Evernimicin | CAS# 109545-84-8 | Antibacterial

MedKoo Cat#: 414167 | Name: Evernimicin

Description:

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

Evernimicin is an Antibacterial

Chemical Structure

Evernimicin

CAS#109545-84-8

Theoretical Analysis

MedKoo Cat#: 414167

Name: Evernimicin

CAS#: 109545-84-8

Chemical Formula: C70H97Cl2NO38

Exact Mass: 1629.5066

Molecular Weight: 1631.42

Elemental Analysis: C, 51.54; H, 5.99; Cl, 4.35; N, 0.86; O, 37.27

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.

Bulk Inquiry

Related CAS #

No Data

Synonym

Evernimicin; Ziracin; SCH27899; SCH-27899; SCH 27899

IUPAC/Chemical Name

(2R,3R,4R,6S)-6-(((2R,3a'R,4R,4'R,5S,6R,6'S,7'S,7a'R)-6'-(((2S,3R,4R,5S,6R)-2-(((2R,3S,4S,5S,6S)-6-(((2R,3aS,3a'R,6S,7R,7aS,7'R,7a'S)-7'-((2,4-dihydroxy-6-methylbenzoyl)oxy)-7-hydroxyoctahydro-4H-2,4'-spirobi[[1,3]dioxolo[4,5-c]pyran]-6-yl)oxy)-4-hydroxy-5-methoxy-2-(methoxymethyl)tetrahydro-2H-pyran-3-yl)oxy)-3-hydroxy-5-methoxy-6-methyltetrahydro-2H-pyran-4-yl)oxy)-4,7'-dihydroxy-4',6,7a'-trimethyloctahydro-4'H-spiro[pyran-2,2'-[1,3]dioxolo[4,5-c]pyran]-5-yl)oxy)-4-(((2S,4S,5R,6S)-5-methoxy-4,6-dimethyl-4-nitrotetrahydro-2H-pyran-2-yl)oxy)-2-methyltetrahydro-2H-pyran-3-yl 3,5-dichloro-4-hydroxy-2-methoxy-6-methylbenzoate

InChi Key

UPADRKHAIMTUCC-OWALTSPQSA-N

InChi Code

InChI=1S/C70H97Cl2NO38/c1-24-15-31(74)16-32(75)40(24)61(82)100-36-22-94-70(60-53(36)92-23-93-60)108-37-21-91-63(46(79)52(37)109-70)106-65-56(89-13)45(78)51(35(101-65)20-86-10)104-64-47(80)55(50(87-11)27(4)97-64)105-66-57(81)68(9)59(30(7)98-66)110-69(111-68)18-33(76)48(28(5)107-69)102-38-17-34(99-39-19-67(8,73(84)85)58(90-14)29(6)96-39)49(26(3)95-38)103-62(83)41-25(2)42(71)44(77)43(72)54(41)88-12/h15-16,26-30,33-39,45-53,55-60,63-66,74-81H,17-23H2,1-14H3/t26-,27-,28-,29+,30-,33-,34-,35-,36-,37+,38+,39+,45+,46-,47-,48-,49-,50+,51-,52-,53+,55-,56+,57-,58+,59-,60-,63+,64+,65+,66+,67+,68-,69-,70-/m1/s1

SMILES Code

COC[C@H]1O[C@H]([C@H]([C@H]([C@@H]1O[C@@H]2O[C@@H]([C@@H]([C@@H]([C@H]2O)O[C@@H]3O[C@@H]([C@H]4O[C@@]5(O[C@@]4([C@@H]3O)C)C[C@H]([C@@H]([C@H](O5)C)O[C@H]6C[C@H]([C@@H]([C@H](O6)C)OC(c7c(OC)c(Cl)c(O)c(Cl)c7C)=O)O[C@H]8C[C@@]([C@H]([C@@H](O8)C)OC)([N+]([O-])=O)C)O)C)OC)C)O)OC)O[C@@H]9OC[C@@H]%10O[C@]%11(O[C@H]%10[C@H]9O)OC[C@H]([C@@H]%12OCO[C@@H]%11%12)OC(c%13c(O)cc(O)cc%13C)=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

