THC Science

Ascofuranone
Names
	IUPAC name 5-chloro-3-[(2E,6E)-7-[(2S)-5,5-dimethyl-4-oxo-tetrahydrofuran-2-yl]-3-methyl-octa-2,6-dienyl]-2,4-dihydroxy-6-methyl-benzaldehyde
	Other names Ascofuranon
Identifiers
CAS Number	38462-04-3;
3D model (JSmol)	Interactive image;
ChemSpider	4939184 ;
PubChem CID	6434242;
CompTox Dashboard (EPA)	DTXSID60903967 ;
	InChI InChI=1S/C23H29ClO5/c1-13(7-6-8-14(2)18-11-19(26)23(4,5)29-18)9-10-16-21(27)17(12-25)15(3)20(24)22(16)28/h8-9,12,18,27-28H,6-7,10-11H2,1-5H3/b13-9+,14-8+/t18-/m0/s1 Key: VGYPZLGWVQQOST-JUERRSSISA-N ; InChI=1/C23H29ClO5/c1-13(7-6-8-14(2)18-11-19(26)23(4,5)29-18)9-10-16-21(27)17(12-25)15(3)20(24)22(16)28/h8-9,12,18,27-28H,6-7,10-11H2,1-5H3/b13-9+,14-8+/t18-/m0/s1 Key: VGYPZLGWVQQOST-JUERRSSIBJ;
	SMILES O=Cc1c(O)c(c(O)c(Cl)c1C)C/C=C(/CC/C=C(\C)[C@H]2OC(C(=O)C2)(C)C)C;
Properties
Chemical formula	C23H29ClO5
Molar mass	420.93 g·mol−1
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

Ascofuranone is an antibiotic produced by the fungus Ascochyta visiae^[1] that inhibits the Trypanosoma brucei alternative oxidase and is a lead compound in efforts to produce other drugs targeting this enzyme for the treatment of sleeping sickness.^[2] The compound is effective both in vitro cell culture and in infections in mice.^[1]

Ascofuranone has also been reported to have anti-tumor activity,^[3] and modulate the immune system.^[4]

References

^ ^a ^b Yabu Y, Yoshida A, Suzuki T, Nihei C, Kawai K, Minagawa N, Hosokawa T, Nagai K, Kita K, Ohta N (2003). "The efficacy of ascofuranone in a consecutive treatment on Trypanosoma brucei brucei in mice". Parasitol. Int. 52 (2): 155–64. doi:10.1016/S1383-5769(03)00012-6. PMID 12798927.{{cite journal}}: CS1 maint: multiple names: authors list (link)
^ Minagawa N, Yabu Y, Kita K, Nagai K, Ohta N, Meguro K, Sakajo S, Yoshimoto A (1997). "An antibiotic, ascofuranone, specifically inhibits respiration and in vitro growth of long slender bloodstream forms of Trypanosoma brucei brucei". Mol. Biochem. Parasitol. 84 (2): 271–80. doi:10.1016/S0166-6851(96)02797-1. PMID 9084049.{{cite journal}}: CS1 maint: multiple names: authors list (link)
^ Magae J, Hayasaki J, Matsuda Y, Hotta M, Hosokawa T, Suzuki S, Nagai K, Ando K, Tamura G (1988). "Antitumor and antimetastatic activity of an antibiotic, ascofuranone, and activation of phagocytes". J. Antibiot. 41 (7): 959–65. PMID 3417568.{{cite journal}}: CS1 maint: multiple names: authors list (link)
^ Magae J, Suzuki S, Nagai K, Yamasaki M, Ando K, Tamura G (1986). "In vitro effects of an antitumor antibiotic, ascofuranone, on the murine immune system". Cancer Res. 46 (3): 1073–8. PMID 3080231.{{cite journal}}: CS1 maint: multiple names: authors list (link)

@@ Line 1: / Line 1: @@
 {{chembox
+| verifiedrevid = 399533067
 |   Name = Ascofuranone
 |   ImageFile = Ascofuranone structure.png
@@ Line 9: / Line 10: @@
 | Section1 = {{Chembox Identifiers
 |   SMILES = O=Cc1c(O)c(c(O)c(Cl)c1C)C/C=C(/CC/C=C(\C)[C@H]2OC(C(=O)C2)(C)C)C
+|   ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
-|   ChemSpiderID = 4939184
+| ChemSpiderID = 4939184
 |   PubChem = 6434242
 |   InChI = 1/C23H29ClO5/c1-13(7-6-8-14(2)18-11-19(26)23(4,5)29-18)9-10-16-21(27)17(12-25)15(3)20(24)22(16)28/h8-9,12,18,27-28H,6-7,10-11H2,1-5H3/b13-9+,14-8+/t18-/m0/s1
 |   InChIKey = VGYPZLGWVQQOST-JUERRSSIBJ
+|   StdInChI_Ref = {{stdinchicite|correct|chemspider}}
-|   StdInChI = 1S/C23H29ClO5/c1-13(7-6-8-14(2)18-11-19(26)23(4,5)29-18)9-10-16-21(27)17(12-25)15(3)20(24)22(16)28/h8-9,12,18,27-28H,6-7,10-11H2,1-5H3/b13-9+,14-8+/t18-/m0/s1
+| StdInChI = 1S/C23H29ClO5/c1-13(7-6-8-14(2)18-11-19(26)23(4,5)29-18)9-10-16-21(27)17(12-25)15(3)20(24)22(16)28/h8-9,12,18,27-28H,6-7,10-11H2,1-5H3/b13-9+,14-8+/t18-/m0/s1
+| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
 | StdInChIKey = VGYPZLGWVQQOST-JUERRSSISA-N
 | CASNo =38462-04-3