Meticillin (CHEM022319)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 18:28:05 UTC
Update Date2026-04-13 20:59:08 UTC
Accession NumberCHEM022319
Identification
Common NameMeticillin
ClassSmall Molecule
DescriptionA penicillin that is 6-aminopenicillanic acid in which one of the amino hydrogens is replaced by a 2,6-dimethoxybenzoyl group.
Contaminant Sources
  • HMDB Contaminants - Urine
  • STOFF IDENT Compounds
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
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
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot 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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00xu-9756000000-82b89a7719dfc1d955bcSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00di-9210200000-1eab4718d201402b682fSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03k9-0975000000-99eb60da9aa2b5de1442Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-044i-1930000000-a4b4f247a46fae18026bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0cei-5910000000-e7efdc9557d573640952Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0091000000-26a50b80740c915f0f14Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0392000000-c1ee20b1a433f17a6eadSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0079-8970000000-ce17545fc8fc88701a3fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0419000000-d58fb75de5a467abe798Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-0933000000-26dda514ee65613e1362Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014i-2910000000-27d1d63f349d91f14d7aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-003r-0908000000-956a7dbf20ae4631b6e1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a6u-9735000000-0b07aadf554b6ef2480aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000y-9434000000-9284224377162a990dcaSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
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