BENZYLPENICILLIN

/static/temp/default.svg Search structure
Synonyms
Status
Molecule Category Free-form
ATC J01CE01 S01AA14
UNII Q42T66VG0C
EPA CompTox DTXSID5046934

Structure

InChI Key JGSARLDLIJGVTE-MBNYWOFBSA-N
Smiles CC1(C)S[C@@H]2[C@H](NC(=O)Cc3ccccc3)C(=O)N2[C@H]1C(=O)O
InChI
InChI=1S/C16H18N2O4S/c1-16(2)12(15(21)22)18-13(20)11(14(18)23-16)17-10(19)8-9-6-4-3-5-7-9/h3-7,11-12,14H,8H2,1-2H3,(H,17,19)(H,21,22)/t11-,12+,14-/m1/s1

Physicochemical Descriptors

Property Name Value
Molecular Formula C16H18N2O4S
Molecular Weight 334.4
AlogP 0.86
Hydrogen Bond Acceptor 4.0
Hydrogen Bond Donor 2.0
Number of Rotational Bond 4.0
Polar Surface Area 86.71
Molecular species ACID
Aromatic Rings 1.0
Heavy Atoms 23.0
Assay Description Organism Bioactivity Reference
Inhibition of Enterobacter cloacae S3 isolate beta lactamase LAP1 expressed in Escherichia coli DH10B Enterobacter cloacae 80.0 nM
Inhibition of methicillin-resistant Staphylococcus aureus ATCC 433000 PBP2a assessed as residual activity at 100 uM after 16 hrs Staphylococcus aureus 13.0 %
Inhibition of Enterococcus faecium PBP5fm assessed as residual activity at 100 uM after 16 hrs Enterococcus faecium 10.0 %
Inhibition of Streptococcus pneumoniae 5204 PBP2x assessed as residual activity at 100 uM after 16 hrs Streptococcus pneumoniae 5.0 %
Antibacterial activity against Bacillus subtilis ATCC 6633 after 24 hrs by MTT method Bacillus subtilis 1.562 ug.mL-1
Antibacterial activity against Staphylococcus aureus ATCC 6538 after 24 hrs by MTT method Staphylococcus aureus 1.562 ug.mL-1
Antibacterial activity against Escherichia coli ATCC 35218 after 24 hrs by MTT method Escherichia coli 6.25 ug.mL-1
Antibacterial activity against Pseudomonas aeruginosa ATCC 13525 after 24 hrs by MTT method Pseudomonas aeruginosa 6.25 ug.mL-1
Inhibition of PBP1 in penicillin-resistant Enterococcus faecium D63r membranes assessed as inhibition of fluorescent ampicillin binding after 20 mins at 37 degC Enterococcus faecium 1.6 ug.mL-1
Inhibition of PBP2 in penicillin-resistant Enterococcus faecium D63r membranes assessed as inhibition of fluorescent ampicillin binding after 20 mins at 37 degC Enterococcus faecium 0.06 ug.mL-1
Inhibition of PBP3 in penicillin-resistant Enterococcus faecium D63r membranes assessed as inhibition of fluorescent ampicillin binding after 20 mins at 37 degC Enterococcus faecium 0.6 ug.mL-1
Inhibition of PBP4 in penicillin-resistant Enterococcus faecium D63r membranes assessed as inhibition of fluorescent ampicillin binding after 20 mins at 37 degC Enterococcus faecium 8.0 ug.mL-1
Inhibition of PBP5 in penicillin-resistant Enterococcus faecium D63r membranes assessed as inhibition of fluorescent ampicillin binding after 20 mins at 37 degC Enterococcus faecium 55.0 ug.mL-1
Inhibition of low-affinity PBP5fm in penicillin-resistant Enterococcus faecium D63r membranes assessed as inhibition of fluorescent ampicillin binding after 20 mins at 37 degC Enterococcus faecium 8.0 ug.mL-1
Inhibition of PBP6 in penicillin-resistant Enterococcus faecium D63r membranes assessed as inhibition of fluorescent ampicillin binding after 20 mins at 37 degC Enterococcus faecium 2.0 ug.mL-1
