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Record Information
Version	2.0
Creation Date	2012-05-31 13:57:48 -0600
Update Date	2015-09-13 12:56:12 -0600
Secondary Accession Numbers	ECMDB03070
Identification
Name:	Shikimic acid
Description	Shikimic acid, more commonly known as its anionic form shikimate, is an important biochemical intermediate in plants and microorganisms. Its name comes from the Japanese flower shikimi (
Structure	MOLSDF3D-SDFPDBSMILESInChI View 3D Structure × Structure for #<Compound:0xb5338a64> Close
Synonyms:	(-)-Shikimate (-)-Shikimic acid L-Shikimate L-Shikimic acid Shikimate Shikimic acid Skikimate Skikimic acid
Chemical Formula:	C7H10O5
Weight:	Average: 174.1513 Monoisotopic: 174.05282343
InChI Key:	JXOHGGNKMLTUBP-HSUXUTPPSA-N
InChI:	InChI=1S/C7H10O5/c8-4-1-3(7(11)12)2-5(9)6(4)10/h1,4-6,8-10H,2H2,(H,11,12)/t4-,5-,6-/m1/s1
CAS number:	138-59-0
IUPAC Name:	(3R,4S,5R)-3,4,5-trihydroxycyclohex-1-ene-1-carboxylic acid
Traditional IUPAC Name:	(-)-shikimate
SMILES:	O[C@@H]1CC(=C[C@@H](O)[C@H]1O)C(O)=O
Chemical Taxonomy
Description	belongs to the class of organic compounds known as shikimic acids and derivatves. These are cyclitols containing a cyclohexanecarboxylic acid substituted with three hydroxyl groups at positions 3, 4, and 5.
Kingdom	Organic compounds
Super Class	Organic oxygen compounds
Class	Organooxygen compounds
Sub Class	Alcohols and polyols
Direct Parent	Shikimic acids and derivatves
Alternative Parents	Secondary alcohols Polyols Monocarboxylic acids and derivatives Carboxylic acids Organic oxides Hydrocarbon derivatives Carbonyl compounds
Substituents	Shikimic acid or derivatives Secondary alcohol Polyol 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	alpha,beta-unsaturated monocarboxylic acid (CHEBI:16119 ) cyclohexenecarboxylic acid (CHEBI:16119 ) hydroxy monocarboxylic acid (CHEBI:16119 )
Physical Properties
State:	Solid
Charge:	-1
Melting point:	186 °C
Experimental Properties:	Property Value Source Water Solubility: 150 mg/mL at 21 oC [YALKOWSKY,SH & DANNENFELSER,RM (1992)] PhysProp
Predicted Properties	Property Value Source Water Solubility 206 g/L ALOGPS logP -1.7 ALOGPS logP -1.6 ChemAxon logS 0.07 ALOGPS pKa (Strongest Acidic) 4.1 ChemAxon pKa (Strongest Basic) -3.2 ChemAxon Physiological Charge -1 ChemAxon Hydrogen Acceptor Count 5 ChemAxon Hydrogen Donor Count 4 ChemAxon Polar Surface Area 97.99 Ų ChemAxon Rotatable Bond Count 1 ChemAxon Refractivity 38.96 m³·mol⁻¹ ChemAxon Polarizability 15.75 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 Adenosine triphosphate + Shikimic acid <> ADP + Hydrogen ion + Shikimate 3-phosphate Adenosine triphosphate + Shikimic acid <> ADP + Shikimate 3-phosphate 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 Shikimic acid + Adenosine triphosphate > Hydrogen ion + Shikimate 3-phosphate + ADP Shikimic acid + NADP > 3-dehydroshikimate + NADPH Adenosine triphosphate + Shikimic acid > ADP + Shikimate 3-phosphate Shikimic acid + NAD(P)(+) > 3-dehydroshikimate + NAD(P)H Quinate + NAD + NADP + Shikimic acid <> 3-Dehydroquinate + NADH + NADPH + Hydrogen ion + 3-Dehydro-shikimate 3-dehydroshikimate + Hydrogen ion + NADPH + 3-Dehydro-shikimate + NADPH > NADP + Shikimic acid Shikimic acid + Adenosine triphosphate > Adenosine diphosphate + Hydrogen ion + shikimate 3-phosphate + ADP + Shikimate 3-phosphate 3 3-Dehydro-shikimate + Hydrogen ion + NADPH <> NADP + Shikimic acid Adenosine triphosphate + Shikimic acid <> ADP + Hydrogen ion + Shikimate 3-phosphate 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
	Concentration Strain Media Growth Status Growth System Temperature Details 14± 0 uM K12 NCM3722 Gutnick minimal complete medium (4.7 g/L KH2PO4; 13.5 g/L K2HPO4; 1 g/L K2SO4; 0.1 g/L MgSO4-7H2O; 10 mM NH4Cl) with 4 g/L glucose Mid-Log Phase Shake flask and filter culture 37 oC PMID: 19561621 Find out more about how we convert literature concentrations.
