Chaetochromin

{{Short description|Chemical compound}}

{{Drugbox

| drug_name=Chaetochromin A

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| IUPAC_name = 5,5',6,6',8,8'-Hexahydroxy-2,2',3,3'-tetramethyl-2,2',3,3'-tetrahydro-4H,4'H-9,9'-bibenzo[g]chromene-4,4'-dione

| image = Chaetochromin skeletal.svg

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| CAS_number = 75514-37-3

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| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = YME4GS90I1

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| PubChem = 6712966

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| ChemSpiderID = 5144991

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| ChEMBL = 162783

| synonyms = 4548-G05; Chaetochromin A

| C=30 | H=26 | O=10

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| SMILES = C[C@@H]1[C@H](OC2=C(C1=O)C(=C3C(=C2)C(=C(C=C3O)O)C4=C(C=C(C5=C(C6=C(C=C54)O[C@@H]([C@H](C6=O)C)C)O)O)O)O)C

| StdInChI_Ref =

| StdInChI=1S/C30H26O10/c1-9-11(3)39-19-5-13-21(15(31)7-17(33)23(13)29(37)25(19)27(9)35)22-14-6-20-26(28(36)10(2)12(4)40-20)30(38)24(14)18(34)8-16(22)32/h5-12,31-34,37-38H,1-4H3/t9-,10-,11-,12-/m1/s1

| StdInChIKey_Ref =

| StdInChIKey = RHNVLFNWDGWACV-DDHJBXDOSA-N

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Chaetochromin, also known as 4548-G05, is an orally active, small-molecule, selective agonist of the insulin receptor.{{cite journal | vauthors = Qiang G, Xue S, Yang JJ, Du G, Pang X, Li X, Goswami D, Griffin PR, Ortlund EA, Chan CB, Ye K | display-authors = 6 | title = Identification of a small molecular insulin receptor agonist with potent antidiabetes activity | journal = Diabetes | volume = 63 | issue = 4 | pages = 1394–1409 | date = April 2014 | pmid = 24651808 | pmc = 3964510 | doi = 10.2337/db13-0334 }} It has potent and long-lasting antidiabetic activity in vivo in mice. The drug may represent a novel potential therapeutic agent for the treatment of diabetes which is more convenient and tolerable to administer than injected insulin. It was discovered in 1981 in Chaetomium gracile fungi,{{cite journal | vauthors = Sekita S, Yoshihira K, Natori S, Udagawa S, Muroi T, Sugiyama Y, Kurata H, Umeda M | display-authors = 6 | title = Mycotoxin production by Chaetomium spp. and related fungi | journal = Canadian Journal of Microbiology | volume = 27 | issue = 8 | pages = 766–772 | date = August 1981 | pmid = 7296410 | doi = 10.1139/m81-119 }} and its interaction with the insulin receptor was identified in 2014.