NAV

N-(2-AMINOETHYL)-2-{3-CHLORO-4-[(4-ISOPROPYLBENZYL)OXY]PHENYL} ACETAMIDE

Identification

Generic Name
N-(2-AMINOETHYL)-2-{3-CHLORO-4-[(4-ISOPROPYLBENZYL)OXY]PHENYL} ACETAMIDE
DrugBank Accession Number
DB08610
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 360.878
Monoisotopic: 360.160455761
Chemical Formula
C20H25ClN2O2
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
U[Pyruvate dehydrogenase [lipoamide]] kinase isozyme 2, mitochondrialNot AvailableHumans
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 aromatic monoterpenoids. These are monoterpenoids containing at least one aromatic ring.
Kingdom
Organic compounds
Super Class
Lipids and lipid-like molecules
Class
Prenol lipids
Sub Class
Monoterpenoids
Direct Parent
Aromatic monoterpenoids
Alternative Parents
Phenylacetamides / Monocyclic monoterpenoids / Cumenes / Phenylpropanes / Phenoxy compounds / Phenol ethers / Alkyl aryl ethers / Chlorobenzenes / Aryl chlorides / Secondary carboxylic acid amides
show 7 more
Substituents
Alkyl aryl ether / Amine / Amino acid or derivatives / Aromatic homomonocyclic compound / Aromatic monoterpenoid / Aryl chloride / Aryl halide / Benzenoid / Carbonyl group / Carboxamide group
show 24 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
DFXJYVQAAFOZDP-UHFFFAOYSA-N
InChI
InChI=1S/C20H25ClN2O2/c1-14(2)17-6-3-15(4-7-17)13-25-19-8-5-16(11-18(19)21)12-20(24)23-10-9-22/h3-8,11,14H,9-10,12-13,22H2,1-2H3,(H,23,24)
IUPAC Name
N-(2-aminoethyl)-2-(3-chloro-4-{[4-(propan-2-yl)phenyl]methoxy}phenyl)acetamide
SMILES
CC(C)C1=CC=C(COC2=C(Cl)C=C(CC(=O)NCCN)C=C2)C=C1

References

General References
Not Available
PubChem Compound
6102763
PubChem Substance
99445081
ChemSpider
4810271
ZINC
ZINC000016051834
PDBe Ligand
TF3
PDB Entries
2bu7 / 4v25 / 4v26 / 5m4k / 5m4m / 5m4n / 5m4p / 6tmp / 6tmq / 6tmz …
show 2 more

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 Solubility0.000419 mg/mLALOGPS
logP3.58ALOGPS
logP3.65Chemaxon
logS-5.9ALOGPS
pKa (Strongest Acidic)14.94Chemaxon
pKa (Strongest Basic)9.16Chemaxon
Physiological Charge1Chemaxon
Hydrogen Acceptor Count3Chemaxon
Hydrogen Donor Count2Chemaxon
Polar Surface Area64.35 Å2Chemaxon
Rotatable Bond Count8Chemaxon
Refractivity102.11 m3·mol-1Chemaxon
Polarizability40.66 Å3Chemaxon
Number of Rings2Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9885
Blood Brain Barrier+0.8264
Caco-2 permeable+0.5773
P-glycoprotein substrateSubstrate0.7419
P-glycoprotein inhibitor INon-inhibitor0.5446
P-glycoprotein inhibitor IINon-inhibitor0.9565
Renal organic cation transporterNon-inhibitor0.6641
CYP450 2C9 substrateNon-substrate0.8729
CYP450 2D6 substrateNon-substrate0.5845
CYP450 3A4 substrateSubstrate0.6065
CYP450 1A2 substrateInhibitor0.8071
CYP450 2C9 inhibitorInhibitor0.5
CYP450 2D6 inhibitorInhibitor0.5265
CYP450 2C19 inhibitorInhibitor0.8628
CYP450 3A4 inhibitorInhibitor0.55
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.7032
Ames testNon AMES toxic0.6399
CarcinogenicityNon-carcinogens0.7085
BiodegradationNot ready biodegradable0.9965
Rat acute toxicity2.4805 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9048
hERG inhibition (predictor II)Inhibitor0.7672
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 MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-03dl-3109000000-95affd70c2817c9ae9d3
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0k96-0349000000-9486df0cf4695a573e95
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-014i-0920000000-9c90cc236a12b84472fc
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0006-9105000000-728421d3aed2a3e7d155
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-000x-3930000000-0a97dedc5ed70e387b52
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0006-9721000000-cc1eddebc428b9655ef6
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]-183.99898
predicted
DeepCCS 1.0 (2019)
[M+H]+186.37105
predicted
DeepCCS 1.0 (2019)
[M+Na]+193.65765
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. [Pyruvate dehydrogenase [lipoamide]] kinase isozyme 2, mitochondrial
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Pyruvate dehydrogenase (acetyl-transferring) kinase activity
Specific Function
Kinase that plays a key role in the regulation of glucose and fatty acid metabolism and homeostasis via phosphorylation of the pyruvate dehydrogenase subunits PDHA1 and PDHA2. This inhibits pyruvat...
Gene Name
PDK2
Uniprot ID
Q15119
Uniprot Name
[Pyruvate dehydrogenase (acetyl-transferring)] kinase isozyme 2, mitochondrial
Molecular Weight
46153.39 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 21:33 / Updated at June 12, 2020 16:52