CHEBI:136270 - 2-amino-3-(2-methylenecyclopropyl)propanoic acid

Main ChEBI Ontology Automatic Xrefs Reactions Pathways Models
ChEBI Name 2-amino-3-(2-methylenecyclopropyl)propanoic acid
ChEBI ID CHEBI:136270
Definition A non-proteinogenic α-amino acid that is alanine in which one of the methyl hydrogens has been replaced by a 2-methylenecyclopropyl group.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.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
Download Molfile XML SDF
Formula C7H11NO2
Net Charge 0
Average Mass 141.168
Monoisotopic Mass 141.07898
InChI InChI=1S/C7H11NO2/c1-4-2-5(4)3-6(8)7(9)10/h5-6H,1-3,8H2,(H,9,10)
InChIKey OOJZCXFXPZGUBJ-UHFFFAOYSA-N
SMILES C1(C(=C)C1)CC(C(O)=O)N
Roles Classification
Chemical Role(s): Bronsted base
A molecular entity capable of accepting a hydron from a donor (Bronsted acid).
(via organic amino compound )
Bronsted acid
A molecular entity capable of donating a hydron to an acceptor (Bronsted base).
(via oxoacid )
View more via ChEBI Ontology
ChEBI Ontology
Outgoing 2-amino-3-(2-methylenecyclopropyl)propanoic acid (CHEBI:136270) is a cyclopropanes (CHEBI:51454)
2-amino-3-(2-methylenecyclopropyl)propanoic acid (CHEBI:136270) is a non-proteinogenic α-amino acid (CHEBI:83925)
2-amino-3-(2-methylenecyclopropyl)propanoic acid (CHEBI:136270) is a olefinic compound (CHEBI:78840)
Incoming (2S,4R)-hypoglycin A (CHEBI:134620) is a 2-amino-3-(2-methylenecyclopropyl)propanoic acid (CHEBI:136270)
(2S,4S)-hypoglycin A (CHEBI:6248) is a 2-amino-3-(2-methylenecyclopropyl)propanoic acid (CHEBI:136270)
IUPAC Name
3-(2-methylenecyclopropyl)alanine
Synonyms Sources
2-amino-3-(2-methylenecyclopropyl)propanoic acid IUPAC
2-amino-3-(2-methylenecyclopropyl)propionic acid ChEBI
Manual Xref Database
CPD-9699 MetaCyc
View more database links
Last Modified
28 February 2017
General Comment
2017-02-28 This is the entry for material with unspecified stereochemistry. There are separate entries for hypoglycin A and its components, the individual diastereoisomers (2S,4R)-hypoglycin A and (2S,4S)-hypoglycin A.