ID: ALA572497

Max Phase: Preclinical

Molecular Formula: C16H15NO4

Molecular Weight: 285.30

Molecule Type: Small molecule

Representations

Synonyms (1): 2-Oxolycorine
Synonyms from Alternative Forms(1):

Canonical SMILES:  O=C1C=C2CCN3Cc4cc5c(cc4[C@H]([C@@H]1O)[C@@H]23)OCO5

Standard InChI:  InChI=1S/C16H15NO4/c18-11-3-8-1-2-17-6-9-4-12-13(21-7-20-12)5-10(9)14(15(8)17)16(11)19/h3-5,14-16,19H,1-2,6-7H2/t14-,15+,16+/m0/s1

Standard InChI Key:  HVPDCMMHMJQOAL-ARFHVFGLSA-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: 285.30

Molecular Weight (Monoisotopic): 285.1001

AlogP: 0.96

#Rotatable Bonds: 0

Polar Surface Area: 59.00

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: 0

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 13.00

CX Basic pKa: 7.25

CX LogP: 0.78

CX LogD: 0.54

Aromatic Rings: 1

Heavy Atoms: 21

QED Weighted: 0.77

Np Likeness Score: 1.90

References

1. 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]

2. 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]

3. 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]

4. 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]

5. 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]

Source

Source(1):

• Scientific Literature