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Aurantimycin A

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Aurantimycin A
Names
IUPAC name
(2R)-N-[(6S,9R,16S,17S,20R,23S)-7,21-dihydroxy-6-(methoxymethyl)-20-methyl-2,5,8,15,19,22-hexaoxo-17-propan-2-yl-18-oxa-1,4,7,13,14,21,27-heptazatricyclo[21.4.0.09,14]heptacosan-16-yl]-2-hydroxy-2-[(2S,5S,6S)-2-hydroxy-6-methyl-5-(2-methylpropyl)oxan-2-yl]propanamide[1]
Other names
Aurantimycin
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
  • InChI=1S/C38H64N8O14/c1-20(2)17-24-13-14-38(55,60-23(24)6)37(7,54)36(53)42-29-30(21(3)4)59-35(52)22(5)45(56)32(49)25-11-9-15-40-43(25)28(47)18-39-31(48)27(19-58-8)46(57)33(50)26-12-10-16-41-44(26)34(29)51/h20-27,29-30,40-41,54-57H,9-19H2,1-8H3,(H,39,48)(H,42,53)/t22-,23+,24+,25+,26-,27+,29+,30+,37+,38+/m1/s1
    Key: JSVPJXYQXDNLRD-NSCUIBACSA-N
  • C[C@H]1[C@@H](CC[C@](O1)([C@](C)(C(=O)N[C@H]2[C@@H](OC(=O)[C@H](N(C(=O)[C@@H]3CCCNN3C(=O)CNC(=O)[C@@H](N(C(=O)[C@H]4CCCNN4C2=O)O)COC)O)C)C(C)C)O)O)CC(C)C
Properties
C38H64N8O14
Molar mass 856.972 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Aurantimycin A is a depsipeptide antibiotic with the molecular formula C38H64N8O14.[2][1] Aurantimycin A is produced by the bacterium Streptomyces aurantiacus.[3][4] Aurantimycin A also show cytotoxic properties.[5]

References

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  1. ^ a b "Aurantimycin A". Pubchem.ncbi.NLM.nih.gov.
  2. ^ "Aurantimycin A, Depsipeptide antibiotic (CAS 162478-50-4) (ab144195) | Abcam". www.abcam.com.
  3. ^ Grigoriev, P.; Schlegel, R.; Dornberger, K.; Gräfe, U. (1 February 1995). "Formation of membrane pores by aurantimycins A and B, new lipopeptide antibiotics from Streptomyces aurantiacus". Bioelectrochemistry and Bioenergetics. 36 (1): 57–59. doi:10.1016/0302-4598(94)01721-C. ISSN 0302-4598.
  4. ^ Kolar, Patrik; Tišler, Miha (28 October 1999). "Recent Advances in the Chemistry of Pyridazines". Advances in Heterocyclic Chemistry Volume 75. Vol. 75. Academic Press. p. 170. doi:10.1016/S0065-2725(08)60985-X. ISBN 978-0-08-057661-9.
  5. ^ Bycroft, Barrie W.; Payne, David J. (9 August 2013). Dictionary of Antibiotics and Related Substances: with CD-ROM, Second Edition. CRC Press. p. 303. ISBN 978-1-4822-8215-3.

Further reading

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