NP-MRD: Showing NP-Card for (-)-Lyoniresinol 9'-O-glucoside (NP0138542)

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Record Information

Version

2.0

Created at

2022-06-29 17:34:21 UTC

Updated at

2022-06-29 17:34:21 UTC

NP-MRD ID

NP0138542

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(-)-Lyoniresinol 9'-O-glucoside

Description

(7'R)-(+)-Lyoniresinol 9'-glucoside belongs to the class of organic compounds known as lignan glycosides. These are aromatic polycyclic compounds containing a carbohydrate component glycosidically linked to a lignan moiety. They include 1-aryltetralin lactones (7'R)-(+)-Lyoniresinol 9'-glucoside is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, (7'R)-(+)-Lyoniresinol 9'-glucoside has been detected, but not quantified in, fruits. (-)-Lyoniresinol 9'-O-glucoside is found in Aegle marmelos, Cordiera sessilis, Annona squamosa, Avicennia marina, Betula platyphylla, Chaenomeles sinensis, Fernandoa adenophylla, Myrsine africana, Quillaja saponaria, Spiraea canescens, Stephania longa, Strobilanthes cusia, Verbena brasiliensis, Walsura robusta and Zanthoxylum petiolare. This could make (7'r)-(+)-lyoniresinol 9'-glucoside a potential biomarker for the consumption of these foods.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 02241211492D          

 41 44  0  0  0  0            999 V2000
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 40 41  1  0  0  0  0
M  END

     RDKit          3D

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M  END


  Mrv0541 02241211492D          

 41 44  0  0  0  0            999 V2000
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   -3.5734    1.6499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2869    2.0623    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2869    2.8873    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2869    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5734    0.8249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8585    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8585   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5734   -0.8249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1421    0.8249    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8571    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5706   -0.8249    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8571   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1421   -0.8249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1421   -1.6499    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5720    0.8249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2869    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  5  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4  9  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  7 18  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 19  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 25  1  0  0  0  0
 17 18  1  0  0  0  0
 17 31  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 34  1  0  0  0  0
 23 24  1  0  0  0  0
 23 38  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 26 30  1  0  0  0  0
 27 28  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 34 35  1  0  0  0  0
 35 37  1  0  0  0  0
 35 40  1  0  0  0  0
 36 37  1  0  0  0  0
 37 38  1  0  0  0  0
 38 39  1  0  0  0  0
 40 41  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0138542

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC2=C(C(C(COC3OC(CO)C(O)C(O)C3O)C(CO)C2)C2=CC(OC)=C(O)C(OC)=C2)C(OC)=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C28H38O13/c1-36-16-7-13(8-17(37-2)22(16)31)20-15(11-40-28-26(35)25(34)23(32)19(10-30)41-28)14(9-29)5-12-6-18(38-3)24(33)27(39-4)21(12)20/h6-8,14-15,19-20,23,25-26,28-35H,5,9-11H2,1-4H3

> <INCHI_KEY>
PQQRNPDHSJDAGV-UHFFFAOYSA-N

> <FORMULA>
C28H38O13

> <MOLECULAR_WEIGHT>
582.5935

> <EXACT_MASS>
582.231241302

> <JCHEM_ACCEPTOR_COUNT>
13

> <JCHEM_AVERAGE_POLARIZABILITY>
59.577588757339754

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-{[7-hydroxy-1-(4-hydroxy-3,5-dimethoxyphenyl)-3-(hydroxymethyl)-6,8-dimethoxy-1,2,3,4-tetrahydronaphthalen-2-yl]methoxy}-6-(hydroxymethyl)oxane-3,4,5-triol