To be determined

Shelf Life

>2 years if stored properly

Drug Formulation

To be determined

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

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 1,631.42 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: McNicholas PM, Najarian DJ, Mann PA, Hesk D, Hare RS, Shaw KJ, Black TA. Evernimicin binds exclusively to the 50S ribosomal subunit and inhibits translation in cell-free systems derived from both gram-positive and gram- negative bacteria. Antimicrob Agents Chemother. 2000 May;44(5):1121-6. doi: 10.1128/AAC.44.5.1121-1126.2000. PMID: 10770739; PMCID: PMC89832. 2: Krupkin M, Wekselman I, Matzov D, Eyal Z, Diskin Posner Y, Rozenberg H, Zimmerman E, Bashan A, Yonath A. Avilamycin and evernimicin induce structural changes in rProteins uL16 and CTC that enhance the inhibition of A-site tRNA binding. Proc Natl Acad Sci U S A. 2016 Nov 1;113(44):E6796-E6805. doi: 10.1073/pnas.1614297113. Epub 2016 Oct 19. PMID: 27791159; PMCID: PMC5098648. 3: Mann PA, Xiong L, Mankin AS, Chau AS, Mendrick CA, Najarian DJ, Cramer CA, Loebenberg D, Coates E, Murgolo NJ, Aarestrup FM, Goering RV, Black TA, Hare RS, McNicholas PM. EmtA, a rRNA methyltransferase conferring high-level evernimicin resistance. Mol Microbiol. 2001 Sep;41(6):1349-56. doi: 10.1046/j.1365-2958.2001.02602.x. PMID: 11580839. 4: Adrian PV, Mendrick C, Loebenberg D, McNicholas P, Shaw KJ, Klugman KP, Hare RS, Black TA. Evernimicin (SCH27899) inhibits a novel ribosome target site: analysis of 23S ribosomal DNA mutants. Antimicrob Agents Chemother. 2000 Nov;44(11):3101-6. doi: 10.1128/AAC.44.11.3101-3106.2000. PMID: 11036030; PMCID: PMC101610. 5: Souli M, Thauvin-Eliopoulos C, Eliopoulos GM. In vivo activities of evernimicin (SCH 27899) against vancomycin-susceptible and vancomycin-resistant enterococci in experimental endocarditis. Antimicrob Agents Chemother. 2000 Oct;44(10):2733-9. doi: 10.1128/AAC.44.10.2733-2739.2000. PMID: 10991853; PMCID: PMC90144. 6: McNicholas PM, Mann PA, Najarian DJ, Miesel L, Hare RS, Black TA. Effects of mutations in ribosomal protein L16 on susceptibility and accumulation of evernimicin. Antimicrob Agents Chemother. 2001 Jan;45(1):79-83. doi: 10.1128/AAC.45.1.79-83.2001. PMID: 11120948; PMCID: PMC90243. 7: Adrian PV, Zhao W, Black TA, Shaw KJ, Hare RS, Klugman KP. Mutations in ribosomal protein L16 conferring reduced susceptibility to evernimicin (SCH27899): implications for mechanism of action. Antimicrob Agents Chemother. 2000 Mar;44(3):732-8. doi: 10.1128/AAC.44.3.732-738.2000. PMID: 10681347; PMCID: PMC89755. 8: Aarestrup FM, McNicholas PM. Incidence of high-level evernimicin resistance in Enterococcus faecium among food animals and humans. Antimicrob Agents Chemother. 2002 Sep;46(9):3088-90. doi: 10.1128/AAC.46.9.3088-3090.2002. PMID: 12183279; PMCID: PMC127414. 9: Arenz S, Juette MF, Graf M, Nguyen F, Huter P, Polikanov YS, Blanchard SC, Wilson DN. Structures of the orthosomycin antibiotics avilamycin and evernimicin in complex with the bacterial 70S ribosome. Proc Natl Acad Sci U S A. 2016 Jul 5;113(27):7527-32. doi: 10.1073/pnas.1604790113. Epub 2016 Jun 21. PMID: 27330110; PMCID: PMC4941455. 10: Zarazaga M, Tenorio C, Del Campo R, Ruiz-Larrea F, Torres C. Mutations in ribosomal protein L16 and in 23S rRNA in Enterococcus strains for which evernimicin MICs differ. Antimicrob Agents Chemother. 2002 Nov;46(11):3657-9. doi: 10.1128/AAC.46.11.3657-3659.2002. PMID: 12384386; PMCID: PMC128729.