N-{(S)-3-[4-(6-Isopropoxy-pyridin-3-yloxy)-phenyl]-1-methyl-propyl}-acetamide

ID: ALA1630715

Cas Number: 1204483-20-4

PubChem CID: 44554862

Max Phase: Preclinical

Molecular Formula: C20H26N2O3

Molecular Weight: 342.44

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(=O)N[C@@H](C)CCc1ccc(Oc2ccc(OC(C)C)nc2)cc1

Standard InChI:  InChI=1S/C20H26N2O3/c1-14(2)24-20-12-11-19(13-21-20)25-18-9-7-17(8-10-18)6-5-15(3)22-16(4)23/h7-15H,5-6H2,1-4H3,(H,22,23)/t15-/m0/s1

Standard InChI Key:  CHLNWUAMDPEDES-HNNXBMFYSA-N

Molfile:  

     RDKit          2D

 25 26  0  0  1  0  0  0  0  0999 V2000
    3.6331   -3.6060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5951   -3.0039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5548   -3.6021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5973   -1.5031    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2990   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2990    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6003    1.4977    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8990    0.7455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2007    1.4909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4972    0.7364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4920   -0.7636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7876   -1.5212    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7802   -3.0220    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0758   -3.7796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.1182   -3.1850    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0685   -5.2804    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  -10.3641   -6.0379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.3582   -7.2379    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  -11.4064   -5.4434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1903   -1.5091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8939   -0.7546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.5000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  1
 16 18  1  0
 18 19  1  0
 19 20  2  0
 19 21  1  0
 13 22  1  0
 22 23  2  0
 23 10  1  0
  8 24  1  0
 24 25  2  0
 25  5  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1630715

   Acetamide, N-[(1S)-1-methyl-3-[4-[[6-(1-methylethoxy)-3-pyridinyl]oxy]phenyl]propyl]-

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: 342.44

Molecular Weight (Monoisotopic): 342.1943

AlogP: 4.12

#Rotatable Bonds: 8

Polar Surface Area: 60.45

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 2.09

CX LogP: 3.56

CX LogD: 3.56

Aromatic Rings: 2

Heavy Atoms: 25

QED Weighted: 0.78

Np Likeness Score: -1.10

References

1. Keil S, Müller M, Zoller G, Haschke G, Schroeter K, Glien M, Ruf S, Focken I, Herling AW, Schmoll D..  (2010)  Identification and synthesis of novel inhibitors of acetyl-CoA carboxylase with in vitro and in vivo efficacy on fat oxidation.,  53  (24): [PMID:21082864] [10.1021/jm101179e]

2.  (2013)  Heterocyclic compounds, processes for their preparation, medicaments comprising these compounds, and the use thereof, 

Source

Source(2):

• Scientific Literature
• BindingDB Database