Structure Database (LMSD)

Common Name
Hypericin
Systematic Name
Synonyms
LM ID
LMPK13040001
Formula
Exact Mass
Calculate m/z
504.08452
Status
Curated


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

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).

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

Other Databases

Wikipedia
KEGG ID
HMDB ID
CHEBI ID
PubChem CID
Cayman ID

Calculated Physicochemical Properties

Heavy Atoms 38
Rings 8
Aromatic Rings 4
Rotatable Bonds 0
Van der Waals Molecular Volume 415.80
Topological Polar Surface Area 155.52
Hydrogen Bond Donors 6
Hydrogen Bond Acceptors 8
logP 4.59
Molar Refractivity 135.10

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Updated at
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