Compound 821

Identifiers

Canonical SMILES:

Cc1cc2CN(CCc2c(C)c1C(=O)N[C@@H](CNC(=O)c1cccs1)C(O)=O)C(=O)c1ccccc1

InChi:

InChI=1S/C27H27N3O5S/c1-16-13-19-15-30(26(33)18-7-4-3-5-8-18)11-10-20(19)17(2)23(16)25(32)29-21(27(34)35)14-28-24(31)22-9-6-12-36-22/h3-9,12-13,21H,10-11,14-15H2,1-2H3,(H,28,31)(H,29,32)(H,34,35)/t21-/m0/s1

InChiKey:
```
AHJSZJJPEGELGL-NRFANRHFSA-N
```

External links

168318069

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.	6b

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	7.10	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	505.17 g/mol
HBA	8
HBD	3
HBA + HBD	11
AlogP	3.62
TPSA	115.81
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	6b	ITAL P20701		Cellular assay	hut-78 cell adhesion assay		pIC50 (half maximal inhibitory concentration, -log10)	7.10

Ta	Name	Drugbank ID
0.5625	N-[2-(2-methyl-1H-indol-3-yl)ethyl]thiophene-2-carboxamide	DB08235
0.5525	Ibodutant	DB12042
0.5320	2-[(1R)-2-carboxy-1-(naphthalen-1-ylmethyl)ethyl]-1,3-dioxo-2,3-dihydro-1H-isoindole-5-carboxylic acid	DB08731
0.5256	2-[(1R)-1-carboxy-2-naphthalen-1-ylethyl]-1,3-dioxo-2,3-dihydro-1H-isoindole-5-carboxylic acid	DB06922
0.5246	PF-00356231	DB03367
0.5244	Encenicline	DB11726
0.5155	(2S,4S,5R)-2-ISOBUTYL-5-(2-THIENYL)-1-[4-(TRIFLUOROMETHYL)BENZOYL]PYRROLIDINE-2,4-DICARBOXYLIC ACID	DB07200
0.5093	2-[(1R)-1-CARBOXY-2-(4-HYDROXYPHENYL)ETHYL]-1,3-DIOXOISOINDOLINE-5-CARBOXYLIC ACID	DB07663
0.4970	Quinaprilat	DB14217
0.4968	Semagacestat	DB12463
0.4880	Icatibant	DB06196
0.4878	Palonosetron	DB00377
0.4863	5-CHLORO-N-((1R,2S)-2-(4-(2-OXOPYRIDIN-1(2H)-YL)BENZAMIDO) CYCLOPENTYL)THIOPHENE-2-CARBOXAMIDE	DB08174
0.4774	(R)-Praziquantel	DB11749
0.4774	Praziquantel	DB01058