Identification
NameN-({(2S,3S)-3-[(BENZYLAMINO)CARBONYL]OXIRAN-2-YL}CARBONYL)-L-ISOLEUCYL-L-PROLINE
Accession NumberDB07231
TypeSmall Molecule
GroupsExperimental
DescriptionNot Available
Structure
Thumb
SynonymsNot Available
External IDs Not Available
Product Ingredients Not Available
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International BrandsNot Available
Brand mixturesNot Available
CategoriesNot Available
UNIINot Available
CAS numberNot Available
WeightAverage: 431.4822
Monoisotopic: 431.205635675
Chemical FormulaC22H29N3O6
InChI KeyMERYMLLGRCNRKE-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][C@](C)(CC)[C@]([H])(NC(=O)[C@@]1([H])O[C@]1([H])C(=O)NCC1=CC=CC=C1)C(=O)N1CCC[C@@]1([H])C(O)=O
Pharmacology
IndicationNot Available
Structured Indications Not Available
PharmacodynamicsNot Available
Mechanism of action
TargetKindPharmacological actionActionsOrganismUniProt ID
Cathepsin BProteinunknownNot AvailableHumanP07858 details
Related Articles
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organismsNot Available
PathwaysNot Available
Pharmacogenomic Effects/ADRs Not Available
Interactions
Drug Interactions Not Available
Food InteractionsNot Available
References
Synthesis ReferenceNot Available
General ReferencesNot Available
External Links
ATC CodesNot Available
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Clinical Trials
Clinical Trials Not Available
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental PropertiesNot 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
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as dipeptides. These are organic compounds containing a sequence of exactly two alpha-amino acids joined by a peptide bond.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganic acids and derivatives
Sub ClassCarboxylic acids and derivatives
Direct ParentDipeptides
Alternative ParentsIsoleucine 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
SubstituentsAlpha-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
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot 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 June 11, 2017 21:06