6-Aminopenicillanic acid (CED0008693)

Record Information
Version1.0
Creation Date2016-05-22 05:29:19 UTC
Update Date2026-03-31 20:17:07 UTC
Accession NumberCHEM018731
Identification
Common Name6-Aminopenicillanic acid
ClassSmall Molecule
Description
6-Aminopenicillanic acid (C8H12N2O3S) is an organic compound with an average molecular weight of 216.26 g/mol. 6-Aminopenicillanic acid belongs to the amino acids, peptides, and analogues, a subclass of carboxylic acids and derivatives within the organic compounds. This substance has been identified in or released from seven recorded sources. Within the healthcare, pharmaceuticals, and veterinary products sector, it is associated with antibiotics. It has also been recorded in relation to drinking water and water supply, specifically drinking water. Other recorded sources include electrical and electronic equipment, such as electrodes, antennas, and radio transmission systems, as well as building and construction materials, specifically stairs and ramps. Additionally, it is linked to food, food processing, and cookware through the preparation of vinegar. Recorded exposure routes for 6-aminopenicillanic acid include inhalation and oral ingestion.
Contaminant TypeNot Available
Chemical Structure
MOLSDF3D SDFPDBSMILESInChI View 3D Structure
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 CPDHMDB
Aminopenicillanic acid, potassium saltHMDB
Aminopenicillanic acid, sodium saltHMDB
Chemical FormulaC8H12N2O3S
Average Molecular Mass216.257 g/mol
Monoisotopic Mass216.057 g/mol
CAS Registry Number551-16-6
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
SMILESCC1(C)S[C@@H]2[C@H](N)C(=O)N2[C@H]1C(O)=O
InChI IdentifierInChI=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
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
  • 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
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Organoleptic EffectsNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot 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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
GC-MSGC-MS Spectrumsplash10-0uxr-1930000000-8b3dad9f5db3d8512110Not AvailableView Spectrum
GC-MSGC-MS Spectrumsplash10-0uxr-1930000000-14be07ea22813265cdf3Not AvailableView Spectrum
GC-MSGC-MS Spectrumsplash10-0uxr-1930000000-8b3dad9f5db3d8512110Not AvailableView Spectrum
GC-MSGC-MS Spectrumsplash10-0uxr-1930000000-14be07ea22813265cdf3Not AvailableView Spectrum
Predicted GC-MSPredicted GC-MS Spectrumsplash10-0a4i-9200000000-e33fe5dc6f7515fb41d5Not AvailableView Spectrum
Predicted GC-MSPredicted GC-MS Spectrumsplash10-05fr-9220000000-0d97e3938474120b9e87Not AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00di-9300000000-e9bd620d9e681c167ae5Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00di-9300000000-d0d73fa955283a4de8e1Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00dr-0900000000-c0222f314effc3d7ad8aNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00dr-0900000000-f17a9cc1b1e04e3b7e71Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a4i-9330000000-0853f16f9d9fb3a3f86eNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-03di-1910000000-fbdab9a3772fcfd7c0c8Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a4i-9200000000-6b276429012b5ee9844fNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00di-9200000000-9ffda48df6b90d12f303Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0ab9-9200000000-f630fdfcda8c288572e2Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00di-9200000000-e7d207177892f580f3c9Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00kr-0950000000-bbef363560f5d2d25c16Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-03di-1910000000-8a0d3e001608783c72a0Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-014i-9800000000-64b11c9f70ce0cb2d2b0Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00di-9100000000-25f442a83faa3f7da843Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00di-9200000000-7d7718220a18a63d2655Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00di-9000000000-766302f54e49d015548cNot AvailableView Spectrum
1D NMR13C NMR Spectrum (1D, D2O, predicted)Not AvailableNot AvailableView Spectrum
1D NMR1H NMR Spectrum (1D, D2O, predicted)Not AvailableNot AvailableView Spectrum
Toxicity Profile
Mechanism of ToxicityNot Available
Carcinogenicity (IARC Classification)Not Available
Minimum Risk LevelNot Available
SymptomsNot Available
TreatmentNot Available
Toxicity Values
Toxicity ValueUnitValue RangeOrganismDose DescriptorRoute of ExposurePredicted or ExperimentalReference
5813.0Log mg/kg[3300:10000]RatLD50oralpredictedNot Available
Health Effects
Health EffectRelationshipDirectionReference
Exposure Sources
Source IDSourceSectorReference
115Drinking waterDrinking water & water supplyNot Available
306AntibioticsHealthcare, pharmaceuticals & veterinary productsNot Available
500Stairs And RampsBuilding & ConstructionNot Available
506AntennasElectrical & Electronic EquipmentNot Available
519ElectrodesElectrical & Electronic EquipmentNot Available
530Radio Transmission SystemsElectrical & Electronic EquipmentNot Available
548Preparation Of VinegarFood, food processing & cookwareNot Available
581Paper Making MachinesIndustrial manufacturing & chemical processingNot Available
603NematocidesAgriculture & land managementNot Available
605Pest RepellantsAgriculture & land managementNot Available
Pathways
0 pathways

