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

ID: ALA183057

PubChem CID: 10109471

Max Phase: Preclinical

Molecular Formula: C21H22N2O4

Molecular Weight: 366.42

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C21H22N2O4/c1-5-26-21(25)20(24)23-15-8-12(2)19(13(3)9-15)27-16-6-7-18-17(10-16)14(4)11-22-18/h6-11,22H,5H2,1-4H3,(H,23,24)

Standard InChI Key:  RWEKLGLVVRRTRA-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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   -0.2083    0.4708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8583   -0.6167    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0833    0.4625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3458    0.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8583    0.7208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9667   -0.7542    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3917   -0.7292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2083   -0.3542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5042    0.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2292   -0.3500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0833   -0.3542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9333    0.8833    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2292    0.4833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5042   -0.7625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3708    0.8833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6458    0.4625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6542    0.5000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4167   -1.5542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3708   -0.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6458   -0.3542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1042   -0.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1208    1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9208   -0.7625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4917    1.7208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8292   -0.7000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5292   -0.2792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  9  2  0
  3 12  1  0
  4 16  1  0
  5  6  2  0
  6  4  1  0
  7  1  1  0
  8  1  1  0
  9 15  1  0
 10 14  2  0
 11  7  1  0
 12 20  1  0
 13  2  1  0
 14 11  1  0
 15 11  2  0
 16 17  2  0
 17 13  1  0
 18  1  2  0
 19  8  2  0
 20 21  2  0
 21 17  1  0
 22  8  1  0
 23  6  1  0
 24  9  1  0
 25 10  1  0
 26 22  1  0
 27 26  1  0
 10  2  1  0
 12  4  2  0
  5  3  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA183057

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

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: 366.42

Molecular Weight (Monoisotopic): 366.1580

AlogP: 4.39

#Rotatable Bonds: 4

Polar Surface Area: 80.42

Molecular Species: NEUTRAL

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 10.96

CX Basic pKa: ┄

CX LogP: 5.05

CX LogD: 5.05

Aromatic Rings: 3

Heavy Atoms: 27

QED Weighted: 0.53

Np Likeness Score: -0.81

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