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

ID: ALA4579781

PubChem CID: 155565355

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\c2cccc(-c3cc(C(=O)O)ccc3Cl)c2)C1=O

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

Standard InChI Key:  VKWPFQRLQDRFKP-MFOYZWKCSA-N

Molfile:  

 
     RDKit          2D

 30 32  0  0  0  0  0  0  0  0999 V2000
    9.0354   -7.1463    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.3280   -7.5577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3312   -8.3749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6237   -8.7863    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6270   -9.6035    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3336  -10.0092    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3368  -10.8264    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    9.0410   -9.5978    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7517  -10.0078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7550  -10.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4615  -11.2307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1690  -10.8193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1658  -10.0022    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8732   -9.5908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5798   -9.9965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6712  -10.8107    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   13.4702  -10.9783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8760  -10.2717    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.6902  -10.1804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1689  -10.8417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8416  -11.5903    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.3243  -12.2476    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9929  -12.9962    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9831  -10.7545    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.3299   -9.6633    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4975   -8.8643    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.8035  -11.7243    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.4592   -9.5964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0419   -8.7807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6214   -7.1519    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  1  0
 14 15  2  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
 22 23  1  0
 20 24  2  0
 18 25  1  0
 15 25  1  0
 25 26  2  0
 17 27  2  0
 13 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:

   

   ALA4579781

   ---

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: -1.35

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