Compound 540

Identifiers

Canonical SMILES:

CC[C@H](N)C(=O)N[C@H]1[C@@H](Cn2cc(nn2)[C@H](O)CC)CC[C@H]2CC[C@H](N2C1=O)C(=O)NC(c1ccccc1)c1ccccc1

IUPAC name:

(3S,6S,7R,9aS)-6-[[(2S)-2-aminobutanoyl]amino]-N-benzhydryl-7-[[4-[(1R)-1-hydroxypropyl]triazol-1-yl]methyl]-5-oxo-1,2,3,6,7,8,9,9a-octahydropyrrolo[1,2-a]azepine-3-carboxamide

InChi:

InChI=1S/C33H43N7O4/c1-3-25(34)31(42)36-30-23(19-39-20-26(37-38-39)28(41)4-2)15-16-24-17-18-27(40(24)33(30)44)32(43)35-29(21-11-7-5-8-12-21)22-13-9-6-10-14-22/h5-14,20,23-25,27-30,41H,3-4,15-19,34H2,1-2H3,(H,35,43)(H,36,42)/t23-,24+,25+,27+,28-,30+/m1/s1

InChiKey:
```
BKDHFGCNNIXCGS-KCVLSDOGSA-N
```

External links

44237047

CHEMBL575151

24635872

External search

Bibliography (1)

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.	14a

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.

14a

Pharmacological data

Biochemical tests	Cellular tests	PK tests	Cytotoxicity tests
1	0	0	0

Targets

PPI family	Best activity	Diseases	MMoA
XIAP / Smac	6.43	cancer	Inhibition

Physicochemical filters

Descriptor	Lipinski's RO5	Veber	Pfizer's 3/75
MW	≤ 500 g/mol	-	-
AlogP	≤ 5	-	≤ 3
HBA	≤ 10	-	-
HBD	≤ 5	-	-
(HBA + HBD)	-	≤ 12	-
TPSA	-	≤ 140 Å²	≥ 75 Å²
RB	-	≤ 10	-

	Descriptor	Lipinski's RO5	Veber	Pfizer's 3/75
Compliance
MW	601.34 g/mol
HBA	11
HBD	5
HBA + HBD	16
AlogP	2.54
TPSA	155.47
RB	11

Radar chart

Short name	Threshold
MW	≤ 500 g/mol
AlogP	≤ 5
HBD	≤ 5
HBA	≤ 10
TPSA	≤ 140 Å²
RB	≤ 10
ArRing	≤ 4
Fsp3	≥ 0.4
R/S	≥ 1

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
1	1	0	0	0

Pharmacological data

Bibliography	Name	Target	Competition	Assay type	Assay name	Cell line	Activity type	Activity
19620011	14a	XIAP P98170		Biochemical assay	Fluorescence Polarization		pIC50 (half maximal inhibitory concentration, -log10)	6.43

Ta	Name	Drugbank ID
0.5053	IMG-7289	DB15126
0.5052	N-[(1S)-1-{1-[(1R,3E)-1-ACETYLPENT-3-EN-1-YL]-1H-1,2,3-TRIAZOL-4-YL}-1,2-DIMETHYLPROPYL]BENZAMIDE	DB07878
0.4946	MMI-175	DB02378
0.4908	Danegaptide	DB11821
0.4835	Maraviroc	DB04835
0.4780	3-cyclohexyl-D-alanyl-N-(3-chlorobenzyl)-L-prolinamide	DB07190
0.4684	N-cyclooctylglycyl-N-(4-carbamimidoylbenzyl)-L-prolinamide	DB06858
0.4671	D-phenylalanyl-N-(3-chlorobenzyl)-L-prolinamide	DB06919
0.4671	D-phenylalanyl-N-{4-[amino(iminio)methyl]benzyl}-L-prolinamide	DB07005
0.4660	Aminocandin	DB05128
0.4658	D-phenylalanyl-N-benzyl-L-prolinamide	DB07143
0.4654	N-cycloheptylglycyl-N-(4-carbamimidoylbenzyl)-L-prolinamide	DB06853
0.4654	(S)-N-(4-carbamimidoylbenzyl)-1-(3-cyclopentylpropanoyl)pyrrolidine-2-carboxamide	DB07095
0.4654	(S)-N-(4-carbamimidoylbenzyl)-1-(3-cyclohexylpropanoyl)pyrrolidine-2-carboxamide	DB07131
0.4649	RU82197	DB03268