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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:52 UTC
Update Date2021-09-14 15:19:52 UTC
HMDB IDHMDB0015541
Secondary Accession Numbers
  • HMDB15541
Metabolite Identification
Common NameMeticillin
DescriptionMeticillin is only found in individuals that have used or taken this drug. It is one of the penicillins which is resistant to penicillinase but susceptible to a penicillin-binding protein. It is inactivated by gastric acid so administered by injection. [PubChem]Like other beta-lactam antibiotics, meticillin acts by inhibiting the synthesis of bacterial cell walls. It inhibits cross-linkage between the linear peptidoglycan polymer chains that make up a major component of the cell wall of Gram-positive bacteria. It does this by binding to and competitively inhibiting the transpeptidase enzyme used by bacteria to cross-link the peptide (D-alanyl-alanine) used in peptidogylcan synthesis.
Structure
Data?1582753308
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 Weight380.415
Monoisotopic Molecular Weight380.104207072
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
CAS Registry Number61-32-5
SMILES
[H][C@]12SC(C)(C)[C@@H](N1C(=O)[C@H]2NC(=O)C1=C(OC)C=CC=C1OC)C(O)=O
InChI Identifier
InChI=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 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
  • Penicillin
  • N-acyl-alpha amino acid or derivatives
  • Alpha-amino acid or derivatives
  • Dimethoxybenzene
  • M-dimethoxybenzene
  • Benzoic acid or derivatives
  • Benzamide
  • Penam
  • Phenoxy compound
  • Phenol ether
  • Benzoyl
  • Anisole
  • Methoxybenzene
  • Alkyl aryl ether
  • Benzenoid
  • Monocyclic benzene moiety
  • Beta-lactam
  • Thiazolidine
  • Tertiary carboxylic acid amide
  • Carboxamide group
  • Azetidine
  • Lactam
  • Secondary carboxylic acid amide
  • Azacycle
  • Organoheterocyclic compound
  • Dialkylthioether
  • Hemithioaminal
  • Thioether
  • Carboxylic acid
  • Ether
  • Monocarboxylic acid or derivatives
  • Hydrocarbon derivative
  • Carbonyl group
  • Organooxygen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Organonitrogen compound
  • Organic oxide
  • Organic nitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Biological location

Source

Route of exposure

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.31 g/LNot Available
LogP1.22HANSCH,C ET AL. (1995)
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.31 g/LALOGPS
logP10(1.79) g/LALOGPS
logP10(0.79) g/LChemAxon
logS10(-3.1) g/LALOGPS
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
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+185.62531661259
DarkChem[M-H]-185.8431661259

