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Chemistry

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Also known as: 157-03-9, Diazooxonorleucine, L-don, L-norleucine, 6-diazo-5-oxo-, 6-diazo-5-oxo-l-nor-leucine, L-6-diazo-5-oxonorleucine
Molecular Formula
C6H9N3O3
Molecular Weight
171.15  g/mol
InChI Key
YCWQAMGASJSUIP-YFKPBYRVSA-N
FDA UNII
03J0H273KZ

6-Diazo-5-oxo-L-norleucine
An amino acid that inhibits phosphate-activated glutaminase and interferes with glutamine metabolism. It is an antineoplastic antibiotic produced by an unidentified species of Streptomyces from Peruvian soil. (From Merck Index, 11th ed)
1 2D Structure

6-Diazo-5-oxo-L-norleucine

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
(2S)-2-amino-6-diazo-5-oxohexanoic acid
2.1.2 InChI
InChI=1S/C6H9N3O3/c7-5(6(11)12)2-1-4(10)3-9-8/h3,5H,1-2,7H2,(H,11,12)/t5-/m0/s1
2.1.3 InChI Key
YCWQAMGASJSUIP-YFKPBYRVSA-N
2.1.4 Canonical SMILES
C(CC(=O)C=[N+]=[N-])C(C(=O)O)N
2.1.5 Isomeric SMILES
C(CC(=O)C=[N+]=[N-])[C@@H](C(=O)O)N
2.2 Other Identifiers
2.2.1 UNII
03J0H273KZ
2.3 Synonyms
2.3.1 MeSH Synonyms

1. 6 Diazo 5 Oxo L Norleucine

2. Diazooxonorleucine

2.3.2 Depositor-Supplied Synonyms

1. 157-03-9

2. Diazooxonorleucine

3. L-don

4. L-norleucine, 6-diazo-5-oxo-

5. 6-diazo-5-oxo-l-nor-leucine

6. L-6-diazo-5-oxonorleucine

7. L-norleucine,6-diazo-5-oxo-

8. Don

9. Nsc-7365

10. 03j0h273kz

11. Don (pharmaceutical)

12. Mfcd00037218

13. Nsc 7365

14. Brn 1725815

15. Norleucine,6-diazo-5-oxo-

16. Nsc7365

17. (s)-2-amino-6-diazo-5-oxocaproic Acid

18. Unii-03j0h273kz

19. Ai3-26441

20. Norleucine, 6-diazo-5-oxo, L-

21. Ncimech_000302

22. Ncistruc1_000220

23. Ncistruc2_000175

24. (l)-don

25. 4-04-00-03278 (beilstein Handbook Reference)

26. Chembl97485

27. Chembl4303391

28. Diazo-5-oxo-l-norleucine, 6-

29. Schembl15349013

30. Schembl15349015

31. Kmx-010

32. Nci7365

33. Chebi:138889

34. Dtxsid501028846

35. Ex-a1965

36. Zinc3953825

37. Ccg-35449

38. Ccg-37571

39. Ncgc00013078

40. Akos030213039

41. Ncgc00013078-02

42. Ncgc00096202-01

43. 6-diazo-5-oxo-l-norleucine, Crystalline

44. 6-diazo-5-oxo-l-norleucine [mi]

45. (2s)-2-amino-6-diazo-5-oxohexanoic Acid

46. Hy-108357

47. (2s)-2-amino-6-diazo-5-oxo-hexanoic Acid

48. Cs-0028442

49. A936514

50. Q245487

51. J-009370

2.4 Create Date
2005-08-01
3 Chemical and Physical Properties
Molecular Weight 171.15 g/mol
Molecular Formula C6H9N3O3
XLogP3-3.5
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count5
Rotatable Bond Count5
Exact Mass171.06439116 g/mol
Monoisotopic Mass171.06439116 g/mol
Topological Polar Surface Area82.4 Ų
Heavy Atom Count12
Formal Charge0
Complexity232
Isotope Atom Count0
Defined Atom Stereocenter Count1
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count1
Covalently Bonded Unit Count1
4 Pharmacology and Biochemistry
4.1 MeSH Pharmacological Classification

Antimetabolites, Antineoplastic

Antimetabolites that are useful in cancer chemotherapy. (See all compounds classified as Antimetabolites, Antineoplastic.)


Antibiotics, Antineoplastic

Chemical substances, produced by microorganisms, inhibiting or preventing the proliferation of neoplasms. (See all compounds classified as Antibiotics, Antineoplastic.)


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