Inhibition of PBP1 in wild type Enterococcus faecium D63 membranes assessed as inhibition of fluorescent ampicillin binding after 20 mins at 37 degC Enterococcus faecium 0.9 ug.mL-1
Inhibition of PBP2 in wild type Enterococcus faecium D63 membranes assessed as inhibition of fluorescent ampicillin binding after 20 mins at 37 degC Enterococcus faecium 0.1 ug.mL-1
Inhibition of PBP3 in wild type Enterococcus faecium D63 membranes assessed as inhibition of fluorescent ampicillin binding after 20 mins at 37 degC Enterococcus faecium 1.3 ug.mL-1
Inhibition of PBP4 in wild type Enterococcus faecium D63 membranes assessed as inhibition of fluorescent ampicillin binding after 20 mins at 37 degC Enterococcus faecium 10.0 ug.mL-1
Inhibition of PBP5 in wild type Enterococcus faecium D63 membranes assessed as inhibition of fluorescent ampicillin binding after 20 mins at 37 degC Enterococcus faecium 75.0 ug.mL-1
Inhibition of low-affinity PBP5fm in wild type Enterococcus faecium D63 membranes assessed as inhibition of fluorescent ampicillin binding after 20 mins at 37 degC Enterococcus faecium 6.0 ug.mL-1
Inhibition of PBP6 in wild type Enterococcus faecium D63 membranes assessed as inhibition of fluorescent ampicillin binding after 20 mins at 37 degC Enterococcus faecium 1.5 ug.mL-1
Binding affinity to methicillin-, vancomycin-susceptible Staphylococcus aureus ATCC 29213 PBP1 by competitive binding assay Staphylococcus aureus 4.0 ug.mL-1
Binding affinity to methicillin-resistant, heteroresistant vancomycin-intermediate, beta-lactamase-negative Staphylococcus aureus 873 PBP1 by competitive binding assay Staphylococcus aureus 0.5 ug.mL-1
Binding affinity to methicillin-, vancomycin-resistant, beta-lactamase-positive Staphylococcus aureus 510 PBP1 by competitive binding assay Staphylococcus aureus 128.0 ug.mL-1
Binding affinity to methicillin-, linezolid-resistant, vancomycin-intermediate, beta-lactamase-positive Staphylococcus aureus 2149A PBP1 by competitive binding assay Staphylococcus aureus 2.0 ug.mL-1
Binding affinity to methicillin-resistant, vancomycin-intermediate, beta-lactamase-positive Staphylococcus aureus 1287 PBP1 by competitive binding assay Staphylococcus aureus 4.0 ug.mL-1
Binding affinity to against methicillin-, daptomycin-resistant, vancomycin-intermediate, beta-lactamase-positive Staphylococcus aureus 25 PBP1 by competitive binding assay Staphylococcus aureus 0.5 ug.mL-1
Binding affinity to methicillin-, vancomycin-susceptible Staphylococcus aureus ATCC 29213 PBP2 by competitive binding assay Staphylococcus aureus 8.0 ug.mL-1
Binding affinity to methicillin-resistant, heteroresistant vancomycin-intermediate, beta-lactamase-negative Staphylococcus aureus 873 PBP2 by competitive binding assay Staphylococcus aureus 0.5 ug.mL-1
Binding affinity to methicillin-, vancomycin-resistant, beta-lactamase-positive Staphylococcus aureus 510 PBP2 by competitive binding assay Staphylococcus aureus 64.0 ug.mL-1
