3-Dehydro-shikimate (ECMDB04048) (M2MDB000581)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes (3)XML
Proteins (1048)
Record Information
Version2.0
Creation Date2012-05-31 14:03:25 -0600
Update Date2015-09-18 09:17:43 -0600
Secondary Accession Numbers
  • ECMDB04048
Identification
Name:3-Dehydro-shikimate
Description3-dehydro-shikimate is invovled in Chorismic acid biosynthesis. (KEGG)
Structure
Thumb
MOLSDFPDBSMILESInChI
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.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbonyl compounds
Direct ParentCyclohexenones
Alternative Parents
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 FrameworkAliphatic homomonocyclic compounds
External Descriptors
Physical Properties
State:Solid
Charge:-1
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility356 g/LALOGPS
logP-1.2ALOGPS
logP-1ChemAxon
logS0.27ALOGPS
pKa (Strongest Acidic)3.21ChemAxon
pKa (Strongest Basic)-3.3ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area97.66 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity49.03 m³·mol⁻¹ChemAxon
Polarizability14.58 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
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 biosynthesisPW000816 ThumbThumb?image type=greyscaleThumb?image type=simple
Secondary Metabolites: Shikimate PathwayPW000985 ThumbThumb?image type=greyscaleThumb?image type=simple
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 TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0uk9-0900000000-db9503ae5c1cea01876aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0kdi-0900000000-9ff3c52952521fe5bbaaView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-056s-9700000000-c8c4a4ce8fc92084e3f5View in MoNA
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView 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
External Links:
ResourceLink
CHEBI ID16630
HMDB IDHMDB0304122
Pubchem Compound ID5460360
Kegg IDC02637
ChemSpider ID4573915
Wikipedia IDNot Available
BioCyc ID3-DEHYDRO-SHIKIMATE
EcoCyc ID3-DEHYDRO-SHIKIMATE

Enzymes

Protein Details
1. 3-dehydroquinate dehydratase
General function:
Involved in 3-dehydroquinate dehydratase activity
Specific function:
3-dehydroquinate = 3-dehydroshikimate + H(2)O
Gene Name:
aroD
Uniprot ID:
P05194
Molecular weight:
27466
Reactions
3-dehydroquinate = 3-dehydroshikimate + H(2)O.
Protein Details
2. Quinate/shikimate dehydrogenase
General function:
Involved in nucleotide binding
Specific function:
The physiological substrate is not known
Gene Name:
ydiB
Uniprot ID:
P0A6D5
Molecular weight:
31228
Reactions
L-quinate + NAD(P)(+) = 3-dehydroquinate + NAD(P)H.
Shikimate + NAD(P)(+) = 3-dehydroshikimate + NAD(P)H.
Protein Details
3. Shikimate dehydrogenase
General function:
Involved in nucleotide binding
Specific function:
Shikimate + NADP(+) = 3-dehydroshikimate + NADPH
Gene Name:
aroE
Uniprot ID:
P15770
Molecular weight:
29413
Reactions
Shikimate + NADP(+) = 3-dehydroshikimate + NADPH.