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Record Information
Version3.6
Creation Date2009-07-25 00:05:48 UTC
Update Date2016-02-11 01:25:11 UTC
HMDB IDHMDB12710
Secondary Accession NumbersNone
Metabolite Identification
Common Name3-Dehydroquinate
DescriptionIn most organisms, 3-dehydroquinate is synthesized from D-erythrose-4-phosphate in two steps. However, the genomes of the archaea contain no orthologs for the genes that encode these first two steps. Instead, archaeabacteria appear to utilize an alternative pathway in which 3-dehydroquinate 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-dehydroquinate. From 3-dehydroquinate and on to chorismate, the archaeal pathway appears to be identical to the bacterial pathway.
Structure
Thumb
Synonyms
ValueSource
5-Dehydroquinic acidChEBI
5-DehydroquinateGenerator
3-Dehydroquinic acidGenerator
Cyclohexan-1,4,5-triol-3-one-1-carboxylic 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 NumberNot Available
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 KeyInChIKey=WVMWZWGZRAXUBK-SYTVJDICSA-N
Chemical 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.
KingdomOrganic compounds
Super ClassOrganooxygen compounds
ClassAlcohols and polyols
Sub ClassCyclic alcohols and derivatives
Direct ParentCyclitols 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 FrameworkAliphatic homomonocyclic compounds
External Descriptors
Ontology
StatusDetected but not Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot Available
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 Solubility702.0 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
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-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
Biological Properties
Cellular LocationsNot Available
Biofluid Locations
  • Urine
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
Not Available
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
UrineDetected but not QuantifiedNot ApplicableAdult (>18 years old)FemaleEpithelial ovarian cancer details
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB029168
KNApSAcK IDNot Available
Chemspider ID388474
KEGG Compound IDC00944
BioCyc IDCPD-10229
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB12710
Metagene LinkHMDB12710
METLIN IDNot Available
PubChem Compound439351
PDB IDDQA
ChEBI ID17947
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