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Showing metabocard for Sesamol (HMDB0033812)

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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
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0033812 (Sesamol)

  Mrv1652309271714242D          

 10 11  0  0  0  0            999 V2000
    2.7845    0.6979    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556    0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435    2.1904    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6284    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435    0.8555    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  4  8  1  0  0  0  0
  5  9  1  0  0  0  0
  9 10  2  0  0  0  0
  2 10  1  0  0  0  0
M  END
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3D MOL for HMDB0033812 (Sesamol)

HMDB0033812
     RDKit          3D
Sesamol
 16 17  0  0  0  0  0  0  0  0999 V2000
   -3.1208   -0.8398    0.2223 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8343   -0.2940    0.1102 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6679    0.9873   -0.3569 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3965    1.5373   -0.4717 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7228    0.8104   -0.1200 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5765   -0.4817    0.3526 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7147   -1.0108    0.4582 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8244   -1.0170    0.6419 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7768   -0.2221   -0.0395 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0977    1.0352   -0.1058 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2121   -1.7848    0.5691 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5399    1.5589   -0.6329 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2509    2.5420   -0.8369 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8485   -2.0233    0.8271 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8466   -0.6449   -1.0812 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7408   -0.1528    0.4634 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
  7  2  1  0
 10  5  1  0
  1 11  1  0
  3 12  1  0
  4 13  1  0
  7 14  1  0
  9 15  1  0
  9 16  1  0
M  END
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3D SDF for HMDB0033812 (Sesamol)

  Mrv1652309271714242D          

 10 11  0  0  0  0            999 V2000
    2.7845    0.6979    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556    0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435    2.1904    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6284    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435    0.8555    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  4  8  1  0  0  0  0
  5  9  1  0  0  0  0
  9 10  2  0  0  0  0
  2 10  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0033812

> <DATABASE_NAME>
hmdb

> <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_KEY>
LUSZGTFNYDARNI-UHFFFAOYSA-N

> <FORMULA>
C7H6O3

> <MOLECULAR_WEIGHT>
138.1207

> <EXACT_MASS>
138.031694058

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
16

> <JCHEM_AVERAGE_POLARIZABILITY>
13.000994139467963

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2H-1,3-benzodioxol-5-ol

> <ALOGPS_LOGP>
0.89

> <JCHEM_LOGP>
1.2929139619999999

> <ALOGPS_LOGS>
-0.25

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.794858956698127

> <JCHEM_PKA_STRONGEST_BASIC>
-4.739368744943291

> <JCHEM_POLAR_SURFACE_AREA>
38.69

> <JCHEM_REFRACTIVITY>
33.8058

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.73e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
sesamol

> <JCHEM_VEBER_RULE>
1

$$$$
Download

3D-SDF for HMDB0033812 (Sesamol)

HMDB0033812
     RDKit          3D
Sesamol
 16 17  0  0  0  0  0  0  0  0999 V2000
   -3.1208   -0.8398    0.2223 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8343   -0.2940    0.1102 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6679    0.9873   -0.3569 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3965    1.5373   -0.4717 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7228    0.8104   -0.1200 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5765   -0.4817    0.3526 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7147   -1.0108    0.4582 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8244   -1.0170    0.6419 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7768   -0.2221   -0.0395 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0977    1.0352   -0.1058 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2121   -1.7848    0.5691 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5399    1.5589   -0.6329 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2509    2.5420   -0.8369 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8485   -2.0233    0.8271 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8466   -0.6449   -1.0812 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7408   -0.1528    0.4634 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
  7  2  1  0
 10  5  1  0
  1 11  1  0
  3 12  1  0
  4 13  1  0
  7 14  1  0
  9 15  1  0
  9 16  1  0
M  END
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PDB for HMDB0033812 (Sesamol)

HEADER    PROTEIN                                 27-SEP-17   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-SEP-17         0                                  
HETATM    1  O   UNK     0       5.198   1.303   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       3.864   2.073   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.530   1.303   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.197   2.073   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.197   3.613   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      -0.268   4.089   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      -1.173   2.843   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -0.268   1.597   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       2.530   4.383   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.864   3.613   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   10                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    8                                                  
CONECT    5    4    6    9                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    4                                                       
CONECT    9    5   10                                                       
CONECT   10    9    2                                                       
MASTER        0    0    0    0    0    0    0    0   10    0   22    0
END
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3D PDB for HMDB0033812 (Sesamol)

COMPND    HMDB0033812
HETATM    1  O1  UNL     1      -3.121  -0.840   0.222  1.00  0.00           O  
HETATM    2  C1  UNL     1      -1.834  -0.294   0.110  1.00  0.00           C  
HETATM    3  C2  UNL     1      -1.668   0.987  -0.357  1.00  0.00           C  
HETATM    4  C3  UNL     1      -0.396   1.537  -0.472  1.00  0.00           C  
HETATM    5  C4  UNL     1       0.723   0.810  -0.120  1.00  0.00           C  
HETATM    6  C5  UNL     1       0.576  -0.482   0.353  1.00  0.00           C  
HETATM    7  C6  UNL     1      -0.715  -1.011   0.458  1.00  0.00           C  
HETATM    8  O2  UNL     1       1.824  -1.017   0.642  1.00  0.00           O  
HETATM    9  C7  UNL     1       2.777  -0.222  -0.039  1.00  0.00           C  
HETATM   10  O3  UNL     1       2.098   1.035  -0.106  1.00  0.00           O  
HETATM   11  H1  UNL     1      -3.212  -1.785   0.569  1.00  0.00           H  
HETATM   12  H2  UNL     1      -2.540   1.559  -0.633  1.00  0.00           H  
HETATM   13  H3  UNL     1      -0.251   2.542  -0.837  1.00  0.00           H  
HETATM   14  H4  UNL     1      -0.848  -2.023   0.827  1.00  0.00           H  
HETATM   15  H5  UNL     1       2.847  -0.645  -1.081  1.00  0.00           H  
HETATM   16  H6  UNL     1       3.741  -0.153   0.463  1.00  0.00           H  
CONECT    1    2   11
CONECT    2    3    3    7
CONECT    3    4   12
CONECT    4    5    5   13
CONECT    5    6   10
CONECT    6    7    7    8
CONECT    7   14
CONECT    8    9
CONECT    9   10   15   16
END
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SMILES for HMDB0033812 (Sesamol)

OC1=CC2=C(OCO2)C=C1
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INCHI for HMDB0033812 (Sesamol)

InChI=1S/C7H6O3/c8-5-1-2-6-7(3-5)10-4-9-6/h1-3,8H,4H2
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View in JSmolView NMR AssignmentsView Stereo Labels
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
Biological locationRoute of exposureSource
ProcessNot Available
Role
Biological 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
Predicted Chromatographic Properties
Spectra
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

Enzyme Details
1. UDP-glucuronosyltransferase 1-1
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