Epicillin (CED0021240)

Record Information
Version1.0
Creation Date2026-03-31 20:42:28 UTC
Update Date2026-08-19 16:49:17 UTC
Accession NumberCHEM057805
Identification
Common NameEpicillin
ClassSmall Molecule
Description
Epicillin is an organoheterocyclic compound with the formula C16H21N3O4S1 and an average molecular weight of 351.42 g/mol. Epicillin belongs to the beta lactams, a subclass of lactams within the organic compounds. This substance is found in or released from two recorded sources: food, food processing & cookware (specifically the preparation of wine or sparkling wine) and healthcare, pharmaceuticals & veterinary products (antibiotics). Recorded routes of exposure for this compound include oral and inhalation.
Contaminant TypeNot Available
Chemical Structure
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
DexacillinChEBI
DihydroampicillinChEBI
EpicilinaChEBI
EpicillineChEBI
EpicillinumChEBI
SpectacillinMeSH
6-(D-2-Amino-2-(1,4-cyclohexadien-1-yl)acetamido)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acidMeSH
SQ 11ChEMBL
302EPICILLINChEMBL
Chemical FormulaC16H21N3O4S1
Average Molecular Mass351.420 g/mol
Monoisotopic Mass351.125 g/mol
CAS Registry Number26774-90-3
IUPAC Name(2S,5R,6R)-6-[(2R)-2-amino-2-(cyclohexa-1,4-dien-1-yl)acetamido]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
Traditional Nameepicillin
SMILESCC1(C)S[C@@H]2[C@H](NC(=O)[C@H](N)C3=CCC=CC3)C(=O)N2[C@H]1C(O)=O
InChI IdentifierInChI=1S/C16H21N3O4S/c1-16(2)11(15(22)23)19-13(21)10(14(19)24-16)18-12(20)9(17)8-6-4-3-5-7-8/h3-4,7,9-11,14H,5-6,17H2,1-2H3,(H,18,20)(H,22,23)/t9-,10-,11+,14-/m1/s1
InChI KeyRPBAFSBGYDKNRG-NJBDSQKTSA-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
  • N-acyl-alpha amino acid or derivatives
  • Alpha-amino acid amide
  • Alpha-amino acid or derivatives
  • Tertiary carboxylic acid amide
  • Thiazolidine
  • Amino acid or derivatives
  • Azetidine
  • Carboxamide group
  • Secondary carboxylic acid amide
  • Amino acid
  • Azacycle
  • Dialkylthioether
  • Hemithioaminal
  • Thioether
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Amine
  • Organopnictogen compound
  • Primary aliphatic amine
  • Organonitrogen compound
  • Organooxygen compound
  • Organic oxygen compound
  • Carbonyl group
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Primary amine
  • 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 Solubility0.79 g/LALOGPS
logP1.04ALOGPS
logP-2.3ChemAxon
logS-2.6ALOGPS
pKa (Strongest Acidic)3.25ChemAxon
pKa (Strongest Basic)7.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area112.73 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity90.55 m³·mol⁻¹ChemAxon
Polarizability35.64 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrumsplash10-0a4i-2900000000-c7045805484f31f6dd66Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0bt9-1912000000-060ffbf32c460dab3f64Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0bt9-3910000000-82f8ffc007c17c3b465fNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a4i-9400000000-bcbcda176e6694a4418dNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a4i-0291000000-89f2709d46df02dfb0dcNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a4i-1591000000-387a4b1e9989d1f215e8Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-05di-9520000000-8c0f51f60ba354a6b5eaNot 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
6692.0Log mg/kg[3800:12000]RatLD50oralpredictedNot Available
Health Effects
Health EffectRelationshipDirectionReference
Exposure Sources
Source IDSourceSectorReference
233BrushesPersonal care & cosmeticsNot Available
306AntibioticsHealthcare, pharmaceuticals & veterinary productsNot Available
545Food PreservationFood, food processing & cookwareNot Available
549Preparation Of Wine Or Sparkling WineFood, food processing & cookwareNot Available
569Tobacco Smoke FiltersHousehold cleaning & consumer productsNot Available
632ApparelTextiles, leather & furnishingsNot Available
696NanotechnologyIndustrial manufacturing & chemical processingNot Available
698JewelleryMining & metal processingNot Available
Pathways
0 pathways

