2,3,9,10-Tetramethoxy-13-propyl-5,6-dihydro-isoquino[3,2-a]isoquinolin ylium chloride

ID: ALA2270080

PubChem CID: 76330508

Max Phase: Preclinical

Molecular Formula: C24H28ClNO4

Molecular Weight: 394.49

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCc1c2[n+](cc3c(OC)c(OC)ccc13)CCc1cc(OC)c(OC)cc1-2.[Cl-]

Standard InChI:  InChI=1S/C24H28NO4.ClH/c1-6-7-17-16-8-9-20(26-2)24(29-5)19(16)14-25-11-10-15-12-21(27-3)22(28-4)13-18(15)23(17)25;/h8-9,12-14H,6-7,10-11H2,1-5H3;1H/q+1;/p-1

Standard InChI Key:  CNWZEQJICFKSBG-UHFFFAOYSA-M

Molfile:  

     RDKit          2D

 30 32  0  0  0  0  0  0  0  0999 V2000
   10.5996  -12.9386    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    7.7635  -13.5645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7617  -11.9192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4738  -12.3264    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4772  -13.1556    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9067  -12.3205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1862  -11.9065    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9101  -13.1497    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.1931  -13.5670    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1959  -14.3921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6300  -13.5574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6312  -14.3888    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9157  -14.8048    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9191  -15.6306    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6373  -16.0414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3535  -15.6204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3466  -14.7960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0521  -13.1535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0533  -12.3285    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0547  -14.3802    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.7689  -14.7856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0680  -16.0252    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.0746  -16.8464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3423  -11.9175    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3405  -13.5635    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6310  -12.3276    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3398  -14.3846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4860  -14.8050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4887  -15.6261    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7789  -16.0390    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 18  2  1  0
  2  5  2  0
  4  3  2  0
  3 19  1  0
  4  5  1  0
  4  7  1  0
  5  9  1  0
  8  6  1  0
  6  7  1  0
  8  9  1  0
  8 11  2  0
  9 10  2  0
 10 13  1  0
 12 11  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 12  1  0
 18 19  2  0
 17 20  1  0
 20 21  1  0
 16 22  1  0
 22 23  1  0
 19 24  1  0
 18 25  1  0
 24 26  1  0
 25 27  1  0
 10 28  1  0
 28 29  1  0
 29 30  1  0
M  CHG  2   1  -1   8   1
M  END

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: 394.49

Molecular Weight (Monoisotopic): 394.2013

AlogP: 4.34

#Rotatable Bonds: 6

Polar Surface Area: 40.80

Molecular Species: NEUTRAL

HBA: 4

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 0.18

CX LogD: 0.18

Aromatic Rings: 3

Heavy Atoms: 29

QED Weighted: 0.58

Np Likeness Score: 1.03

References

1. Iwasa K, Moriyasu M, Nader B..  (2000)  Fungicidal and herbicidal activities of berberine related alkaloids.,  64  (9): [PMID:11055412] [10.1271/bbb.64.1998]

Source

Source(1):

• Scientific Literature