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

ID: ALA2062753

PubChem CID: 60150578

Max Phase: Preclinical

Molecular Formula: C18H22N2O2S2

Molecular Weight: 362.52

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C=CCN1C(=O)/C(=C/c2ccc(OCCCN(C)C)cc2)SC1=S

Standard InChI:  InChI=1S/C18H22N2O2S2/c1-4-10-20-17(21)16(24-18(20)23)13-14-6-8-15(9-7-14)22-12-5-11-19(2)3/h4,6-9,13H,1,5,10-12H2,2-3H3/b16-13-

Standard InChI Key:  XSXKOIMDNZRKRL-SSZFMOIBSA-N

Molfile:  

     RDKit          2D

 24 25  0  0  0  0  0  0  0  0999 V2000
    0.5753  -14.0476    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3945  -14.0506    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1666  -13.3308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6584  -13.3264    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1366  -12.6541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9222  -12.9045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9270  -13.7300    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1437  -13.9890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8924  -14.7747    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8756  -11.8713    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6407  -12.4990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3511  -12.9185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0688  -12.5117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7787  -12.9305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7711  -13.7564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0476  -14.1617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3405  -13.7405    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4810  -14.1769    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2008  -13.7724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9160  -14.1928    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6304  -13.7883    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3456  -14.2088    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0599  -13.8043    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3298  -15.0338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 11 12  1  0
  3  4  1  0
 12 13  2  0
  5  6  1  0
 13 14  1  0
  6  7  1  0
 14 15  2  0
  7  8  1  0
 15 16  1  0
  8  4  1  0
 16 17  2  0
 17 12  1  0
  4  5  1  0
 15 18  1  0
  8  9  2  0
 18 19  1  0
 19 20  1  0
  5 10  2  0
 20 21  1  0
  1  3  1  0
 21 22  1  0
  6 11  2  0
 22 23  1  0
  2  1  2  0
 22 24  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2062753

   (5Z)-5-[[4-[3-(dimethylamino)propoxy]phenyl]methylidene]-3-prop-2-enyl-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: 362.52

Molecular Weight (Monoisotopic): 362.1123

AlogP: 3.40

#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: 3.62

CX LogD: 1.76

Aromatic Rings: 1

Heavy Atoms: 24

QED Weighted: 0.31

Np Likeness Score: -1.71

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