Structure via PubChem · Public domain (PubChem)
andrographolide
Sign in to saveAndrographolide is a labdane diterpenoid that has been isolated from the stem and leaves of Andrographis paniculata. Andrographolide is an extremely bitter substance.
Chemical data
- Formula
- C20H30O5
- Molecular weight
- 350.4 g/mol
- IUPAC name
- (3E,4S)-3-[2-[(1R,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]-4-hydroxyoxolan-2-one
- SMILES
- C[C@@]12CC[C@H]([C@@]([C@H]1CCC(=C)[C@H]2C/C=C/3\[C@@H](COC3=O)O)(C)CO)O
- InChIKey
- BOJKULTULYSRAS-OTESTREVSA-N
- XLogP
- 2.2
- Polar surface area
- 87 Ų
- H-bond donors
- 3
- H-bond acceptors
- 5
- Formal charge
- 0
via PubChem
Research
1,824 papers- Andrographolide: A review of its pharmacology, pharmacokinetics, toxicity and clinical trials and pharmaceutical researches.Phytotherapy research : PTR · 2022
- Andrographolide: Synthetic Methods and Biological Activities.Mini reviews in medicinal chemistry · 2020
- Andrographolide: A Review of Analytical Methods.Journal of chromatographic science · 2021
- Andrographolide: Chemical modification and its effect on biological activities.Bioorganic chemistry · 2020
- Andrographolide alleviates Parkinsonism in MPTP-PD mice via targeting mitochondrial fission mediated by dynamin-related protein 1.British journal of pharmacology · 2019
via PubMed
Wikidata facts
- Named after
- Andrographis paniculata
- Mass
- 350.2093240599999
Show 6 more facts
- canonical SMILES
- O=C3OCC(O)C3=CCC1\C(=C)CCC2C(C)(CO)C(O)CCC12C
- chemical formula
- C₂₀H₃₀O₅
- found in taxon
- Biancaea decapetala
- subject has role
- platelet aggregation inhibitors
- isomeric SMILES
- C[C@@]12CC[C@H]([C@@]([C@H]1CCC(=C)[C@H]2C/C=C/3[C@@H](COC3=O)O)(C)CO)O
- has characteristic
- bitterness
via Wikidata · CC0
~3 min read
Encyclopedic overview
4 sectionsContents
- Biosynthesis
- Research
- See also
- 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.
Excerpted from Wikipedia’s “andrographolide” article, available under the CC BY-SA 4.0 licence.
Gallery (2)
Available in 10 languages
via Wikidata sitelinks · CC0