(R)-1-(4-tert-Butylphenyl)-2-fluoro-N-(naphthalen-1-ylmethyl)ethanamine

ID: ALA2426539

PubChem CID: 72708767

Max Phase: Preclinical

Molecular Formula: C23H26FN

Molecular Weight: 335.47

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(C)(C)c1ccc([C@H](CF)NCc2cccc3ccccc23)cc1

Standard InChI:  InChI=1S/C23H26FN/c1-23(2,3)20-13-11-18(12-14-20)22(15-24)25-16-19-9-6-8-17-7-4-5-10-21(17)19/h4-14,22,25H,15-16H2,1-3H3/t22-/m0/s1

Standard InChI Key:  GMOSMMARRWVBGN-QFIPXVFZSA-N

Molfile:  

     RDKit          2D

 25 27  0  0  0  0  0  0  0  0999 V2000
   19.0334   -4.2675    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0322   -5.0871    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7403   -5.4960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7385   -3.8587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4471   -4.2639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4478   -5.0829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.1564   -5.4900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.8646   -5.0792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.8599   -4.2570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.1508   -3.8537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.1465   -3.0365    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.8520   -2.6242    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.5619   -3.0290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.2674   -2.6167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.9757   -3.0263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.6808   -2.6147    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.6769   -1.7966    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.9621   -1.3920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.2599   -1.8060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.5662   -3.8462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.3819   -1.3833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.0923   -1.7872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.3765   -0.5662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.0841   -0.9699    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.2761   -4.2510    0.0000 F   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  2  0
  8  9  1  0
  9 10  2  0
 10  5  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 14  1  0
 13 20  1  6
 17 21  1  0
 21 22  1  0
 21 23  1  0
 21 24  1  0
 20 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2426539

   (1R)-1-(4-tert-butylphenyl)-2-fluoro-N-(1-naphthylmethyl)ethanamine

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: 335.47

Molecular Weight (Monoisotopic): 335.2049

AlogP: 5.94

#Rotatable Bonds: 5

Polar Surface Area: 12.03

Molecular Species: NEUTRAL

HBA: 1

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 1

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: 7.41

CX LogP: 6.05

CX LogD: 5.74

Aromatic Rings: 3

Heavy Atoms: 25

QED Weighted: 0.61

Np Likeness Score: -0.89

References

1. Thvedt TH, Kaasa K, Sundby E, Charnock C, Hoff BH..  (2013)  Chiral N-benzyl-N-methyl-1-(naphthalen-1-yl)ethanamines and their in vitro antifungal activity against Cryptococcus neoformans, Trichophyton mentagrophytes and Trichophyton rubrum.,  68  [PMID:24051242] [10.1016/j.ejmech.2013.07.043]

Source

Source(1):

• Scientific Literature