(5R,6S)-3-[(2-aminoethyl)sulfanyl]-6-[(1R)-1-hydroxyethyl]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid

• ChemBase ID: 129852
• Molecular Formular: C11H16N2O4S
• Molecular Mass: 272.32074
• Monoisotopic Mass: 272.083078
• SMILES: O=C(O)C1=C(SCCN)C[C@H]2N1C(=O)[C@@H]2[C@H](O)C
• Canonical SMILES: NCCSC1=C(C(=O)O)N2[C@H](C1)[C@H](C2=O)[C@H](O)C
• InChI: InChI=1S/C11H16N2O4S/c1-5(14)8-6-4-7(18-3-2-12)9(11(16)17)13(6)10(8)15/h5-6,8,14H,2-4,12H2,1H3,(H,16,17)/t5-,6-,8-/m1/s1
• InChIKey: WKDDRNSBRWANNC-ATRFCDNQSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (5R,6S)-3-[(2-aminoethyl)sulfanyl]-6-[(1R)-1-hydroxyethyl]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid
• IUPAC Traditional name: thienamycin
• Synonyms: Thienamycin

Database IDs

• CAS Number: 59995-64-1
• PubChem SID: 162224138
• PubChem CID: 441128
• CHEMBL: 278773
• Chemspider ID: 389922
• Wikipedia Title: Thienamycin

CALCULATED PROPERTIES

• Acid pKa: 3.6664314
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): -4.313837
• LogD (pH = 7.4): -4.3109164
• Log P: -4.309642
• Molar Refractivity: 68.7109 cm^3
• Polarizability: 26.337885 Å^3
• Polar Surface Area: 103.86 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true