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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 19:03:36 UTC
Update Date2020-04-22 16:24:14 UTC
HMDB IDHMDB0034256
Secondary Accession Numbers
  • HMDB34256
Metabolite Identification
Common Name(+)-Sesamin
Description(+)-Sesamin, also known as fagarol or sezamin, belongs to the class of organic compounds known as furanoid lignans. These are lignans with a structure that contains either a tetrahydrofuran ring, a furan ring, or a furofuan ring system, that arises from the joining of the two phenylpropanoid units. (+)-Sesamin is an extremely weak basic (essentially neutral) compound (based on its pKa). (+)-Sesamin is found, on average, in the highest concentration within sesames. (+)-Sesamin has also been detected, but not quantified in, several different foods, such as fats and oils, flaxseeds, ginkgo nuts, and ucuhuba. This could make (+)-sesamin a potential biomarker for the consumption of these foods.
Structure
Data?1587572654
Synonyms
ValueSource
FagarolChEBI
SezaminChEBI
AsarininMeSH
Sesamin, (1R-(1alpha,3aalpha,4alpha,6aalpha))-isomerMeSH
Sesamin, (1R-(1alpha,3aalpha,4beta,6aalpha))-isomerMeSH
Epi-sesaminMeSH
EpisesaminMeSH
(+)-SesaminKEGG
SesaminHMDB
Tetrahydro-1,4-bis[3,4-(methylenedioxy)phenyl]-1H,3H-furo[3,4-c]furanHMDB
delta-SesaminHMDB
δ-SesaminHMDB
Chemical FormulaC20H18O6
Average Molecular Weight354.3533
Monoisotopic Molecular Weight354.110338308
IUPAC Name5-[(1S,3aR,4S,6aR)-4-(2H-1,3-benzodioxol-5-yl)-hexahydrofuro[3,4-c]furan-1-yl]-2H-1,3-benzodioxole
Traditional Nameasarinin
CAS Registry Number607-80-7
SMILES
[H][C@]12CO[C@H](C3=CC4=C(OCO4)C=C3)[C@@]1([H])CO[C@@H]2C1=CC2=C(OCO2)C=C1
InChI Identifier
InChI=1S/C20H18O6/c1-3-15-17(25-9-23-15)5-11(1)19-13-7-22-20(14(13)8-21-19)12-2-4-16-18(6-12)26-10-24-16/h1-6,13-14,19-20H,7-10H2/t13-,14-,19+,20+/m0/s1
InChI KeyPEYUIKBAABKQKQ-AFHBHXEDSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as furanoid lignans. These are lignans with a structure that contains either a tetrahydrofuran ring, a furan ring, or a furofuan ring system, that arises from the joining of the two phenylpropanoid units.
KingdomOrganic compounds
Super ClassLignans, neolignans and related compounds
ClassFuranoid lignans
Sub ClassNot Available
Direct ParentFuranoid lignans
Alternative Parents
Substituents
  • Furanoid lignan
  • Furofuran lignan skeleton
  • Benzodioxole
  • Furofuran
  • Benzenoid
  • Tetrahydrofuran
  • Oxacycle
  • Organoheterocyclic compound
  • Ether
  • Dialkyl ether
  • Acetal
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Role

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point123 - 124 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.022 g/LALOGPS
logP2.25ALOGPS
logP2.45ChemAxon
logS-4.2ALOGPS
pKa (Strongest Basic)-3.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area55.38 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity89.75 m³·mol⁻¹ChemAxon
Polarizability36.74 ųChemAxon
Number of Rings6ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0009000000-52b92cdf3788c927f1b3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-0039000000-ae77698e6d7ea0ef074bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0zfr-9801000000-2a9f47a5ff4cf46cac04Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0009000000-5be3689ac3456a0a0cfbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0109000000-18c3d654fd7dc42a2174Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00fs-2941000000-3b70d667ff16839a0be8Spectrum
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 IDFDB012573
KNApSAcK IDC00000601
Chemspider ID65258
KEGG Compound IDC10882
BioCyc IDCPD-8922
BiGG IDNot Available
Wikipedia LinkSesamin
METLIN IDNot Available
PubChem Compound72307
PDB IDNot Available
ChEBI ID66470
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.. .