4-(Chloromethyl)-4-hydroxy-6,7-dimethyl-3-oxo-1,3,4,7,7a,9a-hexahydropentaleno(1,6a-c)pyran-9-carboxylic acid
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Basic information
- CAS
68026-87-9- Standard SMILES
CC1=CC23[C@H](C=C(C(=O)O)[C@@H]2COC(=O)[C@]3(O)CCl)[C@H]1C- InChIKey
JIBVJJZCSYJNBC-MERSJFMSSA-N- Molecular formula
- C15H17ClO5
- Average molar mass
- 312.74 g/mol
- Monoisotopic mass
- 312.0764513
Names & identifiers
- Preferred name
- 4-(Chloromethyl)-4-hydroxy-6,7-dimethyl-3-oxo-1,3,4,7,7a,9a-hexahydropentaleno(1,6a-c)pyran-9-carboxylic acid
- IUPAC
- (1S,4aR,6aR,7R)-1-(chloromethyl)-1-hydroxy-7,8-dimethyl-2-oxo-4,4a,6a,7-tetrahydropentaleno[1,6a-c]pyran-5-carboxylic acid
- English name
- (1S,9aS)-1-Chloromethyl-1,2,4,4aα,6aβ,7-hexahydro-1α-hydroxy-7α,8-dimethyl-2-oxopentaleno[1,6a-c]pyran-5-carboxylic acid
- Molecular formula
- C15H17ClO5
- Molecular weight
- 312.75
Names & synonyms
DTXSID509874584-(Chloromethyl)-4-hydroxy-6,7-dimethyl-3-oxo-1,3,4,7,7a,9a-hexahydropentaleno(1,6a-c)pyran-9-carboxylic acid4-(Chloromethyl)-4-hydroxy-6,7-dimethyl-3-oxo-1,3,4,7,7a,9a-hexahydropentaleno[1,6a-c]pyran-9-carboxylic acidRefChem:1070063DTXCID701414619(1S,4aR,6aR,7R)-1-(chloromethyl)-1-hydroxy-7,8-dimethyl-2-oxo-4,4a,6a,7-tetrahydropentaleno[1,6a-c]pyran-5-carboxylic acidSCHEMBL29427647Pentaleno(1,3a-c)pyran-5-carboxylic acid, 1,2,4,4a,6a,7-hexadyro-1-(chloromethyl)-7,8-dimethyl-1-hydroxy-2-oxo-(4S,7R,7aR,9aR)-4-(Chloromethyl)-4-hydroxy-6,7-dimethyl-3-oxo-1,3,4,7,7a,9a-hexahydropentaleno[1,6a-c]pyran-9-carboxylic acidAA-57Antibiotic AA-57(1S,9aS)-1-Chloromethyl-1,2,4,4aα,6aβ,7-hexahydro-1α-hydroxy-7α,8-dimethyl-2-oxopentaleno[1,6a-c]pyran-5-carboxylic acid
Show more names
Pentaleno[1,6a-c]pyran-5-carboxylic acid, 1-(chloromethyl)-1,2,4,4a,6a,7-hexahydro-1-hydroxy-7,8-dimethyl-2-oxo-, (1S,4aR,6aR,7R,9aS)-
Database identifiers
- CAS
68026-87-9- PubChem CID
- 198511
- DTXSID
DTXSID50987458
Properties
Computed structural propertiesFilling in
- XLogP
- 0.9
- Topological polar surface area
- 83.8 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 5
- Rotatable bonds
- 2
- Heavy atoms
- 21
- Formal charge
- 0
- Complexity
- 595
Physicochemical properties
- Boiling point
- 544.333 · 544.333±50.00 °C(Press: 760.00 Torr)(predicted)
- Density
- 1.453 · 1.453±0.10 g/cm3(Temp: 25 °C; Press: 760 Torr)(predicted)
- pka
- 4.172 · 4.172±0.70(predicted)
Chemistry & industry
Applications
DescriptionAA 57 is an antibiotic related to pentalenolactone.
UsesAA-57 is an acidic lipophilic antibiotic isolated from the fermentation broth of Actinomycetes strain AA-57. The AA-57 strain was isolated from a soil sample collected in Koriyama City, Fukushima Prefecture, Japan. AA-57 has antibacterial properties against Gram-positive bacteria, Gram-negative bacteria, and acid-fast bacteria. AA-57 was discovered by screening actinomycete cultures for antibacterial properties. AA-57 exhibits significant antibacterial activity and has inhibitory effects against a variety of bacteria. The discovery of AA-57 provides new possibilities for antibacterial therapy.
Related reactions
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Compound notes
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