12-[4-(Furan-2-carbonyl)-piperazin-1-ylmethyl]-9-hydroxy-10-methoxy-5,6-dihydro-[1,3]dioxolo[4,5-g]isoquino[3,2-a]isoquinolin-7-ylium chloride

ID: ALA5194367

PubChem CID: 168287967

Max Phase: Preclinical

Molecular Formula: C29H28ClN3O6

Molecular Weight: 514.56

Names and Identifiers

Canonical SMILES:  COc1cc(CN2CCN(C(=O)c3ccco3)CC2)c2cc3[n+](cc2c1O)CCc1cc2c(cc1-3)OCO2.[Cl-]

Standard InChI:  InChI=1S/C29H27N3O6.ClH/c1-35-27-12-19(15-30-6-8-31(9-7-30)29(34)24-3-2-10-36-24)20-13-23-21-14-26-25(37-17-38-26)11-18(21)4-5-32(23)16-22(20)28(27)33;/h2-3,10-14,16H,4-9,15,17H2,1H3;1H

Standard InChI Key:  RTQGUUMMBRYBJO-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 39 44  0  0  0  0  0  0  0  0999 V2000
    1.3355    3.7197    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -3.2815    3.8830    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6611    3.1505    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0818    2.5633    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3442    2.9327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4676    3.7484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8255    4.2608    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0631    3.9614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4227    4.4722    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3424    4.1725    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4666    3.3644    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2305    3.0701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3587    2.2587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1194    1.9672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2486    1.1604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6186    0.6464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8542    0.9334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7245    1.7436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.5779    2.6376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2095    0.4187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3331   -0.3966    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1010   -0.6974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2244   -1.5129    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5801   -2.0275    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1877   -1.7268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3112   -0.9113    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7035   -2.8432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0166    0.8596    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6611    1.3742    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7639    2.4821    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0587   -3.3578    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4715   -3.1440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6430   -3.9509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4633   -4.0372    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7989   -3.2836    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1859   -2.7317    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  1  0
  4  3  1  0
  5  4  1  0
  6  5  1  0
  6  2  1  0
  7  6  2  0
  8  7  1  0
  8  9  1  0
 10  9  1  0
 11 10  1  0
 11 12  1  0
 13 12  2  0
 13 14  1  0
 15 14  2  0
 16 15  1  0
 17 16  2  0
 18 17  1  0
 18 13  1  0
 19 18  2  0
 20 19  1  0
 20 11  2  0
 21 20  1  0
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 22 21  1  0
  5 22  2  0
 17 23  1  0
 23 24  1  0
 25 24  1  0
 26 25  1  0
 27 26  1  0
 28 27  1  0
 29 28  1  0
 24 29  1  0
 30 27  1  0
 15 31  1  0
 31 32  1  0
 14 33  1  0
 30 35  1  0
 30 34  2  0
 36 37  1  0
 37 38  2  0
 35 36  2  0
 38 39  1  0
 35 39  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:

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 514.56

Molecular Weight (Monoisotopic): 514.1973

AlogP: 3.34

#Rotatable Bonds: 4

Polar Surface Area: 88.49

Molecular Species: NEUTRAL

HBA: 7

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 9

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 8.23

CX Basic pKa: 6.17

CX LogP: -1.50

CX LogD: -1.58

Aromatic Rings: 4

Heavy Atoms: 38

QED Weighted: 0.42

Np Likeness Score: 0.10

References

1. Gaba S, Saini A, Singh G, Monga V..  (2021)  An insight into the medicinal attributes of berberine derivatives: A review.,  38  [PMID:33848698] [10.1016/j.bmc.2021.116143]

Source

Source(1):

• Scientific Literature