1-Hydroxy-2-(2-chloro-4-isothiocyanato)naphthanilide

ID: ALA3245915

Cas Number: 67728-25-0

PubChem CID: 171858

Max Phase: Preclinical

Molecular Formula: C18H11ClN2O2S

Molecular Weight: 354.82

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(Nc1ccc(N=C=S)cc1Cl)c1ccc2ccccc2c1O

Standard InChI:  InChI=1S/C18H11ClN2O2S/c19-15-9-12(20-10-24)6-8-16(15)21-18(23)14-7-5-11-3-1-2-4-13(11)17(14)22/h1-9,22H,(H,21,23)

Standard InChI Key:  KCFHCMVMIBEPIJ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 24 26  0  0  0  0  0  0  0  0999 V2000
   24.4111  -25.8488    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.4100  -26.6683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.1180  -27.0773    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.1163  -25.4399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.8249  -25.8452    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.8256  -26.6642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.5342  -27.0713    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.2424  -26.6605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.2377  -25.8383    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.5286  -25.4350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.5243  -24.6178    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.9429  -25.4254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.6531  -25.8297    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.9379  -24.6083    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   28.6431  -24.1954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.3515  -24.6019    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.0562  -24.1897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.0517  -23.3717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.3365  -22.9676    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.6347  -23.3821    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.9229  -22.9808    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   30.7563  -22.9578    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   31.4670  -23.3612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.1717  -23.7687    0.0000 S   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  2  0
  8  9  1  0
  9 10  2  0
 10  5  1  0
 10 11  1  0
  9 12  1  0
 12 13  2  0
 12 14  1  0
 14 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
 20 21  1  0
 18 22  1  0
 22 23  2  0
 23 24  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA3245915

   N-(2-Chloro-4-isothiocyanatophenyl)-1-hydroxy-2-naphthamide

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: 354.82

Molecular Weight (Monoisotopic): 354.0230

AlogP: 5.19

#Rotatable Bonds: 3

Polar Surface Area: 61.69

Molecular Species: NEUTRAL

HBA: 4

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 4

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 7.54

CX Basic pKa: ┄

CX LogP: 5.38

CX LogD: 5.14

Aromatic Rings: 3

Heavy Atoms: 24

QED Weighted: 0.50

Np Likeness Score: -1.24

References

1. Dubey SK, Singh AK, Singh H, Sharma S, Iyer RN, Katiyar JC, Goel P, Sen AB..  (1978)  Synthesis of substituted 1-hydroxy-2-naphthanilides as potential cestodicidal agents.,  21  (11): [PMID:722724] [10.1021/jm00209a020]

Source

Source(1):

• Scientific Literature