ethyl 3-nitro-2-(3-(trifluoromethoxy)phenyl)propanoate

ID: ALA3319287

PubChem CID: 118709478

Max Phase: Preclinical

Molecular Formula: C12H12F3NO5

Molecular Weight: 307.22

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCOC(=O)C(C[N+](=O)[O-])c1cccc(OC(F)(F)F)c1

Standard InChI:  InChI=1S/C12H12F3NO5/c1-2-20-11(17)10(7-16(18)19)8-4-3-5-9(6-8)21-12(13,14)15/h3-6,10H,2,7H2,1H3

Standard InChI Key:  BEOUNFQWFPIINM-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 21 21  0  0  0  0  0  0  0  0999 V2000
   13.2222  -13.8386    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2211  -14.6581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9291  -15.0671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6388  -14.6576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6360  -13.8350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9273  -13.4297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9249  -12.6125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6314  -12.2018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2160  -12.2060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5095  -12.6167    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.6289  -11.3846    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.5076  -13.4383    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.7963  -12.2147    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.3403  -12.6083    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.0468  -12.1976    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7557  -12.6041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3471  -15.0651    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.3484  -15.8823    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0568  -16.2898    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   14.6413  -16.2920    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   15.3409  -16.6988    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  1  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
  8 11  2  0
 10 12  2  0
 10 13  1  0
  8 14  1  0
 14 15  1  0
 15 16  1  0
  4 17  1  0
 17 18  1  0
 18 19  1  0
 18 20  1  0
 18 21  1  0
M  CHG  2  10   1  13  -1
M  END

Alternative Forms

1. Parent:

   

   ALA3319287

   ---

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: 307.22

Molecular Weight (Monoisotopic): 307.0668

AlogP: 2.51

#Rotatable Bonds: 6

Polar Surface Area: 78.67

Molecular Species: NEUTRAL

HBA: 5

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.62

CX Basic pKa: ┄

CX LogP: 3.35

CX LogD: 3.33

Aromatic Rings: 1

Heavy Atoms: 21

QED Weighted: 0.46

Np Likeness Score: -0.99

References

1. Csuk R, Heller L, Siewert B, Gutnov A, Seidelmann O, Wendisch V..  (2014)  β-Nitro substituted carboxylic acids and their cytotoxicity.,  24  (16): [PMID:25001484] [10.1016/j.bmcl.2014.06.021]

Source

Source(1):

• Scientific Literature