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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 18:41:20 UTC
Update Date2022-03-07 02:53:54 UTC
HMDB IDHMDB0033914
Secondary Accession Numbers
  • HMDB33914
Metabolite Identification
Common NameAegelinol
DescriptionAegelinol belongs to the class of organic compounds known as linear pyranocoumarins. These are organic compounds containing a pyran (or a hydrogenated derivative) linearly fused to a coumarin moiety. Aegelinol has been detected, but not quantified in, fruits. This could make aegelinol a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Aegelinol.
Structure
Data?1563862480
Synonyms
ValueSource
AegelinolMeSH
Chemical FormulaC14H14O4
Average Molecular Weight246.2586
Monoisotopic Molecular Weight246.089208936
IUPAC Name12-hydroxy-13,13-dimethyl-4,14-dioxatricyclo[8.4.0.0³,⁸]tetradeca-1(10),2,6,8-tetraen-5-one
Traditional Name12-hydroxy-13,13-dimethyl-4,14-dioxatricyclo[8.4.0.0³,⁸]tetradeca-1(10),2,6,8-tetraen-5-one
CAS Registry Number21860-31-1
SMILES
CC1(C)OC2=C(CC1O)C=C1C=CC(=O)OC1=C2
InChI Identifier
InChI=1S/C14H14O4/c1-14(2)12(15)6-9-5-8-3-4-13(16)17-10(8)7-11(9)18-14/h3-5,7,12,15H,6H2,1-2H3
InChI KeyBGXFQDFSVDZUIW-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as linear pyranocoumarins. These are organic compounds containing a pyran (or a hydrogenated derivative) linearly fused to a coumarin moiety.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassCoumarins and derivatives
Sub ClassPyranocoumarins
Direct ParentLinear pyranocoumarins
Alternative Parents
Substituents
  • Linear pyranocoumarin
  • Pyranochromene
  • 2,2-dimethyl-1-benzopyran
  • Chromane
  • Benzopyran
  • 1-benzopyran
  • Alkyl aryl ether
  • Pyranone
  • Benzenoid
  • Pyran
  • Heteroaromatic compound
  • Lactone
  • Secondary alcohol
  • Ether
  • Oxacycle
  • Organoheterocyclic compound
  • Alcohol
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point181.5 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.51 g/LALOGPS
logP2.11ALOGPS
logP1.73ChemAxon
logS-2.7ALOGPS
pKa (Strongest Acidic)13.82ChemAxon
pKa (Strongest Basic)-3.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area55.76 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity66.34 m³·mol⁻¹ChemAxon
Polarizability25.64 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+157.73531661259
DarkChem[M-H]-156.40231661259
DeepCCS[M+H]+153.77230932474
DeepCCS[M-H]-151.41430932474
DeepCCS[M-2H]-184.5330932474
DeepCCS[M+Na]+159.86530932474
AllCCS[M+H]+155.532859911
AllCCS[M+H-H2O]+151.532859911
AllCCS[M+NH4]+159.232859911
AllCCS[M+Na]+160.332859911
AllCCS[M-H]-160.332859911
AllCCS[M+Na-2H]-159.932859911
AllCCS[M+HCOO]-159.632859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
AegelinolCC1(C)OC2=C(CC1O)C=C1C=CC(=O)OC1=C23063.9Standard polar33892256
AegelinolCC1(C)OC2=C(CC1O)C=C1C=CC(=O)OC1=C22210.7Standard non polar33892256
AegelinolCC1(C)OC2=C(CC1O)C=C1C=CC(=O)OC1=C22380.5Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Aegelinol,1TMS,isomer #1CC1(C)OC2=CC3=C(C=CC(=O)O3)C=C2CC1O[Si](C)(C)C2350.1Semi standard non polar33892256
Aegelinol,1TBDMS,isomer #1CC1(C)OC2=CC3=C(C=CC(=O)O3)C=C2CC1O[Si](C)(C)C(C)(C)C2589.4Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Aegelinol GC-MS (Non-derivatized) - 70eV, Positivesplash10-0gdi-0490000000-e7fc83035c6f99aed97c2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Aegelinol GC-MS (1 TMS) - 70eV, Positivesplash10-00fr-9063000000-7a3fa268a498538b4ef42017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Aegelinol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Aegelinol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Aegelinol GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-11-03Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Aegelinol 10V, Positive-QTOFsplash10-002b-0290000000-beb30e1d80b0583558f52015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Aegelinol 20V, Positive-QTOFsplash10-004i-0940000000-6dc141905504fecbae9b2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Aegelinol 40V, Positive-QTOFsplash10-000i-4920000000-75ec84f1ae29cdad30362015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Aegelinol 10V, Negative-QTOFsplash10-0002-0190000000-df831bf377cf613c41502015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Aegelinol 20V, Negative-QTOFsplash10-00dj-7690000000-e8ac88f6e0b73a2e89f72015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Aegelinol 40V, Negative-QTOFsplash10-00fr-3910000000-f8d6d80f540df40527ea2015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Aegelinol 10V, Negative-QTOFsplash10-0002-0090000000-49b187996115fce25cbb2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Aegelinol 20V, Negative-QTOFsplash10-002b-0290000000-603bdf7c7a1ccd3b11f22021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Aegelinol 40V, Negative-QTOFsplash10-0002-1980000000-7e11d70a556dc388f8322021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Aegelinol 10V, Positive-QTOFsplash10-0002-0090000000-967054133d39674d9ee82021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Aegelinol 20V, Positive-QTOFsplash10-004j-1590000000-975fe21df9e64e9961642021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Aegelinol 40V, Positive-QTOFsplash10-0ftf-3970000000-b0806b2ad89d736c33ea2021-09-22Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
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
FooDB IDFDB012112
KNApSAcK IDC00054858
Chemspider ID522219
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem CompoundNot Available
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. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .