Chaetochromin

Chaetochromin

Clinical data
Other names	4548-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	75514-37-3
PubChem CID	53277
ChemSpider	48120
UNII	YME4GS90I1
ChEMBL	ChEMBL162783
CompTox Dashboard (EPA)	DTXSID10910964
Chemical and physical data
Formula	C30H26O10
Molar mass	546.528 g·mol−1
3D model (JSmol)	Interactive image
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. 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, and its interaction with the insulin receptor was identified in 2014.

Stereochemistry

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

See also

• Anti-diabetic medication