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Aigialomycin D

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Aigialomycin D
Names
IUPAC name (4S,6E,8R,9S,12E)-8,9,16,18-Tetrahydroxy-4-methyl-3-oxabicyclooctadeca-1(14),6,12,15,17-pentaen-2-one
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
PubChem CID
InChI
  • InChI=1S/C18H22O6/c1-11-5-4-8-15(21)14(20)7-3-2-6-12-9-13(19)10-16(22)17(12)18(23)24-11/h2,4,6,8-11,14-15,19-22H,3,5,7H2,1H3/b6-2+,8-4+/t11-,14-,15+/m0/s1Key: NHAQNKDEUQPSIX-DXOCLGOBSA-N
SMILES
  • C1C/C=C/((CC/C=C/C2=C(C(=CC(=C2)O)O)C(=O)O1)O)O
Properties
Chemical formula C18H22O6
Molar mass 334.368 g·mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references
Chemical compound

Aigialomycin D is a macrolide antibiotic which is produced by the fungi Aigialus parvus. Aigialomycin D is a resorcylic acid lactone and has the molecular formula C18H22O6. Preliminary studies found that aigialomycin D is a protein kinase inhibitor with anti-tumor activity. Aigialomycin D has antimalarial activity.

References

  1. Blunt, John W.; Munro, Murray H. G. (19 September 2007). Dictionary of Marine Natural Products with CD-ROM. CRC Press. p. 32. ISBN 978-0-8493-8217-8.
  2. Xu, Jin; Chen, Anqi; Go, Mei-Lin; Nacro, Kassoum; Liu, Boping; Chai, Christina L. L. (8 September 2011). "Exploring Aigialomycin D and Its Analogues as Protein Kinase Inhibitors for Cancer Targets". ACS Medicinal Chemistry Letters. 2 (9): 662–666. doi:10.1021/ml200067t. PMC 4018073. PMID 24900361.
  3. Advances in Phosphotransferases (Alcohol Group Acceptor) Research and Application: 2012 Edition. ScholarlyEditions. 26 December 2012. p. 76. ISBN 978-1-4649-9201-8.
  4. Tiwari, Vinod K. (31 July 2020). Carbohydrates in Drug Discovery and Development: Synthesis and Application. Elsevier. p. 508. ISBN 978-0-12-816676-5.

Further reading

  • Geng, Xudong; Danishefsky, Samuel J. (1 February 2004). "Total Synthesis of Aigialomycin D". Organic Letters. 6 (3): 413–416. doi:10.1021/ol036258m. PMID 14748606.
  • Studies in Natural Products Chemistry. Elsevier. 20 January 2015. p. 386. ISBN 978-0-444-63470-2.
  • Taber, Douglass (23 September 2011). Organic Synthesis: State of the Art 2007 - 2009. Oxford University Press. p. 101. ISBN 978-0-19-020877-6.


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