5-(3-(4-oxo-2,4,5,6-tetrahydro-1H-pyrrolo[3,2,1-ij]quinolin-7-yl)benzylidene)thiazolidine-2,4-dione

ID: ALA3629573

PubChem CID: 75593388

Max Phase: Preclinical

Molecular Formula: C21H16N2O3S

Molecular Weight: 376.44

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C1NC(=O)/C(=C/c2cccc(-c3ccc4c5c3CCC(=O)N5CC4)c2)S1

Standard InChI:  InChI=1S/C21H16N2O3S/c24-18-7-6-16-15(5-4-13-8-9-23(18)19(13)16)14-3-1-2-12(10-14)11-17-20(25)22-21(26)27-17/h1-5,10-11H,6-9H2,(H,22,25,26)/b17-11-

Standard InChI Key:  CGUAICJZQHKUOC-BOPFTXTBSA-N

Molfile:  

     RDKit          2D

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   -2.5371   -1.2229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2594   -1.9530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2594    0.9674    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.8944    2.4276    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9674    2.4458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.5553   -1.2229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5553    0.2373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2777    0.9674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2777   -3.4538    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5780   -4.2021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5803   -5.7021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2824   -6.4540    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.0201   -4.2060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5750    0.8396    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3180   -6.4557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6178   -5.7054    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7527   -4.2243    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2193   -3.9095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9719   -5.2071    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9704   -6.3238    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2152   -7.4985    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7053   -2.8123    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  1  1  0
  1  2  1  0
  2  3  1  0
  3  8  1  0
  4  7  1  0
  5  6  1  0
  6  4  1  0
  7  8  1  0
  7 12  2  0
  8  9  2  0
  9 10  1  0
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 11 12  1  0
  5 12  1  0
 13 14  2  0
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 18 13  1  0
  9 13  1  0
  1 19  2  0
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 21 22  1  0
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 24 25  1  0
 25 21  1  0
 25 26  2  0
 23 27  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA3629573

   (5Z)-5-[[3-(11-oxo-1-azatricyclo[6.3.1.04,12]dodeca-4(12),5,7-trien-7-yl)phenyl]methylidene]-1,3-thiazolidine-2,4-dione

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 376.44

Molecular Weight (Monoisotopic): 376.0882

AlogP: 3.51

#Rotatable Bonds: 2

Polar Surface Area: 66.48

Molecular Species: ACID

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 6.20

CX Basic pKa: ┄

CX LogP: 2.94

CX LogD: 1.79

Aromatic Rings: 2

Heavy Atoms: 27

QED Weighted: 0.81

Np Likeness Score: -0.87

References

1. Dounay AB, Tuttle JB, Verhoest PR..  (2015)  Challenges and Opportunities in the Discovery of New Therapeutics Targeting the Kynurenine Pathway.,  58  (22): [PMID:26207924] [10.1021/acs.jmedchem.5b00461]

Source

Source(1):

• Scientific Literature