andrographolide andrographolide andrographolide is a labdane diterpenoid that has been isolated from the stem and leaves of andrographis paniculata. andrographolide is an extremely bitter substance. andrographolide names iupac name 3-ethylidene]dihydro-4-hydroxy-2(3h)-furanone identifiers cas number 5508-58-7 y 3d model (jsmol) interactive imageinteractive image chebi chebi:65408 n chembl chembl186141 n chemspider 16735664 y echa infocard 100.024.411 pubchem cid 5318517 unii 410105jhgr y 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 ykey: bojkultulysras-fntfrydesa-n yinchi=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,1,4,6-11h2,2-3h3key: bojkultulysras-uhfffaoyabinchi=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/s1key: bojkultulysras-fntfrydeby smiles o=c3occ(o)c3=ccc1\c(=c)ccc2c(c)(co)c(o)ccc12coc3coc(=o)\c3=c\c1c(=c)cc2c(c)(co)(o)cc12c 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 , 100 kpa). n verify (what is yn ?) infobox references 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. biosynthesis while andrographolide is a relatively simple diterpene lactone, the biosynthesis by andrographis paniculata was determined in the 2010s. andrographolide is a member of the isoprenoid family of natural products. the precursors to isoprenoid biosynthesis, isopentenyl pyrophosphate (ipp) and dimethylallyl pyrophosphate (dmapp), can be synthesized through either the mevalonic acid pathway (mva) or deoxyxylulose pathway (dxp). through selective c13 labeling of the precursors to both the mva and dxp pathways, it was determined that the majority of the andrographolide precursors are synthesized through the dxp pathway. there are a small portion of andrographolide precursors synthesized through the mva pathway. the biosynthesis of andrographolide begins with the addition of ipp to dmapp, which forms geranyl pyrophosphate. another molecule of ipp is then added, yielding farnesyl pyrophosphate (fpp). the final ipp molecule is added to the fpp to complete the backbone of the diterpene. the double bond originating from dmapp is oxidized to an epoxide prior to the ring closing cascade that forms two six-membered rings. a series of oxidations form a five-membered lactone in addition to adding on the alcohol groups. the order of these post-synthetic modifications is not entirely known. biosynthesis of andrographolide