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MedKoo Cat#: 585379 | Name: Etamycin

Description:

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

Etamycin is an antibiotic substance (macrolide lactone) produced by Streptomyces griseus and allied Streptomyces that is active against gram-positive Mycobacterium tuberculosis and some fungi and other "coccal" infections.

Chemical Structure

Etamycin
Etamycin
CAS#299-20-7

Theoretical Analysis

MedKoo Cat#: 585379

Name: Etamycin

CAS#: 299-20-7

Chemical Formula: C44H62N8O11

Exact Mass: 878.4538

Molecular Weight: 879.03

Elemental Analysis: C, 60.12; H, 7.11; N, 12.75; O, 20.02

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
Etamycin; Antibiotic F-1370A; Antibiotic K-179; Viridogrisein; Viridogrisein I
IUPAC/Chemical Name
3-hydroxy-N-[(3R,6S,7R,10S,13S,16S,22R,24R)-24-hydroxy-7,11,13,17,20-pentamethyl-16-[(2S)-3-methylbutan-2-yl]-3-(2-methylpropyl)-2,5,9,12,15,18,21-heptaoxo-10-phenyl-8-oxa-1,4,11,14,17,20-hexazabicyclo[20.3.0]pentacosan-6-yl]pyridine-2-carboxamide
InChi Key
SATIISJKSAELDC-ZIOPZPSVSA-N
InChi Code
InChI=1S/C44H62N8O11/c1-23(2)19-30-42(60)52-21-29(53)20-31(52)43(61)49(8)22-33(55)50(9)36(25(5)24(3)4)40(58)46-26(6)41(59)51(10)37(28-15-12-11-13-16-28)44(62)63-27(7)34(38(56)47-30)48-39(57)35-32(54)17-14-18-45-35/h11-18,23-27,29-31,34,36-37,53-54H,19-22H2,1-10H3,(H,46,58)(H,47,56)(H,48,57)/t25-,26-,27+,29+,30+,31+,34-,36-,37-/m0/s1
SMILES Code
O=C(C1=NC=CC=C1O)N[C@@H]([C@@H](C)OC([C@H](C2=CC=CC=C2)N(C)C([C@H](C)NC([C@H]([C@H](C(C)C)C)N(C)C(CN3C)=O)=O)=O)=O)C(N[C@H](CC(C)C)C(N4C[C@H](O)C[C@]4([H])C3=O)=O)=O
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
>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
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 879.03 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: Schinke C, Martins T, Queiroz SCN, Melo IS, Reyes FGR. Antibacterial Compounds from Marine Bacteria, 2010-2015. J Nat Prod. 2017 Apr 28;80(4):1215-1228. doi: 10.1021/acs.jnatprod.6b00235. Epub 2017 Mar 31. Review. PubMed PMID: 28362500. 2: Schlumbohm W, Keller U. Chromophore activating enzyme involved in the biosynthesis of the mikamycin B antibiotic etamycin from Streptomyces griseoviridus. J Biol Chem. 1990 Feb 5;265(4):2156-61. PubMed PMID: 2153676. 3: Hosoda K, Koyama N, Kanamoto A, Tomoda H. Discovery of Nosiheptide, Griseoviridin, and Etamycin as Potent Anti-Mycobacterial Agents against Mycobacterium avium Complex. Molecules. 2019 Apr 16;24(8). pii: E1495. doi: 10.3390/molecules24081495. PubMed PMID: 30995807; PubMed Central PMCID: PMC6514863. 4: Haste NM, Perera VR, Maloney KN, Tran DN, Jensen P, Fenical W, Nizet V, Hensler ME. Activity of the streptogramin antibiotic etamycin against methicillin-resistant Staphylococcus aureus. J Antibiot (Tokyo). 2010 May;63(5):219-24. doi: 10.1038/ja.2010.22. Epub 2010 Mar 26. PubMed PMID: 20339399; PubMed Central PMCID: PMC2889693. 5: Sun P, Maloney KN, Nam SJ, Haste NM, Raju R, Aalbersberg W, Jensen PR, Nizet V, Hensler ME, Fenical W. Fijimycins A-C, three antibacterial etamycin-class depsipeptides from a marine-derived Streptomyces sp. Bioorg Med Chem. 2011 Nov 15;19(22):6557-62. doi: 10.1016/j.bmc.2011.06.053. Epub 2011 Jun 26. PubMed PMID: 21745747; PubMed Central PMCID: PMC3205191. 