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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2021-09-11 01:12:56 UTC
Update Date2021-09-26 22:58:06 UTC
HMDB IDHMDB0248043
Secondary Accession NumbersNone
Metabolite Identification
Common Name(3S,7R)-16-Hydroxy-11-methoxy-6,8,19-trioxapentacyclo[10.7.0.02,9.03,7.013,17]nonadeca-1,4,9,11,13(17)-pentaen-18-one
DescriptionAflatoxicol belongs to the class of organic compounds known as angular furanocoumarins. These are furanocoumarins, with a structure characterized by a furan ring angularly fused to a coumarin. Antioxidants such as ellagic acid and inducers of some cytochromes P450, such as indole-3-carbinol, may give a protective effect. Aflatoxicol is an extremely weak basic (essentially neutral) compound (based on its pKa). Aflatoxicol is a potentially toxic compound. Aflatoxicol is a metabolite of aflatoxin B1, one of the mycotoxins from Aspergillus flavus and A. parasiticus. Aflatoxins are metabolized in the liver by the cytochrome P-450-dependent polysubstrate mono-oxygenase system to less toxic metabolites. Singlet oxygen in turn activates them to mutagens and DNA binding species. Protracted exposure to aflatoxins may cause liver damage and necrosis, cholestasis, and hepatomas. Aflatoxins modify the immune system by affecting antibody formation, complement, cell-mediated immunity, and phagocytosis. This compound has been identified in human blood as reported by (PMID: 31557052 ). (3s,7r)-16-hydroxy-11-methoxy-6,8,19-trioxapentacyclo[10.7.0.02,9.03,7.013,17]nonadeca-1,4,9,11,13(17)-pentaen-18-one is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically (3S,7R)-16-Hydroxy-11-methoxy-6,8,19-trioxapentacyclo[10.7.0.02,9.03,7.013,17]nonadeca-1,4,9,11,13(17)-pentaen-18-one 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
Synonyms
ValueSource
Aflatoxicol, (1R-(1alpha,6aalpha,9aalpha))-isomerMeSH
Aflatoxin RMeSH
Chemical FormulaC17H14O6
Average Molecular Weight314.2895
Monoisotopic Molecular Weight314.07903818
IUPAC Name16-hydroxy-11-methoxy-6,8,19-trioxapentacyclo[10.7.0.0²,⁹.0³,⁷.0¹³,¹⁷]nonadeca-1,4,9,11,13(17)-pentaen-18-one
Traditional Name16-hydroxy-11-methoxy-6,8,19-trioxapentacyclo[10.7.0.0²,⁹.0³,⁷.0¹³,¹⁷]nonadeca-1,4,9,11,13(17)-pentaen-18-one
CAS Registry NumberNot Available
SMILES
COC1=C2C3=C(C(O)CC3)C(=O)OC2=C2C3C=COC3OC2=C1
InChI Identifier
InChI=1S/C17H14O6/c1-20-10-6-11-14(8-4-5-21-17(8)22-11)15-13(10)7-2-3-9(18)12(7)16(19)23-15/h4-6,8-9,17-18H,2-3H2,1H3
InChI KeyWYIWLDSPNDMZIT-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as angular furanocoumarins. These are furanocoumarins, with a structure characterized by a furan ring angularly fused to a coumarin.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassCoumarins and derivatives
Sub ClassFuranocoumarins
Direct ParentAngular furanocoumarins
Alternative Parents
Substituents
  • Angular furanocoumarin
  • Benzopyran
  • 1-benzopyran
  • Coumaran
  • Anisole
  • Alkyl aryl ether
  • Pyranone
  • Benzenoid
  • Pyran
  • Heteroaromatic compound
