Compound 481

Identifiers

Canonical SMILES:

Cc1cc2CN(CCc2c(C)c1C(=O)N[C@@H](CNC(=O)c1cccs1)C(O)=O)C(=O)c1ccc2ccoc2c1

InChi:

InChI=1S/C29H27N3O6S/c1-16-12-20-15-32(28(35)19-6-5-18-8-10-38-23(18)13-19)9-7-21(20)17(2)25(16)27(34)31-22(29(36)37)14-30-26(33)24-4-3-11-39-24/h3-6,8,10-13,22H,7,9,14-15H2,1-2H3,(H,30,33)(H,31,34)(H,36,37)/t22-/m0/s1

InChiKey:
```
CSENXZJZYBRUFV-QFIPXVFZSA-N
```

External links

168318200

External search

Bibliography (1)

Publication	Name
Zhong M, Shen W, Barr KJ, Arbitrario JP, Arkin MR, Bui M, Chen T, Cunningham BC, Evanchik MJ, Hanan EJ, Hoch U, Huen K, Hyde J, Kumer JL, Lac T, Lawrence CE, Martell JR, Oslob JD, Paulvannan K, Prabhu S, Silverman JA, Wright J, Yu CH, Zhu J, Flanagan WM. . Discovery of tetrahydroisoquinoline (THIQ) derivatives as potent and orally bioavailable LFA-1/ICAM-1 antagonists. Bioorganic & medicinal chemistry letters.	6q

Publication

Name

Zhong M, Shen W, Barr KJ, Arbitrario JP, Arkin MR, Bui M, Chen T, Cunningham BC, Evanchik MJ, Hanan EJ, Hoch U, Huen K, Hyde J, Kumer JL, Lac T, Lawrence CE, Martell JR, Oslob JD, Paulvannan K, Prabhu S, Silverman JA, Wright J, Yu CH, Zhu J, Flanagan WM. . Discovery of tetrahydroisoquinoline (THIQ) derivatives as potent and orally bioavailable LFA-1/ICAM-1 antagonists. Bioorganic & medicinal chemistry letters.

Pharmacological data

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

Targets

PPI family	Best activity	Diseases	MMoA
LFA / ICAM	8.05	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	545.16 g/mol
HBA	9
HBD	3
HBA + HBD	12
AlogP	3.77
TPSA	128.95
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	0	1	0	0

Pharmacological data

Bibliography	Name	Target	Competition	Assay type	Assay name	Cell line	Activity type	Activity
20655213	6q	ITAL P20701		Cellular assay	hut-78 cell adhesion assay		pIC50 (half maximal inhibitory concentration, -log10)	8.05

Ta	Name	Drugbank ID
0.5498	Lifitegrast	DB11611
0.4978	(2s)-2-[(5-Benzofuran-2-Yl-Thiophen-2-Ylmethyl)-(2,4-Dichloro-Benzoyl)-Amino]-3-Phenyl-Propionic Acid	DB02331
0.4976	Ibodutant	DB12042
0.4919	N-[2-(2-methyl-1H-indol-3-yl)ethyl]thiophene-2-carboxamide	DB08235
0.4641	2-[(1R)-2-carboxy-1-(naphthalen-1-ylmethyl)ethyl]-1,3-dioxo-2,3-dihydro-1H-isoindole-5-carboxylic acid	DB08731
0.4603	Encenicline	DB11726
0.4593	PF-00356231	DB03367
0.4586	2-[(1R)-1-carboxy-2-naphthalen-1-ylethyl]-1,3-dioxo-2,3-dihydro-1H-isoindole-5-carboxylic acid	DB06922
0.4546	(2S,4S,5R)-2-ISOBUTYL-5-(2-THIENYL)-1-[4-(TRIFLUOROMETHYL)BENZOYL]PYRROLIDINE-2,4-DICARBOXYLIC ACID	DB07200
0.4420	Semagacestat	DB12463
0.4402	Icatibant	DB06196
0.4396	5-CHLORO-N-((1R,2S)-2-(4-(2-OXOPYRIDIN-1(2H)-YL)BENZAMIDO) CYCLOPENTYL)THIOPHENE-2-CARBOXAMIDE	DB08174
0.4385	2-[(1R)-1-CARBOXY-2-(4-HYDROXYPHENYL)ETHYL]-1,3-DIOXOISOINDOLINE-5-CARBOXYLIC ACID	DB07663
0.4293	Quinaprilat	DB14217
0.4219	5-Chloro-thiophene-2-carboxylic acid ((3S,4S)-1-{[2-fluoro-4-(2-oxo-2H-pyridin-1-yl)-phenylcarbamoyl]-methyl}-4-hydroxy-pyrrolidin-3-yl)-amide	DB07875