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
Not Available
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
Structured Indications
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
DrugInteractionDrug group
AcetyldigitoxinAcetyldigitoxin may decrease the cardiotoxic activities of Hypericin.Approved
AcetyldigoxinAcetyldigoxin may decrease the cardiotoxic activities of Hypericin.Experimental
BCG vaccineThe therapeutic efficacy of BCG vaccine can be decreased when used in combination with Hypericin.Investigational
BevacizumabBevacizumab may increase the cardiotoxic activities of Hypericin.Approved, Investigational
CabazitaxelThe risk or severity of adverse effects can be increased when Cabazitaxel is combined with Hypericin.Approved
Clostridium tetani toxoid antigen (formaldehyde inactivated)The therapeutic efficacy of Clostridium tetani toxoid antigen (formaldehyde inactivated) can be decreased when used in combination with Hypericin.Approved
Corynebacterium diphtheriae toxoid antigen (formaldehyde inactivated)The therapeutic efficacy of Corynebacterium diphtheriae toxoid antigen (formaldehyde inactivated) can be decreased when used in combination with Hypericin.Approved
CyclophosphamideCyclophosphamide may increase the cardiotoxic activities of Hypericin.Approved, Investigational
CymarinCymarin may decrease the cardiotoxic activities of Hypericin.Experimental
DenosumabThe risk or severity of adverse effects can be increased when Denosumab is combined with Hypericin.Approved
DeslanosideDeslanoside may decrease the cardiotoxic activities of Hypericin.Approved
DigitoxinDigitoxin may decrease the cardiotoxic activities of Hypericin.Approved, Investigational
DigoxinDigoxin may decrease the cardiotoxic activities of Hypericin.Approved
Digoxin Immune Fab (Ovine)Digoxin Immune Fab (Ovine) may decrease the cardiotoxic activities of Hypericin.Approved
DocetaxelThe risk or severity of adverse effects can be increased when Docetaxel is combined with Hypericin.Approved, Investigational
FingolimodHypericin may increase the immunosuppressive activities of Fingolimod.Approved, Investigational
G17DTThe therapeutic efficacy of G17DT can be decreased when used in combination with Hypericin.Investigational
GI-5005The therapeutic efficacy of GI-5005 can be decreased when used in combination with Hypericin.Investigational
GitoformateGitoformate may decrease the cardiotoxic activities of Hypericin.Experimental
Hepatitis A VaccineThe therapeutic efficacy of Hepatitis A Vaccine can be decreased when used in combination with Hypericin.Approved
Hepatitis B Vaccine (Recombinant)The therapeutic efficacy of Hepatitis B Vaccine (Recombinant) can be decreased when used in combination with Hypericin.Approved, Withdrawn
INGN 201The therapeutic efficacy of INGN 201 can be decreased when used in combination with Hypericin.Investigational
INGN 225The therapeutic efficacy of INGN 225 can be decreased when used in combination with Hypericin.Investigational
Lanatoside CLanatoside C may decrease the cardiotoxic activities of Hypericin.Experimental
LeflunomideThe risk or severity of adverse effects can be increased when Hypericin is combined with Leflunomide.Approved, Investigational
MetildigoxinMetildigoxin may decrease the cardiotoxic activities of Hypericin.Experimental
NatalizumabThe risk or severity of adverse effects can be increased when Hypericin is combined with Natalizumab.Approved, Investigational
OleandrinOleandrin may decrease the cardiotoxic activities of Hypericin.Experimental, Investigational
OuabainOuabain may decrease the cardiotoxic activities of Hypericin.Approved
PaclitaxelThe risk or severity of adverse effects can be increased when Paclitaxel is combined with Hypericin.Approved, Vet Approved
PeruvosidePeruvoside may decrease the cardiotoxic activities of Hypericin.Experimental
PimecrolimusThe risk or severity of adverse effects can be increased when Pimecrolimus is combined with Hypericin.Approved, Investigational
ProscillaridinProscillaridin may decrease the cardiotoxic activities of Hypericin.Experimental
Rabies virus inactivated antigen, AThe risk or severity of adverse effects can be increased when Hypericin is combined with Rabies virus inactivated antigen, A.Approved
Rabies virus inactivated antigen, AThe therapeutic efficacy of Rabies virus inactivated antigen, A can be decreased when used in combination with Hypericin.Approved
RindopepimutThe therapeutic efficacy of Rindopepimut can be decreased when used in combination with Hypericin.Investigational
RoflumilastRoflumilast may increase the immunosuppressive activities of Hypericin.Approved
Rotavirus VaccineThe therapeutic efficacy of Rotavirus Vaccine can be decreased when used in combination with Hypericin.Approved
Rubella virus vaccineThe therapeutic efficacy of Rubella virus vaccine can be decreased when used in combination with Hypericin.Approved
Salmonella typhi ty21a live antigenThe therapeutic efficacy of Salmonella typhi ty21a live antigen can be decreased when used in combination with Hypericin.Approved
Sipuleucel-TThe therapeutic efficacy of Sipuleucel-T can be decreased when used in combination with Hypericin.Approved
SRP 299The therapeutic efficacy of SRP 299 can be decreased when used in combination with Hypericin.Investigational
TacrolimusThe risk or severity of adverse effects can be increased when Tacrolimus is combined with Hypericin.Approved, Investigational
TecemotideThe therapeutic efficacy of Tecemotide can be decreased when used in combination with Hypericin.Investigational
TG4010The therapeutic efficacy of TG4010 can be decreased when used in combination with Hypericin.Investigational
TofacitinibHypericin may increase the immunosuppressive activities of Tofacitinib.Approved, Investigational
TrastuzumabTrastuzumab may increase the cardiotoxic activities of Hypericin.Approved, Investigational
Yellow fever vaccineThe therapeutic efficacy of Yellow fever vaccine can be decreased when used in combination with Hypericin.Approved
Zoster vaccineThe therapeutic efficacy of Zoster vaccine can be decreased when used in combination with Hypericin.Approved
Food Interactions
Not Available

References

General References
Not Available
External Links
Human Metabolome Database
HMDB34271
KEGG Compound
C07606
PubChem Compound
5281051
PubChem Substance
347829150
ChemSpider
4444511
BindingDB
50060874
ChEBI
5835
ChEMBL
CHEMBL286494

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 09, 2017 05:16