6-carboxy-9,12-dimethoxy-2,3-methylenedioxy-tetrahydroprotoberberine

ID: ALA4483345

PubChem CID: 155540334

Max Phase: Preclinical

Molecular Formula: C21H21NO6

Molecular Weight: 383.40

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  COc1ccc(OC)c2c1CC1c3cc4c(cc3CC(C(=O)O)N1C2)OCO4

Standard InChI:  InChI=1S/C21H21NO6/c1-25-17-3-4-18(26-2)14-9-22-15(7-13(14)17)12-8-20-19(27-10-28-20)6-11(12)5-16(22)21(23)24/h3-4,6,8,15-16H,5,7,9-10H2,1-2H3,(H,23,24)

Standard InChI Key:  UALULNJJLWOBMB-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 28 32  0  0  0  0  0  0  0  0999 V2000
   12.8932  -13.3543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8914  -11.7169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1851  -12.9453    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1864  -12.1242    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4059  -11.8693    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.9222  -12.5329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4039  -13.1978    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.6000  -12.1222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5988  -12.9473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0260  -12.1242    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3113  -11.7083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0248  -12.9494    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.3057  -13.3555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2979  -14.1767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7361  -13.3645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7265  -14.1920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0074  -14.5942    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9972  -15.4162    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7053  -15.8369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4252  -15.4297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4319  -14.6090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7347  -11.7173    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4414  -12.1277    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.7367  -10.9002    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.1433  -14.2070    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.8472  -14.6221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2845  -15.8159    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.5819  -15.3985    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  1  0
  1  9  2  0
  8  2  2  0
  2  4  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  3  1  0
  8  9  1  0
  8 11  1  0
  9 13  1  0
 12 10  1  0
 10 11  1  0
 12 13  1  0
 12 15  1  0
 13 14  1  0
 14 17  1  0
 16 15  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 16  1  0
 10 22  1  0
 22 23  1  0
 22 24  2  0
 21 25  1  0
 25 26  1  0
 18 27  1  0
 27 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4483345

   ---

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: 383.40

Molecular Weight (Monoisotopic): 383.1369

AlogP: 2.54

#Rotatable Bonds: 3

Polar Surface Area: 77.46

Molecular Species: ACID

HBA: 6

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 0.91

CX Basic pKa: 5.82

CX LogP: 0.59

CX LogD: -0.56

Aromatic Rings: 2

Heavy Atoms: 28

QED Weighted: 0.87

Np Likeness Score: 0.70

References

1. Wang JT, Peng JG, Zhang JQ, Wang ZX, Zhang Y, Zhou XR, Miao J, Tang L..  (2019)  Novel berberine-based derivatives with potent hypoglycemic activity.,  29  (23): [PMID:31629632] [10.1016/j.bmcl.2019.126709]

Source

Source(1):

• Scientific Literature