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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 19:03:36 UTC
Update Date2022-03-07 02:54:02 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
Epi-sesaminMeSH
EpisesaminMeSH
Sesamin, (1R-(1alpha,3aalpha,4alpha,6aalpha))-isomerMeSH
Sesamin, (1R-(1alpha,3aalpha,4beta,6aalpha))-isomerMeSH
(+)-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
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point123 - 124 °CNot Available
Boiling Point504.00 to 505.00 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility6.56 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP4.064 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M-2H]-214.77130932474
DeepCCS[M+Na]+190.82430932474
AllCCS[M+H]+185.832859911
AllCCS[M+H-H2O]+182.632859911
AllCCS[M+NH4]+188.732859911
AllCCS[M+Na]+189.632859911
AllCCS[M-H]-189.432859911
AllCCS[M+Na-2H]-188.932859911
AllCCS[M+HCOO]-188.532859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
(+)-Sesamin[H][C@]12CO[C@H](C3=CC4=C(OCO4)C=C3)[C@@]1([H])CO[C@@H]2C1=CC2=C(OCO2)C=C14269.6Standard polar33892256
(+)-Sesamin[H][C@]12CO[C@H](C3=CC4=C(OCO4)C=C3)[C@@]1([H])CO[C@@H]2C1=CC2=C(OCO2)C=C12737.9Standard non polar33892256
(+)-Sesamin[H][C@]12CO[C@H](C3=CC4=C(OCO4)C=C3)[C@@]1([H])CO[C@@H]2C1=CC2=C(OCO2)C=C13183.1Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - (+)-Sesamin 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 - (+)-Sesamin 10V, Positive-QTOFsplash10-0a4i-0009000000-52b92cdf3788c927f1b32019-02-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (+)-Sesamin 20V, Positive-QTOFsplash10-0a4i-0039000000-ae77698e6d7ea0ef074b2019-02-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (+)-Sesamin 40V, Positive-QTOFsplash10-0zfr-9801000000-2a9f47a5ff4cf46cac042019-02-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (+)-Sesamin 10V, Negative-QTOFsplash10-0udi-0009000000-5be3689ac3456a0a0cfb2019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (+)-Sesamin 20V, Negative-QTOFsplash10-0udi-0109000000-18c3d654fd7dc42a21742019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (+)-Sesamin 40V, Negative-QTOFsplash10-00fs-2941000000-3b70d667ff16839a0be82019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (+)-Sesamin 10V, Negative-QTOFsplash10-0udi-0009000000-b3503695056246b53ddc2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (+)-Sesamin 20V, Negative-QTOFsplash10-0udi-0009000000-edf493bf874ae0340bd82021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (+)-Sesamin 40V, Negative-QTOFsplash10-0udi-0009000000-4c3e7757c2f1f0581e892021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (+)-Sesamin 10V, Positive-QTOFsplash10-0a4i-0019000000-fa3b01674301465ca2f42021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (+)-Sesamin 20V, Positive-QTOFsplash10-0a4i-0059000000-cc75c304155c2d41175b2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (+)-Sesamin 40V, Positive-QTOFsplash10-002r-0859000000-8fd217f0153f310e66192021-09-25Wishart 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 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 IDNot Available
Good Scents IDrw1538831
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.. .