N-(3-Propylcarbamoyloxirane-2-Carbonyl)-Isoleucyl-Proline

Identification

Name
N-(3-Propylcarbamoyloxirane-2-Carbonyl)-Isoleucyl-Proline
Accession Number
DB02855  (EXPT00003)
Type
Small Molecule
Groups
Experimental
Description
Not Available
Structure
Thumb
Synonyms
  • N-(3-Propylcarbamoyloxirane-2-carbonyl)-isoleucyl-proline
Categories
UNII
Not Available
CAS number
134448-10-5
Weight
Average: 385.4552
Monoisotopic: 385.221285739
Chemical Formula
C18H31N3O6
InChI Key
UDNIFTKCMDIXFC-ABHRYQDASA-N
InChI
InChI=1S/C18H31N3O6/c1-4-8-19-16(24)13(22)10-14(23)20-15(11(3)5-2)17(25)21-9-6-7-12(21)18(26)27/h11-13,15,22H,4-10H2,1-3H3,(H,19,24)(H,20,23)(H,26,27)/t11-,12-,13-,15-/m0/s1
IUPAC Name
(2S)-1-[(2S,3S)-2-[(3S)-3-hydroxy-3-(propylcarbamoyl)propanamido]-3-methylpentanoyl]pyrrolidine-2-carboxylic acid
SMILES
[H][C@](O)(CC(=O)N[C@]([H])(C(=O)N1CCC[C@@]1([H])C(O)=O)[C@@]([H])(C)CC)C(=O)NCCC

