iPPI-DB

Inhibitors of Protein-Protein Interaction Database

Compound 941

Identifiers

  • Canonical SMILES: 
    C[C@H](N)C(=O)N[C@H]1CCC[C@H]2CC[C@H](N2C1=O)C(=O)NCc1ccccc1
  • IUPAC name: 
    (3S,6S,9aS)-6-[[(2S)-2-aminopropanoyl]amino]-N-benzyl-5-oxo-1,2,3,6,7,8,9,9a-octahydropyrrolo[1,2-a]azepine-3-carboxamide
  • InChi: 
    InChI=1S/C20H28N4O3/c1-13(21)18(25)23-16-9-5-8-15-10-11-17(24(15)20(16)27)19(26)22-12-14-6-3-2-4-7-14/h2-4,6-7,13,15-17H,5,8-12,21H2,1H3,(H,22,26)(H,23,25)/t13-,15-,16-,17-/m0/s1
  • InChiKey: 
    FHZYBAJOAPZBPA-HJWJTTGWSA-N

External links


11417422
CHEMBL510669
9592309

External search

Bibliography (2)

Publication Name
Sun H, Nikolovska-Coleska Z, Yang CY, Xu L, Liu M, Tomita Y, Pan H, Yoshioka Y, Krajewski K, Roller PP, Wang S. . Structure-based design of potent, conformationally constrained Smac mimetics. Journal of the American Chemical Society. 5
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. 4

Pharmacological data

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

Targets

PPI family Best activity Diseases MMoA
XIAP / Smac 6.82 cancer Inhibition
Physicochemical filters
Descriptor Lipinski's RO5 Veber Pfizer's 3/75
Compliance
MW 372.22 g/mol
HBA 7
HBD 4
HBA + HBD 11
AlogP 0.32
TPSA 104.53
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 0 0 0
Pharmacological data
Bibliography Name Target Competition Assay type Assay name Cell line Activity type Activity
15612682 5 XIAP
P98170
Biochemical assay Fluorescence Polarization pKi (inhibition constant, -log10) 6.82
18954041 4 XIAP
P98170
Biochemical assay Fluorescence Polarization pKi (inhibition constant, -log10) 6.82
Ta Structure Name Drugbank ID
0.8690 3-cyclohexyl-D-alanyl-N-(3-chlorobenzyl)-L-prolinamide DB07190
0.8554 N-cyclooctylglycyl-N-(4-carbamimidoylbenzyl)-L-prolinamide DB06858
0.8452 N-cycloheptylglycyl-N-(4-carbamimidoylbenzyl)-L-prolinamide DB06853
0.8452 (S)-N-(4-carbamimidoylbenzyl)-1-(3-cyclopentylpropanoyl)pyrrolidine-2-carboxamide DB07095
0.8452 (S)-N-(4-carbamimidoylbenzyl)-1-(3-cyclohexylpropanoyl)pyrrolidine-2-carboxamide DB07131
0.8333 (S)-N-(4-carbamimidoylbenzyl)-1-(2-(cyclohexylamino)ethanoyl)pyrrolidine-2-carboxamide DB06850
0.8313 1-[(2R)-2-aminobutanoyl]-N-(3-chlorobenzyl)-L-prolinamide DB06878
0.8313 D-leucyl-N-(3-chlorobenzyl)-L-prolinamide DB06911
0.8313 1-[(2R)-2-aminobutanoyl]-N-(4-carbamimidoylbenzyl)-L-prolinamide DB06947
0.8313 D-leucyl-N-(4-carbamimidoylbenzyl)-L-prolinamide DB06996
0.8095 (S)-N-(4-carbamimidoylbenzyl)-1-(2-(cyclopentylamino)ethanoyl)pyrrolidine-2-carboxamide DB06845
0.8072 N-(3-chlorobenzyl)-1-(4-methylpentanoyl)-L-prolinamide DB06868
0.8072 1-butanoyl-N-(4-carbamimidoylbenzyl)-L-prolinamide DB06929
0.8072 N-(4-carbamimidoylbenzyl)-1-(4-methylpentanoyl)-L-prolinamide DB06936
0.7753 D-phenylalanyl-N-benzyl-L-prolinamide DB07143