3-Dehydroquinic Acid

Identification

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Name
3-Dehydroquinic Acid
Accession Number
DB03868  (EXPT01264)
Type
Small Molecule
Groups
Experimental
Description
Not Available
Structure
Thumb
Synonyms
Not Available
Categories
UNII
Not Available
CAS number
Not Available
Weight
Average: 190.1507
Monoisotopic: 190.047738052
Chemical Formula
C7H10O6
InChI Key
WVMWZWGZRAXUBK-SYTVJDICSA-N
InChI
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
IUPAC Name
(1R,3R,4S)-1,3,4-trihydroxy-5-oxocyclohexane-1-carboxylic acid
SMILES
O[C@@H]1C[C@@](O)(CC(=O)[C@H]1O)C(O)=O

Pharmacology

Indication
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
U3-dehydroquinate dehydrataseNot AvailableHelicobacter pylori (strain ATCC 700392 / 26695)
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Not Available
Food Interactions
Not Available

References

General References
Not Available
External Links
Human Metabolome Database
HMDB0012710
KEGG Compound
C00944
PubChem Compound
439351
PubChem Substance
46508711
ChemSpider
388474
ChEBI
17947
HET
DQA
PDB Entries
1j2y / 3m7w / 3nnt / 5ydb

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not 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 FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.5701
Blood Brain Barrier+0.6547
Caco-2 permeable-0.8106
P-glycoprotein substrateNon-substrate0.5932
P-glycoprotein inhibitor INon-inhibitor0.9594
P-glycoprotein inhibitor IINon-inhibitor0.9907
Renal organic cation transporterNon-inhibitor0.9389
CYP450 2C9 substrateNon-substrate0.8638
CYP450 2D6 substrateNon-substrate0.8992
CYP450 3A4 substrateNon-substrate0.6068
CYP450 1A2 substrateNon-inhibitor0.9833
CYP450 2C9 inhibitorNon-inhibitor0.9748
CYP450 2D6 inhibitorNon-inhibitor0.9598
CYP450 2C19 inhibitorNon-inhibitor0.969
CYP450 3A4 inhibitorNon-inhibitor0.9502
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity1.0
Ames testNon AMES toxic0.9152
CarcinogenicityNon-carcinogens0.9365
BiodegradationNot ready biodegradable0.5074
Rat acute toxicity1.9269 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9917
hERG inhibition (predictor II)Non-inhibitor0.9602
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
GC-MS Spectrum - EI-BGC-MSsplash10-006t-0964100000-43f6105696288554732d
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-0002-1931000000-57530b3291dd2e565178
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-006y-0900000000-ac10acaee4770b187145
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-00fv-0900000000-f009559eda021348f79a
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-004i-5900000000-28407ccc61bbac4e43a2
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-000j-0900000000-ac45e4ef633567de02be
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-002k-2900000000-994d9ab39014948cbfa2
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0adm-9600000000-2c76a62b61b2ac646326

Taxonomy

Description
This compound 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.
Kingdom
Organic compounds
Super Class
Organic acids and derivatives
Class
Hydroxy acids and derivatives
Sub Class
Alpha hydroxy acids and derivatives
Direct Parent
Alpha hydroxy acids and derivatives
Alternative Parents
Cyclitols and derivatives / Tertiary alcohols / Secondary alcohols / Cyclic ketones / Polyols / Monocarboxylic acids and derivatives / Carboxylic acids / Organic oxides / Hydrocarbon derivatives
Substituents
Alpha-hydroxy acid / Cyclitol or derivatives / Cyclic alcohol / Tertiary alcohol / Cyclic ketone / Secondary alcohol / Ketone / Carboxylic acid derivative / Carboxylic acid / Polyol
Molecular Framework
Aliphatic homomonocyclic compounds
External Descriptors
4-oxo monocarboxylic acid, 5-hydroxy monocarboxylic acid, 4-hydroxy monocarboxylic acid, 2-hydroxy monocarboxylic acid (CHEBI:17947)

Targets

Kind
Protein
Organism
Helicobacter pylori (strain ATCC 700392 / 26695)
Pharmacological action
Unknown
General Function
3-dehydroquinate dehydratase activity
Specific Function
Catalyzes a trans-dehydration via an enolate intermediate.
Gene Name
aroQ
Uniprot ID
Q48255
Uniprot Name
3-dehydroquinate dehydratase
Molecular Weight
18483.21 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]

Drug created on June 13, 2005 07:24 / Updated on September 02, 2019 17:49