Showing metabocard for Penicillin G (BMDB0063636)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2018-12-04 20:29:04 UTC
Update Date2020-06-04 20:42:28 UTC
BMDB IDBMDB0063636
Secondary Accession Numbers
  • BMDB63636
Metabolite Identification
Common NamePenicillin G
DescriptionPenicillin G is narrow spectrum antibiotic used to treat infections caused by susceptible bacteria. It is a natural penicillin antibiotic that is administered intravenously or intramuscularly due to poor oral absorption. Penicillin G may also be used in some cases as prophylaxis against susceptible organisms. Natural penicillins are considered the drugs of choice for several infections caused by susceptible gram positive aerobic organisms, such as Streptococcus pneumoniae, groups A, B, C and G streptococci, nonenterococcal group D streptococci, viridans group streptococci, and non-penicillinase producing staphylococcus. Aminoglycosides may be added for synergy against group B streptococcus (S. agalactiae), S. viridans, and Enterococcus faecalis. The natural penicillins may also be used as first or second line agents against susceptible gram positive aerobic bacilli such as Bacillus anthracis, Corynebacterium diphtheriae, and Erysipelothrix rhusiopathiae. Natural penicillins have limited activity against gram negative organisms; however, they may be used in some cases to treat infections caused by Neisseria meningitidis and Pasteurella. They are not generally used to treat anaerobic infections. Resistance patterns, susceptibility and treatment guidelines vary across regions.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(2S,5R,6R)-3,3-Dimethyl-7-oxo-6-(phenylacetamido)-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acidChEBI
6-(2-Phenylacetamido)penicillanic acidChEBI
BencilpenicilinaChEBI
BensylpenicillinChEBI
Benzyl benicillinChEBI
BenzylpenicillineChEBI
Benzylpenicillinic acidChEBI
BenzylpenicillinumChEBI
Free penicillin IIChEBI
PCGChEBI
PGChEBI
BenzylpenicillinKegg
(2S,5R,6R)-3,3-Dimethyl-7-oxo-6-(phenylacetamido)-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylateGenerator
6-(2-Phenylacetamido)penicillanateGenerator
BenzylpenicillinateGenerator
Antibioticos brand OF penicillin g sodiumHMDB
Britannia brand OF penicillin g sodiumHMDB
Or-penHMDB
PekaminHMDB
PenibiotHMDB
PfizerpenHMDB
SodipenHMDB
Van-pen-gHMDB
Benzylpenicillin potassiumHMDB
CEPA brand OF penicillin g sodiumHMDB
Grünenthal brand OF penicillin g potassiumHMDB
Jenapharm brand OF penicillin g sodiumHMDB
Llorente brand OF penicillin g sodiumHMDB
Medical brand OF penicillin g sodiumHMDB
Normon brand OF penicillin g sodiumHMDB
Penicillin grünenthalHMDB
Sodium penicillinHMDB
UrsopenHMDB
BenpenHMDB
ColiriocilinaHMDB
Ern brand OF penicillin g sodiumHMDB
Lakeside brand OF penicillin g sodiumHMDB
Medical brand OF penicillin g potassiumHMDB
Ortega brand OF penicillin g potassiumHMDB
Penicilina g llorenteHMDB
Penicillin g potassiumHMDB
PenilevelHMDB
PenirogerHMDB
Pfizer brand OF penicillin g potassiumHMDB
SodiopenHMDB
Sodium benzylpenicillinHMDB
UCB brand OF penicillin g sodiumHMDB
UnicilinaHMDB
Bioniche brand OF penicillin g sodiumHMDB
CSL Brand OF penicillin g sodiumHMDB
Clonmel brand OF penicillin g sodiumHMDB
CrystapenHMDB
ParcillinHMDB
Parmed brand OF penicillin g potassiumHMDB
PengesodHMDB
Penicillin g jenapharmHMDB
Penicillin g sodiumHMDB
Vangard brand OF penicillin g potassiumHMDB
Penicillin gChEBI
Chemical FormulaC16H18N2O4S
Average Molecular Weight334.39
Monoisotopic Molecular Weight334.098727764
IUPAC Name(2S,5R,6R)-3,3-dimethyl-7-oxo-6-(2-phenylacetamido)-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
Traditional Namepenicillin G
CAS Registry Number61-33-6
SMILES
[H][C@]12SC(C)(C)[C@@H](N1C(=O)[C@H]2NC(=O)CC1=CC=CC=C1)C(O)=O
InChI Identifier
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
InChI KeyJGSARLDLIJGVTE-MBNYWOFBSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as dipeptides. These are organic compounds containing a sequence of exactly two alpha-amino acids joined by a peptide bond.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentDipeptides
Alternative Parents
Substituents
  • Alpha-dipeptide
  • Penicillin
  • N-acyl-alpha amino acid or derivatives
  • Alpha-amino acid or derivatives
  • Phenylacetamide
  • Penam
  • Monocyclic benzene moiety
  • Benzenoid
  • Beta-lactam
  • Thiazolidine
