Synonym
Niddamycin; F-3463; F 3463; F3463;
IUPAC/Chemical Name
(2R,3S,4R,6S)-6-(((2R,3R,4R,5S,6S)-4-(dimethylamino)-5-hydroxy-6-(((4R,5S,6S,7R,9R,11E,13Z,16S)-4-hydroxy-5-methoxy-9,16-dimethyl-2,10-dioxo-7-(2-oxoethyl)oxacyclohexadeca-11,13-dien-6-yl)oxy)-2-methyltetrahydro-2H-pyran-3-yl)oxy)-4-hydroxy-2,4-dimethyltetrahydro-2H-pyran-3-yl 3-methylbutanoate
InChi Key
SSANHLOZXYEHCY-FYXPASJWSA-N
InChi Code
InChI=1S/C40H65NO14/c1-22(2)18-30(45)53-38-26(6)51-32(21-40(38,7)48)54-35-25(5)52-39(34(47)33(35)41(8)9)55-36-27(16-17-42)19-23(3)28(43)15-13-11-12-14-24(4)50-31(46)20-29(44)37(36)49-10/h11-13,15,17,22-27,29,32-39,44,47-48H,14,16,18-21H2,1-10H3/b12-11-,15-13+/t23-,24+,25-,26-,27+,29-,32+,33-,34+,35+,36+,37+,38+,39+,40-/m1/s1
SMILES Code
O[C@@]1(C)[C@@H](OC(CC(C)C)=O)[C@@H](C)O[C@@H](O[C@@H]2[C@H](N(C)C)[C@H](O)[C@H](O[C@@H]3[C@H]([C@H](O)CC(O[C@H](C/C=C\C=C\C([C@H](C)C[C@@H]3CC=O)=O)C)=O)OC)O[C@@H]2C)C1
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>3 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.03.00
Preparing Stock Solutions
The following data is based on the
product
molecular weight
783.95
Batch specific molecular weights may vary
from batch to batch
due to the degree of hydration, which will
affect the solvent
volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass |
1 mg |
5 mg |
10 mg |
| 1 mM |
1.15 mL |
5.76 mL |
11.51 mL |
| 5 mM |
0.23 mL |
1.15 mL |
2.3 mL |
| 10 mM |
0.12 mL |
0.58 mL |
1.15 mL |
| 50 mM |
0.02 mL |
0.12 mL |
0.23 mL |
1: Kakavas SJ, Katz L, Stassi D. Identification and characterization of the niddamycin polyketide synthase genes from Streptomyces caelestis. J Bacteriol. 1997 Dec;179(23):7515-22. PubMed PMID: 9393718; PubMed Central PMCID: PMC179704.
2: HUBER G, WALLHAEUSSER KH, FRIES L, STEIGLER A, WEIDENMUELLER HL. [Niddamycin, a new macrolide antibiotic]. Arzneimittelforschung. 1962 Dec;12:1191-5. German. PubMed PMID: 13955393.
3: Stassi DL, Kakavas SJ, Reynolds KA, Gunawardana G, Swanson S, Zeidner D, Jackson M, Liu H, Buko A, Katz L. Ethyl-substituted erythromycin derivatives produced by directed metabolic engineering. Proc Natl Acad Sci U S A. 1998 Jun 23;95(13):7305-9. PubMed PMID: 9636144; PubMed Central PMCID: PMC22598.
4: Newbrun E, Felton RA, Bulkacz J. Susceptibility of some plaque microorganisms to chemotherapeutic agents. J Dent Res. 1976 Jul-Aug;55(4):574-9. PubMed PMID: 1064600.
5: Tejedor F, Ballesta JP. Components of the macrolide binding site on the ribosome. J Antimicrob Chemother. 1985 Jul;16 Suppl A:53-62. PubMed PMID: 4055551.
6: Goldman RC, Capobianco JO. Role of an energy-dependent efflux pump in plasmid pNE24-mediated resistance to 14- and 15-membered macrolides in Staphylococcus epidermidis. Antimicrob Agents Chemother. 1990 Oct;34(10):1973-80. PubMed PMID: 1963291; PubMed Central PMCID: PMC171974.
7: Tejedor F, Ballesta JP. Reaction of some macrolide antibiotics with the ribosome. Labeling of the binding site components. Biochemistry. 1986 Nov 18;25(23):7725-31. PubMed PMID: 3542032.
8: Pestka S, Nakagawa A, Omura S. Effect of leucomycins and analogues on binding [14C ]erythromycin to Escherichia coli ribosomes. Antimicrob Agents Chemother. 1974 Nov;6(5):606-12. PubMed PMID: 15825314; PubMed Central PMCID: PMC444701.
9: Pestka S. Antibiotics as probes of ribosome structure: binding of chloramphenicol and erythromycin to polyribosomes; effect of other antibiotics. Antimicrob Agents Chemother. 1974 Mar;5(3):255-67. PubMed PMID: 4599122; PubMed Central PMCID: PMC428957.
10: Birmingham VA, Cox KL, Larson JL, Fishman SE, Hershberger CL, Seno ET. Cloning and expression of a tylosin resistance gene from a tylosin-producing strain of Streptomyces fradiae. Mol Gen Genet. 1986 Sep;204(3):532-9. PubMed PMID: 3020383.
11: Tejedor F, Ballesta JP. Ribosome structure: binding site of macrolides studied by photoaffinity labeling. Biochemistry. 1985 Jan 15;24(2):467-72. PubMed PMID: 3884043.
12: Mellouli L, Ben Ameur-Mehdi R, Sioud S, Salem M, Bejar S. Isolation, purification and partial characterization of antibacterial activities produced by a newly isolated Streptomyces sp. US24 strain. Res Microbiol. 2003 Jun;154(5):345-52. PubMed PMID: 12837510.
13: Vilches C, Hernandez C, Mendez C, Salas JA. Role of glycosylation and deglycosylation in biosynthesis of and resistance to oleandomycin in the producer organism, Streptomyces antibioticus. J Bacteriol. 1992 Jan;174(1):161-5. PubMed PMID: 1530845; PubMed Central PMCID: PMC205690.
