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ChEBI
> Main
CHEBI:60178 - benzylpenicilloyl-cysteine
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ChEBI Name
benzylpenicilloyl-cysteine
ChEBI ID
CHEBI:60178
Definition
A compound obtained from nucleophilic cleavage of the β-lactam ring of benzylpenicillin by the amino group of
L
-cysteine.
Stars
This entity has been manually annotated by the ChEBI Team.
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Formula
C19H25N3O6S2
Net Charge
0
Average Mass
455.54800
Monoisotopic Mass
455.11848
InChI
InChI=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
InChIKey
ZKVQVUUPDWIKAR-ZGMNHVEMSA-N
SMILES
[H][C@]1(N[C@@H](C(O)=O)C(C)(C)S1)[C@H](NC(=O)Cc1ccccc1)C(=O)N[C@@H](CS)C(O)=O
Roles Classification
Chemical Role
(s):
Bronsted acid
A molecular entity capable of donating a hydron to an acceptor (Br
o
nsted base).
(via
oxoacid
)
View more via ChEBI Ontology
ChEBI Ontology
Outgoing
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
(2
R
,4
S
)-
2-
{(1
R
)-
2-
{[(1
R
)-
1-
carboxy-
2-
sulfanylethyl]amino}-
2-
oxo-
1-
[(phenylacetyl)amino]ethyl}-
5,5-
dimethyl-
1,3-
thiazolidine-
4-
carboxylic acid
Synonyms
Sources
benzylpenicilloyl cysteine
ChEBI
cysteine derivative of benzylpenicillin
ChEBI
cysteine derivative of penicillin
ChEBI
PNCy
ChEBI
Registry Number
Type
Source
64275
Reaxys Registry Number
Reaxys
Citation
Type
Source
13720937
PubMed citation
Europe PMC
Last Modified
26 September 2017