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> Main
CHEBI:135748 - lenampicillin
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ChEBI Name
lenampicillin
ChEBI ID
CHEBI:135748
Definition
A penicillanic acid ester that is the (5-methyl-2-oxo-1,3-dioxol-4-yl)methyl ester of ampicillin. It is a prodrug of ampicillin.
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This entity has been manually annotated by the ChEBI Team.
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Formula
C21H23N3O7S
Net Charge
0
Average Mass
461.490
Monoisotopic Mass
461.12567
InChI
InChI=1S/C21H23N3O7S/c1-
10-
12(31-
20(28)
30-
10)
9-
29-
19(27)
15-
21(2,3)
32-
18-
14(17(26)
24(15)
18)
23-
16(25)
13(22)
11-
7-
5-
4-
6-
8-
11/h4-
8,13-
15,18H,9,22H2,1-
3H3,(H,23,25)
/t13-
,14-
,15+,18-
/m1/s1
InChIKey
ZKUKMWMSYCIYRD-ZXFNITATSA-N
SMILES
[H][C@]12SC(C)(C)[C@@H](N1C(=O)[C@H]2NC(=O)[C@H](N)C1=CC=CC=C1)C(=O)OCC1=C(C)OC(=O)O1
Roles Classification
Biological Role
(s):
antimicrobial agent
A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.
(via
heterocyclic antibiotic
)
Application
(s):
prodrug
A compound that, on administration, must undergo chemical conversion by metabolic processes before becoming the pharmacologically active drug for which it is a prodrug.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing
lenampicillin (
CHEBI:135748
)
has functional parent
ampicillin (
CHEBI:28971
)
lenampicillin (
CHEBI:135748
)
has role
prodrug (
CHEBI:50266
)
lenampicillin (
CHEBI:135748
)
is a
ketene acetal (
CHEBI:145408
)
lenampicillin (
CHEBI:135748
)
is a
penicillanic acid ester (
CHEBI:51212
)
IUPAC Name
(5-
methyl-
2-
oxo-
1,3-
dioxol-
4-
yl)methyl (2
S
,5
R
,6
R
)-
6-
{[(2
R
)-
2-
amino-
2-
phenylacetyl]amino}-
3,3-
dimethyl-
7-
oxo-
4-
thia-
1-
azabicyclo[3.2.0]heptane-
2-
carboxylate
INNs
Sources
lenampicilina
WHO MedNet
lenampicillin
ChemIDplus
lénampicilline
WHO MedNet
lenampicillinum
WHO MedNet
Synonyms
Sources
ampicillin 5-methyl-2-oxo-1,3-dioxol-4-yl methyl ester
ChEBI
KBT 1585
DrugCentral
KBT-1585
DrugCentral
Manual Xrefs
Databases
1553
DrugCentral
D08110
KEGG DRUG
View more database links
Registry Number
Type
Source
86273-18-9
CAS Registry Number
ChemIDplus
Citations
Types
Sources
16312302
PubMed citation
Europe PMC
16312500
PubMed citation
Europe PMC
16312550
PubMed citation
Europe PMC
16312570
PubMed citation
Europe PMC
1761182
PubMed citation
Europe PMC
2345375
PubMed citation
Europe PMC
2759930
PubMed citation
Europe PMC
29017833
PubMed citation
Europe PMC
3729355
PubMed citation
Europe PMC
3795477
PubMed citation
Europe PMC
3906167
PubMed citation
Europe PMC
3908737
PubMed citation
Europe PMC
3932547
PubMed citation
Europe PMC
4046172
PubMed citation
Europe PMC
4046173
PubMed citation
Europe PMC
4053214
PubMed citation
Europe PMC
6399011
PubMed citation
Europe PMC
Last Modified
23 October 2020