ID: ALA573894

Max Phase: Preclinical

Molecular Formula: C20H23NO6

Molecular Weight: 373.41

Molecule Type: Small molecule

Representations

Canonical SMILES:  CC(=O)O[C@H]1[C@H]2c3cc4c(cc3CN3CC[C@H](C[C@@H]1OC(C)=O)[C@H]23)OCO4

Standard InChI:  InChI=1S/C20H23NO6/c1-10(22)26-17-5-12-3-4-21-8-13-6-15-16(25-9-24-15)7-14(13)18(19(12)21)20(17)27-11(2)23/h6-7,12,17-20H,3-5,8-9H2,1-2H3/t12-,17+,18+,19-,20-/m1/s1

Standard InChI Key:  IUKYXZADSGGCJJ-OHNCIUIWSA-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: 373.41

Molecular Weight (Monoisotopic): 373.1525

AlogP: 1.97

#Rotatable Bonds: 2

Polar Surface Area: 74.30

Molecular Species: BASE

HBA: 7

HBD: 0

#RO5 Violations: 0

HBA (Lipinski): 7

HBD (Lipinski): 0

#RO5 Violations (Lipinski): 0

CX Acidic pKa:

CX Basic pKa: 9.35

CX LogP: 1.22

CX LogD: -0.72

Aromatic Rings: 1

Heavy Atoms: 27

QED Weighted: 0.73

Np Likeness Score: 1.72

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. 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]

Source

Source(1):

• Scientific Literature