NP-MRD: Showing NP-Card for 2-{4-hydroxy-2,3-bis[(4-hydroxy-3-methoxyphenyl)methyl]butoxy}-6-(hydroxymethyl)oxane-3,4,5-triol (NP0269599)

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Record Information

Version

2.0

Created at

2022-09-08 15:09:24 UTC

Updated at

2022-09-08 15:09:25 UTC

NP-MRD ID

NP0269599

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2-{4-hydroxy-2,3-bis[(4-hydroxy-3-methoxyphenyl)methyl]butoxy}-6-(hydroxymethyl)oxane-3,4,5-triol

Description

(8R,8'R)-Secoisolariciresinol 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 (8R,8'R)-Secoisolariciresinol 9-glucoside is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, (8R,8'R)-Secoisolariciresinol 9-glucoside has been detected, but not quantified in, alcoholic beverages. 2-{4-hydroxy-2,3-bis[(4-hydroxy-3-methoxyphenyl)methyl]butoxy}-6-(hydroxymethyl)oxane-3,4,5-triol is found in Berchemia racemosa, Picea abies, Picea glauca, Pinus sylvestris and Tinospora cordifolia. This could make (8R,8'r)-secoisolariciresinol 9-glucoside a potential biomarker for the consumption of these foods.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 05061309332D          

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M  END

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  Mrv0541 05061309332D          

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 18  5  1  0  0  0  0
 19  6  1  0  0  0  0
 20  9  1  0  0  0  0
 20 18  2  0  0  0  0
 21 10  1  0  0  0  0
 21 19  2  0  0  0  0
 22 12  1  0  0  0  0
 23 22  1  0  0  0  0
 24 23  1  0  0  0  0
 25 24  1  0  0  0  0
 26 25  1  0  0  0  0
 27 11  1  0  0  0  0
 28 12  1  0  0  0  0
 29 18  1  0  0  0  0
 30 19  1  0  0  0  0
 31 23  1  0  0  0  0
 32 24  1  0  0  0  0
 33 25  1  0  0  0  0
 34  1  1  0  0  0  0
 34 20  1  0  0  0  0
 35  2  1  0  0  0  0
 35 21  1  0  0  0  0
 36 13  1  0  0  0  0
 36 26  1  0  0  0  0
 37 22  1  0  0  0  0
 37 26  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0269599

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C(O)C=CC(CC(CO)C(COC2OC(CO)C(O)C(O)C2O)CC2=CC(OC)=C(O)C=C2)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C26H36O11/c1-34-20-9-14(3-5-18(20)29)7-16(11-27)17(8-15-4-6-19(30)21(10-15)35-2)13-36-26-25(33)24(32)23(31)22(12-28)37-26/h3-6,9-10,16-17,22-33H,7-8,11-13H2,1-2H3

> <INCHI_KEY>
DRLPXFRWJUZTMG-UHFFFAOYSA-N

> <FORMULA>
C26H36O11

> <MOLECULAR_WEIGHT>
524.5574

> <EXACT_MASS>
524.225761994

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_AVERAGE_POLARIZABILITY>
53.53140885322083

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-{4-hydroxy-2,3-bis[(4-hydroxy-3-methoxyphenyl)methyl]butoxy}-6-(hydroxymethyl)oxane-3,4,5-triol

> <ALOGPS_LOGP>
0.77

> <JCHEM_LOGP>
0.5620254370000006

> <ALOGPS_LOGS>
-3.23

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
10.557964252226196

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.960726335174472

> <JCHEM_PKA_STRONGEST_BASIC>
-2.603215875922923

> <JCHEM_POLAR_SURFACE_AREA>
178.52999999999997

> <JCHEM_REFRACTIVITY>
131.70029999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
12

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.07e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-{4-hydroxy-2,3-bis[(4-hydroxy-3-methoxyphenyl)methyl]butoxy}-6-(hydroxymethyl)oxane-3,4,5-triol

> <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      -0.825   0.825   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      14.575   6.160   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.025   4.826   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      10.725   2.159   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.485   4.826   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      12.265   2.159   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.335   3.493   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.415   3.493   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.025   2.159   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      10.725   4.826   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.335   6.160   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      14.575   8.827   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.415   6.160   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.795   3.493   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       9.955   3.493   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.105   4.826   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       7.645   4.826   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.715   3.493   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      13.035   3.493   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.485   2.159   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      12.265   4.826   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      13.035   8.827   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      12.265  10.161   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      10.725  10.161   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       9.955   8.827   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      10.725   7.494   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       6.105   7.494   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0      15.345  10.161   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0      -0.825   3.493   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0      14.575   3.493   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0      13.035  11.495   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0       9.955  11.495   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0       8.415   8.827   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0       0.715   0.825   0.000  0.00  0.00           O+0
HETATM   35  O   UNK     0      13.035   6.160   0.000  0.00  0.00           O+0
HETATM   36  O   UNK     0       9.955   6.160   0.000  0.00  0.00           O+0
HETATM   37  O   UNK     0      12.265   7.494   0.000  0.00  0.00           O+0
CONECT    1   34                                                            
CONECT    2   35                                                            
CONECT    3    5   14                                                       
CONECT    4    6   15                                                       
CONECT    5    3   18                                                       
CONECT    6    4   19                                                       
CONECT    7   14   16                                                       
CONECT    8   15   17                                                       
CONECT    9   14   20                                                       
CONECT   10   15   21                                                       
CONECT   11   16   27                                                       
CONECT   12   22   28                                                       
CONECT   13   17   36                                                       
CONECT   14    3    7    9                                                  
CONECT   15    4    8   10                                                  
CONECT   16    7   11   17                                                  
CONECT   17    8   13   16                                                  
CONECT   18    5   20   29                                                  
CONECT   19    6   21   30                                                  
CONECT   20    9   18   34                                                  
CONECT   21   10   19   35                                                  
CONECT   22   12   23   37                                                  
CONECT   23   22   24   31                                                  
CONECT   24   23   25   32                                                  
CONECT   25   24   26   33                                                  
CONECT   26   25   36   37                                                  
CONECT   27   11                                                            
CONECT   28   12                                                            
CONECT   29   18                                                            
CONECT   30   19                                                            
CONECT   31   23                                                            
CONECT   32   24                                                            
CONECT   33   25                                                            
CONECT   34    1   20                                                       
CONECT   35    2   21                                                       
CONECT   36   13   26                                                       
CONECT   37   22   26                                                       
MASTER        0    0    0    0    0    0    0    0   37    0   78    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₆H₃₆O₁₁

