NAV

2-(11-{2-[Benzenesulfonyl-(3-Methyl-Butyl)-Amino]-1-Hydroxy-Ethyl}-6,9-Dioxo-2-Oxa-7,10-Diaza-Bicyclo[11.2.2]Heptadeca-1(16),13(17),14-Trien-8-Yl)-Acetamide, Inhibitor 2

Identification

Generic Name
2-(11-{2-[Benzenesulfonyl-(3-Methyl-Butyl)-Amino]-1-Hydroxy-Ethyl}-6,9-Dioxo-2-Oxa-7,10-Diaza-Bicyclo[11.2.2]Heptadeca-1(16),13(17),14-Trien-8-Yl)-Acetamide, Inhibitor 2
DrugBank Accession Number
DB02411
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 588.715
Monoisotopic: 588.261770344
Chemical Formula
C29H40N4O7S
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
UGag-Pol polyproteinNot AvailableHIV-1
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 macrolactams. These are cyclic amides of amino carboxylic acids, having a 1-azacycloalkan-2-one structure, or analogues having unsaturation or heteroatoms replacing one or more carbon atoms of the ring. They are nitrogen analogues (the a nitrogen atom replacing the o atom of the cyclic carboxylic acid group ) of the naturally occurring macrolides.
Kingdom
Organic compounds
Super Class
Phenylpropanoids and polyketides
Class
Macrolactams
Sub Class
Not Available
Direct Parent
Macrolactams
Alternative Parents
Alpha amino acids and derivatives / Benzenesulfonamides / Benzenesulfonyl compounds / Alkyl aryl ethers / Organosulfonamides / Aminosulfonyl compounds / Lactams / Primary carboxylic acid amides / Secondary alcohols / Secondary carboxylic acid amides
show 7 more
Substituents
Alcohol / Alkyl aryl ether / Alpha-amino acid or derivatives / Aminosulfonyl compound / Aromatic heteropolycyclic compound / Azacycle / Benzenesulfonamide / Benzenesulfonyl group / Benzenoid / Carbonyl group
show 23 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
Not Available
CAS number
Not Available
InChI Key
HOUHLOFMBSYNBO-KKUQBAQOSA-N
InChI
InChI=1S/C29H40N4O7S/c1-20(2)14-15-33(41(38,39)23-7-4-3-5-8-23)19-26(34)24-17-21-10-12-22(13-11-21)40-16-6-9-28(36)31-25(18-27(30)35)29(37)32-24/h3-5,7-8,10-13,20,24-26,34H,6,9,14-19H2,1-2H3,(H2,30,35)(H,31,36)(H,32,37)/t24-,25-,26+/m0/s1
IUPAC Name
2-[(8S,11S)-11-[(1R)-1-hydroxy-2-[N-(3-methylbutyl)benzenesulfonamido]ethyl]-6,9-dioxo-2-oxa-7,10-diazabicyclo[11.2.2]heptadeca-1(15),13,16-trien-8-yl]acetamide
SMILES
CC(C)CCN(C[C@@H](O)[C@@H]1CC2=CC=C(OCCCC(=O)N[C@@H](CC(N)=O)C(=O)N1)C=C2)S(=O)(=O)C1=CC=CC=C1

References

General References
Not Available
PubChem Compound
466959
PubChem Substance
46506982
ChemSpider
410366
BindingDB
13928
ChEMBL
CHEMBL1233239
ZINC
ZINC000014880333
PDBe Ligand
HBH
PDB Entries
1z1r

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 Solubility0.0814 mg/mLALOGPS
logP1.8ALOGPS
logP1.19Chemaxon
logS-3.9ALOGPS
pKa (Strongest Acidic)10.74Chemaxon
pKa (Strongest Basic)-1.7Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count7Chemaxon
Hydrogen Donor Count4Chemaxon
Polar Surface Area168.13 Å2Chemaxon
Rotatable Bond Count9Chemaxon
Refractivity153.34 m3·mol-1Chemaxon
Polarizability61.17 Å3Chemaxon
Number of Rings3Chemaxon
Bioavailability1Chemaxon
Rule of FiveNoChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleYesChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9626
Blood Brain Barrier-0.928
Caco-2 permeable-0.6453
P-glycoprotein substrateSubstrate0.8584
P-glycoprotein inhibitor IInhibitor0.512
P-glycoprotein inhibitor IINon-inhibitor0.9367
Renal organic cation transporterNon-inhibitor0.8854
CYP450 2C9 substrateNon-substrate0.6542
CYP450 2D6 substrateNon-substrate0.7249
CYP450 3A4 substrateSubstrate0.5947
CYP450 1A2 substrateNon-inhibitor0.879
CYP450 2C9 inhibitorNon-inhibitor0.7117
CYP450 2D6 inhibitorNon-inhibitor0.8807
CYP450 2C19 inhibitorNon-inhibitor0.814
CYP450 3A4 inhibitorNon-inhibitor0.5767
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9423
Ames testNon AMES toxic0.6501
CarcinogenicityNon-carcinogens0.7014
BiodegradationNot ready biodegradable0.9737
Rat acute toxicity2.4568 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9543
hERG inhibition (predictor II)Non-inhibitor0.6102
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/MSsplash10-000j-0200390000-beff9fee428b936a1db7
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-000i-0010090000-845def043112be83b836
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0006-2802090000-ce380fcf7b1755f7855e
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0006-1931040000-e1f0f4012ac95633a8a7
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0v04-9304100000-f37ac251cfde6c5cca1b
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0006-3963100000-056cd15f0cb7e32640b2
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-226.27776
predicted
DeepCCS 1.0 (2019)
[M+H]+228.10265
predicted
DeepCCS 1.0 (2019)
[M+Na]+233.70847
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. Gag-Pol polyprotein
Kind
Protein
Organism
HIV-1
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
P03369
Uniprot Name
Gag-Pol polyprotein
Molecular Weight
162014.15 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 July 02, 2020 13:16