Acetic acid (2S,3R,4S,4aR)-3,4-diacetoxy-6-oxo-2,3,4,4a,5,6-hexahydro-[1,3]dioxolo[4,5-j]phenanthridin-2-yl ester

ID: ALA490147

Chembl Id: CHEMBL490147

PubChem CID: 454223

Max Phase: Preclinical

Molecular Formula: C20H19NO9

Molecular Weight: 417.37

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Lycoricidine Triacetate | [(2S,3R,4S,4aR)-3,4-diacetoxy-6-oxo-3,4,4a,5-tetrahydro-2H-[1,3]dioxolo[4,5-j]phenanthridin-2-yl] acetate|Lycoricidine Triacetate|CHEMBL490147|UYVVJANCFXPLCX-MANSERQUSA-|7-Deoxynarciclasine-2,3,4-O- triacetate|[1,3]Dioxolo[4,5-j]phenanthridin-6(2H)-one, 2,3,4-tris(acetyloxy)-3,4,4a,5-tetrahydro-, (2S,3R,4S,4aR)-|InChI=1/C20H19NO9/c1-8(22)28-16-5-12-11-4-14-15(27-7-26-14)6-13(11)20(25)21-17(12)19(30-10(3)24)18(16)29-9(2)23/h4-6,16-19H,7H2,1-3H3,(H,21,25)/t16-,17+,18+,19-Show More⌵

Canonical SMILES:  CC(=O)O[C@@H]1[C@H](OC(C)=O)[C@@H](OC(C)=O)C=C2c3cc4c(cc3C(=O)N[C@H]21)OCO4

Standard InChI:  InChI=1S/C20H19NO9/c1-8(22)28-16-5-12-11-4-14-15(27-7-26-14)6-13(11)20(25)21-17(12)19(30-10(3)24)18(16)29-9(2)23/h4-6,16-19H,7H2,1-3H3,(H,21,25)/t16-,17+,18+,19-/m0/s1

Standard InChI Key:  UYVVJANCFXPLCX-MANSERQUSA-N

Alternative Forms

1. Parent:

   

   ALA490147

   LYCORICIDINE TRIACETATE

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: 417.37

Molecular Weight (Monoisotopic): 417.1060

AlogP: 0.72

#Rotatable Bonds: 3

Polar Surface Area: 126.46

Molecular Species: NEUTRAL

HBA: 9

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 10

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 0.06

CX LogD: 0.06

Aromatic Rings: 1

Heavy Atoms: 30

QED Weighted: 0.56

Np Likeness Score: 1.48

References

1. Pettit GR, Eastham SA, Melody N, Orr B, Herald DL, McGregor J, Knight JC, Doubek DL, Pettit GR, Garner LC, Bell JA..  (2006)  Isolation and structural modification of 7-deoxynarciclasine and 7-deoxy-trans-dihydronarciclasine.,  69  (1): [PMID:16441059] [10.1021/np058068l]

2. Gabrielsen B, Monath TP, Huggins JW, Kefauver DF, Pettit GR, Groszek G, Hollingshead M, Kirsi JJ, Shannon WM, Schubert EM..  (1992)  Antiviral (RNA) activity of selected Amaryllidaceae isoquinoline constituents and synthesis of related substances.,  55  (11): [PMID:1336040] [10.1021/np50089a003]

3. Chen DZ, Jiang JD, Zhang KQ, He HP, Di YT, Zhang Y, Cai JY, Wang L, Li SL, Yi P, Peng ZG, Hao XJ..  (2013)  Evaluation of anti-HCV activity and SAR study of (+)-lycoricidine through targeting of host heat-stress cognate 70 (Hsc70).,  23  (9): [PMID:23511018] [10.1016/j.bmcl.2013.02.089]

Source

Source(1):

• Scientific Literature