(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 trihydrate

• ChemBase ID: 157542
• Molecular Formular: C17H31N3O8S
• Molecular Mass: 437.50834
• Monoisotopic Mass: 437.18318597
• SMILES: C[C@@H]1[C@@H]2[C@H](C(=O)N2C(=C1S[C@H]1C[C@H](NC1)C(=O)N(C)C)C(=O)O)[C@@H](C)O.O.O.O
• Canonical SMILES: C[C@H]([C@H]1C(=O)N2[C@@H]1[C@@H](C)C(=C2C(=O)O)S[C@@H]1CN[C@@H](C1)C(=O)N(C)C)O.O.O.O
• InChI: InChI=1S/C17H25N3O5S.3H2O/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);3*1H2/t7-,8-,9+,10+,11-,12-;;;/m1.../s1
• InChIKey: CTUAQTBUVLKNDJ-OBZXMJSBSA-N

NAMES AND DATABASE IDS

Names

• 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 trihydrate
• IUPAC Traditional name: meropenem trihydrate
• Synonyms: (1R,5S,6S)-2-[(3S,5S)-5-(dimethylaminocarbonyl)pyrrolidin-3-ylthio]-6-[(R)-1-hydroxyethyl]-1-methylcarbapen-2-em-3-carboxylic acid trihydrate; Meropenem trihydrate

Database IDs

• CAS Number: 119478-56-7
• MDL Number: MFCD08600005
• PubChem SID: 162251679
• PubChem CID: 441129

CALCULATED PROPERTIES

• Acid pKa: 3.4704194
• H Acceptors: 6
• H Donor: 3
• LogD (pH = 5.5): -4.3561654
• LogD (pH = 7.4): -4.3568015
• Log P: -4.353987
• Molar Refractivity: 97.8862 cm^3
• Polarizability: 37.879482 Å^3
• Polar Surface Area: 110.18 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Safety Information

• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319
• GHS Precautionary statements: P305 + P351 + P338

Product Information

• Grade: VETRANAL™, analytical standard
• Empirical Formula (Hill Notation): C17H25N3O5S · 3H2O

DETAILS

Sigma Aldrich - 32460

Biochem/physiol Actions
Meropenem trihydrate is an ultra-broad spectrum beta-lactam antibiotic active against both Gram-positive and Gram-negative bacteria.
Legal Information
VETRANAL is a trademark of Sigma-Aldrich Co. LLC