N-({(2S,3S)-3-[(BENZYLAMINO)CARBONYL]OXIRAN-2-YL}CARBONYL)-L-ISOLEUCYL-L-PROLINE

Identification

Name
N-({(2S,3S)-3-[(BENZYLAMINO)CARBONYL]OXIRAN-2-YL}CARBONYL)-L-ISOLEUCYL-L-PROLINE
Accession Number
DB07231
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: 431.4822
Monoisotopic: 431.205635675
Chemical Formula
C22H29N3O6
InChI Key
MERYMLLGRCNRKE-HILJTLORSA-N
InChI
InChI=1S/C22H29N3O6/c1-3-13(2)16(21(28)25-11-7-10-15(25)22(29)30)24-20(27)18-17(31-18)19(26)23-12-14-8-5-4-6-9-14/h4-6,8-9,13,15-18H,3,7,10-12H2,1-2H3,(H,23,26)(H,24,27)(H,29,30)/t13-,15-,16-,17-,18-/m0/s1
IUPAC Name
(2S)-1-[(2S,3S)-2-{[(2S,3S)-3-(benzylcarbamoyl)oxiran-2-yl]formamido}-3-methylpentanoyl]pyrrolidine-2-carboxylic acid
SMILES
[H][[email protected]](C)(CC)[[email protected]]([H])(NC(=O)[[email protected]@]1([H])O[[email protected]]1([H])C(=O)NCC1=CC=CC=C1)C(=O)N1CCC[[email protected]@]1([H])C(O)=O

Pharmacology

Indication
Not Available
Structured Indications
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UCathepsin BNot AvailableHuman
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
Not Available
Food Interactions
Not Available

References

General References
Not Available
External Links
PubChem Compound
23647361
PubChem Substance
99443702
ChemSpider
25056628
BindingDB
16502
HET
78A
PDB Entries
2dcd

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 Solubility0.484 mg/mLALOGPS
logP1.31ALOGPS
logP1.01ChemAxon
logS-3ALOGPS
pKa (Strongest Acidic)3.81ChemAxon
pKa (Strongest Basic)-3.3ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area128.34 Å2ChemAxon
Rotatable Bond Count9ChemAxon
Refractivity109.92 m3·mol-1ChemAxon
Polarizability44.52 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9288
Blood Brain Barrier-0.9044
Caco-2 permeable-0.7253
P-glycoprotein substrateSubstrate0.7049
P-glycoprotein inhibitor INon-inhibitor0.8812
P-glycoprotein inhibitor IINon-inhibitor0.9225
Renal organic cation transporterNon-inhibitor0.9093
CYP450 2C9 substrateNon-substrate0.8601
CYP450 2D6 substrateNon-substrate0.8191
CYP450 3A4 substrateNon-substrate0.6059
CYP450 1A2 substrateNon-inhibitor0.8292
CYP450 2C9 inhibitorNon-inhibitor0.8171
CYP450 2D6 inhibitorNon-inhibitor0.8997
CYP450 2C19 inhibitorNon-inhibitor0.6292
CYP450 3A4 inhibitorNon-inhibitor0.7247
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.7994
Ames testNon AMES toxic0.6913
CarcinogenicityNon-carcinogens0.879
BiodegradationNot ready biodegradable0.947
Rat acute toxicity2.3331 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9791
hERG inhibition (predictor II)Non-inhibitor0.8844
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 dipeptides. These are organic compounds containing a sequence of exactly two alpha-amino acids joined by a peptide bond.
Kingdom
Organic compounds
Super Class
Organic acids and derivatives
Class
Carboxylic acids and derivatives
Sub Class
Amino acids, peptides, and analogues
Direct Parent
Dipeptides
Alternative Parents
Isoleucine and derivatives / Proline and derivatives / N-acyl-L-alpha-amino acids / Alpha amino acid amides / Pyrrolidine carboxylic acids / N-acylpyrrolidines / Benzene and substituted derivatives / Oxirane carboxylic acids and derivatives / Tertiary carboxylic acid amides / Secondary carboxylic acid amides
show 10 more
Substituents
Alpha-dipeptide / Isoleucine or derivatives / Proline or derivatives / N-acyl-alpha-amino acid / N-acyl-l-alpha-amino acid / N-acyl-alpha amino acid or derivatives / Alpha-amino acid amide / Alpha-amino acid or derivatives / Pyrrolidine carboxylic acid / N-acylpyrrolidine
show 25 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
Not Available

Targets

Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Proteoglycan binding
Specific Function
Thiol protease which is believed to participate in intracellular degradation and turnover of proteins. Has also been implicated in tumor invasion and metastasis.
Gene Name
CTSB
Uniprot ID
P07858
Uniprot Name
Cathepsin B
Molecular Weight
37821.35 Da
References
  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235]

Drug created on September 15, 2010 15:19 / Updated on December 01, 2017 15:48