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Chemistry

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Also known as: Dihydrostreptomycin sesquisulfate, 5490-27-7, Dihydrostreptomycin sulphate, Dihydrostreptomycin sulfate [usp], Dihydrostreptomycin sulfate (2:3)(salt), T7d4876iue

Molecular Formula

C₄₂H₈₈N₁₄O₃₆S₃

Molecular Weight

1461.4 g/mol

InChI Key

CZWJCQXZZJHHRH-YCRXJPFRSA-N

FDA UNII

T7D4876IUE

A semi-synthetic aminoglycoside antibiotic that is used in the treatment of TUBERCULOSIS.

1 2D Structure

Dihydrostreptomycin sulfate

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

2-[(1R,2R,3S,4R,5R,6S)-3-(diaminomethylideneamino)-4-[(2R,3R,4R,5S)-3-[(2S,3S,4S,5R,6S)-4,5-dihydroxy-6-(hydroxymethyl)-3-(methylamino)oxan-2-yl]oxy-4-hydroxy-4-(hydroxymethyl)-5-methyloxolan-2-yl]oxy-2,5,6-trihydroxycyclohexyl]guanidine;sulfuric acid

2.1.2 InChI

InChI=1S/2C21H41N7O12.3H2O4S/c2*1-5-21(36,4-30)16(40-17-9(26-2)13(34)10(31)6(3-29)38-17)18(37-5)39-15-8(28-20(24)25)11(32)7(27-19(22)23)12(33)14(15)35;3*1-5(2,3)4/h2*5-18,26,29-36H,3-4H2,1-2H3,(H4,22,23,27)(H4,24,25,28);3*(H2,1,2,3,4)/t2*5-,6-,7+,8-,9-,10-,11+,12-,13-,14+,15+,16-,17-,18-,21+;;;/m00.../s1

2.1.3 InChI Key

CZWJCQXZZJHHRH-YCRXJPFRSA-N

2.1.4 Canonical SMILES

CC1C(C(C(O1)OC2C(C(C(C(C2O)O)N=C(N)N)O)N=C(N)N)OC3C(C(C(C(O3)CO)O)O)NC)(CO)O.CC1C(C(C(O1)OC2C(C(C(C(C2O)O)N=C(N)N)O)N=C(N)N)OC3C(C(C(C(O3)CO)O)O)NC)(CO)O.OS(=O)(=O)O.OS(=O)(=O)O.OS(=O)(=O)O

2.1.5 Isomeric SMILES

C[C@H]1[C@@]([C@H]([C@@H](O1)O[C@@H]2[C@H]([C@@H]([C@H]([C@@H]([C@H]2O)O)N=C(N)N)O)N=C(N)N)O[C@H]3[C@H]([C@@H]([C@H]([C@@H](O3)CO)O)O)NC)(CO)O.C[C@H]1[C@@]([C@H]([C@@H](O1)O[C@@H]2[C@H]([C@@H]([C@H]([C@@H]([C@H]2O)O)N=C(N)N)O)N=C(N)N)O[C@H]3[C@H]([C@@H]([C@H]([C@@H](O3)CO)O)O)NC)(CO)O.OS(=O)(=O)O.OS(=O)(=O)O.OS(=O)(=O)O

2.2 Other Identifiers

2.2.1 UNII

T7D4876IUE

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Citrocil

2. Dihydrostreptomycin

3. Sulfate, Dihydrostreptomycin

2.3.2 Depositor-Supplied Synonyms

1. Dihydrostreptomycin Sesquisulfate

2. 5490-27-7

3. Dihydrostreptomycin Sulphate

4. Dihydrostreptomycin Sulfate [usp]

5. Dihydrostreptomycin Sulfate (2:3)(salt)

6. T7d4876iue

7. Didromycin

8. Nsc-756739

9. Didromycine

10. Panstreptin

11. 2-[(1r,2r,3s,4r,5r,6s)-3-(diaminomethylideneamino)-4-[(2r,3r,4r,5s)-3-[(2s,3s,4s,5r,6s)-4,5-dihydroxy-6-(hydroxymethyl)-3-(methylamino)oxan-2-yl]oxy-4-hydroxy-4-(hydroxymethyl)-5-methyloxolan-2-yl]oxy-2,5,6-trihydroxycyclohexyl]guanidine;sulfuric Acid

