9-O-(4-isopropylbenzyl)berberine bromide

ID: ALA4758271

PubChem CID: 162656939

Max Phase: Preclinical

Molecular Formula: C29H28BrNO4

Molecular Weight: 454.55

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  COc1ccc2cc3[n+](cc2c1OCc1ccc(C(C)C)cc1)CCc1cc2c(cc1-3)OCO2.[Br-]

Standard InChI:  InChI=1S/C29H28NO4.BrH/c1-18(2)20-6-4-19(5-7-20)16-32-29-24-15-30-11-10-22-13-27-28(34-17-33-27)14-23(22)25(30)12-21(24)8-9-26(29)31-3;/h4-9,12-15,18H,10-11,16-17H2,1-3H3;1H/q+1;/p-1

Standard InChI Key:  KXYZXPAKZCKVCR-UHFFFAOYSA-M

Molfile:  

     RDKit          2D

 35 39  0  0  0  0  0  0  0  0999 V2000
    7.9131  -14.2286    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    2.3749  -13.5672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3738  -14.3937    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0877  -14.8060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0859  -13.1550    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8005  -13.5636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8012  -14.3894    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5158  -14.7999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5101  -13.1500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2251  -13.5567    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2268  -14.3873    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.9431  -14.7988    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6622  -14.3843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9396  -13.1376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6598  -13.5534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3778  -13.1377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9368  -12.3105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6520  -11.8924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3747  -12.3051    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9905  -11.7452    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6483  -10.9865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8212  -11.0776    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0896  -15.6300    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3770  -16.0438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6599  -14.8051    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9466  -14.3925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3789  -16.8677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6628  -17.2773    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6643  -18.1005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3794  -18.5117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0945  -18.0936    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0894  -17.2717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3825  -19.3358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6704  -19.7503    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0976  -19.7452    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  2  0
  3  4  1  0
  4  7  2  0
  6  5  2  0
  5  2  1  0
  6  7  1  0
  7  8  1  0
  8 11  2  0
 10  9  2  0
  9  6  1  0
 10 11  1  0
 10 14  1  0
 11 12  1  0
 12 13  1  0
 13 15  1  0
 14 15  2  0
 15 16  1  0
 16 19  2  0
 18 17  2  0
 17 14  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 18  1  0
  4 23  1  0
 23 24  1  0
  3 25  1  0
 25 26  1  0
 24 27  1  0
 27 28  2  0
 28 29  1  0
 29 30  2  0
 30 31  1  0
 31 32  2  0
 32 27  1  0
 30 33  1  0
 33 34  1  0
 33 35  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: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 454.55

Molecular Weight (Monoisotopic): 454.2013

AlogP: 5.79

#Rotatable Bonds: 5

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: 1.69

CX LogD: 1.69

Aromatic Rings: 4

Heavy Atoms: 34

QED Weighted: 0.36

Np Likeness Score: 0.75

References

1. Sobolova K,Hrabinova M,Hepnarova V,Kucera T,Kobrlova T,Benkova M,Janockova J,Dolezal R,Prchal L,Benek O,Mezeiova E,Jun D,Soukup O,Korabecny J.  (2020)  Discovery of novel berberine derivatives with balanced cholinesterase and prolyl oligopeptidase inhibition profile.,  203  [PMID:32688201] [10.1016/j.ejmech.2020.112593]

Source

Source(1):

• Scientific Literature