Meropenem (CHEM018371)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-22 05:11:43 UTC
Update Date2016-11-09 01:15:47 UTC
Accession NumberCHEM018371
Identification
Common NameMeropenem
ClassSmall Molecule
DescriptionA carbapenemcarboxylic acid in which the azetidine and pyrroline rings carry 1-hydroxymethyl and in which the azetidine and pyrroline rings carry 1-hydroxymethyl and 5-(dimethylcarbamoyl)pyrrolidin-3-ylthio substituents respectively.
Contaminant Sources
  • HMDB Contaminants - Urine
  • STOFF IDENT Compounds
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
(1R,5S,6S)-2-[(3S,5S)-5-DIMETHYLAMINOCARBONYLPYRROLIDIN-3-ylthio]-6-[(R)-1-hydroxyethyl]-1-methylcarbapen-2-em-3-carboxylIC ACIDChEBI
(4R,5S,6S)-3-{[(3S,5S)-5-(dimethylcarbamoyl)pyrrolidin-3-yl]thio}-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acidChEBI
Antibiotic SM 7338ChEBI
MEPMChEBI
Meropenem anhydrousChEBI
MeropenemumChEBI
Merrem i.v.Kegg
MeronemKegg
(1R,5S,6S)-2-[(3S,5S)-5-DIMETHYLAMINOCARBONYLPYRROLIDIN-3-ylthio]-6-[(R)-1-hydroxyethyl]-1-methylcarbapen-2-em-3-carboxylateGenerator
(4R,5S,6S)-3-{[(3S,5S)-5-(dimethylcarbamoyl)pyrrolidin-3-yl]thio}-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylateGenerator
3-(5-Dimethylcarbamoylpyrrolidin-3-ylthio)-6-(1-hydroxyethyl)-4-methyl-7-oxo-1-azabicyclo(3.2.0)hept-2-ene-2-carboxylic acidHMDB
MerremHMDB
RonemHMDB
PenemHMDB
Chemical FormulaC17H25N3O5S
Average Molecular Mass383.463 g/mol
Monoisotopic Mass383.151 g/mol
CAS Registry Number96036-03-2
IUPAC Name(4R,5S,6S)-3-{[(3S,5S)-5-(dimethylcarbamoyl)pyrrolidin-3-yl]sulfanyl}-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid
Traditional Namemeropenem
SMILES[H][C@]1([C@@H](C)O)C(=O)N2C(C(O)=O)=C(S[C@@H]3CN[C@@H](C3)C(=O)N(C)C)[C@H](C)[C@]12[H]
InChI IdentifierInChI=1S/C17H25N3O5S/c1-7-12-11(8(2)21)16(23)20(12)13(17(24)25)14(7)26-9-5-10(18-6-9)15(22)19(3)4/h7-12,18,21H,5-6H2,1-4H3,(H,24,25)/t7-,8-,9+,10+,11-,12-/m1/s1
InChI KeyDMJNNHOOLUXYBV-PQTSNVLCSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as thienamycins. These are beta-lactam antibiotics that differ from penicillins in having the thiazolidine sulfur atom replaced by carbon, the sulfur then becoming the first atom in the side chain.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassLactams
Sub ClassBeta lactams
Direct ParentThienamycins
Alternative Parents
Substituents
  • Thienamycin
  • Proline or derivatives
  • Alpha-amino acid amide
  • Alpha-amino acid or derivatives
  • Pyrrolidine carboxylic acid or derivatives
  • Pyrrolidine-2-carboxamide
  • Pyrroline carboxylic acid
  • Pyrroline carboxylic acid or derivatives
  • Azepine
  • Vinylogous thioester
  • Pyrrolidine
  • Pyrroline
  • Tertiary carboxylic acid amide
  • Amino acid or derivatives
  • Azetidine
  • Carboxamide group
  • Amino acid
  • Thioenolether
  • Secondary alcohol
  • Secondary amine
  • Sulfenyl compound
  • Azacycle
  • Carboxylic acid derivative
  • Carboxylic acid
  • Secondary aliphatic amine
  • Monocarboxylic acid or derivatives
  • Amine
  • Alcohol
  • Organic nitrogen compound
  • Carbonyl group
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Organosulfur compound
  • Organic oxide
  • Organic oxygen 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 Solubility5.63 g/LALOGPS
logP-0.69ALOGPS
logP-4.4ChemAxon
logS-1.8ALOGPS
pKa (Strongest Acidic)3.47ChemAxon
pKa (Strongest Basic)9.39ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area110.18 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity97.89 m³·mol⁻¹ChemAxon
Polarizability39.29 ųChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0g6r-9165000000-bfa50046e33decc913f0Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-00dl-9320210000-71603485baf0ee1f92c6Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01ox-0936000000-857a771e636fb53260aeSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-02tc-1977000000-43d0012adc5dc96ecabdSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0hfx-9840000000-2ccf21d5dcd32f3989c7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0229000000-f9d8bdfc2564aeca32aeSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-9521000000-83bc2070b161829e83c8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0002-2900000000-e17d924d7e7692764373Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0009000000-5e44660aff42cac149bdSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00lr-0009000000-4dd3b9244a8243c4b20dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udi-4911000000-def7d662e5166c4d5e94Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0009000000-d7eed5c18e5f3c6f6f92Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-017l-1289000000-11238b0e8232b05612fcSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-08nc-3294000000-363e013578d0e013c800Spectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
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 IDDB00760
HMDB IDHMDB0014898
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkMeropenem
Chemspider ID389924
ChEBI ID43968
PubChem Compound ID441130
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=10776838
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=11069213
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=18611786
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=18645546
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=28343819
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=28371721
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=28583381
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=28669829
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=28677407
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=7588092