(Z)-tert-butyl 3-(2-nitro-4,9-dioxo-4,9-dihydrothieno[2,3-g]quinolin-8-yl)acrylate

ID: ALA4176204

PubChem CID: 141334332

Max Phase: Preclinical

Molecular Formula: C18H14N2O6S

Molecular Weight: 386.39

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(C)(C)OC(=O)/C=C\c1ccnc2c1C(=O)c1sc([N+](=O)[O-])cc1C2=O

Standard InChI:  InChI=1S/C18H14N2O6S/c1-18(2,3)26-12(21)5-4-9-6-7-19-14-13(9)16(23)17-10(15(14)22)8-11(27-17)20(24)25/h4-8H,1-3H3/b5-4-

Standard InChI Key:  ZPQVFBRJOSHZPZ-PLNGDYQASA-N

Molfile:  

     RDKit          2D

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   13.6949   -5.5787    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.0102   -6.3632    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.1980   -5.9268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4649   -7.1419    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0367   -7.1878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8766   -5.5659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7641   -7.5771    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7821   -5.9022    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5113   -4.6906    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.9076   -7.6688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2108   -5.1085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5820   -6.4090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3837   -6.2175    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   14.1163   -4.8772    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3358   -7.6230    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.0917   -6.2931    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.8995   -6.3482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9252   -4.7116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4836   -6.3236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8867   -7.1665    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.9400   -3.8970    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8812   -6.8442    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6139   -5.9514    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4076   -4.8946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6085   -7.2336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6267   -5.1331    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7969   -5.0875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 27  8  1  0
 25 12  1  0
  9 27  2  0
  7  5  1  0
 25 22  1  0
 25 10  1  0
 19  4  1  0
  5  2  2  0
 17 23  1  0
  1 14  1  0
 19  3  1  0
 23 26  2  0
 26 24  1  0
 23 13  1  0
 17 20  2  0
  3 11  2  0
 24  6  2  0
  3 17  1  0
  8 19  2  0
 15 25  1  0
  4  7  2  0
  5 15  1  0
  9 11  1  0
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  6 13  1  0
  6  1  1  0
 26 18  1  0
 18 11  1  0
  1 16  2  0
M  CHG  2   1   1  14  -1
M  END

Alternative Forms

1. Parent:

   

   ALA4176204

   ---

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: 386.39

Molecular Weight (Monoisotopic): 386.0573

AlogP: 3.18

#Rotatable Bonds: 3

Polar Surface Area: 116.47

Molecular Species: NEUTRAL

HBA: 8

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 1.63

CX LogP: 3.70

CX LogD: 3.70

Aromatic Rings: 2

Heavy Atoms: 27

QED Weighted: 0.29

Np Likeness Score: -0.01

References

1. Liu N, Zhong H, Tu J, Jiang Z, Jiang Y, Jiang Y, Jiang Y, Li J, Zhang W, Wang Y, Sheng C..  (2018)  Discovery of simplified sampangine derivatives as novel fungal biofilm inhibitors.,  143  [PMID:29126739] [10.1016/j.ejmech.2017.10.043]

Source

Source(1):

• Scientific Literature