iPPI-DB

Inhibitors of Protein-Protein Interaction Database

Compound 713

Identifiers

  • Canonical SMILES: 
    CN[C@@H](C)C(=O)N[C@H]1CCCC[C@H]2CC[C@H](N2C1=O)C(=O)N[C@H]1CCCc2ccccc12
  • IUPAC name: 
    (3S,6S,10aS)-6-[[(2S)-2-(methylamino)propanoyl]amino]-5-oxo-N-[(1R)-1,2,3,4-tetrahydronaphthalen-1-yl]-2,3,6,7,8,9,10,10a-octahydro-1H-pyrrolo[1,2-a]azocine-3-carboxamide
  • InChi: 
    InChI=1S/C25H36N4O3/c1-16(26-2)23(30)28-21-12-6-4-10-18-14-15-22(29(18)25(21)32)24(31)27-20-13-7-9-17-8-3-5-11-19(17)20/h3,5,8,11,16,18,20-22,26H,4,6-7,9-10,12-15H2,1-2H3,(H,27,31)(H,28,30)/t16-,18-,20-,21-,22-/m0/s1
  • InChiKey: 
    IPIIAWQBJWTGKF-CPNAEOBWSA-N

External links


25138070
CHEMBL481421
24700385

External search

Bibliography (2)

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. 26
Sun W, Nikolovska-Coleska Z, Qin D, Sun H, Yang CY, Bai L, Qiu S, Wang Y, Ma D, Wang S. . Design, synthesis, and evaluation of potent, nonpeptidic mimetics of second mitochondria-derived activator of caspases. Journal of medicinal chemistry. 9

Pharmacological data

Biochemical tests Cellular tests PK tests Cytotoxicity tests
2 1 0 0

Targets

PPI family Best activity Diseases MMoA
XIAP / Smac 6.68 cancer Inhibition
Physicochemical filters
Descriptor Lipinski's RO5 Veber Pfizer's 3/75
Compliance
MW 440.28 g/mol
HBA 7
HBD 3
HBA + HBD 10
AlogP 2.18
TPSA 90.54
RB 5
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
2 2 1 0 0
Pharmacological data
Bibliography Name Target Competition Assay type Assay name Cell line Activity type Activity
18954041 26 XIAP
P98170
Biochemical assay Fluorescence Polarization pKi (inhibition constant, -log10) 6.56
19138149 9 XIAP
P98170
Biochemical assay Fluorescence Polarization pKi (inhibition constant, -log10) 6.68
19138149 9 XIAP
P98170
Cellular assay Proliferation assay MDA-MB-231 pIC50 (half maximal inhibitory concentration, -log10) 5.74
Ta Structure Name Drugbank ID
0.9684 1-[3,3-Dimethyl-2-(2-Methylamino-Propionylamino)-Butyryl]-Pyrrolidine-2-Carboxylic Acid(1,2,3,4-Tetrahydro-Naphthalen-1-Yl)-Amide DB02628
0.7736 (R)-Praziquantel DB11749
0.7736 Praziquantel DB01058
0.7379 D-phenylalanyl-N-benzyl-L-prolinamide DB07143
0.7103 D-phenylalanyl-N-(3-methylbenzyl)-L-prolinamide DB07133
0.7000 D-phenylalanyl-N-(3-fluorobenzyl)-L-prolinamide DB07027
0.6952 3-cyclohexyl-D-alanyl-N-(3-chlorobenzyl)-L-prolinamide DB07190
0.6827 N-cyclooctylglycyl-N-(4-carbamimidoylbenzyl)-L-prolinamide DB06858
0.6789 N-(4-carbamimidoylbenzyl)-1-(3-phenylpropanoyl)-L-prolinamide DB06942
0.6786 D-phenylalanyl-N-(3-chlorobenzyl)-L-prolinamide DB06919
0.6786 D-phenylalanyl-N-{4-[amino(iminio)methyl]benzyl}-L-prolinamide DB07005
0.6762 N-cycloheptylglycyl-N-(4-carbamimidoylbenzyl)-L-prolinamide DB06853
0.6762 (S)-N-(4-carbamimidoylbenzyl)-1-(3-cyclopentylpropanoyl)pyrrolidine-2-carboxamide DB07095
0.6762 (S)-N-(4-carbamimidoylbenzyl)-1-(3-cyclohexylpropanoyl)pyrrolidine-2-carboxamide DB07131
0.6667 N-METHYLALANYL-3-METHYLVALYL-4-PHENOXY-N-(1,2,3,4-TETRAHYDRONAPHTHALEN-1-YL)PROLINAMIDE DB04612