iPPI-DB

Inhibitors of Protein-Protein Interaction Database

Compound 495

Identifiers

  • Canonical SMILES: 
    C[C@H](O)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-hydroxypropanoyl]amino]-5-oxo-2,3,6,7,8,9,10,10a-octahydro-1H-pyrrolo[1,2-a]azocine-3-carboxamide
  • InChi: 
    InChI=1S/C27H33N3O4/c1-18(31)25(32)28-22-15-9-8-14-21-16-17-23(30(21)27(22)34)26(33)29-24(19-10-4-2-5-11-19)20-12-6-3-7-13-20/h2-7,10-13,18,21-24,31H,8-9,14-17H2,1H3,(H,28,32)(H,29,33)/t18-,21-,22-,23-/m0/s1
  • InChiKey: 
    MEIDRYNCEXLIEO-QGQQZZQASA-N

External links


25138068
CHEMBL486330
24703250

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. 24

Pharmacological data

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

Targets

PPI family Best activity Diseases MMoA
XIAP / Smac 5.15 cancer Inhibition
Physicochemical filters
Descriptor Lipinski's RO5 Veber Pfizer's 3/75
Compliance
MW 463.25 g/mol
HBA 7
HBD 3
HBA + HBD 10
AlogP 2.65
TPSA 98.74
RB 6
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 24 XIAP
P98170
Biochemical assay Fluorescence Polarization pKi (inhibition constant, -log10) 4.89
18954041 24 XIAP
P98170
Cellular assay Proliferation assay MDA-MB-231 pIC50 (half maximal inhibitory concentration, -log10) 5.15
Ta Structure Name Drugbank ID
0.7358 Melagatran DB13616
0.7347 N-cyclooctylglycyl-N-(4-carbamimidoylbenzyl)-L-prolinamide DB06858
0.7300 3-cyclohexyl-D-alanyl-N-(3-chlorobenzyl)-L-prolinamide DB07190
0.7273 N-cycloheptylglycyl-N-(4-carbamimidoylbenzyl)-L-prolinamide DB06853
0.7273 (S)-N-(4-carbamimidoylbenzyl)-1-(3-cyclopentylpropanoyl)pyrrolidine-2-carboxamide DB07095
0.7273 (S)-N-(4-carbamimidoylbenzyl)-1-(3-cyclohexylpropanoyl)pyrrolidine-2-carboxamide DB07131
0.7228 D-phenylalanyl-N-benzyl-L-prolinamide DB07143
0.7172 (S)-N-(4-carbamimidoylbenzyl)-1-(2-(cyclohexylamino)ethanoyl)pyrrolidine-2-carboxamide DB06850
0.7143 1-[(2R)-2-aminobutanoyl]-N-(4-carbamimidoylbenzyl)-L-prolinamide DB06947
0.7143 D-leucyl-N-(4-carbamimidoylbenzyl)-L-prolinamide DB06996
0.7115 D-phenylalanyl-N-(3-methylbenzyl)-L-prolinamide DB07133
0.6970 (S)-N-(4-carbamimidoylbenzyl)-1-(2-(cyclopentylamino)ethanoyl)pyrrolidine-2-carboxamide DB06845
0.6970 1-[(2R)-2-aminobutanoyl]-N-(3-chlorobenzyl)-L-prolinamide DB06878
0.6970 D-leucyl-N-(3-chlorobenzyl)-L-prolinamide DB06911
0.6939 1-butanoyl-N-(4-carbamimidoylbenzyl)-L-prolinamide DB06929