2-Hydroxy-3,8,9-trimethoxy-5-methyl-benzo[c]phenanthridinium chloride

ID: ALA282622

Chembl Id: CHEMBL282622

Cas Number: 52259-64-0

PubChem CID: 40304

Max Phase: Preclinical

Molecular Formula: C21H20ClNO4

Molecular Weight: 350.39

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Fagaronine | Fagaronine Chloride | Fagaronine chloride|52259-64-0|52259-64-0 (chloride)|2-Hydroxy-3,8,9-trimethoxy-5-methylbenzo(c)phenanthridinium chloride|8NA32GM9TE|MLS002702529|BENZO(c)PHENANTHRIDINIUM, 2-HYDROXY-3,8,9-TRIMETHOXY-5-METHYL-, CHLORIDE|NSC157995|NSC-157995|Benzo[c]phenanthridinium, 2-hydroxy-3,8,9-trimethoxy-5-methyl-, chloride (1:1)|NSC 157995|BENZO(C)PHENANTHRIDINIUM, 2-HYDROXY-3,8,9-TRIMETHOXY-5-METHYL-, CHLORIDE (1:1)|UNII-8NA32GM9TE|SCHEMBL424548|CHEMBL282622|BDBM50478514|Show More⌵

Canonical SMILES:  COc1cc2c(ccc3c4cc(OC)c(OC)cc4c[n+](C)c23)cc1O.[Cl-]

Standard InChI:  InChI=1S/C21H19NO4.ClH/c1-22-11-13-8-19(25-3)20(26-4)9-15(13)14-6-5-12-7-17(23)18(24-2)10-16(12)21(14)22;/h5-11H,1-4H3;1H

Standard InChI Key:  VVEPUJCLNRDIEQ-UHFFFAOYSA-N

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: 350.39

Molecular Weight (Monoisotopic): 350.1387

AlogP: 3.70

#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: 8.99

CX Basic pKa: ┄

CX LogP: -0.97

CX LogD: -0.98

Aromatic Rings: 4

Heavy Atoms: 26

QED Weighted: 0.45

Np Likeness Score: 0.99

References

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14. Serbetçi T, Genès C, Depauw S, Prado S, Porée FH, Hildebrand MP, David-Cordonnier MH, Michel S, Tillequin F..  (2010)  Synthesis and biological evaluation of dialkylaminoalkylamino benzo[c][1,7] and [1,8]phenanthrolines as antiproliferative agents.,  45  (6): [PMID:20236738] [10.1016/j.ejmech.2010.02.043]

15. PubChem BioAssay data set, 

16. PubChem BioAssay data set, 

17. Kongkum N, Tuchinda P, Pohmakotr M, Reutrakul V, Piyachaturawat P, Jariyawat S, Suksen K, Akkarawongsapat R, Kasisit J, Napaswad C..  (2013)  Cytotoxic, antitopoisomerase IIα, and anti-HIV-1 activities of triterpenoids isolated from leaves and twigs of Gardenia carinata.,  76  (4): [PMID:23550966] [10.1021/np3006887]

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Source

Source(2):

• Scientific Literature
• PubChem BioAssays