Showing Compound Hypericin (FDB012603)

Record Information

Version

1.0

Creation date

2010-04-08 22:10:15 UTC

Update date

2019-11-26 03:07:10 UTC

Primary ID

FDB012603

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Hypericin

Description

Widespread in Hypericum subspecies especies Hypericum perforatum (St John's Wort) Hypericin is a red-coloured anthraquinone-derivative, which, together with hyperforin, is one of the principal active constituents of Hypericum (Saint John's wort). Hypericin is believed to act as an antibiotic and non-specific kinase inhibitor. Hypericin may inhibit the action of the enzyme dopamine ?-hydroxylase, leading to increased dopamine levels, although thus possibly decreasing norepinephrine and epinephrine. Hypericin is found in tea, alcoholic beverages, and herbs and spices.

CAS Number

548-04-9

Structure

MOL SDF PDB SMILES InChI

Synonyms

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Synonym	Source
1,3,4,6,8,13-Hexahydroxy-10,11-dimethylphenanthro[1,10,9,8-opqra]perylene-7,14-dione, 9ci	HMDB
1,3,4,6,8,13-Hexahydroxy-10,11-dimethylphenanthro[1,10,9,8-opqra]perylene-7,14-dione, 9CI	db_source
1:6:8:10:11:13-Hexahydroxy-3:4-dimethyl-meso-naphthodianthrene-7:14-dione	ChEBI
4,5,7,4',5',7'-Hexahydroxy-2,2'-dimethylnaphthodianthrone	HMDB
Hipericina	ChEBI
Hypericin & visible light	HMDB
Hypericin from hypericum perforatum	HMDB
Hypericine	ChEBI
Hypericum extract	HMDB
Hypericum red	ChEBI

Showing 1 to 10 of 14 entries

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

Chemical Formula

C30H16O8

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

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

Isomeric 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

Average Molecular Weight

504.4432

Monoisotopic Molecular Weight

504.084517488

Classification

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 )

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Biological location:

Subcellular:

Source:

Food

Biological:

Plant

Role

Industrial application:

Pharmaceutical industry:

Biological role:

Nutrient

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

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Property	Value	Reference
Boiling Point	Not Available
Charge	Not Available
Density	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Experimental Water Solubility	Not Available
Isoelectric point	Not Available
Mass Composition	C 71.43%; H 3.20%; O 25.37%	DFC
Melting Point	Mp 300° (dec.)	DFC
Optical Rotation	Not Available

Showing 1 to 10 of 14 entries

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	Hypericin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0udr-0000940000-0d62f6b32901e364142a	Spectrum
Predicted GC-MS	Hypericin, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-008a-5000049000-92bc0a911d1b58cfc8c0	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - , negative	splash10-0udi-0000090000-e9cd20b64eba34b7fb1e	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - , positive	splash10-0a4i-0000590000-d6f4544a5f160b2a5b67	2017-09-14	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-0000290000-6394299b12d4be2370c0	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-0000690000-a414125d88c1d0a72c3d	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-014i-0000900000-cf0d93c0ba6c563a5028	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-0000090000-19beb2301902b7490149	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0udi-0000190000-3347517bb50ff44b3105	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0f7c-1000910000-47bd0419d45b315930b3	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-0000090000-68abf5044d528fcc461f	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0udi-0000090000-68abf5044d528fcc461f	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0fb9-0000920000-c9ae44cdfd493073d84d	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-0000090000-2f988b9a0dc0ff33b3b6	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-0000090000-2f988b9a0dc0ff33b3b6	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-004i-0000920000-5ee63630602ca79b7329	2021-09-22	View Spectrum