2,3-Methylenedioxy-9,10-dimethoxy-13-n-hexylprotoberberine Chloride

ID: ALA460900

PubChem CID: 25193930

Max Phase: Preclinical

Molecular Formula: C26H30ClNO4

Molecular Weight: 420.53

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCCCCc1c2[n+](cc3c(OC)c(OC)ccc13)CCc1cc3c(cc1-2)OCO3.[Cl-]

Standard InChI:  InChI=1S/C26H30NO4.ClH/c1-4-5-6-7-8-19-18-9-10-22(28-2)26(29-3)21(18)15-27-12-11-17-13-23-24(31-16-30-23)14-20(17)25(19)27;/h9-10,13-15H,4-8,11-12,16H2,1-3H3;1H/q+1;/p-1

Standard InChI Key:  LLJCPAIRNFYCCE-UHFFFAOYSA-M

Molfile:  

     RDKit          2D

 32 35  0  0  0  0  0  0  0  0999 V2000
    7.1417   -3.3375    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    5.7208   -4.5250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.0000   -4.9375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4292   -5.7667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2875   -4.5250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9958   -5.7625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7083   -6.1792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4333   -4.9417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2875   -3.6958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1417   -6.1792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5750   -4.9333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8667   -4.5208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8667   -3.6958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7208   -3.6958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5750   -3.2875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7083   -7.0042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0792   -4.7750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0833   -3.4417    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1458   -7.0042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5958   -4.1083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0042   -3.2792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4250   -7.4208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8542   -5.7708    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2792   -6.1708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8542   -7.4167    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5667   -6.1792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5667   -7.0042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5708   -5.7542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4375   -6.1583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1500   -5.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8583   -6.1625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7250   -5.7458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  2  0
  4  8  2  0
  5  3  1  0
  6  3  1  0
  7  6  2  0
  8  2  1  0
  9  5  1  0
 10  4  1  0
 11  5  2  0
 12 11  1  0
 13 12  2  0
 14  2  1  0
 15  9  2  0
 16  7  1  0
 17 12  1  0
 18 13  1  0
 19 10  2  0
 20 17  1  0
 21 14  1  0
 22 16  2  0
 23 10  1  0
 24  6  1  0
 25 19  1  0
 26 23  1  0
 27 25  1  0
 28 24  1  0
 29 30  1  0
 30 31  1  0
 31 28  1  0
 32 29  1  0
 21  9  1  0
  7  4  1  0
 13 15  1  0
 19 22  1  0
 20 18  1  0
M  CHG  2   1  -1   2   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: 420.53

Molecular Weight (Monoisotopic): 420.2169

AlogP: 5.22

#Rotatable Bonds: 7

Polar Surface Area: 40.80

Molecular Species: NEUTRAL

HBA: 4

HBD: ┄

#RO5 Violations: 1

HBA (Lipinski): 5

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 1.45

CX LogD: 1.45

Aromatic Rings: 3

Heavy Atoms: 31

QED Weighted: 0.39

Np Likeness Score: 1.20

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. Iwasa K, Moriyasu M, Yamori T, Turuo T, Lee DU, Wiegrebe W..  (2001)  In vitro cytotoxicity of the protoberberine-type alkaloids.,  64  (7): [PMID:11473418] [10.1021/np000554f]

3. 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]

4. 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