N-[3-Chloro-4-(3-isopropyl-1H-indol-5-yloxy)-5-methyl-phenyl]-oxalamic acid ethyl ester

ID: ALA359647

PubChem CID: 44391408

Max Phase: Preclinical

Molecular Formula: C22H23ClN2O4

Molecular Weight: 414.89

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCOC(=O)C(=O)Nc1cc(C)c(Oc2ccc3[nH]cc(C(C)C)c3c2)c(Cl)c1

Standard InChI:  InChI=1S/C22H23ClN2O4/c1-5-28-22(27)21(26)25-14-8-13(4)20(18(23)9-14)29-15-6-7-19-16(10-15)17(11-24-19)12(2)3/h6-12,24H,5H2,1-4H3,(H,25,26)

Standard InChI Key:  WSTUKPKFASCSPC-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 29 31  0  0  0  0  0  0  0  0999 V2000
   -3.5708    0.5958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7833    0.3458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0583   -0.0667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9667   -0.4542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5708   -0.7375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0792    0.3583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0917   -0.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2542   -0.8792    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6917   -0.8750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5292   -0.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7917    0.7625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7833   -0.4792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8042   -0.8792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6333    0.7625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0708    0.7583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5167    0.3583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3583    0.3458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9542    0.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6917   -1.7000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8208    1.3958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0708   -0.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6333   -0.8917    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -1.3583   -0.4792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4042   -0.4542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7917    1.5958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6333    1.5583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2708    1.9958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1167   -0.8750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8292   -0.4542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  1  2  0
  4  8  1  0
  5  3  1  0
  6 14  1  0
  7  6  2  0
  8 10  1  0
  9  4  1  0
 10 16  1  0
 11  6  1  0
 12  2  2  0
 13  7  1  0
 14 17  1  0
 15  2  1  0
 16 11  2  0
 17 15  2  0
 18  4  2  0
 19  9  2  0
 20  1  1  0
 21 12  1  0
 22  7  1  0
 23 17  1  0
 24  9  1  0
 25 11  1  0
 26 20  1  0
 27 20  1  0
 28 24  1  0
 29 28  1  0
  5 12  1  0
 23 21  2  0
 10 13  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA359647

   ethyl 2-[3-chloro-5-methyl-4-[(3-propan-2-yl-1H-indol-5-yl)oxy]anilino]-2-oxoacetate

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: 414.89

Molecular Weight (Monoisotopic): 414.1346

AlogP: 5.55

#Rotatable Bonds: 5

Polar Surface Area: 80.42

Molecular Species: NEUTRAL

HBA: 4

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 10.81

CX Basic pKa: ┄

CX LogP: 5.87

CX LogD: 5.87

Aromatic Rings: 3

Heavy Atoms: 29

QED Weighted: 0.42

Np Likeness Score: -0.96

References

1. Haning H, Woltering M, Mueller U, Schmidt G, Schmeck C, Voehringer V, Kretschmer A, Pernerstorfer J..  (2005)  Novel heterocyclic thyromimetics.,  15  (7): [PMID:15780617] [10.1016/j.bmcl.2005.02.028]

Source

Source(1):

• Scientific Literature