O-benzyl S-1-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl)ethyl carbonodithioate oxalate

ID: ALA3247049

PubChem CID: 12460803

Max Phase: Preclinical

Molecular Formula: C21H18Cl2N2O5S2

Molecular Weight: 423.39

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(O)C(=O)O.S=C(OCc1ccccc1)SC(Cn1ccnc1)c1ccc(Cl)cc1Cl

Standard InChI:  InChI=1S/C19H16Cl2N2OS2.C2H2O4/c20-15-6-7-16(17(21)10-15)18(11-23-9-8-22-13-23)26-19(25)24-12-14-4-2-1-3-5-14;3-1(4)2(5)6/h1-10,13,18H,11-12H2;(H,3,4)(H,5,6)

Standard InChI Key:  DUSHHSTXGFYMHS-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 32 33  0  0  0  0  0  0  0  0999 V2000
   32.6206   -9.3991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.9062   -9.8116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.6206   -8.5741    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   33.3351   -9.8116    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   31.9062  -10.6366    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   31.1917   -9.3991    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.0496  -10.2720    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.0484  -11.0993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.7632  -11.5122    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.4797  -11.0989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.4768  -10.2683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.7614   -9.8592    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.1948  -11.5102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.1961  -12.3352    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   27.9086  -11.0966    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.9073  -10.2716    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   28.5723   -9.7874    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.3161   -9.0032    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.4911   -9.0045    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   27.2375   -9.7895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.9112  -12.7466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.9125  -13.5716    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   28.6250  -12.3330    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.3402  -12.7444    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.7609  -12.3355    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   24.3333   -9.8647    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   30.0540  -12.3308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.7689  -12.7438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.4822  -12.3309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.4814  -11.5050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.7612  -11.0938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.0508  -11.5091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  1  3  2  0
  1  4  1  0
  2  5  2  0
  2  6  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12  7  1  0
 10 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 16  1  0
 14 21  1  0
 21 22  2  0
 21 23  1  0
 23 24  1  0
  9 25  1  0
  7 26  1  0
 24 27  1  0
 27 28  2  0
 28 29  1  0
 29 30  2  0
 30 31  1  0
 31 32  2  0
 32 27  1  0
M  END

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: 423.39

Molecular Weight (Monoisotopic): 422.0081

AlogP: 6.17

#Rotatable Bonds: 6

Polar Surface Area: 27.05

Molecular Species: NEUTRAL

HBA: 5

HBD: ┄

#RO5 Violations: 1

HBA (Lipinski): 3

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: 6.50

CX LogP: 6.52

CX LogD: 6.49

Aromatic Rings: 3

Heavy Atoms: 26

QED Weighted: 0.44

Np Likeness Score: -1.20

References

1. Walker KA, Hirschfeld DR, Marx M..  (1978)  Antimycotic imidazoles. 2. Synthesis and antifungal properties of esters of 1-[2-hydroxy(mercapto)-2-phenylethyl]-1H-imidazoles.,  21  (12): [PMID:722748] [10.1021/jm00210a037]

Source

Source(1):

• Scientific Literature