[3-(2-{(R)-(R)-2-Hydroxy-2-[3-(thiophene-2-sulfonylamino)-phenyl]-ethylamino}-propyl)-1H-indol-7-yloxy]-acetic acid

ID: ALA188196

Chembl Id: CHEMBL188196

PubChem CID: 44396568

Max Phase: Preclinical

Molecular Formula: C25H27N3O6S2

Molecular Weight: 529.64

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C[C@H](Cc1c[nH]c2c(OCC(=O)O)cccc12)NC[C@H](O)c1cccc(NS(=O)(=O)c2cccs2)c1

Standard InChI:  InChI=1S/C25H27N3O6S2/c1-16(11-18-13-27-25-20(18)7-3-8-22(25)34-15-23(30)31)26-14-21(29)17-5-2-6-19(12-17)28-36(32,33)24-9-4-10-35-24/h2-10,12-13,16,21,26-29H,11,14-15H2,1H3,(H,30,31)/t16-,21+/m1/s1

Standard InChI Key:  WATLMDUSELNTHD-IERDGZPVSA-N

Alternative Forms

1. Parent:

   

   ALA188196

   [3-(2-{(R)-(R)-2-Hydroxy-2-[3-(thiophene-2-sulfonylamino)-phenyl]-ethylamino}-propyl)-1H-indol-7-yloxy]-acetic acid

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 529.64

Molecular Weight (Monoisotopic): 529.1341

AlogP: 3.75

#Rotatable Bonds: 12

Polar Surface Area: 140.75

Molecular Species: ZWITTERION

HBA: 7

HBD: 5

#RO5 Violations: 1

HBA (Lipinski): 9

HBD (Lipinski): 5

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 3.57

CX Basic pKa: 9.85

CX LogP: 0.70

CX LogD: -0.02

Aromatic Rings: 4

Heavy Atoms: 36

QED Weighted: 0.19

Np Likeness Score: -1.22

References

1. Mizuno K, Sawa M, Harada H, Tateishi H, Oue M, Tsujiuchi H, Furutani Y, Kato S..  (2004)  Tryptamine-based human beta3-adrenergic receptor agonists. Part 1: SAR studies of the 7-position of the indole ring.,  14  (24): [PMID:15546707] [10.1016/j.bmcl.2004.10.035]

2. Senthil Kumar P, Bharatam PV..  (2010)  Comparative 3D QSAR study on β(1)-, β(2)-, and β(3)-adrenoceptor agonists.,  19  (9): [PMID:21170122] [10.1007/s00044-009-9257-x]

Source

Source(1):

• Scientific Literature