Methyl 4-(5-nitro-1-benzothiophene-2-amido)benzoate

ID: ALA4754509

Cas Number: 478248-48-5

PubChem CID: 1489068

Max Phase: Preclinical

Molecular Formula: C17H12N2O5S

Molecular Weight: 356.36

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  COC(=O)c1ccc(NC(=O)c2cc3cc([N+](=O)[O-])ccc3s2)cc1

Standard InChI:  InChI=1S/C17H12N2O5S/c1-24-17(21)10-2-4-12(5-3-10)18-16(20)15-9-11-8-13(19(22)23)6-7-14(11)25-15/h2-9H,1H3,(H,18,20)

Standard InChI Key:  SPLIJDWJFSSGOI-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 25 27  0  0  0  0  0  0  0  0999 V2000
   14.9966   -8.4608    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9954   -9.2876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7097   -9.7002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7079   -8.0483    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4228   -8.4572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4277   -9.2830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2146   -9.5337    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   17.6962   -8.8626    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2068   -8.1974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2818   -8.0490    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.5678   -8.4614    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.2816   -7.2245    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.5206   -8.8578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9370   -9.5693    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.9286   -8.1414    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.7531   -8.1365    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1673   -8.8500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9910   -8.8455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3998   -8.1286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9789   -7.4146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1567   -7.4227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.2269   -8.1230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.6442   -8.8340    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.6339   -7.4061    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.4686   -8.8280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  6  2  0
  5  4  2  0
  4  1  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9  5  1  0
 10 11  2  0
 10 12  1  0
  1 10  1  0
  8 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 16  1  0
 22 23  1  0
 22 24  2  0
 19 22  1  0
 23 25  1  0
M  CHG  2  10   1  12  -1
M  END

Alternative Forms

1. Parent:

   

   ALA4754509

   Methyl 4-{[(5-nitro-1-benzothiophen-2-yl)carbonyl]amino}benzenecarboxylate

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 356.36

Molecular Weight (Monoisotopic): 356.0467

AlogP: 3.85

#Rotatable Bonds: 4

Polar Surface Area: 98.54

Molecular Species: NEUTRAL

HBA: 6

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.50

CX Basic pKa: ┄

CX LogP: 4.02

CX LogD: 4.02

Aromatic Rings: 3

Heavy Atoms: 25

QED Weighted: 0.43

Np Likeness Score: -1.90

References

1. Nijampatnam B,Ahirwar P,Pukkanasut P,Womack H,Casals L,Zhang H,Cai X,Michalek SM,Wu H,Velu SE.  (2021)  Discovery of Potent Inhibitors of Streptococcus mutans Biofilm with Antivirulence Activity.,  12  (1): [PMID:33488963] [10.1021/acsmedchemlett.0c00373]

Source

Source(1):

• Scientific Literature