  • Tertiary carboxylic acid amide
  • Azetidine
  • Carboxamide group
  • Lactam
  • Secondary carboxylic acid amide
  • Carboxylic acid
  • Azacycle
  • Monocarboxylic acid or derivatives
  • Organoheterocyclic compound
  • Dialkylthioether
  • Hemithioaminal
  • Thioether
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Organic oxide
  • Carbonyl group
  • Hydrocarbon derivative
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
StatusDetected and Quantified
Origin
  • Exogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cell membrane
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point214 - 217 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility2.85e-01 g/LNot Available
LogP1.5Not Available
Predicted Properties
PropertyValueSource
logP1.92ALOGPS
logP1.08ChemAxon
logS-3.1ALOGPS
pKa (Strongest Acidic)3.53ChemAxon
pKa (Strongest Basic)-2.6ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area86.71 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity84.53 m³·mol⁻¹ChemAxon
Polarizability33.54 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9111000000-c26265c0b3a7beb3ec2bView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-006x-9010000000-bdb726ea699de6cfed1cView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - 30V, Negativesplash10-00di-9000000000-ea40b52a677fe59a6de1View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-00di-9000000000-6b0ced613495ec7786cdView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-0006-9200000000-fa9a998d05d785d35da3View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 0V, Positivesplash10-03fr-0905000000-c9ebf3278702ed3da9aeView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-03fr-1900000000-cd0eb273a5bf00dd85b5View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 0V, Positivesplash10-03fr-0905000000-45176c1f74d7cbe0cfa4View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-03fr-1901000000-1ba3d8bff84b3c6fb96aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-01ox-9500000000-f670b692d530e470875aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-00di-9300000000-fdbd4edd10aa9a29a4f3View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-0006-2900000000-e8940b6589f2b95e3403View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0400-2932000000-92082dd94f7c14c5ee1dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0900-4920000000-957ebfd788454d96fea6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0btc-9400000000-b7dc0535d63c2db40535View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0920000000-d47e30dbb9656c5046b7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-0930000000-1e3178016f1241e6e74eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-002f-9600000000-c161010ceaa25b82e55eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0229000000-8e49abf86f7c84100d01View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0hfx-3952000000-dd2b2b12cee1c489c1c2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-8900000000-56c739c89af830c4b25bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0019000000-847ef8ad73cfc8da19b4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4l-9702000000-9fa2f54365ec6ff4b041View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9100000000-5dea18185be80fe32e19View in MoNA
Biological Properties
Cellular Locations
  • Cell membrane
  • Membrane
Biospecimen Locations
  • Milk
  • Placenta
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
MilkDetected and Quantified0.036 uMNot SpecifiedNot Specified
Normal
    • Nina Bilandžić, B...
 details
PlacentaExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
Abnormal Concentrations
Not Available
HMDB IDHMDB0015186
DrugBank IDDB01053
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID5693
KEGG Compound IDC05551
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkBenzylpenicillin
METLIN IDNot Available
PubChem Compound5904
PDB IDPNN
ChEBI ID18208
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Nina Bilandžić, Božica Solomun Kolanović, Ivana Varenina, Giampiero Scortichini, Loredana Annunziata, Matko Brstilo, Nevenka Rudan (2011). Nina Bilandžić, Božica Solomun Kolanović, Ivana Varenina, Giampiero Scortichini, Loredana Annunziata, Matko Brstilo, Nevenka Rudan. Veterinary drug residues determination in raw milk in Croatia. Food Control. Volume 22, Issue 12, December 2011, Pages 1941-1948. Food Control.