3-Dehydro-shikimate (PAMDB000581)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes Transporters
Proteins (3280)
Record Information
Version 1.0
Update Date 1/22/2018 12:54:54 PM
Metabolite IDPAMDB000581
Identification
Name: 3-Dehydro-shikimate
Description:3-dehydro-shikimate is invovled in Chorismic acid biosynthesis. (KEGG)
Structure
Thumb
🔍MOLSDFPDBSMILESInChIView Structure
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
Average Molecular Weight: 171.129
Monoisotopic Molecular Weight: 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
Taxonomy DescriptionThis compound belongs to the class of organic compounds known as cyclohexenones. These 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 ClassOrganooxygen compounds
Class Carbonyl compounds
Sub ClassKetones
Direct Parent Cyclohexenones
Alternative Parents
Substituents
  • Cyclohexenone
  • Secondary alcohol
  • Carboxylic acid salt
  • 1,2-diol
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxide
  • Hydrocarbon derivative
  • Organic anion
  • Alcohol
  • Aliphatic homomonocyclic compound
Molecular Framework Aliphatic homomonocyclic compounds
External Descriptors
Physical Properties
State: Solid
Charge:-1
Melting point: Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility356.0 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count1ChemAxon
Refractivity49.03 m3·mol-1ChemAxon
Polarizability14.76 Å3ChemAxon
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
Shikimic acid + NAD <> 3-Dehydro-shikimate + NADH + Hydrogen ion
3-Dehydroquinate <> Water + 3-Dehydro-shikimate
NAD(P)<sup>+</sup> + Shikimic acid < NAD(P)H + 3-Dehydro-shikimate + Hydrogen ion
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
Pathways:
Spectra
Spectra:
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 IDNot Available
BioCyc ID3-DEHYDRO-SHIKIMATE
EcoCyc ID3-DEHYDRO-SHIKIMATE