2-[(3aS)-6-formyl-2,2,4-trimethyl-1,3,3a,7a-tetrahydroinden-5-yl]-2-oxoacetic acid
Basic information
- CAS
139748-98-4- Standard SMILES
CC1=C(C(=O)C(=O)O)C(C=O)=CC2CC(C)(C)C[C@H]12- InChIKey
FUUQWZJSFLVSPA-HCCKASOXSA-N- Molecular formula
- C15H18O4
- Average molar mass
- 262.3 g/mol
- Monoisotopic mass
- 262.12050905
Names & identifiers
- Preferred name
- 2-[(3aS)-6-formyl-2,2,4-trimethyl-1,3,3a,7a-tetrahydroinden-5-yl]-2-oxoacetic acid
- IUPAC
- 2-[(3aS)-6-formyl-2,2,4-trimethyl-1,3,3a,7a-tetrahydroinden-5-yl]-2-oxoacetic acid
- English name
- clavicoronic acid
- Molecular formula
- C15H18O4
- Molecular weight
- 262.31
Names & synonyms
2-[(3aS)-6-formyl-2,2,4-trimethyl-1,3,3a,7a-tetrahydroinden-5-yl]-2-oxoacetic acidDTXSID20930577(6-Formyl-2,2,4-trimethyl-2,3,3a,7a-tetrahydro-1H-inden-5-yl)(oxo)acetic acid[(3aS)-6-Formyl-2,2,4-trimethyl-2,3,3a,7a-tetrahydro-1H-inden-5-yl](oxo)acetic acidclavicoronic acid1H-Indene-5-acetic acid, 6-formyl-2,3,3a,7a-tetrahydro-2,2,4-trimethyl-α-oxo-, (3aS,7aS)-
Database identifiers
- CAS
139748-98-4- PubChem CID
- 3035705
- DTXSID
DTXSID20930577
Properties
Computed structural properties
- XLogP
- 2
- Topological polar surface area
- 71.4 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 4
- Rotatable bonds
- 3
- Heavy atoms
- 19
- Formal charge
- 0
- Complexity
- 522
Physicochemical properties
- Boiling point
- 387.9 · 387.9±34.0 °C(Predicted)
- Density
- 1.236 · 1.236±0.06 g/cm3(Predicted)
- pka
- 2.39 · 2.39±0.54(Predicted)
Chemistry & industry
Applications
DescriptionClavicoronic acid is a β-lactam drug that functions as a mechanism-based β-lactamase inhibitor. While not effective by itself as an antibiotic, when combined with penicillin-group antibiotics, it can overcome antibiotic resistance in bacteria that secrete β-lactamase, which otherwise inactivates most penicillins.
UsesClavicoronic acid is an avian myeloblastosis virus and Moloney murine leukemia virus reverse transcriptases inhibitor with Ki values of 130, 68 μM, respectively. Clavicoronic acid inhibits the multiplication of vesicular stomatitis virus by interfering with this virus's RNA-directed RNA-polymerase. Clavicoronic acid shows no cytotoxicity[1].
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