ID: ALA203135

Max Phase: Preclinical

Molecular Formula: C19H16NO4+

Molecular Weight: 322.34

Molecule Type: Small molecule

Representations

Synonyms (1): Berberrubine
Synonyms from Alternative Forms(1):

Canonical SMILES:  COc1ccc2cc3[n+](cc2c1O)CCc1cc2c(cc1-3)OCO2

Standard InChI:  InChI=1S/C19H15NO4/c1-22-16-3-2-11-6-15-13-8-18-17(23-10-24-18)7-12(13)4-5-20(15)9-14(11)19(16)21/h2-3,6-9H,4-5,10H2,1H3/p+1

Standard InChI Key:  GLYPKDKODVRYGP-UHFFFAOYSA-O

Molecule Features

Natural Product: Yes

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

Properties

Molecular Weight: 322.34

Molecular Weight (Monoisotopic): 322.1074

AlogP: 2.79

#Rotatable Bonds: 1

Polar Surface Area: 51.80

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: 0

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 8.27

CX Basic pKa:

CX LogP: -1.43

CX LogD: -1.48

Aromatic Rings: 3

Heavy Atoms: 24

QED Weighted: 0.70

Np Likeness Score: 1.45

References

1. Bian X, He L, Yang G..  (2006)  Synthesis and antihyperglycemic evaluation of various protoberberine derivatives.,  16  (5): [PMID:16359864] [10.1016/j.bmcl.2005.11.045]

2. Park KD, Lee JH, Kim SH, Kang TH, Moon JS, Kim SU..  (2006)  Synthesis of 13-(substituted benzyl) berberine and berberrubine derivatives as antifungal agents.,  16  (15): [PMID:16730982] [10.1016/j.bmcl.2006.05.033]

3. Krivogorsky B, Pernat JA, Douglas KA, Czerniecki NJ, Grundt P..  (2012)  Structure-activity studies of some berberine analogs as inhibitors of Toxoplasma gondii.,  22  (8): [PMID:22425568] [10.1016/j.bmcl.2012.02.038]

4. PubChem BioAssay data set, 

5. 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(2):

• Scientific Literature
• PubChem BioAssays