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(2R)-4-Hydroxy-6-methyl-2-(3-methylbutanoyl)-1-oxa-5-azaspiro[2.5]octa-4,6-dien-8-one

HCID 161964
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Basic information

CAS
38473-18-6
Standard SMILES
CC1=CC(=O)C2(O[C@H]2C(=O)CC(C)C)C(=O)N1
InChIKey
DWCXXICTUDDKTB-NUHJPDEHSA-N
Molecular formula
C12H15NO4
Average molar mass
237.25 g/mol
Monoisotopic mass
237.10010796

Names & identifiers

Preferred name
(2R)-4-Hydroxy-6-methyl-2-(3-methylbutanoyl)-1-oxa-5-azaspiro[2.5]octa-4,6-dien-8-one
IUPAC
(2R)-6-methyl-2-(3-methylbutanoyl)-1-oxa-7-azaspiro[2.5]oct-5-ene-4,8-dione
English name
flavipucine
Molecular formula
C12H15NO4
Molecular weight
237.25

Names & synonyms

DTXSID90959351(2R)-4-Hydroxy-6-methyl-2-(3-methylbutanoyl)-1-oxa-5-azaspiro[2.5]octa-4,6-dien-8-one4-Hydroxy-6-methyl-2-(3-methylbutanoyl)-1-oxa-5-azaspiro[2.5]octa-4,6-dien-8-oneFlavipucinflavipucine1-Oxa-5-azaspiro[2.5]oct-6-ene-4,8-dione, 6-methyl-2-(3-methyl-1-oxobutyl)-, (2R,3R)-

Database identifiers

CAS
38473-18-6
PubChem CID
161964
DTXSID
DTXSID90959351

Properties

Computed structural propertiesFilling in

XLogP
0.4
Topological polar surface area
75.8 Ų
Hydrogen bond donors
1
Hydrogen bond acceptors
4
Rotatable bonds
3
Heavy atoms
17
Formal charge
0
Complexity
438

Chemistry & industry

Applications · 1 item

UsesFlavipucine (Flavipucin), a glutarimide antibiotic, is found in the strain of Aspergillus flavipes F-2090/7. Flavipucine has antibacterial activity against B. subtilis. Flavipucine has antiprotozoal activity. Flavipucine has cytotoxic activity against several cancer cells[1][2].

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