tert-butyl 2-(5-nitro-1H-indole-2-carboxamido)benzylcarbamate

ID: ALA4744859

PubChem CID: 156676660

Max Phase: Preclinical

Molecular Formula: C21H22N4O5

Molecular Weight: 410.43

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CC(C)(C)OC(=O)NCc1ccccc1NC(=O)c1cc2cc([N+](=O)[O-])ccc2[nH]1

Standard InChI:  InChI=1S/C21H22N4O5/c1-21(2,3)30-20(27)22-12-13-6-4-5-7-16(13)24-19(26)18-11-14-10-15(25(28)29)8-9-17(14)23-18/h4-11,23H,12H2,1-3H3,(H,22,27)(H,24,26)

Standard InChI Key:  NTYMWLSUAYAQCH-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 30 32  0  0  0  0  0  0  0  0999 V2000
   15.4603  -21.2073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4592  -22.0346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1739  -22.4475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1721  -20.7945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8875  -21.2037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8924  -22.0301    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6798  -22.2808    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.1616  -21.6094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6719  -20.9437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7451  -20.7952    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.0307  -21.2078    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.7449  -19.9703    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.9866  -21.6046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4033  -22.3166    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.3948  -20.8877    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.2198  -20.8829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6344  -21.5967    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.4586  -21.5922    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.8677  -20.8748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.4466  -20.1605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6238  -20.1685    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2047  -19.4579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6104  -18.7397    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.1912  -18.0291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5971  -17.3108    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.3664  -18.0369    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.1779  -16.6003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5837  -15.8821    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3531  -16.6080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7574  -15.8826    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:

   

   ALA4744859

   ---

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: 410.43

Molecular Weight (Monoisotopic): 410.1590

AlogP: 4.35

#Rotatable Bonds: 5

Polar Surface Area: 126.36

Molecular Species: NEUTRAL

HBA: 5

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 10.72

CX Basic pKa: ┄

CX LogP: 3.64

CX LogD: 3.64

Aromatic Rings: 3

Heavy Atoms: 30

QED Weighted: 0.43

Np Likeness Score: -1.63

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