Binding affinity to methicillin-, linezolid-resistant, vancomycin-intermediate, beta-lactamase-positive Staphylococcus aureus 2149A PBP2 by competitive binding assay Staphylococcus aureus 128.0 ug.mL-1
Binding affinity to methicillin-resistant, vancomycin-intermediate, beta-lactamase-positive Staphylococcus aureus 1287 PBP2 by competitive binding assay Staphylococcus aureus 4.0 ug.mL-1
Binding affinity to against methicillin-, daptomycin-resistant, vancomycin-intermediate, beta-lactamase-positive Staphylococcus aureus 25 PBP2 by competitive binding assay Staphylococcus aureus 1.0 ug.mL-1
Binding affinity to methicillin-resistant, heteroresistant vancomycin-intermediate, beta-lactamase-negative Staphylococcus aureus 873 PBP2a by competitive binding assay Staphylococcus aureus 64.0 ug.mL-1
Binding affinity to methicillin-, vancomycin-resistant, beta-lactamase-positive Staphylococcus aureus 510 PBP2a by competitive binding assay Staphylococcus aureus 64.0 ug.mL-1
Binding affinity to methicillin-, linezolid-resistant, vancomycin-intermediate, beta-lactamase-positive Staphylococcus aureus 2149A PBP2a by competitive binding assay Staphylococcus aureus 2.0 ug.mL-1
Binding affinity to methicillin-resistant, vancomycin-intermediate, beta-lactamase-positive Staphylococcus aureus 1287 PBP2a by competitive binding assay Staphylococcus aureus 4.0 ug.mL-1
Binding affinity to against methicillin-, daptomycin-resistant, vancomycin-intermediate, beta-lactamase-positive Staphylococcus aureus 25 PBP2a by competitive binding assay Staphylococcus aureus 4.0 ug.mL-1
Binding affinity to methicillin-, vancomycin-susceptible Staphylococcus aureus ATCC 29213 PBP3 by competitive binding assay Staphylococcus aureus 1.0 ug.mL-1
Binding affinity to methicillin-resistant, heteroresistant vancomycin-intermediate, beta-lactamase-negative Staphylococcus aureus 873 PBP3 by competitive binding assay Staphylococcus aureus 0.03 ug.mL-1
Binding affinity to methicillin-, vancomycin-resistant, beta-lactamase-positive Staphylococcus aureus 510 PBP3 by competitive binding assay Staphylococcus aureus 4.0 ug.mL-1
Binding affinity to methicillin-, linezolid-resistant, vancomycin-intermediate, beta-lactamase-positive Staphylococcus aureus 2149A PBP3 by competitive binding assay Staphylococcus aureus 2.0 ug.mL-1
Binding affinity to methicillin-resistant, vancomycin-intermediate, beta-lactamase-positive Staphylococcus aureus 1287 PBP3 by competitive binding assay Staphylococcus aureus 0.25 ug.mL-1
Binding affinity to against methicillin-, daptomycin-resistant, vancomycin-intermediate, beta-lactamase-positive Staphylococcus aureus 25 PBP3 by competitive binding assay Staphylococcus aureus 0.5 ug.mL-1
Binding affinity to methicillin-, vancomycin-susceptible Staphylococcus aureus ATCC 29213 PBP4 by competitive binding assay Staphylococcus aureus 8.0 ug.mL-1
Binding affinity to methicillin-resistant, heteroresistant vancomycin-intermediate, beta-lactamase-negative Staphylococcus aureus 873 PBP4 by competitive binding assay Staphylococcus aureus 128.0 ug.mL-1
