NP-MRD: Showing NP-Card for (2r,3r,4s,5s,6r)-2-{3-[2-(2h-1,3-benzodioxol-5-yl)-7-methoxy-1-benzofuran-5-yl]propoxy}-6-(hydroxymethyl)oxane-3,4,5-triol (NP0256463)

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Record Information

Version

2.0

Created at

2022-09-07 21:18:05 UTC

Updated at

2022-09-07 21:18:05 UTC

NP-MRD ID

NP0256463

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2r,3r,4s,5s,6r)-2-{3-[2-(2h-1,3-benzodioxol-5-yl)-7-methoxy-1-benzofuran-5-yl]propoxy}-6-(hydroxymethyl)oxane-3,4,5-triol

Description

Egonol beta-D-glucoside belongs to the class of organic compounds known as 2-arylbenzofuran flavonoids. These are phenylpropanoids containing the 2-phenylbenzofuran moiety. Egonol beta-D-glucoside is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. (2r,3r,4s,5s,6r)-2-{3-[2-(2h-1,3-benzodioxol-5-yl)-7-methoxy-1-benzofuran-5-yl]propoxy}-6-(hydroxymethyl)oxane-3,4,5-triol is found in Laetiporus sulphureus and Styrax ferrugineus. (2r,3r,4s,5s,6r)-2-{3-[2-(2h-1,3-benzodioxol-5-yl)-7-methoxy-1-benzofuran-5-yl]propoxy}-6-(hydroxymethyl)oxane-3,4,5-triol was first documented in 2001 (PMID: 11253926). Based on a literature review a small amount of articles have been published on egonol beta-D-glucoside (PMID: 16206040) (PMID: 15577246) (PMID: 17335993) (PMID: 20607490).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309072223182D          

 35 39  0  0  1  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652309072223182D          

 35 39  0  0  1  0            999 V2000
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M  END
> <DATABASE_ID>
NP0256463

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C2OC(=CC2=CC(CCCO[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)=C1)C1=CC=C2OCOC2=C1

> <INCHI_IDENTIFIER>
InChI=1S/C25H28O10/c1-30-19-8-13(3-2-6-31-25-23(29)22(28)21(27)20(11-26)35-25)7-15-10-17(34-24(15)19)14-4-5-16-18(9-14)33-12-32-16/h4-5,7-10,20-23,25-29H,2-3,6,11-12H2,1H3/t20-,21-,22+,23-,25-/m1/s1

> <INCHI_KEY>
RAMYDZNQLYKTGB-MXCHMSEPSA-N

> <FORMULA>
C25H28O10

> <MOLECULAR_WEIGHT>
488.489

> <EXACT_MASS>
488.168247102

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
63

> <JCHEM_AVERAGE_POLARIZABILITY>
51.980960676420786

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R,3R,4S,5S,6R)-2-{3-[2-(2H-1,3-benzodioxol-5-yl)-7-methoxy-1-benzofuran-5-yl]propoxy}-6-(hydroxymethyl)oxane-3,4,5-triol