Spectra
Spectra:	Spectrum Type Description Splash Key GC-MS GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (4 TMS) splash10-0udj-0970000000-42465cd3f3e138b0bc12 View in MoNA GC-MS GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized) splash10-0udi-0790000000-1100443abb8605953f58 View in MoNA GC-MS GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (4 TMS) splash10-00di-9450000000-e6ca954dc1a9c1cc4285 View in MoNA GC-MS GC-MS Spectrum - GC-MS (4 TMS) splash10-0udi-0491000000-49993b9b18e12b9461fc View in MoNA GC-MS GC-MS Spectrum - EI-B (Non-derivatized) splash10-0udi-0391000000-ddb2c574233062a911fa View in MoNA GC-MS GC-MS Spectrum - GC-EI-TOF (Non-derivatized) splash10-0udj-0970000000-42465cd3f3e138b0bc12 View in MoNA GC-MS GC-MS Spectrum - GC-EI-TOF (Non-derivatized) splash10-0udi-0790000000-1100443abb8605953f58 View in MoNA GC-MS GC-MS Spectrum - GC-EI-TOF (Non-derivatized) splash10-00di-9450000000-e6ca954dc1a9c1cc4285 View in MoNA GC-MS GC-MS Spectrum - GC-MS (Non-derivatized) splash10-0udi-0491000000-49993b9b18e12b9461fc View in MoNA Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive splash10-0a4i-4900000000-817f1ed3feb4c763285f View in MoNA Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positive splash10-0092-7119400000-67b0989b5019a72e1016 View in MoNA Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive Not Available View in JSpectraViewer LC-MS/MS LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated) splash10-004i-0900000000-e6ca4ce5acb44dc23a74 View in MoNA LC-MS/MS LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated) splash10-004r-9700000000-18afe769b0ef5ba3fbdb View in MoNA LC-MS/MS LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated) splash10-000i-9100000000-7d0218e803b828de53b2 View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative splash10-01b9-1900000000-fd80f5e7f51d927e8e15 View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative splash10-0a4i-9300000000-cf8a3148fd132540bf97 View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative splash10-0a4i-9000000000-ed28bc20ae43473043c9 View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative splash10-0a4i-9000000000-65249fc24f2de4acf2c7 View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative splash10-0a4i-9000000000-26dfc876ae35c2cdb845 View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative splash10-006x-9600000000-3a5ab91754d9d837d8b4 View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-QQ , negative splash10-01b9-1900000000-6cba5b9b7c4891522045 View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-QQ , negative splash10-0a4i-9300000000-12d15a049b141a37f34e View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-QQ , negative splash10-0a4i-9000000000-ed28bc20ae43473043c9 View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-QQ , negative splash10-0a4i-9000000000-9864f7359ffed65d6ef0 View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-QQ , negative splash10-0a4i-9000000000-26dfc876ae35c2cdb845 View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-QTOF , negative splash10-006x-9600000000-3a5ab91754d9d837d8b4 View in MoNA LC-MS/MS LC-MS/MS Spectrum - 10V, Positive splash10-00ks-4900000000-3c7c11a5c27e1018d328 View in MoNA LC-MS/MS LC-MS/MS Spectrum - 20V, Positive splash10-00di-9000000000-e7907b79b8fbcac9aa36 View in MoNA LC-MS/MS LC-MS/MS Spectrum - 10V, Negative splash10-00di-7900000000-d77a830354efe8731a42 View in MoNA LC-MS/MS LC-MS/MS Spectrum - 40V, Positive splash10-004i-9000000000-9d3f05c288a1c32bd52b View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Positive splash10-004i-0900000000-2a02691107b26b47bfe7 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Positive splash10-004i-0900000000-d0e0c1c61a8cc849c4bc View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Positive splash10-03kc-9500000000-1be2290fb516bd446a61 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Negative splash10-00di-0900000000-563539f2a2fed5cb4f8a View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Negative splash10-00b9-2900000000-229ad430d980f20f597b View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Negative splash10-00b9-9300000000-db4467dbe0ef7549a6e7 View in MoNA 1D NMR 1H 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 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 2D NMR [1H,1H] 2D NMR Spectrum Not Available View in JSpectraViewer 2D NMR [1H,13C] 2D NMR Spectrum Not Available View in JSpectraViewer
References
References:	Bennett, B. D., Kimball, E. H., Gao, M., Osterhout, R., Van Dien, S. J., Rabinowitz, J. D. (2009). "Absolute metabolite concentrations and implied enzyme active site occupancy in Escherichia coli." Nat Chem Biol 5:593-599. Pubmed: 19561621 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 Liu Y, Xie MX, Jiang M, Wang YD: Spectroscopic investigation of the interaction between human serum albumin and three organic acids. Spectrochim Acta A Mol Biomol Spectrosc. 2005 Jul;61(9):2245-51. Pubmed: 15911418 Rose GA: Studies on the chemical nature of urinary chemiluminescence. Br J Urol. 1976 Feb;48(1):61-71. Pubmed: 5168 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 Vijayendran, C., Barsch, A., Friehs, K., Niehaus, K., Becker, A., Flaschel, E. (2008). "Perceiving molecular evolution processes in Escherichia coli by comprehensive metabolite and gene expression profiling." Genome Biol 9:R72. Pubmed: 18402659 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)	Download (PDF)
Links
External Links:	Resource Link CHEBI ID 16119 HMDB ID HMDB03070 Pubchem Compound ID 8742 Kegg ID C00493 ChemSpider ID 8412 Wikipedia Shikimic acid BioCyc ID SHIKIMATE EcoCyc ID SHIKIMATE Ligand Expo SKM

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