Viridin

Viridin
Names
	Preferred IUPAC name (1S,2S,11bR)-1-Hydroxy-2-methoxy-11b-methyl-1,7,8,11b-tetrahydrocyclopenta[7,8]phenanthro[10,1-bc]furan-3,6,9(2H)-trione
Identifiers
CAS Number	3306-52-3 ;
3D model (JSmol)	Interactive image;
ChEMBL	ChEMBL2158159;
ChemSpider	85065;
ECHA InfoCard	100.019.989
EC Number	221-987-6;
PubChem CID	94257;
UNII	X5KJO207MO ;
CompTox Dashboard (EPA)	DTXSID00889372 ;
	InChI InChI=1S/C20H16O6/c1-20-11-5-3-8-9(4-6-12(8)21)13(11)16(23)17-14(20)10(7-26-17)15(22)18(25-2)19(20)24/h3,5,7,18-19,24H,4,6H2,1-2H3/t18-,19-,20-/m1/s1 Key: YEIGUXGHHKAURB-VAMGGRTRSA-N;
	SMILES C[C@]12[C@@H]([C@@H](C(=O)C3=COC(=C31)C(=O)C4=C2C=CC5=C4CCC5=O)OC)O;
Properties
Chemical formula	C20H16O6
Molar mass	352.337 g mol−1
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). (what is ?) Infobox references

Viridin is an antifungal metabolite of Gliocladium virens that was first reported in 1945.^[1] Belonging to a class of molecules known as furanosteroids, it has a characteristic highly strained electrophilic furan ring fused between C-4 and C-6 of the steroid framework. Members of this family, including wortmannin, are known to be potent, irreversible covalent inhibitors of phosphoinositide 3-kinases (PI3Ks).^[2]

^ BRIAN, P. W.; MCGOWAN, J. G. (4 August 1945). "Viridin: a Highly Fungistatic Substance Produced by Trichoderma viride". Nature. 156 (3953): 144–145. Bibcode:1945Natur.156..144B. doi:10.1038/156144a0. S2CID 4077467.
^ Yano, H; Nakanishi, S; Kimura, K; Hanai, N; Saitoh, Y; Fukui, Y; Nonomura, Y; Matsuda, Y (Dec 5, 1993). "Inhibition of histamine secretion by wortmannin through the blockade of phosphatidylinositol 3-kinase in RBL-2H3 cells". The Journal of Biological Chemistry. 268 (34): 25846–56. doi:10.1016/S0021-9258(19)74466-4. PMID 7503989.

[1] BRIAN, P. W.; MCGOWAN, J. G. (4 August 1945). "Viridin: a Highly Fungistatic Substance Produced by Trichoderma viride". Nature. 156 (3953): 144–145. Bibcode:1945Natur.156..144B. doi:10.1038/156144a0. S2CID 4077467.

[2] Yano, H; Nakanishi, S; Kimura, K; Hanai, N; Saitoh, Y; Fukui, Y; Nonomura, Y; Matsuda, Y (Dec 5, 1993). "Inhibition of histamine secretion by wortmannin through the blockade of phosphatidylinositol 3-kinase in RBL-2H3 cells". The Journal of Biological Chemistry. 268 (34): 25846–56. doi:10.1016/S0021-9258(19)74466-4. PMID 7503989.

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