Frenolicin B

Frenolicin B
Names
	IUPAC name (11R,15R,17R)-4-Hydroxy-17-propyl-12,16-dioxatetracyclo[8.7.0.03,8.011,15]heptadeca-1(10),3(8),4,6-tetraene-2,9,13-trione
Identifiers
CAS Number	68930-68-7 ;
3D model (JSmol)	Interactive image;
Beilstein Reference	6436493
ChEBI	CHEBI:48201;
ChEMBL	ChEMBL474390;
ChemSpider	143304;
PubChem CID	163292;
UNII	385375GE9Y;
CompTox Dashboard (EPA)	DTXSID10219000 ;
	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/s1 Key: AVCPRTNVVRPELB-YRUZYCQGSA-N;
	SMILES CCC[C@@H]1C2=C([C@@H]3[C@H](O1)CC(=O)O3)C(=O)C4=C(C2=O)C(=CC=C4)O;
Properties
Chemical formula	C18H16O6
Molar mass	328.320 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

Frenolicin B is an antibiotic and antitumor agent with the molecular formula C₁₈H₁₆O₆ which is produced by the bacterium Streptomyces roseofulvus.^[2]^[1]^[3] Frenolicin B is a selective inhibitor of glutaredoxin 3 and peroxiredoxin 1.^[4]^[5]

References

^ ^a ^b "Frenolicin B". Pubchem.ncbi.NLM.nih.gov.
^ 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.
^ 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.
^ Huang, Canhua; Zhang, Yuanyuan (25 April 2021). Oxidative Stress: Human Diseases and Medicine. Springer Nature. p. 249. ISBN 978-981-16-0522-2.
^ 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.

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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