Showing Compound Parthenolide (FDB005891)

Record Information

Version

1.0

Creation date

2010-04-08 22:06:53 UTC

Update date

2019-11-26 03:00:50 UTC

Primary ID

FDB005891

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Parthenolide

Description

Parthenolide belongs to germacranolides and derivatives class of compounds. Those are sesquiterpene lactones with a structure based on the germacranolide skeleton, characterized by a gamma lactone fused to a 1,7-dimethylcyclodec-1-ene moiety. Thus, parthenolide is considered to be an isoprenoid lipid molecule. Parthenolide is practically insoluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). Parthenolide is a bitter tasting compound found in sweet bay, which makes parthenolide a potential biomarker for the consumption of this food product. Parthenolide is a sesquiterpene lactone of the germacranolide class which occurs naturally in the plant feverfew (Tanacetum parthenium), after which it is named. It is found in highest concentration in the flowers and fruit .

CAS Number

20554-84-1

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
Parthenolide, (1ar-(1ar,4E,7as,10as,10br))-isomer	MeSH
(-)-parthenolide	biospider
Feverfew 125mg	biospider
Parthenolide	biospider

Predicted Properties

Property	Value	Source
Water Solubility	0.2 g/L	ALOGPS
logP	3.03	ALOGPS
logP	3.07	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Basic)	-4.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	38.83 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	68.55 m³·mol⁻¹	ChemAxon
Polarizability	26.8 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C15H20O3

IUPAC name

(1S,2S,4R,7E,11S)-4,8-dimethyl-12-methylidene-3,14-dioxatricyclo[9.3.0.0²,⁴]tetradec-7-en-13-one

InChI Identifier

InChI=1S/C15H20O3/c1-9-5-4-8-15(3)13(18-15)12-11(7-6-9)10(2)14(16)17-12/h5,11-13H,2,4,6-8H2,1,3H3/b9-5+/t11-,12-,13-,15+/m0/s1

InChI Key

KTEXNACQROZXEV-SLXBATTESA-N

Isomeric SMILES

C\C1=C/CC[C@@]2(C)O[C@H]2[C@H]2OC(=O)C(=C)[C@@H]2CC1

Average Molecular Weight

248.3175

Monoisotopic Molecular Weight

248.141244506

Classification

Description

Belongs to the class of organic compounds known as germacranolides and derivatives. These are sesquiterpene lactones with a structure based on the germacranolide skeleton, characterized by a gamma lactone fused to a 1,7-dimethylcyclodec-1-ene moiety.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Germacranolides and derivatives

Alternative Parents

Substituents

Germacranolide
Germacrane sesquiterpenoid
Sesquiterpenoid
Gamma butyrolactone
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Tetrahydrofuran
Carboxylic acid ester
Lactone
Carboxylic acid derivative
Dialkyl ether
Oxirane
Ether
Oxacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Organic oxide
Hydrocarbon derivative
Carbonyl group
Organic oxygen compound
Organooxygen compound
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Germacrane sesquiterpenoids (C07609 )
Germacrenes (C07609 )
Germacrane sesquiterpenoids (LMPR0103090002 )

Ontology

No ontology term

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Not Available
Physical Description	Not Available
Mass Composition	Not Available
Melting Point	Not Available
Boiling Point	Not Available
Experimental Water Solubility	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	Not Available
Spectroscopic UV Data	Not Available
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	Parthenolide, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-004i-6960000000-5c1aa0cf39755985bca4	Spectrum

MS/MS

Type	Description	Splash Key	View
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0002-0190000000-2684c1a3def8a4a69519	2017-07-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-002b-3790000000-8a7aea26cf89a7dd3c20	2017-07-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0uxu-9200000000-455b7641ab6a4f2dd513	2017-07-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0002-0090000000-e731516f7092e30f24f4	2017-07-26	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0f6t-0190000000-ad0cc1643ecd2864122e	2017-07-26	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0zi1-9610000000-42285f97b7fa82676424	2017-07-26	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

Not Available

ChEMBL ID

Not Available

KEGG Compound ID

C07609

Pubchem Compound ID

6473881

Pubchem Substance ID

Not Available

ChEBI ID

Not Available

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

Not Available

CRC / DFC (Dictionary of Food Compounds) ID

Not Available

EAFUS ID

Not Available

Dr. Duke ID

PARTHENOLIDE

BIGG ID

Not Available

KNApSAcK ID

C00003345

HET ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

Not Available

SuperScent ID

Not Available

Wikipedia ID

Not Available

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

Food	Content Range	Average	Reference
Food			Reference

Biological Effects and Interactions

Health Effects / Bioactivities

Descriptor	ID	Definition	Reference
5-hydroxytryptamine inhibitor	48279	Drugs that bind to but do not activate serotonin receptors, thereby blocking the actions of serotonin or serotonergic agonists.	DUKE
5-lipoxygenase inhibitor	23924	A compound or agent that combines with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction.	DUKE
allelopathic			DUKE
allergenic	50904	A chemical compound which causes the onset of an allergic reaction by interacting with any of the molecular pathways involved in an allergy.	DUKE
anti aggregant			DUKE
anti arthritic	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
anti bacterial	33282	A substance that kills or slows the growth of bacteria.	DUKE
anti cancer	35610	A substance that inhibits or prevents the proliferation of neoplasms.	DUKE
anti inflammatory	35472	A substance that reduces or suppresses inflammation.	DUKE
anti migraine	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
anti neuralgic	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
anti prostaglandin	49020	A chemical substance which inhibits the function of the endocrine glands, the biosynthesis of their secreted hormones, or the action of hormones upon their specific sites.	DUKE
anti secretory			DUKE
anti septic	33281	A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.	DUKE
anti spasmodic	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
antitumor	35610	A substance that inhibits or prevents the proliferation of neoplasms.	DUKE
candidicide			DUKE
cyclooxygenase-2 inhibitor	50629	A cyclooxygenase inhibitor that interferes with the action of cyclooxygenase 2.	DUKE
cyclooxygenase inhibitor	35544	A compound or agent that combines with cyclooxygenases (EC 1.14.99.1) and thereby prevents its substrate-enzyme combination with arachidonic acid and the formation of icosanoids, prostaglandins, and thromboxanes.	DUKE
cytotoxic	52209	A role played by the molecular entity or part thereof which causes the development of a pathological process.	DUKE
dermatitigenic			DUKE
fungicide	24127	A substance used to destroy fungal pests.	DUKE
Gram(+)icide	33282	A substance that kills or slows the growth of bacteria.	DUKE
hypercalcuric			DUKE
pesticide	25944	Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.	DUKE
phospholipase inhibitor	23924	A compound or agent that combines with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction.	DUKE
prostaglandin-synthetase inhibitor	23924	A compound or agent that combines with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction.	DUKE

Enzymes

Not Available

Pathways

Not Available

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

Flavor	Citations
bitter	Ayana Wiener, Marina Shudler, Anat Levit, Masha Y. Niv. BitterDB: a database of bitter compounds. Nucleic Acids Res 2012, 40(Database issue):D413-419. DOI:10.1093/nar/gkr755

Files

MSDS

Not Available

References

Synthesis Reference

Not Available

General Reference

Not Available

Content Reference

— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).