12. Dihydrostreptomycin Sulfate (usp)

13. Hydroxycyclohexyl]guanidine;sulfuric Acid

14. Dihydrostreptomycin 3/2 Sulfate

15. Dihydrostreptomyzinsulfat

16. Einecs 226-823-7

17. Unii-t7d4876iue

18. Ai3-50133

19. Dihydrostreptomycin Sequisulphate

20. Dihydrostreptomycinium Sulfuricum

21. 1-[(1r,2r,3s,4r,5r,6s)-3-carbamimidamido-4-[(2r,3r,4r,5s)-3-[(2s,3s,4s,5r,6s)-4,5-dihydroxy-6-(hydroxymethyl)-3-(methylamino)oxan-2-yl]oxy-4-hydroxy-4-(hydroxymethyl)-5-methyloxolan-2-yl]oxy-2,5,6-tri

22. Ncgc00094655-01

23. Cas-5490-27-7

24. Dsstox_cid_25824

25. Dsstox_rid_81155

26. Dsstox_gsid_45824

27. Chembl3188576

28. Dtxsid6045824

29. Tox21_111309

30. Mfcd00070252

31. Akos026750384

32. Akos037515800

33. D-streptamine, O-2-deoxy-2-(methylamino)-.alpha.-l-glucopyranosyl-(1.fwdarw.2)-o-5-deoxy-3-c-(hydroxymethyl)-.alpha.-l-lyxofuranosyl-(1.fwdarw.4)-n,n'-bis(aminoiminomethyl)-, Sulfate (2:3) (salt)

34. D-streptamine, O-2-deoxy-2-(methylamino)-alpha-l-glucopyranosyl-(1-2)-o-5-deoxy-3-c-(hydroxymethyl)-alpha-l-lyxofuranosyl-(1-4)-n,n'-bis(aminoiminomethyl)-, Sulfate (2:3) (salt)

35. Dihydrostreptomycin Sulfate [mart.]

36. Dihydrostreptomycin Sulfate [usp-rs]

37. Dihydrostreptomycin Sulfate [who-dd]

38. Dihydrostreptomycin Sesquisulfate [mi]

39. 1425-61-2

40. D02512

41. Dihydrostreptomycin Sulfate [green Book]

42. Dihydrostreptomycin Sulfate [usp Monograph]

43. Dihydrostreptomycin Sulphate (2:3)(salt)

44. W-105598

45. Q27289765

46. Dihydrostreptomycin Sulfate, Antibiotic For Culture Media Use Only

47. 1,1'-((1r,2r,3s,4r,5r,6s)-4-(((2r,3r,4r,5s)-3-(((2s,3s,4s,5r,6s)-4,5-dihydroxy-6-(hydroxymethyl)-3-(methylamino)tetrahydro-2h-pyran-2-yl)oxy)-4-hydroxy-4-(hydroxymethyl)-5-methyltetrahydrofuran-2-yl)oxy)-2,5,6-trihydroxycyclohexane-1,3-diyl)diguanidine Sesquisulfate

48. D-streptamine, O-2-deoxy-2-(methylamino)-alpha-l-glucopyranosyl-(1->2)-o-5-deoxy-3-c-(hydroxymethyl)-alpha-l-lyxofuranosyl-(1->4)-n1,n3-bis(aminoiminomethyl)-, Sulfate (2:3)

49. D-streptamine, O-2-deoxy-2-(methylamino)-alpha-l-glucopyranosyl-(1.fwdarw.2)-o-5-deoxy-3-c-(hydroxymethyl)-alpha-l-lyxofuranosyl-(1.fwdarw.4)-n,n'-bis(aminoiminomethyl)-, Sulfate (2:3) (salt)

2.4 Create Date

2005-08-08

3 Chemical and Physical Properties

Molecular Formula	C₄₂H₈₈N₁₄O₃₆S₃
Molecular Weight	1461.4 g/mol
Hydrogen Bond Donor Count	32
Hydrogen Bond Acceptor Count	42
Rotatable Bond Count	18
Exact Mass	1460.4647787 g/mol
Monoisotopic Mass	1460.4647787 g/mol
Topological Polar Surface Area	928 Å²
Heavy Atom Count	95
Formal Charge	0
Complexity	993
Isotope Atom Count	0
Defined Atom Stereocenter Count	30
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	5