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CHEBI:60178 - benzylpenicilloyl-cysteine

ChEBI IDCHEBI:60178
ChEBI Namebenzylpenicilloyl-cysteine
Stars
DefinitionA compound obtained from nucleophilic cleavage of the β-lactam ring of benzylpenicillin by the amino group of L-cysteine.
Last Modified26 September 2017
Submitterzjosephs
DownloadsMolfile
FormulaC19H25N3O6S2
Net Charge0
Average Mass455.558
Monoisotopic Mass455.11848
SMILES[H][C@@]1([C@H](NC(=O)Cc2ccccc2)C(=O)N[C@@H](CS)C(=O)O)N[C@@H](C(=O)O)C(C)(C)S1
InChIInChI=1S/C19H25N3O6S2/c1-19(2)14(18(27)28)22-16(30-19)13(15(24)20-11(9-29)17(25)26)21-12(23)8-10-6-4-3-5-7-10/h3-7,11,13-14,16,22,29H,8-9H2,1-2H3,(H,20,24)(H,21,23)(H,25,26)(H,27,28)/t11-,13+,14-,16+/m0/s1
InChIKeyZKVQVUUPDWIKAR-ZGMNHVEMSA-N
Roles Classification
Chemical Role:
Bronsted acid  A molecular entity capable of donating a hydron to an acceptor (Brønsted base).
ChEBI Ontology
Outgoing Relation(s)
benzylpenicilloyl-cysteine (CHEBI:60178) has functional parent L-cysteine (CHEBI:17561)
benzylpenicilloyl-cysteine (CHEBI:60178) has functional parent benzylpenicillin (CHEBI:18208)
benzylpenicilloyl-cysteine (CHEBI:60178) is a dicarboxylic acid (CHEBI:35692)
benzylpenicilloyl-cysteine (CHEBI:60178) is a thiazolidinedicarboxylic acid (CHEBI:36176)
IUPAC Name 
(2R,4S)-2-{(1R)-2-{[(1R)-1-carboxy-2-sulfanylethyl]amino}-2-oxo-1-[(phenylacetyl)amino]ethyl}-5,5-dimethyl-1,3-thiazolidine-4-carboxylic acid
Synonyms  Source
cysteine derivative of penicillinChEBI
benzylpenicilloyl cysteineChEBI
PNCyChEBI
cysteine derivative of benzylpenicillinChEBI
Registry NumbersSources
Reaxys:64275Reaxys
Citations