1-(4-Hydroxybenzoyl)-4-(4-nitrophenyl)-3-thiosemicarbazide

ID: ALA4521270

PubChem CID: 155542477

Max Phase: Preclinical

Molecular Formula: C14H12N4O4S

Molecular Weight: 332.34

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=C(NNC(=S)Nc1ccc([N+](=O)[O-])cc1)c1ccc(O)cc1

Standard InChI:  InChI=1S/C14H12N4O4S/c19-12-7-1-9(2-8-12)13(20)16-17-14(23)15-10-3-5-11(6-4-10)18(21)22/h1-8,19H,(H,16,20)(H2,15,17,23)

Standard InChI Key:  RQTZTUCAPVPJDY-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 23 24  0  0  0  0  0  0  0  0999 V2000
   13.2140   -7.8623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2128   -8.6819    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9209   -9.0908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6305   -8.6814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6277   -7.8587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9191   -7.4535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3339   -7.4475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0431   -7.8534    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.3308   -6.6303    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.7493   -7.4421    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.4585   -7.8481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1647   -7.4368    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.4616   -8.6653    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   18.8739   -7.8427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8741   -8.6600    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5826   -9.0658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2897   -8.6545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2840   -7.8331    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5750   -7.4310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5048   -9.0899    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.9997   -9.0597    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.7054   -8.6475    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.0039   -9.8768    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  1  1  0
  5  7  1  0
  7  8  1  0
  7  9  2  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  2  0
 12 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 14  1  0
  2 20  1  0
 21 22  2  0
 21 23  1  0
 17 21  1  0
M  CHG  2  21   1  23  -1
M  END

Alternative Forms

1. Parent:

   

   ALA4521270

   ---

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: 332.34

Molecular Weight (Monoisotopic): 332.0579

AlogP: 1.93

#Rotatable Bonds: 3

Polar Surface Area: 116.53

Molecular Species: NEUTRAL

HBA: 5

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.39

CX Basic pKa: ┄

CX LogP: 2.67

CX LogD: 2.63

Aromatic Rings: 2

Heavy Atoms: 23

QED Weighted: 0.39

Np Likeness Score: -1.86

References

1. Ameryckx A, Thabault L, Pochet L, Leimanis S, Poupaert JH, Wouters J, Joris B, Van Bambeke F, Frédérick R..  (2018)  1-(2-Hydroxybenzoyl)-thiosemicarbazides are promising antimicrobial agents targeting d-alanine-d-alanine ligase in bacterio.,  159  [PMID:30300845] [10.1016/j.ejmech.2018.09.067]

Source

Source(1):

• Scientific Literature