ethyl 2-(5-((5-(2-chloro-5-nitrophenyl)furan-2-yl)methylene)-2,4-dioxothiazolidin-3-yl)acetate

ID: ALA4467990

PubChem CID: 2271641

Max Phase: Preclinical

Molecular Formula: C18H13ClN2O7S

Molecular Weight: 436.83

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CCOC(=O)CN1C(=O)S/C(=C\c2ccc(-c3cc([N+](=O)[O-])ccc3Cl)o2)C1=O

Standard InChI:  InChI=1S/C18H13ClN2O7S/c1-2-27-16(22)9-20-17(23)15(29-18(20)24)8-11-4-6-14(28-11)12-7-10(21(25)26)3-5-13(12)19/h3-8H,2,9H2,1H3/b15-8-

Standard InChI Key:  NDHQVRYITFMYOS-NVNXTCNLSA-N

Molfile:  

 
     RDKit          2D

 29 31  0  0  0  0  0  0  0  0999 V2000
   13.3129   -7.6045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5214   -7.8135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9431   -7.2351    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.1562   -6.4477    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6084   -5.8413    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8100   -6.0120    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.1994   -5.4642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2875   -4.6496    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.4756   -6.7593    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6652   -6.6712    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    9.4944   -5.8728    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7471   -5.5425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0880   -6.0185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3108   -5.7680    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.0880   -6.8357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3108   -7.0904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8265   -6.4271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8842   -7.4643    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.9436   -6.2387    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0125   -6.4286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6056   -5.7187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7892   -5.7171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3787   -6.4248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7906   -7.1354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6057   -7.1335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0160   -5.0120    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    4.3816   -7.8456    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.7916   -8.5524    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5644   -7.8472    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  6  9  1  0
  9 10  1  0
 10 11  1  0
  7 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 13 15  2  0
 15 16  1  0
 16 17  2  0
 14 17  1  0
  9 18  2  0
  4 19  2  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 20  1  0
 17 20  1  0
 21 26  1  0
 27 28  2  0
 27 29  1  0
 24 27  1  0
M  CHG  2  27   1  29  -1
M  END

Alternative Forms

1. Parent:

   

   ALA4467990

   ethyl 2-[(5Z)-5-[[5-(2-chloro-5-nitrophenyl)furan-2-yl]methylidene]-2,4-dioxo-1,3-thiazolidin-3-yl]acetate

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: 436.83

Molecular Weight (Monoisotopic): 436.0132

AlogP: 4.11

#Rotatable Bonds: 6

Polar Surface Area: 119.96

Molecular Species: NEUTRAL

HBA: 8

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 3.23

CX LogD: 3.23

Aromatic Rings: 2

Heavy Atoms: 29

QED Weighted: 0.29

Np Likeness Score: -2.07

References

1. Hansen SW, Erichsen MN, Fu B, Bjørn-Yoshimoto WE, Abrahamsen B, Hansen JC, Jensen AA, Bunch L..  (2016)  Identification of a New Class of Selective Excitatory Amino Acid Transporter Subtype 1 (EAAT1) Inhibitors Followed by a Structure-Activity Relationship Study.,  59  (19): [PMID:27626828] [10.1021/acs.jmedchem.6b01058]

Source

Source(1):

• Scientific Literature