3-Dehydroquinate (YMDB00100)

Identification
YMDB IDYMDB00100
Name3-Dehydroquinate
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
Description3-Dehydroquinic acid (DHQ) is the first carbocyclic intermediate of the shikimate pathway. It is created from 3-deoxyarabinoheptulosonate 7-phosphate, a 7-carbon ulonic acid, by the enzyme DHQ synthase. The mechanism of ring closure is complex, but involves an aldol condensation at C-2 and C-7. It has the same structure as quinic acid, which is found in coffee, but the C-3 hydroxyl is oxidized to a ketone group. 3-Dehydroquinic acid undergoes five further enzymatic steps in the remainder of the shikimate pathway to chorismic acid, a precursor to tyrosine, 3-phenylalanine, tryptophan, Vitamin K and folate. 3-Dehydroquinate can also be a precursor to pyrroloquinoline quinone(PQQ), an alternate redox coenzyme involved in oxidative phosphorylation. [Wikipedia]
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
  • 3-Dehydroquinic acid
  • 5-Dehydroquinate
  • 5-dehydroquinic acid
  • Cyclohexan-1,4,5-triol-3-one-1-carboxylic acid
  • 3-Dehydroquinate
  • (1R,3R,4S)-1,3,4-Trihydroxy-5-oxocyclohexanecarboxylic acid
  • 1,3,4-Trihydroxy-5-oxocyclohexanecarboxylic acid
CAS number105735-75-9
WeightAverage: 190.1507
Monoisotopic: 190.047738052
InChI KeyWVMWZWGZRAXUBK-SYTVJDICSA-N
InChIInChI=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
IUPAC Name(1R,3R,4S)-1,3,4-trihydroxy-5-oxocyclohexane-1-carboxylic acid
Traditional IUPAC Name3-dehydroquinic acid
Chemical FormulaC7H10O6
SMILESO[C@@H]1C[C@@](O)(CC(=O)[C@H]1O)C(O)=O
Chemical Taxonomy
Description belongs to the class of organic compounds known as alpha hydroxy acids and derivatives. These are organic compounds containing a carboxylic acid substituted with a hydroxyl group on the adjacent carbon.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassHydroxy acids and derivatives
Sub ClassAlpha hydroxy acids and derivatives
Direct ParentAlpha hydroxy acids and derivatives
Alternative Parents
Substituents
  • Alpha-hydroxy acid
  • Cyclitol or derivatives
  • Cyclic alcohol
  • Tertiary alcohol
  • Cyclic ketone
  • Secondary alcohol
  • Ketone
  • Carboxylic acid derivative
  • Carboxylic acid
  • Polyol
  • Monocarboxylic acid or derivatives
  • Alcohol
  • Carbonyl group
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Organic oxide
  • Organooxygen compound
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External Descriptors
Physical Properties
StateSolid
Charge0
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility702 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity38.7 m³·mol⁻¹ChemAxon
Polarizability16.46 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • Cytoplasm
Organoleptic PropertiesNot Available
SMPDB PathwaysNot Available
KEGG Pathways
Phenylalanine, tyrosine and tryptophan biosynthesisec00400 Map00400
SMPDB ReactionsNot Available
KEGG Reactions
3-Dehydroquinate → water + 3-Dehydroshikimic acid
7-phospho-2-dehydro-3-deoxy-D-arabino-heptonic acid → 3-Dehydroquinate + phosphate
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-006t-0964100000-43f6105696288554732dJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0002-1931000000-57530b3291dd2e565178JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-006t-0964100000-43f6105696288554732dJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0002-1931000000-57530b3291dd2e565178JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0596-9300000000-7ead36d659dabf409016JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positivesplash10-03di-3518900000-ee462a48968d50db188eJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-006y-0900000000-ac10acaee4770b187145JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00fv-0900000000-f009559eda021348f79aJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004i-5900000000-28407ccc61bbac4e43a2JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000j-0900000000-ac45e4ef633567de02beJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-002k-2900000000-994d9ab39014948cbfa2JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0adm-9600000000-2c76a62b61b2ac646326JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0900000000-f9faec316fab8e1b6197JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-2900000000-c25f297abc3454757445JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052f-9200000000-4dbdf526aa7f456fc8b6JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-006x-0900000000-2ad6782757e1bce65eb8JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0096-1900000000-de9c185519f913d3a447JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4m-9000000000-a65ba173f2844b86bd8fJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
References
References:
  • UniProt Consortium (2011). "Ongoing and future developments at the Universal Protein Resource." Nucleic Acids Res 39:D214-D219.21051339
  • Scheer, M., Grote, A., Chang, A., Schomburg, I., Munaretto, C., Rother, M., Sohngen, C., Stelzer, M., Thiele, J., Schomburg, D. (2011). "BRENDA, the enzyme information system in 2011." Nucleic Acids Res 39:D670-D676.21062828
  • Herrgard, M. J., Swainston, N., Dobson, P., Dunn, W. B., Arga, K. Y., Arvas, M., Bluthgen, N., Borger, S., Costenoble, R., Heinemann, M., Hucka, M., Le Novere, N., Li, P., Liebermeister, W., Mo, M. L., Oliveira, A. P., Petranovic, D., Pettifer, S., Simeonidis, E., Smallbone, K., Spasic, I., Weichart, D., Brent, R., Broomhead, D. S., Westerhoff, H. V., Kirdar, B., Penttila, M., Klipp, E., Palsson, B. O., Sauer, U., Oliver, S. G., Mendes, P., Nielsen, J., Kell, D. B. (2008). "A consensus yeast metabolic network reconstruction obtained from a community approach to systems biology." Nat Biotechnol 26:1155-1160.18846089
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI ID17947
HMDB IDHMDB12710
Pubchem Compound ID630
Kegg IDC00944
ChemSpider ID23095481
FOODB IDFDB029168
Wikipedia3-Dehydroquinic_acid
BioCyc IDCPD-10229

Enzymes

Protein Details
1. Pentafunctional AROM polypeptide
General function:
Involved in 3-dehydroquinate dehydratase activity
Specific function:
The AROM polypeptide catalyzes 5 consecutive enzymatic reactions in prechorismate polyaromatic amino acid biosynthesis
Gene Name:
ARO1
Uniprot ID:
P08566
Molecular weight:
174754.0
Reactions
3-deoxy-D-arabino-hept-2-ulosonate 7-phosphate → 3-dehydroquinate + phosphate.
3-dehydroquinate → 3-dehydroshikimate + H(2)O.
Shikimate + NADP(+) → 3-dehydroshikimate + NADPH.
ATP + shikimate → ADP + shikimate 3-phosphate.
Phosphoenolpyruvate + 3-phosphoshikimate → phosphate + 5-O-(1-carboxyvinyl)-3-phosphoshikimate.