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MedKoo Cat#: 571013 | Name: Mycinamicin I

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Mycinamicin I is a macrolide antibiotic involved in biosynthetic pathways.

Chemical Structure

Mycinamicin I
Mycinamicin I
CAS#73665-15-3

Theoretical Analysis

MedKoo Cat#: 571013

Name: Mycinamicin I

CAS#: 73665-15-3

Chemical Formula: C37H61NO12

Exact Mass: 711.4194

Molecular Weight: 711.89

Elemental Analysis: C, 62.43; H, 8.64; N, 1.97; O, 26.97

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
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Synonym
Mycinamicin I, A 11725 I, Antibiotic A 11725 I, Mycinomycin I
IUPAC/Chemical Name
(2R,3R,6E,8S,9S,10S,12R,14E)-9-(((2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)-3-ethyl-2-((((2R,3R,4R,5R,6R)-5-hydroxy-3,4-dimethoxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)methyl)-8,10,12-trimethyl-4,17-dioxabicyclo[14.1.0]heptadeca-6,14-diene-5,13-dione
InChi Key
QABCJBNUVVMWAL-HXRJSAKRSA-N
InChi Code
InChI=1S/C37H61NO12/c1-11-27-24(18-45-37-35(44-10)34(43-9)30(41)23(6)47-37)33-28(49-33)14-13-26(39)20(3)16-21(4)32(19(2)12-15-29(40)48-27)50-36-31(42)25(38(7)8)17-22(5)46-36/h12-15,19-25,27-28,30-37,41-42H,11,16-18H2,1-10H3/b14-13+,15-12+/t19-,20+,21-,22+,23+,24+,25-,27+,28?,30+,31+,32+,33?,34+,35+,36-,37+/m0/s1
SMILES Code
CC[C@@H]1[C@H](C2C(O2)/C=C/C(=O)[C@@H](C[C@@H]([C@@H]([C@H](/C=C/C(=O)O1)C)O[C@H]3[C@@H]([C@H](C[C@H](O3)C)N(C)C)O)C)C)CO[C@H]4[C@@H]([C@@H]([C@@H]([C@H](O4)C)O)OC)OC
Appearance
Solid powder
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
>2 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
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 711.89 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.

