Aurodox

Aurodox
Legal status
Legal status	Investigational;
Identifiers
	IUPAC name (2S)-N-[(2E,4E,6S,7R)-7-[(2S,3S,4R,5R)-3,4-dihydroxy-5-[(1E,3E,5E)-7-(4-hydroxy-1-methyl-2-oxopyridin-3-yl)-6-methyl-7-oxohepta-1,3,5-trienyl]oxolan-2-yl]-6-methoxy-5-methylocta-2,4-dienyl]-2-[(2R,3R,4R,6S)-2,3,4-trihydroxy-5,5-dimethyl-6-[(1E,3Z)-penta-1,3-dienyl]oxan-2-yl]butanamide;
CAS Number	12704-90-4;
PubChem CID	135509117;
DrugBank	DB04124;
ChemSpider	16735686;
UNII	PGP5RZH64G;
ChEMBL	ChEMBL3221419;
CompTox Dashboard (EPA)	DTXSID801043992 ;
Chemical and physical data
Formula	C44H62N2O12
Molar mass	810.982 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CC[C@H](C(=O)NC/C=C/C=C(\C)/[C@H]([C@@H](C)[C@H]1[C@H]([C@H]([C@H](O1)/C=C/C=C/C=C(\C)/C(=O)C2=C(C=CN(C2=O)C)O)O)O)OC)[C@@]3([C@@H]([C@@H](C([C@@H](O3)/C=C/C=C\C)(C)C)O)O)O;
	InChI 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; Key:NTAHMPNXQOYXSX-WKSONYIQSA-N;

Aurodox (X-5108, goldinomycin) is a naturally occurring polyketide antibiotic drug, first isolated in 1972 from Streptomyces goldiniensis. It is active against various species of Gram-positive bacteria through inhibition of the type III secretion system (T3SS), and while its chemical properties make it unsuitable for use in human medicine directly, it is used in antibiotic research and related compounds may be developed for medical use.^[1]^[2]^[3]

References

^ McHugh RE, O'Boyle N, Connolly JP, Hoskisson PA, Roe AJ (February 2019). "Characterization of the Mode of Action of Aurodox, a Type III Secretion System Inhibitor from Streptomyces goldiniensis". Infection and Immunity. 87 (2). doi:10.1128/IAI.00595-18. PMC 6346137. PMID 30455200.
^ Kimishima A, Hagimoto D, Honsho M, Watanabe Y, Iwatsuki M, Tsutsumi H, et al. (August 2022). "Insights into the structure-activity relationship of a type III secretion system inhibitor, aurodox". Bioorganic & Medicinal Chemistry Letters. 69: 128779. doi:10.1016/j.bmcl.2022.128779. PMID 35545199.
^ Watanabe Y, Haneda T, Kimishima A, Kuwae A, Suga T, Suzuki T, et al. (April 2024). "PurA is the main target of aurodox, a type III secretion system inhibitor". Proceedings of the National Academy of Sciences of the United States of America. 121 (17): e2322363121. Bibcode:2024PNAS..12122363W. doi:10.1073/pnas.2322363121. PMC 11046696. PMID 38640341.

[1] McHugh RE, O'Boyle N, Connolly JP, Hoskisson PA, Roe AJ (February 2019). "Characterization of the Mode of Action of Aurodox, a Type III Secretion System Inhibitor from Streptomyces goldiniensis". Infection and Immunity. 87 (2). doi:10.1128/IAI.00595-18. PMC 6346137. PMID 30455200.

[2] Kimishima A, Hagimoto D, Honsho M, Watanabe Y, Iwatsuki M, Tsutsumi H, et al. (August 2022). "Insights into the structure-activity relationship of a type III secretion system inhibitor, aurodox". Bioorganic & Medicinal Chemistry Letters. 69: 128779. doi:10.1016/j.bmcl.2022.128779. PMID 35545199.

[3] Watanabe Y, Haneda T, Kimishima A, Kuwae A, Suga T, Suzuki T, et al. (April 2024). "PurA is the main target of aurodox, a type III secretion system inhibitor". Proceedings of the National Academy of Sciences of the United States of America. 121 (17): e2322363121. Bibcode:2024PNAS..12122363W. doi:10.1073/pnas.2322363121. PMC 11046696. PMID 38640341.

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See also

References