(2S,3R,4S,4aR,11bS)-6-oxo-1,2,3,4,4a,5,6,11b-octahydro-[1,3]dioxolo[4,5-j]phenanthridine-2,3,4,7-tetrayl tetraacetate

ID: ALA478768

Chembl Id: CHEMBL478768

PubChem CID: 3000374

Max Phase: Preclinical

Molecular Formula: C22H23NO11

Molecular Weight: 477.42

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(=O)Oc1c2c(cc3c1C(=O)N[C@H]1[C@H](OC(C)=O)[C@H](OC(C)=O)[C@@H](OC(C)=O)C[C@@H]31)OCO2

Standard InChI:  InChI=1S/C22H23NO11/c1-8(24)31-15-6-13-12-5-14-18(30-7-29-14)20(33-10(3)26)16(12)22(28)23-17(13)21(34-11(4)27)19(15)32-9(2)25/h5,13,15,17,19,21H,6-7H2,1-4H3,(H,23,28)/t13-,15-,17+,19+,21-/m0/s1

Standard InChI Key:  KFEHMJDKBKJHRD-SSXBFIPSSA-N

Alternative Forms

1. Parent:

   

   ALA478768

   [(2S,3R,4S,4aR,11bS)-3,4,7-triacetyloxy-6-oxo-2,3,4,4a,5,11b-hexahydro-1H-[1,3]dioxolo[4,5-j]phenanthridin-2-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: 477.42

Molecular Weight (Monoisotopic): 477.1271

AlogP: 0.73

#Rotatable Bonds: 4

Polar Surface Area: 152.76

Molecular Species: NEUTRAL

HBA: 11

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 12

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 13.38

CX Basic pKa: ┄

CX LogP: -0.30

CX LogD: -0.30

Aromatic Rings: 1

Heavy Atoms: 34

QED Weighted: 0.37

Np Likeness Score: 1.69

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