No pathways found

No metabolic pathways have been associated with this synthetic chemical

Targets
StructureProteinUniProt IDOrganismRelationshipDetails
Beta-lactamase structureClick to view 3D structureBeta-lactamaseP00811Escherichia coli (strain K12)Predicted (SEA)1.16774
Click to view 3D structureExtended-spectrum beta-lactamase PER-6D5HSX5Aeromonas allosaccharophilaPredicted (SEA)0.778492
Click to view 3D structureADC-14 proteinQ0VTR6Acinetobacter genomosp. 3Predicted (SEA)0.778492
Click to view 3D structureBeta-lactamase SHV-11Q7X575Escherichia coliPredicted (SEA)0.778492
Click to view 3D structureADC-16 proteinQ0VTR8Acinetobacter genomosp. 3Predicted (SEA)0.778492
Beta-lactamase TEM structureClick to view 3D structureBeta-lactamase TEMP62593Escherichia coliPredicted (SEA)1.47914
Click to view 3D structureMetallo-beta-lactamase type 2P14488Bacillus cereusPredicted (SEA)0.700643
Click to view 3D structureEfflux transporterQ3S5C3Salmonella newportPredicted (SEA)0.233548
Click to view 3D structureClass C beta-lactamase CMY-36Q48435Klebsiella pneumoniaePredicted (SEA)0.233548
Click to view 3D structureBeta-lactamase ACC-4A4ZYU9Escherichia coliPredicted (SEA)0.778492
Click to view 3D structureBeta-lactamase bla(BEL1)Q3SAW3Pseudomonas aeruginosaPredicted (SEA)0.856341
Click to view 3D structureBeta-lactamaseA8RR46Bacillus clausiiPredicted (SEA)0.856341
Click to view 3D structureBeta-lactamaseD2SSQ3Pseudomonas aeruginosaPredicted (SEA)0.856341
Click to view 3D structureBeta-lactamase SCO-1A1E3K9Escherichia coliPredicted (SEA)0.856341
Beta-lactamase structureClick to view 3D structureBeta-lactamaseP05364Enterobacter cloacaePredicted (SEA)2.64687
Click to view 3D structurePenB class A beta-lactamaseB8R6A5Burkholderia cenocepaciaPredicted (SEA)1.08989
Click to view 3D structureBeta-lactamaseP94958Morganella morganiiPredicted (SEA)1.08989
Click to view 3D structureCarbapenem-hydrolizing beta-lactamase SFC-1Q6JP75Serratia fonticolaPredicted (SEA)1.08989
Beta-lactamase structureClick to view 3D structureBeta-lactamaseP00808Bacillus licheniformisPredicted (SEA)0.856341
Beta-lactamase structureClick to view 3D structureBeta-lactamaseP05193Citrobacter freundiiPredicted (SEA)0.856341
Beta-lactamase structureClick to view 3D structureBeta-lactamaseP00807Staphylococcus aureusPredicted (SEA)1.71268
Click to view 3D structureBeta-lactamase GES-13D1MIX9Pseudomonas aeruginosaPredicted (SEA)0.856341
Click to view 3D structureStreptokinase AP10520Streptococcus pyogenes serotype M1Predicted (SEA)1997.84
Click to view 3D structureHemagglutininP03438Influenza A virus (strain A/X-31 H3N2)Predicted (SEA)5.44945
Click to view 3D structureBeta-lactamase SHV-1P0AD63Escherichia coliPredicted (SEA)1.55698
Concentrations
Not Available
External Links
DrugBank IDNot Available
HMDB IDHMDB0060618
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia Link6-APA
Chemspider IDNot Available
ChEBI ID16705
PubChem Compound ID11082
Kegg Compound IDC02954
YMDB IDNot Available
ECMDB IDM2MDB004314
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=12569987
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=1384868
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=14687482
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=1701026
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=20970923
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=21614893
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=24293403
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=24389703
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=24631718
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=25057428
11. https://www.ncbi.nlm.nih.gov/pubmed/?term=26852849
12. https://www.ncbi.nlm.nih.gov/pubmed/?term=26986755
13. https://www.ncbi.nlm.nih.gov/pubmed/?term=6166603
14. 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.
15. 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.
16. 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.
17. 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.