Hypericin

Also known as 1:6:8:10:11:13-hexahydroxy-3:4-dimethyl-meso-naphthodianthrene-7:14-dione, hypericum red

Arzneistoff

In the Vinony graph

Vinony's link graph records 205 inbound references to Hypericin, and connects out to DL-glutamic acid, NMDA receptor and pentamidine.

Vinony files it under 3-Hydroxypropenals within hydroxyquinones, Biological pigments and Chembox image size set.

Vinony links it to 22 Wikipedia language editions.

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 Å²
H-bond donors: 6
H-bond acceptors: 8
Formal charge: 0

via PubChem

Drug data · ChEMBL

Max clinical phase: Phase 3
Molecule type: Small molecule
Indications: HIV infection, Cutaneous T-cell lymphoma, mycosis fungoides, psoriasis vulgaris

via ChEMBL · EBI

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 5 more facts

found in taxon: Hypericum aucheri
chemical formula: C₃₀H₁₆O₈
subject has role: enzyme inhibitor
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

Sources (3)

via Wikidata · CC0

Article · Deutsch

Hypericin ist ein rotes Anthrachinon-Derivat und einer der wesentlichen färbenden Bestandteile der Johanniskräuter, insbesondere des Echten Johanniskrauts (Hypericum perforatum). Hypericin wurde als Arzneistoff, hierbei hauptsächlich als Antidepressivum, verwendet. Als Nebenwirkungen der Einnahme wurden phototoxische Reaktionen der Haut, der Augenlinse und der Retina festgestellt; Letzteres kann zur Makuladegeneration führen. Die Anwendung von Hypericin als Antidepressivum ist heute umstritten, da bislang kein Wirksamkeitsnachweis für Hypericin erbracht werden konnte.

Abstract from DBpedia / Wikipedia · CC BY-SA