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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-oxabicyclo[12.4.0]octadeca-1(14),6,12,15,17-pentaen-2-one
Identifiers
3D model (JSmol)	Interactive image
ChEMBL	ChEMBL1173442
PubChem CID	11724428
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/s1 Key: NHAQNKDEUQPSIX-DXOCLGOBSA-N
SMILES C[C@H]1C/C=C/[C@H]([C@H](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⁻¹
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Aigialomycin D is a macrolide antibiotic which is produced by the fungi Aigialus parvus.^[1] Aigialomycin D is a resorcylic acid lactone and has the molecular formula C₁₈H₂₂O₆.^[2] Preliminary studies found that aigialomycin D is a protein kinase inhibitor^[3] with anti-tumor activity. Aigialomycin D has antimalarial activity.^[4]

References[edit]

^ 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.

^ 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.

^ Advances in Phosphotransferases (Alcohol Group Acceptor) Research and Application: 2012 Edition. ScholarlyEditions. 26 December 2012. p. 76. ISBN 978-1-4649-9201-8.

^ 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[edit]

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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