NAV

2-(2,4-DICHLOROPHENOXY)-5-(PYRIDIN-2-YLMETHYL)PHENOL

Identification

Generic Name
2-(2,4-DICHLOROPHENOXY)-5-(PYRIDIN-2-YLMETHYL)PHENOL
DrugBank Accession Number
DB07287
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 346.207
Monoisotopic: 345.032334079
Chemical Formula
C18H13Cl2NO2
Synonyms
Not Available
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Pharmacology

Indication

Not Available

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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UEnoyl-[acyl-carrier-protein] reductase [NADH]Not AvailableMycobacterium tuberculosis
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 diphenylethers. These are aromatic compounds containing two benzene rings linked to each other through an ether group.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Benzene and substituted derivatives
Sub Class
Diphenylethers
Direct Parent
Diphenylethers
Alternative Parents
Diarylethers / Phenoxy compounds / Phenol ethers / Dichlorobenzenes / 1-hydroxy-4-unsubstituted benzenoids / 1-hydroxy-2-unsubstituted benzenoids / Pyridines and derivatives / Aryl chlorides / Heteroaromatic compounds / Azacyclic compounds
show 4 more
Substituents
1,3-dichlorobenzene / 1-hydroxy-2-unsubstituted benzenoid / 1-hydroxy-4-unsubstituted benzenoid / Aromatic heteromonocyclic compound / Aryl chloride / Aryl halide / Azacycle / Chlorobenzene / Diaryl ether / Diphenylether
show 16 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
Not Available
CAS number
Not Available
InChI Key
AOVDSWPGWPRTSR-UHFFFAOYSA-N
InChI
InChI=1S/C18H13Cl2NO2/c19-13-5-7-17(15(20)11-13)23-18-6-4-12(10-16(18)22)9-14-3-1-2-8-21-14/h1-8,10-11,22H,9H2
IUPAC Name
2-(2,4-dichlorophenoxy)-5-[(pyridin-2-yl)methyl]phenol
SMILES
OC1=CC(CC2=CC=CC=N2)=CC=C1OC1=CC=C(Cl)C=C1Cl

References

General References
Not Available
PubChem Compound
16220130
PubChem Substance
99443758
ChemSpider
17347434
BindingDB
25425
ChEMBL
CHEMBL260585
ZINC
ZINC000029060814
PDBe Ligand
8PC
PDB Entries
2op1 / 3fne

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 Solubility0.00524 mg/mLALOGPS
logP5.69ALOGPS
logP5.13Chemaxon
logS-4.8ALOGPS
pKa (Strongest Acidic)8.41Chemaxon
pKa (Strongest Basic)4.86Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count2Chemaxon
Hydrogen Donor Count1Chemaxon
Polar Surface Area42.35 Å2Chemaxon
Rotatable Bond Count4Chemaxon
Refractivity91.05 m3·mol-1Chemaxon
Polarizability34.13 Å3Chemaxon
Number of Rings3Chemaxon
Bioavailability1Chemaxon
Rule of FiveNoChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9735
Blood Brain Barrier+0.9917
Caco-2 permeable+0.6851
P-glycoprotein substrateNon-substrate0.693
P-glycoprotein inhibitor INon-inhibitor0.8845
P-glycoprotein inhibitor IINon-inhibitor0.8859
Renal organic cation transporterNon-inhibitor0.6087
CYP450 2C9 substrateNon-substrate0.7506
CYP450 2D6 substrateNon-substrate0.7173
CYP450 3A4 substrateNon-substrate0.5445
CYP450 1A2 substrateInhibitor0.676
CYP450 2C9 inhibitorNon-inhibitor0.6263
CYP450 2D6 inhibitorInhibitor0.5166
CYP450 2C19 inhibitorInhibitor0.6862
CYP450 3A4 inhibitorNon-inhibitor0.6026
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.8237
Ames testNon AMES toxic0.8622
CarcinogenicityNon-carcinogens0.916
BiodegradationNot ready biodegradable0.9704
Rat acute toxicity2.4696 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8983
hERG inhibition (predictor II)Non-inhibitor0.7883
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-MSsplash10-0002-2956000000-df60dd66d44c21c00ee7
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0002-0009000000-2a5c6e18cd758d7ee28e
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0006-0009000000-03c14cbc8ca0024ac393
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0002-0019000000-91408258c73492f67e2b
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-001i-9001000000-f419385b7c723d126c5c
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-00rl-2694000000-be0849590f52bfcf60ed
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-001i-9000000000-7eec4adaaa50b1fe9ced
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]-164.98415
predicted
DeepCCS 1.0 (2019)
[M+H]+167.34215
predicted
DeepCCS 1.0 (2019)
[M+Na]+173.4572
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. Enoyl-[acyl-carrier-protein] reductase [NADH]
Kind
Protein
Organism
Mycobacterium tuberculosis
Pharmacological action
Unknown
General Function
Enoyl-ACP reductase of the type II fatty acid syntase (FAS-II) system, which is involved in the biosynthesis of mycolic acids, a major component of mycobacterial cell walls (PubMed:25227413). Catalyzes the NADH-dependent reduction of the double bond of 2-trans-enoyl-[acyl-carrier protein], an essential step in the fatty acid elongation cycle of the FAS-II pathway (PubMed:7599116). Shows preference for long-chain fatty acyl thioester substrates (>C16), and can also use 2-trans-enoyl-CoAs as alternative substrates (PubMed:7599116). The mycobacterial FAS-II system utilizes the products of the FAS-I system as primers to extend fatty acyl chain lengths up to C56, forming the meromycolate chain that serves as the precursor for final mycolic acids (PubMed:25227413).
Specific Function
Enoyl-[acyl-carrier-protein] reductase (nadh) activity
Gene Name
inhA
Uniprot ID
P9WGR1
Uniprot Name
Enoyl-[acyl-carrier-protein] reductase [NADH]
Molecular Weight
28527.55 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 21:20 / Updated at June 12, 2020 16:52