2-[2-Methoxy-4-(5-phenyl-pent-1-ynyl)-phenyl]-ethylamine

ID: ALA110802

PubChem CID: 10913383

Max Phase: Preclinical

Molecular Formula: C20H23NO

Molecular Weight: 293.41

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cc(C#CCCCc2ccccc2)ccc1CCN

Standard InChI:  InChI=1S/C20H23NO/c1-22-20-16-18(12-13-19(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:  NNSCYTVKHDKQOO-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 22 23  0  0  0  0  0  0  0  0999 V2000
    5.2292   -3.2875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2250   -4.1042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5167   -1.2167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2292   -0.8042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5167   -2.0500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2292   -2.4625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9417   -1.2167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9417   -2.0500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8042   -0.8125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9375    1.2583    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2292   -4.9292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0875   -5.3542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2250    0.0208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9417    0.4333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8000   -4.9375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0875   -1.2250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3750   -4.9417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0917   -6.1750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5167   -5.3417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3792   -6.5917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6625   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6667   -6.1875    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  3  1  0
 10 14  1  0
 11  2  1  0
 12 15  1  0
 13  4  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:

   

   ALA110802

   2-[2-Methoxy-4-(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: 9.72

CX LogP: 4.68

CX LogD: 2.44

Aromatic Rings: 2

Heavy Atoms: 22

QED Weighted: 0.65

Np Likeness Score: 0.03

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