ID: ALA251077

Max Phase: Preclinical

Molecular Formula: C18H19NO5

Molecular Weight: 329.35

Molecule Type: Small molecule

Representations

Synonyms (3): 1-Acetoxylycorine | 1-Acetyllycorine | 1-O-Acetyllycorine
Synonyms from Alternative Forms(3):

Canonical SMILES:  CC(=O)O[C@H]1[C@H]2c3cc4c(cc3CN3CCC(=C[C@@H]1O)[C@H]23)OCO4

Standard InChI:  InChI=1S/C18H19NO5/c1-9(20)24-18-13(21)4-10-2-3-19-7-11-5-14-15(23-8-22-14)6-12(11)16(18)17(10)19/h4-6,13,16-18,21H,2-3,7-8H2,1H3/t13-,16-,17+,18+/m0/s1

Standard InChI Key:  BIGUPJIJZYZJMV-VIBAHUMZSA-N

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: 329.35

Molecular Weight (Monoisotopic): 329.1263

AlogP: 1.32

#Rotatable Bonds: 1

Polar Surface Area: 68.23

Molecular Species: NEUTRAL

HBA: 6

HBD: 1

#RO5 Violations: 0

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 13.76

CX Basic pKa: 7.97

CX LogP: 0.60

CX LogD: -0.07

Aromatic Rings: 1

Heavy Atoms: 24

QED Weighted: 0.62

Np Likeness Score: 2.37

References

1. Wang YH, Zhang ZK, Yang FM, Sun QY, He HP, Di YT, Mu SZ, Lu Y, Chang Y, Zheng QT, Ding M, Dong JH, Hao XJ..  (2007)  Benzylphenethylamine alkaloids from Hosta plantaginea with inhibitory activity against tobacco mosaic virus and acetylcholinesterase.,  70  (9): [PMID:17822295] [10.1021/np0702077]

2. Toriizuka Y, Kinoshita E, Kogure N, Kitajima M, Ishiyama A, Otoguro K, Yamada H, Omura S, Takayama H..  (2008)  New lycorine-type alkaloid from Lycoris traubii and evaluation of antitrypanosomal and antimalarial activities of lycorine derivatives.,  16  (24): [PMID:19013823] [10.1016/j.bmc.2008.10.061]

3. McNulty J, Nair JJ, Singh M, Crankshaw DJ, Holloway AC, Bastida J..  (2009)  Selective cytochrome P450 3A4 inhibitory activity of Amaryllidaceae alkaloids.,  19  (12): [PMID:19428250] [10.1016/j.bmcl.2009.04.086]

4. Lamoral-Theys D, Andolfi A, Van Goietsenoven G, Cimmino A, Le Calvé B, Wauthoz N, Mégalizzi V, Gras T, Bruyère C, Dubois J, Mathieu V, Kornienko A, Kiss R, Evidente A..  (2009)  Lycorine, the main phenanthridine Amaryllidaceae alkaloid, exhibits significant antitumor activity in cancer cells that display resistance to proapoptotic stimuli: an investigation of structure-activity relationship and mechanistic insight.,  52  (20): [PMID:19788245] [10.1021/jm901031h]

5. Cedrón JC, Gutiérrez D, Flores N, Ravelo AG, Estévez-Braun A..  (2010)  Synthesis and antiplasmodial activity of lycorine derivatives.,  18  (13): [PMID:20627737] [10.1016/j.bmc.2010.05.023]

6. McNulty J, Nair JJ, Little JR, Brennan JD, Bastida J..  (2010)  Structure-activity studies on acetylcholinesterase inhibition in the lycorine series of Amaryllidaceae alkaloids.,  20  (17): [PMID:20655219] [10.1016/j.bmcl.2010.06.130]

7. Evdokimov NM, Lamoral-Theys D, Mathieu V, Andolfi A, Frolova LV, Pelly SC, van Otterlo WA, Magedov IV, Kiss R, Evidente A, Kornienko A..  (2011)  In search of a cytostatic agent derived from the alkaloid lycorine: synthesis and growth inhibitory properties of lycorine derivatives.,  19  (23): [PMID:22019045] [10.1016/j.bmc.2011.09.051]

8. Nair JJ, Wilhelm A, Bonnet SL, van Staden J..  (2017)  Antibacterial constituents of the plant family Amaryllidaceae.,  27  (22): [PMID:29033234] [10.1016/j.bmcl.2017.09.052]

9. Dighe SN, Ekwudu O, Dua K, Chellappan DK, Katavic PL, Collet TA..  (2019)  Recent update on anti-dengue drug discovery.,  176  [PMID:31128447] [10.1016/j.ejmech.2019.05.010]

10. Behnam MA, Nitsche C, Boldescu V, Klein CD..  (2016)  The Medicinal Chemistry of Dengue Virus.,  59  (12): [PMID:26771861] [10.1021/acs.jmedchem.5b01653]

Source

Source(1):

• Scientific Literature