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
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
Polarizability14.76 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
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
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 IDNot Available
Pubchem Compound ID5460360
Kegg IDC02637
ChemSpider ID4573915
Wikipedia ID3-Dehydroshikimic acid
BioCyc ID3-DEHYDRO-SHIKIMATE
EcoCyc ID3-DEHYDRO-SHIKIMATE

Enzymes

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.
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.
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.