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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2013-06-15 18:06:03 UTC
Update Date2017-10-23 19:15:45 UTC
HMDB IDHMDB0060618
Secondary Accession Numbers
  • HMDB60618
Metabolite Identification
Common Name6-Aminopenicillanic acid
Description6-Aminopenicillanic acid is a metabolite of penicillin v; penicillin g.
Structure
Thumb
Synonyms
ValueSource
(+)-6-Aminopenicillanic acidChEBI
(2S,5R,6R)-6-amino-3,3-Dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acidChEBI
6-Aminopenicillamine acidChEBI
6-AminopenicillanateChEBI
6-APAChEBI
6-ApsChEBI
6beta-Aminopenicillanic acidChEBI
Aminopenicillanic acidChEBI
PenicinChEBI
PeninChEBI
Phenacyl 6-aminopenicillinateChEBI
(+)-6-AminopenicillanateGenerator
(2S,5R,6R)-6-amino-3,3-Dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylateGenerator
6b-AminopenicillanateGenerator
6b-Aminopenicillanic acidGenerator
6beta-AminopenicillanateGenerator
6β-aminopenicillanateGenerator
6β-aminopenicillanic acidGenerator
AminopenicillanateGenerator
Phenacyl 6-aminopenicillinic acidGenerator
6-APA CPDMeSH
Aminopenicillanic acid, potassium saltMeSH
Aminopenicillanic acid, sodium saltMeSH
Chemical FormulaC8H12N2O3S
Average Molecular Weight216.257
Monoisotopic Molecular Weight216.05686295
IUPAC Name(2S,5R,6R)-6-amino-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
Traditional Namepenin
CAS Registry NumberNot Available
SMILES
CC1(C)S[C@@H]2[C@H](N)C(=O)N2[C@H]1C(O)=O
InChI Identifier
InChI=1S/C8H12N2O3S/c1-8(2)4(7(12)13)10-5(11)3(9)6(10)14-8/h3-4,6H,9H2,1-2H3,(H,12,13)/t3-,4+,6-/m1/s1
InChI KeyNGHVIOIJCVXTGV-ALEPSDHESA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as dipeptides. These are organic compounds containing a sequence of exactly two alpha-amino acids joined by a peptide bond.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganic acids and derivatives
Sub ClassCarboxylic acids and derivatives
Direct ParentDipeptides
Alternative Parents
Substituents
  • Alpha-dipeptide
  • Alpha-amino acid or derivatives
  • Penam
  • Beta-lactam
  • Tertiary carboxylic acid amide
  • Thiazolidine
  • Amino acid or derivatives
  • Azetidine
  • Amino acid
  • Carboxamide group
  • Lactam
  • Carboxylic acid
  • Azacycle
  • Monocarboxylic acid or derivatives
  • Organoheterocyclic compound
  • Dialkylthioether
  • Hemithioaminal
  • Thioether
  • Amine
  • Primary aliphatic amine
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Organooxygen compound
  • Organic oxygen compound
  • Primary amine
  • Organopnictogen compound
  • Organic oxide
  • Carbonyl group
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External Descriptors
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 Solubility55.5 g/LALOGPS
logP-0.24ALOGPS
logP-2.8ChemAxon
logS-0.59ALOGPS
pKa (Strongest Acidic)3.42ChemAxon
pKa (Strongest Basic)7.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area83.63 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity50.36 m³·mol⁻¹ChemAxon
Polarizability20.7 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0uxr-1930000000-8b3dad9f5db3d8512110View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0uxr-1930000000-14be07ea22813265cdf3View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-9200000000-e33fe5dc6f7515fb41d5View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-05fr-9220000000-0d97e3938474120b9e87View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-00di-9300000000-e9bd620d9e681c167ae5View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-00di-9300000000-d0d73fa955283a4de8e1View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-00dr-0900000000-c0222f314effc3d7ad8aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-00dr-0900000000-f17a9cc1b1e04e3b7e71View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-9330000000-0853f16f9d9fb3a3f86eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-1910000000-fbdab9a3772fcfd7c0c8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9200000000-6b276429012b5ee9844fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-9200000000-9ffda48df6b90d12f303View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0ab9-9200000000-f630fdfcda8c288572e2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00di-9200000000-e7d207177892f580f3c9View 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 IDDBMET00758
      Phenol Explorer Compound IDNot Available
      Phenol Explorer Metabolite IDNot Available
      FoodDB IDNot Available
      KNApSAcK IDNot Available
      Chemspider IDNot Available
      KEGG Compound IDC02954
      BioCyc ID6-AMINOPENICILLANATE
      BiGG IDNot Available
      Wikipedia Link6-APA
      METLIN IDNot Available
      PubChem Compound11082
      PDB IDNot Available
      ChEBI ID16705
      References
      Synthesis ReferenceNot Available
      Material Safety Data Sheet (MSDS)Not Available
      General References
      1. Shimizu T, Souma S, Nagakura N, Masuzawa T, Iwamoto Y, Yanagihara Y: Epitope analysis of aztreonam by antiaztreonam monoclonal antibodies and possible consequences in beta-lactams hypersensitivity. Int Arch Allergy Immunol. 1992;98(4):392-7. [PubMed:1384868 ]
      2. Zhao Y, Qiao H: Detection of specific IgE antibodies to major and minor antigenic determinants in sera of penicillin allergic patients. Chin Med J (Engl). 2003 Dec;116(12):1904-10. [PubMed:14687482 ]
      3. Harle DG, Baldo BA: Identification of penicillin allergenic determinants that bind IgE antibodies in the sera of subjects with penicillin allergy. Mol Immunol. 1990 Nov;27(11):1063-71. [PubMed:1701026 ]
      4. Ariza A, Barrionuevo E, Mayorga C, Montanez MI, Perez-Inestrosa E, Ruiz-Sanchez A, Rodriguez-Gueant RM, Fernandez TD, Gueant JL, Torres MJ, Blanca M: IgE to penicillins with different specificities can be identified by a multiepitope macromolecule: Bihaptenic penicillin structures and IgE specificities. J Immunol Methods. 2014 Apr;406:43-50. doi: 10.1016/j.jim.2014.03.001. Epub 2014 Mar 13. [PubMed:24631718 ]