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Frenolicin B

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Frenolicin B
Names
IUPAC name (11R,15R,17R)-4-Hydroxy-17-propyl-12,16-dioxatetracycloheptadeca-1(10),3(8),4,6-tetraene-2,9,13-trione
Identifiers
CAS Number
3D model (JSmol)
Beilstein Reference 6436493
ChEBI
ChEMBL
ChemSpider
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C18H16O6/c1-2-4-10-14-15(18-11(23-10)7-12(20)24-18)16(21)8-5-3-6-9(19)13(8)17(14)22/h3,5-6,10-11,18-19H,2,4,7H2,1H3/t10-,11-,18+/m1/s1Key: AVCPRTNVVRPELB-YRUZYCQGSA-N
SMILES
  • CCC1C2=C(3(O1)CC(=O)O3)C(=O)C4=C(C2=O)C(=CC=C4)O
Properties
Chemical formula C18H16O6
Molar mass 328.320 g·mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references
Chemical compound

Frenolicin B is an antibiotic and antitumor agent with the molecular formula C18H16O6 which is produced by the bacterium Streptomyces roseofulvus. Frenolicin B is a selective inhibitor of glutaredoxin 3 and peroxiredoxin 1.

References

  1. ^ "Frenolicin B". Pubchem.ncbi.NLM.nih.gov.
  2. Bycroft, Barrie W.; Payne, David J. (9 August 2013). Dictionary of Antibiotics and Related Substances: with CD-ROM, Second Edition. CRC Press. p. 845. ISBN 978-1-4822-8215-3.
  3. Iwai, Yuzuru; Kora, Akiko; Takahashi, Yoko; Hayashi, Takako; Awaya, Juichi; Masuma, Rokurou; Oiwa, Ruiko; Omura, Satoshi (1978). "Production of deoxyfrenolicin and a new antibiotic, frenolicin B by Streptomyces roseofulvus strain AM-3867". The Journal of Antibiotics. 31 (10): 959–965. doi:10.7164/antibiotics.31.959. PMID 711620.
  4. Huang, Canhua; Zhang, Yuanyuan (25 April 2021). Oxidative Stress: Human Diseases and Medicine. Springer Nature. p. 249. ISBN 978-981-16-0522-2.
  5. Ye, Q; Zhang, Y; Cao, Y; Wang, X; Guo, Y; Chen, J; Horn, J; Ponomareva, LV; Chaiswing, L; Shaaban, KA; Wei, Q; Anderson, BD; St Clair, DK; Zhu, H; Leggas, M; Thorson, JS; She, QB (21 March 2019). "Frenolicin B Targets Peroxiredoxin 1 and Glutaredoxin 3 to Trigger ROS/4E-BP1-Mediated Antitumor Effects". Cell Chemical Biology. 26 (3): 366–377.e12. doi:10.1016/j.chembiol.2018.11.013. PMC 6557261. PMID 30661989.

Further reading

  • Fitzgerald, Jay Thomas (2012). Engineering of Biosynthetic Pathways to the Type II Polyketides Frenolicin B and A-74528. Stanford University.
  • ApSimon, John (16 April 1992). The Total Synthesis of Natural Products, Volume 8. John Wiley & Sons. p. 345. ISBN 978-0-471-54507-1.
  • Negishi, Ei-ichi; Meijere, Armin de (24 November 2003). Handbook of Organopalladium Chemistry for Organic Synthesis. John Wiley & Sons. p. 2385. ISBN 978-0-471-47381-7.
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