iPPI-DB

Inhibitors of Protein-Protein Interaction Database

Compound 587

Identifiers

  • Canonical SMILES: 
    CC[C@H](N)C(=O)N[C@H]1CCC[C@H]2CC[C@H](N2C1=O)C(=O)NC(c1ccccc1)c1ccccc1
  • IUPAC name: 
    (3S,6S,9aS)-6-[[(2S)-2-aminobutanoyl]amino]-N-benzhydryl-5-oxo-1,2,3,6,7,8,9,9a-octahydropyrrolo[1,2-a]azepine-3-carboxamide
  • InChi: 
    InChI=1S/C27H34N4O3/c1-2-21(28)25(32)29-22-15-9-14-20-16-17-23(31(20)27(22)34)26(33)30-24(18-10-5-3-6-11-18)19-12-7-4-8-13-19/h3-8,10-13,20-24H,2,9,14-17,28H2,1H3,(H,29,32)(H,30,33)/t20-,21-,22-,23-/m0/s1
  • InChiKey: 
    XWYMWLGPGRAJLM-MLCQCVOFSA-N

External links


11225031
CHEMBL375349
9400084
SMK

External search

Bibliography (4)

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. 7
Sun H, Nikolovska-Coleska Z, Lu J, Qiu S, Yang CY, Gao W, Meagher J, Stuckey J, Wang S. . Design, synthesis, and evaluation of a potent, cell-permeable, conformationally constrained second mitochondria derived activator of caspase (Smac) mimetic. Journal of medicinal chemistry. 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. 12
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. 1a

Pharmacological data

Biochemical tests Cellular tests PK tests Cytotoxicity tests
4 0 0 0

Targets

PPI family Best activity Diseases MMoA
XIAP / Smac 7.60 cancer Inhibition
Physicochemical filters
Descriptor Lipinski's RO5 Veber Pfizer's 3/75
Compliance
MW 462.26 g/mol
HBA 7
HBD 4
HBA + HBD 11
AlogP 2.62
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
4 4 0 0 0
Pharmacological data
Bibliography Name Target Competition Assay type Assay name Cell line Activity type Activity
19620011 1a XIAP
P98170
Biochemical assay Fluorescence Polarization pIC50 (half maximal inhibitory concentration, -log10) 6.34
15612682 7 XIAP
P98170
Biochemical assay Fluorescence Polarization pKi (inhibition constant, -log10) 7.60
17181177 1 XIAP
P98170
Biochemical assay Fluorescence Polarization pKi (inhibition constant, -log10) 7.60
18954041 12 XIAP
P98170
Biochemical assay Fluorescence Polarization pKi (inhibition constant, -log10) 7.60
Ta Structure Name Drugbank ID
0.7935 3-cyclohexyl-D-alanyl-N-(3-chlorobenzyl)-L-prolinamide DB07190
0.7850 D-phenylalanyl-N-benzyl-L-prolinamide DB07143
0.7802 N-cyclooctylglycyl-N-(4-carbamimidoylbenzyl)-L-prolinamide DB06858
0.7717 N-cycloheptylglycyl-N-(4-carbamimidoylbenzyl)-L-prolinamide DB06853
0.7717 (S)-N-(4-carbamimidoylbenzyl)-1-(3-cyclopentylpropanoyl)pyrrolidine-2-carboxamide DB07095
0.7717 (S)-N-(4-carbamimidoylbenzyl)-1-(3-cyclohexylpropanoyl)pyrrolidine-2-carboxamide DB07131
0.7609 (S)-N-(4-carbamimidoylbenzyl)-1-(2-(cyclohexylamino)ethanoyl)pyrrolidine-2-carboxamide DB06850
0.7582 1-[(2R)-2-aminobutanoyl]-N-(3-chlorobenzyl)-L-prolinamide DB06878
0.7582 D-leucyl-N-(3-chlorobenzyl)-L-prolinamide DB06911
0.7582 1-[(2R)-2-aminobutanoyl]-N-(4-carbamimidoylbenzyl)-L-prolinamide DB06947
0.7582 D-leucyl-N-(4-carbamimidoylbenzyl)-L-prolinamide DB06996
0.7526 D-phenylalanyl-N-(3-methylbenzyl)-L-prolinamide DB07133
0.7400 1-[3,3-Dimethyl-2-(2-Methylamino-Propionylamino)-Butyryl]-Pyrrolidine-2-Carboxylic Acid(1,2,3,4-Tetrahydro-Naphthalen-1-Yl)-Amide DB02628
0.7391 (S)-N-(4-carbamimidoylbenzyl)-1-(2-(cyclopentylamino)ethanoyl)pyrrolidine-2-carboxamide DB06845
0.7363 N-(3-chlorobenzyl)-1-(4-methylpentanoyl)-L-prolinamide DB06868