ContaminantDB: Pyrohyperforin

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-05-26 01:23:57 UTC

Update Date

2016-11-09 01:18:56 UTC

Accession Number

CHEM029767

Identification

Common Name

Pyrohyperforin

Class

Small Molecule

Description

Constituent of Hypericum perforatum (St. John's Wort). Pyrohyperforin is found in tea, alcoholic beverages, and herbs and spices.

Contaminant Sources

FooDB Chemicals

Contaminant Type

Not Available

Chemical Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Not Available

Chemical Formula

C₃₅H₅₀O₄

Average Molecular Mass

534.769 g/mol

Monoisotopic Mass

534.371 g/mol

CAS Registry Number

303115-46-0

IUPAC Name

4,4,10-trimethyl-1,11-bis(3-methylbut-2-en-1-yl)-10-(4-methylpent-3-en-1-yl)-9-(2-methylpropanoyl)-3-oxatricyclo[7.3.1.0²,⁷]trideca-2(7),5-diene-8,13-dione

Traditional Name

4,4,10-trimethyl-1,11-bis(3-methylbut-2-en-1-yl)-10-(4-methylpent-3-en-1-yl)-9-(2-methylpropanoyl)-3-oxatricyclo[7.3.1.0²,⁷]trideca-2(7),5-diene-8,13-dione

SMILES

CC(C)C(=O)C12C(=O)C3=C(OC(C)(C)C=C3)C(CC=C(C)C)(CC(CC=C(C)C)C1(C)CCC=C(C)C)C2=O

InChI Identifier

InChI=1S/C35H50O4/c1-22(2)13-12-18-33(11)26(15-14-23(3)4)21-34(20-16-24(5)6)30-27(17-19-32(9,10)39-30)29(37)35(33,31(34)38)28(36)25(7)8/h13-14,16-17,19,25-26H,12,15,18,20-21H2,1-11H3

InChI Key

FSQFBVMRHUNWAT-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as monoterpenoids. Monoterpenoids are compounds containing a chain of two isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Monoterpenoids

Direct Parent

Monoterpenoids

Alternative Parents

Substituents

Monoterpenoid
Cyclohexenone
Pyran
Vinylogous ester
Ketone
Oxacycle
Organoheterocyclic compound
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Biological Properties

Status

Detected and Not Quantified

Origin

Not Available

Cellular Locations

Not Available

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

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	0.00041 g/L	ALOGPS
logP	6.7	ALOGPS
logP	9.03	ChemAxon
logS	-6.1	ALOGPS
pKa (Strongest Acidic)	19.09	ChemAxon
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	60.44 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	165.12 m³·mol⁻¹	ChemAxon
Polarizability	63.13 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	0	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-01bc-5001930000-3cda17cbedcd8a202346	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001i-0000290000-a8396cbb17858a571872	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-03di-2000930000-0caa26ca2d1c9964298c	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-02mj-3002910000-0132c0b637cb29ffb200	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001i-0000090000-188973541ae0d106fff4	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-001i-0000390000-56cc997382fd9330ba10	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-052e-6009800000-c32142fedb094d101855	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00ku-1000970000-62d1aa1b8ce6ab86882b	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-01di-3100910000-bdeb026128e65fcc3d1c	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0600-6000900000-6097ca6122c8589635c8	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-0002690000-5cce0d2c1cdb30070b06	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000j-7405970000-7f494c68ac5a4be87419	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9101100000-76b1fa17873e789b27ab	Spectrum

Toxicity Profile

Route of Exposure

Not Available

Mechanism of Toxicity

Not Available

Metabolism

Not Available

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

Not Available

Uses/Sources

Not Available

Minimum Risk Level

Not Available

Health Effects

Not Available

Symptoms

Not Available

Treatment

Not Available

Concentrations

Not Available

External Links

DrugBank ID

Not Available

HMDB ID

HMDB0035899

FooDB ID

FDB014684

Phenol Explorer ID

Not Available

KNApSAcK ID

Not Available

BiGG ID

Not Available

BioCyc ID

Not Available

METLIN ID

Not Available

PDB ID

Not Available

Wikipedia Link

Not Available

Chemspider ID

Not Available

ChEBI ID

Not Available

PubChem Compound ID

73808497

Kegg Compound ID

Not Available

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Not Available

MSDS

Not Available

General References

1. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9.

2. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10.

3. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20.

4. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621.

5. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.

6. The lipid handbook with CD-ROM

Pyrohyperforin (CHEM029767)

Structure for CHEM029767: Pyrohyperforin