Andrographolide

Andrographolide
Names
	IUPAC name 3-[2-[Decahydro-6-hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-2-methylene-1-napthalenyl]ethylidene]dihydro-4-hydroxy-2(3H)-furanone
Identifiers
CAS Number	5508-58-7 ;
3D model (JSmol)	Interactive image; Interactive image;
ChEBI	CHEBI:65408 ;
ChEMBL	ChEMBL186141 ;
ChemSpider	16735664 ;
ECHA InfoCard	100.024.411
PubChem CID	5318517;
UNII	410105JHGR ;
CompTox Dashboard (EPA)	DTXSID3045980 ;
	InChI InChI=1S/C20H30O5/c1-12-4-7-16-19(2,9-8-17(23)20(16,3)11-21)14(12)6-5-13-15(22)10-25-18(13)24/h5,14-17,21-23H,1,4,6-11H2,2-3H3/b13-5+/t14-,15?,16+,17-,19+,20?/m1/s1 Key: BOJKULTULYSRAS-FNTFRYDESA-N ; InChI=1/C20H30O5/c1-12-4-7-16-19(2,9-8-17(23)20(16,3)11-21)14(12)6-5-13-15(22)10-25-18(13)24/h5,14-17,21-23H,1,4,6-11H2,2-3H3 Key: BOJKULTULYSRAS-UHFFFAOYAB; InChI=1/C20H30O5/c1-12-4-7-16-19(2,9-8-17(23)20(16,3)11-21)14(12)6-5-13-15(22)10-25-18(13)24/h5,14-17,21-23H,1,4,6-11H2,2-3H3/b13-5+/t14-,15?,16+,17-,19+,20?/m1/s1 Key: BOJKULTULYSRAS-FNTFRYDEBY;
	SMILES O=C3OCC(O)C3=CCC1\C(=C)CCC2C(C)(CO)C(O)CCC12C; OC3COC(=O)\C3=C\C[C@@H]1C(=C)CC[C@@H]2C(C)(CO)[C@H](O)CC[C@@]12C;
Properties
Chemical formula	C20H30O5
Molar mass	350.455 g·mol−1
Appearance	Rhombic prisms or plates from ethanol or methanol
Density	1.2317 g/cm3
Melting point	230 to 231 °C (446 to 448 °F; 503 to 504 K)
Solubility in water	Sparingly soluble
Related compounds
Related labdanes	14-deoxyandrographolide
Related compounds	Xiyanping
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

Andrographolide is a labdane diterpenoid that has been isolated from the stem and leaves of Andrographis paniculata. Andrographolide is an extremely bitter substance.

Andrographolide has been studied for its effects on cell signaling, immunomodulation, and stroke. Study has shown that andrographolide may bind to a spectrum of protein targets including NF-κB and actin by covalent modification.

Andrographolide is a non-ATP-competitive, substrate-competitive GSK-3β inhibitor. When the substrate concentration is 25μM, the IC₅₀ of andrographolide for GSK-3β is 5.58±0.40μM. When the substrate concentration is increased to 90μM, the IC₅₀ increases to 37.7μM.