13-Butyl-2,3,9,10-tetramethoxy-5,6-dihydro-isoquino[3,2-a]isoquinoliny lium chloride

ID: ALA2270081

PubChem CID: 76334096

Max Phase: Preclinical

Molecular Formula: C25H30ClNO4

Molecular Weight: 408.52

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCCc1c2[n+](cc3c(OC)c(OC)ccc13)CCc1cc(OC)c(OC)cc1-2.[Cl-]

Standard InChI:  InChI=1S/C25H30NO4.ClH/c1-6-7-8-18-17-9-10-21(27-2)25(30-5)20(17)15-26-12-11-16-13-22(28-3)23(29-4)14-19(16)24(18)26;/h9-10,13-15H,6-8,11-12H2,1-5H3;1H/q+1;/p-1

Standard InChI Key:  SIMCDTUXLGJADR-UHFFFAOYSA-M

Molfile:  

     RDKit          2D

 31 33  0  0  0  0  0  0  0  0999 V2000
   19.5116  -12.9386    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   16.6845  -13.5147    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6827  -11.8693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3947  -12.2766    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3981  -13.1058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8276  -12.2707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1072  -11.8568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8310  -13.0999    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.1139  -13.5172    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1168  -14.3423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5510  -13.5077    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5521  -14.3390    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8365  -14.7550    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8399  -15.5807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5582  -15.9916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2745  -15.5706    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2675  -14.7462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9729  -13.1037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9741  -12.2787    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9757  -14.3305    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.6898  -14.7358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9889  -15.9754    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.9956  -16.7966    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2633  -11.8676    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.2615  -13.5137    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.5518  -12.2778    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2608  -14.3349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4070  -14.7552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4096  -15.5764    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6998  -15.9893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9873  -15.5810    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
 30 31  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: 408.52

Molecular Weight (Monoisotopic): 408.2169

AlogP: 4.73

#Rotatable Bonds: 7

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: 0.63

CX LogD: 0.63

Aromatic Rings: 3

Heavy Atoms: 30

QED Weighted: 0.53

Np Likeness Score: 1.02

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