4-Chloro-3-(5-((3-(2-ethoxy-2-oxoethyl)-2,4-dioxoimidazolidin-1-yl)methyl)furan-2-yl)benzoic Acid

ID: ALA4559664

PubChem CID: 155557780

Max Phase: Preclinical

Molecular Formula: C19H17ClN2O7

Molecular Weight: 420.81

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CCOC(=O)CN1C(=O)CN(Cc2ccc(-c3cc(C(=O)O)ccc3Cl)o2)C1=O

Standard InChI:  InChI=1S/C19H17ClN2O7/c1-2-28-17(24)10-22-16(23)9-21(19(22)27)8-12-4-6-15(29-12)13-7-11(18(25)26)3-5-14(13)20/h3-7H,2,8-10H2,1H3,(H,25,26)

Standard InChI Key:  UYQJOEAETLZFTP-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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   14.8294  -11.1671    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.0426  -10.3756    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8341  -10.1625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.4125  -10.7449    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2081  -10.5318    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4947   -9.7691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6922   -9.9358    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.3578  -10.6872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5433  -10.5990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3725   -9.8006    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.6252   -9.4663    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9579   -9.9464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9579  -10.7677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1806  -11.0224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6964  -10.3591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8792  -10.3591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4664  -11.0682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8792  -11.7773    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    7.6493  -11.0682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2365  -10.3591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6493   -9.6459    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2365   -8.9368    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6493   -8.2277    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4193   -8.9368    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.4664   -9.6459    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1806   -9.6959    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.0816   -9.3879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1698   -8.5734    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.7664  -11.3963    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
  4  5  1  0
  2  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 17 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 22 24  2  0
 21 25  2  0
 16 25  1  0
 15 26  1  0
 12 26  1  0
 10 27  1  0
  7 27  1  0
 27 28  2  0
  8 29  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA4559664

   ---

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: 420.81

Molecular Weight (Monoisotopic): 420.0724

AlogP: 2.63

#Rotatable Bonds: 7

Polar Surface Area: 117.36

Molecular Species: ACID

HBA: 6

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.97

CX Basic pKa: ┄

CX LogP: 1.59

CX LogD: -1.59

Aromatic Rings: 2

Heavy Atoms: 29

QED Weighted: 0.54

Np Likeness Score: -1.27

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