Bacampicillin (CED0013283)

Record Information
Version1.0
Creation Date2016-05-25 18:28:03 UTC
Update Date2026-08-21 19:31:54 UTC
Accession NumberCHEM022318
Identification
Common NameBacampicillin
ClassSmall Molecule
Description
Bacampicillin is an organic compound with the chemical formula C21H27N3O7S and an average molecular weight of 465.52 g/mol. Bacampicillin belongs to the beta lactams, a subclass of lactams within the organic compounds. It is further classified as an organoheterocyclic compound. This substance is found in or released from two recorded sources: pharmaceuticals and veterinary products, specifically within the categories of antibiotics and penicillins. Recorded routes of exposure include oral and inhalation. In terms of biological activity, Bacampicillin interacts with seven recorded protein targets. It acts as an inhibitor of Penicillin-binding protein 1A (mrcA), Penicillin-binding protein 1B (mrcB), D-alanyl-D-alanine carboxypeptidase DacC (dacC), and Peptidoglycan D,D-transpeptidase MrdA (mrdA), as well as three other proteins.
Contaminant TypeNot Available
Chemical Structure
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
1'-Ethoxycarbonyloxyethyl-(6-D-alpha-aminophenylacetamido)penicillanateChEBI
1-[(Ethoxycarbonyl)oxy]ethyl (2S,5R,6R)-6-{[(2R)-2-amino-2-phenylacetyl]amino}-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylateChEBI
BacampicilinaChEBI
BacampicillineChEBI
BacampicillinumChEBI
PenglobeKegg
1'-Ethoxycarbonyloxyethyl-(6-D-a-aminophenylacetamido)penicillanateGenerator
1'-Ethoxycarbonyloxyethyl-(6-D-a-aminophenylacetamido)penicillanic acidGenerator
1'-Ethoxycarbonyloxyethyl-(6-D-alpha-aminophenylacetamido)penicillanic acidGenerator
1'-Ethoxycarbonyloxyethyl-(6-D-α-aminophenylacetamido)penicillanateGenerator
1'-Ethoxycarbonyloxyethyl-(6-D-α-aminophenylacetamido)penicillanic acidGenerator
1-[(Ethoxycarbonyl)oxy]ethyl (2S,5R,6R)-6-{[(2R)-2-amino-2-phenylacetyl]amino}-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acidGenerator
BAPCHMDB
Bacampicillin hydrochlorideHMDB
Bacampicillin monohydrochlorideHMDB
Ethoxycarbonyloxyethyl ester OF ampicillinHMDB
BacampicineHMDB
CarampicillinHMDB
Chemical FormulaC21H27N3O7S
Average Molecular Mass465.520 g/mol
Monoisotopic Mass465.157 g/mol
CAS Registry Number50972-17-3
IUPAC Name1-[(ethoxycarbonyl)oxy]ethyl (2S,5R,6R)-6-[(2R)-2-amino-2-phenylacetamido]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate
Traditional Namebacampicillin
SMILES[H][C@]12SC(C)(C)[C@@H](N1C(=O)[C@H]2NC(=O)[C@H](N)C1=CC=CC=C1)C(=O)OC(C)OC(=O)OCC
InChI IdentifierInChI=1S/C21H27N3O7S/c1-5-29-20(28)31-11(2)30-19(27)15-21(3,4)32-18-14(17(26)24(15)18)23-16(25)13(22)12-9-7-6-8-10-12/h6-11,13-15,18H,5,22H2,1-4H3,(H,23,25)/t11?,13-,14-,15+,18-/m1/s1
InChI KeyPFOLLRNADZZWEX-FFGRCDKISA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as penicillins. These are organic compounds containing the penicillin core structure, which is structurally characterized by a penam ring bearing two methyl groups at position 2, and an amide group at position 6 [starting from the sulfur atom at position 1].
