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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:52 UTC
Update Date2019-01-11 19:35:59 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?1547235359
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
StaphcillinMeSH
CSL Brand OF methicillin sodiumMeSH
Dimethoxyphenyl penicillinMeSH
Penicillin, dimethoxyphenylMeSH
Methicillin hydrate, monosodium saltMeSH
Methicillin monohydrate, monosodium saltMeSH
Methicillin sodiumMeSH
MetinMeSH
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
DescriptionThis compound 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:

Role

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.31 g/LNot Available
LogP1.22HANSCH,C ET AL. (1995)
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 RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00xu-9756000000-82b89a7719dfc1d955bcView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00di-9210200000-1eab4718d201402b682fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03k9-0975000000-99eb60da9aa2b5de1442View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-044i-1930000000-a4b4f247a46fae18026bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0cei-5910000000-e7efdc9557d573640952View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0091000000-26a50b80740c915f0f14View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0392000000-c1ee20b1a433f17a6eadView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0079-8970000000-ce17545fc8fc88701a3fView in MoNA
Biological Properties
Cellular Locations
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB01603 details
UrineExpected but not Quantified Not 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
FoodDB 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
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available