3-[(1r,2r,6r)-5-Oxo-7-oxabicyclo[4.1.0]hept-2-yl]-l-alanine
Basic information
- CAS
28978-07-6- Standard SMILES
N[C@@H](C[C@H]1CCC(=O)[C@@H]2O[C@H]12)C(=O)O- InChIKey
KHVZXXWDPSCGEK-ROHCDXGRSA-N- Molecular formula
- C9H13NO4
- Average molar mass
- 199.2 g/mol
- Monoisotopic mass
- 199.0844579
Overview
Anticapsin has been reported in Streptomyces griseoplanus with data available.
Names & identifiers
- Preferred name
- 3-[(1r,2r,6r)-5-Oxo-7-oxabicyclo[4.1.0]hept-2-yl]-l-alanine
- IUPAC
- (2S)-2-amino-3-[(1R,2R,6R)-5-oxo-7-oxabicyclo[4.1.0]heptan-2-yl]propanoic acid
- English name
- anticapsin
- Molecular formula
- C9H13NO4
- Molecular weight
- 199.2
Names & synonyms
NSC1778547-Oxabicyclo[4.1.0]heptane-2-propanoic acid, (1R-(1.alpha.,2.alpha.(S*),6.alpha.))-7-Oxabicyclo[4.1.0]heptane-2-propanoic acid, [1R-[1.alpha.,2.alpha.(S*),6.alpha.]]-3-[(1r,2r,6r)-5-oxo-7-oxabicyclo[4.1.0]hept-2-yl]-l-alanineSCHEMBL29743042KHVZXXWDPSCGEK-ROHCDXGRSA-NAKOS006327913(S)-2-Amino-3-((1R,2R,6R)-5-oxo-7-oxabicyclo[4.1.0]heptan-2-yl)propanoic acidanticapsin(1R,6R,αS)-α-Amino-5-oxo-7-oxabicyclo[4.1.0]heptane-2β-propionic acid7-Oxabicyclo[4.1.0]heptane-2-propanoic acid, α-amino-5-oxo-, (αS,1R,2S,6R)-
Database identifiers
- CAS
28978-07-6- PubChem CID
- 72647
- Nikkaji
- J20.243F
Properties
Computed structural properties
- XLogP
- -3.1
- Topological polar surface area
- 92.9 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 5
- Rotatable bonds
- 3
- Heavy atoms
- 14
- Formal charge
- 0
- Complexity
- 278
Physicochemical properties
- Melting point
- 240 °C · 240 °C (decomp)
- Boiling point
- 415.9 · 415.9±30.0 °C(Predicted)
- Density
- 1.368 · 1.368±0.06 g/cm3(Predicted)
- pka
- 2.25 · 2.25±0.10(Predicted)
- FDA UNII
- 75 PQ0DZ8R2 · 75PQ0DZ8R2
Chemistry & industry
Applications
UsesAnticapsin is a glucosamine-6-phosphate synthase inhibitor with antifungal effects[1].
Additional notes
DefinitionChEBI: An alanine derivative that is L-alanine bearing a 5-oxo-7-oxabicyclo[4.1.0]hept-2-yl substituent at position 3.
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Related reactions
1 records
Compound notes
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