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Showing NP-Card for Sesamolinol (NP0047592)

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Record Information
Version2.0
Created at2022-03-17 20:42:43 UTC
Updated at2022-03-17 20:42:43 UTC
NP-MRD IDNP0047592
Secondary Accession NumbersNone
Natural Product Identification
Common NameSesamolinol
DescriptionSesamolinol belongs to the class of organic compounds known as methoxyphenols. Methoxyphenols are compounds containing a methoxy group attached to the benzene ring of a phenol moiety. Sesamolinol is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Sesamolinol is found, on average, in the highest concentration within sesames. Sesamolinol has also been detected, but not quantified in, cereals and cereal products. This could make sesamolinol a potential biomarker for the consumption of these foods.
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0047592 (Sesamolinol)


  Mrv0541 02241220212D          

 27 31  0  0  0  0            999 V2000
    0.7679    1.9408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.2233    3.5579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.2233    2.2644    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3851    1.4554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7387    0.8895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9297    1.1318    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3638    0.5659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4443   -0.2423    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2826   -0.5652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.2233   -0.3229    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0616   -1.1318    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7087   -1.6977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5469   -2.5066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7380   -2.7490    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1721   -2.1831    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3638   -2.5066    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2826   -1.9400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3338   -1.3741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5769   -3.5579    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  9  2  0  0  0  0
  2  3  1  0  0  0  0
  2  6  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 14  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 17  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 19 26  1  0  0  0  0
 20 21  1  0  0  0  0
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 22 23  1  0  0  0  0
 22 27  1  0  0  0  0
 23 24  1  0  0  0  0
 23 26  2  0  0  0  0
 24 25  1  0  0  0  0
M  END
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3D MOL for NP0047592 (Sesamolinol)

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3D SDF for NP0047592 (Sesamolinol)

  Mrv0541 02241220212D          

 27 31  0  0  0  0            999 V2000
    0.7679    1.9408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4151    2.5066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4151    3.3156    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2233    3.5579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7087    2.9115    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2233    2.2644    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3851    1.4554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7387    0.8895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9297    1.1318    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3638    0.5659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4443   -0.2423    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2826   -0.5652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8485    0.0812    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4443    0.7276    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0102    1.3749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7380    1.0513    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6574    0.1618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2233   -0.3229    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0616   -1.1318    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7087   -1.6977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5469   -2.5066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7380   -2.7490    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1721   -2.1831    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3638   -2.5066    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2826   -1.9400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3338   -1.3741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5769   -3.5579    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  9  2  0  0  0  0
  2  3  1  0  0  0  0
  2  6  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 14  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 17  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 19 26  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 22 27  1  0  0  0  0
 23 24  1  0  0  0  0
 23 26  2  0  0  0  0
 24 25  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0047592

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(OC2OCC3C2COC3C2=CC3=C(OCO3)C=C2)=CC=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C20H20O7/c1-22-17-7-12(3-4-15(17)21)27-20-14-9-23-19(13(14)8-24-20)11-2-5-16-18(6-11)26-10-25-16/h2-7,13-14,19-21H,8-10H2,1H3

> <INCHI_KEY>
OJVGWDJIYBTWDS-UHFFFAOYSA-N

> <FORMULA>
C20H20O7

> <MOLECULAR_WEIGHT>
372.3686

> <EXACT_MASS>
372.120902994

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_AVERAGE_POLARIZABILITY>
38.13629465778335

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-{[4-(2H-1,3-benzodioxol-5-yl)-hexahydrofuro[3,4-c]furan-1-yl]oxy}-2-methoxyphenol

> <ALOGPS_LOGP>
2.15

> <JCHEM_LOGP>
2.653088783333333

> <ALOGPS_LOGS>
-3.54

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.277612395629701

> <JCHEM_PKA_STRONGEST_BASIC>
-3.812399327664122

> <JCHEM_POLAR_SURFACE_AREA>
75.61000000000001

> <JCHEM_REFRACTIVITY>
93.22320000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.08e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-{[4-(2H-1,3-benzodioxol-5-yl)-hexahydrofuro[3,4-c]furan-1-yl]oxy}-2-methoxyphenol