> <JCHEM_LOGP>
1.360202361333334

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.200256634304523

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.21098727857011

> <JCHEM_PKA_STRONGEST_BASIC>
-2.922511444783924

> <JCHEM_POLAR_SURFACE_AREA>
140.21000000000004

> <JCHEM_REFRACTIVITY>
120.72810000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(2R,3R,4S,5S,6R)-2-{3-[2-(2H-1,3-benzodioxol-5-yl)-7-methoxy-1-benzofuran-5-yl]propoxy}-6-(hydroxymethyl)oxane-3,4,5-triol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 07-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-SEP-22         0                                  
HETATM    1  C   UNK     0       2.393   0.230   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       3.727  -0.540   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       3.727  -2.080   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.061  -2.850   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.061  -4.390   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.395  -5.160   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.728  -4.390   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.062  -5.160   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      10.396  -4.390   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      11.729  -5.160   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      13.063  -4.390   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      14.397  -5.160   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      15.730  -4.390   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      17.064  -5.160   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      14.397  -6.700   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      15.730  -7.470   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      13.063  -7.470   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      13.063  -9.010   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      11.729  -6.700   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      10.396  -7.470   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       3.727  -5.160   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       2.393  -4.390   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       0.929  -4.866   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       0.024  -3.620   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -1.516  -3.620   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -2.286  -4.954   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -3.826  -4.954   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -4.596  -3.620   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -3.826  -2.286   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -2.286  -2.286   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      -4.857  -1.142   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      -6.264  -1.768   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      -6.103  -3.300   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0       0.929  -2.374   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0       2.393  -2.850   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   35                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   21                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   19                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   15                                                  
CONECT   13   12   14                                                       
CONECT   14   13                                                            
CONECT   15   12   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   10   20                                                  
CONECT   20   19                                                            
CONECT   21    5   22                                                       
CONECT   22   21   23   35                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25   34                                                  
CONECT   25   24   26   30                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29   33                                                  
CONECT   29   28   30   31                                                  
CONECT   30   29   25                                                       
CONECT   31   29   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   28                                                       
CONECT   34   24   35                                                       
CONECT   35   34    3   22                                                  
MASTER        0    0    0    0    0    0    0    0   35    0   78    0
END

View in JSmol

Synonyms

Value	Source
Egonol glucoside	ChEBI
Egonol b-D-glucoside	Generator
Egonol β-D-glucoside	Generator

Chemical Formula

C₂₅H₂₈O₁₀

Average Mass

488.4890 Da

Monoisotopic Mass

488.16825 Da

IUPAC Name

(2R,3R,4S,5S,6R)-2-{3-[2-(2H-1,3-benzodioxol-5-yl)-7-methoxy-1-benzofuran-5-yl]propoxy}-6-(hydroxymethyl)oxane-3,4,5-triol

Traditional Name

(2R,3R,4S,5S,6R)-2-{3-[2-(2H-1,3-benzodioxol-5-yl)-7-methoxy-1-benzofuran-5-yl]propoxy}-6-(hydroxymethyl)oxane-3,4,5-triol

CAS Registry Number

Not Available

SMILES

COC1=C2OC(=CC2=CC(CCCO[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)=C1)C1=CC=C2OCOC2=C1

InChI Identifier

InChI=1S/C25H28O10/c1-30-19-8-13(3-2-6-31-25-23(29)22(28)21(27)20(11-26)35-25)7-15-10-17(34-24(15)19)14-4-5-16-18(9-14)33-12-32-16/h4-5,7-10,20-23,25-29H,2-3,6,11-12H2,1H3/t20-,21-,22+,23-,25-/m1/s1

InChI Key

RAMYDZNQLYKTGB-MXCHMSEPSA-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
Laetiporus sulphureus	LOTUS Database	35616633
Styrax ferrugineus	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 2-arylbenzofuran flavonoids. These are phenylpropanoids containing the 2-phenylbenzofuran moiety.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

2-arylbenzofuran flavonoids

Sub Class

Not Available

Direct Parent

2-arylbenzofuran flavonoids

Alternative Parents

Substituents

2-arylbenzofuran flavonoid
Lignan glycoside
Neolignan skeleton
Fatty acyl glycoside
Fatty acyl glycoside of mono- or disaccharide
Alkyl glycoside
Hexose monosaccharide
Glycosyl compound
O-glycosyl compound
Benzodioxole
Benzofuran
Anisole
Alkyl aryl ether
Oxane
Monosaccharide
Benzenoid
Fatty acyl
Heteroaromatic compound
Furan
Secondary alcohol
Polyol
Ether
Acetal
Oxacycle
Organoheterocyclic compound
Primary alcohol
Hydrocarbon derivative
Alcohol
Organic oxygen compound
Organooxygen compound
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	1.36	ChemAxon
pKa (Strongest Acidic)	12.21	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	140.21 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	120.73 m³·mol⁻¹	ChemAxon
Polarizability	51.98 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00031759

