NP-MRD: Showing NP-Card for (-)-Gnetuhainin M (NP0332868)

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Record Information

Version

2.0

Created at

2024-05-01 15:49:01 UTC

Updated at

2025-05-24 00:05:38 UTC

NP-MRD ID

NP0332868

Natural Product DOI

https://doi.org/10.57994/2147

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(-)-Gnetuhainin M

Description

Based on a literature review very few articles have been published on Gnetoline E.

Structure

MOL SDF PDB SMILES InChI


  Mrv2104 01132318252D          

 53 60  0  0  1  0            999 V2000
    8.6414    4.7610    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8164    4.7610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4039    4.0465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5789    4.0465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4039    5.4755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5789    5.4755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1664    4.7610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3414    4.7610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9289    4.0465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1039    4.0465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6914    4.7610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8664    4.7610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4539    5.4755    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4539    4.0465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8664    3.3320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6914    3.3320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9464    2.5474    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.7310    2.2925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3441    2.8445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1287    2.5896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7418    3.1416    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3002    1.7826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6871    1.2306    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8587    0.4236    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9025    1.4855    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789    2.0625    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.2789    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7798    1.0799    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2949    0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
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    2.0769   -1.6527    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.3440   -2.1672    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7179   -1.2111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  1  2  1  0  0  0  0
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 33 34  1  0  0  0  0
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 39 40  1  0  0  0  0
 39 41  1  0  0  0  0
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 49 50  1  0  0  0  0
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 50 52  2  0  0  0  0
 45 52  1  0  0  0  0
 26 53  1  0  0  0  0
 15 53  1  0  0  0  0
M  END


  Mrv2104 01132318252D          

 53 60  0  0  1  0            999 V2000
    8.6414    4.7610    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8164    4.7610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4039    4.0465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5789    4.0465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4039    5.4755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5789    5.4755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1664    4.7610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3414    4.7610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9289    4.0465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.6914    4.7610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.6914    3.3320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9464    2.5474    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.7310    2.2925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3441    2.8445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    6.3002    1.7826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    5.8587    0.4236    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    3.2789    2.0625    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
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    1.7798    1.0799    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.3440   -2.1672    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7179   -1.2111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6115    2.5474    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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 26 53  1  0  0  0  0
 15 53  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0332868

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1=CC=C(\C=C\C2=CC(O)=CC3=C2[C@@H]([C@H](O3)C2=CC=C(O)C3=C2O[C@@H]([C@@H]3C2=CC(O)=CC(O)=C2)C2=CC=C(O)C=C2O)C2=CC(O)=CC(O)=C2)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C42H32O11/c43-24-5-2-20(3-6-24)1-4-21-11-30(49)19-35-36(21)37(22-12-26(45)16-27(46)13-22)41(52-35)32-9-10-33(50)39-38(23-14-28(47)17-29(48)15-23)40(53-42(32)39)31-8-7-25(44)18-34(31)51/h1-19,37-38,40-41,43-51H/b4-1+/t37-,38+,40+,41+/m0/s1

> <INCHI_KEY>
SBAYNGXEDJLMOG-MNBLLGGNSA-N

> <FORMULA>
C42H32O11

> <MOLECULAR_WEIGHT>
712.707

> <EXACT_MASS>
712.19446185

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_ATOM_COUNT>
85

> <JCHEM_AVERAGE_POLARIZABILITY>
73.5075205457626

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
9

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
5-[(2S,3S)-2-[(2S,3R)-2-(2,4-dihydroxyphenyl)-3-(3,5-dihydroxyphenyl)-4-hydroxy-2,3-dihydro-1-benzofuran-7-yl]-6-hydroxy-4-[(1E)-2-(4-hydroxyphenyl)ethenyl]-2,3-dihydro-1-benzofuran-3-yl]benzene-1,3-diol