> <ALOGPS_LOGP>
0.22

> <JCHEM_LOGP>
-0.3057398413333321

> <ALOGPS_LOGS>
-3.11

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.882096842181616

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.243163356421457

> <JCHEM_PKA_STRONGEST_BASIC>
-2.6036948192677114

> <JCHEM_POLAR_SURFACE_AREA>
196.98999999999998

> <JCHEM_REFRACTIVITY>
143.2123

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.56e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-{[7-hydroxy-1-(4-hydroxy-3,5-dimethoxyphenyl)-3-(hydroxymethyl)-6,8-dimethoxy-1,2,3,4-tetrahydronaphthalen-2-yl]methoxy}-6-(hydroxymethyl)oxane-3,4,5-triol

> <JCHEM_VEBER_RULE>
0

$$$$

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  O   UNK     0      -0.002  -3.850   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      -0.002  -5.390   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -2.669  -5.390   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      -2.669  -3.850   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.335  -3.080   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.335  -1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.669  -0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -4.004  -1.540   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -4.004  -3.080   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      -5.336  -3.850   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      -5.336  -5.390   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -0.002   5.390   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      -0.002   3.850   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.335   3.080   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -2.669   3.850   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -4.004   3.080   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -4.004   1.540   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -2.669   0.770   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -1.335   1.540   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -0.002   0.770   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       1.332   1.540   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       2.667   0.770   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       2.667  -0.770   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       1.332  -1.540   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      -5.336   3.850   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -6.670   3.080   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      -8.002   3.850   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      -8.002   5.390   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      -8.002   0.770   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      -6.670   1.540   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -5.336   0.770   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      -5.336  -0.770   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0      -6.670  -1.540   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       3.999   1.540   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0       5.333   0.770   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0       6.665  -1.540   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0       5.333  -0.770   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       3.999  -1.540   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0       3.999  -3.080   0.000  0.00  0.00           O+0
HETATM   40  C   UNK     0       6.668   1.540   0.000  0.00  0.00           C+0
HETATM   41  O   UNK     0       8.002   0.770   0.000  0.00  0.00           O+0
CONECT    1    2    5                                                       
CONECT    2    1                                                            
CONECT    3    4                                                            
CONECT    4    3    5    9                                                  
CONECT    5    1    4    6                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   18                                                  
CONECT    8    7    9                                                       
CONECT    9    4    8   10                                                  
CONECT   10    9   11                                                       
CONECT   11   10                                                            
CONECT   12   13                                                            
CONECT   13   12   14                                                       
CONECT   14   13   15   19                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   25                                                  
CONECT   17   16   18   31                                                  
CONECT   18    7   17   19                                                  
CONECT   19   14   18   20                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23   34                                                  
CONECT   23   22   24   38                                                  
CONECT   24   23                                                            
CONECT   25   16   26                                                       
CONECT   26   25   27   30                                                  
CONECT   27   26   28                                                       
CONECT   28   27                                                            
CONECT   29   30                                                            
CONECT   30   26   29   31                                                  
CONECT   31   17   30   32                                                  
CONECT   32   31   33                                                       
CONECT   33   32                                                            
CONECT   34   22   35                                                       
CONECT   35   34   37   40                                                  
CONECT   36   37                                                            
CONECT   37   35   36   38                                                  
CONECT   38   23   37   39                                                  
CONECT   39   38                                                            
CONECT   40   35   41                                                       
CONECT   41   40                                                            
MASTER        0    0    0    0    0    0    0    0   41    0   88    0
END

View in JSmol

Synonyms

Value	Source
(+)-Lyoniresinol 3alpha-O-beta-glucopyranoside	HMDB

Chemical Formula

C₂₈H₃₈O₁₃

Average Mass

582.5935 Da

Monoisotopic Mass

582.23124 Da

IUPAC Name

2-{[7-hydroxy-1-(4-hydroxy-3,5-dimethoxyphenyl)-3-(hydroxymethyl)-6,8-dimethoxy-1,2,3,4-tetrahydronaphthalen-2-yl]methoxy}-6-(hydroxymethyl)oxane-3,4,5-triol

Traditional Name

2-{[7-hydroxy-1-(4-hydroxy-3,5-dimethoxyphenyl)-3-(hydroxymethyl)-6,8-dimethoxy-1,2,3,4-tetrahydronaphthalen-2-yl]methoxy}-6-(hydroxymethyl)oxane-3,4,5-triol

