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

ID: ALA4521126

PubChem CID: 155542542

Max Phase: Preclinical

Molecular Formula: C16H15NO7S

Molecular Weight: 365.36

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CCOC(=O)CN1C(=O)S/C(=C\c2cc(CC(=O)O)ccc2O)C1=O

Standard InChI:  InChI=1S/C16H15NO7S/c1-2-24-14(21)8-17-15(22)12(25-16(17)23)7-10-5-9(6-13(19)20)3-4-11(10)18/h3-5,7,18H,2,6,8H2,1H3,(H,19,20)/b12-7-

Standard InChI Key:  FLJFEDFMWGKGBV-GHXNOFRVSA-N

Molfile:  

 
     RDKit          2D

 25 26  0  0  0  0  0  0  0  0999 V2000
    9.4320   -4.9710    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2612   -5.7736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5139   -6.1079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5980   -6.9225    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    7.8007   -5.6952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0916   -6.1079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3825   -5.6952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6735   -6.1079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6735   -6.9251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3825   -7.3379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0916   -6.9251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8091   -6.3800    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.6236   -6.2960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1079   -6.9593    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7735   -7.7066    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.2578   -8.3740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9234   -9.1212    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9224   -6.8752    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.4005   -7.0932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7349   -7.8405    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9650   -5.7006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2580   -6.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5479   -5.7046    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2578   -6.9292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8001   -7.3325    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
 11 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4521126

   ---

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: 365.36

Molecular Weight (Monoisotopic): 365.0569

AlogP: 1.62

#Rotatable Bonds: 6

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: 3.50

CX Basic pKa: ┄

CX LogP: 1.39

CX LogD: -1.99

Aromatic Rings: 1

Heavy Atoms: 25

QED Weighted: 0.58

Np Likeness Score: -1.15

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