| Synonyms |
Andrographolide, dehydro-; Deoxy-11,12-didehydroandrographolide; (3E)-3-[2-[(1S,4aS,5R,6R,8aS)-Decahydro-6-hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-2-methylene-1-naphthalenyl]ethylidene]-2(3H)-furanone; 14-Deoxy-11-dehydroandrographolide |
| IUPAC Name |
(3E)-3-[2-[(1S,4aS,5R,6R,8aS)-6-hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-2-methylidene-3,4,4a,6,7,8-hexahydro-1H-naphthalen-1-yl]ethylidene]furan-2-one |
| Molecular Weight |
332.43 |
| Molecular Formula |
C20H28O4 |
| Canonical SMILES |
CC12CCC(C(C1CCC(=C)C2CC=C3C=COC3=O)(C)CO)O |
| InChI |
InChI=1S/C20H28O4/c1-13-4-7-16-19(2,10-8-17(22)20(16,3)12-21)15(13)6-5-14-9-11-24-18(14)23/h5,9,11,15-17,21-22H,1,4,6-8,10,12H2,2-3H3/b14-5+/t15-,16-,17+,19-,20-/m0/s1 |
| InChIKey |
YIIRVUDGRKEWBV-CZUXAOBFSA-N |
| Boiling Point |
512.8±50.0 °C at 760 mmHg |
| Flash Point |
178.3±23.6 °C |
| Purity |
>98% |
| Density |
1.2±0.1 g/cm3 |
| Solubility |
10 mM in ethanol |
| Appearance |
White powder |
| Application |
Dehydroandrographolide is a natural diterpenoid found in Andrographis paniculata and possesses activity against hepatitis B virus DNA replication. |
| Shelf Life |
As supplied, 2 years from the QC date provided on the Certificate of Analysis, when stored properly |
| Storage |
-20°C Freeze |
| Complexity |
605 |
| Exact Mass |
332.19875937 |
| Index Of Refraction |
1.584 |
| In Vitro |
Dehydroandrographolide inhibits TMEM16A chloride currents in Fisher rat thyroid (FRT) cells that are transfected stably with human TMEM16A and in TMEM16A-overexpressed SW620 cells but does not alter cystic fibrosis transmembrane conductance regulator (CFTR) chloride currents. Further functional studies show that dehydroandrographolide suppresses the proliferation of SW620 cells in a dose- and time-dependent manner using MTT assays. Dehydroandrographolide significantly inhibits migration and invasion of SW620 cells as detected by wound-healing and transwell assays. Moreover, treatment of SW620 cells with dehydroandrographolide leads to a decrease in TMEM16A protein levels but has no effect on TMEM16A mRNA levels. Dehydroandrographolide induces Autophagy in human oral cancer cells by modulating p53 expression, activating JNK1/2, and inhibiting Akt and p38. Dehydroandrographolide is an iNOS inhibitor and an antiinflammatory and antiviral agent. |
| In Vivo |
Administration of dehydroandrographolide effectively suppresses the tumor formation in the oral carcinoma xenograft model in vivo. |
| PSA |
86.99000 |
| Target |
Influenza Virus |
| Vapor Pressure |
0.0±3.0 mmHg at 25°C |
| XLogP3-AA |
3.4 |
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