Hmdb loader
Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-12 00:16:46 UTC
Update Date2022-03-07 02:55:59 UTC
HMDB IDHMDB0038931
Secondary Accession Numbers
  • HMDB38931
Metabolite Identification
Common NameSesartemin
DescriptionSesartemin 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. Sesartemin has been detected, but not quantified in, alcoholic beverages and herbs and spices. This could make sesartemin a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Sesartemin.
Structure
Data?1563863283
Synonyms
ValueSource
(+)-SesarteminHMDB
2-(3-Methoxy-4,5-methylenedioxyphenyl)-6-(3,4,5-trimethoxyphenyl)-3,7-dioxabicyclo[3.3.0]octaneHMDB
3,3',4',5'-Tetramethoxy-4,5-methylenedioxy-7,9',7',9-diepoxylignanHMDB
4-Methoxy-6-[tetrahydro-4-(3,4,5-trimethoxyphenyl)-1H,3H-furo[3,4-c]furan-1-yl]-1,3-benzodioxole, 9ciHMDB
Sesartemin-(+)HMDB
Chemical FormulaC23H26O8
Average Molecular Weight430.4477
Monoisotopic Molecular Weight430.162767808
IUPAC Name4-methoxy-6-[4-(3,4,5-trimethoxyphenyl)-hexahydrofuro[3,4-c]furan-1-yl]-2H-1,3-benzodioxole
Traditional Name4-methoxy-6-[4-(3,4,5-trimethoxyphenyl)-hexahydrofuro[3,4-c]furan-1-yl]-2H-1,3-benzodioxole
CAS Registry Number77394-27-5
SMILES
COC1=C2OCOC2=CC(=C1)C1OCC2C1COC2C1=CC(OC)=C(OC)C(OC)=C1
InChI Identifier
InChI=1S/C23H26O8/c1-24-16-5-12(6-17(25-2)22(16)27-4)20-14-9-29-21(15(14)10-28-20)13-7-18(26-3)23-19(8-13)30-11-31-23/h5-8,14-15,20-21H,9-11H2,1-4H3
InChI KeyDHWUVPPRBIJJKS-UHFFFAOYSA-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
  • Phenoxy compound
  • Anisole
  • Methoxybenzene
  • Phenol ether
  • Furofuran
  • Alkyl aryl ether
  • Monocyclic benzene moiety
  • Benzenoid
  • Tetrahydrofuran
  • Acetal
  • Oxacycle
  • Organoheterocyclic compound
  • Dialkyl ether
  • Ether
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point115 - 116 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility5.6 mg/L @ 25 °C (est)The Good Scents Company Information System
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.014 g/LALOGPS
logP2.57ALOGPS
logP2.19ChemAxon
logS-4.5ALOGPS
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area73.84 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity109.83 m³·mol⁻¹ChemAxon
Polarizability45.62 ųChemAxon
Number of Rings5ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+202.42231661259
DarkChem[M-H]-197.70131661259
DeepCCS[M+H]+196.31130932474
DeepCCS[M-H]-193.95330932474
DeepCCS[M-2H]-227.69730932474
DeepCCS[M+Na]+202.92530932474
AllCCS[M+H]+202.832859911
AllCCS[M+H-H2O]+200.232859911
AllCCS[M+NH4]+205.232859911
AllCCS[M+Na]+205.932859911
AllCCS[M-H]-206.732859911
AllCCS[M+Na-2H]-207.232859911
AllCCS[M+HCOO]-208.032859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
SesarteminCOC1=C2OCOC2=CC(=C1)C1OCC2C1COC2C1=CC(OC)=C(OC)C(OC)=C14771.5Standard polar33892256
SesarteminCOC1=C2OCOC2=CC(=C1)C1OCC2C1COC2C1=CC(OC)=C(OC)C(OC)=C13304.0Standard non polar33892256
SesarteminCOC1=C2OCOC2=CC(=C1)C1OCC2C1COC2C1=CC(OC)=C(OC)C(OC)=C13439.4Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Sesartemin GC-MS (Non-derivatized) - 70eV, Positivesplash10-001j-2891200000-e17860db719030249dbf2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Sesartemin 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 - Sesartemin 10V, Positive-QTOFsplash10-001i-0000900000-0204df042e905b5093b42016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sesartemin 20V, Positive-QTOFsplash10-001i-0053900000-8cc1e8bc6bb17b0d876d2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sesartemin 40V, Positive-QTOFsplash10-0gb9-2900000000-71ab41eb6f836cba813f2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sesartemin 10V, Negative-QTOFsplash10-004i-0100900000-28e113a79b11468d6d742016-08-04Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sesartemin 20V, Negative-QTOFsplash10-01u1-0026900000-f1ef98943c19c65a25062016-08-04Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sesartemin 40V, Negative-QTOFsplash10-0a7j-4819000000-61356b47c77e525fab692016-08-04Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sesartemin 10V, Positive-QTOFsplash10-001i-0000900000-65d020dc75e25b88ae492021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sesartemin 20V, Positive-QTOFsplash10-001i-0131900000-f8fd8d62284a7f237e722021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sesartemin 40V, Positive-QTOFsplash10-0uxr-0795800000-68d5720de136f79aceee2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sesartemin 10V, Negative-QTOFsplash10-004i-0000900000-609414267f5ae7afa00a2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sesartemin 20V, Negative-QTOFsplash10-004j-0005900000-66998b89efe188191b942021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sesartemin 40V, Negative-QTOFsplash10-004v-0129500000-3647f5c6f8d3d25d53092021-09-22Wishart 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 IDFDB018403
KNApSAcK IDC00002627
Chemspider ID2962390
KEGG Compound IDC10884
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound3732009
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1872801
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.. .