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Showing Compound Seselin (FDB012574)

Record Information
Version1.0
Creation date2010-04-08 22:10:15 UTC
Update date2019-11-26 03:07:07 UTC
Primary IDFDB012574
Secondary Accession NumbersNot Available
Chemical Information
FooDB 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). Seselin has been detected, but not quantified in, several different foods, such as lemons, mandarin orange (clementine, tangerine), sweet oranges, anises, and fennels. This could make seselin a potential biomarker for the consumption of these foods.
CAS Number523-59-1
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
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
2H,8H-Benzo(1,2-b:3,4-b')dipyran-2-one, 8,8-dimethyl-biospider
2H,8H-Benzo[1,2-b:3,4-b']dipyran-2-one, 8,8-dimethyl-biospider
8,8-Dimethyl-2H,8H-benzo[1,2-b:3,4-b']dipyran-2-one, 9CIdb_source
8,8-Dimethyl-2H,8H-pyrano[2,3-f]chromen-2-onebiospider
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
Chemical FormulaC14H12O3
IUPAC name8,8-dimethyl-2H,8H-pyrano[2,3-h]chromen-2-one
InChI IdentifierInChI=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
Isomeric SMILESCC1(C)OC2=C(C=C1)C1=C(C=CC(=O)O1)C=C2
Average Molecular Weight228.247
Monoisotopic Molecular Weight228.078644246
Classification
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:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 73.67%; H 5.30%; O 21.03%DFC
Melting PointMp 119-120°DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV Data327 (e 5250) (EtOH) (Berdy)DFC
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSSeselin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0j7r-1960000000-f71d1ee8ecbd8aa8adddSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0090000000-f2cc6b8594e32378fd2eSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-0490000000-178b79bfec179896733aSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00rl-2900000000-69550ecd48575335803cSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0190000000-47aaf3dca13f1cacd42fSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-0390000000-5a6dd1332d117ad1ebd3Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-07vi-0920000000-9bc9f11ee78ed297789eSpectrum
NMRNot Available
ChemSpider ID61531
ChEMBL IDCHEMBL71358
KEGG Compound IDC09312
Pubchem Compound ID68229
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB34257
CRC / DFC (Dictionary of Food Compounds) IDHJB98-V:HJB98-V
EAFUS IDNot Available
Dr. Duke IDSESELIN
BIGG IDNot Available
KNApSAcK IDC00000300
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
anti leukemic35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
fungicide24127 A substance used to destroy fungal pests.DUKE
pesticide25944 Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.DUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.