4-Amino-N-{4-[2-(2,6-Dimethyl-Phenoxy)-Acetylamino]-3-Hydroxy-1-Isobutyl-5-Phenyl-Pentyl}-Benzamide

Identification

Generic Name
4-Amino-N-{4-[2-(2,6-Dimethyl-Phenoxy)-Acetylamino]-3-Hydroxy-1-Isobutyl-5-Phenyl-Pentyl}-Benzamide
DrugBank Accession Number
DB04373
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
Weight
Average: 531.6856
Monoisotopic: 531.309706815
Chemical Formula
C32H41N3O4
Synonyms
Not Available

Pharmacology

Indication

Not Available

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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UPlasmepsin-2Not AvailablePlasmodium falciparum
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 amphetamines and derivatives. These are organic compounds containing or derived from 1-phenylpropan-2-amine.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Benzene and substituted derivatives
Sub Class
Phenethylamines
Direct Parent
Amphetamines and derivatives
Alternative Parents
Aminobenzamides / Benzamides / m-Xylenes / Phenoxy compounds / Phenol ethers / Aniline and substituted anilines / Benzoyl derivatives / Alkyl aryl ethers / Secondary carboxylic acid amides / Secondary alcohols
show 6 more
Substituents
Alcohol / Alkyl aryl ether / Amine / Amino acid or derivatives / Aminobenzamide / Aminobenzoic acid or derivatives / Amphetamine or derivatives / Aniline or substituted anilines / Aromatic homomonocyclic compound / Benzamide
show 20 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
WQUBEIMCFHCJCO-AWCRTANDSA-N
InChI
InChI=1S/C32H41N3O4/c1-21(2)16-27(34-32(38)25-14-9-15-26(33)18-25)19-29(36)28(17-24-12-6-5-7-13-24)35-30(37)20-39-31-22(3)10-8-11-23(31)4/h5-15,18,21,27-29,36H,16-17,19-20,33H2,1-4H3,(H,34,38)(H,35,37)/t27-,28-,29-/m0/s1
IUPAC Name
N-[(2S,3S,5S)-5-[(3-aminophenyl)formamido]-3-hydroxy-7-methyl-1-phenyloctan-2-yl]-2-(2,6-dimethylphenoxy)acetamide
SMILES
CC(C)C[C@@H](C[C@H](O)[C@H](CC1=CC=CC=C1)NC(=O)COC1=C(C)C=CC=C1C)NC(=O)C1=CC=CC(N)=C1

References

General References
Not Available
PubChem Compound
446912
PubChem Substance
46505068
ChemSpider
394146
ZINC
ZINC000015658067
PDBe Ligand
R36
PDB Entries
1lee

Clinical Trials

Clinical Trials
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PhaseStatusPurposeConditionsCountStart DateWhy Stopped100+ additional columns

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 Solubility0.000377 mg/mLALOGPS
logP4.14ALOGPS
logP4.96Chemaxon
logS-6.2ALOGPS
pKa (Strongest Acidic)13.5Chemaxon
pKa (Strongest Basic)3.26Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count5Chemaxon
Hydrogen Donor Count4Chemaxon
Polar Surface Area113.68 Å2Chemaxon
Rotatable Bond Count13Chemaxon
Refractivity156.13 m3·mol-1Chemaxon
Polarizability59.66 Å3Chemaxon
Number of Rings3Chemaxon
Bioavailability0Chemaxon
Rule of FiveNoChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleYesChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.5813
Blood Brain Barrier-0.9618
Caco-2 permeable-0.7777
P-glycoprotein substrateSubstrate0.6607
P-glycoprotein inhibitor INon-inhibitor0.6657
P-glycoprotein inhibitor IIInhibitor0.5272
Renal organic cation transporterNon-inhibitor0.9458
CYP450 2C9 substrateNon-substrate0.7739
CYP450 2D6 substrateNon-substrate0.791
CYP450 3A4 substrateSubstrate0.6511
CYP450 1A2 substrateNon-inhibitor0.7927
CYP450 2C9 inhibitorNon-inhibitor0.7804
CYP450 2D6 inhibitorNon-inhibitor0.8784
CYP450 2C19 inhibitorNon-inhibitor0.7148
CYP450 3A4 inhibitorNon-inhibitor0.6646
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.7953
Ames testNon AMES toxic0.7935
CarcinogenicityNon-carcinogens0.8865
BiodegradationNot ready biodegradable0.9911
Rat acute toxicity2.3747 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9939
hERG inhibition (predictor II)Non-inhibitor0.6144
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, Negative (Annotated)Predicted LC-MS/MSsplash10-0ap0-0495500000-8c5d9b7416fb001518d3
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-03e9-0947530000-42b0a9d94eea0ee2f7e0
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0006-6938110000-34b2a4f88eaf3ce26fe5
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0a59-0923130000-10feeb4f3697905b55b1
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-05fr-2911000000-e2f09b4ffe41c7f81a8d
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0apl-2934020000-8d1049762665cb9cf83e
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-228.1089
predicted
DeepCCS 1.0 (2019)
[M+H]+229.93379
predicted
DeepCCS 1.0 (2019)
[M+Na]+235.57095
predicted
DeepCCS 1.0 (2019)

Targets

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Kind
Protein
Organism
Plasmodium falciparum
Pharmacological action
Unknown
General Function
Aspartic-type endopeptidase activity
Specific Function
Not Available
Gene Name
Not Available
Uniprot ID
P46925
Uniprot Name
Plasmepsin-2
Molecular Weight
51489.41 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