(Z)-2-(3-((3-(2-Ethoxy-2-oxoethyl)-2,4-dioxothiazolidin-5-ylidene)methyl)phenyl)acetic Acid

ID: ALA4476456

PubChem CID: 155538143

Max Phase: Preclinical

Molecular Formula: C16H15NO6S

Molecular Weight: 349.36

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CCOC(=O)CN1C(=O)S/C(=C\c2cccc(CC(=O)O)c2)C1=O

Standard InChI:  InChI=1S/C16H15NO6S/c1-2-23-14(20)9-17-15(21)12(24-16(17)22)7-10-4-3-5-11(6-10)8-13(18)19/h3-7H,2,8-9H2,1H3,(H,18,19)/b12-7-

Standard InChI Key:  AATDXKGBQDRSFJ-GHXNOFRVSA-N

Molfile:  

 
     RDKit          2D

 24 25  0  0  0  0  0  0  0  0999 V2000
    9.3660   -5.4952    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.1952   -6.2977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4479   -6.6321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5319   -7.4466    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    7.7347   -6.2194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0256   -6.6321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3165   -6.2194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6074   -6.6321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6074   -7.4493    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3165   -7.8620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0256   -7.4493    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7430   -6.9042    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.5576   -6.8202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0419   -7.4834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7075   -8.2307    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.1917   -8.8981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8573   -9.6454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8564   -7.3994    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.3344   -7.6174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6688   -8.3647    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8990   -6.2248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1920   -6.6346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4819   -6.2288    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1918   -7.4533    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  1  0
  3  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
  6 11  1  0
  2 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 14 18  2  0
 12 19  1  0
  4 19  1  0
 19 20  2  0
  8 21  1  0
 21 22  1  0
 22 23  1  0
 22 24  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA4476456

   ---

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: 349.36

Molecular Weight (Monoisotopic): 349.0620

AlogP: 1.91

#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: 3.71

CX Basic pKa: ┄

CX LogP: 1.69

CX LogD: -1.61

Aromatic Rings: 1

Heavy Atoms: 24

QED Weighted: 0.62

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