Binding affinity to methicillin-, vancomycin-resistant, beta-lactamase-positive Staphylococcus aureus 510 PBP4 by competitive binding assay Staphylococcus aureus 64.0 ug.mL-1
Binding affinity to methicillin-, linezolid-resistant, vancomycin-intermediate, beta-lactamase-positive Staphylococcus aureus 2149A PBP4 by competitive binding assay Staphylococcus aureus 128.0 ug.mL-1
Binding affinity to methicillin-resistant, vancomycin-intermediate, beta-lactamase-positive Staphylococcus aureus 1287 PBP4 by competitive binding assay Staphylococcus aureus 4.0 ug.mL-1
PUBCHEM_BIOASSAY: Luminescence Microorganism-Based Dose Response HTS to Identify Compounds Cytotoxic to Streptococcus. (Class of assay: confirmatory) [Related pubchem assays: 1900 (Counter Screen), 1677 (Project Summary), 1902 (Retest at Dose), 1662 (Primary HTS)] Streptococcus 60.0 nM
PUBCHEM_BIOASSAY: Luminescence Microorganism-Based Dose Confirmation HTS to Identify Compounds Cytotoxic to SK(-)GAS Group A Streptococcus. (Class of assay: confirmatory) [Related pubchem assays: 1677 (Project Summary), 1662 (Primary HTS)] Streptococcus 60.0 nM
PUBCHEM_BIOASSAY: Luminescence Microorganism-Based Dose Confirmation HTS to Identify Inhibitors of Streptokinase Promotor Activity. (Class of assay: confirmatory) [Related pubchem assays: 1677 (Project Summary), 1662 (Primary HTS)] Streptococcus pyogenes M1 GAS 60.0 nM
Displacement of Biocillin FL from Streptococcus pneumoniae 24 PBP1A Streptococcus pneumoniae 0.008 ug.mL-1
Displacement of Biocillin FL from Streptococcus pneumoniae 3413 PBP1A Streptococcus pneumoniae 0.02 ug.mL-1
Displacement of Biocillin FL from Streptococcus pneumoniae 2527 PBP1A Streptococcus pneumoniae 0.002 ug.mL-1
Displacement of Biocillin FL from Streptococcus pneumoniae 3676 PBP1A Streptococcus pneumoniae 0.012 ug.mL-1
Displacement of Biocillin FL from Streptococcus pneumoniae 3243 PBP1A Streptococcus pneumoniae 0.008 ug.mL-1
Displacement of Biocillin FL from Streptococcus pneumoniae 3665 PBP1A Streptococcus pneumoniae 0.031 ug.mL-1
Displacement of Biocillin FL from Streptococcus pneumoniae 3009 PBP1A Streptococcus pneumoniae 0.009 ug.mL-1
Displacement of Biocillin FL from Streptococcus pneumoniae 1076 PBP1A Streptococcus pneumoniae 0.016 ug.mL-1
Displacement of Biocillin FL from Streptococcus pneumoniae 1077 PBP1A Streptococcus pneumoniae 0.009 ug.mL-1
Displacement of Biocillin FL from Streptococcus pneumoniae 24 PBP1B Streptococcus pneumoniae 0.248 ug.mL-1
Displacement of Biocillin FL from Streptococcus pneumoniae 3413 PBP1B Streptococcus pneumoniae 0.205 ug.mL-1
Displacement of Biocillin FL from Streptococcus pneumoniae 2527 PBP1B Streptococcus pneumoniae 0.009 ug.mL-1
Displacement of Biocillin FL from Streptococcus pneumoniae 3676 PBP1B Streptococcus pneumoniae 0.021 ug.mL-1
Displacement of Biocillin FL from Streptococcus pneumoniae 3243 PBP1B Streptococcus pneumoniae 0.01 ug.mL-1
Displacement of Biocillin FL from Streptococcus pneumoniae 3665 PBP1B Streptococcus pneumoniae 0.029 ug.mL-1
Displacement of Biocillin FL from Streptococcus pneumoniae 3009 PBP1B Streptococcus pneumoniae 0.001 ug.mL-1
