Methyl 4-chloro-3-{[4-(4morpholinylmethyl)benzoyl]amino}benzoate

ID: ALA569421

PubChem CID: 2212506

Max Phase: Preclinical

Molecular Formula: C20H21ClN2O4

Molecular Weight: 388.85

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COC(=O)c1ccc(Cl)c(NC(=O)c2ccc(CN3CCOCC3)cc2)c1

Standard InChI:  InChI=1S/C20H21ClN2O4/c1-26-20(25)16-6-7-17(21)18(12-16)22-19(24)15-4-2-14(3-5-15)13-23-8-10-27-11-9-23/h2-7,12H,8-11,13H2,1H3,(H,22,24)

Standard InChI Key:  SMGWCVYQXPROOK-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 27 29  0  0  0  0  0  0  0  0999 V2000
    8.5152  -14.1166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5141  -14.9440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2289  -15.3569    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9453  -14.9435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9425  -14.1130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2271  -13.7039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7993  -15.3559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0851  -14.9429    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7986  -16.1809    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0838  -16.5929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6554  -13.6978    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   10.6605  -15.3549    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.3743  -14.9413    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0894  -15.3527    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3730  -14.1163    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.0860  -16.1761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8003  -16.5874    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5151  -16.1737    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5111  -15.3444    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7963  -14.9369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2308  -16.5841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9440  -16.1696    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.6555  -16.5829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3666  -16.1718    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3685  -15.3464    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.6530  -14.9338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9356  -15.3466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
 13 14  1  0
  2  7  1  0
 13 15  2  0
  3  4  2  0
 14 16  2  0
  7  8  2  0
 16 17  1  0
 17 18  2  0
  7  9  1  0
 18 19  1  0
  4  5  1  0
 19 20  2  0
 20 14  1  0
  9 10  1  0
 18 21  1  0
  2  3  1  0
 21 22  1  0
 22 23  1  0
  5 11  1  0
  5  6  2  0
  4 12  1  0
  6  1  1  0
 12 13  1  0
 22 27  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA569421

   Methyl 4-chloro-3-[[4-(morpholinomethyl)benzoyl]amino]benzoate

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: 388.85

Molecular Weight (Monoisotopic): 388.1190

AlogP: 3.21

#Rotatable Bonds: 5

Polar Surface Area: 67.87

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 6.60

CX LogP: 3.40

CX LogD: 3.33

Aromatic Rings: 2

Heavy Atoms: 27

QED Weighted: 0.80

Np Likeness Score: -1.75

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