rac-4,4,4-Trifluoro-3-(S-methyl-3-indolylbutyricacid

ID: ALA2287132

PubChem CID: 76312917

Max Phase: Preclinical

Molecular Formula: C13H12F3NO2

Molecular Weight: 271.24

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1ccc2[nH]cc(C(CC(=O)O)C(F)(F)F)c2c1

Standard InChI:  InChI=1S/C13H12F3NO2/c1-7-2-3-11-8(4-7)9(6-17-11)10(5-12(18)19)13(14,15)16/h2-4,6,10,17H,5H2,1H3,(H,18,19)

Standard InChI Key:  YMINSTSPWAELET-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 19 20  0  0  0  0  0  0  0  0999 V2000
   21.9719   -3.6897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.9708   -4.5092    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.6788   -4.9182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.6771   -3.2808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.3857   -3.6861    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.3859   -4.5093    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.1689   -4.7635    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   24.6526   -4.0973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.1681   -3.4322    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.5702   -2.7209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.3874   -2.7135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.1553   -2.0169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.7896   -2.0021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.6046   -1.9939    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.3725   -1.2973    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.5574   -1.3055    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   23.3381   -2.0243    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   23.7398   -1.3042    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   21.2641   -3.2813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  6  2  0
  5  4  2  0
  4  1  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9  5  1  0
  9 10  1  0
 10 11  1  0
 10 12  1  0
 11 13  1  0
 13 14  1  0
 13 15  2  0
 12 16  1  0
 12 17  1  0
 12 18  1  0
  1 19  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2287132

   4,4,4-trifluoro-3-(5-methyl-1H-indol-3-yl)butanoic acid

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: 271.24

Molecular Weight (Monoisotopic): 271.0820

AlogP: 3.60

#Rotatable Bonds: 3

Polar Surface Area: 53.09

Molecular Species: ACID

HBA: 1

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 3

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 4.59

CX Basic pKa: ┄

CX LogP: 3.23

CX LogD: 0.50

Aromatic Rings: 2

Heavy Atoms: 19

QED Weighted: 0.90

Np Likeness Score: -0.37

References

1. KATAYAMA M, GAUTAM RK.  (1997)  Synthesis and Biological Activities of Fluorinated Plant Growth Regulators, 4, 4, 4-Trifluoro-3-(3-indolyl)butyric Acids and 4, 4, 4-Trifluoro-3-(2-indolyl)butyric Acid Bearing a Methyl Group on the Indole Nucleus,  22  (4): [10.1584/jpestics.22.331]

Source

Source(1):

• Scientific Literature