NAV

3-fluoro-6-(4-fluorophenyl)-2-hydroxy-6-oxohexa-2,4-dienoic acid

Identification

Generic Name
3-fluoro-6-(4-fluorophenyl)-2-hydroxy-6-oxohexa-2,4-dienoic acid
DrugBank Accession Number
DB07510
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 254.1863
Monoisotopic: 254.039065154
Chemical Formula
C12H8F2O4
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
U2-hydroxy-6-oxo-6-phenylhexa-2,4-dienoate hydrolaseNot AvailableBurkholderia xenovorans (strain LB400)
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 medium-chain keto acids and derivatives. These are keto acids with a 6 to 12 carbon atoms long side chain.
Kingdom
Organic compounds
Super Class
Organic acids and derivatives
Class
Keto acids and derivatives
Sub Class
Medium-chain keto acids and derivatives
Direct Parent
Medium-chain keto acids and derivatives
Alternative Parents
Aryl ketones / Benzoyl derivatives / Hydroxy fatty acids / Halogenated fatty acids / Fluorobenzenes / Unsaturated fatty acids / Aryl fluorides / Vinylogous halides / Acryloyl compounds / Enones
show 7 more
Substituents
Acryloyl-group / Alpha,beta-unsaturated ketone / Aromatic homomonocyclic compound / Aryl fluoride / Aryl halide / Aryl ketone / Benzenoid / Benzoyl / Carbonyl group / Carboxylic acid
show 23 more
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
Not Available
CAS number
Not Available
InChI Key
CPZFGNOKCMJZFO-BTHQEHEQSA-N
InChI
InChI=1S/C12H8F2O4/c13-8-3-1-7(2-4-8)10(15)6-5-9(14)11(16)12(17)18/h1-6,16H,(H,17,18)/b6-5+,11-9-
IUPAC Name
(2Z,4E)-3-fluoro-6-(4-fluorophenyl)-2-hydroxy-6-oxohexa-2,4-dienoic acid
SMILES
OC(=O)C(\O)=C(\F)/C=C/C(=O)C1=CC=C(F)C=C1

References

General References
Not Available
PubChem Compound
23636976
PubChem Substance
99443981
ChemSpider
22376696
ZINC
ZINC000058631354
PDBe Ligand
C0E
PDB Entries
2rhw

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 Solubility0.0155 mg/mLALOGPS
logP1.52ALOGPS
logP1.64Chemaxon
logS-4.2ALOGPS
pKa (Strongest Acidic)2.81Chemaxon
pKa (Strongest Basic)-7.2Chemaxon
Physiological Charge-1Chemaxon
Hydrogen Acceptor Count4Chemaxon
Hydrogen Donor Count2Chemaxon
Polar Surface Area74.6 Å2Chemaxon
Rotatable Bond Count4Chemaxon
Refractivity61.05 m3·mol-1Chemaxon
Polarizability21.39 Å3Chemaxon
Number of Rings1Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.8716
Blood Brain Barrier+0.8502
Caco-2 permeable-0.5077
P-glycoprotein substrateNon-substrate0.6427
P-glycoprotein inhibitor INon-inhibitor0.9417
P-glycoprotein inhibitor IINon-inhibitor0.9921
Renal organic cation transporterNon-inhibitor0.9443
CYP450 2C9 substrateNon-substrate0.8879
CYP450 2D6 substrateNon-substrate0.9217
CYP450 3A4 substrateNon-substrate0.7252
CYP450 1A2 substrateNon-inhibitor0.6553
CYP450 2C9 inhibitorNon-inhibitor0.8768
CYP450 2D6 inhibitorNon-inhibitor0.8994
CYP450 2C19 inhibitorNon-inhibitor0.9017
CYP450 3A4 inhibitorNon-inhibitor0.852
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9694
Ames testNon AMES toxic0.8509
CarcinogenicityNon-carcinogens0.7624
BiodegradationNot ready biodegradable0.8551
Rat acute toxicity2.0360 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9814
hERG inhibition (predictor II)Non-inhibitor0.9476
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-MSsplash10-059l-8890000000-4f6ad7d09226b5b075d5
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0a59-1980000000-cedf381bce4f28264369
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-004r-0910000000-dcdb431d42c5d1ce9548
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-00kr-9400000000-c52affdf20926ed051be
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-03di-0900000000-097f55d8934a59503ac0
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-05fr-1900000000-4a0c6f6a134828e7cfb7
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0292-4900000000-3de735732dc9a290a5b5
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]-163.49278
predicted
DeepCCS 1.0 (2019)
[M+H]+165.85118
predicted
DeepCCS 1.0 (2019)
[M+Na]+171.94434
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. 2-hydroxy-6-oxo-6-phenylhexa-2,4-dienoate hydrolase
Kind
Protein
Organism
Burkholderia xenovorans (strain LB400)
Pharmacological action
Unknown
General Function
2-hydroxy-6-oxonona-2,4-dienedioate hydrolase activity
Specific Function
Catalyzes an unusual C-C bond hydrolysis of 2-hydroxy-6-oxo-6-phenylhexa-2,4-dienoic acid (HOPDA) to produce benzoic acid and 2-hydroxy-2,4-pentadienoic acid (HPD).
Gene Name
bphD
Uniprot ID
P47229
Uniprot Name
2-hydroxy-6-oxo-6-phenylhexa-2,4-dienoate hydrolase
Molecular Weight
32029.435 Da
References
  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [Article]

Drug created at September 15, 2010 21:23 / Updated at June 12, 2020 16:52