iPPI-DB

Inhibitors of Protein-Protein Interaction Database

Compound 1082

Identifiers

  • Canonical SMILES: 
    C[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-aminopropanoyl]amino]-N-benzhydryl-5-oxo-1,2,3,6,7,8,9,9a-octahydropyrrolo[1,2-a]azepine-3-carboxamide
  • InChi: 
    InChI=1S/C26H32N4O3/c1-17(27)24(31)28-21-14-8-13-20-15-16-22(30(20)26(21)33)25(32)29-23(18-9-4-2-5-10-18)19-11-6-3-7-12-19/h2-7,9-12,17,20-23H,8,13-16,27H2,1H3,(H,28,31)(H,29,32)/t17-,20-,21-,22-/m0/s1
  • InChiKey: 
    JHJTWSSGXYISJM-MQGJPIDWSA-N

External links


11190107
CHEMBL486772
9365189
SMK

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. 6
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. 11

Pharmacological data

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

Targets

PPI family Best activity Diseases MMoA
XIAP / Smac 7.22 cancer Inhibition
Physicochemical filters
Descriptor Lipinski's RO5 Veber Pfizer's 3/75
Compliance
MW 448.25 g/mol
HBA 7
HBD 4
HBA + HBD 11
AlogP 2.10
TPSA 104.53
RB 6
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 6 XIAP
P98170
Biochemical assay Fluorescence Polarization pKi (inhibition constant, -log10) 7.22
18954041 11 XIAP
P98170
Biochemical assay Fluorescence Polarization pKi (inhibition constant, -log10) 7.22
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