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Chemistry

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Also known as: Neomycin a, 3947-65-7, Negamicin, Nebramycin x, Dekamycin v, Neamin

Molecular Formula

C₁₂H₂₆N₄O₆

Molecular Weight

322.36 g/mol

InChI Key

SYJXFKPQNSDJLI-HKEUSBCWSA-N

FDA UNII

5981U00LY0

Neamine is the minor component of the neomycin complex, a broad spectrum aminoglycoside antibiotic derived from Streptomyces fradiae with antibacterial activity.

1 2D Structure

Neamine

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(2R,3S,4R,5R,6R)-5-amino-2-(aminomethyl)-6-[(1R,2R,3S,4R,6S)-4,6-diamino-2,3-dihydroxycyclohexyl]oxyoxane-3,4-diol

2.1.2 InChI

InChI=1S/C12H26N4O6/c13-2-5-8(18)9(19)6(16)12(21-5)22-11-4(15)1-3(14)7(17)10(11)20/h3-12,17-20H,1-2,13-16H2/t3-,4+,5-,6-,7+,8-,9-,10-,11-,12-/m1/s1

2.1.3 InChI Key

SYJXFKPQNSDJLI-HKEUSBCWSA-N

2.1.4 Canonical SMILES

C1C(C(C(C(C1N)OC2C(C(C(C(O2)CN)O)O)N)O)O)N

2.1.5 Isomeric SMILES

C1[C@H]([C@@H]([C@H]([C@@H]([C@H]1N)O[C@@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CN)O)O)N)O)O)N

2.2 Other Identifiers

2.2.1 UNII

5981U00LY0

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Neamin

2. Neomycin A

2.3.2 Depositor-Supplied Synonyms

1. Neomycin A

2. 3947-65-7

3. Negamicin

4. Nebramycin X

5. Dekamycin V

6. Neamin

7. 4-o-(2,6-diamino-2,6-dideoxy-alpha-d-glucopyranosyl)-2-deoxy-d-streptamine

8. 2-desoxy-4-o-(2,6-diamino-2,6-didesoxy-alpha-d-glucopyranosyl)-d-streptamin

9. Chebi:7489

10. (1r,2r,3s,4r,6s)-4,6-diamino-2,3-dihydroxycyclohexyl 2,6-diamino-2,6-dideoxy-alpha-d-glucopyranoside

11. (2r,3s,4r,5r,6r)-5-amino-2-(aminomethyl)-6-(((1r,2r,3s,4r,6s)-4,6-diamino-2,3-dihydroxycyclohexyl)oxy)tetrahydro-2h-pyran-3,4-diol

12. 5981u00ly0

13. (2r,3s,4r,5r,6r)-5-amino-2-(aminomethyl)-6-[(1r,2r,3s,4r,6s)-4,6-diamino-2,3-dihydroxycyclohexyl]oxyoxane-3,4-diol

14. (1r,3s,3s,5r,6r)-5-amino-2-aminomethyl-6-(4,6-diamino-2,3-dihydroxy-cyclohexyloxy)-tetrahydro-pyran-3,4-diol

15. (2r,3s,4r,5r,6r)-5-amino-2-(aminomethyl)-6-[(1r,2r,3s,4r,6s)-4,6-diamino-2,3-dihydroxy-cyclohexoxy]tetrahydropyran-3,4-diol

16. (2r,3s,4r,5r,6r)-6-((1r,2r,3s,4r,6s)-4,6-diamino-2,3-dihydroxycyclohexyloxy)-5-amino-2-(aminomethyl)-tetrahydro-2h-pyran-3,4-diol

17. Xxx

18. Brn 0026714

19. Unii-5981u00ly0

20. Neamine [mi]

21. D-streptamine, 2-deoxy-4-o-(2,6-diamino-2,6-dideoxy-alpha-d-glucopyranosyl)-

22. (+)-neamine

23. 4-18-00-07474 (beilstein Handbook Reference)

24. Schembl219578

25. Bdbm8580

26. Chembl427409

27. St 7

28. Dtxsid7023358

29. Hy-n7449

30. Zinc4095654

31. Mfcd00023857

32. Akos025311197

33. Db04808

34. D-streptamine, 2-deoxy-4-o-(2,6-diamino-2,6-dideoxy-.alpha.-d-glucopyranosyl)-

35. Neomycin Sulfate Ep Impurity A (neamine)

36. Tobramycin Impurity C [ep Impurity]

37. Cs-0129171

38. C01441

39. 947n657

40. A824565

41. Neomycin Sulfate Impurity A [ep Impurity]

42. Q6984256

43. 2-deoxy-4-o-(2,6-diamine-2,6-dideoxy-.alpha.-d-glucopyranosyl)-d-streptamine

44. (2r,3s,4r,5r,6r)-5-amino-2-(aminomethyl)-6-(((1r,2r,3s,4r,6s)-4,6-diamino-2,3-dihydroxycyclohexyl)oxy)tetrahydro-2h-pyran-3,4-diol Hydrochloride

45. (2r,3s,4r,5r,6r)-5-amino-2-(aminomethyl)-6-((1r,2r,3s,4r,6s)-4,6-diamino-2,3-dihydroxycyclohexyloxy)-tetrahydro-2h-pyran-3,4-diol

46. (2r,3s,4r,5r,6r)-5-amino-2-(aminomethyl)-6-((1r,2r,3s,4r,6s)-4,6-diamino-2,3-dihydroxycyclohexyloxy)tetrahydro-2h-pyran-3,4-diol

47. (2r,3s,4r,5r,6r)-5-amino-2-(aminomethyl)-6-{[(1r,2r,3s,4r,6s)-4,6-diamino-2,3-dihydroxycyclohexyl]oxy}oxane-3,4-diol

48. O-2,6-diamino-2,6-dideoxy-.alpha.-d-glucopyranosyl-(1->4)-1,3-diamino-1,2,3-trideoxy-d-myo-inositol

49. Wurcs=2.0/1,1,0/[a2122h-1a_1-5_1*oc^rc^rc^sc^rcc^s$3/8n/6n/5o/4o_2*n_6*n]/1/

2.4 Create Date

2005-06-24

3 Chemical and Physical Properties

Molecular Formula	C₁₂H₂₆N₄O₆
Molecular Weight	322.36 g/mol
XLogP3	-5.4
Hydrogen Bond Donor Count	8
Hydrogen Bond Acceptor Count	10
Rotatable Bond Count	3
Exact Mass	322.18523456 g/mol
Monoisotopic Mass	322.18523456 g/mol
Topological Polar Surface Area	204 Å²
Heavy Atom Count	22
Formal Charge	0
Complexity	378
Isotope Atom Count	0
Defined Atom Stereocenter Count	10
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

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Neamine

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ACTIVE PHARMA INGREDIENTS

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ACTIVE PHARMA INGREDIENTS

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$ 7

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