3-{[(5R,6R)-5-Benzyl-6-hydroxy-2,4-bis(4-hydroxybenzyl)-3-oxo-1,2,4-triazepan-1-yl]sulfonyl}benzonitril

Identification

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Name
3-{[(5R,6R)-5-Benzyl-6-hydroxy-2,4-bis(4-hydroxybenzyl)-3-oxo-1,2,4-triazepan-1-yl]sulfonyl}benzonitril
Accession Number
DB03141  (EXPT00690)
Type
Small Molecule
Groups
Experimental
Description
Not Available
Structure
Thumb
Synonyms
Not Available
Categories
Not Available
UNII
Not Available
CAS number
Not Available
Weight
Average: 598.669
Monoisotopic: 598.188605402
Chemical Formula
C32H30N4O6S
InChI Key
UYUWNNRWESUYOB-FIRIVFDPSA-N
InChI
InChI=1S/C32H30N4O6S/c33-19-26-7-4-8-29(17-26)43(41,42)36-22-31(39)30(18-23-5-2-1-3-6-23)34(20-24-9-13-27(37)14-10-24)32(40)35(36)21-25-11-15-28(38)16-12-25/h1-17,30-31,37-39H,18,20-22H2/t30-,31-/m1/s1
IUPAC Name
3-{[(5R,6R)-5-benzyl-6-hydroxy-2,4-bis[(4-hydroxyphenyl)methyl]-3-oxo-1,2,4-triazepan-1-yl]sulfonyl}benzonitrile
SMILES
O[C@@H]1CN(N(CC2=CC=C(O)C=C2)C(=O)N(CC2=CC=C(O)C=C2)[C@@H]1CC1=CC=CC=C1)S(=O)(=O)C1=CC(=CC=C1)C#N

Pharmacology

Indication
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UGag-Pol polyproteinNot Available
UV-1 proteaseNot AvailableHuman immunodeficiency virus 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
Toxicity
Not Available
Affected organisms
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

References

General References
Not Available
External Links
PubChem Compound
448667
PubChem Substance
46508567
ChemSpider
395395
ChEMBL
CHEMBL362811
ZINC
ZINC000014880632
HET
BH0
PDB Entries
1t7k

Clinical Trials

Clinical Trials
Not Available

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 Solubility0.0141 mg/mLALOGPS
logP3.57ALOGPS
logP4.52ChemAxon
logS-4.6ALOGPS
pKa (Strongest Acidic)9.19ChemAxon
pKa (Strongest Basic)-3.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area145.41 Å2ChemAxon
Rotatable Bond Count7ChemAxon
Refractivity161.29 m3·mol-1ChemAxon
Polarizability61.17 Å3ChemAxon
Number of Rings5ChemAxon
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.7904
Blood Brain Barrier-0.7802
Caco-2 permeable-0.6495
P-glycoprotein substrateSubstrate0.5633
P-glycoprotein inhibitor IInhibitor0.546
P-glycoprotein inhibitor IINon-inhibitor0.7937
Renal organic cation transporterNon-inhibitor0.7553
CYP450 2C9 substrateNon-substrate0.6231
CYP450 2D6 substrateNon-substrate0.8042
CYP450 3A4 substrateNon-substrate0.545
CYP450 1A2 substrateNon-inhibitor0.8043
CYP450 2C9 inhibitorNon-inhibitor0.6949
CYP450 2D6 inhibitorNon-inhibitor0.8496
CYP450 2C19 inhibitorNon-inhibitor0.6987
CYP450 3A4 inhibitorInhibitor0.6708
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9341
Ames testNon AMES toxic0.6048
CarcinogenicityNon-carcinogens0.6467
BiodegradationNot ready biodegradable0.9615
Rat acute toxicity2.4974 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.857
hERG inhibition (predictor II)Non-inhibitor0.5826
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

Taxonomy

Description
This compound belongs to the class of organic compounds known as benzenesulfonamides. These are organic compounds containing a sulfonamide group that is S-linked to a benzene ring.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Benzene and substituted derivatives
Sub Class
Benzenesulfonamides
Direct Parent
Benzenesulfonamides
Alternative Parents
Benzenesulfonyl compounds / Benzonitriles / 1-hydroxy-2-unsubstituted benzenoids / Sulfonyls / Semicarbazides / Organosulfonic acids and derivatives / Secondary alcohols / Organic carbonic acids and derivatives / Nitriles / Azacyclic compounds
show 4 more
Substituents
Benzenesulfonamide / Benzenesulfonyl group / Benzonitrile / 1-hydroxy-2-unsubstituted benzenoid / Phenol / Semicarbazide / Organic sulfonic acid or derivatives / Sulfonyl / Organosulfonic acid or derivatives / Carbonic acid derivative
show 16 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
Not Available

Targets

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. [PubMed:17139284]
  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. [PubMed:17016423]
Kind
Protein
Organism
Human immunodeficiency virus 1
Pharmacological action
Unknown
General Function
Aspartic-type endopeptidase activity
Specific Function
Not Available
Gene Name
ORF
Uniprot ID
Q9Q2G8
Uniprot Name
V-1 protease
Molecular Weight
10792.72 Da
References
  1. Huang PP, Randolph JT, Klein LL, Vasavanonda S, Dekhtyar T, Stoll VS, Kempf DJ: Synthesis and antiviral activity of P1' arylsulfonamide azacyclic urea HIV protease inhibitors. Bioorg Med Chem Lett. 2004 Aug 2;14(15):4075-8. [PubMed:15225729]

Drug created on June 13, 2005 07:24 / Updated on February 06, 2020 11:40