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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2012-09-11 18:34:59 UTC
Update Date2023-02-21 17:23:38 UTC
HMDB IDHMDB0033812
Secondary Accession Numbers
  • HMDB33812
Metabolite Identification
Common NameSesamol
DescriptionSesamol belongs to the class of organic compounds known as benzodioxoles. These are organic compounds containing a benzene ring fused to either isomers of dioxole. Dioxole is a five-membered unsaturated ring of two oxygen atoms and three carbon atoms. Sesamol is found, on average, in the highest concentration within sesames (Sesamum orientale). Sesamol has also been detected, but not quantified in, fats and oils. This could make sesamol a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on Sesamol.
Structure
Data?1677000218
Synonyms
ValueSource
1, 3-Benzodioxol-5-olHMDB
1,2,4-Benzenetriol methylene etherHMDB
1,3-Benzodioxol-5-olHMDB
1,3-Benzodioxol-5-ol, 9ciHMDB
3,4-(Methylenedioxy)-phenolHMDB
3,4-(Methylenedioxy)phenolHMDB
5-BenzodioxololHMDB
5-Hydroxy-1, 3-benzodioxoleHMDB
5-Hydroxy-1,3-benzodioxoleHMDB, MeSH
Methylene ether OF oxyhydroquinoneHMDB
Sesamol lithiumHMDB, MeSH
Sesamol sodiumHMDB, MeSH
Sesamol titanium (+4)HMDB, MeSH
Sesamol, ion (1+)HMDB, MeSH
3,4-MethylenedioxyphenolMeSH, HMDB
Chemical FormulaC7H6O3
Average Molecular Weight138.1207
Monoisotopic Molecular Weight138.031694058
IUPAC Name2H-1,3-benzodioxol-5-ol
Traditional Namesesamol
CAS Registry Number533-31-3
SMILES
OC1=CC2=C(OCO2)C=C1
InChI Identifier
InChI=1S/C7H6O3/c8-5-1-2-6-7(3-5)10-4-9-6/h1-3,8H,4H2
InChI KeyLUSZGTFNYDARNI-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as benzodioxoles. These are organic compounds containing a benzene ring fused to either isomers of dioxole. Dioxole is a five-membered unsaturated ring of two oxygen atoms and three carbon atoms.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassBenzodioxoles
Sub ClassNot Available
Direct ParentBenzodioxoles
Alternative Parents
Substituents
  • Benzodioxole
  • 1-hydroxy-2-unsubstituted benzenoid
  • Benzenoid
  • Oxacycle
  • Acetal
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • 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 Point65.8 °CNot Available
Boiling Point272.00 to 274.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility0The Good Scents Company Information System
LogP1.253 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility77.3 g/LALOGPS
logP0.89ALOGPS
logP1.29ChemAxon
logS-0.25ALOGPS
pKa (Strongest Acidic)9.79ChemAxon
pKa (Strongest Basic)-4.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area38.69 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity33.81 m³·mol⁻¹ChemAxon
Polarizability13 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+127.61331661259
DarkChem[M-H]-123.95731661259
DeepCCS[M+H]+123.4130932474
DeepCCS[M-H]-119.54230932474
DeepCCS[M-2H]-157.03330932474
DeepCCS[M+Na]+132.52730932474
AllCCS[M+H]+127.832859911
AllCCS[M+H-H2O]+123.032859911
AllCCS[M+NH4]+132.432859911
AllCCS[M+Na]+133.732859911
AllCCS[M-H]-123.432859911
AllCCS[M+Na-2H]-124.532859911
AllCCS[M+HCOO]-125.832859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
SesamolOC1=CC2=C(OCO2)C=C12275.6Standard polar33892256
SesamolOC1=CC2=C(OCO2)C=C11277.5Standard non polar33892256
SesamolOC1=CC2=C(OCO2)C=C11316.9Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Sesamol,1TMS,isomer #1C[Si](C)(C)OC1=CC=C2OCOC2=C11377.8Semi standard non polar33892256
Sesamol,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC=C2OCOC2=C11618.5Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Sesamol GC-MS (Non-derivatized) - 70eV, Positivesplash10-000i-3900000000-f4e897c915ebfdb9b2102017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Sesamol GC-MS (1 TMS) - 70eV, Positivesplash10-00dj-9810000000-5a13228557f3c026594b2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Sesamol 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 - Sesamol 10V, Positive-QTOFsplash10-000i-0900000000-6955e913d40b273c135f2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sesamol 20V, Positive-QTOFsplash10-000i-0900000000-8a0f4bd7021b831ff4e22015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sesamol 40V, Positive-QTOFsplash10-0a4j-9600000000-7c190d3c1f9c1e6535b32015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sesamol 10V, Negative-QTOFsplash10-000i-0900000000-bbad8da71ad16993f41c2015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sesamol 20V, Negative-QTOFsplash10-000i-0900000000-fd0c1b0e49ab7cc2952c2015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sesamol 40V, Negative-QTOFsplash10-000m-9700000000-b88dcfac5372bec389092015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sesamol 10V, Positive-QTOFsplash10-000i-0900000000-ecec1e3d56b5f68558b62021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sesamol 20V, Positive-QTOFsplash10-000i-0900000000-1dcef4f30300b840d5fa2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sesamol 40V, Positive-QTOFsplash10-0aou-9500000000-679b630d2e98a3968cec2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sesamol 10V, Negative-QTOFsplash10-000i-0900000000-f52e9d8c4657a28d3a9f2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sesamol 20V, Negative-QTOFsplash10-000i-0900000000-d3b1c751cc27251f69a02021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sesamol 40V, Negative-QTOFsplash10-066u-9100000000-8e749e47526708b0683f2021-09-24Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)2023-02-04FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)2023-02-04FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)2023-02-04FELIX labView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedCancer patients undergoing total body irradiation details
UrineDetected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedCancer patients undergoing total body irradiation details
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound ID612
FooDB IDFDB011975
KNApSAcK IDC00002673
Chemspider ID61586
KEGG Compound IDC10832
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkSesamol
METLIN IDNot Available
PubChem Compound68289
PDB IDBZX
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1282281
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Chang CC, Lu WJ, Chiang CW, Jayakumar T, Ong ET, Hsiao G, Fong TH, Chou DS, Sheu JR: Potent antiplatelet activity of sesamol in an in vitro and in vivo model: pivotal roles of cyclic AMP and p38 mitogen-activated protein kinase. J Nutr Biochem. 2010 Dec;21(12):1214-21. doi: 10.1016/j.jnutbio.2009.10.009. Epub 2009 Dec 16. [PubMed:20015631 ]
  2. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Enzymes

General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone.
Gene Name:
UGT1A1
Uniprot ID:
P22309
Molecular weight:
59590.91
Reactions
Sesamol → 6-(2H-1,3-benzodioxol-5-yloxy)-3,4,5-trihydroxyoxane-2-carboxylic aciddetails