CAS 63358-49-6

Chemistry

Chemistry

Also known as: 63358-49-6, Aspoxicillan, Aspoxicilina, Aspoxicilline, Aspoxicillinum, Aspc

Molecular Formula

C₂₁H₂₇N₅O₇S

Molecular Weight

493.5 g/mol

InChI Key

BHELIUBJHYAEDK-OAIUPTLZSA-N

FDA UNII

0745KNO26J

Aspoxicillin is a broad-spectrum, semisynthetic penicillin derivative with antibacterial activity. Aspoxicillin binds to and inactivates penicillin-binding proteins (PBPs) located on the inner membrane of the bacterial cell wall. Inactivation of PBPs interferes with the cross-linkage of peptidoglycan chains necessary for bacterial cell wall strength and rigidity. This interrupts bacterial cell wall synthesis and results in the weakening of the bacterial cell wall, eventually causing cell lysis.

1 2D Structure

CAS 63358-49-6

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(2S,5R,6R)-6-[[(2R)-2-[[(2R)-2-amino-4-(methylamino)-4-oxobutanoyl]amino]-2-(4-hydroxyphenyl)acetyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid

2.1.2 InChI

InChI=1S/C21H27N5O7S/c1-21(2)15(20(32)33)26-18(31)14(19(26)34-21)25-17(30)13(9-4-6-10(27)7-5-9)24-16(29)11(22)8-12(28)23-3/h4-7,11,13-15,19,27H,8,22H2,1-3H3,(H,23,28)(H,24,29)(H,25,30)(H,32,33)/t11-,13-,14-,15+,19-/m1/s1

2.1.3 InChI Key

BHELIUBJHYAEDK-OAIUPTLZSA-N

2.1.4 Canonical SMILES

CC1(C(N2C(S1)C(C2=O)NC(=O)C(C3=CC=C(C=C3)O)NC(=O)C(CC(=O)NC)N)C(=O)O)C

2.1.5 Isomeric SMILES

CC1([C@@H](N2[C@H](S1)[C@@H](C2=O)NC(=O)[C@@H](C3=CC=C(C=C3)O)NC(=O)[C@@H](CC(=O)NC)N)C(=O)O)C

2.2 Other Identifiers

2.2.1 UNII

0745KNO26J

2.3 Synonyms

2.3.1 MeSH Synonyms

1. N(4)-methyl-d-asparaginylamoxicillin

2. Ta 058

3. Ta-058

2.3.2 Depositor-Supplied Synonyms

1. 63358-49-6

2. Aspoxicillan

3. Aspoxicilina

4. Aspoxicilline

5. Aspoxicillinum

6. Aspc

7. Doyle

8. Doyle (tn)

9. (2s,5r,6r)-6-[[(2r)-2-[[(2r)-2-amino-4-(methylamino)-4-oxobutanoyl]amino]-2-(4-hydroxyphenyl)acetyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic Acid

10. Chebi:31240

11. 0745kno26j

12. Ncgc00181352-01

13. (2s,5r,6r)-6-((2r)-2-((2r)-2-amino-3-(methylcarbamoyl)propionamido)-2-(p-hydroxyphenyl)acetamido)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylic Acid

14. Aspoxicilina [spanish]

15. Aspoxicilline [french]

16. Aspoxicillinum [latin]

17. Aspoxicillin [inn:jan]

18. Ta 058

19. Ccris 2514

20. Unii-0745kno26j

21. N(sup 4)-methyl-d-asparagininylamoxicillin

22. Aspoxicillin (jan/inn)

23. Aspoxicillin [mi]

24. Aspoxicillin [inn]

25. Dsstox_cid_26921

26. Dsstox_rid_82017

27. Dsstox_gsid_46921

28. Schembl34176

29. Aspoxicillin [mart.]

30. Aspoxicillin [who-dd]

31. Chembl1318150

32. Dtxsid6046921

33. Zinc3871610

34. Tox21_112810

35. Db13816

36. Glycinamide, N-methyl-d-asparaginyl-n-(2-carboxy-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo(3.2.0)hept-6-yl)-d-2-(4-hydroxyphenyl)-, (2s-(2-alpha,5-alpha,6-beta))-

37. Cas-63358-49-6

38. Hy-135842

39. Cs-0114376

40. D07469

41. Q27114235

42. (2s,5r,6r)-6-[[(2r)-2-[[(2r)-2-amino-4-(methylamino)-4-oxo-butanoyl]amino]-2-(4-hydroxyphenyl)acetyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic Acid

43. (2s,5r,6r)-6-[[(2r)-2-[[(2r)-2-amino-4-methylamino-4-oxobutanoyl]amino]-2-(4-hydroxyphenyl)acetyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic Acid

2.4 Create Date

2005-06-24

3 Chemical and Physical Properties

Molecular Formula	C₂₁H₂₇N₅O₇S
Molecular Weight	493.5 g/mol
XLogP3	-3.4
Hydrogen Bond Donor Count	6
Hydrogen Bond Acceptor Count	9
Rotatable Bond Count	8
Exact Mass	493.16311939 g/mol
Monoisotopic Mass	493.16311939 g/mol
Topological Polar Surface Area	217 Å²
Heavy Atom Count	34
Formal Charge	0
Complexity	861
Isotope Atom Count	0
Defined Atom Stereocenter Count	5
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1