Penicillin G (CED0001397)

Record Information
Version1.0
Creation Date2016-05-25 18:24:36 UTC
Update Date2026-08-19 16:01:46 UTC
Accession NumberCHEM022223
Identification
Common NamePenicillin G
ClassSmall Molecule
Description
Penicillin G (C16H18N2O4S) is a compound with an average molecular weight of 334.39 g/mol. Penicillin G belongs to the amino acids, peptides, and analogues, a subclass of carboxylic acids and derivatives within the organic compounds. It is recorded as being found in or released from 28 sources, including drinking water, healthcare, pharmaceuticals and veterinary products such as antibiotics, antiinfectives, and penicillins, and food, food processing and cookware involving food preservation, fermentation processes for beer, and the preparation of vinegar, wine or sparkling wine. Other sources include household cleaning and consumer products such as soap detergents, perfumes within detergents and soaps, cigar cigarettes, other smoking requisites, and non electric simulated smoking devices, as well as electrical and electronic equipment including electric switches, electric hearing aids, discharge lamps, conductors or conductive bodies characterised by the conductive materials, and coils. The compound is associated with several recorded exposure routes, including oral, topical, intravenous, intrathecal, intrapleural, intramuscular, and inhalation. Penicillin G interacts with eight recorded protein targets. It acts as a binder, inhibitor, or inhibitor and serves as a substrate of Penicillin-binding protein 3 (pbp3), Organic anion transporter 3 (SLC22A8), Solute carrier family 15 member 1 (SLC15A1), Solute carrier family 15 member 2 (SLC15A2), and four other proteins.
Contaminant TypeNot Available
Chemical Structure
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
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Organoleptic EffectsNot 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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrumsplash10-0006-9111000000-c26265c0b3a7beb3ec2bNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS Spectrumsplash10-006x-9010000000-bdb726ea699de6cfed1cNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00di-9000000000-ea40b52a677fe59a6de1Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00di-9000000000-6b0ced613495ec7786cdNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0006-9200000000-fa9a998d05d785d35da3Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-03fr-0905000000-c9ebf3278702ed3da9aeNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-03fr-1900000000-cd0eb273a5bf00dd85b5Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-03fr-0905000000-45176c1f74d7cbe0cfa4Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-03fr-1901000000-1ba3d8bff84b3c6fb96aNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-01ox-9500000000-f670b692d530e470875aNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00di-9300000000-fdbd4edd10aa9a29a4f3Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0006-2900000000-e8940b6589f2b95e3403Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0400-2932000000-92082dd94f7c14c5ee1dNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0900-4920000000-957ebfd788454d96fea6Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0btc-9400000000-b7dc0535d63c2db40535Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0006-0920000000-d47e30dbb9656c5046b7Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0006-0930000000-1e3178016f1241e6e74eNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-002f-9600000000-c161010ceaa25b82e55eNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-000i-0229000000-8e49abf86f7c84100d01Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0hfx-3952000000-dd2b2b12cee1c489c1c2Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0006-8900000000-56c739c89af830c4b25bNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-001i-0019000000-847ef8ad73cfc8da19b4Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a4l-9702000000-9fa2f54365ec6ff4b041Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0006-9100000000-5dea18185be80fe32e19Not AvailableView Spectrum
Toxicity Profile
Mechanism of ToxicityNot Available
Carcinogenicity (IARC Classification)Not Available
Minimum Risk LevelNot Available
SymptomsNot Available
TreatmentNot Available
Toxicity Values
Toxicity ValueUnitValue RangeOrganismDose DescriptorRoute of ExposurePredicted or ExperimentalReference
6892.0Log mg/kg[3900:12000]RatLD50oralpredictedNot Available
Health Effects
Health EffectRelationshipDirectionReference
Exposure Sources
Source IDSourceSectorReference
10InsecticidesAgriculture & land managementNot Available
115Drinking waterDrinking water & water supplyNot Available
233BrushesPersonal care & cosmeticsNot Available
306AntibioticsHealthcare, pharmaceuticals & veterinary productsNot Available
340PenicillinsHealthcare, pharmaceuticals & veterinary productsNot Available
395AntiinfectivesHealthcare, pharmaceuticals & veterinary productsNot Available
508CoilsElectrical & Electronic EquipmentNot Available
511Conductors Or Conductive Bodies Characterised By The Conductive MaterialsElectrical & Electronic EquipmentNot Available
514Discharge LampsElectrical & Electronic EquipmentNot Available
516Electric Hearing AidsElectrical & Electronic EquipmentNot Available
517Electric SwitchesElectrical & Electronic EquipmentNot Available
518Electrically Stimulated Smoking DevicesElectrical & Electronic EquipmentNot Available
519ElectrodesElectrical & Electronic EquipmentNot Available
524Hybrid CapacitorsElectrical & Electronic EquipmentNot Available
525Line Transmission SystemsElectrical & Electronic EquipmentNot Available
