Meticillin (CED0000918)

Record Information
Version1.0
Creation Date2016-05-25 18:28:05 UTC
Update Date2026-08-19 20:38:01 UTC
Accession NumberCHEM022319
Identification
Common NameMeticillin
ClassSmall Molecule
Description
Meticillin is an organic compound with the formula C17H20N2O6S and an average molecular weight of 380.42 g/mol. Meticillin belongs to the amino acids, peptides, and analogues, a subclass of carboxylic acids and derivatives within the organic compounds. This compound is identified as an antibiotic and is found in or released from 35 recorded sources. These sources include healthcare, pharmaceuticals & veterinary products; drinking water & water supply; and food, food processing & cookware, specifically including food preservation, processing fish, fermentation processes for beer, and the preparation of malt, wine, or sparkling wine. It is also associated with household cleaning & consumer products, such as bleaching agents, ash trays, cigar cigarettes, other smoking requisites, and non electric simulated smoking devices. Additionally, it is found in electrical & electronic equipment, including amplifiers, antennas, coils, discharge lamps, and conductors or conductive bodies characterised by the conductive materials. Recorded exposure routes for meticillin include oral and inhalation. Meticillin interacts with six recorded protein targets. It acts as an inhibitor of MecA PBP2' (penicillin binding protein 2') (mecA). Other protein targets include penicillin-binding protein 2a (pbp2a), penicillin-binding protein 1b (pbp1b), penicillin-binding protein 2B (penA), and two other proteins.
Contaminant TypeNot Available
Chemical Structure
Synonyms
ValueSource
(2S,5R,6R)-6-[(2,6-Dimethoxybenzoyl)amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acidChEBI
6beta-(2,6-Dimethoxybenzamido)penicillanic acidChEBI
MeticilinaChEBI
MeticillineChEBI
MeticillinumChEBI
(2S,5R,6R)-6-[(2,6-Dimethoxybenzoyl)amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylateGenerator
6b-(2,6-Dimethoxybenzamido)penicillanateGenerator
6b-(2,6-Dimethoxybenzamido)penicillanic acidGenerator
6beta-(2,6-Dimethoxybenzamido)penicillanateGenerator
6Β-(2,6-dimethoxybenzamido)penicillanateGenerator
6Β-(2,6-dimethoxybenzamido)penicillanic acidGenerator
(2,6-Dimethoxyphenyl)penicillinHMDB
6-(2,6-Dimethoxybenzamido)penicillanic acidHMDB
MethicillinumHMDB
MethycillinHMDB
StaphcillinHMDB
CSL Brand OF methicillin sodiumHMDB
Dimethoxyphenyl penicillinHMDB
Penicillin, dimethoxyphenylHMDB
Methicillin hydrate, monosodium saltHMDB
Methicillin monohydrate, monosodium saltHMDB
Methicillin sodiumHMDB
MetinHMDB
MeticillinChEBI
Chemical FormulaC17H20N2O6S
Average Molecular Mass380.415 g/mol
Monoisotopic Mass380.104 g/mol
CAS Registry Number61-32-5
IUPAC Name(2S,5R,6R)-6-(2,6-dimethoxybenzamido)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
Traditional Namemethicillin
SMILES[H][C@]12SC(C)(C)[C@@H](N1C(=O)[C@H]2NC(=O)C1=C(OC)C=CC=C1OC)C(O)=O
InChI IdentifierInChI=1S/C17H20N2O6S/c1-17(2)12(16(22)23)19-14(21)11(15(19)26-17)18-13(20)10-8(24-3)6-5-7-9(10)25-4/h5-7,11-12,15H,1-4H3,(H,18,20)(H,22,23)/t11-,12+,15-/m1/s1
InChI KeyRJQXTJLFIWVMTO-TYNCELHUSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as alpha amino acid esters. These are ester derivatives of alpha amino acids.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentAlpha amino acid esters
Alternative Parents
Substituents
  • Alpha-amino acid ester
  • Penam
  • Azepane
  • Acylal
  • Dicarboxylic acid or derivatives
  • Beta-lactam
  • Tertiary carboxylic acid amide
  • Thiazolidine
  • Azetidine
  • Carboxamide group
  • Carboxylic acid ester
  • Lactam
  • Acetal
  • Amidine
  • Formamidine
  • Carboxylic acid amidine
  • Azacycle
  • Organoheterocyclic compound
  • Dialkylthioether
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Carboximidamide
  • Hemithioaminal
  • Thioether
  • Organic oxygen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Organopnictogen compound
  • Carbonyl group
  • Organic oxide
  • Hydrocarbon derivative
  • Organic nitrogen compound
  • 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 Solubility0.31 g/LALOGPS
logP1.79ALOGPS
logP0.79ChemAxon
logS-3.1ALOGPS
pKa (Strongest Acidic)2.96ChemAxon
pKa (Strongest Basic)-1.8ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area105.17 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity93.4 m³·mol⁻¹ChemAxon
