iPPI-DB

Inhibitors of Protein-Protein Interaction Database

Compound 268

Identifiers

  • Canonical SMILES: 
    CN[C@@H](C)C(=O)N[C@H]1CCCC[C@H]2CC[C@H](N2C1=O)C(=O)NC(c1ccccc1)c1ccccc1
  • IUPAC name: 
    (3S,6S)-N-benzhydryl-6-[[(2S)-2-(methylamino)propanoyl]amino]-5-oxo-2,3,6,7,8,9,10,10a-octahydro-1H-pyrrolo[1,2-a]azocine-3-carboxamide
  • InChi: 
    InChI=1S/C28H36N4O3/c1-19(29-2)26(33)30-23-16-10-9-15-22-17-18-24(32(22)28(23)35)27(34)31-25(20-11-5-3-6-12-20)21-13-7-4-8-14-21/h3-8,11-14,19,22-25,29H,9-10,15-18H2,1-2H3,(H,30,33)(H,31,34)/t19-,22-,23-,24-/m0/s1
  • InChiKey: 
    XBTLZUHJBOBKRG-HCUBDLJJSA-N

External links


24754886
CHEMBL481422
24700386

External search

Bibliography (4)

Publication Name
Sun H, Nikolovska-Coleska Z, Lu J, Meagher JL, Yang CY, Qiu S, Tomita Y, Ueda Y, Jiang S, Krajewski K, Roller PP, Stuckey JA, Wang S. . Design, synthesis, and characterization of a potent, nonpeptide, cell-permeable, bivalent Smac mimetic that concurrently targets both the BIR2 and BIR3 domains in XIAP. Journal of the American Chemical Society. 1
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. 20
Sun W, Nikolovska-Coleska Z, Qin D, Sun H, Yang CY, Bai L, Qiu S, Wang Y, Ma D, Wang S. . Design, synthesis, and evaluation of potent, nonpeptidic mimetics of second mitochondria-derived activator of caspases. Journal of medicinal chemistry. 7
Sun H, Lu J, Liu L, Yi H, Qiu S, Yang CY, Deschamps JR, Wang S. . Nonpeptidic and potent small-molecule inhibitors of cIAP-1/2 and XIAP proteins. Journal of medicinal chemistry. 1

Pharmacological data

Biochemical tests Cellular tests PK tests Cytotoxicity tests
5 2 0 0

Targets

PPI family Best activity Diseases MMoA
XIAP / Smac 7.59 cancer Inhibition
Physicochemical filters
Descriptor Lipinski's RO5 Veber Pfizer's 3/75
Compliance
MW 476.28 g/mol
HBA 7
HBD 3
HBA + HBD 10
AlogP 2.98
TPSA 90.54
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
4 5 2 0 0
Pharmacological data
Bibliography Name Target Competition Assay type Assay name Cell line Activity type Activity
17999504 1 XIAP
P98170
Biochemical assay Fluorescence Polarization pKi (inhibition constant, -log10) 7.04
18954041 20 XIAP
P98170
Biochemical assay Fluorescence Polarization pKi (inhibition constant, -log10) 7.59
19138149 7 XIAP
P98170
Biochemical assay Fluorescence Polarization pKi (inhibition constant, -log10) 7.59
20684551 1 XIAP
P98170
Biochemical assay Fluorescence Polarization pIC50 (half maximal inhibitory concentration, -log10) 6.20
20684551 1 XIAP
P98170
Biochemical assay Fluorescence Polarization pKi (inhibition constant, -log10) 6.72
19138149 7 XIAP
P98170
Cellular assay Proliferation assay MDA-MB-231 pIC50 (half maximal inhibitory concentration, -log10) 6.59
18954041 20 XIAP
P98170
Cellular assay Proliferation assay MDA-MB-231 pIC50 (half maximal inhibitory concentration, -log10) 6.39
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