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassLactams
Sub ClassBeta lactams
Direct ParentPenicillins
Alternative Parents
Substituents
  • Penicillin
  • Alpha-amino acid ester
  • N-acyl-alpha amino acid or derivatives
  • Alpha-amino acid amide
  • Alpha-amino acid or derivatives
  • Phenylacetamide
  • Aralkylamine
  • Monocyclic benzene moiety
  • Carbonic acid diester
  • Benzenoid
  • Thiazolidine
  • Tertiary carboxylic acid amide
  • Secondary carboxylic acid amide
  • Amino acid or derivatives
  • Azetidine
  • Carbonic acid derivative
  • Carboxamide group
  • Carboxylic acid ester
  • Hemithioaminal
  • Thioether
  • Dialkylthioether
  • Azacycle
  • Acetal
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Primary amine
  • Primary aliphatic amine
  • Carbonyl group
  • Organic nitrogen compound
  • Organic oxide
  • Organonitrogen compound
  • Organooxygen compound
  • Amine
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organic oxygen 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
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 Solubility0.12 g/LALOGPS
logP1.17ALOGPS
logP1.47ChemAxon
logS-3.6ALOGPS
pKa (Strongest Acidic)11.72ChemAxon
pKa (Strongest Basic)7.44ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area137.26 ŲChemAxon
Rotatable Bond Count10ChemAxon
Refractivity113.76 m³·mol⁻¹ChemAxon
Polarizability46.8 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrumsplash10-0a4i-1900000000-210a80ea99d7d8b19c7cNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-052f-5914100000-b2bb79f625d3a39bd072Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a4l-7911000000-c5d3cfc8023d3a8d1c16Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a4i-6910000000-bb9f92cfef936fcb5cabNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a4i-0391100000-56ef32146ff2caf816afNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a4i-8593000000-92004702bfb034e6fad9Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-056r-9510000000-079171b8e9ca83a521cbNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0aos-0417900000-e6199826945c6f15ce9fNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0adi-2639600000-ef04d08a127b82678b0bNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a4i-4910000000-ff0f3c2bb5b4f7c58350Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0079-9015000000-d06a5bb09c37d08d5b91Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-03dj-9310000000-e4b469c81aee8f9b372cNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0006-9120000000-b9b13300295f6383c378Not 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
5908.0Log mg/kg[3300:11000]RatLD50oralpredictedNot Available
Health Effects
Health EffectRelationshipDirectionReference
Exposure Sources
Source IDSourceSectorReference
306AntibioticsHealthcare, pharmaceuticals & veterinary productsNot Available
340PenicillinsHealthcare, pharmaceuticals & veterinary productsNot Available
Pathways
1 pathway
Bacampicillin Drug Metabolism Action Pathway
Bacampicillin Drug Metabolism Action Pathway
Targets
StructureProteinUniProt IDOrganismRelationshipDetails
Click to view 3D structureStreptokinase AP10520Streptococcus pyogenes serotype M1Predicted (SEA)159.046
Click to view 3D structureBeta-lactamase ACC-4A4ZYU9Escherichia coliPredicted (SEA)0.778492
Bile salt export pump structureClick to view 3D structureBile salt export pumpO95342HumansPredicted (SEA)180.065
Click to view 3D structureSolute carrier family 22 member 6Q4U2R8HumansPredicted (SEA)15.7255
Click to view 3D structureOrganic anion transporter 3Q8TCC7HumansPredicted (SEA)8.09632
Baculoviral IAP repeat-containing protein 8 structureClick to view 3D structureBaculoviral IAP repeat-containing protein 8Q96P09HumansPredicted (SEA)19.8516
Carboxy-terminal domain RNA polymerase II polypeptide A small phosphatase 1 structureClick to view 3D structureCarboxy-terminal domain RNA polymerase II polypeptide A small phosphatase 1Q9GZU7HumansPredicted (SEA)377.024
Baculoviral IAP repeat-containing protein 2 structureClick to view 3D structureBaculoviral IAP repeat-containing protein 2Q13490HumansPredicted (SEA)42.1943
Click to view 3D structureSodium-dependent serotonin transporterP31652Rattus norvegicusPredicted (SEA)951.318
E3 ubiquitin-protein ligase XIAP structureClick to view 3D structureE3 ubiquitin-protein ligase XIAPP98170HumansPredicted (SEA)120.355
Cathepsin K structureClick to view 3D structureCathepsin KP43235HumansPredicted (SEA)670.749
Solute carrier family 15 member 2 structureClick to view 3D structureSolute carrier family 15 member 2Q16348HumansPredicted (SEA)96.8444
Click to view 3D structurePalmitoyl-protein thioesterase ABHD10, mitochondrialQ6PE15Mus musculusPredicted (SEA)2.56902
Cytochrome P450 2C9 structureClick to view 3D structureCytochrome P450 2C9P11712HumansPredicted (SEA)5209.75
Click to view 3D structureEfflux transporterQ3S5C3Salmonella newportPredicted (SEA)0.856341
Click to view 3D structureClass C beta-lactamase CMY-36Q48435Klebsiella pneumoniaePredicted (SEA)0.856341
Click to view 3D structureSodium-dependent dopamine transporterP23977Rattus norvegicusPredicted (SEA)814.536
Mu-type opioid receptor structureClick to view 3D structureMu-type opioid receptorP35372HumansPredicted (SEA)2439.17
Cathepsin S structureClick to view 3D structureCathepsin SP25774HumansPredicted (SEA)819.13
Click to view 3D structureMu-type opioid receptorP97266Cavia porcellusPredicted (SEA)769.15
Pyruvate carboxylase structureClick to view 3D structurePyruvate carboxylaseA0A0H3JRU9Staphylococcus aureus (strain Mu50 / ATCC 700699)Predicted (SEA)39.0803
Cytochrome P450 2C19 structureClick to view 3D structureCytochrome P450 2C19P33261HumansPredicted (SEA)4418.49
Voltage-gated inwardly rectifying potassium channel KCNH2 structureClick to view 3D structureVoltage-gated inwardly rectifying potassium channel KCNH2Q12809HumansPredicted (SEA)5685.48
Adenosine receptor A3 structureClick to view 3D structureAdenosine receptor A3P0DMS8HumansPredicted (SEA)1772.08
Click to view 3D structureProcathepsin LP07154Rattus norvegicusPredicted (SEA)109.378
Concentrations
Not Available
External Links
DrugBank IDDB01602
HMDB IDHMDB0015540
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkBacampicillin
Chemspider ID390135
ChEBI ID2968
PubChem Compound ID441397
Kegg Compound IDC08122
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=1211909
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=29017833
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=464583
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=7012993
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=7012998
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=9131470