Polarizability37.27 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrumsplash10-00xu-9756000000-82b89a7719dfc1d955bcNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS Spectrumsplash10-00di-9210200000-1eab4718d201402b682fNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-03k9-0975000000-99eb60da9aa2b5de1442Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-044i-1930000000-a4b4f247a46fae18026bNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0cei-5910000000-e7efdc9557d573640952Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-000i-0091000000-26a50b80740c915f0f14Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-000i-0392000000-c1ee20b1a433f17a6eadNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0079-8970000000-ce17545fc8fc88701a3fNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-001i-0419000000-d58fb75de5a467abe798Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-014i-0933000000-26dda514ee65613e1362Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-014i-2910000000-27d1d63f349d91f14d7aNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-003r-0908000000-956a7dbf20ae4631b6e1Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a6u-9735000000-0b07aadf554b6ef2480aNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-000y-9434000000-9284224377162a990dcaNot 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
6040.0Log mg/kg[3400:11000]RatLD50oralpredictedNot Available
Health Effects
Health EffectRelationshipDirectionReference
Exposure Sources
Source IDSourceSectorReference
10InsecticidesAgriculture & land managementNot Available
115Drinking waterDrinking water & water supplyNot Available
233BrushesPersonal care & cosmeticsNot Available
306AntibioticsHealthcare, pharmaceuticals & veterinary productsNot Available
505AmplifiersElectrical & Electronic EquipmentNot Available
506AntennasElectrical & Electronic EquipmentNot Available
508CoilsElectrical & Electronic EquipmentNot Available
511Conductors Or Conductive Bodies Characterised By The Conductive MaterialsElectrical & Electronic EquipmentNot Available
514Discharge LampsElectrical & Electronic EquipmentNot Available
516Electric Hearing AidsElectrical & Electronic EquipmentNot Available
517Electric SwitchesElectrical & Electronic EquipmentNot Available
518Electrically Stimulated Smoking DevicesElectrical & Electronic EquipmentNot Available
519ElectrodesElectrical & Electronic EquipmentNot Available
520Emergency Protective DevicesElectrical & Electronic EquipmentNot Available
521Fixed Capacitors And Their ManufactureElectrical & Electronic EquipmentNot Available
524Hybrid CapacitorsElectrical & Electronic EquipmentNot Available
527MagnetsElectrical & Electronic EquipmentNot Available
530Radio Transmission SystemsElectrical & Electronic EquipmentNot Available
537Television SystemsElectrical & Electronic EquipmentNot Available
539Video GamesElectrical & Electronic EquipmentNot Available
544Fermentation Processes For BeerFood, food processing & cookwareNot Available
545Food PreservationFood, food processing & cookwareNot Available
547Preparation Of MaltFood, food processing & cookwareNot Available
549Preparation Of Wine Or Sparkling WineFood, food processing & cookwareNot Available
551Processing FishFood, food processing & cookwareNot Available
552Processing MeatsFood, food processing & cookwareNot Available
554Ash TraysHousehold cleaning & consumer productsNot Available
555Bleaching AgentsHousehold cleaning & consumer productsNot Available
556Cigar CigarettesHousehold cleaning & consumer productsNot Available
559Non Electric Simulated Smoking DevicesHousehold cleaning & consumer productsNot Available
560Other Smoking RequisitesHousehold cleaning & consumer productsNot Available
561Perfumes Within Detergents And SoapsHousehold cleaning & consumer productsNot Available
562Pipe AccessoriesHousehold cleaning & consumer productsNot Available
563Soap DetergentsHousehold cleaning & consumer productsNot Available
564Soap DispensersHousehold cleaning & consumer productsNot Available
565Stands For Smoker RequirsitesHousehold cleaning & consumer productsNot Available
569Tobacco Smoke FiltersHousehold cleaning & consumer productsNot Available
579Manufacture Of Iron Or SteelIndustrial manufacturing & chemical processingNot Available
580Manufacture Preparation Of Tobacco ProductsIndustrial manufacturing & chemical processingNot Available
581Paper Making MachinesIndustrial manufacturing & chemical processingNot Available
596AcaricidesAgriculture & land managementNot Available
600Herbicides And AlgicidesAgriculture & land managementNot Available
602MolluscicidesAgriculture & land managementNot Available
