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Chemistry

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Also known as: 4052-54-4, Benzylpenicillin r-sulfoxide, Penicillin sulfoxide, 52248-38-1, [2s-(2alpha,5alpha,6beta)]-3,3-dimethyl-7-oxo-6-(phenylacetamido)-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid 4-oxide, (2s,5r,6r)-3,3-dimethyl-4,7-dioxo-6-[(2-phenylacetyl)amino]-4lambda4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
Molecular Formula
C16H18N2O5S
Molecular Weight
350.4  g/mol
InChI Key
FCZNNHHXCFARDY-WQRUCBPWSA-N

Penicillin G Sulfoxide
1 2D Structure

Penicillin G Sulfoxide

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
(2S,5R,6R)-3,3-dimethyl-4,7-dioxo-6-[(2-phenylacetyl)amino]-44-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
2.1.2 InChI
InChI=1S/C16H18N2O5S/c1-16(2)12(15(21)22)18-13(20)11(14(18)24(16)23)17-10(19)8-9-6-4-3-5-7-9/h3-7,11-12,14H,8H2,1-2H3,(H,17,19)(H,21,22)/t11-,12+,14-,24?/m1/s1
2.1.3 InChI Key
FCZNNHHXCFARDY-WQRUCBPWSA-N
2.1.4 Canonical SMILES
CC1(C(N2C(S1=O)C(C2=O)NC(=O)CC3=CC=CC=C3)C(=O)O)C
2.1.5 Isomeric SMILES
CC1([C@@H](N2[C@H](S1=O)[C@@H](C2=O)NC(=O)CC3=CC=CC=C3)C(=O)O)C
2.2 Synonyms
2.2.1 MeSH Synonyms

1. Penicillin G Sulfoxide, (4beta)-isomer

2. Penicillin G Sulfoxide, Monosodium Salt

3. Penicillin G-sulfoxide

2.2.2 Depositor-Supplied Synonyms

1. 4052-54-4

2. Benzylpenicillin R-sulfoxide

3. Penicillin Sulfoxide

4. 52248-38-1

5. [2s-(2alpha,5alpha,6beta)]-3,3-dimethyl-7-oxo-6-(phenylacetamido)-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic Acid 4-oxide

6. (2s,5r,6r)-3,3-dimethyl-4,7-dioxo-6-[(2-phenylacetyl)amino]-4lambda4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic Acid

7. Benzylpenicillin S-sulfoxide

8. (2s-(2alpha,5alpha,6beta))-3,3-dimethyl-7-oxo-6-(phenylacetamido)-4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylic Acid 4-oxide

9. Einecs 223-757-0

10. Einecs 251-828-6

11. Einecs 257-786-5

12. 6beta-phenylacetamidopenicillanic Acid 1beta-oxide

13. Chembl323646

14. Schembl9280462

15. Dtxsid801105936

16. (2s-(2alpha,4alpha,5alpha,6beta))-3,3-dimethyl-7-oxo-6-(phenylacetamido)-4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylic Acid 4-oxide

17. (2s-(2alpha,4beta,5alpha,6beta))-3,3-dimethyl-7-oxo-6-(phenylacetamido)-4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylic Acid 4-oxide

18. W-109214

19. W-109940

20. [2s-(2,4,5,6)]-3,3-dimethyl-7-oxo-6-(phenylacetamido)-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic Acid 4-oxide

21. [2s-(2,5,6)]-3,3-dimethyl-7-oxo-6-(phenylacetamido)-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic Acid 4-oxide

22. 4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic Acid, 3,3-dimethyl-7-oxo-6-[(phenylacetyl)amino]- (2s,5r,6r)-, 4-oxide

2.3 Create Date
2005-06-24
3 Chemical and Physical Properties
Molecular Weight 350.4 g/mol
Molecular Formula C16H18N2O5S
XLogP30.7
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count6
Rotatable Bond Count4
Exact Mass350.09364285 g/mol
Monoisotopic Mass350.09364285 g/mol
Topological Polar Surface Area123 Ų
Heavy Atom Count24
Formal Charge0
Complexity599
Isotope Atom Count0
Defined Atom Stereocenter Count3
Undefined Atom Stereocenter Count1
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1

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