NP-MRD: Showing NP-Card for (2s,3r,4r,5r,6s)-2-{4-[(2s,3r)-3-(hydroxymethyl)-7-methoxy-5-[(1r,2s)-1,2,3-trihydroxypropyl]-2,3-dihydro-1-benzofuran-2-yl]-2-methoxyphenoxy}-6-methyloxane-3,4,5-triol (NP0258910)

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Record Information

Version

2.0

Created at

2022-09-08 00:35:41 UTC

Updated at

2022-09-08 00:35:41 UTC

NP-MRD ID

NP0258910

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2s,3r,4r,5r,6s)-2-{4-[(2s,3r)-3-(hydroxymethyl)-7-methoxy-5-[(1r,2s)-1,2,3-trihydroxypropyl]-2,3-dihydro-1-benzofuran-2-yl]-2-methoxyphenoxy}-6-methyloxane-3,4,5-triol

Description

CHEMBL562877 belongs to the class of organic compounds known as 2-arylbenzofuran flavonoids. These are phenylpropanoids containing the 2-phenylbenzofuran moiety. Based on a literature review very few articles have been published on CHEMBL562877.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309082202352D          

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M  END

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M  END


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  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
  9 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  6  0  0  0
 14 16  1  0  0  0  0
 16 17  1  1  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 13 20  1  0  0  0  0
 20 21  2  0  0  0  0
  8 21  1  0  0  0  0
 21 22  1  0  0  0  0
  6 22  1  0  0  0  0
 22 23  1  6  0  0  0
 23 24  1  0  0  0  0
  5 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
  3 27  1  0  0  0  0
 27 28  1  0  0  0  0
 29 28  1  1  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  6  0  0  0
 31 33  1  0  0  0  0
 33 34  1  1  0  0  0
 33 35  1  0  0  0  0
 35 36  1  6  0  0  0
 35 37  1  0  0  0  0
 29 37  1  0  0  0  0
 37 38  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0258910

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C2O[C@@H]([C@@H](CO)C2=CC(=C1)[C@@H](O)[C@@H](O)CO)C1=CC=C(O[C@@H]2O[C@@H](C)[C@H](O)[C@@H](O)[C@H]2O)C(OC)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C26H34O12/c1-11-20(30)22(32)23(33)26(36-11)37-17-5-4-12(7-18(17)34-2)24-15(9-27)14-6-13(21(31)16(29)10-28)8-19(35-3)25(14)38-24/h4-8,11,15-16,20-24,26-33H,9-10H2,1-3H3/t11-,15-,16-,20-,21+,22+,23+,24+,26-/m0/s1

> <INCHI_KEY>
NQHFIYPUIVKCLI-KNJWWJHHSA-N

> <FORMULA>
C26H34O12

> <MOLECULAR_WEIGHT>
538.546

> <EXACT_MASS>
538.205026535

> <JCHEM_ACCEPTOR_COUNT>
12

> <JCHEM_ATOM_COUNT>
72

> <JCHEM_AVERAGE_POLARIZABILITY>
54.51813891945069

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S,3R,4R,5R,6S)-2-{4-[(2S,3R)-3-(hydroxymethyl)-7-methoxy-5-[(1R,2S)-1,2,3-trihydroxypropyl]-2,3-dihydro-1-benzofuran-2-yl]-2-methoxyphenoxy}-6-methyloxane-3,4,5-triol