Chemspider ID

425434

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

485187

PDB ID

Not Available

ChEBI ID

134480

Good Scents ID

Not Available

References

General References

Li QL, Li BG, Qi HY, Gao XP, Zhang GL: Four new benzofurans from seeds of Styrax perkinsiae. Planta Med. 2005 Sep;71(9):847-51. doi: 10.1055/s-2005-871226. [PubMed:16206040 ]
Yoshikawa K, Bando S, Arihara S, Matsumura E, Katayama S: A benzofuran glycoside and an acetylenic acid from the fungus Laetiporus sulphureus var. miniatus. Chem Pharm Bull (Tokyo). 2001 Mar;49(3):327-9. doi: 10.1248/cpb.49.327. [PubMed:11253926 ]
Kim MR, Moon HI, Chung JH, Moon YH, Hahm KS, Woo ER: Matrix metalloproteinase-1 inhibitor from the stem bark of Styrax japonica S. et Z. Chem Pharm Bull (Tokyo). 2004 Dec;52(12):1466-9. doi: 10.1248/cpb.52.1466. [PubMed:15577246 ]
Luo Y, He Z, Li H: 2-aryl benzofurans and their derivatives from seeds of Styrax macranthus. Fitoterapia. 2007 Apr;78(3):211-4. doi: 10.1016/j.fitote.2007.01.001. Epub 2007 Feb 3. [PubMed:17335993 ]
Lee DG, Jin Q, Jin HG, Shin JE, Choi EJ, Woo ER: Isolation of virus-cell fusion inhibitory components from the stem bark of Styrax japonica S. et Z. Arch Pharm Res. 2010 Jun;33(6):863-6. doi: 10.1007/s12272-010-0608-4. Epub 2010 Jul 6. [PubMed:20607490 ]
LOTUS database [Link]

Showing NP-Card for (2r,3r,4s,5s,6r)-2-{3-[2-(2h-1,3-benzodioxol-5-yl)-7-methoxy-1-benzofuran-5-yl]propoxy}-6-(hydroxymethyl)oxane-3,4,5-triol (NP0256463)

MOL for NP0256463 ((2r,3r,4s,5s,6r)-2-{3-[2-(2h-1,3-benzodioxol-5-yl)-7-methoxy-1-benzofuran-5-yl]propoxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

3D MOL for NP0256463 ((2r,3r,4s,5s,6r)-2-{3-[2-(2h-1,3-benzodioxol-5-yl)-7-methoxy-1-benzofuran-5-yl]propoxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

3D SDF for NP0256463 ((2r,3r,4s,5s,6r)-2-{3-[2-(2h-1,3-benzodioxol-5-yl)-7-methoxy-1-benzofuran-5-yl]propoxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

3D-SDF for NP0256463 ((2r,3r,4s,5s,6r)-2-{3-[2-(2h-1,3-benzodioxol-5-yl)-7-methoxy-1-benzofuran-5-yl]propoxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

PDB for NP0256463 ((2r,3r,4s,5s,6r)-2-{3-[2-(2h-1,3-benzodioxol-5-yl)-7-methoxy-1-benzofuran-5-yl]propoxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

3D PDB for NP0256463 ((2r,3r,4s,5s,6r)-2-{3-[2-(2h-1,3-benzodioxol-5-yl)-7-methoxy-1-benzofuran-5-yl]propoxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

SMILES for NP0256463 ((2r,3r,4s,5s,6r)-2-{3-[2-(2h-1,3-benzodioxol-5-yl)-7-methoxy-1-benzofuran-5-yl]propoxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

INCHI for NP0256463 ((2r,3r,4s,5s,6r)-2-{3-[2-(2h-1,3-benzodioxol-5-yl)-7-methoxy-1-benzofuran-5-yl]propoxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

Structure for NP0256463 ((2r,3r,4s,5s,6r)-2-{3-[2-(2h-1,3-benzodioxol-5-yl)-7-methoxy-1-benzofuran-5-yl]propoxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

3D Structure for NP0256463 ((2r,3r,4s,5s,6r)-2-{3-[2-(2h-1,3-benzodioxol-5-yl)-7-methoxy-1-benzofuran-5-yl]propoxy}-6-(hydroxymethyl)oxane-3,4,5-triol)