NP-MRD: Showing NP-Card for 4-[(2s,3s)-3-(3,5-dihydroxyphenyl)-5-[(1e)-2-(3,5-dihydroxyphenyl)ethenyl]-6-hydroxy-2,3-dihydro-1-benzofuran-2-yl]benzene-1,2-diol (NP0253107)

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Record Information

Version

2.0

Created at

2022-09-07 16:52:55 UTC

Updated at

2022-09-07 16:52:55 UTC

NP-MRD ID

NP0253107

Secondary Accession Numbers

None

Natural Product Identification

Common Name

4-[(2s,3s)-3-(3,5-dihydroxyphenyl)-5-[(1e)-2-(3,5-dihydroxyphenyl)ethenyl]-6-hydroxy-2,3-dihydro-1-benzofuran-2-yl]benzene-1,2-diol

Description

4-[(2S,3S)-3-(3,5-dihydroxyphenyl)-5-[(E)-2-(3,5-dihydroxyphenyl)ethenyl]-6-hydroxy-2,3-dihydro-1-benzofuran-2-yl]benzene-1,2-diol belongs to the class of organic compounds known as 2-arylbenzofuran flavonoids. These are phenylpropanoids containing the 2-phenylbenzofuran moiety. 4-[(2s,3s)-3-(3,5-dihydroxyphenyl)-5-[(1e)-2-(3,5-dihydroxyphenyl)ethenyl]-6-hydroxy-2,3-dihydro-1-benzofuran-2-yl]benzene-1,2-diol is found in Morus macroura. Based on a literature review very few articles have been published on 4-[(2S,3S)-3-(3,5-dihydroxyphenyl)-5-[(E)-2-(3,5-dihydroxyphenyl)ethenyl]-6-hydroxy-2,3-dihydro-1-benzofuran-2-yl]benzene-1,2-diol.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309072218522D          

 36 40  0  0  1  0            999 V2000
    6.3569    1.1104    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    4.2135   -0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2135    0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4990    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv1652309072218522D          

 36 40  0  0  1  0            999 V2000
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M  END
> <DATABASE_ID>
NP0253107

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1=CC(\C=C\C2=CC3=C(O[C@@H]([C@H]3C3=CC(O)=CC(O)=C3)C3=CC=C(O)C(O)=C3)C=C2O)=CC(O)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C28H22O8/c29-18-5-14(6-19(30)11-18)1-2-15-9-22-26(13-24(15)34)36-28(16-3-4-23(33)25(35)10-16)27(22)17-7-20(31)12-21(32)8-17/h1-13,27-35H/b2-1+/t27-,28+/m0/s1

> <INCHI_KEY>
QOBRIVOFSCJJOV-LPGNHZEISA-N

> <FORMULA>
C28H22O8

> <MOLECULAR_WEIGHT>
486.476

> <EXACT_MASS>
486.131467668

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
58

> <JCHEM_AVERAGE_POLARIZABILITY>
50.50916724507461

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
4-[(2S,3S)-3-(3,5-dihydroxyphenyl)-5-[(E)-2-(3,5-dihydroxyphenyl)ethenyl]-6-hydroxy-2,3-dihydro-1-benzofuran-2-yl]benzene-1,2-diol

> <JCHEM_LOGP>
5.3533638266666665

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.888378873906037

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.40000410494287

> <JCHEM_PKA_STRONGEST_BASIC>
-4.899576087725846

> <JCHEM_POLAR_SURFACE_AREA>
150.84

> <JCHEM_REFRACTIVITY>
134.0013

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
4-[(2S,3S)-3-(3,5-dihydroxyphenyl)-5-[(E)-2-(3,5-dihydroxyphenyl)ethenyl]-6-hydroxy-2,3-dihydro-1-benzofuran-2-yl]benzene-1,2-diol

> <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  O   UNK     0      11.866   2.073   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      10.533   1.303   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      10.533  -0.237   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.199  -1.007   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       9.199  -2.547   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       7.865  -0.237   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.865   1.303   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.531   2.073   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.198   1.303   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.864   2.073   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.530   1.303   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.197   2.073   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.197   3.613   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.530   4.383   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.864   3.613   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       5.198   4.383   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0      -0.268   4.089   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      -1.173   2.843   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -2.713   2.843   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -3.483   1.509   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -5.023   1.509   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -5.793   2.843   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      -7.333   2.843   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      -5.023   4.177   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      -5.793   5.510   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      -3.483   4.177   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -0.268   1.597   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -0.744   0.132   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       0.287  -1.012   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -0.189  -2.477   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       0.841  -3.621   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      -1.696  -2.797   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -2.726  -1.652   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      -4.232  -1.973   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0      -2.250  -0.188   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       9.199   2.073   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   36                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6    8   36                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   15                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   27                                                  
CONECT   13   12   14   17                                                  
CONECT   14   13   15                                                       
CONECT   15   14   10   16                                                  
CONECT   16   15                                                            
CONECT   17   13   18                                                       
CONECT   18   17   19   27                                                  
CONECT   19   18   20   26                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   19                                                       
CONECT   27   18   12   28                                                  
CONECT   28   27   29   35                                                  
CONECT   29   28   30                                                       
CONECT   30   29   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30   33                                                       
CONECT   33   32   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33   28                                                       
CONECT   36    7    2                                                       
MASTER        0    0    0    0    0    0    0    0   36    0   80    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₈H₂₂O₈

