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Record Information
Version4.0
StatusDetected but not Quantified
Creation Date2009-07-25 00:05:48 UTC
Update Date2020-03-17 15:55:16 UTC
HMDB IDHMDB0012710
Secondary Accession Numbers
  • HMDB12710
Metabolite Identification
Common Name3-Dehydroquinic acid
Description3-Dehydroquinic acid 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-Dehydroquinic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). In most organisms, 3-dehydroquinic acid is synthesized from D-erythrose-4-phosphate in two steps. However, archaea genomes contain no orthologs for the genes that encode these first two steps. Instead, archaeabacteria appear to utilize an alternative pathway in which 3-dehydroquinic acid is synthesized from 6-deoxy-5-ketofructose-1-phosphate and L-aspartate-semialdehyde. These two compounds are first condensed to form 2-amino-3,7-dideoxy-D-threo-hept-6-ulosonate, which cyclizes to 3-dehydroquinic acid. From 3-dehydroquinic acid and on to chorismate, the archaeal pathway appears to be identical to the bacterial pathway.
Structure
Data?1584460515
Synonyms
ValueSource
5-Dehydroquinic acidChEBI
3-Dehydroquinic acidKegg
5-DehydroquinateKegg
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
Chemical FormulaC7H10O6
Average Molecular Weight190.1507
Monoisotopic Molecular Weight190.047738052
IUPAC Name(1R,3R,4S)-1,3,4-trihydroxy-5-oxocyclohexane-1-carboxylic acid
Traditional Name3-dehydroquinic acid
CAS Registry Number10534-44-8
SMILES
O[C@@H]1C[C@@](O)(CC(=O)[C@H]1O)C(O)=O
InChI Identifier
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
InChI KeyWVMWZWGZRAXUBK-SYTVJDICSA-N
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
Ontology
Disposition

Route of exposure:

Biological location:

Source:

Role

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
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
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-006t-0964100000-43f6105696288554732dSpectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0002-1931000000-57530b3291dd2e565178Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-006t-0964100000-43f6105696288554732dSpectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0002-1931000000-57530b3291dd2e565178Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0596-9300000000-7ead36d659dabf409016Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positivesplash10-03di-3518900000-ee462a48968d50db188eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-006y-0900000000-ac10acaee4770b187145Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00fv-0900000000-f009559eda021348f79aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004i-5900000000-28407ccc61bbac4e43a2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000j-0900000000-ac45e4ef633567de02beSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-002k-2900000000-994d9ab39014948cbfa2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0adm-9600000000-2c76a62b61b2ac646326Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)FemaleEpithelial ovarian cancer details
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB03868
Phenol Explorer Compound IDNot Available
FooDB IDFDB029168
KNApSAcK IDC00019664
Chemspider ID388474
KEGG Compound IDC00944
BioCyc IDDEHYDROQUINATE
BiGG IDNot Available
Wikipedia Link3-Dehydroquinic_acid
METLIN IDNot Available
PubChem Compound439351
PDB IDDQA
ChEBI ID17947
Food Biomarker OntologyNot Available
VMH ID3DHQ
MarkerDB ID
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

General function:
Involved in magnesium ion binding
Specific function:
Appears to have a function in striated muscle development and regeneration.
Gene Name:
ENO3
Uniprot ID:
P13929
Molecular weight:
42248.03
General function:
Involved in magnesium ion binding
Specific function:
Has neurotrophic and neuroprotective properties on a broad spectrum of central nervous system (CNS) neurons. Binds, in a calcium-dependent manner, to cultured neocortical neurons and promotes cell survival (By similarity).
Gene Name:
ENO2
Uniprot ID:
P09104
Molecular weight:
47268.125
General function:
Involved in magnesium ion binding
Specific function:
Multifunctional enzyme that, as well as its role in glycolysis, plays a part in various processes such as growth control, hypoxia tolerance and allergic responses. May also function in the intravascular and pericellular fibrinolytic system due to its ability to serve as a receptor and activator of plasminogen on the cell surface of several cell-types such as leukocytes and neurons. Stimulates immunoglobulin production. MBP1 binds to the myc promoter and acts as a transcriptional repressor. May be a tumor suppressor.
Gene Name:
ENO1
Uniprot ID:
P06733
Molecular weight:
36927.84