5-(3,4,5-Trimethoxy-phenyl)-2,3-dihydro-imidazo[2,1-a]isoquinoline

ID: ALA81384

PubChem CID: 10246399

Max Phase: Preclinical

Molecular Formula: C20H20N2O3

Molecular Weight: 336.39

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cc(C2=Cc3ccccc3C3=NCCN23)cc(OC)c1OC

Standard InChI:  InChI=1S/C20H20N2O3/c1-23-17-11-14(12-18(24-2)19(17)25-3)16-10-13-6-4-5-7-15(13)20-21-8-9-22(16)20/h4-7,10-12H,8-9H2,1-3H3

Standard InChI Key:  ZNENOHIDSLSQCG-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 25 28  0  0  0  0  0  0  0  0999 V2000
    5.1042   -2.6792    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.5875   -2.9792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1375   -2.0917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6250   -1.7667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7375   -2.0917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0750   -2.6667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5875   -3.5792    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.0917   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9292   -2.0917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6292   -2.6125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6250   -1.5750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0292   -2.6125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0292   -1.5792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6250   -2.9792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6250   -3.5792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5292   -2.0917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7792   -0.9917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9292   -3.1292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5417   -2.9417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5792   -1.7417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9500   -1.6667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2917   -0.6875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5292   -3.1292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0292   -2.6292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0417   -2.0292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  1  1  0
  4  3  2  0
  5  3  1  0
  6  2  1  0
  7  2  2  0
  8  4  1  0
  9 11  1  0
 10 12  1  0
 11 13  2  0
 12  5  2  0
 13  5  1  0
 14  1  1  0
 15 14  1  0
 16  9  1  0
 17 11  1  0
 18 10  1  0
 19  6  1  0
 20  8  1  0
 21 16  1  0
 22 17  1  0
 23 18  1  0
 24 19  2  0
 25 20  2  0
 15  7  1  0
  8  6  2  0
  9 10  2  0
 24 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA81384

   5-(3,4,5-Trimethoxy-phenyl)-2,3-dihydro-imidazo[2,1-a]isoquinoline

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: 336.39

Molecular Weight (Monoisotopic): 336.1474

AlogP: 3.29

#Rotatable Bonds: 4

Polar Surface Area: 43.29

Molecular Species: NEUTRAL

HBA: 5

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 7.09

CX LogP: 2.59

CX LogD: 2.41

Aromatic Rings: 2

Heavy Atoms: 25

QED Weighted: 0.86

Np Likeness Score: 0.05

References

1. Houlihan WJ, Munder PG, Handley DA, Cheon SH, Parrino VA..  (1995)  Antitumor activity of 5-aryl-2,3-dihydroimidazo[2,1-a]isoquinolines.,  38  (2): [PMID:7830265] [10.1021/jm00002a004]

Source

Source(1):

• Scientific Literature