Showing Compound Card for 3-Dehydroquinic acid (CDB005037)

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IdentificationTaxonomyOntologyPhysical propertiesSpectraProtein targetPathwaysConcentrationsLinksReferencesenzymes (3) Show 8 proteinsXML
Record Information
Version1.0
Created at2020-04-17 19:02:56 UTC
Updated at2020-11-18 16:39:14 UTC
CannabisDB IDCDB005037
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common Name3-Dehydroquinic acid
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. 3-Dehydroquinic acid is expected to be in Cannabis as all living plants are known to produce and metabolize it.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
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
Chemical FormulaC7H10O6
Average Molecular Weight190.15
Monoisotopic Molecular Weight190.0477
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
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
EI-MS/GC-MS
TypeDescriptionSplash KeyView
GC-MS3-Dehydroquinic acid, non-derivatized, GC-MS Spectrumsplash10-006t-0964100000-43f6105696288554732dSpectrum
GC-MS3-Dehydroquinic acid, non-derivatized, GC-MS Spectrumsplash10-0002-1931000000-57530b3291dd2e565178Spectrum
GC-MS3-Dehydroquinic acid, non-derivatized, GC-MS Spectrumsplash10-006t-0964100000-43f6105696288554732dSpectrum
GC-MS3-Dehydroquinic acid, non-derivatized, GC-MS Spectrumsplash10-0002-1931000000-57530b3291dd2e565178Spectrum
Predicted GC-MS3-Dehydroquinic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0596-9300000000-7ead36d659dabf409016Spectrum
Predicted GC-MS3-Dehydroquinic acid, 4 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-03di-3518900000-ee462a48968d50db188eSpectrum
Predicted GC-MS3-Dehydroquinic acid, 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
Pathways
Pathways
Protein Targets
Enzymes
Protein NameGene NameLocusUniprot IDDetails
Beta-enolaseENO317pter-p11P13929 details
Gamma-enolaseENO212p13P09104 details
Alpha-enolaseENO11p36.2P06733 details
TransportersNot Available
Metal Bindings
Protein NameGene NameLocusUniprot IDDetails
Beta-enolaseENO317pter-p11P13929 details
Gamma-enolaseENO212p13P09104 details
Alpha-enolaseENO11p36.2P06733 details
Receptors
Protein NameGene NameLocusUniprot IDDetails
Gamma-enolaseENO212p13P09104 details
Transcriptional Factors
Protein NameGene NameLocusUniprot IDDetails
Alpha-enolaseENO11p36.2P06733 details
Concentrations Data
Not Available
HMDB IDHMDB0012710
DrugBank IDDB03868
Phenol Explorer Compound IDNot Available
FoodDB 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
References
General ReferencesNot Available

Enzymes

Enzyme Details
1. Beta-enolase
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
Enzyme Details
2. Gamma-enolase
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
Enzyme Details
3. Alpha-enolase
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