(1R,2R,4aS,11bR)-2-hydroxy-1-(tetrahydro-2H-pyran-2-yloxy)-1,2,4a,5-tetrahydro-[1,3]dioxolo[4,5-j]phenanthridin-6(11bH)-one

ID: ALA517360

Chembl Id: CHEMBL517360

PubChem CID: 454229

Max Phase: Preclinical

Molecular Formula: C19H21NO6

Molecular Weight: 359.38

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C1N[C@H]2C=C[C@@H](O)[C@H](OC3CCCCO3)[C@@H]2c2cc3c(cc21)OCO3

Standard InChI:  InChI=1S/C19H21NO6/c21-13-5-4-12-17(18(13)26-16-3-1-2-6-23-16)10-7-14-15(25-9-24-14)8-11(10)19(22)20-12/h4-5,7-8,12-13,16-18,21H,1-3,6,9H2,(H,20,22)/t12-,13+,16?,17+,18-/m0/s1

Standard InChI Key:  NZJRRMZGOIUVCT-UIWYPFOVSA-N

Alternative Forms

1. Parent:

   

   ALA517360

   (1R,2R,4aS,11bR)-2-hydroxy-1-tetrahydropyran-2-yloxy-2,4a,5,11b-tetrahydro-1H-[1,3]dioxolo[4,5-j]phenanthridin-6-one

Molecule Features

Natural Product: No

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: 359.38

Molecular Weight (Monoisotopic): 359.1369

AlogP: 1.45

#Rotatable Bonds: 2

Polar Surface Area: 86.25

Molecular Species: NEUTRAL

HBA: 6

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.71

CX Basic pKa: ┄

CX LogP: 1.07

CX LogD: 1.07

Aromatic Rings: 1

Heavy Atoms: 26

QED Weighted: 0.78

Np Likeness Score: 1.45

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