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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 19:03:40 UTC
Update Date2022-03-07 02:54:02 UTC
HMDB IDHMDB0034257
Secondary Accession Numbers
  • HMDB34257
Metabolite Identification
Common NameSeselin
DescriptionSeselin 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 has been detected, but not quantified in, several different foods, such as mandarin orange (clementine, tangerine), sweet oranges (Citrus sinensis), fennels (Foeniculum vulgare), anises (Pimpinella anisum), and wild celeries (Apium graveolens). This could make seselin a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Seselin.
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
Physiological effectNot Available
Disposition
ProcessNot Available
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point119 - 120 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility60.34 mg/L @ 25 °C (est)The Good Scents Company Information System
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+153.96431661259
DarkChem[M-H]-153.26331661259
DeepCCS[M+H]+157.25730932474
DeepCCS[M-H]-154.89930932474
DeepCCS[M-2H]-187.78530932474
DeepCCS[M+Na]+163.3530932474
AllCCS[M+H]+148.632859911
AllCCS[M+H-H2O]+144.332859911
AllCCS[M+NH4]+152.632859911
AllCCS[M+Na]+153.732859911
AllCCS[M-H]-154.132859911
AllCCS[M+Na-2H]-153.632859911
AllCCS[M+HCOO]-153.232859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
SeselinCC1(C)OC2=C(C=C1)C1=C(C=CC(=O)O1)C=C22809.5Standard polar33892256
SeselinCC1(C)OC2=C(C=C1)C1=C(C=CC(=O)O1)C=C22043.3Standard non polar33892256
SeselinCC1(C)OC2=C(C=C1)C1=C(C=CC(=O)O1)C=C22069.5Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Seselin GC-MS (Non-derivatized) - 70eV, Positivesplash10-0j7r-1960000000-f71d1ee8ecbd8aa8addd2017-07-27Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Seselin 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 - Seselin 10V, Positive-QTOFsplash10-004i-0090000000-f2cc6b8594e32378fd2e2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Seselin 20V, Positive-QTOFsplash10-004i-0490000000-178b79bfec179896733a2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Seselin 40V, Positive-QTOFsplash10-00rl-2900000000-69550ecd48575335803c2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Seselin 10V, Negative-QTOFsplash10-004i-0190000000-47aaf3dca13f1cacd42f2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Seselin 20V, Negative-QTOFsplash10-004i-0390000000-5a6dd1332d117ad1ebd32016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Seselin 40V, Negative-QTOFsplash10-07vi-0920000000-9bc9f11ee78ed297789e2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Seselin 10V, Negative-QTOFsplash10-004i-0090000000-f0e0fc28215258fdeb312021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Seselin 20V, Negative-QTOFsplash10-004r-0490000000-ee41d791a0fff49c7ac92021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Seselin 40V, Negative-QTOFsplash10-0a5j-0900000000-241921d7efd7a8f5f9362021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Seselin 10V, Positive-QTOFsplash10-004i-0090000000-c89325e1a7192ec227f42021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Seselin 20V, Positive-QTOFsplash10-004i-0290000000-d70cfec989c8b56e48562021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Seselin 40V, Positive-QTOFsplash10-0079-0910000000-7042ee8061a0c73e9f762021-09-22Wishart LabView Spectrum
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 IDNot Available
Good Scents IDrw1637191
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.. .