iPPI-DB

Inhibitors of Protein-Protein Interaction Database

Compound 605

Identifiers

  • Canonical SMILES: 
    C[C@H](N)C(=O)N[C@H]1CC[C@H]2CC[C@H](N2C1=O)C(=O)NCc1ccccc1
  • IUPAC name: 
    (3S,6S,8aR)-6-[[(2S)-2-aminopropanoyl]amino]-N-benzyl-5-oxo-2,3,6,7,8,8a-hexahydro-1H-indolizine-3-carboxamide
  • InChi: 
    InChI=1S/C19H26N4O3/c1-12(20)17(24)22-15-9-7-14-8-10-16(23(14)19(15)26)18(25)21-11-13-5-3-2-4-6-13/h2-6,12,14-16H,7-11,20H2,1H3,(H,21,25)(H,22,24)/t12-,14-,15-,16-/m0/s1
  • InChiKey: 
    HRYYDNAJRUXAJE-TUUVXOQKSA-N

External links


11326885
9501837

External search

Bibliography (3)

Publication Name
Sun H, Nikolovska-Coleska Z, Yang CY, Xu L, Tomita Y, Krajewski K, Roller PP, Wang S. . Structure-based design, synthesis, and evaluation of conformationally constrained mimetics of the second mitochondria-derived activator of caspase that target the X-linked inhibitor of apoptosis protein/caspase-9 interaction site. Journal of medicinal chemistry. 2
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. 3
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. 2

Pharmacological data

Biochemical tests Cellular tests PK tests Cytotoxicity tests
3 0 0 0

Targets

PPI family Best activity Diseases MMoA
XIAP / Smac 5.35 cancer Inhibition
Physicochemical filters
Descriptor Lipinski's RO5 Veber Pfizer's 3/75
Compliance
MW 358.20 g/mol
HBA 7
HBD 4
HBA + HBD 11
AlogP -0.13
TPSA 104.53
RB 5
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
3 3 0 0 0
Pharmacological data
Bibliography Name Target Competition Assay type Assay name Cell line Activity type Activity
15612682 3 XIAP
P98170
Biochemical assay Fluorescence Polarization pKi (inhibition constant, -log10) 5.35
15293984 2 XIAP
P98170
Biochemical assay Fluorescence Polarization pKi (inhibition constant, -log10) 5.35
18954041 2 XIAP
P98170
Biochemical assay Fluorescence Polarization pKi (inhibition constant, -log10) 5.35
Ta Structure Name Drugbank ID
0.8488 3-cyclohexyl-D-alanyl-N-(3-chlorobenzyl)-L-prolinamide DB07190
0.8353 N-cyclooctylglycyl-N-(4-carbamimidoylbenzyl)-L-prolinamide DB06858
0.8256 N-cycloheptylglycyl-N-(4-carbamimidoylbenzyl)-L-prolinamide DB06853
0.8256 (S)-N-(4-carbamimidoylbenzyl)-1-(3-cyclopentylpropanoyl)pyrrolidine-2-carboxamide DB07095
0.8256 (S)-N-(4-carbamimidoylbenzyl)-1-(3-cyclohexylpropanoyl)pyrrolidine-2-carboxamide DB07131
0.8140 (S)-N-(4-carbamimidoylbenzyl)-1-(2-(cyclohexylamino)ethanoyl)pyrrolidine-2-carboxamide DB06850
0.8118 1-[(2R)-2-aminobutanoyl]-N-(3-chlorobenzyl)-L-prolinamide DB06878
0.8118 D-leucyl-N-(3-chlorobenzyl)-L-prolinamide DB06911
0.8118 1-[(2R)-2-aminobutanoyl]-N-(4-carbamimidoylbenzyl)-L-prolinamide DB06947
0.8118 D-leucyl-N-(4-carbamimidoylbenzyl)-L-prolinamide DB06996
0.7907 (S)-N-(4-carbamimidoylbenzyl)-1-(2-(cyclopentylamino)ethanoyl)pyrrolidine-2-carboxamide DB06845
0.7882 N-(3-chlorobenzyl)-1-(4-methylpentanoyl)-L-prolinamide DB06868
0.7882 1-butanoyl-N-(4-carbamimidoylbenzyl)-L-prolinamide DB06929
0.7882 N-(4-carbamimidoylbenzyl)-1-(4-methylpentanoyl)-L-prolinamide DB06936
0.7582 D-phenylalanyl-N-benzyl-L-prolinamide DB07143