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Meticillin[H][C@]12SC(C)(C)[C@@H](N1C(=O)[C@H]2NC(=O)C1=C(OC)C=CC=C1OC)C(O)=O4450.5Standard polar33892256
Meticillin[H][C@]12SC(C)(C)[C@@H](N1C(=O)[C@H]2NC(=O)C1=C(OC)C=CC=C1OC)C(O)=O2746.8Standard non polar33892256
Meticillin[H][C@]12SC(C)(C)[C@@H](N1C(=O)[C@H]2NC(=O)C1=C(OC)C=CC=C1OC)C(O)=O3155.6Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Meticillin,1TMS,isomer #1COC1=CC=CC(OC)=C1C(=O)N[C@@H]1C(=O)N2[C@@H](C(=O)O[Si](C)(C)C)C(C)(C)S[C@H]122947.4Semi standard non polar33892256
Meticillin,1TMS,isomer #2COC1=CC=CC(OC)=C1C(=O)N([C@@H]1C(=O)N2[C@@H](C(=O)O)C(C)(C)S[C@H]12)[Si](C)(C)C2905.3Semi standard non polar33892256
Meticillin,2TMS,isomer #1COC1=CC=CC(OC)=C1C(=O)N([C@@H]1C(=O)N2[C@@H](C(=O)O[Si](C)(C)C)C(C)(C)S[C@H]12)[Si](C)(C)C2888.4Semi standard non polar33892256
Meticillin,2TMS,isomer #1COC1=CC=CC(OC)=C1C(=O)N([C@@H]1C(=O)N2[C@@H](C(=O)O[Si](C)(C)C)C(C)(C)S[C@H]12)[Si](C)(C)C2863.6Standard non polar33892256
Meticillin,2TMS,isomer #1COC1=CC=CC(OC)=C1C(=O)N([C@@H]1C(=O)N2[C@@H](C(=O)O[Si](C)(C)C)C(C)(C)S[C@H]12)[Si](C)(C)C3633.4Standard polar33892256
Meticillin,1TBDMS,isomer #1COC1=CC=CC(OC)=C1C(=O)N[C@@H]1C(=O)N2[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)C(C)(C)S[C@H]123202.2Semi standard non polar33892256
Meticillin,1TBDMS,isomer #2COC1=CC=CC(OC)=C1C(=O)N([C@@H]1C(=O)N2[C@@H](C(=O)O)C(C)(C)S[C@H]12)[Si](C)(C)C(C)(C)C3136.0Semi standard non polar33892256
Meticillin,2TBDMS,isomer #1COC1=CC=CC(OC)=C1C(=O)N([C@@H]1C(=O)N2[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)C(C)(C)S[C@H]12)[Si](C)(C)C(C)(C)C3304.6Semi standard non polar33892256
Meticillin,2TBDMS,isomer #1COC1=CC=CC(OC)=C1C(=O)N([C@@H]1C(=O)N2[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)C(C)(C)S[C@H]12)[Si](C)(C)C(C)(C)C3324.3Standard non polar33892256
Meticillin,2TBDMS,isomer #1COC1=CC=CC(OC)=C1C(=O)N([C@@H]1C(=O)N2[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)C(C)(C)S[C@H]12)[Si](C)(C)C(C)(C)C3779.1Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Meticillin GC-MS (Non-derivatized) - 70eV, Positivesplash10-00xu-9756000000-82b89a7719dfc1d955bc2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Meticillin GC-MS (1 TMS) - 70eV, Positivesplash10-00di-9210200000-1eab4718d201402b682f2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Meticillin GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Meticillin GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Meticillin 10V, Positive-QTOFsplash10-03k9-0975000000-99eb60da9aa2b5de14422016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Meticillin 20V, Positive-QTOFsplash10-044i-1930000000-a4b4f247a46fae18026b2016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Meticillin 40V, Positive-QTOFsplash10-0cei-5910000000-e7efdc9557d5736409522016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Meticillin 10V, Negative-QTOFsplash10-000i-0091000000-26a50b80740c915f0f142016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Meticillin 20V, Negative-QTOFsplash10-000i-0392000000-c1ee20b1a433f17a6ead2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Meticillin 40V, Negative-QTOFsplash10-0079-8970000000-ce17545fc8fc88701a3f2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Meticillin 10V, Positive-QTOFsplash10-001i-0419000000-d58fb75de5a467abe7982021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Meticillin 20V, Positive-QTOFsplash10-014i-0933000000-26dda514ee65613e13622021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Meticillin 40V, Positive-QTOFsplash10-014i-2910000000-27d1d63f349d91f14d7a2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Meticillin 10V, Negative-QTOFsplash10-003r-0908000000-956a7dbf20ae4631b6e12021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Meticillin 20V, Negative-QTOFsplash10-0a6u-9735000000-0b07aadf554b6ef2480a2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Meticillin 40V, Negative-QTOFsplash10-000y-9434000000-9284224377162a990dca2021-10-11Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01603 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01603 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB01603
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID5862
KEGG Compound IDC07177
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkMeticillin
METLIN IDNot Available
PubChem Compound6087
PDB IDMII
ChEBI ID6827
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available