2,3-Methylenedioxy-9,10-dimethoxy-13-ethylprotoberberine Chloride

ID: ALA462142

PubChem CID: 11246563

Max Phase: Preclinical

Molecular Formula: C22H22ClNO4

Molecular Weight: 364.42

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCc1c2[n+](cc3c(OC)c(OC)ccc13)CCc1cc3c(cc1-2)OCO3.[Cl-]

Standard InChI:  InChI=1S/C22H22NO4.ClH/c1-4-14-15-5-6-18(24-2)22(25-3)17(15)11-23-8-7-13-9-19-20(27-12-26-19)10-16(13)21(14)23;/h5-6,9-11H,4,7-8,12H2,1-3H3;1H/q+1;/p-1

Standard InChI Key:  HLJAOZVEVJETCY-UHFFFAOYSA-M

Molfile:  

     RDKit          2D

 28 31  0  0  0  0  0  0  0  0999 V2000
    8.9333  -18.0167    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    5.7204  -18.7042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7204  -17.0542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4324  -17.4708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4334  -18.2958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8580  -17.4690    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1424  -17.0551    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8590  -18.2940    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.1422  -18.7082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1425  -19.5315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5761  -18.7031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5747  -19.5327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8569  -19.9428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8531  -20.7649    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5655  -21.1832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2833  -20.7732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2888  -19.9448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0046  -19.5346    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.7177  -19.9494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9955  -21.1897    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.9908  -22.0147    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0038  -18.2913    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0084  -17.4663    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2251  -17.2069    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7365  -17.8717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2178  -18.5418    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4283  -19.9446    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7135  -19.5326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 23  3  1  0
 22  2  1  0
  4  7  1  0
  5  9  1  0
  8  6  1  0
 12 17  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
  6  7  1  0
 17 18  1  0
  8  9  1  0
 18 19  1  0
  2  5  2  0
 16 20  1  0
  4  3  2  0
 20 21  1  0
 22 23  2  0
  4  5  1  0
  8 11  2  0
  9 10  2  0
 10 13  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 22  1  0
 12 11  1  0
 10 27  1  0
 12 13  2  0
 27 28  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: 364.42

Molecular Weight (Monoisotopic): 364.1543

AlogP: 3.66

#Rotatable Bonds: 3

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: -0.33

CX LogD: -0.33

Aromatic Rings: 3

Heavy Atoms: 27

QED Weighted: 0.67

Np Likeness Score: 1.08

References

1. Li YH, Yang P, Kong WJ, Wang YX, Hu CQ, Zuo ZY, Wang YM, Gao H, Gao LM, Feng YC, Du NN, Liu Y, Song DQ, Jiang JD..  (2009)  Berberine analogues as a novel class of the low-density-lipoprotein receptor up-regulators: synthesis, structure-activity relationships, and cholesterol-lowering efficacy.,  52  (2): [PMID:19090767] [10.1021/jm801157z]

2. Liu YX, Xiao CL, Wang YX, Li YH, Yang YH, Li YB, Bi CW, Gao LM, Jiang JD, Song DQ..  (2012)  Synthesis, structure-activity relationship and in vitro anti-mycobacterial evaluation of 13-n-octylberberine derivatives.,  52  [PMID:22503208] [10.1016/j.ejmech.2012.03.012]

3. 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