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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2021-09-11 19:57:57 UTC
Update Date2021-09-26 23:15:18 UTC
HMDB IDHMDB0258416
Secondary Accession NumbersNone
Metabolite Identification
Common Name(11S)-11-Methyl-15,17-bis(oxidanyl)-12-oxabicyclo[12.4.0]octadeca-1(18),2,14,16-tetraene-7,13-dione
Description14,16-dihydroxy-3-methyl-3,4,5,6,7,8,9,10-octahydro-1H-2-benzoxacyclotetradecine-1,7-dione belongs to the class of organic compounds known as zearalenones. These are macrolides which contains a fourteen-member lactone fused to 1,3-dihydroxybenzene. Based on a literature review a small amount of articles have been published on 14,16-dihydroxy-3-methyl-3,4,5,6,7,8,9,10-octahydro-1H-2-benzoxacyclotetradecine-1,7-dione. This compound has been identified in human blood as reported by (PMID: 31557052 ). (11s)-11-methyl-15,17-bis(oxidanyl)-12-oxabicyclo[12.4.0]octadeca-1(18),2,14,16-tetraene-7,13-dione is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically (11S)-11-Methyl-15,17-bis(oxidanyl)-12-oxabicyclo[12.4.0]octadeca-1(18),2,14,16-tetraene-7,13-dione is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.
Structure
Thumb
SynonymsNot Available
Chemical FormulaC18H22O5
Average Molecular Weight318.369
Monoisotopic Molecular Weight318.146723808
IUPAC Name14,16-dihydroxy-3-methyl-3,4,5,6,7,8,9,10-octahydro-1H-2-benzoxacyclotetradecine-1,7-dione
Traditional Namezearalenone
CAS Registry NumberNot Available
SMILES
CC1CCCC(=O)CCCC=CC2=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
InChI KeyMBMQEIFVQACCCH-UHFFFAOYSA-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.
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
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
logP3.04ALOGPS
logP4.37ChemAxon
logS-3.4ALOGPS
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
Polarizability33.36 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+174.62530932474
DeepCCS[M-H]-172.26730932474
DeepCCS[M-2H]-205.18530932474
DeepCCS[M+Na]+181.38330932474
AllCCS[M+H]+177.232859911
AllCCS[M+H-H2O]+173.832859911
AllCCS[M+NH4]+180.332859911
AllCCS[M+Na]+181.232859911
AllCCS[M-H]-179.532859911
AllCCS[M+Na-2H]-179.732859911
AllCCS[M+HCOO]-180.132859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
(11S)-11-Methyl-15,17-bis(oxidanyl)-12-oxabicyclo[12.4.0]octadeca-1(18),2,14,16-tetraene-7,13-dioneCC1CCCC(=O)CCCC=CC2=CC(O)=CC(O)=C2C(=O)O13681.2Standard polar33892256
(11S)-11-Methyl-15,17-bis(oxidanyl)-12-oxabicyclo[12.4.0]octadeca-1(18),2,14,16-tetraene-7,13-dioneCC1CCCC(=O)CCCC=CC2=CC(O)=CC(O)=C2C(=O)O12754.6Standard non polar33892256
(11S)-11-Methyl-15,17-bis(oxidanyl)-12-oxabicyclo[12.4.0]octadeca-1(18),2,14,16-tetraene-7,13-dioneCC1CCCC(=O)CCCC=CC2=CC(O)=CC(O)=C2C(=O)O12815.8Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
(11S)-11-Methyl-15,17-bis(oxidanyl)-12-oxabicyclo[12.4.0]octadeca-1(18),2,14,16-tetraene-7,13-dione,3TMS,isomer #1CC1CCCC(O[Si](C)(C)C)=CCCC=CC2=CC(O[Si](C)(C)C)=CC(O[Si](C)(C)C)=C2C(=O)O12894.1Semi standard non polar33892256
(11S)-11-Methyl-15,17-bis(oxidanyl)-12-oxabicyclo[12.4.0]octadeca-1(18),2,14,16-tetraene-7,13-dione,3TMS,isomer #1CC1CCCC(O[Si](C)(C)C)=CCCC=CC2=CC(O[Si](C)(C)C)=CC(O[Si](C)(C)C)=C2C(=O)O12797.4Standard non polar33892256
(11S)-11-Methyl-15,17-bis(oxidanyl)-12-oxabicyclo[12.4.0]octadeca-1(18),2,14,16-tetraene-7,13-dione,3TMS,isomer #1CC1CCCC(O[Si](C)(C)C)=CCCC=CC2=CC(O[Si](C)(C)C)=CC(O[Si](C)(C)C)=C2C(=O)O13541.5Standard polar33892256