Pharmacology

Indication
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
DrugInteractionDrug group
AbacavirThe serum concentration of Abacavir can be decreased when it is combined with N-(3-Propylcarbamoyloxirane-2-Carbonyl)-Isoleucyl-Proline.Approved, Investigational
AlfuzosinThe serum concentration of Alfuzosin can be increased when it is combined with N-(3-Propylcarbamoyloxirane-2-Carbonyl)-Isoleucyl-Proline.Approved, Investigational
AlprazolamThe serum concentration of Alprazolam can be increased when it is combined with N-(3-Propylcarbamoyloxirane-2-Carbonyl)-Isoleucyl-Proline.Approved, Illicit, Investigational
Ambroxol acefyllinateThe serum concentration of Ambroxol acefyllinate can be decreased when it is combined with N-(3-Propylcarbamoyloxirane-2-Carbonyl)-Isoleucyl-Proline.Experimental, Investigational
AmineptineThe serum concentration of Amineptine can be increased when it is combined with N-(3-Propylcarbamoyloxirane-2-Carbonyl)-Isoleucyl-Proline.Illicit, Withdrawn
AminophyllineThe serum concentration of Aminophylline can be decreased when it is combined with N-(3-Propylcarbamoyloxirane-2-Carbonyl)-Isoleucyl-Proline.Approved
AmitriptylineThe serum concentration of Amitriptyline can be increased when it is combined with N-(3-Propylcarbamoyloxirane-2-Carbonyl)-Isoleucyl-Proline.Approved
AmitriptylinoxideThe serum concentration of Amitriptylinoxide can be increased when it is combined with N-(3-Propylcarbamoyloxirane-2-Carbonyl)-Isoleucyl-Proline.Approved, Investigational
AmoxapineThe serum concentration of Amoxapine can be increased when it is combined with N-(3-Propylcarbamoyloxirane-2-Carbonyl)-Isoleucyl-Proline.Approved
BoceprevirThe serum concentration of N-(3-Propylcarbamoyloxirane-2-Carbonyl)-Isoleucyl-Proline can be decreased when it is combined with Boceprevir.Approved, Withdrawn
BromocriptineThe serum concentration of Bromocriptine can be increased when it is combined with N-(3-Propylcarbamoyloxirane-2-Carbonyl)-Isoleucyl-Proline.Approved, Investigational
ButriptylineThe serum concentration of Butriptyline can be increased when it is combined with N-(3-Propylcarbamoyloxirane-2-Carbonyl)-Isoleucyl-Proline.Approved
CabergolineThe serum concentration of Cabergoline can be increased when it is combined with N-(3-Propylcarbamoyloxirane-2-Carbonyl)-Isoleucyl-Proline.Approved
CarbamazepineThe metabolism of N-(3-Propylcarbamoyloxirane-2-Carbonyl)-Isoleucyl-Proline can be increased when combined with Carbamazepine.Approved, Investigational
ClarithromycinThe therapeutic efficacy of Clarithromycin can be decreased when used in combination with N-(3-Propylcarbamoyloxirane-2-Carbonyl)-Isoleucyl-Proline.Approved
ClomipramineThe serum concentration of Clomipramine can be increased when it is combined with N-(3-Propylcarbamoyloxirane-2-Carbonyl)-Isoleucyl-Proline.Approved, Investigational, Vet Approved
CyclophosphamideThe risk or severity of adverse effects can be increased when N-(3-Propylcarbamoyloxirane-2-Carbonyl)-Isoleucyl-Proline is combined with Cyclophosphamide.Approved, Investigational
CyclosporineThe serum concentration of Cyclosporine can be increased when it is combined with N-(3-Propylcarbamoyloxirane-2-Carbonyl)-Isoleucyl-Proline.Approved, Investigational, Vet Approved
DelavirdineThe serum concentration of Delavirdine can be decreased when it is combined with N-(3-Propylcarbamoyloxirane-2-Carbonyl)-Isoleucyl-Proline.Approved
DesipramineThe serum concentration of Desipramine can be increased when it is combined with N-(3-Propylcarbamoyloxirane-2-Carbonyl)-Isoleucyl-Proline.Approved, Investigational
DibenzepinThe serum concentration of Dibenzepin can be increased when it is combined with N-(3-Propylcarbamoyloxirane-2-Carbonyl)-Isoleucyl-Proline.Experimental
DiethylstilbestrolThe serum concentration of Diethylstilbestrol can be decreased when it is combined with N-(3-Propylcarbamoyloxirane-2-Carbonyl)-Isoleucyl-Proline.Approved, Investigational
DigoxinThe serum concentration of Digoxin can be increased when it is combined with N-(3-Propylcarbamoyloxirane-2-Carbonyl)-Isoleucyl-Proline.Approved
DihydroergotamineThe serum concentration of Dihydroergotamine can be increased when it is combined with N-(3-Propylcarbamoyloxirane-2-Carbonyl)-Isoleucyl-Proline.Approved, Investigational
DiltiazemThe metabolism of Diltiazem can be decreased when combined with N-(3-Propylcarbamoyloxirane-2-Carbonyl)-Isoleucyl-Proline.Approved, Investigational
DimetacrineThe serum concentration of Dimetacrine can be increased when it is combined with N-(3-Propylcarbamoyloxirane-2-Carbonyl)-Isoleucyl-Proline.Approved, Withdrawn
DosulepinThe serum concentration of Dosulepin can be increased when it is combined with N-(3-Propylcarbamoyloxirane-2-Carbonyl)-Isoleucyl-Proline.Approved
DoxepinThe serum concentration of Doxepin can be increased when it is combined with N-(3-Propylcarbamoyloxirane-2-Carbonyl)-Isoleucyl-Proline.Approved, Investigational
DyphyllineThe serum concentration of Dyphylline can be decreased when it is combined with N-(3-Propylcarbamoyloxirane-2-Carbonyl)-Isoleucyl-Proline.Approved
EnfuvirtideThe serum concentration of Enfuvirtide can be increased when it is combined with N-(3-Propylcarbamoyloxirane-2-Carbonyl)-Isoleucyl-Proline.Approved, Investigational
Ergoloid mesylateThe serum concentration of Ergoloid mesylate can be increased when it is combined with N-(3-Propylcarbamoyloxirane-2-Carbonyl)-Isoleucyl-Proline.Approved
ErgonovineThe serum concentration of Ergonovine can be increased when it is combined with N-(3-Propylcarbamoyloxirane-2-Carbonyl)-Isoleucyl-Proline.Approved
