Rac-7-((R)-2-((1S,2S)-bi(cyclopentan)-2-ylamino)-1-hydroxyethyl)-4-hydroxybenzo[d]thiazol-2(3H)-one

ID: ALA3323653

PubChem CID: 118710935

Max Phase: Preclinical

Molecular Formula: C19H26N2O3S

Molecular Weight: 362.50

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=c1[nH]c2c(O)ccc([C@@H](O)CN[C@H]3CCC[C@H]3C3CCCC3)c2s1

Standard InChI:  InChI=1S/C19H26N2O3S/c22-15-9-8-13(18-17(15)21-19(24)25-18)16(23)10-20-14-7-3-6-12(14)11-4-1-2-5-11/h8-9,11-12,14,16,20,22-23H,1-7,10H2,(H,21,24)/t12-,14-,16-/m0/s1

Standard InChI Key:  LMKMYJGZBLESNG-NOLJZWGESA-N

Molfile:  

     RDKit          2D

 25 28  0  0  0  0  0  0  0  0999 V2000
    0.9694  -12.7248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9683  -13.5522    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6830  -13.9650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6812  -12.3121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3966  -12.7211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3969  -13.5522    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1873  -13.8088    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6756  -13.1362    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1869  -12.4642    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.6788  -11.4871    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3920  -11.0724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9631  -11.0767    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3895  -10.2474    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1027   -9.8328    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8586  -10.1671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4088   -9.5524    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9941   -8.8390    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1877   -9.0131    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5006  -13.1359    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6832  -14.7900    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0323  -10.9736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4836  -11.5910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8980  -12.3044    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7046  -12.1306    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7885  -11.3100    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  1
 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  1
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 21  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3323653

   ---

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: 362.50

Molecular Weight (Monoisotopic): 362.1664

AlogP: 3.28

#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: 6.98

CX Basic pKa: 9.94

CX LogP: 2.36

CX LogD: 2.27

Aromatic Rings: 2

Heavy Atoms: 25

QED Weighted: 0.66

Np Likeness Score: 0.41

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]

2. 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