5-((5-(2,3-dimethyl-4-nitrophenyl)furan-2-yl)methylene)-2-iminothiazolidin-4-one

ID: ALA4536515

PubChem CID: 155548241

Max Phase: Preclinical

Molecular Formula: C16H13N3O4S

Molecular Weight: 343.36

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  Cc1c(-c2ccc(/C=C3/SC(=N)NC3=O)o2)ccc([N+](=O)[O-])c1C

Standard InChI:  InChI=1S/C16H13N3O4S/c1-8-9(2)12(19(21)22)5-4-11(8)13-6-3-10(23-13)7-14-15(20)18-16(17)24-14/h3-7H,1-2H3,(H2,17,18,20)/b14-7+

Standard InChI Key:  VMHDKSJEGBWITL-VGOFMYFVSA-N

Molfile:  

 
     RDKit          2D

 24 26  0  0  0  0  0  0  0  0999 V2000
    7.4086   -1.7755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9958   -2.4832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3988   -3.1905    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2184   -3.1952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6335   -2.4869    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2241   -1.7785    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1732   -2.4793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6929   -1.8111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9100   -2.0586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9048   -2.8800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6845   -3.1373    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2407   -3.3603    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4921   -3.0191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3210   -2.2156    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5047   -2.1251    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1676   -2.8738    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7756   -3.4284    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.8748   -1.6110    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3674   -3.0394    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.0029   -1.0661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6339   -1.0714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4533   -2.4864    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.8640   -1.7800    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.8597   -3.1954    0.0000 O   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
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11  7  1  0
  2  7  1  0
 10 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 13  1  0
 14 18  2  0
 16 19  2  0
  1 20  1  0
  6 21  1  0
 22 23  2  0
 22 24  1  0
  5 22  1  0
M  CHG  2  22   1  24  -1
M  END

Alternative Forms

1. Parent:

   

   ALA4536515

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 343.36

Molecular Weight (Monoisotopic): 343.0627

AlogP: 3.61

#Rotatable Bonds: 3

Polar Surface Area: 109.23

Molecular Species: NEUTRAL

HBA: 6

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 10.85

CX Basic pKa: 1.47

CX LogP: 3.46

CX LogD: 3.46

Aromatic Rings: 2

Heavy Atoms: 24

QED Weighted: 0.50

Np Likeness Score: -1.50

References

1. Wang Y, Dou X, Jiang L, Jin H, Zhang L, Zhang L, Liu Z..  (2019)  Discovery of novel glycogen synthase kinase-3α inhibitors: Structure-based virtual screening, preliminary SAR and biological evaluation for treatment of acute myeloid leukemia.,  171  [PMID:30925338] [10.1016/j.ejmech.2019.03.039]

Source

Source(1):

• Scientific Literature