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3-[(2-Aminoethyl)sulfanyl]-7-oxo-1-azabicyclo[3.2.0]heptane-2-carboxylic acid

PubChem CID
77879312
Structure
3-[(2-Aminoethyl)sulfanyl]-7-oxo-1-azabicyclo[3.2.0]heptane-2-carboxylic acid_small.png
3-[(2-Aminoethyl)sulfanyl]-7-oxo-1-azabicyclo[3.2.0]heptane-2-carboxylic acid_3D_Structure.png
Molecular Formula
Synonyms
  • CHEBI:132304
  • 3-(2-aminoethylthio)-7-oxo-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
  • 3-[(2-aminoethyl)sulfanyl]-7-oxo-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
  • Carbapenem biosynthesis intermediate 1
  • 3-((2-Aminoethyl)sulfanyl)-7-oxo-1-azabicyclo(3.2.0)heptane-2-carboxylate
Molecular Weight
230.29 g/mol
Computed by PubChem 2.1 (PubChem release 2021.05.07)
Dates
  • Create:
    2014-09-23
  • Modify:
    2025-02-01
Description
3-[(2-aminoethyl)sulfanyl]-7-oxo-1-azabicyclo[3.2.0]heptane-2-carboxylic acid is a beta-lactam that is 7-oxo-1-azabicyclo[3.2.0]heptane-2-carboxylic acid carrying an additional (2-aminoethyl)sulfanyl substituent at position 3. An intermediate in the biosynthesis of carbapenem. It has a role as a bacterial metabolite. It is a beta-lactam, an aliphatic sulfide, a monocarboxylic acid, an organic heterobicyclic compound and a primary amino compound.
3-[(2-Aminoethyl)sulfanyl]-7-oxo-1-azabicyclo[3.2.0]heptane-2-carboxylic acid has been reported in Apis cerana with data available.

1 Structures

1.1 2D Structure

Chemical Structure Depiction
3-[(2-Aminoethyl)sulfanyl]-7-oxo-1-azabicyclo[3.2.0]heptane-2-carboxylic acid.png

1.2 3D Conformer

2 Names and Identifiers

2.1 Computed Descriptors

2.1.1 IUPAC Name

3-(2-aminoethylsulfanyl)-7-oxo-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
Computed by Lexichem TK 2.7.0 (PubChem release 2021.05.07)

2.1.2 InChI

InChI=1S/C9H14N2O3S/c10-1-2-15-6-3-5-4-7(12)11(5)8(6)9(13)14/h5-6,8H,1-4,10H2,(H,13,14)
Computed by InChI 1.0.6 (PubChem release 2021.05.07)

2.1.3 InChIKey

WSFRFSBEAWNRAE-UHFFFAOYSA-N
Computed by InChI 1.0.6 (PubChem release 2021.05.07)

2.1.4 SMILES

C1C2CC(=O)N2C(C1SCCN)C(=O)O
Computed by OEChem 2.3.0 (PubChem release 2024.12.12)

2.2 Molecular Formula

C9H14N2O3S
Computed by PubChem 2.1 (PubChem release 2021.05.07)

2.3 Other Identifiers

2.3.1 ChEBI ID

2.3.2 KEGG ID

2.3.3 Wikidata

2.4 Synonyms

2.4.1 Depositor-Supplied Synonyms

3 Chemical and Physical Properties

3.1 Computed Properties

Property Name
Molecular Weight
Property Value
230.29 g/mol
Reference
Computed by PubChem 2.1 (PubChem release 2021.05.07)
Property Name
XLogP3-AA
Property Value
-3.2
Reference
Computed by XLogP3 3.0 (PubChem release 2021.05.07)
Property Name
Hydrogen Bond Donor Count
Property Value
2
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.05.07)
Property Name
Hydrogen Bond Acceptor Count
Property Value
5
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.05.07)
Property Name
Rotatable Bond Count
Property Value
4
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.05.07)
Property Name
Exact Mass
Property Value
230.07251349 Da
Reference
Computed by PubChem 2.1 (PubChem release 2021.05.07)
Property Name
Monoisotopic Mass
Property Value
230.07251349 Da
Reference
Computed by PubChem 2.1 (PubChem release 2021.05.07)
Property Name
Topological Polar Surface Area
Property Value
109 Ų
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.05.07)
Property Name
Heavy Atom Count
Property Value
15
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
297
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.05.07)
Property Name
Isotope Atom Count
Property Value
0
Reference
Computed by PubChem
Property Name
Defined Atom Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Undefined Atom Stereocenter Count
Property Value
3
Reference
Computed by PubChem
Property Name
Defined Bond Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Undefined Bond Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Covalently-Bonded Unit Count
Property Value
1
Reference
Computed by PubChem
Property Name
Compound Is Canonicalized
Property Value
Yes
Reference
Computed by PubChem (release 2019.01.04)

5 Literature

5.1 Consolidated References

5.2 Chemical Co-Occurrences in Literature

5.3 Chemical-Disease Co-Occurrences in Literature

6 Taxonomy

The LOTUS Initiative for Open Natural Products Research: frozen dataset union wikidata (with metadata) | DOI:10.5281/zenodo.5794106

7 Classification

7.1 ChEBI Ontology

7.2 LOTUS Tree

7.3 MolGenie Organic Chemistry Ontology

8 Information Sources

  1. ChEBI
    3-[(2-aminoethyl)sulfanyl]-7-oxo-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
    https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:132304
  2. LOTUS - the natural products occurrence database
    LICENSE
    The code for LOTUS is released under the GNU General Public License v3.0.
    https://lotus.nprod.net/
    3-[(2-Aminoethyl)sulfanyl]-7-oxo-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
    https://www.wikidata.org/wiki/Q27225525
  3. KEGG
    LICENSE
    Academic users may freely use the KEGG website. Non-academic use of KEGG generally requires a commercial license
    https://www.kegg.jp/kegg/legal.html
  4. Natural Product Activity and Species Source (NPASS)
  5. Wikidata
    carbapenem biosynthesis intermediate 1
    https://www.wikidata.org/wiki/Q27225525
  6. PubChem
  7. MolGenie
    MolGenie Organic Chemistry Ontology
    https://github.com/MolGenie/ontology/
CONTENTS