Everninomicin

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MedKoo CAT#: 414166

CAS#: 53024-98-9

Description: Everninomicin is a new oligosaccharide antibiotic

Chemical Structure

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Everninomicin
CAS# 53024-98-9
Instruction

Theoretical Analysis

MedKoo Cat#: 414166
Name: Everninomicin
CAS#: 53024-98-9
Chemical Formula: C70H97Cl2NO38
Exact Mass: 1,629.51
Molecular Weight: 1,631.415
Elemental Analysis: C, 51.54; H, 5.99; Cl, 4.35; N, 0.86; O, 37.27

Price and Availability

This product is not in stock, which may be available by custom synthesis. For cost-effective reason, minimum order is 1g (price is usually high, lead time is 2~3 months, depending on the technical challenge). Quote less than 1g will not be provided. To request quote, please email to sales @medkoo.com or click below button.
Note: Price will be listed if it is available in the future.

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Synonym: Everninomicin

IUPAC/Chemical Name: (2R,3R,4R,6S)-6-(((3a'R,4R,4'R,5S,6R,6'S,7'S,7a'R)-6'-(((2S,3R,4S,5S,6R)-2-(((2R,4S,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-(((2R,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-JBNGTWNESA-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([C@H](C1O[C@@H]2O[C@@H]([C@@H]([C@H]([C@H]2O)O[C@@H]3O[C@@H]([C@H]4OC5(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:

Biological target:
In vitro activity:
In vivo activity:

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.

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
Formulation protocol:
In vitro protocol:
In vivo protocol:

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1: Limbrick EM, Yñigez-Gutierrez AE, Dulin CC, Derewacz DK, Spraggins JM, McCulloch KM, Iverson TM, Bachmann BO. Methyltransferase Contingencies in the Pathway of Everninomicin D Antibiotics and Analogues. Chembiochem. 2020 Dec 1;21(23):3349-3358. doi: 10.1002/cbic.202000305. Epub 2020 Sep 7. PMID: 32686210.

2: Limbrick EM, Graf M, Derewacz DK, Nguyen F, Spraggins JM, Wieland M, Ynigez- Gutierrez AE, Reisman BJ, Zinshteyn B, McCulloch KM, Iverson TM, Green R, Wilson DN, Bachmann BO. Bifunctional Nitrone-Conjugated Secondary Metabolite Targeting the Ribosome. J Am Chem Soc. 2020 Oct 28;142(43):18369-18377. doi: 10.1021/jacs.0c04675. Epub 2020 Oct 19. PMID: 32709196; PMCID: PMC8129991.

3: Starbird CA, Perry NA, Chen Q, Berndt S, Yamakawa I, Loukachevitch LV, Limbrick EM, Bachmann BO, Iverson TM, McCulloch KM. The Structure of the Bifunctional Everninomicin Biosynthetic Enzyme EvdMO1 Suggests Independent Activity of the Fused Methyltransferase-Oxidase Domains. Biochemistry. 2018 Dec 18;57(50):6827-6837. doi: 10.1021/acs.biochem.8b00836. Epub 2018 Dec 7. PMID: 30525509; PMCID: PMC7231510.

4: Hidai H. [Antibiotics--TAZ/PIPC, synercid, linezolid, everninomicin]. Nihon Rinsho. 2001 Apr;59(4):785-9. Japanese. PMID: 11305007.

5: Foster DR, Rybak MJ. Pharmacologic and bacteriologic properties of SCH-27899 (Ziracin), an investigational antibiotic from the everninomicin family. Pharmacotherapy. 1999 Oct;19(10):1111-7. doi: 10.1592/phco.19.15.1111.30576. PMID: 10512059.

6: Nakashio S, Iwasawa H, Dun FY, Kanemitsu K, Shimada J. Everninomicin, a new oligosaccharide antibiotic: its antimicrobial activity, post-antibiotic effect and synergistic bactericidal activity. Drugs Exp Clin Res. 1995;21(1):7-16. PMID: 7796712.

7: Nagashima S, Niwa M, Nishiki K, Hosoya T, Hishida A, Uematsu T. Effects of SCH27899 (Ziracin), an oligosaccharide everninomicin antibiotic, on urate kinetics in humans. Eur J Clin Pharmacol. 2004 Jun;60(4):255-64. doi: 10.1007/s00228-004-0755-y. Epub 2004 Apr 16. PMID: 15088132.

8: Aarestrup FM. Association between decreased susceptibility to a new antibiotic for treatment of human diseases, everninomicin (SCH 27899), and resistance to an antibiotic used for growth promotion in animals, avilamycin. Microb Drug Resist. 1998 Summer;4(2):137-41. doi: 10.1089/mdr.1998.4.137. PMID: 9651001.

9: Reimann H, Jaret RS, Sarre OZ. The chemistry of the everninomicin antibiotics. II. The structure of everninocin and its identification with curacin. J Antibiot (Tokyo). 1969 Mar;22(3):131-2. doi: 10.7164/antibiotics.22.131. PMID: 5789902.

10: Ganguly AK, Sarre OZ, Greeves D, Morton J. Letter: Structure of everninomicin D-1. J Am Chem Soc. 1975 Apr 2;97(7):1982-5. doi: 10.1021/ja00840a078. PMID: 1133407.