(5R,6R)-3-(2-aminoethylsulfanyl)-6-[(1R)-1-hydroxyethyl]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid
Basic information
- CAS
59995-64-1- Standard SMILES
C[C@@H](O)[C@@H]1C(=O)N2C(C(=O)O)=C(SCCN)C[C@H]12- InChIKey
WKDDRNSBRWANNC-JKMUOGBPSA-N- Molecular formula
- C11H16N2O4S
- Average molar mass
- 272.32 g/mol
- Monoisotopic mass
- 272.08307817
Overview
thienamycin has been reported in Streptomyces and Streptomyces cattleya with data available.
Names & identifiers
- Preferred name
- (5R,6R)-3-(2-aminoethylsulfanyl)-6-[(1R)-1-hydroxyethyl]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid
- IUPAC
- (5R,6R)-3-(2-aminoethylsulfanyl)-6-[(1R)-1-hydroxyethyl]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid
- English name
- Thienamycin
- Molecular formula
- C11H16N2O4S
- Molecular weight
- 272.32
Names & synonyms
Thienamicin(5R,6R)-3-(2-aminoethylsulfanyl)-6-[(1R)-1-hydroxyethyl]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid2-((1R)-1-Hydroxyethyl)-4-(2-aminoethylthio)-1-oxo-2H,2aH-azetidino[1,2-d]2-pyrroline-5-carboxylic acidImipenem EP Impurity A(+)-ThienamycinThienamycin (>80%)IMipeneM IMpurity AThienamycin USP/EP/BPImipenemum Impurity A(3As,7As)-Octahydro-2-benzofuranImipenem Impurity 1(Imipenem EP Impurity A)(5R)-3-(2-Aminoethylthio)-6β-[(R)-1-hydroxyethyl]-7-oxo-1-azabicyclo[3.2.0]hepta-2-ene-2-carboxylic acid
Show more names
(5R)-3-[(2-Aminoethyl)thio]-6β-[(R)-1-hydroxyethyl]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid
Properties
Computed structural properties
- XLogP
- -3
- Topological polar surface area
- 129 Ų
- Hydrogen bond donors
- 3
- Hydrogen bond acceptors
- 6
- Rotatable bonds
- 5
- Heavy atoms
- 18
- Formal charge
- 0
- Complexity
- 423
Physicochemical properties
- alpha
- 27 · D27 +82.7° (c = 1.0 in water)
- Boiling point
- 514 · 514.0±50.0 °C(Predicted)
- Density
- 1.5 · 1.50±0.1 g/cm3(Predicted)
- storage temp.
- -86 °C · Hygroscopic, -86°C Freezer, Under inert atmosphere
- solubility
- Chloroform (Slightly), Methanol (Slightly), Water (Slightly)
- form
- Solid
- pka
- 4.2 · 4.20±0.40(Predicted)
- color
- Off-White to Dark Yellow
- Stability
- Hygroscopic, Temperature Sensitive, Very Unstable
- 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
- SMILES
- N12[C@@]([H])([C@@H]([C@H](O)C)C1=O)CC(SCCN)=C2C(O)=O
- FDA UNII
- 5 I5964P · WMW5I5964P
Chemistry & industry
Applications
DescriptionThienamycin, one of the most potent naturally-produced antibiotics known thus far, was discovered in Streptomyces cattleya in 1976. Thienamycin has excellent activity against both Gram-positive and Gram-negative bacteria and is resistant to bacterial β-lactamase enzymes.
UsesThienamycin is one of the most potent naturally produced antibiotics known thus far. It has excellent activity against both Gram-positive and Gram-negative bacteria and is resistant to bacterial β-lactamase enzymes.
Upstream & downstream products
Upstream raw materials
Additional notes
DefinitionChEBI: Thienamycin is a member of carbapenems.
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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