6: Lawrence CC, Sobey WJ, Field RA, Baldwin JE, Schofield CJ. Purification and initial characterization of proline 4-hydroxylase from Streptomyces griseoviridus P8648: a 2-oxoacid, ferrous-dependent dioxygenase involved in etamycin biosynthesis. Biochem J. 1996 Jan 1;313 ( Pt 1):185-91. PubMed PMID: 8546682; PubMed Central PMCID: PMC1216881. 7: Chopra C, Hook DJ, Vining LC, Das BC, Shimizu S, Taylor A, Wright JL. Congeners of etamycin produced by Streptomyces griseoviridus. J Antibiot (Tokyo). 1979 Apr;32(4):392-401. PubMed PMID: 468725. 8: Kamal F, Katz E. Studies of etamycin biosynthesis employing short-term experiments with radiolabeled precursors. J Antibiot (Tokyo). 1976 Sep;29(9):944-9. PubMed PMID: 825498. 9: Terekhova LP, Galatenko OA, Kuliaeva VV, Tolstykh IV, Golova TP, Katrukha GS, Zhukhmistova NE, Ol'khovatova OL, Malkina ND, Boĭkova IuV. [Production of griseoviridin and etamycin by the new culture, Streptomyces albolongus]. Antibiot Khimioter. 1992 Dec;37(12):19-21. Russian. PubMed PMID: 1304120. 10: Trenozhnikova LP, Khasenova AK, Balgimbaeva AS, Fedorova GB, Katrukha GS, Tokareva NL, Kwa BH, Azizan A. Characterization of the antibiotic compound no. 70 produced by Streptomyces sp. IMV-70. ScientificWorldJournal. 2012;2012:594231. doi: 10.1100/2012/594231. Epub 2012 Mar 12. PubMed PMID: 22536145; PubMed Central PMCID: PMC3320011. 11: Xie Y, Ma J, Qin X, Li Q, Ju J. Identification and utilization of two important transporters: SgvT1 and SgvT2, for griseoviridin and viridogrisein biosynthesis in Streptomyces griseoviridis. Microb Cell Fact. 2017 Oct 25;16(1):177. doi: 10.1186/s12934-017-0792-8. PubMed PMID: 29065880; PubMed Central PMCID: PMC5655939. 12: Xie Y, Wang B, Liu J, Zhou J, Ma J, Huang H, Ju J. Identification of the biosynthetic gene cluster and regulatory cascade for the synergistic antibacterial antibiotics griseoviridin and viridogrisein in Streptomyces griseoviridis. Chembiochem. 2012 Dec 21;13(18):2745-57. doi: 10.1002/cbic.201200584. Epub 2012 Nov 19. PubMed PMID: 23161816. 13: Katz E, Kamal F, Mason K. Biosynthesis of trans-4-hydroxy-L-proline by Streptomyces griseoviridus. J Biol Chem. 1979 Jul 25;254(14):6684-90. PubMed PMID: 447743. 14: Hook DJ, Vining LC. Biosynthetic precursors of etamycin, a peptidolactone antibiotic from Streptomyces griseoviridus. Can J Biochem. 1973 Dec;51(12):1630-7. PubMed PMID: 4775435. 15: Perlman D, Hou CT. Substrate specificity of Actinoplanes antibiotic peptide lactonases. Appl Microbiol. 1969 Aug;18(2):272-3. PubMed PMID: 4185237; PubMed Central PMCID: PMC377957. 16: GARCIA-MENDOZA C. STUDIES ON THE MODE OF ACTION OF ETAMYCIN (VIRIDOGRISEIN). Biochim Biophys Acta. 1965 Feb 15;97:394-6. PubMed PMID: 14292864. 17: Walker JE, Bodanszky M, Perlman D. The biogenetic origin of the N-methyl-gamma-methyl-L-isoleucine residue of etamycin. J Antibiot (Tokyo). 1970 May;23(5):255-6. PubMed PMID: 5423670. 18: Walker JE, Perlman D. Biogenesis of the L-N, -dimethylleucine residue of etamycin. Biotechnol Bioeng. 1971 May;13(3):371-9. PubMed PMID: 5130176. 19: Sheehan JC, Ledis SL. Total synthesis of a monocyclic peptide lactone antibiotic, etamycin. J Am Chem Soc. 1973 Feb 7;95(3):875-9. PubMed PMID: 4688657. 20: Bateman KP, Thibault P, Yang K, White RL, Vining LC. Probing the substrate specificity of an enzyme catalyzing inactivation of streptogramin B antibiotics using LC-MS and LC-MS/MS. J Mass Spectrom. 1997 Oct;32(10):1057-63. PubMed PMID: 9358629.