Methanesulfonic acid 3-(2-{(R)-(R)-2-hydroxy-2-[3-(thiophene-2-sulfonylamino)-phenyl]-ethylamino}-propyl)-1H-indol-7-yl ester

ID: ALA184407

Chembl Id: CHEMBL184407

PubChem CID: 11432806

Max Phase: Preclinical

Molecular Formula: C24H27N3O6S3

Molecular Weight: 549.70

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C24H27N3O6S3/c1-16(12-18-14-26-24-20(18)8-4-9-22(24)33-35(2,29)30)25-15-21(28)17-6-3-7-19(13-17)27-36(31,32)23-10-5-11-34-23/h3-11,13-14,16,21,25-28H,12,15H2,1-2H3/t16-,21+/m1/s1

Standard InChI Key:  ATOBZBFTPJRCNY-IERDGZPVSA-N

Alternative Forms

1. Parent:

   

   ALA184407

   Methanesulfonic acid 3-(2-{(R)-(R)-2-hydroxy-2-[3-(thiophene-2-sulfonylamino)-phenyl]-ethylamino}-propyl)-1H-indol-7-yl ester

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: 549.70

Molecular Weight (Monoisotopic): 549.1062

AlogP: 3.62

#Rotatable Bonds: 11

Polar Surface Area: 137.59

Molecular Species: ZWITTERION

HBA: 8

HBD: 4

#RO5 Violations: 1

HBA (Lipinski): 9

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 6.31

CX Basic pKa: 9.82

CX LogP: 1.88

CX LogD: 1.85

Aromatic Rings: 4

Heavy Atoms: 36

QED Weighted: 0.21

Np Likeness Score: -1.18

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. Sawa M, Tateishi H, Mizuno K, Harada H, Oue M, Tsujiuchi H, Furutani Y, Kato S..  (2004)  Tryptamine-based human beta3-adrenergic receptor agonists. Part 2: SAR of the methylene derivatives.,  14  (24): [PMID:15546708] [10.1016/j.bmcl.2004.09.054]

3. 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