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Showing Compound 3-Dehydroquinate (FDB029168)

Record Information
Version1.0
Creation date2011-09-21 01:51:08 UTC
Update date2020-09-17 15:39:52 UTC
Primary IDFDB029168
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name3-Dehydroquinate
Description3-Dehydroquinate 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. 3-Dehydroquinate is an extremely weak basic (essentially neutral) compound (based on its pKa). 3-Dehydroquinate exists in all living species, ranging from bacteria to humans. Outside of the human body, 3-Dehydroquinate has been detected, but not quantified in, several different foods, such as other bread, shiitakes, pili nuts, pepper (c. pubescens), and sourdocks. This could make 3-dehydroquinate a potential biomarker for the consumption of these foods. A 4-oxo monocarboxylic acid derived from quinic acid by oxidation of the hydroxy group at position 3 to the corresponding keto group.
CAS NumberNot Available
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
5-Dehydroquinic acidChEBI
5-DehydroquinateKegg
3-DehydroquinateGenerator
3-Dehydroquinic acidGenerator, KEGG
Cyclohexan-1,4,5-triol-3-one-1-carboxylic acidHMDB
(1R,3R,4S)-1,3,4-Trihydroxy-5-oxocyclohexanecarboxylic acidHMDB
1,3,4-Trihydroxy-5-oxocyclohexanecarboxylic acidHMDB
5-dehydroquinic acidhmdb
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC7H10O6
IUPAC name(1R,3R,4S)-1,3,4-trihydroxy-5-oxocyclohexane-1-carboxylic acid
InChI IdentifierInChI=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
InChI KeyWVMWZWGZRAXUBK-SYTVJDICSA-N
Isomeric SMILESO[C@@H]1C[C@@](O)(CC(=O)[C@H]1O)C(O)=O
Average Molecular Weight190.1507
Monoisotopic Molecular Weight190.047738052
Classification
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
Ontology
Disposition

Route of exposure:

Biological location:

Source:

Role

Industrial application:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
GC-MS3-Dehydroquinate, non-derivatized, GC-MS Spectrumsplash10-006t-0964100000-43f6105696288554732dSpectrum
GC-MS3-Dehydroquinate, non-derivatized, GC-MS Spectrumsplash10-0002-1931000000-57530b3291dd2e565178Spectrum
GC-MS3-Dehydroquinate, non-derivatized, GC-MS Spectrumsplash10-006t-0964100000-43f6105696288554732dSpectrum
GC-MS3-Dehydroquinate, non-derivatized, GC-MS Spectrumsplash10-0002-1931000000-57530b3291dd2e565178Spectrum
Predicted GC-MS3-Dehydroquinate, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0596-9300000000-7ead36d659dabf409016Spectrum
Predicted GC-MS3-Dehydroquinate, 4 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-03di-3518900000-ee462a48968d50db188eSpectrum
Predicted GC-MS3-Dehydroquinate, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-006y-0900000000-ac10acaee4770b1871452015-09-15View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00fv-0900000000-f009559eda021348f79a2015-09-15View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004i-5900000000-28407ccc61bbac4e43a22015-09-15View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000j-0900000000-ac45e4ef633567de02be2015-09-15View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-002k-2900000000-994d9ab39014948cbfa22015-09-15View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0adm-9600000000-2c76a62b61b2ac6463262015-09-15View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0900000000-f9faec316fab8e1b61972021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-2900000000-c25f297abc34547574452021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052f-9200000000-4dbdf526aa7f456fc8b62021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-006x-0900000000-2ad6782757e1bce65eb82021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0096-1900000000-de9c185519f913d3a4472021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4m-9000000000-a65ba173f2844b86bd8f2021-09-24View Spectrum
NMRNot Available
ChemSpider ID388474
ChEMBL IDNot Available
KEGG Compound IDC00944
Pubchem Compound ID439351
Pubchem Substance IDNot Available
ChEBI ID32364
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB12710
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDDQA
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference