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ACTIVE PHARMA INGREDIENTS

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ACTIVE PHARMA INGREDIENTS

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Chemistry

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Also known as: Maduramicin ammonium, Prinicin ammonium, Maduramycin ammonium, Cygro, 84878-61-5, 61991-54-6

Molecular Formula

C₄₇H₈₃NO₁₇

Molecular Weight

934.2 g/mol

InChI Key

WQGJEAMPBSZCIF-HKSLRPGUSA-N

Maduramicin is an antiprotozoal agent used in veterinary medicine as prophylaxis against coccidiosis. It is a naturally occurring compound which was first isolated from the actinomycete, Actinomadura rubra.

1 2D Structure

Maduramicin

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

azane;2-[(2R,3S,4S,5R,6S)-6-[(1R)-1-[(2S,5R,7S,8R,9S)-2-[(2R,5S)-5-[(2R,3S,5R)-3-[(2R,4S,5S,6S)-4,5-dimethoxy-6-methyloxan-2-yl]oxy-5-[(2S,3S,5R,6S)-6-hydroxy-3,5,6-trimethyloxan-2-yl]oxolan-2-yl]-5-methyloxolan-2-yl]-7-hydroxy-2,8-dimethyl-1,10-dioxaspiro[4.5]decan-9-yl]ethyl]-2-hydroxy-4,5-dimethoxy-3-methyloxan-2-yl]acetic acid

2.1.2 InChI

InChI=1S/C47H80O17.H3N/c1-23-18-24(2)45(9,51)61-36(23)31-19-32(58-35-20-30(53-10)40(55-12)28(6)57-35)42(59-31)44(8)15-14-33(60-44)43(7)16-17-46(64-43)21-29(48)25(3)37(62-46)26(4)38-41(56-13)39(54-11)27(5)47(52,63-38)22-34(49)50;/h23-33,35-42,48,51-52H,14-22H2,1-13H3,(H,49,50);1H3/t23-,24+,25+,26+,27-,28-,29-,30-,31+,32-,33+,35+,36-,37-,38-,39-,40-,41-,42+,43-,44-,45-,46+,47+;/m0./s1

2.1.3 InChI Key

WQGJEAMPBSZCIF-HKSLRPGUSA-N

2.1.4 Canonical SMILES

CC1CC(C(OC1C2CC(C(O2)C3(CCC(O3)C4(CCC5(O4)CC(C(C(O5)C(C)C6C(C(C(C(O6)(CC(=O)O)O)C)OC)OC)C)O)C)C)OC7CC(C(C(O7)C)OC)OC)(C)O)C.N

2.1.5 Isomeric SMILES

C[C@H]1C[C@H]([C@@](O[C@@H]1[C@H]2C[C@@H]([C@@H](O2)[C@@]3(CC[C@@H](O3)[C@@]4(CC[C@@]5(O4)C[C@@H]([C@H]([C@H](O5)[C@@H](C)[C@H]6[C@@H]([C@H]([C@@H]([C@](O6)(CC(=O)O)O)C)OC)OC)C)O)C)C)O[C@@H]7C[C@@H]([C@H]([C@@H](O7)C)OC)OC)(C)O)C.N

2.2 Synonyms

2.2.1 MeSH Synonyms

1. Maduramycin

2.2.2 Depositor-Supplied Synonyms

1. Maduramicin Ammonium

2. Prinicin Ammonium

3. Maduramycin Ammonium

4. Cygro

5. 84878-61-5

6. 61991-54-6

7. Maduramycin

8. Unii-5u912u22t2

9. Maduramicin (ammonium)

10. Azane;2-[(2r,3s,4s,5r,6s)-6-[(1r)-1-[(2s,5r,7s,8r,9s)-2-[(2r,5s)-5-[(2r,3s,5r)-3-[(2r,4s,5s,6s)-4,5-dimethoxy-6-methyloxan-2-yl]oxy-5-[(2s,3s,5r,6s)-6-hydroxy-3,5,6-trimethyloxan-2-yl]oxolan-2-yl]-5-methyloxolan-2-yl]-7-hydroxy-2,8-dimethyl-1,10-dioxaspiro[4.5]decan-9-yl]ethyl]-2-hydroxy-4,5-dimethoxy-3-methyloxan-2-yl]acetic Acid

11. Cl-259971

12. Cl 273,703

13. Kaduramicina

14. Maduramicine

15. Maduramicinum

16. Maduramicine [french]

17. Maduramicinum [latin]

18. Kaduramicina [spanish]

19. 5u912u22t2

20. Cl-273703

21. Maduramicin [usan:inn:ban]

22. Cl 259971

23. Maduramicin Alpha-monoammonium Salt

24. Azane;2-[(2r,3s,4s,5r,6s)-6-[(1r)-1-[(2s,5r,7s,8r,9s)-2-[(2r,5s)-5-[(2r,3s,5r)-3-[(2r,4s,5s,6s)-4,5-dimethoxy-6-methyloxan-2-yl]oxy-5-[(2s,3s,5r,6s)-6-hydroxy-3,5,6-trimethyloxan-2-yl]oxolan-2-yl]-5-m

25. Ethyloxolan-2-yl]-7-hydroxy-2,8-dimethyl-1,10-dioxaspiro[4.5]decan-9-yl]ethyl]-2-hydroxy-4,5-dimethoxy-3-methyloxan-2-yl]acetic Acid

26. Maduramicin (usan/inn)

27. Chembl2105807

28. Hy-n7071a

29. Chebi:189929

30. S5094

31. Akos037649392

32. Db11525

33. Bs-18177

34. Cs-0085591

35. D04830

36. 878m615

37. Maduramicin Ammonium 100 Microg/ml In Acetonitrile

38. Q23936401

39. 2h-pyran-2-acetic Acid, 6-((1r)-1-((2s,5r,7s,8r,9s)-2-((2s,2'r,3's,5r,5'r)-3'-((2,6-dideoxy-3,4-di-o-methyl-beta-l-arabino-hexopyranosyl)oxy)octahydro-2-methyl-5'-((2s,3s,5r,6s)-tetrahydro-6-hydroxy-2,8-dimethyl-1,6-dioxaspiro(4.5)dec-7-yl)ethyl)tetrahydro-2-hydroxy-4,5-dimethoxy-3-methyl-, Monoammonium Salt, (2r,3s,4s,5r,6s)-

40. Lonomycin A, 23,27-didemethoxy-2,6,22-tridemethyl-11-o-demethyl-22-((2,6-dideoxy-3,4-di-o-methyl-beta-l-arabino-hexopyranosyl)oxy)-6-methoxy-, Monoammonium Salt, (3r,4s,5s,6r,7s,22s)-

2.3 Create Date

2005-08-08

3 Chemical and Physical Properties

Molecular Formula	C₄₇H₈₃NO₁₇
Molecular Weight	934.2 g/mol
Hydrogen Bond Donor Count	5
Hydrogen Bond Acceptor Count	18
Rotatable Bond Count	13
Exact Mass	933.56610018 g/mol
Monoisotopic Mass	933.56610018 g/mol
Topological Polar Surface Area	210 Å²
Heavy Atom Count	65
Formal Charge	0
Complexity	1610
Isotope Atom Count	0
Defined Atom Stereocenter Count	24
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	2