ErgotamineThe serum concentration of Ergotamine can be increased when it is combined with N-(3-Propylcarbamoyloxirane-2-Carbonyl)-Isoleucyl-Proline.Approved
EstradiolThe serum concentration of Estradiol can be decreased when it is combined with N-(3-Propylcarbamoyloxirane-2-Carbonyl)-Isoleucyl-Proline.Approved, Investigational, Vet Approved
Estradiol cypionateThe serum concentration of Estradiol cypionate can be decreased when it is combined with N-(3-Propylcarbamoyloxirane-2-Carbonyl)-Isoleucyl-Proline.Approved, Investigational, Vet Approved
Estradiol valerateThe serum concentration of Estradiol valerate can be decreased when it is combined with N-(3-Propylcarbamoyloxirane-2-Carbonyl)-Isoleucyl-Proline.Approved, Investigational, Vet Approved
Ethinyl EstradiolThe serum concentration of Ethinyl Estradiol can be decreased when it is combined with N-(3-Propylcarbamoyloxirane-2-Carbonyl)-Isoleucyl-Proline.Approved
EtravirineThe serum concentration of Etravirine can be decreased when it is combined with N-(3-Propylcarbamoyloxirane-2-Carbonyl)-Isoleucyl-Proline.Approved
GarlicThe serum concentration of N-(3-Propylcarbamoyloxirane-2-Carbonyl)-Isoleucyl-Proline can be decreased when it is combined with Garlic.Approved, Nutraceutical
ImipramineThe serum concentration of Imipramine can be increased when it is combined with N-(3-Propylcarbamoyloxirane-2-Carbonyl)-Isoleucyl-Proline.Approved
IprindoleThe serum concentration of Iprindole can be increased when it is combined with N-(3-Propylcarbamoyloxirane-2-Carbonyl)-Isoleucyl-Proline.Experimental
LofepramineThe serum concentration of Lofepramine can be increased when it is combined with N-(3-Propylcarbamoyloxirane-2-Carbonyl)-Isoleucyl-Proline.Experimental
LovastatinThe serum concentration of Lovastatin can be increased when it is combined with N-(3-Propylcarbamoyloxirane-2-Carbonyl)-Isoleucyl-Proline.Approved, Investigational
MelitracenThe serum concentration of Melitracen can be increased when it is combined with N-(3-Propylcarbamoyloxirane-2-Carbonyl)-Isoleucyl-Proline.Experimental, Investigational
MestranolThe serum concentration of Mestranol can be decreased when it is combined with N-(3-Propylcarbamoyloxirane-2-Carbonyl)-Isoleucyl-Proline.Approved
MethylergometrineThe serum concentration of Methylergometrine can be increased when it is combined with N-(3-Propylcarbamoyloxirane-2-Carbonyl)-Isoleucyl-Proline.Approved
MidazolamThe serum concentration of Midazolam can be increased when it is combined with N-(3-Propylcarbamoyloxirane-2-Carbonyl)-Isoleucyl-Proline.Approved, Illicit
NefazodoneThe serum concentration of Nefazodone can be increased when it is combined with N-(3-Propylcarbamoyloxirane-2-Carbonyl)-Isoleucyl-Proline.Approved, Withdrawn
NortriptylineThe serum concentration of Nortriptyline can be increased when it is combined with N-(3-Propylcarbamoyloxirane-2-Carbonyl)-Isoleucyl-Proline.Approved
OpipramolThe serum concentration of Opipramol can be increased when it is combined with N-(3-Propylcarbamoyloxirane-2-Carbonyl)-Isoleucyl-Proline.Investigational
PethidineThe risk or severity of adverse effects can be increased when N-(3-Propylcarbamoyloxirane-2-Carbonyl)-Isoleucyl-Proline is combined with Pethidine.Approved
ProtriptylineThe serum concentration of Protriptyline can be increased when it is combined with N-(3-Propylcarbamoyloxirane-2-Carbonyl)-Isoleucyl-Proline.Approved
RiociguatThe serum concentration of Riociguat can be increased when it is combined with N-(3-Propylcarbamoyloxirane-2-Carbonyl)-Isoleucyl-Proline.Approved
SildenafilThe serum concentration of Sildenafil can be increased when it is combined with N-(3-Propylcarbamoyloxirane-2-Carbonyl)-Isoleucyl-Proline.Approved, Investigational
SimvastatinThe serum concentration of Simvastatin can be increased when it is combined with N-(3-Propylcarbamoyloxirane-2-Carbonyl)-Isoleucyl-Proline.Approved
St. John's WortThe metabolism of N-(3-Propylcarbamoyloxirane-2-Carbonyl)-Isoleucyl-Proline can be increased when combined with St. John's Wort.Approved, Investigational, Nutraceutical
TacrolimusThe metabolism of Tacrolimus can be decreased when combined with N-(3-Propylcarbamoyloxirane-2-Carbonyl)-Isoleucyl-Proline.Approved, Investigational
TemsirolimusThe risk or severity of adverse effects can be increased when N-(3-Propylcarbamoyloxirane-2-Carbonyl)-Isoleucyl-Proline is combined with Temsirolimus.Approved
TheophyllineThe serum concentration of Theophylline can be decreased when it is combined with N-(3-Propylcarbamoyloxirane-2-Carbonyl)-Isoleucyl-Proline.Approved
TianeptineThe serum concentration of Tianeptine can be increased when it is combined with N-(3-Propylcarbamoyloxirane-2-Carbonyl)-Isoleucyl-Proline.Approved, Investigational
TipranavirThe serum concentration of N-(3-Propylcarbamoyloxirane-2-Carbonyl)-Isoleucyl-Proline can be decreased when it is combined with Tipranavir.Approved, Investigational
TriazolamThe serum concentration of Triazolam can be increased when it is combined with N-(3-Propylcarbamoyloxirane-2-Carbonyl)-Isoleucyl-Proline.Approved, Investigational
TrimipramineThe serum concentration of Trimipramine can be increased when it is combined with N-(3-Propylcarbamoyloxirane-2-Carbonyl)-Isoleucyl-Proline.Approved
Valproic AcidThe serum concentration of Valproic Acid can be decreased when it is combined with N-(3-Propylcarbamoyloxirane-2-Carbonyl)-Isoleucyl-Proline.Approved, Investigational
VerapamilThe metabolism of Verapamil can be decreased when combined with N-(3-Propylcarbamoyloxirane-2-Carbonyl)-Isoleucyl-Proline.Approved
ZidovudineThe serum concentration of Zidovudine can be decreased when it is combined with N-(3-Propylcarbamoyloxirane-2-Carbonyl)-Isoleucyl-Proline.Approved
Food Interactions
Not Available

