ID: ALA282622

Max Phase: Preclinical

Molecular Formula: C21H20ClNO4

Molecular Weight: 350.39

Molecule Type: Small molecule

Representations

Synonyms (2): Fagaronine | Fagaronine Chloride
Synonyms from Alternative Forms(2):

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

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: 0

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 0

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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10. Arisawa M, Pezzuto JM, Bevelle C, Cordell GA..  (1984)  Potential anticancer agents XXXI. N-demethylation of fagaronine.,  47  (3): [PMID:6481359] [10.1021/np50033a009]

11. Pezzuto JM, Che CT, McPherson DD, Zhu JP, Topcu G, Erdelmeier CA, Cordell GA..  (1991)  DNA as an affinity probe useful in the detection and isolation of biologically active natural products.,  54  (6): [PMID:1812211] [10.1021/np50078a006]

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13. Tan GT, Pezzuto JM, Kinghorn AD, Hughes SH..  (1991)  Evaluation of natural products as inhibitors of human immunodeficiency virus type 1 (HIV-1) reverse transcriptase.,  54  (1): [PMID:1710653] [10.1021/np50073a012]

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]

18. Saquib M, Ansari MI, Johnson CR, Khatoon S, Kamil Hussain M, Coop A..  (2019)  Recent advances in the targeting of human DNA ligase I as a potential new strategy for cancer treatment.,  182  [PMID:31499361] [10.1016/j.ejmech.2019.111657]

Source

Source(2):

• Scientific Literature
• PubChem BioAssays