> <JCHEM_VEBER_RULE>
0

$$$$

Download
3D-SDF for NP0047592 (Sesamolinol)
Download
PDB for NP0047592 (Sesamolinol)
HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0       1.433   3.623   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.642   4.679   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       2.642   6.189   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       4.150   6.641   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       5.056   5.435   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       4.150   4.227   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.452   2.717   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.246   1.660   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.735   2.113   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.679   1.056   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       0.829  -0.452   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      -0.528  -1.055   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.584   0.152   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.829   1.358   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -1.886   2.566   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -3.244   1.962   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      -3.094   0.302   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -4.150  -0.603   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      -3.848  -2.113   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -5.056  -3.169   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -4.754  -4.679   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -3.244  -5.131   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -2.188  -4.075   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      -0.679  -4.679   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       0.528  -3.621   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -2.490  -2.565   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      -2.944  -6.641   0.000  0.00  0.00           O+0
CONECT    1    2    9                                                       
CONECT    2    1    3    6                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    2    5    7                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    1    8   10                                                  
CONECT   10    9   11   14                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   17                                                  
CONECT   14   10   13   15                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   13   16   18                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20   26                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23   27                                                  
CONECT   23   22   24   26                                                  
CONECT   24   23   25                                                       
CONECT   25   24                                                            
CONECT   26   19   23                                                       
CONECT   27   22                                                            
MASTER        0    0    0    0    0    0    0    0   27    0   62    0
END

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3D PDB for NP0047592 (Sesamolinol)
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SMILES for NP0047592 (Sesamolinol)
COC1=CC(OC2OCC3C2COC3C2=CC3=C(OCO3)C=C2)=CC=C1O
Download
INCHI for NP0047592 (Sesamolinol)
InChI=1S/C20H20O7/c1-22-17-7-12(3-4-15(17)21)27-20-14-9-23-19(13(14)8-24-20)11-2-5-16-18(6-11)26-10-25-16/h2-7,13-14,19-21H,8-10H2,1H3
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View in JSmol
SynonymsNot Available
Chemical FormulaC20H20O7
Average Mass372.3686 Da
Monoisotopic Mass372.12090 Da
IUPAC Name4-{[4-(2H-1,3-benzodioxol-5-yl)-hexahydrofuro[3,4-c]furan-1-yl]oxy}-2-methoxyphenol
Traditional Name4-{[4-(2H-1,3-benzodioxol-5-yl)-hexahydrofuro[3,4-c]furan-1-yl]oxy}-2-methoxyphenol
CAS Registry Number100016-94-2
SMILES
COC1=CC(OC2OCC3C2COC3C2=CC3=C(OCO3)C=C2)=CC=C1O
InChI Identifier
InChI=1S/C20H20O7/c1-22-17-7-12(3-4-15(17)21)27-20-14-9-23-19(13(14)8-24-20)11-2-5-16-18(6-11)26-10-25-16/h2-7,13-14,19-21H,8-10H2,1H3
InChI KeyOJVGWDJIYBTWDS-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 methoxyphenols. Methoxyphenols are compounds containing a methoxy group attached to the benzene ring of a phenol moiety.
KingdomOrganic compounds  
Super ClassBenzenoids  
ClassPhenols  
Sub ClassMethoxyphenols  
Direct ParentMethoxyphenols  
Alternative Parents
Substituents
  • Methoxyphenol
    • 

  • 4-alkoxyphenol
    • 

  • Benzodioxole
    • 

  • Phenoxy compound
    • 

  • Anisole
    • 

  • Methoxybenzene
    • 

  • Phenol ether
    • 

  • Furofuran
    • 

  • 1-hydroxy-2-unsubstituted benzenoid
    • 

  • Alkyl aryl ether
    • 

  • Monocyclic benzene moiety
    • 

  • Tetrahydrofuran
    • 

  • Acetal
    • 

  • Oxacycle
    • 

  • Organoheterocyclic compound
    • 

  • Dialkyl ether
    • 

  • Ether
    • 

  • Hydrocarbon derivative
    • 

  • Organic oxygen compound
    • 

  • 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
logP2.15ALOGPS
logP2.65ChemAxon
logS-3.5ALOGPS
pKa (Strongest Acidic)10.28ChemAxon
pKa (Strongest Basic)-3.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area75.61 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity93.22 m³·mol⁻¹ChemAxon
Polarizability38.14 ųChemAxon
Number of Rings5ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0033270  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB011293  
KNApSAcK IDC00002626  
Chemspider ID3684615  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound4486828  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General ReferencesNot Available