> <JCHEM_LOGP>
7.911467410333334

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
8

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.841348495355977

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.426280501176429

> <JCHEM_PKA_STRONGEST_BASIC>
-5.5051456613883465

> <JCHEM_POLAR_SURFACE_AREA>
200.52999999999997

> <JCHEM_REFRACTIVITY>
196.58529999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
5-[(2S,3S)-2-[(2S,3R)-2-(2,4-dihydroxyphenyl)-3-(3,5-dihydroxyphenyl)-4-hydroxy-2,3-dihydro-1-benzofuran-7-yl]-6-hydroxy-4-[(1E)-2-(4-hydroxyphenyl)ethenyl]-2,3-dihydro-1-benzofuran-3-yl]benzene-1,3-diol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 13-JAN-23   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   13-JAN-23         0                                  
HETATM    1  O   UNK     0      16.131   8.887   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      14.591   8.887   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      13.821   7.553   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      12.281   7.553   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      13.821  10.221   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      12.281  10.221   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      11.511   8.887   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.971   8.887   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.201   7.553   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.661   7.553   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.891   8.887   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.351   8.887   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       4.581  10.221   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       4.581   7.553   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.351   6.220   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.891   6.220   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       7.367   4.755   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.831   4.279   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       9.976   5.310   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      11.440   4.834   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      12.585   5.864   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      11.760   3.328   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      10.616   2.297   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      10.936   0.791   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       9.151   2.773   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       6.121   3.850   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       6.121   2.310   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       7.454   1.540   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       7.454   0.000   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       6.121  -0.770   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       6.121  -2.310   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       4.787   0.000   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       4.787   1.540   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       3.322   2.016   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0       2.417   0.770   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       0.877   0.770   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       0.107  -0.564   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      -1.433  -0.564   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      -2.203   0.770   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0      -3.743   0.770   0.000  0.00  0.00           O+0
HETATM   41  C   UNK     0      -1.433   2.104   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0       0.107   2.104   0.000  0.00  0.00           C+0
HETATM   43  O   UNK     0       0.877   3.437   0.000  0.00  0.00           O+0
HETATM   44  C   UNK     0       3.322  -0.476   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0       2.846  -1.941   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0       3.877  -3.085   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0       3.401  -4.550   0.000  0.00  0.00           C+0
HETATM   48  O   UNK     0       4.432  -5.694   0.000  0.00  0.00           O+0
HETATM   49  C   UNK     0       1.895  -4.870   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0       0.864  -3.725   0.000  0.00  0.00           C+0
HETATM   51  O   UNK     0      -0.642  -4.046   0.000  0.00  0.00           O+0
HETATM   52  C   UNK     0       1.340  -2.261   0.000  0.00  0.00           C+0
HETATM   53  O   UNK     0       4.875   4.755   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    5                                                  
CONECT    3    2    4                                                       
CONECT    4    3    7                                                       
CONECT    5    2    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    4    8                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   16                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14   16   53                                                  
CONECT   16   15   10   17                                                  
CONECT   17   16   18   26                                                  
CONECT   18   17   19   25                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23                                                       
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   18                                                       
CONECT   26   17   27   53                                                  
CONECT   27   26   28   33                                                  
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30   33   44                                                  
CONECT   33   32   27   34                                                  
CONECT   34   33   35                                                       
CONECT   35   34   36   44                                                  
CONECT   36   35   37   42                                                  
CONECT   37   36   38                                                       
CONECT   38   37   39                                                       
CONECT   39   38   40   41                                                  
CONECT   40   39                                                            
CONECT   41   39   42                                                       
CONECT   42   41   36   43                                                  
CONECT   43   42                                                            
CONECT   44   35   32   45                                                  
CONECT   45   44   46   52                                                  
CONECT   46   45   47                                                       
CONECT   47   46   48   49                                                  
CONECT   48   47                                                            
CONECT   49   47   50                                                       
CONECT   50   49   51   52                                                  
CONECT   51   50                                                            
CONECT   52   50   45                                                       
CONECT   53   26   15                                                       
MASTER        0    0    0    0    0    0    0    0   53    0  120    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₄₂H₃₂O₁₁

