(Z)-tert-Butyl-4-(3-amino-4,4,4-trifluorobut-2-enoyl)phenyl carbamate

ID: ALA2251698

PubChem CID: 44248046

Max Phase: Preclinical

Molecular Formula: C15H17F3N2O3

Molecular Weight: 330.31

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(C)(C)OC(=O)Nc1ccc(C(=O)/C=C(\N)C(F)(F)F)cc1

Standard InChI:  InChI=1S/C15H17F3N2O3/c1-14(2,3)23-13(22)20-10-6-4-9(5-7-10)11(21)8-12(19)15(16,17)18/h4-8H,19H2,1-3H3,(H,20,22)/b12-8-

Standard InChI Key:  JSBFMADZQJILJU-WQLSENKSSA-N

Molfile:  

     RDKit          2D

 23 23  0  0  0  0  0  0  0  0999 V2000
   40.1310   -0.5299    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   37.9952   -2.6059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.4212   -1.7700    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.5652   -1.7790    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.7052   -1.3603    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.8500   -1.7647    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.2770   -1.3664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.1341   -1.3548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.9923   -1.7754    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.5640   -2.6064    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.2788   -3.0192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.7021   -0.5353    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   41.5562   -1.3535    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   40.8530   -2.5819    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   41.5529   -2.1709    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   35.8560   -3.0145    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   35.1486   -2.6053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.4406   -3.0134    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   35.1492   -1.7881    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   33.7332   -2.6042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.0252   -3.0123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.7338   -1.7870    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.0220   -2.1916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  5  3  1  0
 11  2  2  0
  7  4  1  0
  9  5  1  0
 10 11  1  0
  8  6  1  0
  9  7  2  0
  8  1  1  0
  2  9  1  0
  3  8  2  0
  4 10  2  0
  5 12  2  0
  6 13  1  0
  6 14  1  0
  6 15  1  0
 10 16  1  0
 16 17  1  0
 17 18  1  0
 17 19  2  0
 18 20  1  0
 20 21  1  0
 20 22  1  0
 20 23  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2251698

   tert-butyl N-[4-[(Z)-3-amino-4,4,4-trifluorobut-2-enoyl]phenyl]carbamate

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: 330.31

Molecular Weight (Monoisotopic): 330.1191

AlogP: 3.62

#Rotatable Bonds: 3

Polar Surface Area: 81.42

Molecular Species: NEUTRAL

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.75

CX Basic pKa: ┄

CX LogP: 2.64

CX LogD: 2.64

Aromatic Rings: 1

Heavy Atoms: 23

QED Weighted: 0.65

Np Likeness Score: -0.78

References

1. Gellerman G, Pariente N, Paz Z, Shnaiderman A, Yarden O..  (2009)  Synthesis and antifungal activity of beta-trifluoroalkyl aminovinyl ketone derivatives.,  57  (18): [PMID:19711891] [10.1021/jf902190w]

Source

Source(1):

• Scientific Literature