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Showing NP-Card for Sesamol (NP0047747)

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Record Information
Version2.0
Created at2022-03-17 20:45:17 UTC
Updated at2022-03-17 20:45:18 UTC
NP-MRD IDNP0047747
Secondary Accession NumbersNone
Natural Product Identification
Common NameSesamol
DescriptionSesamol, also known as 5-benzodioxolol or sesamol lithium, 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 has been found to be an antioxidant that may prevent the spoilage of oils, It also may prevent the spoilage of oils by acting as an antifungal. Sesamol is an extremely weak basic (essentially neutral) compound (based on its pKa). Sesamol is a natural organic compound which is a component of sesame seeds and sesame oil. Outside of the human body, Sesamol is found, on average, in the highest concentration within sesames. 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. It is sparingly soluble in water, but miscible with most oils. Sesame oil is used in Ayurvedic Medicine. Alexander Shulgin used sesamol in his book PiHKAL to make MMDA-2. It can be used in the synthesis of paroxetine. It can be produced by organic synthesis from heliotropine. Sesamol was first documented in 2010 (PMID: 20015631). It is a white crystalline solid that is a derivative of phenol.
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0047747 (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 NP0047747 (Sesamol)

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3D SDF for NP0047747 (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>
NP0047747

> <DATABASE_NAME>
NP-MRD

> <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

$$$$

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3D-SDF for NP0047747 (Sesamol)
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PDB for NP0047747 (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 NP0047747 (Sesamol)
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SMILES for NP0047747 (Sesamol)
OC1=CC2=C(OCO2)C=C1
Download
INCHI for NP0047747 (Sesamol)
InChI=1S/C7H6O3/c8-5-1-2-6-7(3-5)10-4-9-6/h1-3,8H,4H2
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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
Methylene ether OF oxyhydroquinoneHMDB
Sesamol lithiumHMDB
Sesamol sodiumHMDB
Sesamol titanium (+4)HMDB
Sesamol, ion (1+)HMDB
3,4-MethylenedioxyphenolHMDB
Chemical FormulaC7H6O3
Average Mass138.1207 Da
Monoisotopic Mass138.03169 Da
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
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Sesamum indicumFooDB
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
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
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
HMDB IDHMDB0033812  
DrugBank IDNot Available
Phenol Explorer Compound ID612  
FoodDB 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
Good Scents IDNot Available
References
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  ]