4-hydroxy-7-((R)-1-hydroxy-2-((1R,2R)-2-phenylcyclopentylamino)ethyl)benzo[d]thiazol-2(3H)-one

ID: ALA3323659

PubChem CID: 118710941

Max Phase: Preclinical

Molecular Formula: C20H22N2O3S

Molecular Weight: 370.47

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=c1[nH]c2c(O)ccc([C@@H](O)CN[C@@H]3CCC[C@@H]3c3ccccc3)c2s1

Standard InChI:  InChI=1S/C20H22N2O3S/c23-16-10-9-14(19-18(16)22-20(25)26-19)17(24)11-21-15-8-4-7-13(15)12-5-2-1-3-6-12/h1-3,5-6,9-10,13,15,17,21,23-24H,4,7-8,11H2,(H,22,25)/t13-,15-,17+/m1/s1

Standard InChI Key:  IAEPLCQQQMHCHK-UNEWFSDZSA-N

Molfile:  

     RDKit          2D

 26 29  0  0  0  0  0  0  0  0999 V2000
    7.0603  -11.7048    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0591  -12.5243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7672  -12.9333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7654  -11.2959    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4740  -11.7012    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4743  -12.5244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2572  -12.7785    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.7409  -12.1124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2568  -11.4466    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    7.7629  -10.4787    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4694  -10.0680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0540  -10.0723    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.4670   -9.2508    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.1735   -8.8401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9221   -9.1713    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4671   -8.5623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0564   -7.8558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2576   -8.0282    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5581  -12.1121    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7674  -13.7505    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0942   -9.9701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4831  -10.5161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6525  -11.3119    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4294  -11.5664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0372  -11.0188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8681  -10.2166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  6  2  0
  5  4  2  0
  4  1  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9  5  1  0
  4 10  1  0
 10 11  1  0
 10 12  1  1
 11 13  1  0
 14 13  1  6
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 14  1  0
  8 19  2  0
  3 20  1  0
 15 21  1  6
 21 22  2  0
 21 26  1  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA3323659

   ---

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: 370.47

Molecular Weight (Monoisotopic): 370.1351

AlogP: 3.25

#Rotatable Bonds: 5

Polar Surface Area: 85.35

Molecular Species: BASE

HBA: 5

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 6.97

CX Basic pKa: 9.85

CX LogP: 2.34

CX LogD: 2.24

Aromatic Rings: 3

Heavy Atoms: 26

QED Weighted: 0.56

Np Likeness Score: 0.23

References

1. Arnold N, Beattie D, Bradley M, Brearley A, Brown L, Charlton SJ, Fairhurst RA, Farr D, Fozard J, Fullerton J, Gosling M, Hatto J, Janus D, Jones D, Jordan L, Lewis C, Maas J, McCarthy C, Mercer M, Oakman H, Press N, Profit R, Schuerch F, Sykes D, Taylor RJ, Trifilieff A, Tuffnell A..  (2014)  The identification of 7-[(R)-2-((1S,2S)-2-benzyloxycyclopentylamino)-1-hydroxyethyl]-4-hydroxybenzothiazolone as an inhaled long-acting β2-adrenoceptor agonist.,  24  (17): [PMID:25065493] [10.1016/j.bmcl.2014.06.014]

Source

Source(1):

• Scientific Literature