1,2-Di-O-acetyllycorine

ID: ALA465295

PubChem CID: 10429288

Max Phase: Preclinical

Molecular Formula: C20H21NO6

Molecular Weight: 371.39

Molecule Type: Small molecule

Names and Identifiers

Synonyms: 1,2-Diacetoxylycorine | 1,2-Diacetyllycorine | 1,2-Diacetoxylycorine|1,2-Diacetyllycorine|CHEMBL465295|LYCORINE DIACETATE|1,2-Di-O-acetyllycorine|SCHEMBL12319317|BDBM50293602|PD179165|(1S,17S,18S,19S)-17-(acetyloxy)-5,7-dioxa-12-azapentacyclo[10.6.1.0^{2,10}.0^{4,8}.0^{15,19}]nonadeca-2,4(8),9,15-tetraen-18-yl acetate|(1S,2S,12bS,12cS)-1,2-Diol-2,4,5,7,12b,12c-hexahydro-1H-[1,3]dioxolo[4,5-j]pyrrolo[3,2,1-de]phenanthridine-1,2-diacetate

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

Standard InChI:  InChI=1S/C20H21NO6/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/h5-7,17-20H,3-4,8-9H2,1-2H3/t17-,18-,19+,20+/m0/s1

Standard InChI Key:  LMZHAKUXAHOCST-VNTMZGSJSA-N

Molfile:  

     RDKit          2D

 29 33  0  0  0  0  0  0  0  0999 V2000
   11.4001   -1.8024    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4001   -0.1565    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1117   -0.5732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1133   -1.3982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8235   -1.8038    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8202   -0.1579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2568    0.6597    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5404    1.0750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8214    0.6692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2503   -0.1699    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5364   -0.5726    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5392   -1.3969    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.5131   -1.4677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8538   -0.7198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6885   -1.3982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6886   -0.5663    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9017   -0.3139    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.4144   -0.9843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9016   -1.6503    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.0939    0.2266    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.5615    0.2519    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.1119    1.9095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3955    2.3269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8317    2.3212    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.2676    2.3051    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2763    3.1342    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9815    1.8830    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.1086    1.0845    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.5489    1.9000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5 12  1  0
  6 11  1  0
  6  9  1  0
 10  7  2  0
  7  8  1  0
  8  9  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 10  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 15  1  0
  6 20  1  1
 11 21  1  6
 16  2  1  0
 22 23  1  0
 15  1  1  0
 22 24  2  0
  1  4  2  0
  3  2  2  0
 25 26  1  0
  3  4  1  0
 25 27  2  0
  6  3  1  0
  4  5  1  0
  9 28  1  6
 28 22  1  0
  8 29  1  1
 29 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA465295

   1,2-Diacetoxylycorine

2. Alternative Forms:

   

   ALA465295

   ---

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

Calculated Properties

Molecular Weight: 371.39

Molecular Weight (Monoisotopic): 371.1369

AlogP: 1.89

#Rotatable Bonds: 2

Polar Surface Area: 74.30

Molecular Species: NEUTRAL

HBA: 7

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 8.26

CX LogP: 1.04

CX LogD: 0.13

Aromatic Rings: 1

Heavy Atoms: 27

QED Weighted: 0.58

Np Likeness Score: 2.10

References

1. 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]

2. 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]

3. 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]

4. Kaur K, Jain M, Kaur T, Jain R..  (2009)  Antimalarials from nature.,  17  (9): [PMID:19299148] [10.1016/j.bmc.2009.02.050]

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. 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]

8. Nair JJ, van Staden J..  (2019)  Antiprotozoal alkaloid principles of the plant family Amaryllidaceae.,  29  (20): [PMID:31515186] [10.1016/j.bmcl.2019.126642]

Source

Source(1):

• Scientific Literature