9,10-Dimethoxy-5,8,13,13a-tetrahydro-6H-[1,3]dioxolo[4,5-g]isoquino[3,2-a]isoquinoline 7-oxide

ID: ALA11697

Chembl Id: CHEMBL11697

Cas Number: 86639-35-2

PubChem CID: 328042

Max Phase: Preclinical

Molecular Formula: C20H21NO5

Molecular Weight: 355.39

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc2c(c1OC)C[N+]1([O-])CCc3cc4c(cc3C1C2)OCO4

Standard InChI:  InChI=1S/C20H21NO5/c1-23-17-4-3-12-7-16-14-9-19-18(25-11-26-19)8-13(14)5-6-21(16,22)10-15(12)20(17)24-2/h3-4,8-9,16H,5-7,10-11H2,1-2H3

Standard InChI Key:  FCFHJJYTYOPPEM-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA11697

   trans-Canadine-N-oxide

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: 355.39

Molecular Weight (Monoisotopic): 355.1420

AlogP: 3.10

#Rotatable Bonds: 2

Polar Surface Area: 59.98

Molecular Species: NEUTRAL

HBA: 5

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 2.97

CX LogP: 1.96

CX LogD: 1.96

Aromatic Rings: 2

Heavy Atoms: 26

QED Weighted: 0.61

Np Likeness Score: 1.73

References

1. Vennerstrom JL, Klayman DL..  (1988)  Protoberberine alkaloids as antimalarials.,  31  (6): [PMID:3286870] [10.1021/jm00401a006]

2. Bian X, He L, Yang G..  (2006)  Synthesis and antihyperglycemic evaluation of various protoberberine derivatives.,  16  (5): [PMID:16359864] [10.1016/j.bmcl.2005.11.045]

3. PubChem BioAssay data set, 

Source

Source(2):

• Scientific Literature
• PubChem BioAssays