Record Information
Version 1.0
Update Date 1/22/2018 11:54:53 AM
Metabolite IDPAMDB000582
Identification
Name: 3-Dehydroquinate
Description:3-dehydroquinate is a member of the chemical class known as Cyclitols and Derivatives. These are compounds containing a cycloalkane moiety with one hydroxyl group on each of three or more ring atoms. 3-dehydroquinate is invovled in phenylalanine, tyrosine and tryptophan biosynthesis, and the biosynthesis of secondary metabolites. Dehydroquinate is involved in the shikimate pathway. The aroB-encoded enzyme dehydroquinate synthase is the second enzyme of this pathway, and it catalyzes the cyclization of 3-deoxy-D-arabino-heptulosonate-7-phosphate in 3-dehydroquinate. The aroB-encoded enzyme dehydroquinate synthase is the second enzyme of this pathway, and it catalyzes the cyclization of 3-deoxy-D-arabino-heptulosonate-7-phosphate in 3-dehydroquinate. (PMID 17586643) The aroB gene encoding dehydroquinate synthase (DHQS), which is a potential antibiotic target, was identified from the plant-pathogenic bacterium Xanthomonas oryzae pv. (PMID 19052366)
Structure
Thumb
Synonyms:
  • 3-Dehydroquinic acid
  • 3DQA
  • 5-De-H-quinate
  • 5-De-H-quinic acid
  • 5-Dehydroquinate
  • 5-Dehydroquinic acid
  • Cyclohexan-1,4,5-triol-3-one-1-carboxylate
  • Cyclohexan-1,4,5-triol-3-one-1-carboxylic acid
Chemical Formula: C7H10O6
Average Molecular Weight: 190.1507
Monoisotopic Molecular Weight: 190.047738052
InChI Key: WVMWZWGZRAXUBK-SYTVJDICSA-N
InChI:InChI=1S/C7H10O6/c8-3-1-7(13,6(11)12)2-4(9)5(3)10/h3,5,8,10,13H,1-2H2,(H,11,12)/t3-,5+,7-/m1/s1
CAS number: Not Available
IUPAC Name:(1R,3R,4S)-1,3,4-trihydroxy-5-oxocyclohexane-1-carboxylic acid
Traditional IUPAC Name: 3-dehydroquinic acid
SMILES:O[C@@H]1C[C@@](O)(CC(=O)[C@H]1O)C(O)=O
Chemical Taxonomy
Taxonomy DescriptionThis compound belongs to the class of organic compounds known as cyclitols and derivatives. These are compounds containing a cycloalkane moiety with one hydroxyl group on each of three or more ring atoms.
Kingdom Organic compounds
Super ClassOrganooxygen compounds
Class Alcohols and polyols
Sub ClassCyclic alcohols and derivatives
Direct Parent Cyclitols and derivatives
Alternative Parents
Substituents
  • Cyclitol derivative
  • Cyclohexanone
  • Cyclohexanol
  • Hydroxy acid
  • Alpha-hydroxy acid
  • Tertiary alcohol
  • Cyclic ketone
  • Secondary alcohol
  • Polyol
  • Ketone
  • 1,2-diol
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Carbonyl group
  • Aliphatic homomonocyclic compound
Molecular Framework Aliphatic homomonocyclic compounds
External Descriptors
Physical Properties
State: Not Available
Charge:-1
Melting point: Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility702.0 mg/mLALOGPS
logP-2ALOGPS
logP-2.1ChemAxon
logS0.57ALOGPS
pKa (Strongest Acidic)3.3ChemAxon
pKa (Strongest Basic)-3.3ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area115.06 Å2ChemAxon
Rotatable Bond Count1ChemAxon
Refractivity38.7 m3·mol-1ChemAxon
Polarizability16.46 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Cytoplasm
Reactions:
Pathways:
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MSNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-006y-0900000000-ac10acaee4770b187145View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00fv-0900000000-f009559eda021348f79aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004i-5900000000-28407ccc61bbac4e43a2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000j-0900000000-ac45e4ef633567de02beView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-002k-2900000000-994d9ab39014948cbfa2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0adm-9600000000-2c76a62b61b2ac646326View in MoNA
References
References:
  • de Mendonca, J. D., Ely, F., Palma, M. S., Frazzon, J., Basso, L. A., Santos, D. S. (2007). "Functional characterization by genetic complementation of aroB-encoded dehydroquinate synthase from Mycobacterium tuberculosis H37Rv and its heterologous expression and purification." J Bacteriol 189:6246-6252. Pubmed: 17586643
  • 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
  • Ngo, P. T., Natarajan, S., Kim, H., Hung, H. K., Kim, J. G., Lee, B. M., Ahn, Y. J., Kang, L. W. (2008). "Cloning, expression, crystallization and preliminary X-ray crystallographic analysis of 3-dehydroquinate synthase, Xoo1243, from Xanthomonas oryzae pv. oryzae." Acta Crystallogr Sect F Struct Biol Cryst Commun 64:1128-1131. Pubmed: 19052366
  • 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
Synthesis Reference: Not Available
Material Safety Data Sheet (MSDS) Not Available
External Links:
ResourceLink
CHEBI ID32364
HMDB IDHMDB12710
Pubchem Compound ID439351
Kegg IDC00944
ChemSpider ID388474
Wikipedia IDNot Available
BioCyc IDDEHYDROQUINATE
EcoCyc IDDEHYDROQUINATE
Ligand ExpoDQA