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

ID: ALA3319286

PubChem CID: 118709477

Max Phase: Preclinical

Molecular Formula: C12H12F3NO4

Molecular Weight: 291.22

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C12H12F3NO4/c1-2-20-11(17)10(7-16(18)19)8-4-3-5-9(6-8)12(13,14)15/h3-6,10H,2,7H2,1H3

Standard InChI Key:  FHZVBOWDYLTHAA-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 20 20  0  0  0  0  0  0  0  0999 V2000
    7.3038  -14.4205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3026  -15.2400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0107  -15.6490    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7203  -15.2396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7175  -14.4169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0089  -14.0116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0064  -13.1944    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7129  -12.7837    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2975  -12.7880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5910  -13.1987    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.7105  -11.9666    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5892  -14.0203    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8778  -12.7966    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.4219  -13.1902    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.1283  -12.7795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8373  -13.1860    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4287  -15.6470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4300  -16.4642    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   10.1358  -15.2373    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   10.1323  -16.0549    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
 17 19  1  0
 17 20  1  0
M  CHG  2  10   1  13  -1
M  END

Alternative Forms

1. Parent:

   

   ALA3319286

   ---

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: 291.22

Molecular Weight (Monoisotopic): 291.0718

AlogP: 2.63

#Rotatable Bonds: 5

Polar Surface Area: 69.44

Molecular Species: NEUTRAL

HBA: 4

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.64

CX Basic pKa: ┄

CX LogP: 2.80

CX LogD: 2.78

Aromatic Rings: 1

Heavy Atoms: 20

QED Weighted: 0.47

Np Likeness Score: -1.11

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