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

ID: ALA4794142

PubChem CID: 3125029

Max Phase: Preclinical

Molecular Formula: C22H22ClN3O6S

Molecular Weight: 491.95

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CCCC1Nc2c(C(=O)O)ccc([N+](=O)[O-])c2C2C(Cl)C(Sc3ccccc3[N+](=O)[O-])CC12

Standard InChI:  InChI=1S/C22H22ClN3O6S/c1-2-5-13-12-10-17(33-16-7-4-3-6-14(16)25(29)30)20(23)18(12)19-15(26(31)32)9-8-11(22(27)28)21(19)24-13/h3-4,6-9,12-13,17-18,20,24H,2,5,10H2,1H3,(H,27,28)

Standard InChI Key:  COGRKLXBUHSTNJ-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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   13.6376  -18.5550    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9256  -19.7968    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   11.7739  -20.7831    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   14.3497  -19.7968    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   16.4842  -20.2064    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   10.8287  -19.3959    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
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   10.8213  -17.9700    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4056  -17.2583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5796  -17.2625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1712  -17.9842    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5894  -18.6930    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1822  -19.4138    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.6022  -20.1240    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.3573  -19.4224    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.6397  -17.7317    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3553  -17.3211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3574  -16.4961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9151  -21.4303    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.9116  -22.2554    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.2024  -21.0148    0.0000 O   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
  2 28  1  0
 28 29  1  0
 29 30  1  0
 31 32  2  0
 31 33  1  0
 11 31  1  0
M  CHG  4  25   1  27  -1  31   1  33  -1
M  END

Alternative Forms

1. Parent:

   

   ALA4794142

   1-chloro-9-nitro-2-(2-nitrophenyl)sulfanyl-4-propyl-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: 491.95

Molecular Weight (Monoisotopic): 491.0918

AlogP: 5.67

#Rotatable Bonds: 7

Polar Surface Area: 135.61

Molecular Species: ACID

HBA: 7

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 9

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 3.84

CX Basic pKa: 0.51

CX LogP: 5.94

CX LogD: 2.68

Aromatic Rings: 2

Heavy Atoms: 33

QED Weighted: 0.29

Np Likeness Score: -0.13

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