Penicillin V (CHEM022107)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 18:20:23 UTC
Update Date2016-11-09 01:17:25 UTC
Accession NumberCHEM022107
Identification
Common NamePenicillin V
ClassSmall Molecule
DescriptionA penicillin compound having a 6beta-(phenoxyacetyl)amino side-chain.
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-(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
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 Solubility0.45 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
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, Positivesplash10-0006-9322000000-4de191c98a42f568cb80Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00dl-9120000000-a1d43b6f7b36c99253c8Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0291000000-38115fcb2144512aafd8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4l-4391000000-14c84175bfebc1ce80feSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9210000000-f2936b57e120f47f39dcSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-1109000000-319f4d6a2a700a6ed3b9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4m-9512000000-0f48145338e3fec3b861Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-a450a07a0a44f54cace0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03dl-2923000000-d226fb5017278afb5e95Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03dl-3910000000-48ee65139c72804d81c8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9500000000-90eba449715f7273e81aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0109000000-3f8cdfcceea1602d0a07Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0w2c-1933000000-090201c465f23ad0611aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004i-8901000000-04830724f7ecfdc9d13fSpectrum
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 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.