NAV

2-Anhydro-3-Fluoro-Quinic Acid

Identification

Generic Name
2-Anhydro-3-Fluoro-Quinic Acid
DrugBank Accession Number
DB02786
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 192.1418
Monoisotopic: 192.043401603
Chemical Formula
C7H9FO5
Synonyms
Not Available
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Pharmacology

Indication

Not Available

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Contraindications & Blackbox Warnings
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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
U3-dehydroquinate dehydrataseNot AvailableStreptomyces coelicolor (strain ATCC BAA-471 / A3(2) / M145)
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

Adverse Effects
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Toxicity

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

Categories

Drug Categories
Not Available
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as quinic acids and derivatives. These are compounds containing a quinic acid moiety (or a derivative thereof), which is a cyclitol made up of a cyclohexane ring that bears four hydroxyl groups at positions 1,3.4, and 5, as well as a carboxylic acid at position 1.
Kingdom
Organic compounds
Super Class
Organic oxygen compounds
Class
Organooxygen compounds
Sub Class
Alcohols and polyols
Direct Parent
Quinic acids and derivatives
Alternative Parents
Alpha hydroxy acids and derivatives / Tertiary alcohols / Secondary alcohols / Fluorohydrins / Vinyl fluorides / Polyols / Monocarboxylic acids and derivatives / Fluoroalkenes / Carboxylic acids / Organofluorides
show 3 more
Substituents
Aliphatic homomonocyclic compound / Alpha-hydroxy acid / Carbonyl group / Carboxylic acid / Carboxylic acid derivative / Fluoroalkene / Fluorohydrin / Haloalkene / Halohydrin / Hydrocarbon derivative
show 11 more
Molecular Framework
Aliphatic homomonocyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
Not Available
CAS number
Not Available
InChI Key
DGZQZSSRYAJDAX-XAHCXIQSSA-N
InChI
InChI=1S/C7H9FO5/c8-3-1-7(13,6(11)12)2-4(9)5(3)10/h1,4-5,9-10,13H,2H2,(H,11,12)/t4-,5-,7+/m1/s1
IUPAC Name
(1R,4S,5R)-3-fluoro-1,4,5-trihydroxycyclohex-2-ene-1-carboxylic acid
SMILES
[H][C@@]1(O)C[C@@](O)(C=C(F)[C@@]1([H])O)C(O)=O

References

General References
Not Available
PubChem Compound
448993
PubChem Substance
46507708
ChemSpider
395633
BindingDB
50170813
ChEMBL
CHEMBL365468
PDBe Ligand
FA3
PDB Entries
1v1j

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

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 Solubility109.0 mg/mLALOGPS
logP-1.2ALOGPS
logP-1.8Chemaxon
logS-0.24ALOGPS
pKa (Strongest Acidic)3.39Chemaxon
pKa (Strongest Basic)-3.3Chemaxon
Physiological Charge-1Chemaxon
Hydrogen Acceptor Count5Chemaxon
Hydrogen Donor Count4Chemaxon
Polar Surface Area97.99 Å2Chemaxon
Rotatable Bond Count1Chemaxon
Refractivity39.32 m3·mol-1Chemaxon
Polarizability15.87 Å3Chemaxon
Number of Rings1Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.8744
Blood Brain Barrier+0.8002
Caco-2 permeable-0.5894
P-glycoprotein substrateNon-substrate0.5496
P-glycoprotein inhibitor INon-inhibitor0.9146
P-glycoprotein inhibitor IINon-inhibitor1.0
Renal organic cation transporterNon-inhibitor0.9524
CYP450 2C9 substrateNon-substrate0.8975
CYP450 2D6 substrateNon-substrate0.8868
CYP450 3A4 substrateNon-substrate0.5962
CYP450 1A2 substrateNon-inhibitor0.9428
CYP450 2C9 inhibitorNon-inhibitor0.9161
CYP450 2D6 inhibitorNon-inhibitor0.9308
CYP450 2C19 inhibitorNon-inhibitor0.9373
CYP450 3A4 inhibitorNon-inhibitor0.9008
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9805
Ames testNon AMES toxic0.8595
CarcinogenicityNon-carcinogens0.9087
BiodegradationNot ready biodegradable0.9695
Rat acute toxicity2.2043 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9924
hERG inhibition (predictor II)Non-inhibitor0.9413
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-MSsplash10-0096-9500000000-9ce74eb7b9e6af63ab1e
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0006-0900000000-049024ed2802f3111187
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0006-0900000000-1dbfd8a1925ba663284c
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-004i-2900000000-c58b1126563d3b704717
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0096-0900000000-ccc39bf915a4838e2805
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-004j-9100000000-5fb8538d6feeea993d89
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-00kf-9700000000-af29b1ba8c286b183f99
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-139.97029
predicted
DeepCCS 1.0 (2019)
[M+H]+142.36623
predicted
DeepCCS 1.0 (2019)
[M+Na]+148.27875
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. 3-dehydroquinate dehydratase
Kind
Protein
Organism
Streptomyces coelicolor (strain ATCC BAA-471 / A3(2) / M145)
Pharmacological action
Unknown
General Function
3-dehydroquinate dehydratase activity
Specific Function
Catalyzes a trans-dehydration via an enolate intermediate.
Gene Name
aroQ
Uniprot ID
P15474
Uniprot Name
3-dehydroquinate dehydratase
Molecular Weight
16681.69 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. [Article]
  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. [Article]

Drug created at June 13, 2005 13:24 / Updated at June 12, 2020 16:52