MedKoo Cat#: 341290 | Name: Aurodox
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Description:

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

Aurodox is a polyketide antibiotic active against Gram-positive bacteria. It is effective against S. pyogenes infection in mice with a 50% curative dose (CD50) value of 71 mg/kg. Aurodox inhibits bacterial protein synthesis by binding to bacterial elongation factor Tu (EF-Tu) and inhibiting its release from the ribosome. Note: This product has purity ≥85% (mixture of tautomers).

Chemical Structure

Aurodox
Aurodox
CAS#12704-90-4

Theoretical Analysis

MedKoo Cat#: 341290

Name: Aurodox

CAS#: 12704-90-4

Chemical Formula: C44H62N2O12

Exact Mass: 810.4303

Molecular Weight: 810.98

Elemental Analysis: C, 65.17; H, 7.71; N, 3.45; O, 23.67

Price and Availability

Size Price Availability Quantity
1mg USD 500.00 2 Weeks
5mg USD 1,250.00 2 Weeks
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Synonym
Aurodox; NSC 233989; NSC-233989; NSC233989; Antibiotic X 5108; Goldinodox; Goldinomycin; 1-methyl-Mocimycin
IUPAC/Chemical Name
(S)-N-((2E,4E,6S,7R)-7-((2S,3S,4R,5R)-3,4-dihydroxy-5-((1E,3E,5E)-7-(4-hydroxy-1-methyl-2-oxo-1,2-dihydropyridin-3-yl)-6-methyl-7-oxohepta-1,3,5-trien-1-yl)tetrahydrofuran-2-yl)-6-methoxy-5-methylocta-2,4-dien-1-yl)-2-((2R,3R,4R,6S)-2,3,4-trihydroxy-5,5-dimethyl-6-((1E,3Z)-penta-1,3-dien-1-yl)tetrahydro-2H-pyran-2-yl)butanamide
InChi Key
NTAHMPNXQOYXSX-WKSONYIQSA-N
InChi Code
InChI=1S/C44H62N2O12/c1-10-12-14-22-32-43(6,7)39(51)40(52)44(55,58-32)29(11-2)41(53)45-24-18-17-20-27(4)37(56-9)28(5)38-36(50)35(49)31(57-38)21-16-13-15-19-26(3)34(48)33-30(47)23-25-46(8)42(33)54/h10,12-23,25,28-29,31-32,35-40,47,49-52,55H,11,24H2,1-9H3,(H,45,53)/b12-10-,15-13+,18-17+,21-16+,22-14+,26-19+,27-20+/t28-,29-,31-,32+,35+,36+,37-,38+,39+,40-,44-/m1/s1
SMILES Code
O[C@H]1[C@@H](/C=C/C=C/C=C(C)/C(C2=C(O)C=CN(C)C2=O)=O)O[C@]([C@H](C)[C@@H](/C(C)=C/C=C/CNC([C@@H](CC)[C@]3(O)[C@H](O)[C@H](O)C(C)(C)[C@H](/C=C/C=C\C)O3)=O)OC)([H])[C@H]1O
Appearance
Solid powder
Purity
≥85% (mixture of tautomers)
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 810.98 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: Nie YL, Wu YD, Wang CX, Lin R, Xie Y, Fang DS, Jiang H, Lian YY. Structure elucidation and antitumour activity of a new macrolactam produced by marine-derived actinomycete Micromonospora sp. FIM05328. Nat Prod Res. 2017 Aug 20:1-6. doi: 10.1080/14786419.2017.1366479. [Epub ahead of print] PubMed PMID: 28823189. 2: Duncan MC, Wong WR, Dupzyk AJ, Bray WM, Linington RG, Auerbuch V. An NF-κB-based high-throughput screen identifies piericidins as inhibitors of the Yersinia pseudotuberculosis type III secretion system. Antimicrob Agents Chemother. 2014;58(2):1118-26. doi: 10.1128/AAC.02025-13. Epub 2013 Dec 2. Erratum in: Antimicrob Agents Chemother. 2016 Jul;60(7):4427. PubMed PMID: 24295981; PubMed Central PMCID: PMC3910828. 3: Kimura K, Iwatsuki M, Nagai T, Matsumoto A, Takahashi Y, Shiomi K, Omura S, Abe A. A small-molecule inhibitor of the bacterial type III secretion system protects against in vivo infection with Citrobacter rodentium. J Antibiot (Tokyo). 2011 Feb;64(2):197-203. doi: 10.1038/ja.2010.155. Epub 2010 Dec 8. PubMed PMID: 21139624. 4: Hogg T, Mesters JR, Hilgenfeld R. Inhibitory mechanisms of antibiotics targeting elongation factor Tu. Curr Protein Pept Sci. 2002 Feb;3(1):121-31. Review. PubMed PMID: 12370016. 