iPPI-DB

Inhibitors of Protein-Protein Interaction Database

Compound 1181

Identifiers

  • Canonical SMILES: 
    CC[C@H](NC)C(=O)N[C@H]1CCCC[C@H]2CC[C@H](N2C1=O)C(=O)NC(c1ccccc1)c1ccccc1
  • IUPAC name: 
    (3S,6S,10aS)-N-benzhydryl-6-[[(2S)-2-(methylamino)butanoyl]amino]-5-oxo-2,3,6,7,8,9,10,10a-octahydro-1H-pyrrolo[1,2-a]azocine-3-carboxamide
  • InChi: 
    InChI=1S/C29H38N4O3/c1-3-23(30-2)27(34)31-24-17-11-10-16-22-18-19-25(33(22)29(24)36)28(35)32-26(20-12-6-4-7-13-20)21-14-8-5-9-15-21/h4-9,12-15,22-26,30H,3,10-11,16-19H2,1-2H3,(H,31,34)(H,32,35)/t22-,23-,24-,25-/m0/s1
  • InChiKey: 
    NLJQXGSVYYFGHX-QORCZRPOSA-N

External links


25138065
CHEMBL487353
24703525

External search

Bibliography (1)

Publication Name
Sun H, Stuckey JA, Nikolovska-Coleska Z, Qin D, Meagher JL, Qiu S, Lu J, Yang CY, Saito NG, Wang S. . Structure-based design, synthesis, evaluation, and crystallographic studies of conformationally constrained Smac mimetics as inhibitors of the X-linked inhibitor of apoptosis protein (XIAP). Journal of medicinal chemistry. 21

Pharmacological data

Biochemical tests Cellular tests PK tests Cytotoxicity tests
1 1 0 0

Targets

PPI family Best activity Diseases MMoA
XIAP / Smac 7.17 cancer Inhibition
Physicochemical filters
Descriptor Lipinski's RO5 Veber Pfizer's 3/75
Compliance
MW 490.29 g/mol
HBA 7
HBD 3
HBA + HBD 10
AlogP 3.50
TPSA 90.54
RB 8
Radar chart
PCA : iPPI-DB chemical space
PCA : Correlation circle
Efficiencies: iPPI-DB biplot LE versus LLE
Summary
Bibliographic ressources Biochemical tests Cellular tests PK tests Cytotoxicity tests
1 1 1 0 0
Pharmacological data
Bibliography Name Target Competition Assay type Assay name Cell line Activity type Activity
18954041 21 XIAP
P98170
Biochemical assay Fluorescence Polarization pKi (inhibition constant, -log10) 7.17
18954041 21 XIAP
P98170
Cellular assay Proliferation assay MDA-MB-231 pIC50 (half maximal inhibitory concentration, -log10) 6.39
Ta Structure Name Drugbank ID
0.8022 3-cyclohexyl-D-alanyl-N-(3-chlorobenzyl)-L-prolinamide DB07190
0.7935 D-phenylalanyl-N-benzyl-L-prolinamide DB07143
0.7889 N-cyclooctylglycyl-N-(4-carbamimidoylbenzyl)-L-prolinamide DB06858
0.7802 N-cycloheptylglycyl-N-(4-carbamimidoylbenzyl)-L-prolinamide DB06853
0.7802 (S)-N-(4-carbamimidoylbenzyl)-1-(3-cyclopentylpropanoyl)pyrrolidine-2-carboxamide DB07095
0.7802 (S)-N-(4-carbamimidoylbenzyl)-1-(3-cyclohexylpropanoyl)pyrrolidine-2-carboxamide DB07131
0.7692 (S)-N-(4-carbamimidoylbenzyl)-1-(2-(cyclohexylamino)ethanoyl)pyrrolidine-2-carboxamide DB06850
0.7667 1-[(2R)-2-aminobutanoyl]-N-(3-chlorobenzyl)-L-prolinamide DB06878
0.7667 D-leucyl-N-(3-chlorobenzyl)-L-prolinamide DB06911
0.7667 1-[(2R)-2-aminobutanoyl]-N-(4-carbamimidoylbenzyl)-L-prolinamide DB06947
0.7667 D-leucyl-N-(4-carbamimidoylbenzyl)-L-prolinamide DB06996
0.7604 D-phenylalanyl-N-(3-methylbenzyl)-L-prolinamide DB07133
0.7475 1-[3,3-Dimethyl-2-(2-Methylamino-Propionylamino)-Butyryl]-Pyrrolidine-2-Carboxylic Acid(1,2,3,4-Tetrahydro-Naphthalen-1-Yl)-Amide DB02628
0.7472 (S)-N-(4-carbamimidoylbenzyl)-1-(2-(cyclopentylamino)ethanoyl)pyrrolidine-2-carboxamide DB06845
0.7444 N-(3-chlorobenzyl)-1-(4-methylpentanoyl)-L-prolinamide DB06868