ContaminantDB: (S,E)-Zearalenone

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (14)XML

Record Information

Version

1.0

Creation Date

2009-12-22 23:09:04 UTC

Update Date

2016-11-09 01:08:54 UTC

Accession Number

CHEM002634

Identification

Common Name

(S,E)-Zearalenone

Class

Small Molecule

Description

cis-Zearalenone is a metabolite of Fusarium species.

Contaminant Sources

FooDB Chemicals
IARC Carcinogens Group 3
STOFF IDENT Compounds
T3DB toxins
ToxCast & Tox21 Chemicals

Contaminant Type

Ester
Ether
Food Toxin
Fungal Toxin
Metabolite
Mycotoxin
Natural Compound
Organic Compound

Chemical Structure

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

Synonyms

Value	Source
Zearalenone	HMDB

Chemical Formula

C₁₈H₂₂O₅

Average Molecular Mass

318.364 g/mol

Monoisotopic Mass

318.147 g/mol

CAS Registry Number

17924-92-4

IUPAC Name

14,16-dihydroxy-3-methyl-3,4,5,6,7,8,9,10-octahydro-1H-2-benzoxacyclotetradecine-1,7-dione

Traditional Name

zearalenone

SMILES

[H]\C1=C([H])/C2=CC(O)=CC(O)=C2C(=O)OC(C)CCCC(=O)CCC1

InChI Identifier

InChI=1S/C18H22O5/c1-12-6-5-9-14(19)8-4-2-3-7-13-10-15(20)11-16(21)17(13)18(22)23-12/h3,7,10-12,20-21H,2,4-6,8-9H2,1H3/b7-3+

InChI Key

MBMQEIFVQACCCH-XVNBXDOJSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as zearalenones. These are macrolides which contains a fourteen-member lactone fused to 1,3-dihydroxybenzene.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Macrolides and analogues

Sub Class

Zearalenones

Direct Parent

Zearalenones

Alternative Parents

Substituents

Zearalenone-skeleton
Dihydroxybenzoic acid
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Benzenoid
Vinylogous acid
Carboxylic acid ester
Ketone
Lactone
Cyclic ketone
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Oxacycle
Organoheterocyclic compound
Organic oxide
Organooxygen compound
Carbonyl group
Organic oxygen compound
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Membrane

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

Chemical Roles

Not Available

Physical Properties

State

Solid

Appearance

White crystalline solid.

Experimental Properties

Property	Value
Melting Point	164 - 165°C
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.12 g/L	ALOGPS
logP	3.04	ALOGPS
logP	4.37	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Acidic)	8.54	ChemAxon
pKa (Strongest Basic)	-4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	83.83 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	88.34 m³·mol⁻¹	ChemAxon
Polarizability	33.61 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0gb9-0079000000-cf44e7bb4ee64f0d3896	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive	splash10-0002-3309400000-ce2bcf4d245aeb4d31c6	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-01q0-0790000000-1fa65f0617c0400cecbd	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-0159-0595000000-386809f17d0b284e91cb	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-03ds-0930000000-ef0a9994f660c09205d6	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-014i-0049000000-df1eb225ba0f54468443	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-0159-0596000000-79fff53bb8f3c134d581	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-0159-0960000000-954fc7b9e1e052697b57	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014i-0119000000-48d711133498a6faf23f	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0gb9-6895000000-f3d9bc525746ba2954cf	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0kcs-9620000000-783b8e8c5d4ee960a711	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-0019000000-03d83983a9b52c36a2a3	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-014i-0249000000-ff5f3e61569739257ebd	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-014i-3290000000-c2a1bce9e404b58870ea	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-0009000000-d6724d5f96d12393720c	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-014i-0019000000-7a1a5135e5cb69209621	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-017m-3092000000-e206b0e721ac4d51ea06	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0udi-0009000000-fe790e008da0a36805e1	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0udi-0029000000-44386a824121853a7886	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-001j-0090000000-e59ee8f254acdf25aa99	Spectrum

Toxicity Profile

Route of Exposure

Oral, dermal, inhalation, and parenteral (contaminated drugs). (5)

Mechanism of Toxicity

Zearalenone's genotoxicity results from it's ability to cause DNA fragmentation, chromosome aberrations, and DNA adduct formation. It exerts cytotoxic effects by enhancing lipid peroxidation, increasing oxidative stress, and inducing apoptosis. Zearalenone also has significant estrogenic activity, causing severe reproductive problems in animals. In humans, Zearalenone has been shown to cause an earlier onset of puberty in children, endometrial adenocarcinomas, hyperplasia and breast cancer in women. Mycotoxins are often able to enter the liver and kidney by human organic anion transporters (hOATs) and human organic cation transporters (hOCTs). They can also inhibit uptake of anions and cations by these transporters, interefering with the secretion of endogenous metabolites, drugs, and xenobiotics including themselves. This results in increased cellular accumulation of toxic compounds causing nephro- and hepatotoxicity. (3, 4)

Metabolism

Zearalenone is rapidly absorbed after oral administration. In humans, most of the zearalenone absorbed is not metabolized. The main metabolites include alpha- and beta-zeralenol, and the glucuronide conjugates of both the parent compound and its metabolites. Zearalenone and its metabolites are excreted mainly in the bile. (1, 7)

Toxicity Values

LD50: >2000 mg/kg (Oral, Mouse) (7) LD50: >500 mg/kg (Intraperitoneal, Mouse) (7)

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

3, not classifiable as to its carcinogenicity to humans. (6)

Uses/Sources

Zearalenone (ZEA), also known as RAL and F-2 mycotoxin, is a potent estrogenic metabolite produced by some Giberella species. Several Fusarium species also produce zearalenone as their primary toxin. It can be found worldwide in a number of cereal crops, such as maize, barley, oats, wheat, rice, and sorghum, and also in bread. (8)

Minimum Risk Level

Not Available

Health Effects

Zearalenone is a reproductive toxin and has been shown to cause infertility, abortion or other breeding problems in livestock. In humans it can cause earlier onset of puberty in children, endometrial adenocarcinomas, hyperplasia, and breast cancer in women. Zearalenone is also immunotoxic, genotoxic, and can cause kidney and liver damage. (8, 3)

Symptoms

Not Available

Treatment

Not Available

Concentrations

Not Available

External Links

DrugBank ID

Not Available

HMDB ID

HMDB0031752

FooDB ID