(1R,2S,3S,4S,4aR,11bR)-1-hydroxy-6-oxo-1,2,3,4,4a,5,6,11b-octahydro-[1,3]dioxolo[4,5-j]phenanthridine-2,3,4-triyl triacetate

ID: ALA478100

Chembl Id: CHEMBL478100

PubChem CID: 44584630

Max Phase: Preclinical

Molecular Formula: C20H21NO10

Molecular Weight: 435.39

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@H](O)[C@@H]2c3cc4c(cc3C(=O)N[C@H]2[C@@H]1OC(C)=O)OCO4

Standard InChI:  InChI=1S/C20H21NO10/c1-7(22)29-17-15-14(16(25)18(30-8(2)23)19(17)31-9(3)24)10-4-12-13(28-6-27-12)5-11(10)20(26)21-15/h4-5,14-19,25H,6H2,1-3H3,(H,21,26)/t14-,15-,16-,17+,18+,19+/m1/s1

Standard InChI Key:  PNXJTICIFJPDLW-VWQYPGANSA-N

Alternative Forms

1. Parent:

   

   ALA478100

   [(1R,2S,3S,4S,4aR,11bR)-2,3-diacetyloxy-1-hydroxy-6-oxo-2,3,4,4a,5,11b-hexahydro-1H-[1,3]dioxolo[4,5-j]phenanthridin-4-yl] acetate

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: 435.39

Molecular Weight (Monoisotopic): 435.1165

AlogP: -0.22

#Rotatable Bonds: 3

Polar Surface Area: 146.69

Molecular Species: NEUTRAL

HBA: 10

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 11

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 13.57

CX Basic pKa: ┄

CX LogP: -0.94

CX LogD: -0.94

Aromatic Rings: 1

Heavy Atoms: 31

QED Weighted: 0.48

Np Likeness Score: 1.63

References

1. 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]

Source

Source(1):

• Scientific Literature