Average Mass

486.4760 Da

Monoisotopic Mass

486.13147 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

OC1=CC(\C=C\C2=CC3=C(O[C@@H]([C@H]3C3=CC(O)=CC(O)=C3)C3=CC=C(O)C(O)=C3)C=C2O)=CC(O)=C1

InChI Identifier

InChI=1S/C28H22O8/c29-18-5-14(6-19(30)11-18)1-2-15-9-22-26(13-24(15)34)36-28(16-3-4-23(33)25(35)10-16)27(22)17-7-20(31)12-21(32)8-17/h1-13,27-35H/b2-1+/t27-,28+/m0/s1

InChI Key

QOBRIVOFSCJJOV-LPGNHZEISA-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
Morus laevigata	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
Linear 1,7-diphenylheptane skeleton
Neolignan skeleton
1-phenylcoumaran
Stilbene
Coumaran
Benzofuran
Catechol
Styrene
Resorcinol
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Phenol
Monocyclic benzene moiety
Benzenoid
Oxacycle
Organoheterocyclic compound
Ether
Organic oxygen compound
Hydrocarbon derivative
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

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

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

163185967

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 4-[(2s,3s)-3-(3,5-dihydroxyphenyl)-5-[(1e)-2-(3,5-dihydroxyphenyl)ethenyl]-6-hydroxy-2,3-dihydro-1-benzofuran-2-yl]benzene-1,2-diol (NP0253107)

MOL for NP0253107 (4-[(2s,3s)-3-(3,5-dihydroxyphenyl)-5-[(1e)-2-(3,5-dihydroxyphenyl)ethenyl]-6-hydroxy-2,3-dihydro-1-benzofuran-2-yl]benzene-1,2-diol)

3D MOL for NP0253107 (4-[(2s,3s)-3-(3,5-dihydroxyphenyl)-5-[(1e)-2-(3,5-dihydroxyphenyl)ethenyl]-6-hydroxy-2,3-dihydro-1-benzofuran-2-yl]benzene-1,2-diol)

3D SDF for NP0253107 (4-[(2s,3s)-3-(3,5-dihydroxyphenyl)-5-[(1e)-2-(3,5-dihydroxyphenyl)ethenyl]-6-hydroxy-2,3-dihydro-1-benzofuran-2-yl]benzene-1,2-diol)

3D-SDF for NP0253107 (4-[(2s,3s)-3-(3,5-dihydroxyphenyl)-5-[(1e)-2-(3,5-dihydroxyphenyl)ethenyl]-6-hydroxy-2,3-dihydro-1-benzofuran-2-yl]benzene-1,2-diol)

PDB for NP0253107 (4-[(2s,3s)-3-(3,5-dihydroxyphenyl)-5-[(1e)-2-(3,5-dihydroxyphenyl)ethenyl]-6-hydroxy-2,3-dihydro-1-benzofuran-2-yl]benzene-1,2-diol)

3D PDB for NP0253107 (4-[(2s,3s)-3-(3,5-dihydroxyphenyl)-5-[(1e)-2-(3,5-dihydroxyphenyl)ethenyl]-6-hydroxy-2,3-dihydro-1-benzofuran-2-yl]benzene-1,2-diol)

SMILES for NP0253107 (4-[(2s,3s)-3-(3,5-dihydroxyphenyl)-5-[(1e)-2-(3,5-dihydroxyphenyl)ethenyl]-6-hydroxy-2,3-dihydro-1-benzofuran-2-yl]benzene-1,2-diol)

INCHI for NP0253107 (4-[(2s,3s)-3-(3,5-dihydroxyphenyl)-5-[(1e)-2-(3,5-dihydroxyphenyl)ethenyl]-6-hydroxy-2,3-dihydro-1-benzofuran-2-yl]benzene-1,2-diol)

Structure for NP0253107 (4-[(2s,3s)-3-(3,5-dihydroxyphenyl)-5-[(1e)-2-(3,5-dihydroxyphenyl)ethenyl]-6-hydroxy-2,3-dihydro-1-benzofuran-2-yl]benzene-1,2-diol)

3D Structure for NP0253107 (4-[(2s,3s)-3-(3,5-dihydroxyphenyl)-5-[(1e)-2-(3,5-dihydroxyphenyl)ethenyl]-6-hydroxy-2,3-dihydro-1-benzofuran-2-yl]benzene-1,2-diol)