Carbapenem

Synopsis, Chemistry

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Also known as: 2,3-didehydro-1-carbapenam, (5r)-1-azabicyclo[3.2.0]hept-2-en-7-one, Cis-carbapenem, Schembl37243, Chebi:46765, Q27120700

Molecular Formula

C₆H₇NO

Molecular Weight

109.13 g/mol

InChI Key

YZBQHRLRFGPBSL-RXMQYKEDSA-N

A group of beta-lactam antibiotics in which the sulfur atom in the thiazolidine ring of the penicillin molecule is replaced by a carbon atom. THIENAMYCINS are a subgroup of carbapenems which have a sulfur atom as the first constituent of the side chain.

1 2D Structure

Carbapenem

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(5R)-1-azabicyclo[3.2.0]hept-2-en-7-one

2.1.2 InChI

InChI=1S/C6H7NO/c8-6-4-5-2-1-3-7(5)6/h1,3,5H,2,4H2/t5-/m1/s1

2.1.3 InChI Key

YZBQHRLRFGPBSL-RXMQYKEDSA-N

2.1.4 Canonical SMILES

C1C=CN2C1CC2=O

2.1.5 Isomeric SMILES

C1C=CN2[C@H]1CC2=O

2.2 Synonyms

2.2.1 MeSH Synonyms

1. Antibiotics, Carbapenem

2. Carbapenem Antibiotics

3. Carbapenems

2.2.2 Depositor-Supplied Synonyms

1. 2,3-didehydro-1-carbapenam

2. (5r)-1-azabicyclo[3.2.0]hept-2-en-7-one

3. Cis-carbapenem

4. Schembl37243

5. Chebi:46765

6. Q27120700

2.3 Create Date

2007-02-08

3 Chemical and Physical Properties

Molecular Formula	C₆H₇NO
Molecular Weight	109.13 g/mol
XLogP3	0
Hydrogen Bond Donor Count	0
Hydrogen Bond Acceptor Count	1
Rotatable Bond Count	0
Exact Mass	109.052763847 g/mol
Monoisotopic Mass	109.052763847 g/mol
Topological Polar Surface Area	20.3 Å²
Heavy Atom Count	8
Formal Charge	0
Complexity	162
Isotope Atom Count	0
Defined Atom Stereocenter Count	1
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1