Displacement of Biocillin FL from Streptococcus pneumoniae 1076 PBP1B Streptococcus pneumoniae 0.007 ug.mL-1
Displacement of Biocillin FL from Streptococcus pneumoniae 1077 PBP1B Streptococcus pneumoniae 0.005 ug.mL-1
Displacement of Biocillin FL from Streptococcus pneumoniae 24 PBP2X Streptococcus pneumoniae 0.323 ug.mL-1
Displacement of Biocillin FL from Streptococcus pneumoniae 3413 PBP2X Streptococcus pneumoniae 0.642 ug.mL-1
Displacement of Biocillin FL from Streptococcus pneumoniae 2527 PBP2X Streptococcus pneumoniae 0.009 ug.mL-1
Displacement of Biocillin FL from Streptococcus pneumoniae 3676 PBP2X Streptococcus pneumoniae 0.028 ug.mL-1
Displacement of Biocillin FL from Streptococcus pneumoniae 3243 PBP2X Streptococcus pneumoniae 0.007 ug.mL-1
Displacement of Biocillin FL from Streptococcus pneumoniae 3665 PBP2X Streptococcus pneumoniae 0.041 ug.mL-1
Displacement of Biocillin FL from Streptococcus pneumoniae 3009 PBP2X Streptococcus pneumoniae 0.011 ug.mL-1
Displacement of Biocillin FL from Streptococcus pneumoniae 1076 PBP2X Streptococcus pneumoniae 0.01 ug.mL-1
Displacement of Biocillin FL from Streptococcus pneumoniae 1077 PBP2X Streptococcus pneumoniae 0.008 ug.mL-1
Displacement of Biocillin FL from Streptococcus pneumoniae 24 PBP2A Streptococcus pneumoniae 0.133 ug.mL-1
Displacement of Biocillin FL from Streptococcus pneumoniae 3413 PBP2A Streptococcus pneumoniae 0.015 ug.mL-1
Displacement of Biocillin FL from Streptococcus pneumoniae 2527 PBP2A Streptococcus pneumoniae 0.023 ug.mL-1
Displacement of Biocillin FL from Streptococcus pneumoniae 3676 PBP2A Streptococcus pneumoniae 0.013 ug.mL-1
Displacement of Biocillin FL from Streptococcus pneumoniae 3665 PBP2A Streptococcus pneumoniae 0.016 ug.mL-1
Displacement of Biocillin FL from Streptococcus pneumoniae 3009 PBP2A Streptococcus pneumoniae 0.011 ug.mL-1
Displacement of Biocillin FL from Streptococcus pneumoniae 1076 PBP2A Streptococcus pneumoniae 0.02 ug.mL-1
Displacement of Biocillin FL from Streptococcus pneumoniae 24 PBP2B Streptococcus pneumoniae 0.111 ug.mL-1
Displacement of Biocillin FL from Streptococcus pneumoniae 3413 PBP2B Streptococcus pneumoniae 0.178 ug.mL-1
Displacement of Biocillin FL from Streptococcus pneumoniae 2527 PBP2B Streptococcus pneumoniae 0.096 ug.mL-1
Displacement of Biocillin FL from Streptococcus pneumoniae 3676 PBP2B Streptococcus pneumoniae 0.264 ug.mL-1
Displacement of Biocillin FL from Streptococcus pneumoniae 3243 PBP2B Streptococcus pneumoniae 0.061 ug.mL-1
Displacement of Biocillin FL from Streptococcus pneumoniae 3665 PBP2B Streptococcus pneumoniae 0.156 ug.mL-1
Displacement of Biocillin FL from Streptococcus pneumoniae 3009 PBP2B Streptococcus pneumoniae 0.007 ug.mL-1
Displacement of Biocillin FL from Streptococcus pneumoniae 1076 PBP2B Streptococcus pneumoniae 0.06 ug.mL-1
Displacement of Biocillin FL from Streptococcus pneumoniae 1077 PBP2B Streptococcus pneumoniae 0.037 ug.mL-1
Displacement of Biocillin FL from Streptococcus pneumoniae 24 PBP3 Streptococcus pneumoniae 0.004 ug.mL-1
Displacement of Biocillin FL from Streptococcus pneumoniae 3413 PBP3 Streptococcus pneumoniae 0.01 ug.mL-1
