Description
Averantin is an anthraquinone fungal metabolite produced by Aspergillus sp. associated with Panax notoginseng. It is a mycotoxic intermediate in the pathway to aflatoxin B1. It displays antifungal activity against Fusariumsolani (pathogenic fungus of P. notoginseng) with minimum inhibitory concentrations of 16-32 ug/mL. It also shows antibacterial activity against Bacillus subtilis with minimum inhibitory concentrations of 16-32 ug/mL.
Synonyms
1,3,6,8-Tetrahydroxy-2-[(1S)-1-hydroxyhexyl]-9,10-anthracenedione; (-)-Averantin; (S)-1,3,6,8-Tetrahydroxy-2-(1-hydroxyhexyl)-9,10-anthracenedione; 9,10-Anthracenedione, 1,3,6,8-tetrahydroxy-2-[(1S)-1-hydroxyhexyl]-; (1'S)-averantin; (S)-(-)-averantin; (S)-averantin
IUPAC Name
1,3,6,8-tetrahydroxy-2-[(1S)-1-hydroxyhexyl]anthracene-9,10-dione
Molecular Formula
C20H20O7
Canonical SMILES
CCCCCC(C1=C(C=C2C(=C1O)C(=O)C3=C(C=C(C=C3C2=O)O)O)O)O
InChI
InChI=1S/C20H20O7/c1-2-3-4-5-12(22)17-14(24)8-11-16(20(17)27)19(26)15-10(18(11)25)6-9(21)7-13(15)23/h6-8,12,21-24,27H,2-5H2,1H3/t12-/m0/s1
InChIKey
WGPOPPKSQRZUTP-LBPRGKRZSA-N
Boiling Point
694.5±34.0°C (Predicted)
Density
1.490±0.06 g/cm3 (Predicted)
Solubility
Soluble in Acetone, Methanol, DMSO, Ethanol, Chloroform
Definition
ChEBI: A tetrahydroxyanthraquinone that is 1,3,6,8-tetrahydroxy-9,10-anthraquinone bearing a 1-hydroxyhexyl substituent at position 2.