Hypericin (CED0004410)

Record Information

Version

1.0

Creation Date

2016-05-26 00:23:11 UTC

Update Date

2026-05-14 19:28:43 UTC

Accession Number

CHEM028335

Identification

Common Name

Hypericin

Class

Small Molecule

Description

Hypericin is an organic compound with the chemical formula C30H16O8. Hypericin belongs to the benzopyrenes, a subclass of pyrenes within the organic compounds. With an average molecular weight of 504.44 g/mol, Hypericin is a heavy molecule. This compound is found in or released from 14 recorded sources across several sectors. Within Electrical & Electronic Equipment, it is associated with cell phones, capacitors, wires and cables, batteries, and printed circuit boards, among one other source. It is also found in textiles, leather & furnishings, specifically within carpets and rugs as well as synthetic textiles. In the food, food processing & cookware sector, it is linked to food packaging. Further sources include medical devices in the healthcare, pharmaceuticals & veterinary products sector, and lubricants used in both energy, oil & gas and industrial manufacturing & chemical processing, along with two additional sectors. Recorded exposure routes for the substance include inhalation, oral, and touch. Biologically, Hypericin acts on two recorded protein targets. It functions as an inhibitor of Glutathione S-transferase A1 (GSTA1) and Glutathione S-transferase P (GSTP1).

Contaminant Type

PFAS
Phytotoxin

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
1:6:8:10:11:13-Hexahydroxy-3:4-dimethyl-meso-naphthodianthrene-7:14-dione	ChEBI
Hipericina	ChEBI
Hypericine	ChEBI
Hypericum red	ChEBI
Hyperizin	ChEBI
1,3,4,6,8,13-Hexahydroxy-10,11-dimethylphenanthro[1,10,9,8-opqra]perylene-7,14-dione, 9ci	HMDB
4,5,7,4',5',7'-Hexahydroxy-2,2'-dimethylnaphthodianthrone	HMDB
Hypericin & visible light	HMDB
Hypericin from hypericum perforatum	HMDB
Hypericum extract	HMDB
Mycoporphyrin	HMDB
Vimrxyn	HMDB
mono-(123I)iodohypericin	MeSH

Chemical Formula

C₃₀H₁₆O₈

Average Molecular Mass

504.443 g/mol

Monoisotopic Mass

504.085 g/mol

CAS Registry Number

548-04-9

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

Traditional Name

hypericin

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

InChI Identifier

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

InChI Key

BTXNYTINYBABQR-UHFFFAOYSA-N

Chemical Taxonomy

Description

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

Super Class

Class

Sub Class

Direct Parent

Alternative Parents

Substituents

Benzo-a-pyrene
Benzo-e-pyrene
Phenanthro-perylenequinone
Perylenequinone
Chrysene
Triphenylene
Phenanthrol
Phenanthrene
Anthracene
1-naphthol
2-naphthol
1-hydroxy-2-unsubstituted benzenoid
Vinylogous acid
Polyol
Organic oxide
Organooxygen compound
Organic oxygen compound
Hydrocarbon derivative
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic compounds

External Descriptors

carbopolycyclic compound (CHEBI:5835 )
Anthracenes and phenanthrenes (C07606 )
Anthrone type (C07606 )
Anthracenes and phenanthrenes (LMPK13040001 )

Biological Properties

Status

Detected and Not Quantified

Origin

Not Available

Cellular Locations

Not Available

Biofluid Locations

Not Available

Tissue Locations

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Organoleptic Effects

Not Available

Physical Properties

State

Not Available

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.0073 g/L	ALOGPS
logP	3.92	ALOGPS
logP	7.7	ChemAxon
logS	-4.8	ALOGPS
pKa (Strongest Acidic)	1.39	ChemAxon
pKa (Strongest Basic)	16.11	ChemAxon
Physiological Charge	-4	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	155.52 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	139.31 m³·mol⁻¹	ChemAxon
Polarizability	50.96 Å³	ChemAxon
Number of Rings	8	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum	splash10-0udr-0000940000-0d62f6b32901e364142a	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	splash10-008a-5000049000-92bc0a911d1b58cfc8c0	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0udi-0000090000-e9cd20b64eba34b7fb1e	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0a4i-0000590000-d6f4544a5f160b2a5b67	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0a4i-0000290000-6394299b12d4be2370c0	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0a4i-0000690000-a414125d88c1d0a72c3d	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-014i-0000900000-cf0d93c0ba6c563a5028	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0udi-0000090000-19beb2301902b7490149	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0udi-0000190000-3347517bb50ff44b3105	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0f7c-1000910000-47bd0419d45b315930b3	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0udi-0000090000-68abf5044d528fcc461f	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0udi-0000090000-68abf5044d528fcc461f	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0fb9-0000920000-c9ae44cdfd493073d84d	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0a4i-0000090000-2f988b9a0dc0ff33b3b6	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0a4i-0000090000-2f988b9a0dc0ff33b3b6	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-004i-0000920000-5ee63630602ca79b7329	Not Available	View Spectrum

Toxicity Profile

Mechanism of Toxicity

Not Available

Carcinogenicity (IARC Classification)

