Showing Compound Wyerone acid (FDB002922)

Record Information

Version

1.0

Creation date

2010-04-08 22:05:35 UTC

Update date

2025-11-18 22:41:52 UTC

Primary ID

FDB002922

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Wyerone acid

Description

(2e,11z)-wyerone acid is a member of the class of compounds known as furanoid fatty acids. Furanoid fatty acids are fatty acids containing a 5-alkylfuran-2-alkanoic acid (2e,11z)-wyerone acid is practically insoluble (in water) and a moderately acidic compound (based on its pKa). (2e,11z)-wyerone acid can be found in pulses, which makes (2e,11z)-wyerone acid a potential biomarker for the consumption of this food product.

CAS Number

54954-14-2

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
(2Z)-3-{5-[(4Z)-hept-4-en-2-ynoyl]furan-2-yl}prop-2-enoate	HMDB
3-[5-(1-Oxo-4-hepten-2-ynyl)-2-furanyl]-2-propenoic acid, 9CI	db_source
4,7-Epoxy-8-oxo-2,4,6,11-tetradecatetraen-9-ynoic acid	db_source

Predicted Properties

Property	Value	Source
Water Solubility	0.026 g/L	ALOGPS
logP	2.94	ALOGPS
logP	2.89	ChemAxon
logS	-4	ALOGPS
pKa (Strongest Acidic)	2.2	ChemAxon
pKa (Strongest Basic)	-4.4	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	67.51 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	69.29 m³·mol⁻¹	ChemAxon
Polarizability	25.13 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C14H12O4

IUPAC name

(2Z)-3-{5-[(4Z)-hept-4-en-2-ynoyl]furan-2-yl}prop-2-enoic acid

InChI Identifier

InChI=1S/C14H12O4/c1-2-3-4-5-6-12(15)13-9-7-11(18-13)8-10-14(16)17/h3-4,7-10H,2H2,1H3,(H,16,17)/b4-3-,10-8-

InChI Key

ZLZFXXJOALTVDA-YHOGECKDSA-N

Isomeric SMILES

CC\C=C/C#CC(=O)C1=CC=C(O1)\C=C/C(O)=O

Average Molecular Weight

244.2427

Monoisotopic Molecular Weight

244.073558872

Classification

Description

Belongs to the class of organic compounds known as furanoid fatty acids. These are fatty acids containing a 5-alkylfuran-2-alkanoic acid.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acids and conjugates

Direct Parent

Furanoid fatty acids

Alternative Parents

Substituents

Furanoid fatty acid
Aryl ketone
Furan
Heteroaromatic compound
Alpha,beta-unsaturated ketone
Ketone
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Oxacycle
Organoheterocyclic compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Organic oxygen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Biological:

Animal

Plant:

Fabaceae

Biological location:

Biofluid and excreta:

Urine

Cell and elements:

Extracellular

Subcellular:

Process

Naturally occurring process:

Biological process:

Biochemical process:

Chemical reaction:

Lipid peroxidation

Biochemical pathway:

Lipid metabolism pathway

Cellular process:

Cell signaling

Role

Industrial application:

Biological role:

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Not Available
Physical Description	Not Available
Mass Composition	C 68.85%; H 4.95%; O 26.20%	DFC
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	Wyerone acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-014i-1930000000-80ffc6c9056df3985ac7	Spectrum
Predicted GC-MS	Wyerone acid, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0fni-9853000000-6f5bbf69288fd7a46605	Spectrum
Predicted GC-MS	Wyerone acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-002b-0290000000-1b5cae0b6292bd71f28d	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-005j-6920000000-039155bd484317125ea2	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0fvl-9300000000-6b5685d2b4e1fb59134b	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0006-1490000000-50d0b0d622b9fb04a810	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-002g-4940000000-d466f031b16c755b2d33	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0aou-9700000000-6c45af926edc6d70f843	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0002-1290000000-eb733c9467de404fa16b	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0kg9-4940000000-598b00dc886e8b1d7180	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-002b-9300000000-3eef0f66a177eb69bebb	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0006-0390000000-bff68b9440cdda8d7f97	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0007-9610000000-2dc0276f14dd2b32f8f4	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9100000000-166a7ab7f3d1342b6499	2021-09-23	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

30776870

ChEMBL ID

Not Available

KEGG Compound ID

Not Available

Pubchem Compound ID

Not Available

Pubchem Substance ID

Not Available

ChEBI ID

Not Available

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

HMDB0030946

CRC / DFC (Dictionary of Food Compounds) ID

CPG29-N:CPG29-N

EAFUS ID

Not Available

Dr. Duke ID

WYERONE-ACID

BIGG ID

Not Available

KNApSAcK ID

C00001300

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
Fungicide	24127	An agent that kills or inhibits the growth of fungi, playing a biological role in preventing fungal infections. Therapeutically, it is used to treat fungal diseases, with key medical applications including athlete's foot, ringworm, and candidiasis, as well as agricultural uses to protect crops from fungal damage.	DUKE
Pesticide	25944	An agent that kills or repels pests, playing a biological role in controlling insect, weed, and fungal populations. Therapeutically, pesticides have limited applications, but some are used to treat ectoparasitic infestations, such as lice and scabies. Key medical uses include topical treatments for head lice and scabies, highlighting their role in managing parasitic infections.	DUKE
Phytoalexin	26115	A plant-derived compound that plays a biological role in defense against pathogens. It has therapeutic applications as an antimicrobial, antioxidant, and anti-inflammatory agent, with key medical uses in managing infections, cancer, and neurodegenerative diseases.	DUKE