1-[3,3-Dimethyl-2-(2-Methylamino-Propionylamino)-Butyryl]-Pyrrolidine-2-Carboxylic Acid(1,2,3,4-Tetrahydro-Naphthalen-1-Yl)-Amide

Identification

Name
1-[3,3-Dimethyl-2-(2-Methylamino-Propionylamino)-Butyryl]-Pyrrolidine-2-Carboxylic Acid(1,2,3,4-Tetrahydro-Naphthalen-1-Yl)-Amide
Accession Number
DB02628  (EXPT00351)
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: 442.5942
Monoisotopic: 442.294391102
Chemical Formula
C25H38N4O3
InChI Key
JUJIMRZGUBTJRV-NASSWSRMSA-N
InChI
InChI=1S/C25H38N4O3/c1-16(26-5)22(30)28-21(25(2,3)4)24(32)29-15-9-14-20(29)23(31)27-19-13-8-11-17-10-6-7-12-18(17)19/h6-7,10,12,16,19-21,26H,8-9,11,13-15H2,1-5H3,(H,27,31)(H,28,30)/t16-,19+,20-,21+/m0/s1
IUPAC Name
(2S)-1-[(2S)-3,3-dimethyl-2-[(2S)-2-(methylamino)propanamido]butanoyl]-N-[(1R)-1,2,3,4-tetrahydronaphthalen-1-yl]pyrrolidine-2-carboxamide
SMILES
[H][[email protected]@](C)(NC)C(=O)N[[email protected]]([H])(C(=O)N1CCC[[email protected]@]1([H])C(=O)N[[email protected]]1([H])CCCC2=C1C=CC=C2)C(C)(C)C

Pharmacology

Indication
Not Available
Structured Indications
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UE3 ubiquitin-protein ligase XIAPNot 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
4369343
PubChem Substance
46505788
ChemSpider
3571936
BindingDB
13166
ChEMBL
CHEMBL1230662
HET
998
PDB Entries
1tfq

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 Solubility0.0362 mg/mLALOGPS
logP2.26ALOGPS
logP2.45ChemAxon
logS-4.1ALOGPS
pKa (Strongest Acidic)12.54ChemAxon
pKa (Strongest Basic)8.6ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area90.54 Å2ChemAxon
Rotatable Bond Count7ChemAxon
Refractivity124.46 m3·mol-1ChemAxon
Polarizability49.19 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9712
Blood Brain Barrier-0.5165
Caco-2 permeable-0.656
P-glycoprotein substrateSubstrate0.8632
P-glycoprotein inhibitor IInhibitor0.7805
P-glycoprotein inhibitor IIInhibitor0.5214
Renal organic cation transporterNon-inhibitor0.8152
CYP450 2C9 substrateNon-substrate0.7932
CYP450 2D6 substrateNon-substrate0.6971
CYP450 3A4 substrateSubstrate0.7544
CYP450 1A2 substrateNon-inhibitor0.8199
CYP450 2C9 inhibitorNon-inhibitor0.6244
CYP450 2D6 inhibitorNon-inhibitor0.8006
CYP450 2C19 inhibitorInhibitor0.6523
CYP450 3A4 inhibitorInhibitor0.6963
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.5263
Ames testNon AMES toxic0.8209
CarcinogenicityNon-carcinogens0.8876
BiodegradationNot ready biodegradable0.9763
Rat acute toxicity2.5115 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9857
hERG inhibition (predictor II)Inhibitor0.684
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 oligopeptides. These are organic compounds containing a sequence of between three and ten alpha-amino acids joined by peptide bonds.
Kingdom
Organic compounds
Super Class
Organic acids and derivatives
Class
Carboxylic acids and derivatives
Sub Class
Amino acids, peptides, and analogues
Direct Parent
Oligopeptides
Alternative Parents
Valine and derivatives / Proline and derivatives / N-acyl-alpha amino acids and derivatives / Alpha amino acid amides / Alanine and derivatives / Tetralins / Pyrrolidinecarboxamides / N-acylpyrrolidines / Tertiary carboxylic acid amides / Secondary carboxylic acid amides
show 6 more
Substituents
Alpha-oligopeptide / Valine or derivatives / Proline or derivatives / N-acyl-alpha amino acid or derivatives / Alpha-amino acid amide / Alanine or derivatives / N-substituted-alpha-amino acid / Alpha-amino acid or derivatives / Tetralin / Pyrrolidine-2-carboxamide
show 22 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available

Targets

Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Zinc ion binding
Specific Function
Multi-functional protein which regulates not only caspases and apoptosis, but also modulates inflammatory signaling and immunity, copper homeostasis, mitogenic kinase signaling, cell proliferation,...
Gene Name
XIAP
Uniprot ID
P98170
Uniprot Name
E3 ubiquitin-protein ligase XIAP
Molecular Weight
56684.41 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. [PubMed:17139284]
  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. [PubMed:17016423]
  3. 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 December 01, 2017 15:00