Displacement of Biocillin FL from Streptococcus pneumoniae 2527 PBP3 Streptococcus pneumoniae 0.014 ug.mL-1
Displacement of Biocillin FL from Streptococcus pneumoniae 3676 PBP3 Streptococcus pneumoniae 0.007 ug.mL-1
Displacement of Biocillin FL from Streptococcus pneumoniae 3243 PBP3 Streptococcus pneumoniae 0.007 ug.mL-1
Displacement of Biocillin FL from Streptococcus pneumoniae 3665 PBP3 Streptococcus pneumoniae 0.01 ug.mL-1
Displacement of Biocillin FL from Streptococcus pneumoniae 3009 PBP3 Streptococcus pneumoniae 0.001 ug.mL-1
Displacement of Biocillin FL from Streptococcus pneumoniae 1076 PBP3 Streptococcus pneumoniae 0.016 ug.mL-1
Displacement of Biocillin FL from Streptococcus pneumoniae 1077 PBP3 Streptococcus pneumoniae 0.01 ug.mL-1
Inhibition of Escherichia coli MC4100 Beta-Lactamase CMY-30 using cephalothin as reporter substrate Escherichia coli 600.0 nM
Inhibition of Bocillin FL binding to Streptococcus pneumoniae isolate 8865 PBP2b Streptococcus pneumoniae 0.008 ug.mL-1
Inhibition of Streptococcus pneumoniae isolate 8882 Bocillin FL binding to PBP2b 443SSNA mutant Streptococcus pneumoniae 2.5 ug.mL-1
Inhibition of Bocillin FL binding to PBP2b PBP2b 443SSNA mutant in Streptococcus pneumoniae isolate 8009 harboring E333G, N470K, E476G, T489S, E506D, and N538D mutant genes Streptococcus pneumoniae 2.5 ug.mL-1
Inhibition of Bocillin FL binding to PBP2b in Streptococcus pneumoniae isolate 8819 harboring E333G, I361L, E369D, S412P, N422Y, T426K, Q427L, Q438E, L455I, S473T, E476G, S480A, T489A, N538D, D561E, Q564K, and D625G mutant genes Streptococcus pneumoniae 8.0 ug.mL-1
Inhibition of Bocillin FL binding to PBP2b in laboratory-derived Streptococcus pneumoniae isolate R6 Streptococcus pneumoniae 0.15 ug.mL-1
Inhibition of Bocillin FL binding to PBP2b Thr446Ala mutant in laboratory-derived Streptococcus pneumoniae isolate R6 Streptococcus pneumoniae 0.8 ug.mL-1
Inhibition of Bocillin FL binding to PBP2b Thr446Ala/Ala-619-Gly mutant in laboratory-derived Streptococcus pneumoniae isolate R6 Streptococcus pneumoniae 1.8 ug.mL-1
Inhibition of human liver OATP1B1 expressed in HEK293 Flp-In cells assessed as reduction in E17-betaG uptake at 20 uM by scintillation counting Homo sapiens 8.8 %
Inhibition of human liver OATP1B3 expressed in HEK293 Flp-In cells assessed as reduction in [3H]E17-betaG uptake at 20 uM incubated for 5 mins by scintillation counting Homo sapiens 40.9 %
Inhibition of human liver OATP2B1 expressed in HEK293 Flp-In cells assessed as reduction in [3H]E3S uptake at 20 uM incubated for 5 mins by scintillation counting Homo sapiens 7.6 %
Binding affinity to Staphylococcus aureus ATCC 43300 50S ribosome assessed as dissociation constant by SPR analysis Staphylococcus aureus 5.2 10^-1/s

Cross References

Resources Reference
ChEBI 18208
ChEMBL CHEMBL29
DrugBank DB01053
DrugCentral 2082
FDA SRS Q42T66VG0C
Human Metabolome Database HMDB0015186
Guide to Pharmacology 4796
KEGG C05551
PDB PNN
PharmGKB PA450842
SureChEMBL SCHEMBL3783
ZINC ZINC000003871701
CONTENTS