References

General References
Not Available
External Links
PubChem Compound
5287408
PubChem Substance
46507264
ChemSpider
4449798
HET
074
PDB Entries
1qdq / 3hhi / 3qsd

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 Solubility8.23 mg/mLALOGPS
logP0.09ALOGPS
logP-0.29ChemAxon
logS-1.7ALOGPS
pKa (Strongest Acidic)3.86ChemAxon
pKa (Strongest Basic)-2.3ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area136.04 Å2ChemAxon
Rotatable Bond Count10ChemAxon
Refractivity96.75 m3·mol-1ChemAxon
Polarizability40.28 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.5678
Blood Brain Barrier-0.9544
Caco-2 permeable-0.7898
P-glycoprotein substrateSubstrate0.7076
P-glycoprotein inhibitor INon-inhibitor0.5984
P-glycoprotein inhibitor IINon-inhibitor0.7219
Renal organic cation transporterNon-inhibitor0.9514
CYP450 2C9 substrateNon-substrate0.8775
CYP450 2D6 substrateNon-substrate0.7866
CYP450 3A4 substrateNon-substrate0.5146
CYP450 1A2 substrateNon-inhibitor0.9156
CYP450 2C9 inhibitorNon-inhibitor0.9309
CYP450 2D6 inhibitorNon-inhibitor0.9377
CYP450 2C19 inhibitorNon-inhibitor0.8735
CYP450 3A4 inhibitorNon-inhibitor0.9222
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9619
Ames testNon AMES toxic0.8874
CarcinogenicityNon-carcinogens0.8791
BiodegradationNot ready biodegradable0.7085
Rat acute toxicity2.5003 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9715
hERG inhibition (predictor II)Non-inhibitor0.8615
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 / N-acyl-L-alpha-amino acids / Proline and derivatives / Alpha amino acid amides / N-acylpyrrolidines / Pyrrolidine carboxylic acids / N-acyl amines / Tertiary carboxylic acid amides / Secondary alcohols / Secondary carboxylic acid amides
show 8 more
Substituents
Alpha-dipeptide / Isoleucine or derivatives / N-acyl-alpha-amino acid / N-acyl-alpha amino acid or derivatives / Proline or derivatives / N-acyl-l-alpha-amino acid / Alpha-amino acid amide / Alpha-amino acid or derivatives / N-acylpyrrolidine / Pyrrolidine carboxylic acid
show 23 more
Molecular Framework
Aliphatic heteromonocyclic compounds
External Descriptors
Not Available

Targets

Details
1. Cathepsin B
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 June 13, 2005 07:24 / Updated on June 02, 2018 07:08