iPPI-DB

Inhibitors of Protein-Protein Interaction Database

Compound 1255

Identifiers

  • Canonical SMILES: 
    CC[C@H](N)C(=O)N[C@H]1[C@@H](CNC(=S)NCc2ccccc2)CC[C@H]2CC[C@H](N2C1=O)C(=O)NC(c1ccccc1)c1ccccc1
  • IUPAC name: 
    (3S,6S,7R,9aS)-6-[[(2R)-2-aminobutanoyl]amino]-N-benzhydryl-7-[(benzylcarbamothioylamino)methyl]-5-oxo-1,2,3,6,7,8,9,9a-octahydropyrrolo[1,2-a]azepine-3-carboxamide
  • InChi: 
    InChI=1S/C36H44N6O3S/c1-2-29(37)33(43)41-32-27(23-39-36(46)38-22-24-12-6-3-7-13-24)18-19-28-20-21-30(42(28)35(32)45)34(44)40-31(25-14-8-4-9-15-25)26-16-10-5-11-17-26/h3-17,27-32H,2,18-23,37H2,1H3,(H,40,44)(H,41,43)(H2,38,39,46)/t27-,28+,29+,30+,32+/m1/s1
  • InChiKey: 
    BAMKYWPNUMTYIE-HVSNEVFASA-N

External links


44237062
CHEMBL582975
24642012

External search

Bibliography (2)

Publication Name
Seneci P, Bianchi A, Battaglia C, Belvisi L, Bolognesi M, Caprini A, Cossu F, Franco Ed, Matteo Md, Delia D, Drago C, Khaled A, Lecis D, Manzoni L, Marizzoni M, Mastrangelo E, Milani M, Motto I, Moroni E, Potenza D, Rizzo V, Servida F, Turlizzi E, Varrone M, Vasile F, Scolastico C. . Rational design, synthesis and characterization of potent, non-peptidic Smac mimics/XIAP inhibitors as proapoptotic agents for cancer therapy. Bioorganic & medicinal chemistry. 26d
Carlo Scolastico, Leonardo Pierpaolo Manzoni, Pierfausto Seneci, Laura Belvisi, Domenico Delia, Martino Bolognesi, Eloise Mastrangelo, Mario De Mayo De Mari Milani, Llaria Motto, Carmelo Drago, Universita'degli Studi Di Milano, Fondazione Irccs Istituto Nazionale Dei Tumori. . Smac mimetic compounds as apoptosis inducers None. 32d

Pharmacological data

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

Targets

PPI family Best activity Diseases MMoA
XIAP / Smac 6.48 cancer Inhibition
Physicochemical filters
Descriptor Lipinski's RO5 Veber Pfizer's 3/75
Compliance
MW 640.32 g/mol
HBA 9
HBD 6
HBA + HBD 15
AlogP 3.81
TPSA 128.59
RB 11
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
19620011 26d XIAP
P98170
Biochemical assay Fluorescence Polarization pIC50 (half maximal inhibitory concentration, -log10) 6.42
WO2009060292 32d XIAP
P98170
Biochemical assay Fluorescence Polarization pIC50 (half maximal inhibitory concentration, -log10) 6.48
Ta Structure Name Drugbank ID
0.6212 Neocitrullamon DB13396
0.6066 D-phenylalanyl-N-benzyl-L-prolinamide DB07143
0.5984 3-cyclohexyl-D-alanyl-N-(3-chlorobenzyl)-L-prolinamide DB07190
0.5873 D-phenylalanyl-N-(3-methylbenzyl)-L-prolinamide DB07133
0.5868 N-cyclooctylglycyl-N-(4-carbamimidoylbenzyl)-L-prolinamide DB06858
0.5828 Orvepitant DB12427
0.5820 N-cycloheptylglycyl-N-(4-carbamimidoylbenzyl)-L-prolinamide DB06853
0.5820 (S)-N-(4-carbamimidoylbenzyl)-1-(3-cyclopentylpropanoyl)pyrrolidine-2-carboxamide DB07095
0.5820 (S)-N-(4-carbamimidoylbenzyl)-1-(3-cyclohexylpropanoyl)pyrrolidine-2-carboxamide DB07131
0.5814 1-[3,3-Dimethyl-2-(2-Methylamino-Propionylamino)-Butyryl]-Pyrrolidine-2-Carboxylic Acid(1,2,3,4-Tetrahydro-Naphthalen-1-Yl)-Amide DB02628
0.5738 (S)-N-(4-carbamimidoylbenzyl)-1-(2-(cyclohexylamino)ethanoyl)pyrrolidine-2-carboxamide DB06850
0.5702 1-[(2R)-2-aminobutanoyl]-N-(3-chlorobenzyl)-L-prolinamide DB06878
0.5702 D-leucyl-N-(3-chlorobenzyl)-L-prolinamide DB06911
0.5702 1-[(2R)-2-aminobutanoyl]-N-(4-carbamimidoylbenzyl)-L-prolinamide DB06947
0.5702 D-leucyl-N-(4-carbamimidoylbenzyl)-L-prolinamide DB06996