NP-MRD: Showing NP-Card for Sesamolin (NP0047859)

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Record Information

Version

2.0

Created at

2022-03-17 20:47:07 UTC

Updated at

2022-03-17 20:47:07 UTC

NP-MRD ID

NP0047859

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Sesamolin

Description

Sesamolin 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. Sesamolin is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Sesamolin is found, on average, in the highest concentration within sesames. Sesamolin has also been detected, but not quantified in, fats and oils and flaxseeds. Sesamolin is found in Acronychia laurifolia , Acronychia pedunculata, Clerodendrum trichotomum, Paulownia tomentosa, Sesamum alatum, Sesamum angolense , Sesamum angolrnse, Sesamum angustifolium and Sesamum radiatum. This could make sesamolin a potential biomarker for the consumption of these foods.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 05061307352D          

 27 32  0  0  0  0            999 V2000
    7.8307    1.8125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5452    2.2250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1163    3.0500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7280    0.2775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0961    1.5350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8227    4.3557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2949    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1163    2.2250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3155    0.9920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5086    0.8205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5452    3.0500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8307    3.4625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4018    1.8125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4223    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6481    2.1480    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1760   -0.3356    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.1583    3.6020    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7798    1.0799    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.0023    4.2695    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7798   -0.2549    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7079   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  2  0  0  0  0
  4  2  2  0  0  0  0
 11  1  1  0  0  0  0
 11  5  2  0  0  0  0
 12  2  1  0  0  0  0
 12  6  2  0  0  0  0
 13  7  1  0  0  0  0
 14  8  1  0  0  0  0
 14 13  1  0  0  0  0
 15  3  1  0  0  0  0
 16  4  1  0  0  0  0
 17  5  1  0  0  0  0
 17 15  2  0  0  0  0
 18  6  1  0  0  0  0
 18 16  2  0  0  0  0
 19 11  1  0  0  0  0
 19 13  1  0  0  0  0
 20 14  1  0  0  0  0
 21  8  1  0  0  0  0
 21 19  1  0  0  0  0
 22  7  1  0  0  0  0
 22 20  1  0  0  0  0
 23  9  1  0  0  0  0
 23 15  1  0  0  0  0
 24 10  1  0  0  0  0
 24 16  1  0  0  0  0
 25  9  1  0  0  0  0
 25 17  1  0  0  0  0
 26 10  1  0  0  0  0
 26 18  1  0  0  0  0
 27 12  1  0  0  0  0
 27 20  1  0  0  0  0
M  END


  Mrv0541 05061307352D          

 27 32  0  0  0  0            999 V2000
    7.8307    1.8125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5452    2.2250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1163    3.0500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7280    0.2775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0961    1.5350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8227    4.3557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2949    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1163    2.2250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3155    0.9920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5086    0.8205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5452    3.0500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8307    3.4625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4018    1.8125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4223    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6481    2.1480    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1760   -0.3356    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.1583    3.6020    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7798    1.0799    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.0023    4.2695    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7798   -0.2549    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7079   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  2  0  0  0  0
  4  2  2  0  0  0  0
 11  1  1  0  0  0  0
 11  5  2  0  0  0  0
 12  2  1  0  0  0  0
 12  6  2  0  0  0  0
 13  7  1  0  0  0  0
 14  8  1  0  0  0  0
 14 13  1  0  0  0  0
 15  3  1  0  0  0  0
 16  4  1  0  0  0  0
 17  5  1  0  0  0  0
 17 15  2  0  0  0  0
 18  6  1  0  0  0  0
 18 16  2  0  0  0  0
 19 11  1  0  0  0  0
 19 13  1  0  0  0  0
 20 14  1  0  0  0  0
 21  8  1  0  0  0  0
 21 19  1  0  0  0  0
 22  7  1  0  0  0  0
 22 20  1  0  0  0  0
 23  9  1  0  0  0  0
 23 15  1  0  0  0  0
 24 10  1  0  0  0  0
 24 16  1  0  0  0  0
 25  9  1  0  0  0  0
 25 17  1  0  0  0  0
 26 10  1  0  0  0  0
 26 18  1  0  0  0  0
 27 12  1  0  0  0  0
 27 20  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0047859

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C1OC2=C(O1)C=C(OC1OCC3C1COC3C1=CC3=C(OCO3)C=C1)C=C2

> <INCHI_IDENTIFIER>
InChI=1S/C20H18O7/c1-3-15-17(25-9-23-15)5-11(1)19-13-7-22-20(14(13)8-21-19)27-12-2-4-16-18(6-12)26-10-24-16/h1-6,13-14,19-20H,7-10H2

> <INCHI_KEY>
ZZMNWJVJUKMZJY-UHFFFAOYSA-N

> <FORMULA>
C20H18O7

> <MOLECULAR_WEIGHT>
370.3527

> <EXACT_MASS>
370.10525293

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_AVERAGE_POLARIZABILITY>
37.59432378831447

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5-[4-(2H-1,3-benzodioxol-5-yloxy)-hexahydrofuro[3,4-c]furan-1-yl]-2H-1,3-benzodioxole

