1-chloro-4-(2,4-dichlorophenyl)-2-(2-nitrophenylthio)-2,3,3a,4,5,9b-hexahydro-1H-cyclopenta[c]quinoline-6-carboxylic acid

ID: ALA4783271

PubChem CID: 3124359

Max Phase: Preclinical

Molecular Formula: C25H19Cl3N2O4S

Molecular Weight: 549.86

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=C(O)c1cccc2c1NC(c1ccc(Cl)cc1Cl)C1CC(Sc3ccccc3[N+](=O)[O-])C(Cl)C21

Standard InChI:  InChI=1S/C25H19Cl3N2O4S/c26-12-8-9-13(17(27)10-12)23-16-11-20(35-19-7-2-1-6-18(19)30(33)34)22(28)21(16)14-4-3-5-15(25(31)32)24(14)29-23/h1-10,16,20-23,29H,11H2,(H,31,32)

Standard InChI Key:  TWJIPCHJNJKAHS-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 35 39  0  0  0  0  0  0  0  0999 V2000
    5.4644  -18.9936    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.7521  -18.5767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0397  -19.8190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0351  -18.9936    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2487  -18.7428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7672  -19.4133    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2561  -20.0784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0054  -20.8647    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    5.4644  -19.8190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7526  -20.2248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7492  -21.0424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4568  -21.4550    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1694  -21.0442    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1694  -20.2281    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8857  -19.8153    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6000  -20.2289    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8865  -18.9900    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9417  -19.4179    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.5250  -18.7053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9343  -17.9914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5184  -17.2794    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6920  -17.2835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2834  -18.0056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7018  -18.7147    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2944  -19.4358    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7146  -20.1464    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5364  -19.4444    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7542  -17.7530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4712  -17.3419    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4727  -16.5173    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7579  -16.1027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0401  -16.5189    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0421  -17.3422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1851  -17.7563    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    4.7579  -15.2773    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  4  2  1  0
  3 10  1  0
  9  1  1  0
  1  2  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  3  1  0
  7  8  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14  9  1  0
 15 16  1  0
 15 17  2  0
 14 15  1  0
  6 18  1  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 19  1  0
 25 26  2  0
 25 27  1  0
 24 25  1  0
 28 29  2  0
 29 30  1  0
 30 31  2  0
 31 32  1  0
 32 33  2  0
 33 28  1  0
  2 28  1  0
 29 34  1  0
 31 35  1  0
M  CHG  2  25   1  27  -1
M  END

Alternative Forms

1. Parent:

   

   ALA4783271

   1-chloro-4-(2,4-dichlorophenyl)-2-(2-nitrophenyl)sulfanyl-2,3,3a,4,5,9b-hexahydro-1H-cyclopenta[c]quinoline-6-carboxylic acid

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: 549.86

Molecular Weight (Monoisotopic): 548.0131

AlogP: 7.64

#Rotatable Bonds: 5

Polar Surface Area: 92.47

Molecular Species: ACID

HBA: 5

HBD: 2

#RO5 Violations: 2

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 4.59

CX Basic pKa: 0.69

CX LogP: 7.61

CX LogD: 4.87

Aromatic Rings: 3

Heavy Atoms: 35

QED Weighted: 0.19

Np Likeness Score: -0.70

References

1. Hou X,Sun JP,Ge L,Liang X,Li K,Zhang Y,Fang H.  (2020)  Inhibition of striatal-enriched protein tyrosine phosphatase by targeting computationally revealed cryptic pockets.,  190  [PMID:32078861] [10.1016/j.ejmech.2020.112131]

Source

Source(1):

• Scientific Literature