(11S)-11-Methyl-15,17-bis(oxidanyl)-12-oxabicyclo[12.4.0]octadeca-1(18),2,14,16-tetraene-7,13-dione,3TMS,isomer #2CC1CCC=C(O[Si](C)(C)C)CCCC=CC2=CC(O[Si](C)(C)C)=CC(O[Si](C)(C)C)=C2C(=O)O12892.8Semi standard non polar33892256
(11S)-11-Methyl-15,17-bis(oxidanyl)-12-oxabicyclo[12.4.0]octadeca-1(18),2,14,16-tetraene-7,13-dione,3TMS,isomer #2CC1CCC=C(O[Si](C)(C)C)CCCC=CC2=CC(O[Si](C)(C)C)=CC(O[Si](C)(C)C)=C2C(=O)O12795.7Standard non polar33892256
(11S)-11-Methyl-15,17-bis(oxidanyl)-12-oxabicyclo[12.4.0]octadeca-1(18),2,14,16-tetraene-7,13-dione,3TMS,isomer #2CC1CCC=C(O[Si](C)(C)C)CCCC=CC2=CC(O[Si](C)(C)C)=CC(O[Si](C)(C)C)=C2C(=O)O13528.5Standard polar33892256
(11S)-11-Methyl-15,17-bis(oxidanyl)-12-oxabicyclo[12.4.0]octadeca-1(18),2,14,16-tetraene-7,13-dione,3TBDMS,isomer #1CC1CCCC(O[Si](C)(C)C(C)(C)C)=CCCC=CC2=CC(O[Si](C)(C)C(C)(C)C)=CC(O[Si](C)(C)C(C)(C)C)=C2C(=O)O13588.6Semi standard non polar33892256
(11S)-11-Methyl-15,17-bis(oxidanyl)-12-oxabicyclo[12.4.0]octadeca-1(18),2,14,16-tetraene-7,13-dione,3TBDMS,isomer #1CC1CCCC(O[Si](C)(C)C(C)(C)C)=CCCC=CC2=CC(O[Si](C)(C)C(C)(C)C)=CC(O[Si](C)(C)C(C)(C)C)=C2C(=O)O13315.5Standard non polar33892256
(11S)-11-Methyl-15,17-bis(oxidanyl)-12-oxabicyclo[12.4.0]octadeca-1(18),2,14,16-tetraene-7,13-dione,3TBDMS,isomer #1CC1CCCC(O[Si](C)(C)C(C)(C)C)=CCCC=CC2=CC(O[Si](C)(C)C(C)(C)C)=CC(O[Si](C)(C)C(C)(C)C)=C2C(=O)O13781.5Standard polar33892256
(11S)-11-Methyl-15,17-bis(oxidanyl)-12-oxabicyclo[12.4.0]octadeca-1(18),2,14,16-tetraene-7,13-dione,3TBDMS,isomer #2CC1CCC=C(O[Si](C)(C)C(C)(C)C)CCCC=CC2=CC(O[Si](C)(C)C(C)(C)C)=CC(O[Si](C)(C)C(C)(C)C)=C2C(=O)O13575.1Semi standard non polar33892256
(11S)-11-Methyl-15,17-bis(oxidanyl)-12-oxabicyclo[12.4.0]octadeca-1(18),2,14,16-tetraene-7,13-dione,3TBDMS,isomer #2CC1CCC=C(O[Si](C)(C)C(C)(C)C)CCCC=CC2=CC(O[Si](C)(C)C(C)(C)C)=CC(O[Si](C)(C)C(C)(C)C)=C2C(=O)O13318.3Standard non polar33892256
(11S)-11-Methyl-15,17-bis(oxidanyl)-12-oxabicyclo[12.4.0]octadeca-1(18),2,14,16-tetraene-7,13-dione,3TBDMS,isomer #2CC1CCC=C(O[Si](C)(C)C(C)(C)C)CCCC=CC2=CC(O[Si](C)(C)C(C)(C)C)=CC(O[Si](C)(C)C(C)(C)C)=C2C(=O)O13760.5Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - (11S)-11-Methyl-15,17-bis(oxidanyl)-12-oxabicyclo[12.4.0]octadeca-1(18),2,14,16-tetraene-7,13-dione GC-MS (Non-derivatized) - 70eV, Positivesplash10-0gb9-0079000000-a5f99120af30aa8cb9782021-09-23Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (11S)-11-Methyl-15,17-bis(oxidanyl)-12-oxabicyclo[12.4.0]octadeca-1(18),2,14,16-tetraene-7,13-dione GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (11S)-11-Methyl-15,17-bis(oxidanyl)-12-oxabicyclo[12.4.0]octadeca-1(18),2,14,16-tetraene-7,13-dione GC-MS (TMS_1_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (11S)-11-Methyl-15,17-bis(oxidanyl)-12-oxabicyclo[12.4.0]octadeca-1(18),2,14,16-tetraene-7,13-dione GC-MS (TMS_1_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (11S)-11-Methyl-15,17-bis(oxidanyl)-12-oxabicyclo[12.4.0]octadeca-1(18),2,14,16-tetraene-7,13-dione GC-MS (TMS_1_3) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (11S)-11-Methyl-15,17-bis(oxidanyl)-12-oxabicyclo[12.4.0]octadeca-1(18),2,14,16-tetraene-7,13-dione GC-MS (TMS_1_4) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (11S)-11-Methyl-15,17-bis(oxidanyl)-12-oxabicyclo[12.4.0]octadeca-1(18),2,14,16-tetraene-7,13-dione GC-MS (TMS_2_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (11S)-11-Methyl-15,17-bis(oxidanyl)-12-oxabicyclo[12.4.0]octadeca-1(18),2,14,16-tetraene-7,13-dione GC-MS (TMS_2_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (11S)-11-Methyl-15,17-bis(oxidanyl)-12-oxabicyclo[12.4.0]octadeca-1(18),2,14,16-tetraene-7,13-dione GC-MS (TMS_2_3) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (11S)-11-Methyl-15,17-bis(oxidanyl)-12-oxabicyclo[12.4.0]octadeca-1(18),2,14,16-tetraene-7,13-dione GC-MS (TMS_2_4) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (11S)-11-Methyl-15,17-bis(oxidanyl)-12-oxabicyclo[12.4.0]octadeca-1(18),2,14,16-tetraene-7,13-dione GC-MS (TMS_2_5) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (11S)-11-Methyl-15,17-bis(oxidanyl)-12-oxabicyclo[12.4.0]octadeca-1(18),2,14,16-tetraene-7,13-dione GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (11S)-11-Methyl-15,17-bis(oxidanyl)-12-oxabicyclo[12.4.0]octadeca-1(18),2,14,16-tetraene-7,13-dione GC-MS (TBDMS_1_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (11S)-11-Methyl-15,17-bis(oxidanyl)-12-oxabicyclo[12.4.0]octadeca-1(18),2,14,16-tetraene-7,13-dione GC-MS (TBDMS_1_3) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (11S)-11-Methyl-15,17-bis(oxidanyl)-12-oxabicyclo[12.4.0]octadeca-1(18),2,14,16-tetraene-7,13-dione GC-MS (TBDMS_1_4) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (11S)-11-Methyl-15,17-bis(oxidanyl)-12-oxabicyclo[12.4.0]octadeca-1(18),2,14,16-tetraene-7,13-dione GC-MS (TBDMS_2_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (11S)-11-Methyl-15,17-bis(oxidanyl)-12-oxabicyclo[12.4.0]octadeca-1(18),2,14,16-tetraene-7,13-dione GC-MS (TBDMS_2_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (11S)-11-Methyl-15,17-bis(oxidanyl)-12-oxabicyclo[12.4.0]octadeca-1(18),2,14,16-tetraene-7,13-dione GC-MS (TBDMS_2_3) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (11S)-11-Methyl-15,17-bis(oxidanyl)-12-oxabicyclo[12.4.0]octadeca-1(18),2,14,16-tetraene-7,13-dione GC-MS (TBDMS_2_4) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (11S)-11-Methyl-15,17-bis(oxidanyl)-12-oxabicyclo[12.4.0]octadeca-1(18),2,14,16-tetraene-7,13-dione GC-MS (TBDMS_2_5) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - (11S)-11-Methyl-15,17-bis(oxidanyl)-12-oxabicyclo[12.4.0]octadeca-1(18),2,14,16-tetraene-7,13-dione 20V, Positive-QTOFsplash10-0019-0590000000-6df66bc7b2780592a9332021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - (11S)-11-Methyl-15,17-bis(oxidanyl)-12-oxabicyclo[12.4.0]octadeca-1(18),2,14,16-tetraene-7,13-dione 10V, Positive-QTOFsplash10-0uxr-0049000000-965a646aa19d4fa896382021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - (11S)-11-Methyl-15,17-bis(oxidanyl)-12-oxabicyclo[12.4.0]octadeca-1(18),2,14,16-tetraene-7,13-dione 30V, Positive-QTOFsplash10-000i-0940000000-30e08d041bbb8eb2e1072021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - (11S)-11-Methyl-15,17-bis(oxidanyl)-12-oxabicyclo[12.4.0]octadeca-1(18),2,14,16-tetraene-7,13-dione 40V, Positive-QTOFsplash10-0550-0910000000-821882fe721124fb6f9a2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - (11S)-11-Methyl-15,17-bis(oxidanyl)-12-oxabicyclo[12.4.0]octadeca-1(18),2,14,16-tetraene-7,13-dione 40V, Positive-QTOFsplash10-0550-0910000000-29837a7a5c86b30e648c2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - (11S)-11-Methyl-15,17-bis(oxidanyl)-12-oxabicyclo[12.4.0]octadeca-1(18),2,14,16-tetraene-7,13-dione 50V, Positive-QTOFsplash10-06vi-0900000000-978368a622cd1074a77b2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - (11S)-11-Methyl-15,17-bis(oxidanyl)-12-oxabicyclo[12.4.0]octadeca-1(18),2,14,16-tetraene-7,13-dione 50V, Positive-QTOFsplash10-06vi-0900000000-67d2aad88f2270f5ef052021-09-20HMDB team, MONAView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID145156
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound165628
PDB IDNot Available
ChEBI ID125462
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]