2-Amino-3-(2-methylenecyclopropyl)propanoic acid
Basic information
- CAS
156-56-9- Standard SMILES
C=C1CC1CC(N)C(=O)O- InChIKey
OOJZCXFXPZGUBJ-UHFFFAOYSA-N- Molecular formula
- C7H11NO2
- Average molar mass
- 141.17 g/mol
- Monoisotopic mass
- 141.07897859
Overview
2-amino-3-(2-methylenecyclopropyl)propanoic acid is a non-proteinogenic alpha-amino acid that is alanine in which one of the methyl hydrogens has been replaced by a 2-methylenecyclopropyl group. The phytotoxin known as hypoglycin A is a mixture of the diastereoisomers that have L configuration at the amino-bearing carbon. It is a member of cyclopropanes, an olefinic compound and a non-proteinogenic alpha-amino acid.
Names & identifiers
- Preferred name
- 2-Amino-3-(2-methylenecyclopropyl)propanoic acid
- IUPAC
- 2-amino-3-(2-methylidenecyclopropyl)propanoic acid
Names & synonyms
2-amino-3-(2-methylenecyclopropyl)propanoic acidCHEBI:136270RefChem:1062149Hypoglycine.beta.-(Methylenecyclopropyl)alanine.alpha.-Aminomethylenecyclopropanepropionic acid.alpha.-Amino-2-methylenecyclopropanepropionic acidCyclopropanepropanoic acid, .alpha.-amino-2-methylene-L-.alpha.-Amino-.beta.-methylenecyclopropanepropionic acid.alpha.-Amino-.beta.-(2-methylenecyclopropyl)propionic acid(S)-Hypoglycine A, 85%Cyclopropanealanine, L-
Show more names
SCHEMBL956162Cyclopropanepropionic acid, .alpha.-amino-2-methylene-, L-(+)-2-MethyleneL-CyclopropanealanineCyclopropanepropanoic acid, .alpha.-amino-2-methylene-, (.alpha.S,1R)-WLN: L3YTJ AU1 B1YZVQOOJZCXFXPZGUBJ-UHFFFAOYSA-N3-(2-Methylenecyclopropyl)alanineCyclopropanepropionic acid, L-(+)-
Database identifiers
- CAS
156-56-9- PubChem CID
- 9081
- ChEBI
CHEBI:136270
Properties
Computed structural properties
- XLogP
- -2.5
- Topological polar surface area
- 63.3 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 3
- Rotatable bonds
- 3
- Heavy atoms
- 10
- Formal charge
- 0
- Complexity
- 176
Experimental & physicochemical properties
Melting Point280 - 284 °C
Physical DescriptionSolid
Chemistry & industry
Pharmacology
Cellular LocationsCytoplasm
Related reactions
0 records
No reaction records under the current filter.
Compound notes
Loading…