NAV

2-{HYDROXY[2-NITRO-4-(TRIFLUOROMETHYL)PHENYL]METHYLENE}CYCLOHEXANE-1,3-DIONE

Identification

Generic Name
2-{HYDROXY[2-NITRO-4-(TRIFLUOROMETHYL)PHENYL]METHYLENE}CYCLOHEXANE-1,3-DIONE
DrugBank Accession Number
DB08307
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 329.2281
Monoisotopic: 329.05110705
Chemical Formula
C14H10F3NO5
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
U4-hydroxyphenylpyruvate dioxygenaseNot AvailableStreptomyces avermitilis (strain ATCC 31267 / DSM 46492 / JCM 5070 / NCIMB 12804 / NRRL 8165 / MA-4680)
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 trifluoromethylbenzenes. These are organofluorine compounds that contain a benzene ring substituted with one or more trifluoromethyl groups.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Benzene and substituted derivatives
Sub Class
Trifluoromethylbenzenes
Direct Parent
Trifluoromethylbenzenes
Alternative Parents
Nitrobenzenes / Nitroaromatic compounds / Vinylogous acids / Cyclic ketones / Propargyl-type 1,3-dipolar organic compounds / Organic oxoazanium compounds / Enols / Organopnictogen compounds / Organonitrogen compounds / Organofluorides
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Substituents
Alkyl fluoride / Alkyl halide / Allyl-type 1,3-dipolar organic compound / Aromatic homomonocyclic compound / C-nitro compound / Carbonyl group / Cyclic ketone / Enol / Hydrocarbon derivative / Ketone
show 16 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
PMHVFNYNPNKNRO-UHFFFAOYSA-N
InChI
InChI=1S/C14H10F3NO5/c15-14(16,17)7-4-5-8(9(6-7)18(22)23)13(21)12-10(19)2-1-3-11(12)20/h4-6,21H,1-3H2
IUPAC Name
2-{hydroxy[2-nitro-4-(trifluoromethyl)phenyl]methylidene}cyclohexane-1,3-dione
SMILES
OC(C1=CC=C(C=C1[N+]([O-])=O)C(F)(F)F)=C1C(=O)CCCC1=O

References

General References
Not Available
PubChem Compound
5289053
PubChem Substance
99444778
ChemSpider
4451094
ChEMBL
CHEMBL23996
ZINC
ZINC000013473744
PDBe Ligand
NTD
PDB Entries
1t47 / 5ywi / 6j63 / 8im2

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 Solubility0.00755 mg/mLALOGPS
logP1.75ALOGPS
logP2.94Chemaxon
logS-4.6ALOGPS
pKa (Strongest Acidic)4.01Chemaxon
pKa (Strongest Basic)-7.6Chemaxon
Physiological Charge-1Chemaxon
Hydrogen Acceptor Count5Chemaxon
Hydrogen Donor Count1Chemaxon
Polar Surface Area97.51 Å2Chemaxon
Rotatable Bond Count3Chemaxon
Refractivity73.27 m3·mol-1Chemaxon
Polarizability27.01 Å3Chemaxon
Number of Rings2Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9742
Blood Brain Barrier+0.5131
Caco-2 permeable-0.5342
P-glycoprotein substrateNon-substrate0.7481
P-glycoprotein inhibitor IInhibitor0.6533
P-glycoprotein inhibitor IINon-inhibitor0.8467
Renal organic cation transporterNon-inhibitor0.8316
CYP450 2C9 substrateNon-substrate0.7502
CYP450 2D6 substrateNon-substrate0.828
CYP450 3A4 substrateSubstrate0.5909
CYP450 1A2 substrateNon-inhibitor0.6951
CYP450 2C9 inhibitorNon-inhibitor0.6534
CYP450 2D6 inhibitorNon-inhibitor0.8973
CYP450 2C19 inhibitorNon-inhibitor0.6781
CYP450 3A4 inhibitorNon-inhibitor0.5737
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.5226
Ames testNon AMES toxic0.6136
CarcinogenicityNon-carcinogens0.6935
BiodegradationNot ready biodegradable0.9687
Rat acute toxicity2.6526 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.5692
hERG inhibition (predictor II)Non-inhibitor0.7982
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-MSsplash10-0296-5595000000-93fb5c362c29d8c4da31
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]-144.27045
predicted
DeepCCS 1.0 (2019)
[M+H]+147.19803
predicted
DeepCCS 1.0 (2019)
[M+Na]+155.58311
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. 4-hydroxyphenylpyruvate dioxygenase
Kind
Protein
Organism
Streptomyces avermitilis (strain ATCC 31267 / DSM 46492 / JCM 5070 / NCIMB 12804 / NRRL 8165 / MA-4680)
Pharmacological action
Unknown
General Function
Metal ion binding
Specific Function
Not Available
Gene Name
hpd
Uniprot ID
Q53586
Uniprot Name
4-hydroxyphenylpyruvate dioxygenase
Molecular Weight
41862.91 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 21:30 / Updated at June 12, 2020 16:52