Structure Database (LMSD)
Common Name
Hypericin
Systematic Name
Synonyms
3D model of Hypericin
Please note: Where there are chiral atoms but the stereochemistry is undefined, the 3D model takes an arbitrary conformation
Classification
Category
Main Class
Sub Class
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
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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