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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:51:17 UTC
Update Date2019-07-23 06:11:35 UTC
HMDB IDHMDB0032702
Secondary Accession Numbers
  • HMDB32702
Metabolite Identification
Common NameZeranol
DescriptionZeranol, also known as a-zearalanol or alpha-zeranol, 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. Zeranol is used as a growth promoter for food animals. Zeranol is an extremely weak basic (essentially neutral) compound (based on its pKa). Zeranol is a potentially toxic compound. They can also inhibit uptake of anions and cations by these transporters, interefering with the secretion of endogenous metabolites, drugs, and xenobiotics including themselves. It was banned by the EU in 1989, but is still permitted in the USA and some other countries. Zeranol is isolated from Fusarium species.
Structure
Data?1563862295
Synonyms
ValueSource
6-(6,10-Dihydroxyundecyl)-beta-resorcylic acid, mu-lactoneHMDB
a-ZearalanolHMDB
alpha ZearalanolHMDB
alpha-ZearalanolHMDB
alpha-ZeranolHMDB
Dihydroxyundecyl resorcylic acid lactoneHMDB
FrideronHMDB
MK 188HMDB
p 1496HMDB
RalabolHMDB
RalgroHMDB
RaloneHMDB
TaleranolHMDB
XeranolHMDB
ZearalanolHMDB
ZearanolHMDB
ZeranoHMDB
Zeranol, ban, inn, usanHMDB
ZeranolMeSH
Chemical FormulaC18H26O5
Average Molecular Weight322.396
Monoisotopic Molecular Weight322.178023942
IUPAC Name7,14,16-trihydroxy-3-methyl-3,4,5,6,7,8,9,10,11,12-decahydro-1H-2-benzoxacyclotetradecin-1-one
Traditional Name7,14,16-trihydroxy-3-methyl-3,4,5,6,7,8,9,10,11,12-decahydro-2-benzoxacyclotetradecin-1-one
CAS Registry Number26538-44-3
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 KeyDWTTZBARDOXEAM-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.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassMacrolides and analogues
Sub ClassNot Available
Direct ParentMacrolides 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 FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Biological location:

Source:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point182 - 184 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.16 g/LALOGPS
logP3.23ALOGPS
logP4.45ChemAxon
logS-3.3ALOGPS
pKa (Strongest Acidic)8.68ChemAxon
pKa (Strongest Basic)-1.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area86.99 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity88.25 m³·mol⁻¹ChemAxon
Polarizability35.52 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0pi0-0039000000-13fad28bcc84596403c8Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-00xr-9400750000-880938071e9cf0d46601Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0ab9-0119000000-dfc5ec37377b5cb44b1fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-06di-9467000000-8c76013cb1dc4d675963Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0cdv-9810000000-436eeea064627406d1c2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0009000000-c6fef88c1fc77cd2daebSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0fk9-1119000000-ba401efa49d57ecccd16Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-054k-2390000000-42d3932aa047c309abdaSpectrum
Biological Properties
Cellular Locations
  • Membrane
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB010663
KNApSAcK IDNot Available
Chemspider ID20916
KEGG Compound IDC14752
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkZeranol
METLIN IDNot Available
PubChem Compound22283
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Roeder RA, Gunn JM: Effects of zeranol on protein turnover in L6 myotubes. Domest Anim Endocrinol. 1987 Jan;4(1):61-7. [PubMed:3333934 ]
  2. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Enzymes

General function:
Involved in sulfotransferase activity
Specific function:
Sulfotransferase that utilizes 3'-phospho-5'-adenylyl sulfate (PAPS) as sulfonate donor to catalyze the sulfate conjugation of many hormones, neurotransmitters, drugs and xenobiotic compounds. Sulfonation increases the water solubility of most compounds, and therefore their renal excretion, but it can also result in bioactivation to form active metabolites. Sulfates hydroxysteroids like DHEA. Isoform 1 preferentially sulfonates cholesterol, and isoform 2 avidly sulfonates pregnenolone but not cholesterol.
Gene Name:
SULT2B1
Uniprot ID:
O00204
Molecular weight:
39598.595
Reactions
Zeranol → (14,16-dihydroxy-3-methyl-1-oxo-3,4,5,6,7,8,9,10,11,12-decahydro-1H-2-benzoxacyclotetradecin-7-yl)oxidanesulfonic aciddetails
General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone.
Gene Name:
UGT1A1
Uniprot ID:
P22309
Molecular weight:
59590.91
Reactions
Zeranol → 6-[(7,14-dihydroxy-3-methyl-1-oxo-3,4,5,6,7,8,9,10,11,12-decahydro-1H-2-benzoxacyclotetradecin-16-yl)oxy]-3,4,5-trihydroxyoxane-2-carboxylic aciddetails
Zeranol → 6-[(7,16-dihydroxy-3-methyl-1-oxo-3,4,5,6,7,8,9,10,11,12-decahydro-1H-2-benzoxacyclotetradecin-14-yl)oxy]-3,4,5-trihydroxyoxane-2-carboxylic aciddetails