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

ID: ALA4468621

PubChem CID: 155533200

Max Phase: Preclinical

Molecular Formula: C15H13NO7S

Molecular Weight: 351.34

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CCOC(=O)CN1C(=O)S/C(=C\c2ccc(O)c(C(=O)O)c2)C1=O

Standard InChI:  InChI=1S/C15H13NO7S/c1-2-23-12(18)7-16-13(19)11(24-15(16)22)6-8-3-4-10(17)9(5-8)14(20)21/h3-6,17H,2,7H2,1H3,(H,20,21)/b11-6-

Standard InChI Key:  KBTHPPDLTCXOOW-WDZFZDKYSA-N

Molfile:  

 
     RDKit          2D

 24 25  0  0  0  0  0  0  0  0999 V2000
    9.2463   -4.6574    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.0755   -5.4599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3282   -5.7943    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4122   -6.6088    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    7.6150   -5.3816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9059   -5.7943    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1968   -5.3816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4877   -5.7943    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4877   -6.6115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1968   -7.0242    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9059   -6.6115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6234   -6.0664    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.4379   -5.9823    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9222   -6.6456    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5878   -7.3929    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.0720   -8.0603    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7376   -8.8076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7367   -6.5616    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2148   -6.7796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5492   -7.5269    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7768   -5.3876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7753   -4.5704    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0698   -5.7974    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7793   -7.0188    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
 21 22  1  0
 21 23  2  0
  8 21  1  0
  9 24  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4468621

   ---

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: 351.34

Molecular Weight (Monoisotopic): 351.0413

AlogP: 1.69

#Rotatable Bonds: 5

Polar Surface Area: 121.21

Molecular Species: ACID

HBA: 7

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 2.71

CX Basic pKa: ┄

CX LogP: 2.06

CX LogD: -1.44

Aromatic Rings: 1

Heavy Atoms: 24

QED Weighted: 0.61

Np Likeness Score: -1.14

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