6-Chloro-4'-((3-(2-ethoxy-2-oxoethyl)-2,4-dioxothiazolidin-5-ylidene)methyl)-[1,1'-biphenyl]-3-carboxylic Acid

ID: ALA4524413

PubChem CID: 155520160

Max Phase: Preclinical

Molecular Formula: C21H16ClNO6S

Molecular Weight: 445.88

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CCOC(=O)CN1C(=O)S/C(=C\c2ccc(-c3cc(C(=O)O)ccc3Cl)cc2)C1=O

Standard InChI:  InChI=1S/C21H16ClNO6S/c1-2-29-18(24)11-23-19(25)17(30-21(23)28)9-12-3-5-13(6-4-12)15-10-14(20(26)27)7-8-16(15)22/h3-10H,2,11H2,1H3,(H,26,27)/b17-9-

Standard InChI Key:  NXLHGKYJUGZMBL-MFOYZWKCSA-N

Molfile:  

 
     RDKit          2D

 30 32  0  0  0  0  0  0  0  0999 V2000
    6.6724  -10.7232    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3815  -10.3146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0865  -10.7232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0865  -11.5404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7956  -11.9490    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5047  -11.5404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2096  -11.9490    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    9.5047  -10.7232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2096  -10.3146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9187  -10.7232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6237  -10.3146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6237   -9.4974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3328   -9.0889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0419   -9.4974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1259  -10.3079    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   13.9284  -10.4786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3370   -9.7695    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.1474   -9.6855    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4777   -8.9382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2922   -8.8542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.6266   -8.1069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4370   -8.0229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0017   -8.2791    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.7892   -9.1631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9558   -8.3647    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.2587  -11.2259    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.9187   -9.0889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2096   -9.4974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7956  -10.3146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3815   -9.4974    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  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  6  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 19 23  2  0
 17 24  1  0
 14 24  1  0
 24 25  2  0
 16 26  2  0
 12 27  1  0
 27 28  2  0
  9 28  1  0
  8 29  2  0
  3 29  1  0
  2 30  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA4524413

   ---

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: 445.88

Molecular Weight (Monoisotopic): 445.0387

AlogP: 4.30

#Rotatable Bonds: 6

Polar Surface Area: 100.98

Molecular Species: ACID

HBA: 6

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 4.01

CX Basic pKa: ┄

CX LogP: 3.96

CX LogD: 0.81

Aromatic Rings: 2

Heavy Atoms: 30

QED Weighted: 0.52

Np Likeness Score: -1.30

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