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

ID: ALA4565844

PubChem CID: 2287441

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(-c3ccc([N+](=O)[O-])cc3Cl)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)12-5-3-10(21(25)26)7-13(12)19/h3-8H,2,9H2,1H3/b15-8-

Standard InChI Key:  KFNDRVPYEDYCCB-NVNXTCNLSA-N

Molfile:  

 
     RDKit          2D

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   13.4367   -8.3143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6452   -8.5234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0669   -7.9450    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.2800   -7.1576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7322   -6.5512    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9338   -6.7219    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.3232   -6.1741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4113   -5.3595    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.5994   -7.4692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7890   -7.3811    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    9.6182   -6.5827    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8709   -6.2524    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2118   -6.7284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4346   -6.4779    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.2118   -7.5456    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4346   -7.8003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9503   -7.1370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0080   -8.1742    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.0674   -6.9486    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1364   -7.1385    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7294   -6.4286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9130   -6.4270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5025   -7.1346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9145   -7.8453    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7295   -7.8434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1398   -5.7219    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.6807   -7.1367    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2720   -7.8444    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2722   -6.4290    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
 23 27  1  0
M  CHG  2  27   1  29  -1
M  END

Alternative Forms

1. Parent:

   

   ALA4565844

   ethyl 2-[(5Z)-5-[[5-(2-chloro-4-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: -2.03

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