603NematocidesAgriculture & land managementNot Available
605Pest RepellantsAgriculture & land managementNot Available
606Plant Growth RegulatorsAgriculture & land managementNot Available
609AftershavePersonal care & cosmeticsNot Available
610Aftersun ProductsPersonal care & cosmeticsNot Available
611Anti Perspirants Or Body DeoderantsPersonal care & cosmeticsNot Available
612Body Washing Or Cleaning ImplementsPersonal care & cosmeticsNot Available
613DepilatoriesPersonal care & cosmeticsNot Available
614Essential Oils Or PerfumesPersonal care & cosmeticsNot Available
615Eye Makeup ProductsPersonal care & cosmeticsNot Available
616Face Mask CosmeticsPersonal care & cosmeticsNot Available
617Lip Care ProductsPersonal care & cosmeticsNot Available
618Lip Makeup ProductsPersonal care & cosmeticsNot Available
619Manicure PedicurePersonal care & cosmeticsNot Available
630ToysRecreation & sports surfacesNot Available
632ApparelTextiles, leather & furnishingsNot Available
642FootwearTextiles, leather & furnishingsNot Available
643HeadwearTextiles, leather & furnishingsNot Available
644Hook Or Eye FastenersTextiles, leather & furnishingsNot Available
650Purses Luggage Hand BagsTextiles, leather & furnishingsNot Available
651Purses Money Bags WalletsTextiles, leather & furnishingsNot Available
652RopesTextiles, leather & furnishingsNot Available
662Yarns Or ThreadsTextiles, leather & furnishingsNot Available
663Sanitary EquipmentWastewater, sanitation & biosolidsNot Available
Pathways
1 pathway
Targets
StructureProteinUniProt IDOrganismRelationshipDetails
Click to view 3D structureBeta-lactamase ACC-4A4ZYU9Escherichia coliPredicted (SEA)0.0778492
Click to view 3D structureStreptokinase AP10520Streptococcus pyogenes serotype M1Predicted (SEA)72.7112
Click to view 3D structureEfflux transporterQ3S5C3Salmonella newportPredicted (SEA)0.155698
Click to view 3D structureClass C beta-lactamase CMY-36Q48435Klebsiella pneumoniaePredicted (SEA)0.155698
Bile salt export pump structureClick to view 3D structureBile salt export pumpO95342HumansPredicted (SEA)47.7994
Beta-lactamase structureClick to view 3D structureBeta-lactamaseP00811Escherichia coli (strain K12)Predicted (SEA)3.89246
Speckle-type POZ protein structureClick to view 3D structureSpeckle-type POZ proteinO43791HumansPredicted (SEA)2.33548
Click to view 3D structureD(2) dopamine receptorP61169RatPredicted (SEA)1184.79
Click to view 3D structure5-hydroxytryptamine receptor 1AP19327Rattus norvegicusPredicted (SEA)1285.76
Beta-lactamase TEM structureClick to view 3D structureBeta-lactamase TEMP62593Escherichia coliPredicted (SEA)1.94623
Peregrin structureClick to view 3D structurePeregrinP55201HumansPredicted (SEA)159.824
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
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)415.637
Bromodomain-containing protein 4 structureClick to view 3D structureBromodomain-containing protein 4O60885HumansPredicted (SEA)871.444
D(4) dopamine receptor structureClick to view 3D structureD(4) dopamine receptorP21917HumansPredicted (SEA)1794.11
Induced myeloid leukemia cell differentiation protein Mcl-1 structureClick to view 3D structureInduced myeloid leukemia cell differentiation protein Mcl-1Q07820HumansPredicted (SEA)1011.34
Click to view 3D structureReceptor (TNFRSF)-interacting serine-threonine kinase 1 (Predicted)D3ZYL0Rattus norvegicusPredicted (SEA)62.0458
Transcription factor EB structureClick to view 3D structureTranscription factor EBP19484HumansPredicted (SEA)54.3388
D(2) dopamine receptor structureClick to view 3D structureD(2) dopamine receptorP14416HumansPredicted (SEA)2970.65
Click to view 3D structurePER-2 beta-lactamaseA2RP81Citrobacter freundiiPredicted (SEA)0.544945
Voltage-gated inwardly rectifying potassium channel KCNH2 structureClick to view 3D structureVoltage-gated inwardly rectifying potassium channel KCNH2Q12809HumansPredicted (SEA)5233.02
Click to view 3D structureD(3) dopamine receptorP19020Rattus norvegicusPredicted (SEA)914.728
Concentrations
Not Available
External Links
DrugBank IDDB01603
HMDB IDHMDB0015541
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDMII
Wikipedia LinkMeticillin
Chemspider ID5862
ChEBI ID6827
PubChem Compound ID6087
Kegg Compound IDC07177
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=11969119
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=12569987
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=24405901
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=24433925
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=26962156