N-(4-(2-chlorobenzamido)-3-methoxyphenyl)benzofuran-2-carboxamide

ID: ALA571036

PubChem CID: 1287123

Max Phase: Preclinical

Molecular Formula: C23H17ClN2O4

Molecular Weight: 420.85

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cc(NC(=O)c2cc3ccccc3o2)ccc1NC(=O)c1ccccc1Cl

Standard InChI:  InChI=1S/C23H17ClN2O4/c1-29-20-13-15(25-23(28)21-12-14-6-2-5-9-19(14)30-21)10-11-18(20)26-22(27)16-7-3-4-8-17(16)24/h2-13H,1H3,(H,25,28)(H,26,27)

Standard InChI Key:  ZOFOQKATSBUOJM-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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    0.4046  -15.6976    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2290  -15.6988    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6403  -14.9866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2285  -14.2727    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4010  -14.2756    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0066  -14.9884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6415  -16.4145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2279  -17.1296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4664  -14.9868    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8793  -15.7023    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7054  -15.7026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4661  -16.4176    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1149  -16.4187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9404  -16.4192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3544  -15.7034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9371  -14.9855    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1130  -14.9884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7002  -17.1332    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -0.8327  -14.9908    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2436  -15.7075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.8284  -16.4217    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5586  -15.0437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5546  -16.3803    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3411  -16.1275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3425  -15.3047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0546  -14.8964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7658  -15.3096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7604  -16.1355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0477  -16.5402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 14 15  2  0
  3  4  2  0
 15 16  1  0
  7  8  1  0
 16 17  2  0
 17 11  1  0
 13 18  1  0
  3  9  1  0
  6 19  1  0
  4  5  1  0
 19 20  1  0
  9 10  1  0
 20 21  1  0
  2  3  1  0
 20 22  2  0
 21 23  2  0
 10 11  1  0
  5  6  2  0
 23 26  1  0
 25 24  1  0
 24 21  1  0
 10 12  2  0
  6  1  1  0
 25 26  2  0
 11 13  2  0
 26 27  1  0
  1  2  2  0
 27 28  2  0
 13 14  1  0
 28 29  1  0
  2  7  1  0
 29 30  2  0
 30 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA571036

   N-[4-[(2-chlorobenzoyl)amino]-3-methoxy-phenyl]benzofuran-2-carboxamide

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: 420.85

Molecular Weight (Monoisotopic): 420.0877

AlogP: 5.60

#Rotatable Bonds: 5

Polar Surface Area: 80.57

Molecular Species: NEUTRAL

HBA: 4

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 4.68

CX LogD: 4.68

Aromatic Rings: 4

Heavy Atoms: 30

QED Weighted: 0.44

Np Likeness Score: -1.65

References

1. Gupta RK, Thakur TS, Desiraju GR, Tyagi JS..  (2009)  Structure-based design of DevR inhibitor active against nonreplicating Mycobacterium tuberculosis.,  52  (20): [PMID:19827833] [10.1021/jm900358q]

Source

Source(1):

• Scientific Literature