Acutumidine
Basic information
- CAS
18145-26-1- Standard SMILES
COC1=CC(=O)[C@@]2([C@@H]1O)[C@@H](Cl)C[C@]13NCC[C@]21CC(=O)C(OC)=C3OC- InChIKey
SBALNGLYQFMKPR-NQTWQHAWSA-N- Molecular formula
- C18H22ClNO6
- Average molar mass
- 383.8 g/mol
- Monoisotopic mass
- 383.1135651
Overview
Acutumidine is an alkaloid.
Names & identifiers
- Preferred name
- Acutumidine
- IUPAC
- (1S,4'S,6S,10R,11S)-11-chloro-4'-hydroxy-3',4,5-trimethoxyspiro[7-azatricyclo[4.3.3.01,6]dodec-4-ene-10,5'-cyclopent-2-ene]-1',3-dione
- English name
- Acutumidine
- Molecular formula
- C18H22ClNO6
- Molecular weight
- 383.82338
Names & synonyms
Acutumidine18145-26-1DTXSID90331971(1S,4'S,6S,10R,11S)-11-chloro-4'-hydroxy-3',4,5-trimethoxyspiro[7-azatricyclo[4.3.3.01,6]dodec-4-ene-10,5'-cyclopent-2-ene]-1',3-dione(1S,4'S,6S,10R,11S)-11-chloro-4'-hydroxy-3',4,5-trimethoxyspiro(7-azatricyclo(4.3.3.01,6)dodec-4-ene-10,5'-cyclopent-2-ene)-1',3-dioneRefChem:109612DTXCID70283065CHEMBL237548C10565AC1L9DHTCHEBI:2452orb3024647
Show more names
(1R,3'aS,5S,7'aS,9'S)-9'-Chloro-2',3'-dihydro-5-hydroxy-4,6',7'-trimethoxyspiro[3-cyclopentene-1,10'-[3a,7a]propano[1H]indole]-2,5'(4'H)-dioneSpiro[3-cyclopentene-1,10'-[3a,7a]propano[1H]indole]-2,5'(4'H)-dione, 9'-chloro-2',3'-dihydro-5-hydroxy-4,6',7'-trimethoxy-, (1R,3'aS,5S,7'aS,9'S)-
SCHEMBL29414423TN10274Q27105673(1R,2'S,3'aS,5S,7'aS)-2'-Chloro-5-hydroxy-4,4',5'-trimethoxy-2',3'-dihydrospiro[cyclopent-3-ene-1,1'-[3a,7a](epiminoethano)indene]-2,6'(7'H)-dione
Database identifiers
Properties
Computed structural properties
- XLogP
- -0.8
- Topological polar surface area
- 94.1 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 7
- Rotatable bonds
- 3
- Heavy atoms
- 26
- Formal charge
- 0
- Complexity
- 763
Physicochemical properties
- Melting point
- 239 · 239-241 °C (decomp)
- Boiling point
- 693.1 · 693.1±55.0 °C(Predicted)
- Density
- 1.43 · 1.43±0.1 g/cm3(Predicted)
- pka
- 11.06 · 11.06±0.70(Predicted)
Chemistry & industry
Applications
UsesAcutumidine (compound 4) is an alkaloid with anti-HBV activity that can be isolated from Hypserpa nitida Miers. Acutumidine inhibits the production of HBsAg in Hep G2.2.15 cells stably transfected with HBV genome with an IC50 value of 2.023 mM[1].
Additional notes
DefinitionChEBI: Acutumidine is an alkaloid.
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