> <JCHEM_LOGP>
-1.2585314503333325

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.895062221136673

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.152736420392918

> <JCHEM_PKA_STRONGEST_BASIC>
-2.715987584586343

> <JCHEM_POLAR_SURFACE_AREA>
187.76

> <JCHEM_REFRACTIVITY>
130.66400000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(2S,3R,4R,5R,6S)-2-{4-[(2S,3R)-3-(hydroxymethyl)-7-methoxy-5-[(1R,2S)-1,2,3-trihydroxypropyl]-2,3-dihydro-1-benzofuran-2-yl]-2-methoxyphenoxy}-6-methyloxane-3,4,5-triol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 08-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   08-SEP-22         0                                  
HETATM    1  C   UNK     0      -2.630   2.698   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -3.400   1.365   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -2.630   0.031   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.090   0.031   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.320  -1.303   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.220  -1.303   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       2.126  -0.057   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       3.590  -0.533   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.924   0.237   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       4.924   1.777   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       6.258   2.547   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.258  -0.533   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.258  -2.073   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.591  -2.843   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       7.591  -4.383   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       8.925  -2.073   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       8.925  -0.533   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      10.259  -2.843   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      11.592  -2.073   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       4.924  -2.843   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       3.590  -2.073   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       2.126  -2.549   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       1.650  -4.013   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       0.143  -4.334   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      -1.090  -2.637   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -2.630  -2.637   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -3.400  -1.303   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      -4.940  -1.303   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      -5.710   0.031   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      -4.940   1.365   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      -5.710   2.698   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -4.940   4.032   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -7.250   2.698   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      -8.020   4.032   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0      -8.020   1.365   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0      -9.560   1.365   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0      -7.250   0.031   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0      -8.020  -1.303   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   27                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   25                                                  
CONECT    6    5    7   22                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   21                                                  
CONECT    9    8   10   12                                                  
CONECT   10    9   11                                                       
CONECT   11   10                                                            
CONECT   12    9   13                                                       
CONECT   13   12   14   20                                                  
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19                                                       
CONECT   19   18                                                            
CONECT   20   13   21                                                       
CONECT   21   20    8   22                                                  
CONECT   22   21    6   23                                                  
CONECT   23   22   24                                                       
CONECT   24   23                                                            
CONECT   25    5   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26    3   28                                                  
CONECT   28   27   29                                                       
CONECT   29   28   30   37                                                  
CONECT   30   29   31                                                       
CONECT   31   30   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33   36   37                                                  
CONECT   36   35                                                            
CONECT   37   35   29   38                                                  
CONECT   38   37                                                            
MASTER        0    0    0    0    0    0    0    0   38    0   82    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₆H₃₄O₁₂

Average Mass

538.5460 Da

Monoisotopic Mass

538.20503 Da

IUPAC Name

(2S,3R,4R,5R,6S)-2-{4-[(2S,3R)-3-(hydroxymethyl)-7-methoxy-5-[(1R,2S)-1,2,3-trihydroxypropyl]-2,3-dihydro-1-benzofuran-2-yl]-2-methoxyphenoxy}-6-methyloxane-3,4,5-triol

Traditional Name

(2S,3R,4R,5R,6S)-2-{4-[(2S,3R)-3-(hydroxymethyl)-7-methoxy-5-[(1R,2S)-1,2,3-trihydroxypropyl]-2,3-dihydro-1-benzofuran-2-yl]-2-methoxyphenoxy}-6-methyloxane-3,4,5-triol

CAS Registry Number

Not Available

SMILES

COC1=C2O[C@@H]([C@@H](CO)C2=CC(=C1)[C@@H](O)[C@@H](O)CO)C1=CC=C(O[C@@H]2O[C@@H](C)[C@H](O)[C@@H](O)[C@H]2O)C(OC)=C1

InChI Identifier

InChI=1S/C26H34O12/c1-11-20(30)22(32)23(33)26(36-11)37-17-5-4-12(7-18(17)34-2)24-15(9-27)14-6-13(21(31)16(29)10-28)8-19(35-3)25(14)38-24/h4-8,11,15-16,20-24,26-33H,9-10H2,1-3H3/t11-,15-,16-,20-,21+,22+,23+,24+,26-/m0/s1

InChI Key

NQHFIYPUIVKCLI-KNJWWJHHSA-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

Not Available

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
Norlignan skeleton
Neolignan skeleton
Phenolic glycoside
Fatty acyl glycoside of mono- or disaccharide
Fatty acyl glycoside
Hexose monosaccharide
Alkyl glycoside
O-glycosyl compound
Glycosyl compound
Coumaran
Benzofuran
Phenol ether
Methoxybenzene
Anisole
Phenoxy compound
Alkyl aryl ether
Benzenoid
Monocyclic benzene moiety
Oxane
Fatty acyl
Monosaccharide
Secondary alcohol
Acetal
Oxacycle
Organoheterocyclic compound
Ether
Polyol
Organic oxygen compound
Aromatic alcohol
Hydrocarbon derivative
Primary alcohol
Alcohol
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	-1.3	ChemAxon
pKa (Strongest Acidic)	12.15	ChemAxon
pKa (Strongest Basic)	-2.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	12	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	187.76 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	130.66 m³·mol⁻¹	ChemAxon
Polarizability	54.52 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

