3-Benzyl-5-(4-{3-dimethylaminopropoxy}benzylidene)-2-thioxothiazolidin-4-one

ID: ALA2062725

PubChem CID: 70694835

Max Phase: Preclinical

Molecular Formula: C22H24N2O2S2

Molecular Weight: 412.58

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CN(C)CCCOc1ccc(/C=C2\SC(=S)N(Cc3ccccc3)C2=O)cc1

Standard InChI:  InChI=1S/C22H24N2O2S2/c1-23(2)13-6-14-26-19-11-9-17(10-12-19)15-20-21(25)24(22(27)28-20)16-18-7-4-3-5-8-18/h3-5,7-12,15H,6,13-14,16H2,1-2H3/b20-15-

Standard InChI Key:  RVLONQCLKZONHP-HKWRFOASSA-N

Molfile:  

     RDKit          2D

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   15.5139  -20.5273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0971  -21.2376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5039  -21.9517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3273  -21.9565    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7422  -21.2413    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3331  -20.5303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1052  -19.8105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2801  -19.8061    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.8020  -19.1337    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0163  -19.3842    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0115  -20.2095    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   13.7949  -20.4685    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0462  -21.2544    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   14.0630  -18.3510    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.2979  -18.9786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5874  -19.3982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8698  -18.9913    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1598  -19.4102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1674  -20.2360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8910  -20.6414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5980  -20.2201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4576  -20.6566    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.7385  -20.2519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0286  -20.6725    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3095  -20.2679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5997  -20.6884    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.8806  -20.2838    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6089  -21.5134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  9 14  2  0
  1  7  1  0
 10 15  2  0
  3  4  2  0
 15 16  1  0
  7  8  1  0
 16 17  2  0
  8  9  1  0
 17 18  1  0
 18 19  2  0
  4  5  1  0
 19 20  1  0
  2  3  1  0
 20 21  2  0
 21 16  1  0
  5  6  2  0
 19 22  1  0
  9 10  1  0
 22 23  1  0
 10 11  1  0
 23 24  1  0
 11 12  1  0
 24 25  1  0
 12  8  1  0
 25 26  1  0
  6  1  1  0
 26 27  1  0
 12 13  2  0
 26 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2062725

   (5Z)-3-benzyl-5-[[4-[3-(dimethylamino)propoxy]phenyl]methylidene]-2-sulfanylidene-1,3-thiazolidin-4-one

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: 412.58

Molecular Weight (Monoisotopic): 412.1279

AlogP: 4.42

#Rotatable Bonds: 8

Polar Surface Area: 32.78

Molecular Species: BASE

HBA: 5

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 9.26

CX LogP: 4.61

CX LogD: 2.76

Aromatic Rings: 2

Heavy Atoms: 28

QED Weighted: 0.36

Np Likeness Score: -1.61

References

1. Robertson MJ, Hadzic G, Ambrus J, Pomè DY, Hyde E, Whiting A, Mariana A, von Kleist L, Chau N, Haucke V, Robinson PJ, McCluskey A..  (2012)  The Rhodadyns, a New Class of Small Molecule Inhibitors of Dynamin GTPase Activity.,  3  (5): [PMID:24900478] [10.1021/ml200284s]

Source

Source(1):

• Scientific Literature