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BRENDA support

Ligand benzylpenicillin

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Basic Ligand Information

Molecular Structure
Picture of benzylpenicillin (click for magnification)
Molecular Formula
BRENDA Name
InChIKey
C16H18N2O4S
benzylpenicillin
JGSARLDLIJGVTE-MBNYWOFBSA-N
Synonyms:
(2S,5R,6R)-3,3-dimethyl-7-oxo-6-[(phenylacetyl)amino]-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, (3H)benzylpenicillin, 6beta-(2-phenyl-acetylamino)-penicillanic acid, ayercillin, benzyl penicillin, penicillin-G, penicillin G, [phenyl-4(n)-3H]benzylpenicillin
Pathway Source
Pathways

Roles as Enzyme Ligand

In Vivo Substrate in Enzyme-catalyzed Reactions (19 results)

EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
penicillin G + H2O = ?
show the reaction diagram
-

In Vivo Product in Enzyme-catalyzed Reactions (3 results)

EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
phenylacetyl-L-cysteinyl-D-valine + O2 = penicillin G + 2 H2O
show the reaction diagram
-

Substrate in Enzyme-catalyzed Reactions (51 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
penicillin G + H2O2 = penicillin G (R)-sulfoxide + H2O
show the reaction diagram
-
penicillin G + 2-oxoglutarate + O2 = ? + succinate + CO2
show the reaction diagram
-
[phenyl-4(n)-3H]benzylpenicillin = ?
show the reaction diagram
-
penicillin G + H2O = 6-aminopenicillanic acid + phenylacetic acid
show the reaction diagram
-
penicillin G + H2O = (2R,4S)-2-[(R)-carboxy[(phenylacetyl)amino]methyl]-5,5-dimethyl-1,3-thiazolidine-4-carboxylic acid
show the reaction diagram
-

Product in Enzyme-catalyzed Reactions (10 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
phenylacetyl-L-cysteinyl-D-valine + O2 = penicillin G + 2 H2O
show the reaction diagram
-

Activator in Enzyme-catalyzed Reactions (2 results)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
leads to slight activation in vivo
-
stimulation, in the presence of 15% methanol, not at higher methanol concentrations or in the presence of deoxycholate
-

Inhibitor in Enzyme-catalyzed Reactions (30 results)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
in vitro inhibition
-
strain 18sH Con-, 450 microg/ml, 50 percent inhibition; strain 18s SAI-, 0.3 microg/ml, 50 percent inhibition
-
no covalent adduct observed
-
20 mM, partial inhibition is enhanced by lysine
-
partial
-
mixed inhibition
-

3D Structure of Enzyme-Ligand-Complex (PDB) (54 results)

Enzyme Kinetic Parameters

kcat Value (Turnover Number) (240 results)

EC NUMBER
TURNOVER NUMBER [1/S]
TURNOVER NUMBER MAXIMUM [1/S]
COMMENTARY
LITERATURE
2.2
-
pH 8.0, 45°C

KM Value (284 results)

EC NUMBER
KM VALUE [MM]
KM VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
155.8
-
pH 8.0, 45°C

Ki Value (2 results)

EC NUMBER
KI VALUE [MM]
KI VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
9.8
-
-
2
-
pH 6.5, 40°C, recombinant wild-type enzyme

IC50 Value (1 result)

EC NUMBER
IC50 VALUE
IC50 VALUE MAXIMUM
COMMENTARY
LITERATURE
0.0049
-
pH 7.0, 37°C

References & Links

Links to other databases for benzylpenicillin

ChEBI
PubChem
ChEBI
PubChem