2-[2-Methoxy-5-(5-phenyl-pent-1-ynyl)-phenyl]-ethylamine

ID: ALA332919

PubChem CID: 10924334

Max Phase: Preclinical

Molecular Formula: C20H23NO

Molecular Weight: 293.41

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc(C#CCCCc2ccccc2)cc1CCN

Standard InChI:  InChI=1S/C20H23NO/c1-22-20-13-12-18(16-19(20)14-15-21)11-7-3-6-10-17-8-4-2-5-9-17/h2,4-5,8-9,12-13,16H,3,6,10,14-15,21H2,1H3

Standard InChI Key:  HUDCDJZZEMXOSM-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 22 23  0  0  0  0  0  0  0  0999 V2000
    2.5625   -3.5250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2750   -3.9375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1292   -1.8667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4167   -2.2792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8417   -2.2792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8417   -3.1125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4167   -3.1125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1292   -3.5250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2958   -1.8750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8375    0.1958    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9875   -4.3500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6917   -6.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1250   -1.0417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8417   -0.6292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7000   -5.5875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0125   -2.2875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9792   -6.8167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4042   -6.8167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9792   -5.1750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4125   -7.6417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9792   -7.6417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6917   -8.0542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  3  0
  3  5  2  0
  4  7  2  0
  5  6  1  0
  6  1  1  0
  7  8  1  0
  8  6  2  0
  9  4  1  0
 10 14  1  0
 11  2  1  0
 12 15  1  0
 13  3  1  0
 14 13  1  0
 15 19  1  0
 16  9  1  0
 17 12  2  0
 18 12  1  0
 19 11  1  0
 20 18  2  0
 21 17  1  0
 22 20  1  0
  3  4  1  0
 21 22  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA332919

   2-[2-Methoxy-5-(5-phenyl-pent-1-ynyl)-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: 293.41

Molecular Weight (Monoisotopic): 293.1780

AlogP: 3.57

#Rotatable Bonds: 6

Polar Surface Area: 35.25

Molecular Species: BASE

HBA: 2

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 2

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 9.70

CX LogP: 4.68

CX LogD: 2.46

Aromatic Rings: 2

Heavy Atoms: 22

QED Weighted: 0.65

Np Likeness Score: 0.00

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