No pathways found

No metabolic pathways have been associated with this synthetic chemical

Targets
StructureProteinUniProt IDOrganismRelationshipDetails
Click to view 3D structureStreptokinase AP10520Streptococcus pyogenes serotype M1Predicted (SEA)247.093
Click to view 3D structureBeta-lactamase ACC-4A4ZYU9Escherichia coliPredicted (SEA)0.389246
Beta-lactamase structureClick to view 3D structureBeta-lactamaseP00811Escherichia coli (strain K12)Predicted (SEA)5.83869
Click to view 3D structureEfflux transporterQ3S5C3Salmonella newportPredicted (SEA)0.544945
Click to view 3D structureClass C beta-lactamase CMY-36Q48435Klebsiella pneumoniaePredicted (SEA)0.544945
Click to view 3D structureExtended-spectrum beta-lactamase PER-6D5HSX5Aeromonas allosaccharophilaPredicted (SEA)0.856341
Click to view 3D structureADC-14 proteinQ0VTR6Acinetobacter genomosp. 3Predicted (SEA)0.856341
Click to view 3D structureBeta-lactamase SHV-11Q7X575Escherichia coliPredicted (SEA)0.856341
Click to view 3D structureADC-16 proteinQ0VTR8Acinetobacter genomosp. 3Predicted (SEA)0.856341
Beta-lactamase TEM structureClick to view 3D structureBeta-lactamase TEMP62593Escherichia coliPredicted (SEA)2.25763
PER-2 beta-lactamase structureClick to view 3D structurePER-2 beta-lactamaseA2RP81Citrobacter freundiiPredicted (SEA)0.622794
Click to view 3D structureSolute carrier family 22 member 6Q4U2R8HumansPredicted (SEA)55.74
Click to view 3D structureOrganic anion transporter 3Q8TCC7HumansPredicted (SEA)20.3186
Bile salt export pump structureClick to view 3D structureBile salt export pumpO95342HumansPredicted (SEA)876.582
Click to view 3D structureMu-type opioid receptorP97266Cavia porcellusPredicted (SEA)1134.26
Delta-type opioid receptor structureClick to view 3D structureDelta-type opioid receptorP41143HumansPredicted (SEA)3361.3
Click to view 3D structurePenB class A beta-lactamaseB8R6A5Burkholderia cenocepaciaPredicted (SEA)1.79053
Click to view 3D structureBeta-lactamaseP94958Morganella morganiiPredicted (SEA)1.79053
Carbapenem-hydrolizing beta-lactamase SFC-1 structureClick to view 3D structureCarbapenem-hydrolizing beta-lactamase SFC-1Q6JP75Serratia fonticolaPredicted (SEA)1.79053
Click to view 3D structureDelta-type opioid receptorP33533Rattus norvegicusPredicted (SEA)1429.62
Click to view 3D structureMu-type opioid receptorP33535Rattus norvegicusPredicted (SEA)1648.46
Metallo-beta-lactamase type 2 structureClick to view 3D structureMetallo-beta-lactamase type 2P14488Bacillus cereusPredicted (SEA)1.79053
Delta-type opioid receptor structureClick to view 3D structureDelta-type opioid receptorP32300Mus musculusPredicted (SEA)1164.16
Mu-type opioid receptor structureClick to view 3D structureMu-type opioid receptorP35372HumansPredicted (SEA)4769.28
Beta-lactamase structureClick to view 3D structureBeta-lactamaseP05364Enterobacter cloacaePredicted (SEA)4.98235
Concentrations
Not Available
External Links
DrugBank IDDB13300
HMDB IDNot Available
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkEpicillin
Chemspider ID64486
ChEBI ID58974
PubChem Compound ID71392
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=1170316
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=1701026
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=4404324
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=7191790
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=9689