Penicillin V (CED0004809)

Record Information
Version1.0
Creation Date2016-05-25 18:20:23 UTC
Update Date2026-08-19 16:01:56 UTC
Accession NumberCHEM022107
Identification
Common NamePenicillin V
ClassSmall Molecule
Description
Penicillin V is an organic compound with the formula C16H18N2O5S and an average molecular weight of 350.39 g/mol. Penicillin V belongs to the amino acids, peptides, and analogues, a subclass of carboxylic acids and derivatives within the organic compounds. This compound is identified in 16 recorded sources across several categories. Within healthcare, pharmaceuticals, and veterinary products, it is associated with antibiotics and penicillins. It is found in food, food processing, and cookware contexts, including food preservation, processing meats, agglomerated sugar products, and fermentation processes for beer. In drinking water and water supply, it is recorded in drinking water. Additionally, it is found in electrical and electronic equipment, such as electric switches, hybrid capacitors, conductors or conductive bodies characterised by the conductive materials, and electrically stimulated smoking devices. It is also released from household cleaning and consumer products, including soap detergents, perfumes within detergents and soaps, other smoking requisites, non electric simulated smoking devices, and tobacco smoke filters. Recorded routes of exposure include oral, oropharyngeal, and inhalation. Penicillin V interacts with four recorded protein targets. It acts as an inhibitor or transporter of penicillin-binding protein 1A (pbpA) and solute carrier family 15 member 1 (SLC15A1). It also targets D-alanyl-D-alanine carboxypeptidase DacB (dacB) and MecA PBP2' (penicillin binding protein 2') (mecA).
Contaminant TypeNot Available
Chemical Structure
Synonyms
ValueSource
(2S,5R,6R)-3,3-DIMETHYL-7-oxo-6-(2-phenoxyacetamido)-4-thia-1- azabicyclo(3.2.0)heptane-2-carboxylIC ACIDChEBI
(2S,5R,6R)-3,3-Dimethyl-7-oxo-6-[(phenoxyacetyl)amino]-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acidChEBI
6-Phenoxyacetamidopenicillanic acidChEBI
FenospenChEBI
FenoximetilpenicilinaChEBI
OracillinChEBI
Penicillin phenoxymethylChEBI
PhenoxomethylpenicillinChEBI
Phenoxymethylenepenicillinic acidChEBI
PhenoxymethylpenicillineChEBI
PhenoxymethylpenicillinumChEBI
PVChEBI
V-CillinChEBI
PhenoxymethylpenicillinKegg
(2S,5R,6R)-3,3-DIMETHYL-7-oxo-6-(2-phenoxyacetamido)-4-thia-1- azabicyclo(3.2.0)heptane-2-carboxylateGenerator
(2S,5R,6R)-3,3-Dimethyl-7-oxo-6-[(phenoxyacetyl)amino]-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylateGenerator
6-PhenoxyacetamidopenicillanateGenerator
PhenoxymethylenepenicillinateGenerator
PCVHMDB
FenossimetilpenicillinaHMDB
Penicillin V potassiumHMDB
PhenoximethylpenicillinumHMDB
Phenoxymethyl penicillinHMDB
Phenoxymethylpenicillin potassiumHMDB
Phenoxymethylpenicillinic acidHMDB
Phenoxymethylpenicillinic acid potassium saltHMDB
Berromycin, penicillinHMDB
Penicillin, phenoxymethylHMDB
V Cillin KHMDB
VegacillinHMDB
BeromycinHMDB
V-Cillin KHMDB
VCillin KHMDB
ApocillinHMDB
Beromycin, penicillinHMDB
FenoxymethylpenicillinHMDB
Pen VKHMDB
Potassium, penicillin VHMDB
V Sodium, penicillinHMDB
BetapenHMDB
Penicillin beromycinHMDB
Penicillin berromycinHMDB
Penicillin V sodiumHMDB
Penicillin VKHMDB
Sodium, penicillin VHMDB
Penicillin VChEBI
Chemical FormulaC16H18N2O5S
Average Molecular Mass350.390 g/mol
Monoisotopic Mass350.094 g/mol
CAS Registry Number87-08-1
IUPAC Name(2S,5R,6R)-3,3-dimethyl-7-oxo-6-(2-phenoxyacetamido)-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
Traditional Namepenicillin V
SMILES[H][C@]12SC(C)(C)[C@@H](N1C(=O)[C@H]2NC(=O)COC1=CC=CC=C1)C(O)=O
