4-(3,4-Dichlorophenyl)-1-(2-hydroxybenzoyl)-3-thiosemicarbazide

ID: ALA4476621

PubChem CID: 24424330

Max Phase: Preclinical

Molecular Formula: C14H11Cl2N3O2S

Molecular Weight: 356.23

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=C(NNC(=S)Nc1ccc(Cl)c(Cl)c1)c1ccccc1O

Standard InChI:  InChI=1S/C14H11Cl2N3O2S/c15-10-6-5-8(7-11(10)16)17-14(22)19-18-13(21)9-3-1-2-4-12(9)20/h1-7,20H,(H,18,21)(H2,17,19,22)

Standard InChI Key:  FNTHJTUPRVAXFZ-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 22 23  0  0  0  0  0  0  0  0999 V2000
   39.5952  -17.1156    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.5941  -17.9351    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.3021  -18.3441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.0118  -17.9346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.0089  -17.1120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.3003  -16.7067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.7151  -16.7007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.4244  -17.1066    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   41.7120  -15.8835    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   43.1305  -16.6954    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   43.8398  -17.1013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   44.5459  -16.6901    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   43.8428  -17.9185    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   45.2552  -17.0960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   45.2554  -17.9132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   45.9638  -18.3191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   46.6709  -17.9078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   46.6652  -17.0864    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   45.9562  -16.6842    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.7201  -18.3421    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   45.9665  -19.1363    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   47.3807  -18.3128    0.0000 Cl  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
  4 20  1  0
 16 21  1  0
 17 22  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4476621

   1-(3,4-Dichlorophenyl)-3-[(2-hydroxybenzoyl)amino]thiourea

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: 356.23

Molecular Weight (Monoisotopic): 354.9949

AlogP: 3.33

#Rotatable Bonds: 2

Polar Surface Area: 73.39

Molecular Species: NEUTRAL

HBA: 3

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.07

CX Basic pKa: ┄

CX LogP: 4.59

CX LogD: 4.50

Aromatic Rings: 2

Heavy Atoms: 22

QED Weighted: 0.49

Np Likeness Score: -2.05

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]

2. Ameryckx A,Pochet L,Wang G,Yildiz E,Saadi BE,Wouters J,Van Bambeke F,Frédérick R.  (2020)  Pharmacomodulations of the benzoyl-thiosemicarbazide scaffold reveal antimicrobial agents targeting d-alanyl-d-alanine ligase in bacterio.,  200  [PMID:32497961] [10.1016/j.ejmech.2020.112444]

Source

Source(1):

• Scientific Literature