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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 19:03:40 UTC
Update Date2019-07-23 06:15:35 UTC
HMDB IDHMDB0034257
Secondary Accession Numbers
  • HMDB34257
Metabolite Identification
Common NameSeselin
DescriptionSeselin, also known as amyrolin, belongs to the class of organic compounds known as angular pyranocoumarins. These are organic compounds containing a pyran (or a hydrogenated derivative) angularly fused to a coumarin moiety. Seselin is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, seselin has been detected, but not quantified in, several different foods, such as lemons, anises, sweet oranges, mandarin orange (clementine, tangerine), and wild celeries. This could make seselin a potential biomarker for the consumption of these foods.
Structure
Data?1563862535
Synonyms
ValueSource
3',4'-Di-O-(-)-camphanoyl-(+)-cis-khellactoneHMDB
8,8-Dimethyl-2H,8H-benzo(1,2-b:3,4-b')dipyran-2-oneHMDB
8,8-Dimethyl-2H,8H-benzo[1,2-b:3,4-b']dipyran-2-oneHMDB
8,8-Dimethyl-2H,8H-benzo[1,2-b:3,4-b']dipyran-2-one, 9ciHMDB
8,8-Dimethyl-2H,8H-pyrano[2,3-F]chromen-2-oneHMDB
AmyrolinHMDB
Pyranocoumarin deriv.HMDB
SeselineHMDB
Chemical FormulaC14H12O3
Average Molecular Weight228.247
Monoisotopic Molecular Weight228.078644246
IUPAC Name8,8-dimethyl-2H,8H-pyrano[2,3-h]chromen-2-one
Traditional Name8,8-dimethylpyrano[2,3-h]chromen-2-one
CAS Registry Number523-59-1
SMILES
CC1(C)OC2=C(C=C1)C1=C(C=CC(=O)O1)C=C2
InChI Identifier
InChI=1S/C14H12O3/c1-14(2)8-7-10-11(17-14)5-3-9-4-6-12(15)16-13(9)10/h3-8H,1-2H3
InChI KeyQUVCQYQEIOLHFZ-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as angular pyranocoumarins. These are organic compounds containing a pyran (or a hydrogenated derivative) angularly fused to a coumarin moiety.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassCoumarins and derivatives
Sub ClassPyranocoumarins
Direct ParentAngular pyranocoumarins
Alternative Parents
Substituents
  • Angular pyranocoumarin
  • Pyranochromene
  • 2,2-dimethyl-1-benzopyran
  • Benzopyran
  • 1-benzopyran
  • Alkyl aryl ether
  • Pyranone
  • Pyran
  • Benzenoid
  • Heteroaromatic compound
  • Lactone
  • Oxacycle
  • Ether
  • Organoheterocyclic compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organic oxygen compound
  • Organic oxide
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Biological location:

Source:

Role

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point119 - 120 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.04 g/LALOGPS
logP3ALOGPS
logP2.68ChemAxon
logS-3.8ALOGPS
pKa (Strongest Basic)-4.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area35.53 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity65.94 m³·mol⁻¹ChemAxon
Polarizability23.91 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0j7r-1960000000-f71d1ee8ecbd8aa8adddSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0090000000-f2cc6b8594e32378fd2eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-0490000000-178b79bfec179896733aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00rl-2900000000-69550ecd48575335803cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0190000000-47aaf3dca13f1cacd42fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-0390000000-5a6dd1332d117ad1ebd3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-07vi-0920000000-9bc9f11ee78ed297789eSpectrum
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
FooDB IDFDB012574
KNApSAcK IDC00000300
Chemspider ID61531
KEGG Compound IDC09312
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound68229
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB ID
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.. .