iPPI-DB

Inhibitors of Protein-Protein Interaction Database

Compound 633

Identifiers

  • Canonical SMILES: 
    CC[C@H](N(C)C)C(=O)N[C@H]1CCC[C@H]2CC[C@H](N2C1=O)C(=O)NC(c1ccccc1)c1ccccc1
  • IUPAC name: 
    (3S,6S,9aS)-N-benzhydryl-6-[[(2S)-2-(dimethylamino)butanoyl]amino]-5-oxo-1,2,3,6,7,8,9,9a-octahydropyrrolo[1,2-a]azepine-3-carboxamide
  • InChi: 
    InChI=1S/C29H38N4O3/c1-4-24(32(2)3)27(34)30-23-17-11-16-22-18-19-25(33(22)29(23)36)28(35)31-26(20-12-7-5-8-13-20)21-14-9-6-10-15-21/h5-10,12-15,22-26H,4,11,16-19H2,1-3H3,(H,30,34)(H,31,35)/t22-,23-,24-,25-/m0/s1
  • InChiKey: 
    CKOYRIROPKBZLR-QORCZRPOSA-N

External links


11562245
CHEMBL219139
9737019

External search

Bibliography (2)

Publication Name
Sun H, Nikolovska-Coleska Z, Lu J, Qiu S, Yang CY, Gao W, Meagher J, Stuckey J, Wang S. . Design, synthesis, and evaluation of a potent, cell-permeable, conformationally constrained second mitochondria derived activator of caspase (Smac) mimetic. Journal of medicinal chemistry. 3
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. 14

Pharmacological data

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

Targets

PPI family Best activity Diseases MMoA
XIAP / Smac 5.52 cancer Inhibition
Physicochemical filters
Descriptor Lipinski's RO5 Veber Pfizer's 3/75
Compliance
MW 490.29 g/mol
HBA 7
HBD 2
HBA + HBD 9
AlogP 3.44
TPSA 81.75
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
2 2 1 0 0
Pharmacological data
Bibliography Name Target Competition Assay type Assay name Cell line Activity type Activity
17181177 3 XIAP
P98170
Biochemical assay Fluorescence Polarization pKi (inhibition constant, -log10) 4.84
18954041 14 XIAP
P98170
Biochemical assay Fluorescence Polarization pKi (inhibition constant, -log10) 4.84
17181177 3 XIAP
P98170
Cellular assay Proliferation assay MDA-MB-231 pIC50 (half maximal inhibitory concentration, -log10) 5.52
Ta Structure Name Drugbank ID
0.7935 3-cyclohexyl-D-alanyl-N-(3-chlorobenzyl)-L-prolinamide DB07190
0.7850 D-phenylalanyl-N-benzyl-L-prolinamide DB07143
0.7802 N-cyclooctylglycyl-N-(4-carbamimidoylbenzyl)-L-prolinamide DB06858
0.7717 N-cycloheptylglycyl-N-(4-carbamimidoylbenzyl)-L-prolinamide DB06853
0.7717 (S)-N-(4-carbamimidoylbenzyl)-1-(3-cyclopentylpropanoyl)pyrrolidine-2-carboxamide DB07095
0.7717 (S)-N-(4-carbamimidoylbenzyl)-1-(3-cyclohexylpropanoyl)pyrrolidine-2-carboxamide DB07131
0.7609 (S)-N-(4-carbamimidoylbenzyl)-1-(2-(cyclohexylamino)ethanoyl)pyrrolidine-2-carboxamide DB06850
0.7582 1-[(2R)-2-aminobutanoyl]-N-(3-chlorobenzyl)-L-prolinamide DB06878
0.7582 D-leucyl-N-(3-chlorobenzyl)-L-prolinamide DB06911
0.7582 1-[(2R)-2-aminobutanoyl]-N-(4-carbamimidoylbenzyl)-L-prolinamide DB06947
0.7582 D-leucyl-N-(4-carbamimidoylbenzyl)-L-prolinamide DB06996
0.7526 D-phenylalanyl-N-(3-methylbenzyl)-L-prolinamide DB07133
0.7400 1-[3,3-Dimethyl-2-(2-Methylamino-Propionylamino)-Butyryl]-Pyrrolidine-2-Carboxylic Acid(1,2,3,4-Tetrahydro-Naphthalen-1-Yl)-Amide DB02628
0.7391 (S)-N-(4-carbamimidoylbenzyl)-1-(2-(cyclopentylamino)ethanoyl)pyrrolidine-2-carboxamide DB06845
0.7363 N-(3-chlorobenzyl)-1-(4-methylpentanoyl)-L-prolinamide DB06868