4-(4-Fluorophenyl)-1-(2-hydroxybenzoyl)-3-thiosemicarbazide

ID: ALA4531935

Cas Number: 343-70-4

PubChem CID: 681196

Max Phase: Preclinical

Molecular Formula: C14H12FN3O2S

Molecular Weight: 305.33

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=C(NNC(=S)Nc1ccc(F)cc1)c1ccccc1O

Standard InChI:  InChI=1S/C14H12FN3O2S/c15-9-5-7-10(8-6-9)16-14(21)18-17-13(20)11-3-1-2-4-12(11)19/h1-8,19H,(H,17,20)(H2,16,18,21)

Standard InChI Key:  HAWQFTQKDAUJNE-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 21 22  0  0  0  0  0  0  0  0999 V2000
   20.9814  -17.1486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9803  -17.9681    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.6883  -18.3771    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.3980  -17.9677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.3951  -17.1450    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.6865  -16.7397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.1013  -16.7337    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.8106  -17.1397    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   23.0982  -15.9166    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.5167  -16.7284    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   25.2260  -17.1343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.9321  -16.7231    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   25.2290  -17.9515    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   26.6414  -17.1290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.6416  -17.9463    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.3500  -18.3521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.0571  -17.9408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.0514  -17.1194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.3424  -16.7172    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.1063  -18.3751    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.7669  -18.3458    0.0000 F   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
 17 21  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4531935

   N-(4-fluorophenyl)-2-(2-hydroxybenzoyl)hydrazinecarbothioamide

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: 305.33

Molecular Weight (Monoisotopic): 305.0634

AlogP: 2.16

#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: 3.52

CX LogD: 3.44

Aromatic Rings: 2

Heavy Atoms: 21

QED Weighted: 0.51

Np Likeness Score: -2.06

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