Not Available

Minimum Risk Level

Not Available

Symptoms

Not Available

Treatment

Not Available

Toxicity Values

Toxicity Value	Unit	Value Range	Organism	Dose Descriptor	Route of Exposure	Predicted or Experimental	Reference
2077.0	Log mg/kg	[1200:3700]	Rat	LD50	oral	predicted	Not Available

Health Effects

Health Effect	Relationship	Direction	Reference

Exposure Sources

Source ID	Source	Sector	Reference
7	Pesticides	Agriculture & land management	Not Available
120	Wires and cables	Electrical & Electronic Equipment	Not Available
121	Printed circuit boards	Electrical & Electronic Equipment	Not Available
125	Batteries	Electrical & Electronic Equipment	Not Available
130	Semiconductors	Electrical & Electronic Equipment	Not Available
138	Lubricants	Energy, oil & gas	Not Available
147	Food packaging	Food, food processing & cookware	Not Available
174	Lubricants	Industrial manufacturing & chemical processing	Not Available
234	Medical devices	Healthcare, pharmaceuticals & veterinary products	Not Available
451	Carpets and Rugs	Textiles, leather & furnishings	Not Available
454	Synthetic textiles	Textiles, leather & furnishings	Not Available
490		Personal care & cosmetics	Not Available
492	Cell phones	Electrical & Electronic Equipment	Not Available
493	Capacitors	Electrical & Electronic Equipment	Not Available
503	Tents Or Canopies	Building & Construction	Not Available
678	Nitrogenous Fertilisers	Agriculture & land management	Not Available
679	Phosphatic Fertilisers	Agriculture & land management	Not Available
685	Ceramics	Building & Construction	Not Available

Pathways

0 pathways

No pathways found

No metabolic pathways have been associated with this synthetic chemical

Targets

Structure	Protein	UniProt ID	Organism	Relationship	Details
Click to view 3D structure	Glutathione reductase	P41921	Saccharomyces cerevisiae S288c	Predicted (SEA)	0.0778492
Click to view 3D structure	Thioredoxin reductase 2, mitochondrial	Q9Z0J5	Rattus norvegicus	Predicted (SEA)	0.0778492
Click to view 3D structure	Gag-Pol polyprotein	Q7ZJM1	Human immunodeficiency virus 1	Predicted (SEA)	10.5096
Click to view 3D structure	Cytochrome P450 3A4	P08684	Humans	Predicted (SEA)	223.661
Click to view 3D structure	Alpha-synuclein	P37840	Humans	Predicted (SEA)	2.80257
Click to view 3D structure	Cysteine protease ATG4B	Q9Y4P1	Humans	Predicted (SEA)	1.79053
Click to view 3D structure	Cystathionine beta-synthase	P35520	Humans	Predicted (SEA)	0.0778492
Click to view 3D structure	D(3) dopamine receptor	P35462	Humans	Predicted (SEA)	281.503
Click to view 3D structure	Serine/threonine-protein kinase pim-1	P11309	Humans	Predicted (SEA)	536.381
Click to view 3D structure	Aurora kinase B	Q96GD4	Humans	Predicted (SEA)	717.381
Click to view 3D structure	Corticotropin-releasing factor receptor 1	P34998	Humans	Predicted (SEA)	75.8251
Click to view 3D structure	Reverse transcriptase	Q06347	Human immunodeficiency virus 2	Predicted (SEA)	1.16774
Click to view 3D structure	Induced myeloid leukemia cell differentiation protein Mcl-1	Q07820	Humans	Predicted (SEA)	436.734
Click to view 3D structure	Sialidase	P10481	Clostridium perfringens	Predicted (SEA)	16.6597
Click to view 3D structure	Estrogen receptor beta	Q92731	Humans	Predicted (SEA)	288.276
Click to view 3D structure	Protein E6	P03126	Human papillomavirus type 16	Predicted (SEA)	6.22794
Click to view 3D structure	Tyrosine-protein kinase transforming protein Fps	P00530	Fujinami sarcoma virus	Predicted (SEA)	5.13805
Click to view 3D structure	Estrogen receptor	P03372	Humans	Predicted (SEA)	258.07
Click to view 3D structure	Protein deacetylase HDAC6	Q9UBN7	Humans	Predicted (SEA)	1596.14
Click to view 3D structure	17-beta-hydroxysteroid dehydrogenase type 2	P37059	Humans	Predicted (SEA)	61.1116
Click to view 3D structure	Amine oxidase [flavin-containing] A	P21397	Humans	Predicted (SEA)	508.589
Click to view 3D structure	Amyloid-beta precursor protein	P05067	Humans	Predicted (SEA)	245.848
Click to view 3D structure	Aldo-keto reductase family 1 member B1	P15121	Humans	Predicted (SEA)	153.519
Click to view 3D structure	17-beta-hydroxysteroid dehydrogenase type 1	P14061	Humans	Predicted (SEA)	49.3564
Click to view 3D structure	Cytochrome P450 1B1	Q16678	Humans	Predicted (SEA)	177.963