> <ALOGPS_LOGP>
2.21

> <JCHEM_LOGP>
2.737558838333333

> <ALOGPS_LOGS>
-3.56

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-3.7968570256106493

> <JCHEM_POLAR_SURFACE_AREA>
64.61000000000001

> <JCHEM_REFRACTIVITY>
90.546

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.02e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
sesamolin

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0      14.617   3.383   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       7.454   1.540   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      15.951   4.153   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.121   2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      13.284   5.693   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.121  -0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      12.559   0.518   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.513   2.865   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      16.469   8.131   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.417   0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      13.284   4.153   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.454   0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      11.789   1.852   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      10.283   1.532   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      15.951   5.693   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.787   1.540   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      14.617   6.463   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.787   0.000   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      11.950   3.383   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      10.122   0.000   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      10.543   4.010   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      11.529  -0.626   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      17.095   6.724   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       3.322   2.016   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0      14.938   7.970   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0       3.322  -0.476   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0       8.788  -0.770   0.000  0.00  0.00           O+0
CONECT    1    3   11                                                       
CONECT    2    4   12                                                       
CONECT    3    1   15                                                       
CONECT    4    2   16                                                       
CONECT    5   11   17                                                       
CONECT    6   12   18                                                       
CONECT    7   13   22                                                       
CONECT    8   14   21                                                       
CONECT    9   23   25                                                       
CONECT   10   24   26                                                       
CONECT   11    1    5   19                                                  
CONECT   12    2    6   27                                                  
CONECT   13    7   14   19                                                  
CONECT   14    8   13   20                                                  
CONECT   15    3   17   23                                                  
CONECT   16    4   18   24                                                  
CONECT   17    5   15   25                                                  
CONECT   18    6   16   26                                                  
CONECT   19   11   13   21                                                  
CONECT   20   14   22   27                                                  
CONECT   21    8   19                                                       
CONECT   22    7   20                                                       
CONECT   23    9   15                                                       
CONECT   24   10   16                                                       
CONECT   25    9   17                                                       
CONECT   26   10   18                                                       
CONECT   27   12   20                                                       
MASTER        0    0    0    0    0    0    0    0   27    0   64    0
END

View in JSmol

Synonyms

Value	Source
(+)-Sesamolin	HMDB
Sesamolinol	HMDB

Chemical Formula

C₂₀H₁₈O₇

Average Mass

370.3527 Da

Monoisotopic Mass

370.10525 Da

IUPAC Name

5-[4-(2H-1,3-benzodioxol-5-yloxy)-hexahydrofuro[3,4-c]furan-1-yl]-2H-1,3-benzodioxole

Traditional Name

sesamolin

CAS Registry Number

526-07-8

SMILES

C1OC2=C(O1)C=C(OC1OCC3C1COC3C1=CC3=C(OCO3)C=C1)C=C2

InChI Identifier

InChI=1S/C20H18O7/c1-3-15-17(25-9-23-15)5-11(1)19-13-7-22-20(14(13)8-21-19)27-12-2-4-16-18(6-12)26-10-24-16/h1-6,13-14,19-20H,7-10H2

InChI Key

ZZMNWJVJUKMZJY-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Acronychia laurifolia	Plant	KNApSAcK
Acronychia pedunculata	LOTUS Database	35616633
Clerodendrum trichotomum	LOTUS Database	35616633
Linum usitatissimum	FooDB	PHENOL EXPLORER
Paulownia tomentosa	LOTUS Database	35616633
Sesamum alatum	Plant	KNApSAcK
Sesamum angolense	Plant	KNApSAcK
Sesamum angolrnse	Plant	KNApSAcK
Sesamum angustifolium	Plant	KNApSAcK
Sesamum indicum	FooDB	KNAPSACK
Sesamum radiatum	Plant	KNApSAcK

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.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzodioxoles

Sub Class

Not Available

Direct Parent

Benzodioxoles

Alternative Parents

Substituents

Benzodioxole
Furofuran
Benzenoid
Tetrahydrofuran
Oxacycle
Ether
Dialkyl ether
Acetal
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

a lignan (CPD-8928 )

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	2.21	ALOGPS
logP	2.74	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Basic)	-3.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	64.61 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	90.55 m³·mol⁻¹	ChemAxon
Polarizability	37.59 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0034119

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB012387

KNApSAcK ID

C00000639

Chemspider ID

509377

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Sesamolin

METLIN ID

Not Available

PubChem Compound

585998

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Sesamolin (NP0047859)

MOL for NP0047859 (Sesamolin)

3D MOL for NP0047859 (Sesamolin)

3D SDF for NP0047859 (Sesamolin)

3D-SDF for NP0047859 (Sesamolin)

PDB for NP0047859 (Sesamolin)

3D PDB for NP0047859 (Sesamolin)

SMILES for NP0047859 (Sesamolin)

INCHI for NP0047859 (Sesamolin)

Structure for NP0047859 (Sesamolin)

3D Structure for NP0047859 (Sesamolin)