Compound 517

Identifiers

Canonical SMILES:

CN1C(=O)N(C(=O)[C@]11CN(C[C@H]1c1ccc(cc1)C#N)c1nc2ccc(cc2o1)C(O)=O)c1cc(Cl)cc(Cl)c1

IUPAC name:

2-[(5S,9R)-9-(4-cyanophenyl)-3-(3,5-dichlorophenyl)-1-methyl-2,4-dioxo-1,3,7-triazaspiro[4.4]nonan-7-yl]-1,3-benzoxazole-6-carboxylic acid

InChi:

InChI=1S/C28H19Cl2N5O5/c1-33-27(39)35(20-10-18(29)9-19(30)11-20)25(38)28(33)14-34(13-21(28)16-4-2-15(12-31)3-5-16)26-32-22-7-6-17(24(36)37)8-23(22)40-26/h2-11,21H,13-14H2,1H3,(H,36,37)/t21-,28+/m0/s1

InChiKey:
```
YJPXVQLGBKABGV-RBTNQOKQSA-N
```

External links

46221190

CHEMBL1095148

24669735

External search

Bibliography (1)

Publication	Name
Watterson SH, Xiao Z, Dodd DS, Tortolani DR, Vaccaro W, Potin D, Launay M, Stetsko DK, Skala S, Davis PM, Lee D, Yang X, McIntyre KW, Balimane P, Patel K, Yang Z, Marathe P, Kadiyala P, Tebben AJ, Sheriff S, Chang CY, Ziemba T, Zhang H, Chen BC, DelMonte AJ, Aranibar N, McKinnon M, Barrish JC, Suchard SJ, Murali Dhar TG. . Small molecule antagonist of leukocyte function associated antigen-1 (LFA-1): structure-activity relationships leading to the identification of 6-((5S,9R)-9-(4-cyanophenyl)-3-(3,5-dichlorophenyl)-1-methyl-2,4-dioxo-1,3,7-triazaspiro[4.4]nonan-7-yl)nicotinic acid (BMS-688521). Journal of medicinal chemistry.	2s

Publication

Name

Watterson SH, Xiao Z, Dodd DS, Tortolani DR, Vaccaro W, Potin D, Launay M, Stetsko DK, Skala S, Davis PM, Lee D, Yang X, McIntyre KW, Balimane P, Patel K, Yang Z, Marathe P, Kadiyala P, Tebben AJ, Sheriff S, Chang CY, Ziemba T, Zhang H, Chen BC, DelMonte AJ, Aranibar N, McKinnon M, Barrish JC, Suchard SJ, Murali Dhar TG. . Small molecule antagonist of leukocyte function associated antigen-1 (LFA-1): structure-activity relationships leading to the identification of 6-((5S,9R)-9-(4-cyanophenyl)-3-(3,5-dichlorophenyl)-1-methyl-2,4-dioxo-1,3,7-triazaspiro[4.4]nonan-7-yl)nicotinic acid (BMS-688521). Journal of medicinal chemistry.

Pharmacological data

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

Targets

PPI family	Best activity	Diseases	MMoA
LFA / ICAM	8.22	immune system disease	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	575.08 g/mol
HBA	10
HBD	1
HBA + HBD	11
AlogP	5.11
TPSA	130.98
RB	4

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
20405922	2s	ITAL P20701		Biochemical assay	ELISA		pIC50 (half maximal inhibitory concentration, -log10)	8.22

Ta	Name	Drugbank ID
0.5110	Suvorexant	DB09034
0.4925	Degarelix	DB06699
0.4819	N~2~-1,3-BENZOXAZOL-2-YL-3-CYCLOHEXYL-N-{2-[(4-METHOXYPHENYL)AMINO]ETHYL}-L-ALANINAMIDE	DB07839
0.4306	Alatrofloxacin	DB09335
0.4291	BMS-564929	DB07286
0.4262	Ubrogepant	DB15328
0.4203	SAR-405838	DB12541
0.4191	ALK-4290	DB15269
0.4189	Ivosidenib	DB14568
0.4151	Telinavir	DB12178
0.4149	Olcegepant	DB04869
0.4120	Bremelanotide	DB11653
0.4099	SJ-733	DB12659
0.4086	Cp403700, (S)-1-{2-[(5-Chloro-1h-Indole-2-Carbonyl)-Amino]-3-Phenyl-Propionyl}-Azetidine-3-Carboxylate	DB03744
0.4083	MK-3207	DB12424