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Hypericin

Hypericin structure

CAS No:
548-04-9
Formula:
C30H16O8
Chemical Name:
Hypericin
Synonyms:
Phenanthro[1,10,9,8-opqra]perylene-7,14-dione,1,3,4,6,8,13-hexahydroxy-10,11-dimethyl-,stereoisomer;stereoisomer of 1,3,4,6,8,13-Hexahydroxy-10,11-dimethylphenanthro[1,10,9,8-opqra]perylene-7,14-dione;Cyclosan;Cyclo-Werol;Hypericin;Hypericum red;1,3,4,6,8,13-Hexahydroxy-10,11-dimethylphenanthro[1,10,9,8-opqra]perylene-7,14-dione P-conformer;NSC 407313;Hyperflav;345224-62-6;935869-37-7;693273-27-7
Categories:
Biochemical Engineering > Biosynthetic Natural Products

Description

Hypericin is a photosensitive antiviral with anticancer and antidepressant agent derived from Hypericum perforatum. It can inhibit tyrosine kinases with IC50 of 7.5 μM. IC50: 7.5 uMIn vitro:The photosensitive of hypericin can induce both apoptosis and necrosis in a concentration and light dose-dependent fashion. PDT with hypericin results in the activation of multiple pathways that can either promote or counteract the cell death program. It can effect cytotoxic to tumor cells by visible

Hypericin is a carbopolycyclic compound. It has a role as an antidepressant. It derives from a hydride of a bisanthene.|Hypericin is an anthraquinone derivative that is naturally found in the yellow flower of Hypericum perforatum (St. John's wort) with antidepressant, potential antiviral, antineoplastic and immunostimulating activities. Hypericin appears to inhibit the neuronal uptake of serotonin, norepinephrine, dopamine, gamma-amino butyric acid (GABA) and L-glutamate, which may contribute to its antidepressant effect. Hypericin may also prevent the replication of encapsulated viruses probably due to inhibition of the assembly and shedding of virus particles in infected cells. This agent also exerts potent phototoxic effects by triggering apoptotic signaling that results in formation of reactive oxygen species.

Hypericin Basic Attributes

Molecular Weight：

504.44

Exact Mass：

504.44

BRN：

1917913

EC Number：

208-941-0

UNII：

7V2F1075HD

NSC Number：

622946|407313

DSSTox ID：

DTXSID40203270

NCI Thesaurus Code：

C37456

HScode：

2914700090

Characteristics

PSA：

156

XLogP3：

8.39

Appearance：

black powder

Density：

1.9±0.1 g/cm3

Melting Point：

299-301°C

Boiling Point：

930.1±65.0 °C at 760 mmHg

Flash Point：

530.1±30.8 °C

Refractive Index：

2.131

Water Solubility：

soluble in ethanol, dimethyl sulfoxide, methanol, acetone, ethylmethylketone, pyridine and sodium hydroxide. Insoluble in water.1 M NaOH: 10 mg/mL

Storage Conditions：

Store at +4°C

Safety Information

Transport codes：

2811

wgk germany：

hazard class code：

22-40-43

safety instructions：

22-36-36/37

RTECS Number：

SF8472000

Marks：

Precautionary statement(s)：

P280-P301 + P312 + P330

Hazard Statements：

H302-H317

GHS Classification：

|Danger|H301 (81.25%): Toxic if swallowed [Danger Acute toxicity, oral]|P261, P264, P270, P272, P280, P301+P310, P301+P312, P302+P352, P321, P330, P333+P313, P363, P405, and P501|Aggregated GHS information provided by 48 companies from 6 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Drug Information

MeSH：

Agents that suppress immune function by one of several mechanisms of action. Classical cytotoxic immunosuppressants act by inhibiting DNA synthesis. Others may act through activation of T-CELLS or by inhibiting the activation of HELPER CELLS. While immunosuppression has been brought about in the past primarily to prevent rejection of transplanted organs, new applications involving mediation of the effects of INTERLEUKINS and other CYTOKINES are emerging. (See all compounds classified as Immunosuppressive Agents.)|Mood-stimulating drugs used primarily in the treatment of affective disorders and related conditions. Several MONOAMINE OXIDASE INHIBITORS are useful as antidepressants apparently as a long-term consequence of their modulation of catecholamine levels. The tricyclic compounds useful as antidepressive agents (ANTIDEPRESSIVE AGENTS, TRICYCLIC) also appear to act through brain catecholamine systems. A third group (ANTIDEPRESSIVE AGENTS, SECOND-GENERATION) is a diverse group of drugs including some that act specifically on serotonergic systems. (See all compounds classified as Antidepressive Agents.)|Compounds or agents that combine with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction. (See all compounds classified as Enzyme Inhibitors.)|Agents used in the prophylaxis or therapy of VIRUS DISEASES. Some of the ways they may act include preventing viral replication by inhibiting viral DNA polymerase; binding to specific cell-surface receptors and inhibiting viral penetration or uncoating; inhibiting viral protein synthesis; or blocking late stages of virus assembly. (See all compounds classified as Antiviral Agents.)|Drugs used to potentiate the effectiveness of radiation therapy in destroying unwanted cells. (See all compounds classified as Radiation-Sensitizing Agents.)|Substances that inhibit or prevent the proliferation of NEOPLASMS. (See all compounds classified as Antineoplastic Agents.)

MeSH Entry Terms：

hypericin

Hypericin Use and Manufacturing

Uses

Hypericin is an extract from Hypericum perforatum L. hypericaceae (also known as St. John~"s wort) and is believed to be an antibiotic/antiviral, specifically acting as a kinase inhibitor.

Use Classification：

Polyketides [PK] -> Aromatic polyketides [PK13] -> Anthracenes and phenanthrenes [PK1304]

Computed Properties

Molecular Weight:504.4
XLogP3:5.7
Hydrogen Bond Donor Count:6
Hydrogen Bond Acceptor Count:8
Exact Mass:504.08451746
Monoisotopic Mass:504.08451746
Topological Polar Surface Area:156
Heavy Atom Count:38
Complexity:1090
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

Drug Function and Efficacy

Hypericum Perforatum, commonly known as St. John's Wort, is widely recognized for its antidepressant and anti-inflammatory effects, primarily due to hypericin and hyperforin content.

This ingredient has been used in drugs with the following functions (note: it does not mean that the ingredient itself has the following health functions)

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Guide of Hypericin

Description
Basic Attributes
Characteristics
Safety Information
Drug Information
Use and Manufacturing
Computed Properties
Drug Function and Efficacy
Related Drugs
Recommended Suppliers
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