclitol or derivatives Cyclic alcohol Tertiary alcohol Cyclic ketone Secondary alcohol Ketone Carboxylic acid derivative Carboxylic acid Polyol Monocarboxylic acid or derivatives Alcohol Carbonyl group Hydrocarbon derivative Organic oxygen compound Organic oxide Organooxygen compound Aliphatic homomonocyclic compound
Molecular Framework	Aliphatic homomonocyclic compounds
External Descriptors	4-oxo monocarboxylic acid (CHEBI:17947 ) 5-hydroxy monocarboxylic acid (CHEBI:17947 ) 4-hydroxy monocarboxylic acid (CHEBI:17947 ) 2-hydroxy monocarboxylic acid (CHEBI:17947 )
Physical Properties
State:	Not Available
Charge:	-1
Melting point:	Not Available
Experimental Properties:	Property Value Source
Predicted Properties	Property Value Source Water Solubility 702 g/L ALOGPS logP -2 ALOGPS logP -2.1 ChemAxon logS 0.57 ALOGPS pKa (Strongest Acidic) 3.3 ChemAxon pKa (Strongest Basic) -3.3 ChemAxon Physiological Charge -1 ChemAxon Hydrogen Acceptor Count 6 ChemAxon Hydrogen Donor Count 4 ChemAxon Polar Surface Area 115.06 Ų ChemAxon Rotatable Bond Count 1 ChemAxon Refractivity 38.7 m³·mol⁻¹ ChemAxon Polarizability 16.46 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:	NAD + Quinate <> 3-Dehydroquinate +2 Hydrogen ion + NADH 3-Dehydroquinate <> 3-Dehydro-shikimate + Water 2-Dehydro-3-deoxy-D-arabino-heptonate 7-phosphate <> 3-Dehydroquinate + Phosphate Quinate + NAD <> 3-Dehydroquinate + NADH + Hydrogen ion Quinate + NADP <> 3-Dehydroquinate + NADPH + Hydrogen ion 2-Dehydro-3-deoxy-D-arabino-heptonate 7-phosphate > Phosphate + 3-Dehydroquinate NAD(P)<sup>+</sup> + Quinate NAD(P)H + 3-Dehydroquinate + Hydrogen ion 2-Dehydro-3-deoxy-D-arabino-heptonate 7-phosphate > 3-Dehydroquinate + Inorganic phosphate 3-Dehydroquinate > 3-dehydroshikimate + Water Quinate + NAD(P)(+) > 3-Dehydroquinate + NAD(P)H Quinate + NAD + NADP + Shikimic acid <> 3-Dehydroquinate + NADH + NADPH + Hydrogen ion + 3-Dehydro-shikimate 3-deoxy-D-arabino-heptulosonate-7-phosphate > Phosphate + 3-Dehydroquinate 3-Dehydroquinate > Water + 3-dehydroshikimate + 3-Dehydro-shikimate 2 2-Dehydro-3-deoxy-D-arabino-heptonate 7-phosphate <>3 3-Dehydroquinate + Phosphate 2 2-Dehydro-3-deoxy-D-arabino-heptonate 7-phosphate <>3 3-Dehydroquinate + Phosphate
SMPDB Pathways:	Chorismate biosynthesis PW000816 Secondary Metabolites: Shikimate Pathway PW000985
KEGG Pathways:	Metabolic pathways eco01100 Phenylalanine, tyrosine and tryptophan biosynthesis ec00400
EcoCyc Pathways:	3-dehydroquinate biosynthesis I PWY-6164 chorismate biosynthesis from 3-dehydroquinate PWY-6163
Concentrations
	Not Available
Spectra
Spectra:	Spectrum Type Description Splash Key GC-MS GC-MS Spectrum - EI-B (Non-derivatized) splash10-006t-0964100000-43f6105696288554732d View in MoNA GC-MS GC-MS Spectrum - GC-EI-TOF (Non-derivatized) splash10-0002-1931000000-57530b3291dd2e565178 View in MoNA GC-MS GC-MS Spectrum - EI-B (Non-derivatized) splash10-006t-0964100000-43f6105696288554732d View in MoNA GC-MS GC-MS Spectrum - GC-EI-TOF (Non-derivatized) splash10-0002-1931000000-57530b3291dd2e565178 View in MoNA Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive splash10-0596-9300000000-7ead36d659dabf409016 View in MoNA Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positive splash10-03di-3518900000-ee462a48968d50db188e View in MoNA Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive Not Available View in JSpectraViewer Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Positive splash10-006y-0900000000-ac10acaee4770b187145 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Positive splash10-00fv-0900000000-f009559eda021348f79a View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Positive splash10-004i-5900000000-28407ccc61bbac4e43a2 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Negative splash10-000j-0900000000-ac45e4ef633567de02be View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Negative splash10-002k-2900000000-994d9ab39014948cbfa2 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Negative splash10-0adm-9600000000-2c76a62b61b2ac646326 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Negative splash10-000i-0900000000-f9faec316fab8e1b6197 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Negative splash10-000i-2900000000-c25f297abc3454757445 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Negative splash10-052f-9200000000-4dbdf526aa7f456fc8b6 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Positive splash10-006x-0900000000-2ad6782757e1bce65eb8 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Positive splash10-0096-1900000000-de9c185519f913d3a447 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Positive splash10-0a4m-9000000000-a65ba173f2844b86bd8f View in MoNA 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 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer
References
References:	de Mendonca, J. D., Ely, F., Palma, M. S., Frazzon, J., Basso, L. A., Santos, D. S. (2007). "Functional characterization by genetic complementation of aroB-encoded dehydroquinate synthase from Mycobacterium tuberculosis H37Rv and its heterologous expression and purification." J Bacteriol 189:6246-6252. Pubmed: 17586643 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 Ngo, P. T., Natarajan, S., Kim, H., Hung, H. K., Kim, J. G., Lee, B. M., Ahn, Y. J., Kang, L. W. (2008). "Cloning, expression, crystallization and preliminary X-ray crystallographic analysis of 3-dehydroquinate synthase, Xoo1243, from Xanthomonas oryzae pv. oryzae." Acta Crystallogr Sect F Struct Biol Cryst Commun 64:1128-1131. Pubmed: 19052366 van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. Pubmed: 17765195
Synthesis Reference:	Not Available
Material Safety Data Sheet (MSDS)	Not Available
Links
External Links:	Resource Link CHEBI ID 32364 HMDB ID HMDB12710 Pubchem Compound ID 439351 Kegg ID C00944 ChemSpider ID 388474 Wikipedia ID 3-Dehydroquinic_acid BioCyc ID DEHYDROQUINATE EcoCyc ID DEHYDROQUINATE Ligand Expo DQA

Enzymes