Noracronycine
Basic information
- CAS
13161-79-0- Standard SMILES
Cn1c2ccccc2c(=O)c2c(O)cc3c(c21)C=CC(C)(C)O3- InChIKey
CBXBWBNEFPNSDO-UHFFFAOYSA-N- Molecular formula
- C19H17NO3
- Average molar mass
- 307.3 g/mol
- Monoisotopic mass
- 307.1208434
Overview
Noracronycine is a member of acridines. It is functionally related to an acridone.
Names & identifiers
- Preferred name
- Noracronycine
- IUPAC
- 6-hydroxy-3,3,12-trimethylpyrano[2,3-c]acridin-7-one
- English name
- noracronycine
- Molecular formula
- C19H17NO3
- Molecular weight
- 307.34318
Names & synonyms
NoracronycineNoracronine13161-79-06-hydroxy-3,3,12-trimethylpyrano[2,3-c]acridin-7-oneO4TQA37UF4NSC-1030053,12-Dihydro-6-hydroxy-3,3,12-trimethyl-7H-pyrano(2,3-c)acridin-7-oneDTXSID501571397H-Pyrano(2,3-c)acridin-7-one, 3,12-dihydro-6-hydroxy-3,3,12-trimethyl-6-hydroxy-3,3,12-trimethylpyrano(2,3-c)acridin-7-oneRefChem:166534DTXCID5079630
Show more names
3,3,12-Trimethyl-6-hydroxy-3H-pyrano[2,3-c]acridine-7(12H)-one3,12-Dihydro-6-hydroxy-3,3,12-trimethyl-7H-pyrano[2,3-c]acridin-7-one
NSC1030056-hydroxy-3,3,12-trimethyl-3,12-dihydro-7h-pyrano[2,3-c]acridin-7-one6-hydroxy-3,3,12-trimethyl-pyrano[2,3-c]acridin-7-oneNORACRONYCINNSC 1030056-NORACRONINE6-NORACRONYCINEO-DEMETHYLACRONYCINE
Database identifiers
- CAS
13161-79-0- PubChem CID
- 5320199
- DTXSID
DTXSID50157139- ChEMBL
CHEMBL509922- ChEBI
CHEBI:201861- UNII
- O4TQA37UF4
- Nikkaji
- J14.917I
Properties
Computed structural properties
- XLogP
- 3.9
- Topological polar surface area
- 49.8 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 4
- Rotatable bonds
- 0
- Heavy atoms
- 23
- Formal charge
- 0
- Complexity
- 529
Physicochemical properties
- Melting point
- 198 · 198-200°C
- storage temp.
- -20 °C · Store at -20°C
- form
- A solid
- FDA UNII
- 4 TQA37UF4 · O4TQA37UF4
Chemistry & industry
Applications
Descriptionhis acridinone alkaloid yields bright yellow needles when crystallized from AcOEt or C6H6. It is a very weak base and does not form stable salts. It is insoluble in alkalies and gives no reaction with CHlNl . With methyl sulphate and potassium carbonate, however, it is methylated, giving Acronycine (q.v.). The ultraviolet spectrum has absorption maxima at 255 and 285 mfJ. with shoulders at 305-310 and 410-415 mfJ., there also being an inflexion at 293 mfJ.. The p_x0002_toleuenesulphonate has been prepared as short, yellow needles from C6H6-light petroleum, m.p. l76-8°C. With FeC13 the alkaloid gives a deep green colour.
UsesNoracronycine is an alkaloid originally isolated from G. pentaphylla that has antimalarial activity. It is active against P. yoelii when used at a concentration of 10 μg/mL.
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