2-(2-hydroxybenzoyl)-N-phenylhydrazinecarbothioamide

ID: ALA3633780

PubChem CID: 2305168

Max Phase: Preclinical

Molecular Formula: C14H13N3O2S

Molecular Weight: 287.34

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(NNC(=S)Nc1ccccc1)c1ccccc1O

Standard InChI:  InChI=1S/C14H13N3O2S/c18-12-9-5-4-8-11(12)13(19)16-17-14(20)15-10-6-2-1-3-7-10/h1-9,18H,(H,16,19)(H2,15,17,20)

Standard InChI Key:  AZCYPCFHNBZJNB-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 20 21  0  0  0  0  0  0  0  0999 V2000
    1.2990   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2990    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5972   -1.5031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5951   -3.0039    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6375   -0.9049    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8933   -3.7570    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8912   -5.2578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8509   -5.8560    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1894   -6.0109    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3383    1.3500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1872   -7.5117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4836   -8.2663    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4784   -9.7663    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1768  -10.5118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8804   -9.7573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8856   -8.2573    0.0000 C   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  2  0
 11 13  1  0
  4 14  1  0
 13 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 15  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3633780

   2-(2-Hydroxybenzoyl)-N-phenylhydrazinecarbothioamide

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 287.34

Molecular Weight (Monoisotopic): 287.0728

AlogP: 2.02

#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: 3.38

CX LogD: 3.30

Aromatic Rings: 2

Heavy Atoms: 20

QED Weighted: 0.50

Np Likeness Score: -1.72

References

1. Işık S, Vullo D, Durdagi S, Ekinci D, Şentürk M, Çetin A, Şentürk E, Supuran CT..  (2015)  Interaction of carbonic anhydrase isozymes I, II, and IX with some pyridine and phenol hydrazinecarbothioamide derivatives.,  25  (23): [PMID:26520662] [10.1016/j.bmcl.2015.10.021]

2. 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]

3. 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