Structure via PubChem · Public domain (PubChem)
hypericin
Sign in to saveAlso known as 1:6:8:10:11:13-hexahydroxy-3:4-dimethyl-meso-naphthodianthrene-7:14-dione, hypericum red
Hypericin is a carbopolycyclic compound derived from bisanthene with antidepressant properties, found in various Hypericum species, and is being studied for treating cutaneous T-cell lymphoma.
Chemical data
- Formula
- C30H16O8
- Molecular weight
- 504.4 g/mol
- IUPAC name
- 5,7,11,18,22,24-hexahydroxy-13,16-dimethyloctacyclo[13.11.1.12,10.03,8.04,25.019,27.021,26.014,28]octacosa-1(27),2(28),3,5,7,10,12,14,16,18,21,23,25-tridecaene-9,20-dione
- SMILES
- CC1=CC(=C2C3=C4C5=C(C(=CC(=C5C2=O)O)O)C6=C7C4=C8C(=C13)C(=CC(=C8C(=O)C7=C(C=C6O)O)O)C)O
- InChIKey
- BTXNYTINYBABQR-UHFFFAOYSA-N
- XLogP
- 6.9
- Polar surface area
- 156 Ų
- H-bond donors
- 6
- H-bond acceptors
- 8
- Formal charge
- 0
via PubChem
Research
1,653 papers- Hypericin: A natural anthraquinone as promising therapeutic agent.Phytomedicine : international journal of phytotherapy and phytopharmacology · 2023
- Hypericin in photobiological assays: An overview.Photodiagnosis and photodynamic therapy · 2021
- Hypericin-mediated photodynamic therapy for the treatment of cancer: a review.The Journal of pharmacy and pharmacology · 2021
- Hypericin as a promising natural bioactive naphthodianthrone: A review of its pharmacology, pharmacokinetics, toxicity, and safety.Phytotherapy research : PTR · 2023
- Hypericin and its anticancer effects: From mechanism of action to potential therapeutic application.Phytomedicine : international journal of phytotherapy and phytopharmacology · 2022
via PubMed
Wikidata facts
- Mass
- 504.084517
Show 3 more facts
- chemical formula
- C₃₀H₁₆O₈
- canonical SMILES
- CC1=CC(=C2C3=C1C4=C5C(=C(C=C4C)O)C(=O)C6=C(C=C(C7=C6C5=C3C8=C7C(=CC(=C8C2=O)O)O)O)O)O
- Commons category
- Hypericin
via Wikidata · CC0
~2 min read
Article
1 sectionsContents
- References
Hypericin is a carbopolycyclic compound derived from bisanthene with antidepressant properties, found in various Hypericum species, and is being studied for treating cutaneous T-cell lymphoma.
Opinions differ on the extent to which hypericin exhibits antidepressant effects. According to some scholars, hypericin, along with other active compounds in Hypericum perforatum (St. John’s wort), contributes to the antidepressant effects of the total plant extract. According to others, hypericin does not significantly inhibit monoamine oxidase and thus is unlikely to account for the antidepressant effects of Hypericum extract. While another hypericin shows affinity mainly for NMDA receptors, suggesting that other plant constituents likely play a more significant role in its antidepressant effects.