Penicillin G (CHEM022223)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 18:24:36 UTC
Update Date2016-11-09 01:17:27 UTC
Accession NumberCHEM022223
Identification
Common NamePenicillin G
ClassSmall Molecule
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.
Contaminant Sources
  • HMDB Contaminants - Urine
  • STOFF IDENT Compounds
Contaminant TypeNot Available
Chemical 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 Mass334.390 g/mol
Monoisotopic Mass334.099 g/mol
CAS Registry Number61-33-6
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
SMILES[H][C@]12SC(C)(C)[C@@H](N1C(=O)[C@H]2NC(=O)CC1=CC=CC=C1)C(O)=O
InChI IdentifierInChI=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
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.28 g/LALOGPS
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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9111000000-c26265c0b3a7beb3ec2bSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-006x-9010000000-bdb726ea699de6cfed1cSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - 30V, Negativesplash10-00di-9000000000-ea40b52a677fe59a6de1Spectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-00di-9000000000-6b0ced613495ec7786cdSpectrum
LC-MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-0006-9200000000-fa9a998d05d785d35da3Spectrum
LC-MS/MSLC-MS/MS Spectrum - 0V, Positivesplash10-03fr-0905000000-c9ebf3278702ed3da9aeSpectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-03fr-1900000000-cd0eb273a5bf00dd85b5Spectrum
LC-MS/MSLC-MS/MS Spectrum - 0V, Positivesplash10-03fr-0905000000-45176c1f74d7cbe0cfa4Spectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-03fr-1901000000-1ba3d8bff84b3c6fb96aSpectrum
LC-MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-01ox-9500000000-f670b692d530e470875aSpectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-00di-9300000000-fdbd4edd10aa9a29a4f3Spectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-0006-2900000000-e8940b6589f2b95e3403Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0400-2932000000-92082dd94f7c14c5ee1dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0900-4920000000-957ebfd788454d96fea6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0btc-9400000000-b7dc0535d63c2db40535Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0920000000-d47e30dbb9656c5046b7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-0930000000-1e3178016f1241e6e74eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-002f-9600000000-c161010ceaa25b82e55eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0229000000-8e49abf86f7c84100d01Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0hfx-3952000000-dd2b2b12cee1c489c1c2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-8900000000-56c739c89af830c4b25bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0019000000-847ef8ad73cfc8da19b4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4l-9702000000-9fa2f54365ec6ff4b041Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9100000000-5dea18185be80fe32e19Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDDB01053
HMDB IDHMDB0015186
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDPNN
Wikipedia LinkBenzylpenicillin
Chemspider ID5693
ChEBI ID18208
PubChem Compound ID5904
Kegg Compound IDC05551
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. 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
2. Eagle H, Newman E, Musselman AD, Robinson M, Birmingham M: THE RENAL CLEARANCE OF PENICILLINS F, G, K, AND X IN RABBITS AND MAN. J Clin Invest. 1947 Sep;26(5):903-18.
3. Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043.
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=10930630
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=11431418
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=11906332
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=12569987
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=12850488
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=1384868
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=16033609
11. https://www.ncbi.nlm.nih.gov/pubmed/?term=1709917
12. https://www.ncbi.nlm.nih.gov/pubmed/?term=2083978
13. https://www.ncbi.nlm.nih.gov/pubmed/?term=24485692
14. https://www.ncbi.nlm.nih.gov/pubmed/?term=24631718
15. https://www.ncbi.nlm.nih.gov/pubmed/?term=25998949
16. https://www.ncbi.nlm.nih.gov/pubmed/?term=27731424
17. https://www.ncbi.nlm.nih.gov/pubmed/?term=29017833
18. https://www.ncbi.nlm.nih.gov/pubmed/?term=29355985
19. https://www.ncbi.nlm.nih.gov/pubmed/?term=6161899
20. https://www.ncbi.nlm.nih.gov/pubmed/?term=7602118
21. https://www.ncbi.nlm.nih.gov/pubmed/?term=7716788