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Record Information
Version3.6
Creation Date2012-09-06 15:16:49 UTC
Update Date2016-02-11 01:28:59 UTC
HMDB IDHMDB14561
Secondary Accession NumbersNone
Metabolite Identification
Common NamePenicillin V
DescriptionPenicillin V is narrow spectrum antibiotic used to treat mild to moderate infections caused by susceptible bacteria. It is a natural penicillin antibiotic that is administered orally. Penicillin V 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
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
(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
FenossimetilpenicillinaHMDB
Penicillin V potassiumHMDB
PhenoximethylpenicillinumHMDB
Phenoxymethyl penicillinHMDB
Phenoxymethylpenicillin potassiumHMDB
Phenoxymethylpenicillinic acidHMDB
Phenoxymethylpenicillinic acid potassium saltHMDB
Chemical FormulaC16H18N2O5S
Average Molecular Weight350.39
Monoisotopic Molecular Weight350.093642386
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
CAS Registry Number87-08-1
SMILES
[H][C@]12SC(C)(C)[C@@H](N1C(=O)[C@H]2NC(=O)COC1=CC=CC=C1)C(O)=O
InChI Identifier
InChI=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 KeyInChIKey=BPLBGHOLXOTWMN-MBNYWOFBSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as penicillins. These are organic compounds containing the penicillin core structure, which is structurally characterized by a penam ring bearing two methyl groups at position 2, and an amide group at position 6 [starting from the sulfur atom at position 1].
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassLactams
Sub ClassBeta lactams
Direct ParentPenicillins
Alternative Parents
Substituents
  • Penicillin
  • N-acyl-alpha amino acid or derivatives
  • Alpha-amino acid or derivatives
  • Phenol ether
  • Alkyl aryl ether
  • Thiazolidine
  • Tertiary carboxylic acid amide
  • Tertiary amine
  • Secondary carboxylic acid amide
  • Carboxamide group
  • Azetidine
  • Azacycle
  • Dialkylthioether
  • Hemithioaminal
  • Thioether
  • Monocarboxylic acid or derivatives
  • Ether
  • Carboxylic acid
  • Carboxylic acid derivative
  • Carboxylic acid amide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Amine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
StatusExpected but not Quantified
Origin
  • Drug
Biofunction
  • Anti-Bacterial Agents
  • Penicillins
Application
  • Pharmaceutical
Cellular locations
  • Cytoplasm
  • Extracellular
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point120 - 128 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility4.54e-01 g/LNot Available
LogP1.4Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.45 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity85.77 m3·mol-1ChemAxon
Polarizability34.37 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biofluid Locations
  • Blood
  • Urine
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00417
  • Not Applicable
details
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00417
  • Not Applicable
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00417
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID6607
KEGG Compound IDC08126
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkPenicillin_V
NuGOwiki LinkHMDB14561
Metagene LinkHMDB14561
METLIN IDNot Available
PubChem Compound6869
PDB IDPNV
ChEBI ID27446
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. 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. [15758893 ]
  2. Gruchalla RS, Pirmohamed M: Clinical practice. Antibiotic allergy. N Engl J Med. 2006 Feb 9;354(6):601-9. [16467547 ]