Aurodox Explained

Drug Name:	Aurodox
Legal Status:	Investigational
C:	44
H:	62
N:	2
O:	12
Iupac Name:	(2S)-N-[(2''E'',4''E'',6''S'',7''R'')-7-[(2''S'',3''S'',4''R'',5''R'')-3,4-dihydroxy-5-[(1''E'',3''E'',5''E'')-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-[(2''R'',3''R'',4''R'',6''S'')-2,3,4-trihydroxy-5,5-dimethyl-6-[(1''E'',3''Z'')-penta-1,3-dienyl]oxan-2-yl]butanamide
Cas Number:	12704-90-4
Pubchem:	135509117
Drugbank:	DB04124
Chemspiderid:	16735686
Unii:	PGP5RZH64G
Chembl:	3221419
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
Stdinchi:	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
Stdinchikey:	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]}

See also

• Fluorothiazinone

Notes and References

1. McHugh RE, O'Boyle N, Connolly JP, Hoskisson PA, Roe AJ . Characterization of the Mode of Action of Aurodox, a Type III Secretion System Inhibitor from Streptomyces goldiniensis . Infection and Immunity . 87 . 2 . February 2019 . 30455200 . 10.1128/IAI.00595-18 . 6346137 .
2. Kimishima A, Hagimoto D, Honsho M, Watanabe Y, Iwatsuki M, Tsutsumi H, Inahashi Y, Naher K, Sakai K, Kuwae A, Abe A, Asami Y . Insights into the structure-activity relationship of a type III secretion system inhibitor, aurodox . Bioorganic & Medicinal Chemistry Letters . 69 . 128779 . August 2022 . 35545199 . 10.1016/j.bmcl.2022.128779 .
3. Watanabe Y, Haneda T, Kimishima A, Kuwae A, Suga T, Suzuki T, Iwabuchi Y, Honsho M, Honma S, Iwatsuki M, Matsui H, Hanaki H, Kanoh N, Abe A, Asami Y, Ōmura S . 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 . April 2024 . 38640341 . 10.1073/pnas.2322363121 . 11046696 . 2024PNAS..12122363W .