InChI IdentifierInChI=1S/C16H18N2O5S/c1-16(2)12(15(21)22)18-13(20)11(14(18)24-16)17-10(19)8-23-9-6-4-3-5-7-9/h3-7,11-12,14H,8H2,1-2H3,(H,17,19)(H,21,22)/t11-,12+,14-/m1/s1
InChI KeyBPLBGHOLXOTWMN-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
  • Phenoxy compound
  • Phenol ether
  • Penam
  • Alkyl aryl ether
  • Monocyclic benzene moiety
  • Benzenoid
  • Beta-lactam
  • Tertiary carboxylic acid amide
  • Thiazolidine
  • Lactam
  • Carboxamide group
  • Secondary carboxylic acid amide
  • Azetidine
  • Azacycle
  • Carboxylic acid
  • Ether
  • Organoheterocyclic compound
  • Monocarboxylic acid or derivatives
  • Dialkylthioether
  • Hemithioaminal
  • Thioether
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Organooxygen compound
  • Carbonyl group
  • Organic nitrogen compound
  • 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 Solubility0.45 g/LALOGPS
logP1.78ALOGPS
logP0.76ChemAxon
logS-2.9ALOGPS
pKa (Strongest Acidic)3.39ChemAxon
pKa (Strongest Basic)-4.9ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area95.94 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity85.77 m³·mol⁻¹ChemAxon
Polarizability34.37 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 Spectrumsplash10-0006-9322000000-4de191c98a42f568cb80Not AvailableView Spectrum
Predicted GC-MSPredicted GC-MS Spectrumsplash10-00dl-9120000000-a1d43b6f7b36c99253c8Not AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-03dl-2923000000-d226fb5017278afb5e95Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-03dl-3910000000-48ee65139c72804d81c8Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a4i-9500000000-90eba449715f7273e81aNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a4i-0291000000-38115fcb2144512aafd8Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a4l-4391000000-14c84175bfebc1ce80feNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0006-9210000000-f2936b57e120f47f39dcNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0002-1109000000-319f4d6a2a700a6ed3b9Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a4m-9512000000-0f48145338e3fec3b861Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0006-9000000000-a450a07a0a44f54cace0Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0udi-0109000000-3f8cdfcceea1602d0a07Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0w2c-1933000000-090201c465f23ad0611aNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-004i-8901000000-04830724f7ecfdc9d13fNot 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
3271.0Log mg/kg[1800:5800]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
511Conductors Or Conductive Bodies Characterised By The Conductive MaterialsElectrical & Electronic EquipmentNot Available
517Electric SwitchesElectrical & Electronic EquipmentNot Available
518Electrically Stimulated Smoking DevicesElectrical & Electronic EquipmentNot Available
524Hybrid CapacitorsElectrical & Electronic EquipmentNot Available
541Agglomerated Sugar ProductsFood, food processing & cookwareNot Available
544Fermentation Processes For BeerFood, food processing & cookwareNot Available
545Food PreservationFood, food processing & cookwareNot Available
552Processing MeatsFood, food processing & cookwareNot 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
583Anchoring EquipmentMarine, shipping & aquacultureNot 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
617Lip Care ProductsPersonal care & cosmeticsNot Available
618Lip Makeup ProductsPersonal care & cosmeticsNot Available
632ApparelTextiles, leather & furnishingsNot Available
642FootwearTextiles, leather & furnishingsNot Available
Pathways
1 pathway
Targets
StructureProteinUniProt IDOrganismRelationshipDetails
