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)	DTXSID501337172 DTXSID10910964, DTXSID501337172 ;
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;

Chemical compound

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]

References

^ a b c d e Qiang G, Xue S, Yang JJ, Du G, Pang X, Li X, et al. (April 2014). "Identification of a small molecular insulin receptor agonist with potent antidiabetes activity". Diabetes. 63 (4): 1394–1409. doi:10.2337/db13-0334. PMC 3964510. PMID 24651808.
^ Sekita S, Yoshihira K, Natori S, Udagawa S, Muroi T, Sugiyama Y, et al. (August 1981). "Mycotoxin production by Chaetomium spp. and related fungi". Canadian Journal of Microbiology. 27 (8): 766–772. doi:10.1139/m81-119. PMID 7296410.
^ "Chaetochromin". PubChem. U.S. National Library of Medicine.

[pmid24651808-1] Qiang G, Xue S, Yang JJ, Du G, Pang X, Li X, et al. (April 2014). "Identification of a small molecular insulin receptor agonist with potent antidiabetes activity". Diabetes. 63 (4): 1394–1409. doi:10.2337/db13-0334. PMC 3964510. PMID 24651808.

[2] Sekita S, Yoshihira K, Natori S, Udagawa S, Muroi T, Sugiyama Y, et al. (August 1981). "Mycotoxin production by Chaetomium spp. and related fungi". Canadian Journal of Microbiology. 27 (8): 766–772. doi:10.1139/m81-119. PMID 7296410.

[3] "Chaetochromin". PubChem. U.S. National Library of Medicine.

Chaetochromin

Stereochemistry

See also

References