iPPI-DB

Inhibitors of Protein-Protein Interaction Database

Compound 827

Identifiers

  • Canonical SMILES: 
    CC[C@H](O)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-hydroxybutanoyl]amino]-5-oxo-1,2,3,6,7,8,9,9a-octahydropyrrolo[1,2-a]azepine-3-carboxamide
  • InChi: 
    InChI=1S/C27H33N3O4/c1-2-23(31)26(33)28-21-15-9-14-20-16-17-22(30(20)27(21)34)25(32)29-24(18-10-5-3-6-11-18)19-12-7-4-8-13-19/h3-8,10-13,20-24,31H,2,9,14-17H2,1H3,(H,28,33)(H,29,32)/t20-,21-,22-,23-/m0/s1
  • InChiKey: 
    HVADKVMBUUALGR-MLCQCVOFSA-N

External links


25138060
CHEMBL487383
24704292

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. 15

Pharmacological data

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

Targets

PPI family Best activity Diseases MMoA
XIAP / Smac 4.54 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 2.73
TPSA 98.74
RB 7
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 0 0 0
Pharmacological data
Bibliography Name Target Competition Assay type Assay name Cell line Activity type Activity
18954041 15 XIAP
P98170
Biochemical assay Fluorescence Polarization pKi (inhibition constant, -log10) 4.54
Ta Structure Name Drugbank ID
0.7222 Melagatran DB13616
0.7200 N-cyclooctylglycyl-N-(4-carbamimidoylbenzyl)-L-prolinamide DB06858
0.7157 3-cyclohexyl-D-alanyl-N-(3-chlorobenzyl)-L-prolinamide DB07190
0.7129 N-cycloheptylglycyl-N-(4-carbamimidoylbenzyl)-L-prolinamide DB06853
0.7129 (S)-N-(4-carbamimidoylbenzyl)-1-(3-cyclopentylpropanoyl)pyrrolidine-2-carboxamide DB07095
0.7129 (S)-N-(4-carbamimidoylbenzyl)-1-(3-cyclohexylpropanoyl)pyrrolidine-2-carboxamide DB07131
0.7087 D-phenylalanyl-N-benzyl-L-prolinamide DB07143
0.7030 (S)-N-(4-carbamimidoylbenzyl)-1-(2-(cyclohexylamino)ethanoyl)pyrrolidine-2-carboxamide DB06850
0.7000 1-[(2R)-2-aminobutanoyl]-N-(4-carbamimidoylbenzyl)-L-prolinamide DB06947
0.7000 D-leucyl-N-(4-carbamimidoylbenzyl)-L-prolinamide DB06996
0.6981 D-phenylalanyl-N-(3-methylbenzyl)-L-prolinamide DB07133
0.6832 (S)-N-(4-carbamimidoylbenzyl)-1-(2-(cyclopentylamino)ethanoyl)pyrrolidine-2-carboxamide DB06845
0.6832 1-[(2R)-2-aminobutanoyl]-N-(3-chlorobenzyl)-L-prolinamide DB06878
0.6832 D-leucyl-N-(3-chlorobenzyl)-L-prolinamide DB06911
0.6800 1-butanoyl-N-(4-carbamimidoylbenzyl)-L-prolinamide DB06929