Chaetochromin

Chaetochromin
Clinical data
Other names4548-G05
Identifiers
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
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC30H26O10
Molar mass546.528 g·mol−1
3D model (JSmol)
SMILES
  • CC1C(Oc2cc3c(c(cc(c3c4c5cc6c(c(c5c(cc4O)O)O)C(=O)C(C(O6)C)C)O)O)c(c2C1=O)O)C
InChI
  • InChI=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
  • Key:RHNVLFNWDGWACV-UHFFFAOYSA-N

Chaetochromin, also known as 4548-G05, is an orally active, small-molecule, selective agonist of the insulin receptor.[1] It has potent and long-lasting antidiabetic activity in vivo in mice.[1] 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.[1] It was discovered in 1981 in Chaetomium gracile fungi,[2] and its interaction with the insulin receptor was identified in 2014.[1]

Stereochemistry

Chaetochromin A and B are stereoisomers of this structure, while chaetochromin C and D are related but different compounds.[3] It is not known whether the insulin mimetic effect was found in chaetochromin A or B, or in a mixture.[1]

See also

References

  1. 1 2 3 4 5 Qiang G, Xue S, Yang JJ, Du G, Pang X, Li X, Goswami D, Griffin PR, Ortlund EA, Chan CB, Ye K (2014). "Identification of a small molecular insulin receptor agonist with potent antidiabetes activity". Diabetes. 63 (4): 1394–409. doi:10.2337/db13-0334. PMC 3964510. PMID 24651808.
  2. ↑ Sekita, S; Yoshihira, K; Natori, S; Udagawa, S; Muroi, T; Sugiyama, Y; Kurata, H; Umeda, M (1981). "Mycotoxin production by Chaetomium spp. And related fungi". Canadian Journal of Microbiology. 27 (8): 766–72. doi:10.1139/m81-119. PMID 7296410.
  3. ↑ Pubchem: Chaetochromin.
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