Recalculate based on batch purity %
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: Li S, Tietz DR, Rutaganira FU, Kells PM, Anzai Y, Kato F, Pochapsky TC, Sherman DH, Podust LM. Substrate recognition by the multifunctional cytochrome P450 MycG in mycinamicin hydroxylation and epoxidation reactions. J Biol Chem. 2012 Nov 2;287(45):37880-90. doi: 10.1074/jbc.M112.410340. Epub 2012 Sep 5. PubMed PMID: 22952225; PubMed Central PMCID: PMC3488060. 2: DeMars MD 2nd, Sheng F, Park SR, Lowell AN, Podust LM, Sherman DH. Biochemical and Structural Characterization of MycCI, a Versatile P450 Biocatalyst from the Mycinamicin Biosynthetic Pathway. ACS Chem Biol. 2016 Sep 16;11(9):2642-54. doi: 10.1021/acschembio.6b00479. Epub 2016 Aug 5. PubMed PMID: 27420774; PubMed Central PMCID: PMC5026600. 3: Anzai Y, Tsukada S, Sakai A, Masuda R, Harada C, Domeki A, Li S, Kinoshita K, Sherman DH, Kato F. Function of cytochrome P450 enzymes MycCI and MycG in Micromonospora griseorubida, a producer of the macrolide antibiotic mycinamicin. Antimicrob Agents Chemother. 2012 Jul;56(7):3648-56. doi: 10.1128/AAC.06063-11. Epub 2012 Apr 30. PubMed PMID: 22547618; PubMed Central PMCID: PMC3393388. 4: Tsukada S, Anzai Y, Li S, Kinoshita K, Sherman DH, Kato F. Gene targeting for O-methyltransferase genes, mycE and mycF, on the chromosome of Micromonospora griseorubida producing mycinamicin with a disruption cassette containing the bacteriophage phi C31 attB attachment site. FEMS Microbiol Lett. 2010 Mar;304(2):148-56. doi: 10.1111/j.1574-6968.2010.01899.x. Epub 2010 Jan 11. PubMed PMID: 20158522. 5: Akey DL, Li S, Konwerski JR, Confer LA, Bernard SM, Anzai Y, Kato F, Sherman DH, Smith JL. A new structural form in the SAM/metal-dependent o methyltransferase family: MycE from the mycinamicin biosynthetic pathway. J Mol Biol. 2011 Oct 21;413(2):438-50. doi: 10.1016/j.jmb.2011.08.040. Epub 2011 Aug 23. PubMed PMID: 21884704; PubMed Central PMCID: PMC3193595. 6: Anzai Y, Saito N, Tanaka M, Kinoshita K, Koyama Y, Kato F. Organization of the biosynthetic gene cluster for the polyketide macrolide mycinamicin in Micromonospora griseorubida. FEMS Microbiol Lett. 2003 Jan 21;218(1):135-41. PubMed PMID: 12583909. 7: Li S, Anzai Y, Kinoshita K, Kato F, Sherman DH. Functional analysis of MycE and MycF, two O-methyltransferases involved in the biosynthesis of mycinamicin macrolide antibiotics. Chembiochem. 2009 May 25;10(8):1297-301. doi: 10.1002/cbic.200900088. PubMed PMID: 19415708; PubMed Central PMCID: PMC2861363. 8: Takenaka S, Yoshida K, Yamaguchi O, Shimizu K, Morohoshi T, Kinoshita K. Enhancement of mycinamicin production by dotriacolide in Micromonospora griseorubida. FEMS Microbiol Lett. 1998 Oct 1;167(1):95-100. PubMed PMID: 9841223. 9: Anzai Y, Ishii Y, Yoda Y, Kinoshita K, Kato F. The targeted inactivation of polyketide synthase mycAV in the mycinamicin producer, Micromonospora griseorubida, and a complementation study. FEMS Microbiol Lett. 2004 Sep 15;238(2):315-20. PubMed PMID: 15358416. 10: Edelstein PH, Pasiecznik KA, Yasui VK, Meyer RD. Susceptibility of Legionella spp. to mycinamicin I and II and other macrolide antibiotics: effects of media composition and origin of organisms. Antimicrob Agents Chemother. 1982 Jul;22(1):90-3. PubMed PMID: 7125633; PubMed Central PMCID: PMC183679. 11: Inouye M, Suzuki H, Takada Y, Muto N, Horinouchi S, Beppu T. A gene encoding mycinamicin III O-methyltransferase from Micromonospora griseorubida. Gene. 1994 Apr 8;141(1):121-4. PubMed PMID: 8163162. 12: Anzai Y, Li S, Chaulagain MR, Kinoshita K, Kato F, Montgomery J, Sherman DH. Functional analysis of MycCI and MycG, cytochrome P450 enzymes involved in biosynthesis of mycinamicin macrolide antibiotics. Chem Biol. 2008 Sep 22;15(9):950-9. doi: 10.1016/j.chembiol.2008.07.014. PubMed PMID: 18804032; PubMed Central PMCID: PMC2774819. 13: Inouye M, Morohoshi T, Horinouchi S, Beppu T. Cloning and sequences of two macrolide-resistance-encoding genes from mycinamicin-producing Micromonospora griseorubida. Gene. 1994 Apr 8;141(1):39-46. PubMed PMID: 8163173. 14: Inouye M, Takada Y, Muto N, Beppu T, Horinouchi S. Characterization and expression of a P-450-like mycinamicin biosynthesis gene using a novel Micromonospora-Escherichia coli shuttle cosmid vector. Mol Gen Genet. 1994 Nov 15;245(4):456-64. PubMed PMID: 7808395. 15: Bernard SM, Akey DL, Tripathi A, Park SR, Konwerski JR, Anzai Y, Li S, Kato F, Sherman DH, Smith JL. Structural basis of substrate specificity and regiochemistry in the MycF/TylF family of sugar O-methyltransferases. ACS Chem Biol. 2015 May 15;10(5):1340-51. doi: 10.1021/cb5009348. Epub 2015 Feb 26. PubMed PMID: 25692963; PubMed Central PMCID: PMC4433623. 16: Hayashi M, Ohno M, Katsumata S, Satoi S, Harada K, Takeda M, Suzuki M. Mycinamicins, new macrolide antibiotics. IV. Structure of mycinamicin III. J Antibiot (Tokyo). 1981 Mar;34(3):276-81. PubMed PMID: 7275809. 17: Anzai Y, Kinoshita K, Seki T, Kato F. Hybrid biosynthesis by targeted inactivation of polyketide synthases in the mycinamicin producer, Micromonospora griseorubida. J Antibiot (Tokyo). 2004 Dec;57(12):819-22. PubMed PMID: 15745119. 18: Kinoshita K, Satoi S, Hayashi M, Nakatsu K. Mycinamicins, new macrolide antibiotics. X. X-ray crystallography and the absolute configuration of mycinamicin IV. J Antibiot (Tokyo). 1989 Jun;42(6):1003-5. PubMed PMID: 2737943. 19: Nakajima Y, Jánosi L, Endou K, Matsuoka M, Hashimoto H. Inducible resistance to a 16-membered macrolide, mycinamicin, in Staphylococcus aureus resistant to 14-membered macrolides and streptogramin B antibiotics. J Pharmacobiodyn. 1992 Jun;15(6):319-24. PubMed PMID: 1432570. 20: Hayashi M, Ohno M, Kinoshita K, Satoi S, Suzuki M, Harada K. Mycinamicins, new macrolide antibiotics. III Isolation and structures of mycinamicin aglycones, mycinolide IV and V. J Antibiot (Tokyo). 1981 Mar;34(3):346-9. PubMed PMID: 7275814.