ContaminantDB: Zeranol

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (10)XML

Record Information

Version

1.0

Creation Date

2010-04-15 18:58:24 UTC

Update Date

2026-05-14 19:10:00 UTC

Accession Number

CHEM002644

Identification

Common Name

Zeranol

Class

Small Molecule

Description

Zeranol is isolated from Fusarium species. It is an anabolic agent and estrogenic agent (mainly veterinary use). Zeranol is used as a growth promoter for food animals. It was banned by the EU in 1989, but is still permitted in the USA and some other countries. It may also arise in livestock by ingestion of Fusarium contaminated pasture or feeds. Zeranol has been shown to exhibit muscle building function (6). Zeranol belongs to the family of Macrolides and Analogues. These are organic compounds containing a lactone ring of at least twelve members[1]. The term 'macrolide' encompasses a diverse family of unrelated compounds with large macrolactam rings[2].

Contaminant Sources

FooDB Chemicals
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
6-(6,10-Dihydroxyundecyl)-beta-resorcylic acid, mu-lactone	HMDB
a-Zearalanol	HMDB
alpha Zearalanol	HMDB
alpha-Zearalanol	HMDB
alpha-Zeranol	HMDB
Dihydroxyundecyl resorcylic acid lactone	HMDB
Frideron	HMDB
MK 188	HMDB
p 1496	HMDB
Ralabol	HMDB
Ralgro	HMDB
Ralone	HMDB
Taleranol	HMDB
Xeranol	HMDB
Zearalanol	HMDB
Zearanol	HMDB
Zerano	HMDB
Zeranol, ban, inn, usan	HMDB
Zeranol	MeSH

Chemical Formula

C₁₈H₂₆O₅

Average Molecular Mass

322.396 g/mol

Monoisotopic Mass

322.178 g/mol

CAS Registry Number

26538-44-3

IUPAC Name

(3S,7R)-7,14,16-trihydroxy-3-methyl-3,4,5,6,7,8,9,10,11,12-decahydro-1H-2-benzoxacyclotetradecin-1-one

Traditional Name

7,14,16-trihydroxy-3-methyl-3,4,5,6,7,8,9,10,11,12-decahydro-2-benzoxacyclotetradecin-1-one

SMILES

CC1CCCC(O)CCCCCC2=CC(O)=CC(O)=C2C(=O)O1

InChI Identifier

InChI=1S/C18H26O5/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/h10-12,14,19-21H,2-9H2,1H3

InChI Key

DWTTZBARDOXEAM-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as macrolides and analogues. These are organic compounds containing a lactone ring of at least twelve members.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Macrolides and analogues

Sub Class

Not Available

Direct Parent

Macrolides and analogues

Alternative Parents

Substituents

Macrolide
Dihydroxybenzoic acid
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Benzenoid
Vinylogous acid
Carboxylic acid ester
Lactone
Secondary alcohol
Carboxylic acid derivative
Polyol
Monocarboxylic acid or derivatives
Oxacycle
Organoheterocyclic compound
Organooxygen compound
Organic oxide
Organic oxygen compound
Alcohol
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

Not Available

Chemical Roles

Not Available

Physical Properties

State

Solid

Appearance

White powder.

Experimental Properties

Property	Value
Melting Point	182 - 184°C
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.16 g/L	ALOGPS
logP	3.23	ALOGPS
logP	4.45	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Acidic)	8.68	ChemAxon
pKa (Strongest Basic)	-1.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	86.99 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	88.25 m³·mol⁻¹	ChemAxon
Polarizability	35.52 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	splash10-0pi0-0039000000-13fad28bcc84596403c8	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positive	splash10-00xr-9400750000-880938071e9cf0d46601	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_2) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_3) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_3_1) - 70eV, Positive	Not Available	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0ab9-0119000000-dfc5ec37377b5cb44b1f	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-06di-9467000000-8c76013cb1dc4d675963	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0cdv-9810000000-436eeea064627406d1c2	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00di-0009000000-c6fef88c1fc77cd2daeb	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0fk9-1119000000-ba401efa49d57ecccd16	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-054k-2390000000-42d3932aa047c309abda	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00di-0009000000-97dc86be510de646590c	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0udi-0009000000-2cd138540b8019f5060d	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0gbl-7098000000-932554e8d65256b31a67	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-0009000000-b59a570e604dc41d65bf	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-0009000000-43ce6ed6cc07dfd96e01	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-0093000000-db5e6ea92c271bf7050f	Spectrum

Toxicity Profile

Route of Exposure

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

Mechanism of Toxicity

Zeranol acts as an agonist at the estrogen receptors, interfering with the binding of natural estrogens. This disrupts hormone levels and affects a number of signaling processes, leading to various reproductive disorders in males and females. 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. (2, 1, 4)

Metabolism

Metabolism of zeranol occurs in the liver. During phase I metabolism, dehydrogenation produces zearalanone as the major metabolite and beta-zearalanol as the minor metabolite. Cytochrome P450 enzymes also catalyze the aromatic hydroxylation of zeranol, producing 13-hydroxy-alpha-zearalanol and 15-hydroxy-alpha-zearalanol. During phase II metabolism reduction/oxidation occurs, forming the glucuronide and sulfate conjugates of zearalanone and beta-zearalanol. In humans, the metabolites are excreted mainly in the urine. (3)

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

Not listed by IARC.

Uses/Sources

Zeranol is a mycotoxin derived from fungi in the Fusarium family, and may be found as a contaminant in fungus-infected crops. (7)

Minimum Risk Level

Estimated acceptable daily intake is 0 - 0.5 ug/kg. (8)

Health Effects

Zeranol is an estrogen-like endocrine disrupting chemical that interferes with the binding of natural estrogens, disrupting hormone levels and causing various reproductive disorders in males and females. It has been shown to cause developmental problems in animals by causing tissue malformations and produce irregularities in the estrous cycle. In humans, zeranol induces breast cancer cell growth. (2)

Symptoms

Not Available

Treatment

Not Available

Concentrations

Not Available

External Links

DrugBank ID

Not Available

HMDB ID

HMDB0032702

FooDB ID