4-Methyl-N-[(2S)-1-oxo-3-phenyl-1-[[(3S)-1-phenyl-5-(phenylmethoxysulfamoyl)pentan-3-yl]amino]propan-2-yl]piperazine-1-carboxamide

Identification

Generic Name
4-Methyl-N-[(2S)-1-oxo-3-phenyl-1-[[(3S)-1-phenyl-5-(phenylmethoxysulfamoyl)pentan-3-yl]amino]propan-2-yl]piperazine-1-carboxamide
DrugBank Accession Number
DB04427
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
Thumb
Weight
Average: 621.79
Monoisotopic: 621.298490201
Chemical Formula
C33H43N5O5S
Synonyms
  • N-{(3S)-1-[(Benzyloxy)sulfamoyl]-5-phenyl-3-pentanyl}-Nα-[(4-methyl-1-piperazinyl)carbonyl]-L-phenylalaninamide

Pharmacology

Indication

Not Available

Pharmacology
Reduce drug development failure rates
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Contraindications & Blackbox Warnings
Contraindications
Avoid life-threatening adverse drug events
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Avoid life-threatening adverse drug events & improve clinical decision support.
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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UCruzipainNot AvailableTrypanosoma cruzi
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
Adverseeffects
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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
Classification
Not classified
Affected organisms
Not Available

Chemical Identifiers

UNII
Not Available
CAS number
Not Available
InChI Key
PPIYQXGSPPWVLJ-CONSDPRKSA-N
InChI
InChI=1S/C33H43N5O5S/c1-37-20-22-38(23-21-37)33(40)35-31(25-28-13-7-3-8-14-28)32(39)34-30(18-17-27-11-5-2-6-12-27)19-24-44(41,42)36-43-26-29-15-9-4-10-16-29/h2-16,30-31,36H,17-26H2,1H3,(H,34,39)(H,35,40)/t30-,31-/m0/s1
IUPAC Name
(2S)-N-[(3S)-1-[(benzyloxy)sulfamoyl]-5-phenylpentan-3-yl]-2-[(4-methylpiperazine-1-carbonyl)amino]-3-phenylpropanamide
SMILES
[H]N(OCC1=CC=CC=C1)S(=O)(=O)CC[C@H](CCC1=CC=CC=C1)N([H])C(=O)[C@H](CC1=CC=CC=C1)N([H])C(=O)N1CCN(C)CC1

References

General References
Not Available
PubChem Compound
5289562
PubChem Substance
46504570
ChemSpider
4451500
ZINC
ZINC000014881206
PDBe Ligand
VS4
PDB Entries
1f2c / 5ogr

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 Solubility0.008 mg/mLALOGPS
logP3.51ALOGPS
logP3.4ChemAxon
logS-4.9ALOGPS
pKa (Strongest Acidic)10.09ChemAxon
pKa (Strongest Basic)7.02ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area120.08 Å2ChemAxon
Rotatable Bond Count14ChemAxon
Refractivity171.38 m3·mol-1ChemAxon
Polarizability68.27 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9647
Blood Brain Barrier+0.6867
Caco-2 permeable-0.6768
P-glycoprotein substrateSubstrate0.8967
P-glycoprotein inhibitor IInhibitor0.7998
P-glycoprotein inhibitor IINon-inhibitor0.9937
Renal organic cation transporterNon-inhibitor0.8426
CYP450 2C9 substrateNon-substrate0.7287
CYP450 2D6 substrateNon-substrate0.7835
CYP450 3A4 substrateSubstrate0.549
CYP450 1A2 substrateNon-inhibitor0.8315
CYP450 2C9 inhibitorNon-inhibitor0.7602
CYP450 2D6 inhibitorNon-inhibitor0.9012
CYP450 2C19 inhibitorNon-inhibitor0.8071
CYP450 3A4 inhibitorNon-inhibitor0.8043
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9692
Ames testNon AMES toxic0.5845
CarcinogenicityNon-carcinogens0.8485
BiodegradationNot ready biodegradable0.9306
Rat acute toxicity2.5684 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.7787
hERG inhibition (predictor II)Inhibitor0.6126
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

Drugtargets2
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Kind
Protein
Organism
Trypanosoma cruzi
Pharmacological action
Unknown
General Function
Cysteine-type endopeptidase activity
Specific Function
Hydrolyzes chromogenic peptides at the carboxyl Arg or Lys; requires at least one more amino acid, preferably Arg, Phe, Val or Leu, between the terminal Arg or Lys and the amino-blocking group.The ...
Gene Name
Not Available
Uniprot ID
P25779
Uniprot Name
Cruzipain
Molecular Weight
49835.59 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 on June 13, 2005 13:24 / Updated on June 12, 2020 16:52