Micronomicin

Synopsis, Chemistry

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Also known as: Gentamicin c2b, 52093-21-7, Sagamicin, Santemycin, Micronomicin [inn], Xk-62-2

Molecular Formula

C₂₀H₄₁N₅O₇

Molecular Weight

463.6 g/mol

InChI Key

DNYGXMICFMACRA-XHEDQWPISA-N

FDA UNII

S9AZ0R40QV

Micronomicin is an aminoglycoside antibiotic isolated from Micromonospora sagamiensis var. nonreducans. Micronomicin is an analog of gentamicin and has broad-spectrum activity against both gram-positive and gram-negative bacteria.

1 2D Structure

Micronomicin

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(2R,3R,4R,5R)-2-[(1S,2S,3R,4S,6R)-4,6-diamino-3-[(2R,3R,6S)-3-amino-6-(methylaminomethyl)oxan-2-yl]oxy-2-hydroxycyclohexyl]oxy-5-methyl-4-(methylamino)oxane-3,5-diol

2.1.2 InChI

InChI=1S/C20H41N5O7/c1-20(28)8-29-19(14(27)17(20)25-3)32-16-12(23)6-11(22)15(13(16)26)31-18-10(21)5-4-9(30-18)7-24-2/h9-19,24-28H,4-8,21-23H2,1-3H3/t9-,10+,11-,12+,13-,14+,15+,16-,17+,18+,19+,20-/m0/s1

2.1.3 InChI Key

DNYGXMICFMACRA-XHEDQWPISA-N

2.1.4 Canonical SMILES

CC1(COC(C(C1NC)O)OC2C(CC(C(C2O)OC3C(CCC(O3)CNC)N)N)N)O

2.1.5 Isomeric SMILES

C[C@@]1(CO[C@@H]([C@@H]([C@H]1NC)O)O[C@H]2[C@@H](C[C@@H]([C@H]([C@@H]2O)O[C@@H]3[C@@H](CC[C@H](O3)CNC)N)N)N)O

2.2 Other Identifiers

2.2.1 UNII

S9AZ0R40QV

2.3 Synonyms

2.3.1 MeSH Synonyms

1. 6'-n-methylgentamicin C

2. De 020

3. De-020

4. Gentamicin C2b

5. Kw 1062

6. Kw-1062

7. Sagamicin

8. Xk-62-2

2.3.2 Depositor-Supplied Synonyms

1. Gentamicin C2b

2. 52093-21-7

3. Sagamicin

4. Santemycin

5. Micronomicin [inn]

6. Xk-62-2

7. 6'-n-methylgentamicin C1a

8. S9az0r40qv

9. Chebi:81283

10. Kw-1062

11. (2r,3r,4r,5r)-2-[(1s,2s,3r,4s,6r)-4,6-diamino-3-[(2r,3r,6s)-3-amino-6-(methylaminomethyl)oxan-2-yl]oxy-2-hydroxycyclohexyl]oxy-5-methyl-4-(methylamino)oxane-3,5-diol

12. D-streptamine, O-2-amino-2,3,4,6-tetradeoxy-6-(methylamino)-alpha-d-erythro-hexopyranosyl-(1-4)-o-(3-deoxy-4-c-methyl-3-(methylamino)-beta-l-arabinopyranosyl-(1-6))-2-deoxy

13. Micromicin

14. Micromycin

15. Micronomicina

16. Micronomicine

17. Micronomicinum

18. Sagamicin (obs.)

19. Gentamicin C(sub 2b)

20. Antibiotic Kw 1062

21. Antibiotic Xk 62-2

22. Ncgc00183277-01

23. Unii-s9az0r40qv

24. Micronomicine [inn-french]

25. Micronomicinum [inn-latin]

26. Micronomicina [inn-spanish]

27. 6'-n-methylgentamicin C(sub 1a)

28. De 020

29. Micronomicin (dcf)

30. Kw 1062

31. Xk 62-2

32. Micronomicin [mi]

33. Micronomicin [who-dd]

34. Schembl147893

35. Chembl373081

36. Gtpl12162

37. Dtxsid401023736

38. Hy-b1915

39. Zinc8214612

40. Akos016010141

41. Db13274

42. Cs-0013973

43. C17706

44. D08219

45. Q6839784

46. D-streptamine, O-2-amino-6-(methylamino)-2,3,4,6-tetradeoxy-alpha-d-erythro-hexopyranosyl-(1-4)-o-(3-deoxy-4-c-methyl-3-(methylamino)-beta-l-arabinopyranosyl-(1-6))-2-deoxy-

47. O-2-amino-2,3,4,6-tetradeoxy-6-(methylamino)-.alpha.-d-erythro-hexopyranosyl-(1->4)-o-(3-deoxy-4-c-methyl-3-(methylamino)-.beta.-l-arabinopyranosyl-(1->6)-2-deoxy-d-streptamine

48. O-2-amino-2,3,4,6-tetradeoxy-6-(methylamino)-a-d-erythro-hexopyranosyl-(1->4)-o-(3-deoxy-4-c-methyl-3-(methylamino)-.beta.-l-arabinopyranosyl-(1->6))-2-deoxy-d-streptamine

49. O-2-amino-2,3,4,6-tetradeoxy-6-(methylamino)-a-d-erythro-hexopyranosyl-(1-4)-o-(3-deoxy-4-c-methyl-3-(methylamino)-beta-l-arabinopyranosyl-(1-6))-2-deoxy-d-streptamine

2.4 Create Date

2005-08-09

3 Chemical and Physical Properties

Molecular Formula	C₂₀H₄₁N₅O₇
Molecular Weight	463.6 g/mol
XLogP3	-4.5
Hydrogen Bond Donor Count	8
Hydrogen Bond Acceptor Count	12
Rotatable Bond Count	7
Exact Mass	463.30059866 g/mol
Monoisotopic Mass	463.30059866 g/mol
Topological Polar Surface Area	200 Å²
Heavy Atom Count	32
Formal Charge	0
Complexity	607
Isotope Atom Count	0
Defined Atom Stereocenter Count	12
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1