Compound 2080

Identifiers

Canonical SMILES:

CNC(C)C(=O)NC(C1CCCCC1)C(=O)N1C[C@H]2CCCN2CC1C(=O)NC1CCOc2ccccc12

IUPAC name:

(8aR)-2-{2-cyclohexyl-2-[2-(methylamino)propanamido]acetyl}-N-(3,4-dihydro-2H-1-benzopyran-4-yl)-octahydropyrrolo[1,2-a]pyrazine-3-carboxamide

InChi:

InChI=1S/C29H43N5O4/c1-19(30-2)27(35)32-26(20-9-4-3-5-10-20)29(37)34-17-21-11-8-15-33(21)18-24(34)28(36)31-23-14-16-38-25-13-7-6-12-22(23)25/h6-7,12-13,19-21,23-24,26,30H,3-5,8-11,14-18H2,1-2H3,(H,31,36)(H,32,35)/t19?,21-,23?,24?,26?/m1/s1

InChiKey:
```
GIAUJOMDUOPYLU-SAVXELPKSA-N
```

External links

168317786

1YH

External search

Bibliography (1)

Publication	Name
Asano Moriteru, Hashimoto Kentaro, Saito Bunnai, Shiokawa Zenyu, Sumi Hiroyuki, Yabuki Masato, Yoshimatsu Mie, Aoyama Kazunobu, Hamada Teruki, Morishita Nao, Dougan Douglas R., Mol Clifford D., Yoshida Sei, Ishikawa Tomoyasu. . Design, stereoselective synthesis, and biological evaluation of novel tri-cyclic compounds as inhibitor of apoptosis proteins (IAP) antagonists Bioorganic & Medicinal Chemistry.	a

Publication

Name

Asano Moriteru, Hashimoto Kentaro, Saito Bunnai, Shiokawa Zenyu, Sumi Hiroyuki, Yabuki Masato, Yoshimatsu Mie, Aoyama Kazunobu, Hamada Teruki, Morishita Nao, Dougan Douglas R., Mol Clifford D., Yoshida Sei, Ishikawa Tomoyasu. . Design, stereoselective synthesis, and biological evaluation of novel tri-cyclic compounds as inhibitor of apoptosis proteins (IAP) antagonists Bioorganic & Medicinal Chemistry.

Pharmacological data

Biochemical tests	Cellular tests	PK tests	Cytotoxicity tests
2	1	0	0

Targets

PPI family	Best activity	Diseases	MMoA
XIAP / Smac	8.68	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	525.33 g/mol
HBA	9
HBD	3
HBA + HBD	12
AlogP	1.65
TPSA	108.79
RB	7

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	2	1	0	0

Pharmacological data

Bibliography	Name	Target	Competition	Assay type	Assay name	Cell line	Activity type	Activity
10.1016/j.bmc.2013.07.020	a	XIAP P98170	DBLOH Q9NR28	Biochemical assay	HTRF-XIAP		pIC50 (half maximal inhibitory concentration, -log10)	6.62
10.1016/j.bmc.2013.07.020	a	XIAP P98170	DBLOH Q9NR28	Cellular assay	cell	MDA-MB-231 breast	pIC50 (half maximal inhibitory concentration, -log10)	8.24
10.1016/j.bmc.2013.07.020	a	XIAP P98170	DBLOH Q9NR28	Biochemical assay	HTRF-cIAP1		pIC50 (half maximal inhibitory concentration, -log10)	8.68

Ta	Name	Drugbank ID
0.6392	N-METHYLALANYL-3-METHYLVALYL-4-PHENOXY-N-(1,2,3,4-TETRAHYDRONAPHTHALEN-1-YL)PROLINAMIDE	DB04612
0.6333	1-[2-AMINO-2-CYCLOHEXYL-ACETYL]-PYRROLIDINE-3-CARBOXYLIC ACID 5-CHLORO-2-(2-ETHYLCARBAMOYL-ETHOXY)-BENZYLAMIDE	DB06869
0.5930	Aminocandin	DB05128
0.5742	Aplaviroc	DB06497
0.5667	Tavilermide	DB12441
0.5639	D-phenylalanyl-N-benzyl-L-prolinamide	DB07143
0.5588	D-phenylalanyl-N-(3-methylbenzyl)-L-prolinamide	DB07133
0.5454	Arylomycin A2	DB01934
0.5448	3-cyclohexyl-D-alanyl-N-(3-chlorobenzyl)-L-prolinamide	DB07190
0.5429	1-[3,3-Dimethyl-2-(2-Methylamino-Propionylamino)-Butyryl]-Pyrrolidine-2-Carboxylic Acid(1,2,3,4-Tetrahydro-Naphthalen-1-Yl)-Amide	DB02628
0.5414	(S)-N-(4-carbamimidoylbenzyl)-1-(3-cyclohexylpropanoyl)pyrrolidine-2-carboxamide	DB07131
0.5411	(9S,12S)-9-(1-methylethyl)-7,10-dioxo-2-oxa-8,11-diazabicyclo[12.2.2]octadeca-1(16),14,17-triene-12-carboxylic acid	DB07679
0.5390	D-phenylalanyl-N-{4-[amino(iminio)methyl]benzyl}-L-prolinamide	DB07005
0.5379	Flecainide	DB01195
0.5362	N-(4-carbamimidoylbenzyl)-1-(3-phenylpropanoyl)-L-prolinamide	DB06942