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

24628285

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

45272229

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2s,3r,4r,5r,6s)-2-{4-[(2s,3r)-3-(hydroxymethyl)-7-methoxy-5-[(1r,2s)-1,2,3-trihydroxypropyl]-2,3-dihydro-1-benzofuran-2-yl]-2-methoxyphenoxy}-6-methyloxane-3,4,5-triol (NP0258910)

MOL for NP0258910 ((2s,3r,4r,5r,6s)-2-{4-[(2s,3r)-3-(hydroxymethyl)-7-methoxy-5-[(1r,2s)-1,2,3-trihydroxypropyl]-2,3-dihydro-1-benzofuran-2-yl]-2-methoxyphenoxy}-6-methyloxane-3,4,5-triol)

3D MOL for NP0258910 ((2s,3r,4r,5r,6s)-2-{4-[(2s,3r)-3-(hydroxymethyl)-7-methoxy-5-[(1r,2s)-1,2,3-trihydroxypropyl]-2,3-dihydro-1-benzofuran-2-yl]-2-methoxyphenoxy}-6-methyloxane-3,4,5-triol)

3D SDF for NP0258910 ((2s,3r,4r,5r,6s)-2-{4-[(2s,3r)-3-(hydroxymethyl)-7-methoxy-5-[(1r,2s)-1,2,3-trihydroxypropyl]-2,3-dihydro-1-benzofuran-2-yl]-2-methoxyphenoxy}-6-methyloxane-3,4,5-triol)

3D-SDF for NP0258910 ((2s,3r,4r,5r,6s)-2-{4-[(2s,3r)-3-(hydroxymethyl)-7-methoxy-5-[(1r,2s)-1,2,3-trihydroxypropyl]-2,3-dihydro-1-benzofuran-2-yl]-2-methoxyphenoxy}-6-methyloxane-3,4,5-triol)

PDB for NP0258910 ((2s,3r,4r,5r,6s)-2-{4-[(2s,3r)-3-(hydroxymethyl)-7-methoxy-5-[(1r,2s)-1,2,3-trihydroxypropyl]-2,3-dihydro-1-benzofuran-2-yl]-2-methoxyphenoxy}-6-methyloxane-3,4,5-triol)

3D PDB for NP0258910 ((2s,3r,4r,5r,6s)-2-{4-[(2s,3r)-3-(hydroxymethyl)-7-methoxy-5-[(1r,2s)-1,2,3-trihydroxypropyl]-2,3-dihydro-1-benzofuran-2-yl]-2-methoxyphenoxy}-6-methyloxane-3,4,5-triol)

SMILES for NP0258910 ((2s,3r,4r,5r,6s)-2-{4-[(2s,3r)-3-(hydroxymethyl)-7-methoxy-5-[(1r,2s)-1,2,3-trihydroxypropyl]-2,3-dihydro-1-benzofuran-2-yl]-2-methoxyphenoxy}-6-methyloxane-3,4,5-triol)

INCHI for NP0258910 ((2s,3r,4r,5r,6s)-2-{4-[(2s,3r)-3-(hydroxymethyl)-7-methoxy-5-[(1r,2s)-1,2,3-trihydroxypropyl]-2,3-dihydro-1-benzofuran-2-yl]-2-methoxyphenoxy}-6-methyloxane-3,4,5-triol)

Structure for NP0258910 ((2s,3r,4r,5r,6s)-2-{4-[(2s,3r)-3-(hydroxymethyl)-7-methoxy-5-[(1r,2s)-1,2,3-trihydroxypropyl]-2,3-dihydro-1-benzofuran-2-yl]-2-methoxyphenoxy}-6-methyloxane-3,4,5-triol)

3D Structure for NP0258910 ((2s,3r,4r,5r,6s)-2-{4-[(2s,3r)-3-(hydroxymethyl)-7-methoxy-5-[(1r,2s)-1,2,3-trihydroxypropyl]-2,3-dihydro-1-benzofuran-2-yl]-2-methoxyphenoxy}-6-methyloxane-3,4,5-triol)