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Chemistry

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Also known as: Miocamycin, Acecamycin, Miokamycin, Ponsinomycin, 3'',9-diacetylmydecamycin, 55881-07-7

Molecular Formula

C₄₅H₇₁NO₁₇

Molecular Weight

898.0 g/mol

InChI Key

GQNZGCARKRHPOH-RQIKCTSVSA-N

FDA UNII

3T48CPS7U2

Miocamycin is a macrolide type antimicrobial. This drug may be marketed in Japan for clinical use as it is listed in the Japanese pharmacopeia. It has shown to be effective against several gram-positive and gram-negative microbes and may be useful in the treatment of upper and lower respiratory tract infections, and urogenital tract infections or as an alternative to erythromycin treatment.

1 2D Structure

Miocamycin

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

[(4R,5S,6S,7R,9R,10R,11E,13E,16R)-10-acetyloxy-6-[(2S,3R,4R,5S,6R)-5-[(2S,4R,5S,6S)-4-acetyloxy-4,6-dimethyl-5-propanoyloxyoxan-2-yl]oxy-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-5-methoxy-9,16-dimethyl-2-oxo-7-(2-oxoethyl)-1-oxacyclohexadeca-11,13-dien-4-yl] propanoate

2.1.2 InChI

InChI=1S/C45H71NO17/c1-13-34(50)59-33-23-36(52)55-26(4)18-16-15-17-19-32(58-29(7)48)25(3)22-31(20-21-47)41(42(33)54-12)62-44-39(53)38(46(10)11)40(27(5)57-44)61-37-24-45(9,63-30(8)49)43(28(6)56-37)60-35(51)14-2/h15-17,19,21,25-28,31-33,37-44,53H,13-14,18,20,22-24H2,1-12H3/b16-15+,19-17+/t25-,26-,27-,28+,31+,32+,33-,37+,38-,39-,40-,41+,42+,43+,44+,45-/m1/s1

2.1.3 InChI Key

GQNZGCARKRHPOH-RQIKCTSVSA-N

2.1.4 Canonical SMILES

CCC(=O)OC1CC(=O)OC(CC=CC=CC(C(CC(C(C1OC)OC2C(C(C(C(O2)C)OC3CC(C(C(O3)C)OC(=O)CC)(C)OC(=O)C)N(C)C)O)CC=O)C)OC(=O)C)C

2.1.5 Isomeric SMILES

CCC(=O)O[C@@H]1CC(=O)O[C@@H](C/C=C/C=C/[C@@H]([C@@H](C[C@@H]([C@@H]([C@H]1OC)O[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)C)O[C@H]3C[C@@]([C@H]([C@@H](O3)C)OC(=O)CC)(C)OC(=O)C)N(C)C)O)CC=O)C)OC(=O)C)C

2.2 Other Identifiers

2.2.1 UNII

3T48CPS7U2

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Maidimeisu

2. Midecamin

3. Midecamycin

4. Midecamycin Diacetate

5. Midekamycin

6. Midekamycin Acetate

7. Mosil

8. Mydecamycin

9. Myoxam

10. Neoisomidecamycin

11. Normicina

12. Sf 837

13. Sf-837

2.3.2 Depositor-Supplied Synonyms

1. Miocamycin

2. Acecamycin

3. Miokamycin

4. Ponsinomycin

5. 3'',9-diacetylmydecamycin

6. 55881-07-7

7. Midecamycin Acetate [jan]

8. Midecamycin Diacetate

9. 9,3''-di-o-acetylmidecamycin

10. Leucomycin V, 3b,9-diacetate 3,4b-dipropanoate

11. 3t48cps7u2

12. Mom

13. [(4r,5s,6s,7r,9r,10r,11e,13e,16r)-10-acetyloxy-6-[(2s,3r,4r,5s,6r)-5-[(2s,4r,5s,6s)-4-acetyloxy-4,6-dimethyl-5-propanoyloxyoxan-2-yl]oxy-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-5-methoxy-9,16-dimethyl-2-oxo-7-(2-oxoethyl)-1-oxacyclohexadeca-11,13-dien-4-yl] Propanoate

14. 9,3''-diacetylmidecamycin

15. Einecs 259-879-6

16. Unii-3t48cps7u2

17. Macroral

18. Miocamen

19. Mosil

20. Miocamycin (tn)

21. Miocamycin [mi]

22. Midecamycin Acetate (jp17)

23. Schembl139293

24. Chembl1091024

25. Dtxsid60905087

26. Leucomycin V, 3(sup B),9-diacetate 3,4(sup B)-dipropanoate

27. Midecamycin Acetate [who-dd]

28. Zinc169677000

29. 1532-rb

30. Leucomycinv,3b,9-diacetate3,4b-dipropanoate

31. D01636

32. Q3858659

33. W-105540

34. Midecamycin Acetate, Antibiotic For Culture Media Use Only

2.4 Create Date

2005-06-24

3 Chemical and Physical Properties

Molecular Formula	C₄₅H₇₁NO₁₇
Molecular Weight	898.0 g/mol
XLogP3	3.8
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	18
Rotatable Bond Count	18
Exact Mass	897.47219980 g/mol
Monoisotopic Mass	897.47219980 g/mol
Topological Polar Surface Area	218 Å²
Heavy Atom Count	63
Formal Charge	0
Complexity	1590
Isotope Atom Count	0
Defined Atom Stereocenter Count	16
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	2
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1