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Record Information
Version	2.0
Creation Date	2012-05-31 14:03:25 -0600
Update Date	2015-09-18 09:17:43 -0600
Secondary Accession Numbers	ECMDB04048
Identification
Name:	3-Dehydro-shikimate
Description	3-dehydro-shikimate is invovled in Chorismic acid biosynthesis. (KEGG)
Structure	MOLSDFPDBSMILESInChI × Structure for #<Compound:0xa936e328> Close
Synonyms:	(4S,5R)-4,5-dihydroxy-3-oxocyclohex-1-ene-1-carboxylate (4S,5R)-4,5-dihydroxy-3-oxocyclohex-1-ene-1-carboxylic acid 3-Dehydro-shikimic acid 3-Dehydroshikimate 3-Dehydroshikimic acid 5-Dehydroshikimate 5-Dehydroshikimic acid
Chemical Formula:	C7H7O5
Weight:	Average: 171.129 Monoisotopic: 171.029896905
InChI Key:	SLWWJZMPHJJOPH-UHFFFAOYSA-M
InChI:	InChI=1S/C7H8O5/c8-4-1-3(7(11)12)2-5(9)6(4)10/h1,5-6,9-10H,2H2,(H,11,12)/p-1
CAS number:	10457-99-5
IUPAC Name:	4,5-dihydroxy-3-oxocyclohex-1-ene-1-carboxylate
Traditional IUPAC Name:	4,5-dihydroxy-3-oxocyclohex-1-ene-1-carboxylate
SMILES:	OC1CC(=CC(=O)C1O)C([O-])=O
Chemical Taxonomy
Description	belongs to the class of organic compounds known as cyclohexenones. Cyclohexenones are compounds containing a cylohexenone moiety, which is a six-membered aliphatic ring that carries a ketone and has one endocyclic double bond.
Kingdom	Organic compounds
Super Class	Organic oxygen compounds
Class	Organooxygen compounds
Sub Class	Carbonyl compounds
Direct Parent	Cyclohexenones
Alternative Parents	Secondary alcohols 1,2-diols Monocarboxylic acids and derivatives Carboxylic acids Organic oxides Hydrocarbon derivatives Organic anions
Substituents	Cyclohexenone Secondary alcohol 1,2-diol Monocarboxylic acid or derivatives Carboxylic acid Carboxylic acid derivative Organic oxide Hydrocarbon derivative Alcohol Organic anion Aliphatic homomonocyclic compound
Molecular Framework	Aliphatic homomonocyclic compounds
External Descriptors	a small molecule (3-DEHYDRO-SHIKIMATE )
Physical Properties
State:	Solid
Charge:	-1
Melting point:	Not Available
Experimental Properties:	Property Value Source
Predicted Properties	Property Value Source Water Solubility 356 g/L ALOGPS logP -1.2 ALOGPS logP -1 ChemAxon logS 0.27 ALOGPS pKa (Strongest Acidic) 3.21 ChemAxon pKa (Strongest Basic) -3.3 ChemAxon Physiological Charge -1 ChemAxon Hydrogen Acceptor Count 5 ChemAxon Hydrogen Donor Count 2 ChemAxon Polar Surface Area 97.66 Ų ChemAxon Rotatable Bond Count 1 ChemAxon Refractivity 49.03 m³·mol⁻¹ ChemAxon Polarizability 14.58 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:	3-Dehydro-shikimate + Hydrogen ion + NADPH <> NADP + Shikimic acid 3-Dehydroquinate <> 3-Dehydro-shikimate + Water Shikimic acid + NADP <> 3-Dehydro-shikimate + NADPH + Hydrogen ion Shikimic acid + NAD <> 3-Dehydro-shikimate + NADH + Hydrogen ion NAD(P)<sup>+</sup> + Shikimic acid < NAD(P)H + 3-Dehydro-shikimate + Hydrogen ion NADP + Shikimic acid < Hydrogen ion + NADPH + 3-Dehydro-shikimate Quinate + NAD + NADP + Shikimic acid <> 3-Dehydroquinate + NADH + NADPH + Hydrogen ion + 3-Dehydro-shikimate 3-Dehydroquinate > Water + 3-dehydroshikimate + 3-Dehydro-shikimate 3-dehydroshikimate + Hydrogen ion + NADPH + 3-Dehydro-shikimate + NADPH > NADP + Shikimic acid 3 3-Dehydro-shikimate + Hydrogen ion + NADPH <> NADP + Shikimic acid 3 3-Dehydro-shikimate + Hydrogen ion + NADPH <> NADP + Shikimic acid
SMPDB Pathways:	Chorismate biosynthesis PW000816 Secondary Metabolites: Shikimate Pathway PW000985
KEGG Pathways:	Metabolic pathways eco01100 Phenylalanine, tyrosine and tryptophan biosynthesis ec00400
EcoCyc Pathways:	chorismate biosynthesis from 3-dehydroquinate PWY-6163
Concentrations
	Not Available
Spectra
Spectra:	Spectrum Type Description Splash Key Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Negative splash10-0uk9-0900000000-db9503ae5c1cea01876a View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Negative splash10-0kdi-0900000000-9ff3c52952521fe5bbaa View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Negative splash10-056s-9700000000-c8c4a4ce8fc92084e3f5 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 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 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
Synthesis Reference:	Not Available
Material Safety Data Sheet (MSDS)	Not Available
Links
External Links:	Resource Link CHEBI ID 16630 HMDB ID HMDB0304122 Pubchem Compound ID 5460360 Kegg ID C02637 ChemSpider ID 4573915 Wikipedia ID Not Available BioCyc ID 3-DEHYDRO-SHIKIMATE EcoCyc ID 3-DEHYDRO-SHIKIMATE

Enzymes