Palmatrubine

ID: ALA2270069

PubChem CID: 10547385

Max Phase: Preclinical

Molecular Formula: C20H20ClNO4

Molecular Weight: 338.38

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cc2c(cc1OC)-c1cc3ccc(OC)c(O)c3c[n+]1CC2.[Cl-]

Standard InChI:  InChI=1S/C20H19NO4.ClH/c1-23-17-5-4-12-8-16-14-10-19(25-3)18(24-2)9-13(14)6-7-21(16)11-15(12)20(17)22;/h4-5,8-11H,6-7H2,1-3H3;1H

Standard InChI Key:  DFUDAUWKWTTXFV-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 26 28  0  0  0  0  0  0  0  0999 V2000
   20.6164  -19.8769    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   17.8654  -20.4829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8636  -18.8391    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5751  -19.2460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5785  -20.0744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0065  -19.2401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2868  -18.8266    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0099  -20.0685    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.2936  -20.4854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2964  -21.3097    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.7291  -20.4758    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.7303  -21.3064    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0155  -21.7219    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0189  -22.5469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.7365  -22.9574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.4520  -22.5367    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.4451  -21.7131    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.1525  -21.2978    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.1658  -22.9412    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.1724  -23.7615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1522  -20.0741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1559  -19.2480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4464  -18.8363    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.7350  -19.2450    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4414  -20.4838    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.4408  -21.3042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 21  2  1  0
  2  5  2  0
  4  3  2  0
  3 22  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
 16 19  1  0
 19 20  1  0
 21 22  2  0
 22 23  1  0
 23 24  1  0
 21 25  1  0
 25 26  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: 338.38

Molecular Weight (Monoisotopic): 338.1387

AlogP: 3.08

#Rotatable Bonds: 3

Polar Surface Area: 51.80

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.27

CX Basic pKa: ┄

CX LogP: -1.37

CX LogD: -1.42

Aromatic Rings: 3

Heavy Atoms: 25

QED Weighted: 0.75

Np Likeness Score: 1.28

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