iPPI-DB

Inhibitors of Protein-Protein Interaction Database

Compound 646

Identifiers

  • Canonical SMILES: 
    CC[C@H](N)C(=O)N[C@H]1CCCC[C@H]2CC[C@H](N2C1=O)C(=O)NC(c1ccccc1)c1ccccc1
  • IUPAC name: 
    (3S,6S,10aS)-6-[[(2S)-2-aminobutanoyl]amino]-N-benzhydryl-5-oxo-2,3,6,7,8,9,10,10a-octahydro-1H-pyrrolo[1,2-a]azocine-3-carboxamide
  • InChi: 
    InChI=1S/C28H36N4O3/c1-2-22(29)26(33)30-23-16-10-9-15-21-17-18-24(32(21)28(23)35)27(34)31-25(19-11-5-3-6-12-19)20-13-7-4-8-14-20/h3-8,11-14,21-25H,2,9-10,15-18,29H2,1H3,(H,30,33)(H,31,34)/t21-,22-,23-,24-/m0/s1
  • InChiKey: 
    SPMRYEMCEZYTQS-ZJZGAYNASA-N

External links


25138062
CHEMBL487149
24703443

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. 17

Pharmacological data

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

Targets

PPI family Best activity Diseases MMoA
XIAP / Smac 7.41 cancer Inhibition
Physicochemical filters
Descriptor Lipinski's RO5 Veber Pfizer's 3/75
Compliance
MW 476.28 g/mol
HBA 7
HBD 4
HBA + HBD 11
AlogP 3.07
TPSA 104.53
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 1 0 0
Pharmacological data
Bibliography Name Target Competition Assay type Assay name Cell line Activity type Activity
18954041 17 XIAP
P98170
Biochemical assay Fluorescence Polarization pKi (inhibition constant, -log10) 7.41
18954041 17 XIAP
P98170
Cellular assay Proliferation assay MDA-MB-231 pIC50 (half maximal inhibitory concentration, -log10) 5.10
Ta Structure Name Drugbank ID
0.8022 3-cyclohexyl-D-alanyl-N-(3-chlorobenzyl)-L-prolinamide DB07190
0.7935 D-phenylalanyl-N-benzyl-L-prolinamide DB07143
0.7889 N-cyclooctylglycyl-N-(4-carbamimidoylbenzyl)-L-prolinamide DB06858
0.7802 N-cycloheptylglycyl-N-(4-carbamimidoylbenzyl)-L-prolinamide DB06853
0.7802 (S)-N-(4-carbamimidoylbenzyl)-1-(3-cyclopentylpropanoyl)pyrrolidine-2-carboxamide DB07095
0.7802 (S)-N-(4-carbamimidoylbenzyl)-1-(3-cyclohexylpropanoyl)pyrrolidine-2-carboxamide DB07131
0.7692 (S)-N-(4-carbamimidoylbenzyl)-1-(2-(cyclohexylamino)ethanoyl)pyrrolidine-2-carboxamide DB06850
0.7667 1-[(2R)-2-aminobutanoyl]-N-(3-chlorobenzyl)-L-prolinamide DB06878
0.7667 D-leucyl-N-(3-chlorobenzyl)-L-prolinamide DB06911
0.7667 1-[(2R)-2-aminobutanoyl]-N-(4-carbamimidoylbenzyl)-L-prolinamide DB06947
0.7667 D-leucyl-N-(4-carbamimidoylbenzyl)-L-prolinamide DB06996
0.7604 D-phenylalanyl-N-(3-methylbenzyl)-L-prolinamide DB07133
0.7475 1-[3,3-Dimethyl-2-(2-Methylamino-Propionylamino)-Butyryl]-Pyrrolidine-2-Carboxylic Acid(1,2,3,4-Tetrahydro-Naphthalen-1-Yl)-Amide DB02628
0.7472 (S)-N-(4-carbamimidoylbenzyl)-1-(2-(cyclopentylamino)ethanoyl)pyrrolidine-2-carboxamide DB06845
0.7444 N-(3-chlorobenzyl)-1-(4-methylpentanoyl)-L-prolinamide DB06868