Penicillin-binding protein 2x structureClick to view 3D structurePenicillin-binding protein 2xP14677Streptococcus pneumoniae serotype 4 (strain ATCC BAA-334 / TIGR4)Predicted (SEA)0.0778492
Click to view 3D structureStreptokinase AP10520Streptococcus pyogenes serotype M1Predicted (SEA)23.1991
Adiponectin receptor protein 2 structureClick to view 3D structureAdiponectin receptor protein 2Q86V24HumansPredicted (SEA)20.63
Adiponectin receptor protein 1 structureClick to view 3D structureAdiponectin receptor protein 1Q96A54HumansPredicted (SEA)20.63
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)2.41333
Speckle-type POZ protein structureClick to view 3D structureSpeckle-type POZ proteinO43791HumansPredicted (SEA)0.544945
Bile salt export pump structureClick to view 3D structureBile salt export pumpO95342HumansPredicted (SEA)26.0795
Click to view 3D structureEfflux transporterQ3S5C3Salmonella newportPredicted (SEA)0.233548
Click to view 3D structureClass C beta-lactamase CMY-36Q48435Klebsiella pneumoniaePredicted (SEA)0.233548
Beta-lactamase TEM structureClick to view 3D structureBeta-lactamase TEMP62593Escherichia coliPredicted (SEA)1.55698
Click to view 3D structureAspartic protease PM4O60989Plasmodium vivaxPredicted (SEA)5.3716
Cathepsin D structureClick to view 3D structureCathepsin DP07339HumansPredicted (SEA)193.455
Click to view 3D structurePlasmepsin IIIQ9Y006Plasmodium falciparumPredicted (SEA)6.77288
Cytochrome P450 3A4 structureClick to view 3D structureCytochrome P450 3A4P08684HumansPredicted (SEA)2541.08
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 structureAcetylcholinesteraseQ6A2E2Aedes aegyptiPredicted (SEA)51.3026
Tyrosine-protein phosphatase non-receptor type 11 structureClick to view 3D structureTyrosine-protein phosphatase non-receptor type 11Q06124HumansPredicted (SEA)131.332
Cytochrome P450 2D6 structureClick to view 3D structureCytochrome P450 2D6P10635HumansPredicted (SEA)2548.55
Plasmepsin II structureClick to view 3D structurePlasmepsin IIP46925Plasmodium falciparumPredicted (SEA)52.9375
Adenosine receptor A2b structureClick to view 3D structureAdenosine receptor A2bP29275HumansPredicted (SEA)370.718
Carboxy-terminal domain RNA polymerase II polypeptide A small phosphatase 1 structureClick to view 3D structureCarboxy-terminal domain RNA polymerase II polypeptide A small phosphatase 1Q9GZU7HumansPredicted (SEA)248.105
Concentrations
Not Available
External Links
DrugBank IDDB00417
HMDB IDHMDB0014561
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDPNV
Wikipedia LinkPhenoxymethylpenicillin
Chemspider ID6607
ChEBI ID27446
PubChem Compound ID6869
Kegg Compound IDC08126
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=10930630
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=12569987
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=13377278
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=14687482
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=16033609
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=19357666
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=19496253
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=21148688
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=22763423
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=23732051
11. https://www.ncbi.nlm.nih.gov/pubmed/?term=26986755
12. https://www.ncbi.nlm.nih.gov/pubmed/?term=27731424
13. https://www.ncbi.nlm.nih.gov/pubmed/?term=8566082
14. Authors unspecified: Inadvertent use of Bicillin C-R to treat syphilis infection--Los Angeles, California, 1999-2004. MMWR Morb Mortal Wkly Rep. 2005 Mar 11;54(9):217-9.
15. Gruchalla RS, Pirmohamed M: Clinical practice. Antibiotic allergy. N Engl J Med. 2006 Feb 9;354(6):601-9.