532SelectorsElectrical & Electronic EquipmentNot Available
537Television SystemsElectrical & Electronic EquipmentNot Available
539Video GamesElectrical & Electronic EquipmentNot Available
541Agglomerated Sugar ProductsFood, food processing & cookwareNot Available
544Fermentation Processes For BeerFood, food processing & cookwareNot Available
545Food PreservationFood, food processing & cookwareNot Available
548Preparation Of VinegarFood, food processing & cookwareNot Available
549Preparation Of Wine Or Sparkling WineFood, food processing & cookwareNot Available
552Processing MeatsFood, food processing & cookwareNot Available
556Cigar CigarettesHousehold cleaning & consumer productsNot Available
559Non Electric Simulated Smoking DevicesHousehold cleaning & consumer productsNot Available
560Other Smoking RequisitesHousehold cleaning & consumer productsNot Available
561Perfumes Within Detergents And SoapsHousehold cleaning & consumer productsNot Available
563Soap DetergentsHousehold cleaning & consumer productsNot Available
569Tobacco Smoke FiltersHousehold cleaning & consumer productsNot Available
580Manufacture Preparation Of Tobacco ProductsIndustrial manufacturing & chemical processingNot Available
581Paper Making MachinesIndustrial manufacturing & chemical processingNot Available
583Anchoring EquipmentMarine, shipping & aquacultureNot Available
596AcaricidesAgriculture & land managementNot Available
600Herbicides And AlgicidesAgriculture & land managementNot Available
603NematocidesAgriculture & land managementNot Available
604Pest AttractantsAgriculture & land managementNot Available
605Pest RepellantsAgriculture & land managementNot Available
606Plant Growth RegulatorsAgriculture & land managementNot Available
610Aftersun ProductsPersonal care & cosmeticsNot Available
611Anti Perspirants Or Body DeoderantsPersonal care & cosmeticsNot Available
613DepilatoriesPersonal care & cosmeticsNot Available
614Essential Oils Or PerfumesPersonal care & cosmeticsNot Available
615Eye Makeup ProductsPersonal care & cosmeticsNot Available
617Lip Care ProductsPersonal care & cosmeticsNot Available
618Lip Makeup ProductsPersonal care & cosmeticsNot Available
630ToysRecreation & sports surfacesNot Available
632ApparelTextiles, leather & furnishingsNot Available
640Embroidering And TuftingTextiles, leather & furnishingsNot Available
642FootwearTextiles, leather & furnishingsNot Available
643HeadwearTextiles, leather & furnishingsNot Available
647Multicolour DyeingTextiles, leather & furnishingsNot Available
650Purses Luggage Hand BagsTextiles, leather & furnishingsNot Available
655Slide FastenersTextiles, leather & furnishingsNot Available
657Surface Finishing Of LeatherTextiles, leather & furnishingsNot Available
662Yarns Or ThreadsTextiles, leather & furnishingsNot Available
Pathways
1 pathway
Targets
StructureProteinUniProt IDOrganismRelationshipDetails
Click to view 3D structureStreptokinase AP10520Streptococcus pyogenes serotype M1Predicted (SEA)5.83869
Bile salt export pump structureClick to view 3D structureBile salt export pumpO95342HumansPredicted (SEA)6.46149
Click to view 3D structureBeta-lactamase ACC-4A4ZYU9Escherichia coliPredicted (SEA)0.0778492
Beta-lactamase structureClick to view 3D structureBeta-lactamaseP00811Escherichia coli (strain K12)Predicted (SEA)2.17978
Click to view 3D structureEfflux transporterQ3S5C3Salmonella newportPredicted (SEA)0.233548
Click to view 3D structureClass C beta-lactamase CMY-36Q48435Klebsiella pneumoniaePredicted (SEA)0.233548
Click to view 3D structureTranscriptional activator protein LuxRP12746Aliivibrio fischeriPredicted (SEA)2.25763
Click to view 3D structureTranscriptional activator protein LuxRP35327Vibrio fischeri (strain ATCC 700601 / ES114)Predicted (SEA)2.41333
Click to view 3D structureNeprilysinP07861Rattus norvegicusPredicted (SEA)120.355
Click to view 3D structureExtended-spectrum beta-lactamase PER-6D5HSX5Aeromonas allosaccharophilaPredicted (SEA)0.856341
Click to view 3D structureADC-14 proteinQ0VTR6Acinetobacter genomosp. 3Predicted (SEA)0.856341
Click to view 3D structureBeta-lactamase SHV-11Q7X575Escherichia coliPredicted (SEA)0.856341
Click to view 3D structureADC-16 proteinQ0VTR8Acinetobacter genomosp. 3Predicted (SEA)0.856341
Click to view 3D structureGlutaminase kidney isoform, mitochondrialP13264Rattus norvegicusPredicted (SEA)15.5698
Protein deacetylase HDAC6 structureClick to view 3D structureProtein deacetylase HDAC6Q9UBN7HumansPredicted (SEA)815.081
Beta-lactamase TEM structureClick to view 3D structureBeta-lactamase TEMP62593Escherichia coliPredicted (SEA)1.55698
Click to view 3D structureAngiotensin-converting enzymeP12822Oryctolagus cuniculusPredicted (SEA)106.342
Angiotensin-converting enzyme structureClick to view 3D structureAngiotensin-converting enzymeP12821HumansPredicted (SEA)233.703
Speckle-type POZ protein structureClick to view 3D structureSpeckle-type POZ proteinO43791HumansPredicted (SEA)1.40129
Mu-type opioid receptor structureClick to view 3D structureMu-type opioid receptorP35372HumansPredicted (SEA)887.325
Cathepsin D structureClick to view 3D structureCathepsin DP07339HumansPredicted (SEA)203.809
Click to view 3D structurePER-2 beta-lactamaseA2RP81Citrobacter freundiiPredicted (SEA)0.233548
Click to view 3D structureAspartic protease PM4O60989Plasmodium vivaxPredicted (SEA)5.3716
Click to view 3D structureSolute carrier family 22 member 6Q4U2R8HumansPredicted (SEA)6.30579
Click to view 3D structureOrganic anion transporter 3Q8TCC7HumansPredicted (SEA)4.20386
Concentrations
Not Available
External Links
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