Average Mass

712.7070 Da

Monoisotopic Mass

712.19446 Da

IUPAC Name

5-[(2S,3S)-2-[(2S,3R)-2-(2,4-dihydroxyphenyl)-3-(3,5-dihydroxyphenyl)-4-hydroxy-2,3-dihydro-1-benzofuran-7-yl]-6-hydroxy-4-[(1E)-2-(4-hydroxyphenyl)ethenyl]-2,3-dihydro-1-benzofuran-3-yl]benzene-1,3-diol

Traditional Name

CAS Registry Number

Not Available

SMILES

OC1=CC=C(\C=C\C2=CC(O)=CC3=C2[C@@H]([C@H](O3)C2=CC=C(O)C3=C2O[C@@H]([C@@H]3C2=CC(O)=CC(O)=C2)C2=CC=C(O)C=C2O)C2=CC(O)=CC(O)=C2)C=C1

InChI Identifier

InChI=1S/C42H32O11/c43-24-5-2-20(3-6-24)1-4-21-11-30(49)19-35-36(21)37(22-12-26(45)16-27(46)13-22)41(52-35)32-9-10-33(50)39-38(23-14-28(47)17-29(48)15-23)40(53-42(32)39)31-8-7-25(44)18-34(31)51/h1-19,37-38,40-41,43-51H/b4-1+/t37-,38+,40+,41+/m0/s1

InChI Key

SBAYNGXEDJLMOG-MNBLLGGNSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
ROESY NMR	[¹H, ¹H] NMR Spectrum (2D, 600 MHz, C2D6OS, experimental)	olivier.kirchhoffer@unige.ch	University of Geneva	Olivier Kirchhoffer	2025-05-22	View Spectrum
HMBC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, C2D6OS, experimental)	olivier.kirchhoffer@unige.ch	University of Geneva	Olivier Kirchhoffer	2025-05-22	View Spectrum
HSQC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, C2D6OS, experimental)	olivier.kirchhoffer@unige.ch	University of Geneva	Olivier Kirchhoffer	2025-05-22	View Spectrum
COSY NMR	[¹H, ¹H] NMR Spectrum (2D, 600 MHz, C2D6OS, experimental)	olivier.kirchhoffer@unige.ch	University of Geneva	Olivier Kirchhoffer	2025-05-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, C2D6OS, experimental)	olivier.kirchhoffer@unige.ch	University of Geneva	Olivier Kirchhoffer	2025-05-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, C2D6OS, experimental)	olivier.kirchhoffer@unige.ch	University of Geneva	Olivier Kirchhoffer	2025-05-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600.17 MHz, C2D6OS, experimental)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, C2D6OS, experimental)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View

Chemical Shift Submissions

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 600, C2D6OS, simulated)	olivier.kirchhoffer@unige.ch	University of Geneva	Olivier Kirchhoffer	2025-05-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600.17, C2D6OS, simulated)	olivier.kirchhoffer@unige.ch	University of Geneva	Olivier Kirchhoffer	2024-05-01	View Spectrum

Species

Species of Origin

Species Name	Source	Reference
Gnetum edule		Not Available
Gnetum edule		Not Available

Chemical Taxonomy

Classification

Not classified

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	7.91	ChemAxon
pKa (Strongest Acidic)	8.43	ChemAxon
pKa (Strongest Basic)	-5.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	9	ChemAxon
Polar Surface Area	200.53 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	196.59 m³·mol⁻¹	ChemAxon
Polarizability	73.51 Å³	ChemAxon
Number of Rings	8	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

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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for (-)-Gnetuhainin M (NP0332868)

MOL for NP0332868 ((-)-Gnetuhainin M)

3D MOL for NP0332868 ((-)-Gnetuhainin M)

3D SDF for NP0332868 ((-)-Gnetuhainin M)

3D-SDF for NP0332868 ((-)-Gnetuhainin M)

PDB for NP0332868 ((-)-Gnetuhainin M)

3D PDB for NP0332868 ((-)-Gnetuhainin M)

SMILES for NP0332868 ((-)-Gnetuhainin M)

INCHI for NP0332868 ((-)-Gnetuhainin M)

Structure for NP0332868 ((-)-Gnetuhainin M)

3D Structure for NP0332868 ((-)-Gnetuhainin M)