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

ID: ALA183122

PubChem CID: 44391411

Max Phase: Preclinical

Molecular Formula: C20H18Cl2N2O4

Molecular Weight: 421.28

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C20H18Cl2N2O4/c1-10(2)14-9-23-17-5-4-12(8-13(14)17)28-18-15(21)6-11(7-16(18)22)24-19(25)20(26)27-3/h4-10,23H,1-3H3,(H,24,25)

Standard InChI Key:  CCTYHQGZHMQRSN-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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    0.2875    0.3375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5750    0.3208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8458   -0.0792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1792   -0.4792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3625   -0.7500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3000   -0.4875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0000    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7375   -0.4875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4625   -0.9000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9000   -0.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5750   -0.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7250    0.3458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0167   -0.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4208    0.7500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8625    0.7375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1458    0.3208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1625    0.3500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9000   -1.7167    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6125    1.3750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8625   -0.9167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0000    1.5750    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -0.4208   -0.9042    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -1.1458   -0.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6167   -0.4792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4208    1.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0625    1.9750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3250   -0.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2 15  1  0
  3  1  1  0
  4  1  2  0
  5 10  1  0
  6  4  1  0
  7  2  2  0
  8  2  1  0
  9 13  1  0
 10  9  1  0
 11  5  1  0
 12  3  2  0
 13  8  2  0
 14  7  1  0
 15 17  1  0
 16  3  1  0
 17 16  2  0
 18  5  2  0
 19 11  2  0
 20  1  1  0
 21 12  1  0
 22  8  1  0
 23  7  1  0
 24 17  1  0
 25 11  1  0
 26 20  1  0
 27 20  1  0
 28 25  1  0
  6 12  1  0
 24 21  2  0
  9 14  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA183122

   methyl 2-[3,5-dichloro-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: 421.28

Molecular Weight (Monoisotopic): 420.0644

AlogP: 5.50

#Rotatable Bonds: 4

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: 10.66

CX Basic pKa: ┄

CX LogP: 5.60

CX LogD: 5.60

Aromatic Rings: 3

Heavy Atoms: 28

QED Weighted: 0.43

Np Likeness Score: -0.68

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