9-Methoxy-2,3,10-trihydroxy-5,6-dihydroisoquinolino[3,2-a]isoquinolinium chloride

ID: ALA4744986

PubChem CID: 162648530

Max Phase: Preclinical

Molecular Formula: C18H16ClNO4

Molecular Weight: 310.33

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  COc1c(O)ccc2cc3[n+](cc12)CCc1cc(O)c(O)cc1-3.[Cl-]

Standard InChI:  InChI=1S/C18H15NO4.ClH/c1-23-18-13-9-19-5-4-11-7-16(21)17(22)8-12(11)14(19)6-10(13)2-3-15(18)20;/h2-3,6-9,20,22H,4-5H2,1H3;1H

Standard InChI Key:  CVUSQCKSEAYSAS-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 24 26  0  0  0  0  0  0  0  0999 V2000
   29.1356  -13.2726    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   26.4313  -11.2985    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.4302  -12.1255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.1446  -12.5381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.1428  -10.8860    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.8578  -11.2949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.8586  -12.1213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.5735  -12.5321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.5679  -10.8810    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.2835  -11.2880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.2852  -12.1146    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   29.9980  -12.5241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.7136  -12.1115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.9945  -10.8709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.7110  -11.2850    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.4258  -10.8716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.9922  -10.0478    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.7041   -9.6320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.4238  -10.0392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.1465  -13.3627    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.7157  -12.5372    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.4333  -13.7767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.6983   -8.8074    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   32.1357   -9.6230    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  2  0
  3  4  1  0
  4  7  2  0
  6  5  2  0
  5  2  1  0
  6  7  1  0
  7  8  1  0
  8 11  2  0
 10  9  2  0
  9  6  1  0
 10 11  1  0
 10 14  1  0
 11 12  1  0
 12 13  1  0
 13 15  1  0
 14 15  2  0
 15 16  1  0
 16 19  2  0
 18 17  2  0
 17 14  1  0
 18 19  1  0
  4 20  1  0
  3 21  1  0
 20 22  1  0
 18 23  1  0
 19 24  1  0
M  CHG  2   1  -1  11   1
M  END

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 310.33

Molecular Weight (Monoisotopic): 310.1074

AlogP: 2.48

#Rotatable Bonds: 1

Polar Surface Area: 73.80

Molecular Species: NEUTRAL

HBA: 4

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.49

CX Basic pKa: ┄

CX LogP: -1.66

CX LogD: -1.69

Aromatic Rings: 3

Heavy Atoms: 23

QED Weighted: 0.48

Np Likeness Score: 1.81

References

1. Tajiri M,Yamada R,Hotsumi M,Makabe K,Konno H.  (2021)  The total synthesis of berberine and selected analogues, and their evaluation as amyloid beta aggregation inhibitors.,  215  [PMID:33611188] [10.1016/j.ejmech.2021.113289]

Source

Source(1):

• Scientific Literature