Average Mass

524.5574 Da

Monoisotopic Mass

524.22576 Da

IUPAC Name

2-{4-hydroxy-2,3-bis[(4-hydroxy-3-methoxyphenyl)methyl]butoxy}-6-(hydroxymethyl)oxane-3,4,5-triol

Traditional Name

2-{4-hydroxy-2,3-bis[(4-hydroxy-3-methoxyphenyl)methyl]butoxy}-6-(hydroxymethyl)oxane-3,4,5-triol

CAS Registry Number

Not Available

SMILES

COC1=C(O)C=CC(CC(CO)C(COC2OC(CO)C(O)C(O)C2O)CC2=CC(OC)=C(O)C=C2)=C1

InChI Identifier

InChI=1S/C26H36O11/c1-34-20-9-14(3-5-18(20)29)7-16(11-27)17(8-15-4-6-19(30)21(10-15)35-2)13-36-26-25(33)24(32)23(31)22(12-28)37-26/h3-6,9-10,16-17,22-33H,7-8,11-13H2,1-2H3

InChI Key

DRLPXFRWJUZTMG-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
Berchemia racemosa	LOTUS Database	35616633
Picea abies	LOTUS Database	35616633
Picea glauca	LOTUS Database	35616633
Pinus sylvestris	LOTUS Database	35616633
Tinospora cordifolia	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
Dibenzylbutane lignan skeleton
Fatty acyl glycoside
Fatty acyl glycoside of mono- or disaccharide
Alkyl glycoside
Hexose monosaccharide
Glycosyl compound
O-glycosyl compound
Methoxyphenol
Phenoxy compound
Anisole
Methoxybenzene
Phenol ether
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Phenol
Monocyclic benzene moiety
Fatty acyl
Benzenoid
Oxane
Monosaccharide
Secondary alcohol
Organoheterocyclic compound
Ether
Acetal
Polyol
Oxacycle
Organic oxygen compound
Alcohol
Primary alcohol
Hydrocarbon derivative
Organooxygen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic 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	0.77	ALOGPS
logP	0.56	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	9.96	ChemAxon
pKa (Strongest Basic)	-2.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	178.53 Å²	ChemAxon
Rotatable Bond Count	12	ChemAxon
Refractivity	131.7 m³·mol⁻¹	ChemAxon
Polarizability	53.53 Å³	ChemAxon
Number of Rings	3	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

HMDB0037083

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB016071

KNApSAcK ID

Not Available

Chemspider ID

22370029

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

14704357

PDB ID

Not Available

ChEBI ID

139406

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 2-{4-hydroxy-2,3-bis[(4-hydroxy-3-methoxyphenyl)methyl]butoxy}-6-(hydroxymethyl)oxane-3,4,5-triol (NP0269599)

MOL for NP0269599 (2-{4-hydroxy-2,3-bis[(4-hydroxy-3-methoxyphenyl)methyl]butoxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

3D MOL for NP0269599 (2-{4-hydroxy-2,3-bis[(4-hydroxy-3-methoxyphenyl)methyl]butoxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

3D SDF for NP0269599 (2-{4-hydroxy-2,3-bis[(4-hydroxy-3-methoxyphenyl)methyl]butoxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

3D-SDF for NP0269599 (2-{4-hydroxy-2,3-bis[(4-hydroxy-3-methoxyphenyl)methyl]butoxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

PDB for NP0269599 (2-{4-hydroxy-2,3-bis[(4-hydroxy-3-methoxyphenyl)methyl]butoxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

3D PDB for NP0269599 (2-{4-hydroxy-2,3-bis[(4-hydroxy-3-methoxyphenyl)methyl]butoxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

SMILES for NP0269599 (2-{4-hydroxy-2,3-bis[(4-hydroxy-3-methoxyphenyl)methyl]butoxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

INCHI for NP0269599 (2-{4-hydroxy-2,3-bis[(4-hydroxy-3-methoxyphenyl)methyl]butoxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

Structure for NP0269599 (2-{4-hydroxy-2,3-bis[(4-hydroxy-3-methoxyphenyl)methyl]butoxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

3D Structure for NP0269599 (2-{4-hydroxy-2,3-bis[(4-hydroxy-3-methoxyphenyl)methyl]butoxy}-6-(hydroxymethyl)oxane-3,4,5-triol)