(R)-N-(3-Bromobenzyl)-N-methyl-1-(naphthalen-1-yl)ethanamine

ID: ALA2426529

PubChem CID: 72708721

Max Phase: Preclinical

Molecular Formula: C20H20BrN

Molecular Weight: 354.29

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C[C@H](c1cccc2ccccc12)N(C)Cc1cccc(Br)c1

Standard InChI:  InChI=1S/C20H20BrN/c1-15(22(2)14-16-7-5-10-18(21)13-16)19-12-6-9-17-8-3-4-11-20(17)19/h3-13,15H,14H2,1-2H3/t15-/m1/s1

Standard InChI Key:  CEFBDZIOKWAKRJ-OAHLLOKOSA-N

Molfile:  

     RDKit          2D

 22 24  0  0  0  0  0  0  0  0999 V2000
   18.1521  -16.0494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1510  -16.8768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8657  -17.2896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8639  -15.6367    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5792  -16.0457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5801  -16.8726    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2953  -17.2835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.0103  -16.8688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.0056  -16.0389    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2897  -15.6316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2853  -14.8066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9976  -14.3904    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.5687  -14.3980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.7142  -14.7991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9932  -13.5654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.4265  -14.3828    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.1415  -14.7964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.8532  -14.3808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.8494  -13.5550    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.1277  -13.1465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.4189  -13.5644    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.5697  -14.7899    0.0000 Br  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  1
 11 13  1  0
 12 14  1  0
 12 15  1  0
 14 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 16  1  0
 18 22  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2426529

   (1R)-N-[(3-bromophenyl)methyl]-N-methyl-1-(1-naphthyl)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: 354.29

Molecular Weight (Monoisotopic): 353.0779

AlogP: 5.80

#Rotatable Bonds: 4

Polar Surface Area: 3.24

Molecular Species: BASE

HBA: 1

HBD: ┄

#RO5 Violations: 1

HBA (Lipinski): 1

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: 9.11

CX LogP: 5.81

CX LogD: 4.10

Aromatic Rings: 3

Heavy Atoms: 22

QED Weighted: 0.57

Np Likeness Score: -1.20

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