CAS Registry Number

143236-02-6

SMILES

COC1=CC2=C(C(C(COC3OC(CO)C(O)C(O)C3O)C(CO)C2)C2=CC(OC)=C(O)C(OC)=C2)C(OC)=C1O

InChI Identifier

InChI=1S/C28H38O13/c1-36-16-7-13(8-17(37-2)22(16)31)20-15(11-40-28-26(35)25(34)23(32)19(10-30)41-28)14(9-29)5-12-6-18(38-3)24(33)27(39-4)21(12)20/h6-8,14-15,19-20,23,25-26,28-35H,5,9-11H2,1-4H3

InChI Key

PQQRNPDHSJDAGV-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Aegle marmelos	LOTUS Database	35616633
Alibertia sessilis	LOTUS Database	35616633
Annona squamosa	LOTUS Database	35616633
Avicennia marina	LOTUS Database	35616633
Betula platyphylla	LOTUS Database	35616633
Chaenomeles sinensis	LOTUS Database	35616633
Fernandoa adenophylla	LOTUS Database	35616633
Myrsine africana	LOTUS Database	35616633
Quillaja saponaria	LOTUS Database	35616633
Spiraea canescens	LOTUS Database	35616633
Stephania longa	LOTUS Database	35616633
Strobilanthes cusia	LOTUS Database	35616633
Verbena brasiliensis	LOTUS Database	35616633
Walsura robusta	LOTUS Database	35616633
Zanthoxylum petiolare	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as lignan glycosides. These are aromatic polycyclic compounds containing a carbohydrate component glycosidically linked to a lignan moiety. They include 1-aryltetralin lactones.

Kingdom

Organic compounds

Super Class

Lignans, neolignans and related compounds

Class

Lignan glycosides

Sub Class

Not Available

Direct Parent

Lignan glycosides

Alternative Parents

Substituents

Lignan glycoside
1-aryltetralin lignan
Hexose monosaccharide
Glycosyl compound
O-glycosyl compound
Methoxyphenol
M-dimethoxybenzene
Dimethoxybenzene
Tetralin
Anisole
Phenoxy compound
Methoxybenzene
Phenol ether
Phenol
Alkyl aryl ether
Oxane
Benzenoid
Monosaccharide
Monocyclic benzene moiety
Secondary alcohol
Polyol
Acetal
Oxacycle
Organoheterocyclic compound
Ether
Organooxygen compound
Alcohol
Primary alcohol
Organic oxygen compound
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

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	0.22	ALOGPS
logP	-0.31	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Acidic)	9.24	ChemAxon
pKa (Strongest Basic)	-2.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	13	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	196.99 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	143.21 m³·mol⁻¹	ChemAxon
Polarizability	59.58 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

HMDB0038922

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB021035

KNApSAcK ID

Not Available

Chemspider ID

23550800

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

14521083

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for (-)-Lyoniresinol 9'-O-glucoside (NP0138542)

MOL for NP0138542 ((-)-Lyoniresinol 9'-O-glucoside)

3D MOL for NP0138542 ((-)-Lyoniresinol 9'-O-glucoside)

3D SDF for NP0138542 ((-)-Lyoniresinol 9'-O-glucoside)

3D-SDF for NP0138542 ((-)-Lyoniresinol 9'-O-glucoside)

PDB for NP0138542 ((-)-Lyoniresinol 9'-O-glucoside)

3D PDB for NP0138542 ((-)-Lyoniresinol 9'-O-glucoside)

SMILES for NP0138542 ((-)-Lyoniresinol 9'-O-glucoside)

INCHI for NP0138542 ((-)-Lyoniresinol 9'-O-glucoside)

Structure for NP0138542 ((-)-Lyoniresinol 9'-O-glucoside)

3D Structure for NP0138542 ((-)-Lyoniresinol 9'-O-glucoside)