2-{5-[2-(4-Bromo-phenyl)-ethoxy]-2-methoxy-phenyl}-ethylamine

ID: ALA109763

PubChem CID: 44340100

Max Phase: Preclinical

Molecular Formula: C17H20BrNO2

Molecular Weight: 350.26

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc(OCCc2ccc(Br)cc2)cc1CCN

Standard InChI:  InChI=1S/C17H20BrNO2/c1-20-17-7-6-16(12-14(17)8-10-19)21-11-9-13-2-4-15(18)5-3-13/h2-7,12H,8-11,19H2,1H3

Standard InChI Key:  SBJQOCFOTJYSGU-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 21 22  0  0  0  0  0  0  0  0999 V2000
    0.6292   -2.5667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0833   -2.9792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3417   -2.9792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0833   -3.8042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3417   -3.8042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6292   -2.9792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6292   -4.2167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2042   -3.8042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3500   -2.5625    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    4.9125   -2.5667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7958   -2.5667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6292   -3.8042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3375   -0.5042    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2000   -2.9792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9167   -4.2167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625   -4.2167    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7750   -3.8042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6250   -1.7417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4917   -4.2167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3417   -1.3292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5125   -2.9792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  1  2  0
  4  2  2  0
  5  3  1  0
  6 12  2  0
  7  5  2  0
  8 19  1  0
  9  6  1  0
 10 14  2  0
 11  2  1  0
 12 15  1  0
 13 20  1  0
 14  8  1  0
 15  8  2  0
 16  5  1  0
 17 16  1  0
 18  1  1  0
 19 17  1  0
 20 18  1  0
 21 11  1  0
  7  4  1  0
 10  6  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA109763

   2-{5-[2-(4-Bromo-phenyl)-ethoxy]-2-methoxy-phenyl}-ethylamine

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: 350.26

Molecular Weight (Monoisotopic): 349.0677

AlogP: 3.58

#Rotatable Bonds: 7

Polar Surface Area: 44.48

Molecular Species: BASE

HBA: 3

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 3

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 9.68

CX LogP: 3.85

CX LogD: 1.64

Aromatic Rings: 2

Heavy Atoms: 21

QED Weighted: 0.83

Np Likeness Score: -0.29

References

1. Rangisetty JB, Dukat M, Dowd CS, Herrick-Davis K, DuPre A, Gadepalli S, Teitler M, Kelley CR, Sharif NA, Glennon RA..  (2001)  1-[2-methoxy-5-(3-phenylpropyl)]-2-aminopropane unexpectedly shows 5-HT(2A) serotonin receptor affinity and antagonist character.,  44  (20): [PMID:11563927] [10.1021/jm0100739]

Source

Source(1):

• Scientific Literature