  • Dihydrofuran
  • Secondary alcohol
  • Lactone
  • Acetal
  • Oxacycle
  • Organoheterocyclic compound
  • Ether
  • Hydrocarbon derivative
  • Alcohol
  • Organic oxygen compound
  • Organic oxide
  • Organooxygen compound
  • 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
logP1.19ALOGPS
logP1.02ChemAxon
logS-2.8ALOGPS
pKa (Strongest Acidic)14.28ChemAxon
pKa (Strongest Basic)-3.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area74.22 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity79.41 m³·mol⁻¹ChemAxon
Polarizability30.95 ųChemAxon
Number of Rings5ChemAxon
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]+172.57530932474
DeepCCS[M-H]-170.21730932474
DeepCCS[M-2H]-203.75630932474
DeepCCS[M+Na]+178.98330932474
AllCCS[M+H]+171.232859911
AllCCS[M+H-H2O]+168.032859911
AllCCS[M+NH4]+174.232859911
AllCCS[M+Na]+175.032859911
AllCCS[M-H]-172.232859911
AllCCS[M+Na-2H]-171.332859911
AllCCS[M+HCOO]-170.532859911

Predicted Kovats Retention Indices

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
(3S,7R)-16-Hydroxy-11-methoxy-6,8,19-trioxapentacyclo[10.7.0.02,9.03,7.013,17]nonadeca-1,4,9,11,13(17)-pentaen-18-one,1TMS,isomer #1COC1=CC2=C(C3=C1C1=C(C(=O)O3)C(O[Si](C)(C)C)CC1)C1C=COC1O22945.1Semi standard non polar33892256
(3S,7R)-16-Hydroxy-11-methoxy-6,8,19-trioxapentacyclo[10.7.0.02,9.03,7.013,17]nonadeca-1,4,9,11,13(17)-pentaen-18-one,1TMS,isomer #1COC1=CC2=C(C3=C1C1=C(C(=O)O3)C(O[Si](C)(C)C)CC1)C1C=COC1O22811.1Standard non polar33892256
(3S,7R)-16-Hydroxy-11-methoxy-6,8,19-trioxapentacyclo[10.7.0.02,9.03,7.013,17]nonadeca-1,4,9,11,13(17)-pentaen-18-one,1TMS,isomer #1COC1=CC2=C(C3=C1C1=C(C(=O)O3)C(O[Si](C)(C)C)CC1)C1C=COC1O24009.7Standard polar33892256
(3S,7R)-16-Hydroxy-11-methoxy-6,8,19-trioxapentacyclo[10.7.0.02,9.03,7.013,17]nonadeca-1,4,9,11,13(17)-pentaen-18-one,1TBDMS,isomer #1COC1=CC2=C(C3=C1C1=C(C(=O)O3)C(O[Si](C)(C)C(C)(C)C)CC1)C1C=COC1O23170.7Semi standard non polar33892256
(3S,7R)-16-Hydroxy-11-methoxy-6,8,19-trioxapentacyclo[10.7.0.02,9.03,7.013,17]nonadeca-1,4,9,11,13(17)-pentaen-18-one,1TBDMS,isomer #1COC1=CC2=C(C3=C1C1=C(C(=O)O3)C(O[Si](C)(C)C(C)(C)C)CC1)C1C=COC1O23050.6Standard non polar33892256
(3S,7R)-16-Hydroxy-11-methoxy-6,8,19-trioxapentacyclo[10.7.0.02,9.03,7.013,17]nonadeca-1,4,9,11,13(17)-pentaen-18-one,1TBDMS,isomer #1COC1=CC2=C(C3=C1C1=C(C(=O)O3)C(O[Si](C)(C)C(C)(C)C)CC1)C1C=COC1O24064.5Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - (3S,7R)-16-Hydroxy-11-methoxy-6,8,19-trioxapentacyclo[10.7.0.02,9.03,7.013,17]nonadeca-1,4,9,11,13(17)-pentaen-18-one GC-MS (Non-derivatized) - 70eV, Positivesplash10-00ds-0090000000-3383a3871ef632b3b5972021-09-24Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (3S,7R)-16-Hydroxy-11-methoxy-6,8,19-trioxapentacyclo[10.7.0.02,9.03,7.013,17]nonadeca-1,4,9,11,13(17)-pentaen-18-one GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (3S,7R)-16-Hydroxy-11-methoxy-6,8,19-trioxapentacyclo[10.7.0.02,9.03,7.013,17]nonadeca-1,4,9,11,13(17)-pentaen-18-one GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (3S,7R)-16-Hydroxy-11-methoxy-6,8,19-trioxapentacyclo[10.7.0.02,9.03,7.013,17]nonadeca-1,4,9,11,13(17)-pentaen-18-one 10V, Positive-QTOFsplash10-00kb-0095000000-71c58c811fa86c4f350f2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (3S,7R)-16-Hydroxy-11-methoxy-6,8,19-trioxapentacyclo[10.7.0.02,9.03,7.013,17]nonadeca-1,4,9,11,13(17)-pentaen-18-one 20V, Positive-QTOFsplash10-00kb-0092000000-25d664ddf6f71729d9c92016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (3S,7R)-16-Hydroxy-11-methoxy-6,8,19-trioxapentacyclo[10.7.0.02,9.03,7.013,17]nonadeca-1,4,9,11,13(17)-pentaen-18-one 40V, Positive-QTOFsplash10-07xs-2390000000-d8e7c756bedcdafe8d002016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (3S,7R)-16-Hydroxy-11-methoxy-6,8,19-trioxapentacyclo[10.7.0.02,9.03,7.013,17]nonadeca-1,4,9,11,13(17)-pentaen-18-one 10V, Negative-QTOFsplash10-03di-0059000000-7536a2ca78d64e601ad72016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (3S,7R)-16-Hydroxy-11-methoxy-6,8,19-trioxapentacyclo[10.7.0.02,9.03,7.013,17]nonadeca-1,4,9,11,13(17)-pentaen-18-one 20V, Negative-QTOFsplash10-03dj-0094000000-bdac8584ca3c38da05b22016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (3S,7R)-16-Hydroxy-11-methoxy-6,8,19-trioxapentacyclo[10.7.0.02,9.03,7.013,17]nonadeca-1,4,9,11,13(17)-pentaen-18-one 40V, Negative-QTOFsplash10-0gb9-3190000000-f6139c8985207a374eaa2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (3S,7R)-16-Hydroxy-11-methoxy-6,8,19-trioxapentacyclo[10.7.0.02,9.03,7.013,17]nonadeca-1,4,9,11,13(17)-pentaen-18-one 10V, Negative-QTOFsplash10-03di-0009000000-7c7169b7540bc94558262021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (3S,7R)-16-Hydroxy-11-methoxy-6,8,19-trioxapentacyclo[10.7.0.02,9.03,7.013,17]nonadeca-1,4,9,11,13(17)-pentaen-18-one 20V, Negative-QTOFsplash10-03di-0039000000-cf442be2c6395255469f2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (3S,7R)-16-Hydroxy-11-methoxy-6,8,19-trioxapentacyclo[10.7.0.02,9.03,7.013,17]nonadeca-1,4,9,11,13(17)-pentaen-18-one 40V, Negative-QTOFsplash10-03xs-0292000000-729af1d7e1ce8cc5d2582021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (3S,7R)-16-Hydroxy-11-methoxy-6,8,19-trioxapentacyclo[10.7.0.02,9.03,7.013,17]nonadeca-1,4,9,11,13(17)-pentaen-18-one 10V, Positive-QTOFsplash10-014i-0029000000-c8d393f9a78874956ee02021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (3S,7R)-16-Hydroxy-11-methoxy-6,8,19-trioxapentacyclo[10.7.0.02,9.03,7.013,17]nonadeca-1,4,9,11,13(17)-pentaen-18-one 20V, Positive-QTOFsplash10-014i-0029000000-c8d393f9a78874956ee02021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (3S,7R)-16-Hydroxy-11-methoxy-6,8,19-trioxapentacyclo[10.7.0.02,9.03,7.013,17]nonadeca-1,4,9,11,13(17)-pentaen-18-one 40V, Positive-QTOFsplash10-0a4i-0090000000-6efb3590dae7ff13062b2021-10-12Wishart LabView 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 IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound628754
PDB IDNot Available
ChEBI IDNot Available
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 ]