5: Vogeley L, Palm GJ, Mesters JR, Hilgenfeld R. Conformational change of elongation factor Tu (EF-Tu) induced by antibiotic binding. Crystal structure of the complex between EF-Tu.GDP and aurodox. J Biol Chem. 2001 May 18;276(20):17149-55. Epub 2001 Jan 30. PubMed PMID: 11278992. 6: Marinelli F, Stella S, Montanini N, Le Monnier F, Cavaletti L, Selva E. Bioconversion capacity of Streptomyces sp GE44282, a producer of the antibiotics heneicomycin and aurodox. J Ind Microbiol. 1995 Jul;15(1):49-54. PubMed PMID: 7662297. 7: Giovane A, Balestrieri C, Balestrieri ML, Servillo L. Interaction studies between elongation factor Tu and anthraniloyl-fluorescent analogues of guanyl nucleotides. Eur J Biochem. 1995 Jan 15;227(1-2):428-32. PubMed PMID: 7851417. 8: Miele A, Goldstein BP, Bandera M, Jarvis C, Resconi A, Williams RJ. Differential susceptibilities of enterococcal species to elfamycin antibiotics. J Clin Microbiol. 1994 Aug;32(8):2016-8. PubMed PMID: 7989561; PubMed Central PMCID: PMC263923. 9: Eccleston JF, Molloy DP, Hinds MG, King RW, Feeney J. Conformational differences between complexes of elongation factor Tu studied 19F-NMR spectroscopy. Eur J Biochem. 1993 Dec 15;218(3):1041-7. PubMed PMID: 8281922. 10: Smitka TA, Bonjouklian R, Perun TJ Jr, Hunt AH, Boeck LV, Yao RC. A83016F, a new member of the aurodox family. J Antibiot (Tokyo). 1992 Apr;45(4):433-43. PubMed PMID: 1592675. 11: Hall CC, Watkins JD, Georgopapadakou NH. Comparison of the Tu elongation factors from Staphylococcus aureus and Escherichia coli: possible basis for elfamycin insensitivity. Antimicrob Agents Chemother. 1991 Nov;35(11):2366-70. PubMed PMID: 1839491; PubMed Central PMCID: PMC245386. 12: Dewey RS, Hensens OD, Douglas AW, Albers-Schönberg G. The structure of heneicomycin. J Antibiot (Tokyo). 1991 Aug;44(8):838-43. PubMed PMID: 1917698. 13: Abrahams JP, van Raaij MJ, Ott G, Kraal B, Bosch L. Kirromycin drastically reduces the affinity of Escherichia coli elongation factor Tu for aminoacyl-tRNA. Biochemistry. 1991 Jul 9;30(27):6705-10. PubMed PMID: 2065055. 14: Ferrari P, Edwards D, Gallo GG, Selva E. Antibiotic SB22484: a novel complex of the aurodox group. II. Structure elucidation of the four factors. J Antibiot (Tokyo). 1990 Nov;43(11):1359-66. PubMed PMID: 2272912. 15: Selva E, Beretta G, Pallanza R, Goldstein BP, Berti M, Edwards DM, Denaro M. Antibiotic SB22484: a novel complex of the aurodox group. I. Taxonomy of the producing organism, isolation of the antibiotics and chemical and biological characterization. J Antibiot (Tokyo). 1990 Nov;43(11):1349-58. PubMed PMID: 2272911. 16: Dell VA, Miller DL, Johnson AE. Effects of nucleotide- and aurodox-induced changes in elongation factor Tu conformation upon its interactions with aminoacyl transfer RNA. A fluorescence study. Biochemistry. 1990 Feb 20;29(7):1757-63. PubMed PMID: 2110000. 17: Jefson MR, Bordner J, Reese CP, Whipple EB. UK-69,753, a novel member of the efrotomycin family of antibiotics. II. Structure determination and biological activity. J Antibiot (Tokyo). 1989 Nov;42(11):1610-8. PubMed PMID: 2584145. 18: Hwang YW, McCabe PG, Innis MA, Miller DL. Site-directed mutagenesis of the GDP binding domain of bacterial elongation factor Tu. Arch Biochem Biophys. 1989 Nov 1;274(2):394-403. PubMed PMID: 2508560. 19: Balestrieri C, Giovane A, Quagliuolo L, Servillo L, Chinali G. Conformation and reactivity changes induced by N-methylkirromycin (aurodox) in elongation factor Tu. Biochemistry. 1989 Aug 22;28(17):7097-101. PubMed PMID: 2510820. 20: Nielsen JB, Kaplan L. A resting cell system for efrotomycin biosynthesis. J Antibiot (Tokyo). 1989 Jun;42(6):944-51. PubMed PMID: 2737954.