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Record Information
Version2.0
Created at2022-09-10 00:40:42 UTC
Updated at2022-09-10 00:40:42 UTC
NP-MRD IDNP0292921
Secondary Accession NumbersNone
Natural Product Identification
Common Namezenone
DescriptionCis-Zearalenone belongs to the class of organic compounds known as zearalenones. These are macrolides which contains a fourteen-member lactone fused to 1,3-dihydroxybenzene. zenone is found in Fusarium culmorum. zenone was first documented in 2012 (PMID: 23157684). Based on a literature review a small amount of articles have been published on cis-Zearalenone (PMID: 26335359) (PMID: 25254638) (PMID: 22412694).
Structure
Thumb
SynonymsNot Available
Chemical FormulaC18H22O5
Average Mass318.3690 Da
Monoisotopic Mass318.14672 Da
IUPAC Name(3S)-14,16-dihydroxy-3-methyl-3,4,5,6,7,8,9,10-octahydro-1H-2-benzoxacyclotetradecine-1,7-dione
Traditional Name(-)-zearalenone
CAS Registry NumberNot Available
SMILES
C[C@H]1CCCC(=O)CCC\C=C/C2=CC(O)=CC(O)=C2C(=O)O1
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-/t12-/m0/s1
InChI KeyMBMQEIFVQACCCH-MIBUCLJRSA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Fusarium culmorumLOTUS Database
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.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassMacrolides and analogues
Sub ClassZearalenones
Direct ParentZearalenones
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 FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP4.37ChemAxon
pKa (Strongest Acidic)8.54ChemAxon
pKa (Strongest Basic)-4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area83.83 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity88.34 m³·mol⁻¹ChemAxon
Polarizability33.43 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDC00053956
Chemspider ID20118120
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound12445020
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Drzymala SS, Binder J, Brodehl A, Penkert M, Rosowski M, Garbe LA, Koch M: Estrogenicity of novel phase I and phase II metabolites of zearalenone and cis-zearalenone. Toxicon. 2015 Oct;105:10-2. doi: 10.1016/j.toxicon.2015.08.027. Epub 2015 Sep 1. [PubMed:26335359 ]
  2. Drzymala SS, Herrmann AJ, Maul R, Pfeifer D, Garbe LA, Koch M: In vitro phase I metabolism of cis-zearalenone. Chem Res Toxicol. 2014 Nov 17;27(11):1972-8. doi: 10.1021/tx500312g. Epub 2014 Oct 15. [PubMed:25254638 ]
  3. Koppen R, Riedel J, Proske M, Drzymala S, Rasenko T, Durmaz V, Weber M, Koch M: Photochemical trans-/cis-isomerization and quantitation of zearalenone in edible oils. J Agric Food Chem. 2012 Nov 28;60(47):11733-40. doi: 10.1021/jf3037775. Epub 2012 Nov 19. [PubMed:23157684 ]
  4. Koppen R, Riedel J, Emmerling F, Koch M: (3S,11Z)-14,16-Dihy-droxy-3-methyl-3,4,5,6,9,10-hexa-hydro-1H-2-benz-oxacyclo-tetra-decine-1,7(8H)-dione (cis-zearalenone): a redetermination. Acta Crystallogr Sect E Struct Rep Online. 2012 Mar 1;68(Pt 3):o832. doi: 10.1107/S1600536812002735. Epub 2012 Feb 24. [PubMed:22412694 ]
  5. LOTUS database [Link]