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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2013-06-15 18:04:04 UTC
Update Date2017-10-23 19:15:45 UTC
HMDB IDHMDB0060617
Secondary Accession Numbers
  • HMDB60617
Metabolite Identification
Common NamePenicilloic acid
DescriptionPenicilloic acid is a metabolite of penicillin v; penicillin g.
Structure
Thumb
Synonyms
ValueSource
Benzylpenicilloic acid, sodium salt, (2R-(2alpha(r*),4beta))-isomerMeSH
PenicilloateMeSH
Benzylpenicilloic acid, disodium salt, (2R-(2alpha(r*),4beta))-isomerMeSH
Benzylpenicilloic acid, monosodium saltMeSH
Benzylpenicilloic acidMeSH
Penicilloic acid, disodium saltMeSH
Chemical FormulaC16H20N2O5S
Average Molecular Weight352.405
Monoisotopic Molecular Weight352.10929245
IUPAC Name2-[carboxy(2-phenylacetamido)methyl]-5,5-dimethyl-1,3-thiazolidine-4-carboxylic acid
Traditional Name2-[carboxy(2-phenylacetamido)methyl]-5,5-dimethyl-1,3-thiazolidine-4-carboxylic acid
CAS Registry NumberNot Available
SMILES
CC1(C)SC(NC1C(O)=O)C(NC(=O)CC1=CC=CC=C1)C(O)=O
InChI Identifier
InChI=1S/C16H20N2O5S/c1-16(2)12(15(22)23)18-13(24-16)11(14(20)21)17-10(19)8-9-6-4-3-5-7-9/h3-7,11-13,18H,8H2,1-2H3,(H,17,19)(H,20,21)(H,22,23)
InChI KeyHCYWNSXLUZRKJX-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as n-acyl-alpha amino acids. These are compounds containing an alpha amino acid which bears an acyl group at its terminal nitrogen atom.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganic acids and derivatives
Sub ClassCarboxylic acids and derivatives
Direct ParentN-acyl-alpha amino acids
Alternative Parents
Substituents
  • N-acyl-alpha-amino acid
  • Phenylacetamide
  • Monocyclic benzene moiety
  • Dicarboxylic acid or derivatives
  • Benzenoid
  • Thiazolidine
  • Carboxamide group
  • Secondary carboxylic acid amide
  • Carboxylic acid
  • Azacycle
  • Thioether
  • Hemithioaminal
  • Organoheterocyclic compound
  • Dialkylthioether
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organic nitrogen compound
  • Carbonyl group
  • Organic oxygen compound
  • Organopnictogen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Biological Location:

  Subcellular:

  Biofluid and excreta:

  Organ and components:

Source:

Role

Biological role:

Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.28 g/LALOGPS
logP0.17ALOGPS
logP-1.2ChemAxon
logS-3.1ALOGPS
pKa (Strongest Acidic)2.69ChemAxon
pKa (Strongest Basic)6.64ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area115.73 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity87.61 m³·mol⁻¹ChemAxon
Polarizability34.93 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00kf-9312000000-434623c8ce300881debcView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-0006-9101200000-0c83da608573f9226cd7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0hg9-1529000000-7258ee31dd9c1cbe8e01View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014l-7963000000-b636594c20d9f5b4f688View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03dl-9800000000-c89744bb28b5928a33b7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-01t9-0094000000-5daea6a8cd048d997892View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-07f0-2296000000-453468cc5815535203daView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014i-9800000000-859731dfabdf627eebdbView in MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Kidney
  • Liver
PathwaysNot Available
NameSMPDB/PathwhizKEGG
No entries found
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot AvailableNormal
    details
    UrineExpected but not Quantified Not AvailableNot AvailableNormal
      details
      Abnormal Concentrations
      Not Available
      Associated Disorders and Diseases
      Disease ReferencesNone
      Associated OMIM IDsNone
      DrugBank IDNot Available
      DrugBank Metabolite IDDBMET00983
      Phenol Explorer Compound IDNot Available
      Phenol Explorer Metabolite IDNot Available
      FoodDB IDNot Available
      KNApSAcK IDNot Available
      Chemspider IDNot Available
      KEGG Compound IDNot Available
      BioCyc IDNot Available
      BiGG IDNot Available
      Wikipedia LinkNot Available
      METLIN IDNot Available
      PubChem CompoundNot Available
      PDB IDNot Available
      ChEBI IDNot Available
      References
      Synthesis ReferenceNot Available
      Material Safety Data Sheet (MSDS)Not Available
      General ReferencesNot Available