LIPID MAPS

Structure Database (LMSD)

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Common Name

Hypericin

Systematic Name

Synonyms

LM ID

LMPK13040001

Formula

C₃₀H₁₆O₈

Exact Mass

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504.08452

Status

Curated

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Classification

Biological Context

An anthroquinone derivative that is naturally found in the flower of H. perforatum (St. John’s wort) and has antidepressant, antiviral, and anticancer activities.^1,2 Hypericin inhibits neuronal uptake of serotonin, norepinephrine, dopamine, GABA and L-glutamate, contributing to its antidepressant effects.³ It exerts broad spectrum phototoxic affects (IC50 = 140 - 1,570 nM) through induction of apoptotic signaling and formation of reactive oxygen species (ROS) in cancer cells.⁴ Hypericin also has in vitro activity, which can be enhanced with photo-activation, against a variety of viruses including HIV, influenza virus, hepatitis C, murine cytolomegalovirus, and herpes viruses.⁵

This information has been provided by Cayman Chemical

References

1. Butterweck, V., Christoffel, V., Nahrstedt, A., et al. Step by step removal of hyperforin and hypericin: Activity profile of different Hypericum preparations in behavioral models. Life Sci. 73(5), 627-639 (2003).

2. Jendželovská, Z., Jendželovský, R., Kuchárová, B., et al. Hypericin in the light and in the dark: Two sides of the same coin. Front. Plant Sci. 7(560), (2016).

3. Wölfle, U., Seelinger, G., and Schempp, C.M. Topical application of St. John’s wort (Hypericum perforatum). Planta Med. 80(2-3), 109-120 (2014).

4. Momekov, G.F., D., Zheleva-Dimitrova, D., Nedialkov, P., et al. Cytotoxic effects of hyperatomarin, a prenylated phloroglucinol from Hypericum annulatum Moris subsp. annulatum, in a panel of malignant cell lines. Phytomedicine 15(11), 1010-1015 (2008).

5. Jacobson, J.M., Feinman, L., Liebes, L., et al. Pharmacokinetics, safety, and antiviral effects of hypericin, a derivative of St. John’s wort plant, in patients with chronic hepatitis C virus infection. Antimicrob. Agents and Chemother. 45(2), 517-524 (2001).

String Representations

InChiKey (Click to copy)

BTXNYTINYBABQR-UHFFFAOYSA-N

InChi (Click to copy)

InChI=1S/C30H16O8/c1-7-3-9(31)19-23-15(7)16-8(2)4-10(32)20-24(16)28-26-18(12(34)6-14(36)22(26)30(20)38)17-11(33)5-13(35)21(29(19)37)25(17)27(23)28/h3-6,31-36H,1-2H3

SMILES (Click to copy)

C12C3=C4C(=O)C5C(=CC(C)=C(C6=C(C)C=C(O)C7C(C8C(=CC(O)=C(C3=C(O)C=C4O)C=8C=1C6=7)O)=O)C2=5)O