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Record Information
Version3.6
Creation Date2013-06-15 18:06:03 UTC
Update Date2017-03-02 22:05:16 UTC
HMDB IDHMDB60618
Secondary Accession NumbersNone
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
StatusExpected but not Quantified
Origin
  • Drug metabolite
Biofunction
  • Waste products
ApplicationNot Available
Cellular locations
  • Cytoplasm
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 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count1ChemAxon
Refractivity50.36 m3·mol-1ChemAxon
Polarizability20.7 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
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, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
Biological Properties
Cellular Locations
  • Cytoplasm
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Kidney
  • Liver
PathwaysNot Available
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 IDNot Available
      BiGG IDNot Available
      Wikipedia LinkNot Available
      NuGOwiki LinkHMDB60618
      Metagene LinkHMDB60618
      METLIN IDNot Available
      PubChem Compound11082
      PDB IDNot Available
      ChEBI ID16705
      References
      Synthesis ReferenceNot Available
      Material Safety Data Sheet (MSDS)Not Available
      General ReferencesNot Available