13-hydroxyberberine

ID: ALA2270082

PubChem CID: 24827073

Max Phase: Preclinical

Molecular Formula: C20H18ClNO5

Molecular Weight: 352.37

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc2c(O)c3[n+](cc2c1OC)CCc1cc2c(cc1-3)OCO2.[Cl-]

Standard InChI:  InChI=1S/C20H17NO5.ClH/c1-23-15-4-3-12-14(20(15)24-2)9-21-6-5-11-7-16-17(26-10-25-16)8-13(11)18(21)19(12)22;/h3-4,7-9H,5-6,10H2,1-2H3;1H

Standard InChI Key:  SAFQLLBOPKXYLB-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 27 30  0  0  0  0  0  0  0  0999 V2000
    3.4266  -19.8207    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.6577  -20.4098    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6559  -18.7683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3663  -19.1746    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3697  -20.0019    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7958  -19.1687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0771  -18.7558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7992  -19.9960    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0838  -20.4124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0866  -21.2355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5175  -20.4028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5186  -21.2322    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8047  -21.6472    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8081  -22.4711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5247  -22.8810    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2393  -22.4609    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2324  -21.6385    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9389  -21.2237    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6514  -21.6281    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9521  -22.8649    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9587  -23.6840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3785  -21.6475    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0611  -20.0016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0565  -19.1766    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8372  -18.9182    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3258  -19.5834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8477  -20.2529    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 23  2  1  0
  2  5  2  0
  4  3  2  0
  3 24  1  0
  4  5  1  0
  4  7  1  0
  5  9  1  0
  8  6  1  0
  6  7  1  0
  8  9  1  0
  8 11  2  0
  9 10  2  0
 10 13  1  0
 12 11  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 12  1  0
 17 18  1  0
 18 19  1  0
 16 20  1  0
 20 21  1  0
 10 22  1  0
 23 24  2  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 27 23  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: 352.37

Molecular Weight (Monoisotopic): 352.1179

AlogP: 2.80

#Rotatable Bonds: 2

Polar Surface Area: 61.03

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 7.09

CX Basic pKa: ┄

CX LogP: -1.59

CX LogD: -2.05

Aromatic Rings: 3

Heavy Atoms: 26

QED Weighted: 0.72

Np Likeness Score: 1.21

References

1. 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