(2S)-1-[(2S,4R)-4-Benzyl-2-hydroxy-5-{[(1S,2R,5S)-2-hydroxy-5-methylcyclopentyl]amino}-5-oxopentyl]-4-{[6-chloro-5-(4-methyl-1-piperazinyl)-2-pyrazinyl]carbonyl}-N-(2-methyl-2-propanyl)-2-piperazineca rboxamide

Identification

Generic Name
(2S)-1-[(2S,4R)-4-Benzyl-2-hydroxy-5-{[(1S,2R,5S)-2-hydroxy-5-methylcyclopentyl]amino}-5-oxopentyl]-4-{[6-chloro-5-(4-methyl-1-piperazinyl)-2-pyrazinyl]carbonyl}-N-(2-methyl-2-propanyl)-2-piperazineca rboxamide
DrugBank Accession Number
DB02785
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
Weight
Average: 727.336
Monoisotopic: 726.398394617
Chemical Formula
C37H55ClN8O5
Synonyms
Not Available

Pharmacology

Indication

Not Available

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Contraindications & Blackbox Warnings
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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UGag-Pol polyproteinNot Available
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 alpha amino acid amides. These are amide derivatives of alpha amino acids.
Kingdom
Organic compounds
Super Class
Organic acids and derivatives
Class
Carboxylic acids and derivatives
Sub Class
Amino acids, peptides, and analogues
Direct Parent
Alpha amino acid amides
Alternative Parents
N-arylpiperazines / Piperazine carboxamides / Pyrazinecarboxamides / Dialkylarylamines / 2-heteroaryl carboxamides / Aralkylamines / N-methylpiperazines / Aminopyrazines / Aryl chlorides / Cyclopentanols
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Substituents
1,2-aminoalcohol / 1,4-diazinane / 2-heteroaryl carboxamide / Alcohol / Alpha-amino acid amide / Amine / Aminopyrazine / Aralkylamine / Aromatic heteromonocyclic compound / Aryl chloride
show 37 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
pyrazines, piperazinecarboxamide (CHEBI:47109)
Affected organisms
Not Available

Chemical Identifiers

UNII
Not Available
CAS number
Not Available
InChI Key
SQZXWXXIPWXBCL-CYTJBAGBSA-N
InChI
InChI=1S/C37H55ClN8O5/c1-24-11-12-30(48)31(24)41-34(49)26(19-25-9-7-6-8-10-25)20-27(47)22-45-17-18-46(23-29(45)35(50)42-37(2,3)4)36(51)28-21-39-33(32(38)40-28)44-15-13-43(5)14-16-44/h6-10,21,24,26-27,29-31,47-48H,11-20,22-23H2,1-5H3,(H,41,49)(H,42,50)/t24-,26+,27-,29-,30+,31-/m0/s1
IUPAC Name
(2S)-1-[(2S,4R)-4-benzyl-2-hydroxy-4-{[(1S,2R,5S)-2-hydroxy-5-methylcyclopentyl]carbamoyl}butyl]-N-tert-butyl-4-[6-chloro-5-(4-methylpiperazin-1-yl)pyrazine-2-carbonyl]piperazine-2-carboxamide
SMILES
[H]N([C@H]1[C@@H](C)CC[C@H]1O)C(=O)[C@@H](C[C@H](O)CN1CCN(C[C@H]1C(=O)N([H])C(C)(C)C)C(=O)C1=CN=C(N2CCN(C)CC2)C(Cl)=N1)CC1=CC=CC=C1

References

General References
Not Available
PubChem Compound
444756
PubChem Substance
46508413
ChemSpider
392588
ZINC
ZINC000024447263
PDBe Ligand
3IN
PDB Entries
1c6x / 2bpy / 2bpz

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 Solubility0.104 mg/mLALOGPS
logP2.61ALOGPS
logP2.16ChemAxon
logS-3.8ALOGPS
pKa (Strongest Acidic)14.14ChemAxon
pKa (Strongest Basic)6.42ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count10ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area154.47 Å2ChemAxon
Rotatable Bond Count12ChemAxon
Refractivity199.04 m3·mol-1ChemAxon
Polarizability80.36 Å3ChemAxon
Number of Rings5ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.8967
Blood Brain Barrier-0.9864
Caco-2 permeable-0.6196
P-glycoprotein substrateSubstrate0.9026
P-glycoprotein inhibitor IInhibitor0.5435
P-glycoprotein inhibitor IIInhibitor0.704
Renal organic cation transporterNon-inhibitor0.8582
CYP450 2C9 substrateNon-substrate0.7694
CYP450 2D6 substrateNon-substrate0.7465
CYP450 3A4 substrateSubstrate0.7757
CYP450 1A2 substrateNon-inhibitor0.8774
CYP450 2C9 inhibitorNon-inhibitor0.6507
CYP450 2D6 inhibitorNon-inhibitor0.7655
CYP450 2C19 inhibitorNon-inhibitor0.6856
CYP450 3A4 inhibitorNon-inhibitor0.6327
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9124
Ames testNon AMES toxic0.6966
CarcinogenicityNon-carcinogens0.8295
BiodegradationNot ready biodegradable1.0
Rat acute toxicity2.7992 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9693
hERG inhibition (predictor II)Inhibitor0.7334
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/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Targets

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Kind
Protein
Organism
Not Available
Pharmacological action
Unknown
General Function
Zinc ion binding
Specific Function
Gag-Pol polyprotein: Mediates, with Gag polyrotein, the essential events in virion assembly, including binding the plasma membrane, making the protein-protein interactions necessary to create spher...
Gene Name
gag-pol
Uniprot ID
P03366
Uniprot Name
Gag-Pol polyprotein
Molecular Weight
163287.51 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