This drug entry is a stub and has not been fully annotated. It is scheduled to be annotated soon.

Identification

Name
Hypericin
Accession Number
DB13014
Type
Small Molecule
Groups
Investigational
Description

Hypericin is under investigation for the treatment of Cutaneous T-cell Lymphoma.

Structure
Thumb
Synonyms
  • hipericina
Categories
UNII
7V2F1075HD
CAS number
548-04-9
Weight
Average: 504.4432
Monoisotopic: 504.084517488
Chemical Formula
C30H16O8
InChI Key
BTXNYTINYBABQR-UHFFFAOYSA-N
InChI
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
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(O)=C2C(=O)C3=C(O)C=C(O)C4=C3C3=C2C1=C1C(C)=CC(O)=C2C(=O)C5=C(O)C=C(O)C4=C5C3=C12

Pharmacology

Indication
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UGlutathione S-transferase A1Not AvailableHuman
UGlutathione S-transferase PNot AvailableHuman
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
(R)-warfarinThe risk or severity of adverse effects can be increased when Hypericin is combined with (R)-warfarin.
(S)-WarfarinThe risk or severity of adverse effects can be increased when Hypericin is combined with (S)-Warfarin.
2-MethoxyethanolThe risk or severity of adverse effects can be increased when 2-Methoxyethanol is combined with Hypericin.
2,5-Dimethoxy-4-ethylthioamphetamineThe risk or severity of adverse effects can be increased when Hypericin is combined with 2,5-Dimethoxy-4-ethylthioamphetamine.
3,4-MethylenedioxyamphetamineThe risk or severity of adverse effects can be increased when 3,4-Methylenedioxyamphetamine is combined with Hypericin.
4-Bromo-2,5-dimethoxyamphetamineThe risk or severity of adverse effects can be increased when 4-Bromo-2,5-dimethoxyamphetamine is combined with Hypericin.
4-hydroxycoumarinThe risk or severity of adverse effects can be increased when Hypericin is combined with 4-hydroxycoumarin.
4-MethoxyamphetamineThe risk or severity of adverse effects can be increased when 4-Methoxyamphetamine is combined with Hypericin.
5-methoxy-N,N-dimethyltryptamineThe risk or severity of adverse effects can be increased when Hypericin is combined with 5-methoxy-N,N-dimethyltryptamine.
7-NitroindazoleThe risk or severity of adverse effects can be increased when 7-Nitroindazole is combined with Hypericin.
Food Interactions
Not Available

References

General References
Not Available
External Links
Human Metabolome Database
HMDB0034271
KEGG Compound
C07606
PubChem Compound
5281051
PubChem Substance
347829150
ChemSpider
4444511
BindingDB
50060874
ChEBI
5835
ChEMBL
CHEMBL286494
Wikipedia
Hypericin

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
1CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections2
3RecruitingTreatmentCutaneous T-Cell Lymphoma (CTCL)1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Not Available
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.00732 mg/mLALOGPS
logP3.92ALOGPS
logP7.7ChemAxon
logS-4.8ALOGPS
pKa (Strongest Acidic)1.39ChemAxon
pKa (Strongest Basic)16.11ChemAxon
Physiological Charge-4ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area155.52 Å2ChemAxon
Rotatable Bond Count0ChemAxon
Refractivity139.31 m3·mol-1ChemAxon
Polarizability50.96 Å3ChemAxon
Number of Rings8ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
MS/MS Spectrum - , negativeLC-MS/MSsplash10-0udi-0000090000-e9cd20b64eba34b7fb1e
MS/MS Spectrum - , positiveLC-MS/MSsplash10-0a4i-0000590000-d6f4544a5f160b2a5b67

Taxonomy

Description
This compound belongs to the class of organic compounds known as benzopyrenes. These are organic compounds containing a benzene fused to a pyrene(benzo[def]phenanthrene) ring system.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Pyrenes
Sub Class
Benzopyrenes
Direct Parent
Benzopyrenes
Alternative Parents
Phenanthro-perylenequinones / Triphenylenes / Chrysenes / Phenanthrols / Anthracenes / Naphthols and derivatives / 1-hydroxy-2-unsubstituted benzenoids / Vinylogous acids / Polyols / Organic oxides
show 1 more
Substituents
Benzo-a-pyrene / Benzo-e-pyrene / Phenanthro-perylenequinone / Perylenequinone / Chrysene / Triphenylene / Phenanthrol / Phenanthrene / Anthracene / 1-naphthol
show 9 more
Molecular Framework
Aromatic homopolycyclic compounds
External Descriptors
carbopolycyclic compound (CHEBI:5835) / Anthracenes and phenanthrenes, Anthrone type (C07606) / Anthracenes and phenanthrenes (LMPK13040001)

Targets

Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Glutathione transferase activity
Specific Function
Conjugation of reduced glutathione to a wide number of exogenous and endogenous hydrophobic electrophiles.
Gene Name
GSTA1
Uniprot ID
P08263
Uniprot Name
Glutathione S-transferase A1
Molecular Weight
25630.785 Da
References
  1. Lu WD, Atkins WM: A novel antioxidant role for ligandin behavior of glutathione S-transferases: attenuation of the photodynamic effects of hypericin. Biochemistry. 2004 Oct 12;43(40):12761-9. [PubMed:15461448]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
S-nitrosoglutathione binding
Specific Function
Conjugation of reduced glutathione to a wide number of exogenous and endogenous hydrophobic electrophiles. Regulates negatively CDK5 activity via p25/p35 translocation to prevent neurodegeneration.
Gene Name
GSTP1
Uniprot ID
P09211
Uniprot Name
Glutathione S-transferase P
Molecular Weight
23355.625 Da
References
  1. Lu WD, Atkins WM: A novel antioxidant role for ligandin behavior of glutathione S-transferases: attenuation of the photodynamic effects of hypericin. Biochemistry. 2004 Oct 12;43(40):12761-9. [PubMed:15461448]

Carriers

Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Toxic substance binding
Specific Function
Serum albumin, the main protein of plasma, has a good binding capacity for water, Ca(2+), Na(+), K(+), fatty acids, hormones, bilirubin and drugs. Its main function is the regulation of the colloid...
Gene Name
ALB
Uniprot ID
P02768
Uniprot Name
Serum albumin
Molecular Weight
69365.94 Da
References
  1. Lu WD, Atkins WM: A novel antioxidant role for ligandin behavior of glutathione S-transferases: attenuation of the photodynamic effects of hypericin. Biochemistry. 2004 Oct 12;43(40):12761-9. [PubMed:15461448]

Drug created on October 20, 2016 20:05 / Updated on November 02, 2018 07:33