Tert-butyl N-{[2-(5-nitro-1-benzothiophene-2-amido)phenyl]methyl}carbamate

ID: ALA4752433

PubChem CID: 149553905

Max Phase: Preclinical

Molecular Formula: C21H21N3O5S

Molecular Weight: 427.48

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CC(C)(C)OC(=O)NCc1ccccc1NC(=O)c1cc2cc([N+](=O)[O-])ccc2s1

Standard InChI:  InChI=1S/C21H21N3O5S/c1-21(2,3)29-20(26)22-12-13-6-4-5-7-16(13)23-19(25)18-11-14-10-15(24(27)28)8-9-17(14)30-18/h4-11H,12H2,1-3H3,(H,22,26)(H,23,25)

Standard InChI Key:  ZQWMNJHUNNCCAH-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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   15.2686  -20.7197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2674  -21.5470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9822  -21.9599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9804  -20.3069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6957  -20.7161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7006  -21.5425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4880  -21.7932    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   17.9699  -21.1218    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4802  -20.4561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5534  -20.3076    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.8390  -20.7203    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.5532  -19.4827    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.7949  -21.1169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2115  -21.8289    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.2031  -20.4001    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.0281  -20.3953    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4427  -21.1091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2669  -21.1046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.6759  -20.3872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2548  -19.6729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4320  -19.6809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0129  -18.9703    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4187  -18.2521    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.9995  -17.5416    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4052  -16.8233    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.1746  -17.5493    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.9862  -16.1127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3919  -15.3945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1612  -16.1204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5656  -15.3950    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
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 24 26  2  0
 25 27  1  0
 27 28  1  0
 27 29  1  0
 27 30  1  0
M  CHG  2  10   1  12  -1
M  END

Alternative Forms

1. Parent:

   

   ALA4752433

   ---

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: 427.48

Molecular Weight (Monoisotopic): 427.1202

AlogP: 5.09

#Rotatable Bonds: 5

Polar Surface Area: 110.57

Molecular Species: NEUTRAL

HBA: 6

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 8

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 13.41

CX Basic pKa: ┄

CX LogP: 4.63

CX LogD: 4.63

Aromatic Rings: 3

Heavy Atoms: 30

QED Weighted: 0.44

Np Likeness Score: -1.95

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