(R)-2-(2,5-dimethylthiazol-4-yl)-N-(4-(2-(2-hydroxy-2-(pyridin-3-yl)ethylamino)ethyl)phenyl)acetamide

ID: ALA1089053

PubChem CID: 46845697

Max Phase: Preclinical

Molecular Formula: C22H26N4O2S

Molecular Weight: 410.54

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1nc(CC(=O)Nc2ccc(CCNC[C@H](O)c3cccnc3)cc2)c(C)s1

Standard InChI:  InChI=1S/C22H26N4O2S/c1-15-20(25-16(2)29-15)12-22(28)26-19-7-5-17(6-8-19)9-11-24-14-21(27)18-4-3-10-23-13-18/h3-8,10,13,21,24,27H,9,11-12,14H2,1-2H3,(H,26,28)/t21-/m0/s1

Standard InChI Key:  IZXXELCHQWNDKX-NRFANRHFSA-N

Molfile:  

     RDKit          2D

 29 31  0  0  0  0  0  0  0  0999 V2000
   -3.2431   -7.4500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2443   -8.2773    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5294   -8.6902    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8130   -8.2769    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8159   -7.4463    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5312   -7.0372    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1029   -7.0311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3869   -7.4409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1061   -6.2061    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3260   -7.0258    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0420   -7.4356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7549   -7.0204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4709   -7.4302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4712   -8.2552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1863   -8.6650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9002   -8.2497    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8945   -7.4205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1787   -7.0145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6168   -8.6586    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.3292   -8.2424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3250   -7.4175    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0457   -8.6513    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7581   -8.2352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5103   -8.5633    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0592   -7.9474    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    7.6430   -7.2350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8370   -7.4107    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.6869   -9.3692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9747   -6.4796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  5  7  1  0
 14 15  1  0
  3  4  2  0
 15 16  2  0
  7  8  1  0
 16 17  1  0
 17 18  2  0
 18 13  1  0
  7  9  1  1
 16 19  1  0
  4  5  1  0
 19 20  1  0
  8 10  1  0
 20 21  2  0
  2  3  1  0
 20 22  1  0
 10 11  1  0
 22 23  1  0
 23 24  2  0
  5  6  2  0
 11 12  1  0
  6  1  1  0
 12 13  1  0
 24 25  1  0
 25 26  1  0
 26 27  2  0
 27 23  1  0
  1  2  2  0
 24 28  1  0
 13 14  2  0
 26 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1089053

   (R)-2-(2,5-dimethylthiazol-4-yl)-N-(4-(2-(2-hydroxy-2-(pyridin-3-yl)ethylamino)ethyl)phenyl)acetamide

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: 410.54

Molecular Weight (Monoisotopic): 410.1776

AlogP: 3.20

#Rotatable Bonds: 9

Polar Surface Area: 87.14

Molecular Species: BASE

HBA: 6

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.69

CX Basic pKa: 9.45

CX LogP: 2.58

CX LogD: 0.55

Aromatic Rings: 3

Heavy Atoms: 29

QED Weighted: 0.47

Np Likeness Score: -1.46

References

1. Goble SD, Wang L, Howell KL, Bansal A, Berger R, Brockunier L, DiSalvo J, Feighner S, Harper B, He J, Hurley A, Hreniuk D, Parmee E, Robbins M, Salituro G, Sanfiz A, Streckfuss E, Watkins E, Weber AE, Struthers M, Edmondson SD..  (2010)  Heterocyclic acetamide and benzamide derivatives as potent and selective beta3-adrenergic receptor agonists with improved rodent pharmacokinetic profiles.,  20  (6): [PMID:20181479] [10.1016/j.bmcl.2010.01.130]

Source

Source(1):

• Scientific Literature