NAV

4-Nitrophenyl (3S)-3-({N-[(benzyloxy)carbonyl]-L-phenylalanyl}amino)-5-phenyl-1-pentanesulfonate

Identification

Generic Name
4-Nitrophenyl (3S)-3-({N-[(benzyloxy)carbonyl]-L-phenylalanyl}amino)-5-phenyl-1-pentanesulfonate
DrugBank Accession Number
DB02051
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
Similar Structures
Weight
Average: 645.722
Monoisotopic: 645.214485801
Chemical Formula
C34H35N3O8S
Synonyms
  • 3-[N-[Benzyloxycarbonyl]-phenylalaninyl-amino]-5-phenyl-pentane-1-sulfonic acid 4-nitro-phenyl ester
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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
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
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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 phenylalanine and derivatives. These are compounds containing phenylalanine or a derivative thereof resulting from reaction of phenylalanine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.
Kingdom
Organic compounds
Super Class
Organic acids and derivatives
Class
Carboxylic acids and derivatives
Sub Class
Amino acids, peptides, and analogues
Direct Parent
Phenylalanine and derivatives
Alternative Parents
Alpha amino acid amides / Amphetamines and derivatives / Benzyloxycarbonyls / Nitrobenzenes / Nitroaromatic compounds / Phenoxy compounds / Sulfonic acid esters / Fatty amides / Organosulfonic acid esters / Sulfonyls
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Substituents
Allyl-type 1,3-dipolar organic compound / Alpha-amino acid amide / Amphetamine or derivatives / Aromatic homomonocyclic compound / Benzenoid / Benzyloxycarbonyl / C-nitro compound / Carbamic acid ester / Carbonyl group / Carboxamide group
show 26 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
WABCRPSWXFHXDH-NYDCQLBNSA-N
InChI
InChI=1S/C34H35N3O8S/c38-33(32(24-27-12-6-2-7-13-27)36-34(39)44-25-28-14-8-3-9-15-28)35-29(17-16-26-10-4-1-5-11-26)22-23-46(42,43)45-31-20-18-30(19-21-31)37(40)41/h1-15,18-21,29,32H,16-17,22-25H2,(H,35,38)(H,36,39)/t29-,32-/m0/s1
IUPAC Name
benzyl N-[(1S)-1-{[(3S)-1-[(4-nitrophenoxy)sulfonyl]-5-phenylpentan-3-yl]carbamoyl}-2-phenylethyl]carbamate
SMILES
[H]N([C@@H](CC1=CC=CC=C1)C(=O)N([H])[C@@H](CCC1=CC=CC=C1)CCS(=O)(=O)OC1=CC=C(C=C1)[N+]([O-])=O)C(=O)OCC1=CC=CC=C1

References

General References
Not Available
PubChem Compound
5289561
PubChem Substance
46505415
ChemSpider
4451499
ZINC
ZINC000024531121
PDBe Ligand
VS3
PDB Entries
1f2b

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 Solubility0.000118 mg/mLALOGPS
logP4.61ALOGPS
logP6.23Chemaxon
logS-6.7ALOGPS
pKa (Strongest Acidic)13.1Chemaxon
pKa (Strongest Basic)-3.6Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count6Chemaxon
Hydrogen Donor Count2Chemaxon
Polar Surface Area153.94 Å2Chemaxon
Rotatable Bond Count17Chemaxon
Refractivity171.29 m3·mol-1Chemaxon
Polarizability67.8 Å3Chemaxon
Number of Rings4Chemaxon
Bioavailability0Chemaxon
Rule of FiveNoChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleYesChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.855
Blood Brain Barrier+0.8151
Caco-2 permeable-0.6003
P-glycoprotein substrateNon-substrate0.5331
P-glycoprotein inhibitor IInhibitor0.6121
P-glycoprotein inhibitor IINon-inhibitor0.8631
Renal organic cation transporterNon-inhibitor0.8828
CYP450 2C9 substrateNon-substrate0.8358
CYP450 2D6 substrateNon-substrate0.7997
CYP450 3A4 substrateSubstrate0.5514
CYP450 1A2 substrateNon-inhibitor0.6471
CYP450 2C9 inhibitorNon-inhibitor0.5937
CYP450 2D6 inhibitorNon-inhibitor0.8139
CYP450 2C19 inhibitorNon-inhibitor0.5053
CYP450 3A4 inhibitorNon-inhibitor0.8994
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.6137
Ames testNon AMES toxic0.5176
CarcinogenicityNon-carcinogens0.5213
BiodegradationNot ready biodegradable0.7786
Rat acute toxicity2.6179 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.5208
hERG inhibition (predictor II)Non-inhibitor0.5408
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
Not Available
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-231.91566
predicted
DeepCCS 1.0 (2019)
[M+H]+233.74057
predicted
DeepCCS 1.0 (2019)
[M+Na]+239.37009
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. Cruzipain
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 at June 13, 2005 13:24 / Updated at June 12, 2020 16:52