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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 18:53:55 UTC

Update Date

2022-03-07 02:53:59 UTC

HMDB ID

HMDB0034104

Secondary Accession Numbers

HMDB34104

Metabolite Identification

Common Name

Neferine

Description

Neferine belongs to the class of organic compounds known as benzylisoquinolines. These are organic compounds containing an isoquinoline to which a benzyl group is attached. Neferine has been detected, but not quantified in, a few different foods, such as arabica coffees (Coffea arabica), coffee and coffee products, and robusta coffees (Coffea canephora). This could make neferine a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Neferine.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI


  Mrv0541 05061307352D          

 46 51  0  0  0  0            999 V2000
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0026    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    5.7158   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 10  7  1  0  0  0  0
 11  8  2  0  0  0  0
 12  9  2  0  0  0  0
 15 14  1  0  0  0  0
 16 13  1  0  0  0  0
 24  7  2  0  0  0  0
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 45 37  1  0  0  0  0
 46 34  1  0  0  0  0
 46 38  1  0  0  0  0
M  END

HMDB0034104
     RDKit          3D
Neferine
 90 95  0  0  0  0  0  0  0  0999 V2000
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   -6.9966    1.1024   -2.1251 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0831    1.0196   -1.0955 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv0541 05061307352D          

 46 51  0  0  0  0            999 V2000
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    9.2881   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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 10  7  1  0  0  0  0
 11  8  2  0  0  0  0
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 46 38  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0034104

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=CC=C(CC2N(C)CCC3=CC(OC)=C(OC4=C(O)C=CC(CC5N(C)CCC6=CC(OC)=C(OC)C=C56)=C4)C=C23)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C38H44N2O6/c1-39-15-14-27-21-36(44-5)38(23-30(27)31(39)17-24-7-10-28(42-3)11-8-24)46-34-19-25(9-12-33(34)41)18-32-29-22-37(45-6)35(43-4)20-26(29)13-16-40(32)2/h7-12,19-23,31-32,41H,13-18H2,1-6H3

> <INCHI_KEY>
MIBATSHDJRIUJK-UHFFFAOYSA-N

> <FORMULA>
C38H44N2O6

> <MOLECULAR_WEIGHT>
624.7658

> <EXACT_MASS>
624.31993715

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_AVERAGE_POLARIZABILITY>
70.16728722460749

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
4-[(6,7-dimethoxy-2-methyl-1,2,3,4-tetrahydroisoquinolin-1-yl)methyl]-2-({6-methoxy-1-[(4-methoxyphenyl)methyl]-2-methyl-1,2,3,4-tetrahydroisoquinolin-7-yl}oxy)phenol

> <ALOGPS_LOGP>
5.94

> <JCHEM_LOGP>
5.985239944599829

> <ALOGPS_LOGS>
-5.41

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
2

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.978233000620605

> <JCHEM_PKA_STRONGEST_BASIC>
8.416489555036902

> <JCHEM_POLAR_SURFACE_AREA>
72.86000000000001

> <JCHEM_REFRACTIVITY>
181.91269999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.45e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-[(6,7-dimethoxy-2-methyl-3,4-dihydro-1H-isoquinolin-1-yl)methyl]-2-({6-methoxy-1-[(4-methoxyphenyl)methyl]-2-methyl-3,4-dihydro-1H-isoquinolin-7-yl}oxy)phenol

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0034104
     RDKit          3D
Neferine
 90 95  0  0  0  0  0  0  0  0999 V2000
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M  END

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       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      10.669   4.620   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.002  -9.240   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      18.672   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      16.004  -3.080   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      12.003  -0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.335  -7.700   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.668  -5.390   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      12.003  -2.310   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      14.671   3.850   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      13.337   4.620   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      10.669   1.540   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       9.336  -0.770   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      16.004   1.540   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      13.337   0.000   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      10.669   0.000   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      14.671   2.310   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       6.668  -6.930   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      13.337   1.540   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      12.003   2.310   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      10.669  -3.080   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       9.336  -2.310   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      16.004   0.000   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      14.671  -0.770   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   39  N   UNK     0       1.334  -2.310   0.000  0.00  0.00           N+0
HETATM   40  N   UNK     0      12.003   3.850   0.000  0.00  0.00           N+0
HETATM   41  O   UNK     0      10.669  -4.620   0.000  0.00  0.00           O+0
HETATM   42  O   UNK     0       8.002  -7.700   0.000  0.00  0.00           O+0
HETATM   43  O   UNK     0      17.338  -0.770   0.000  0.00  0.00           O+0
HETATM   44  O   UNK     0       8.002   0.000   0.000  0.00  0.00           O+0
HETATM   45  O   UNK     0      14.671  -2.310   0.000  0.00  0.00           O+0
HETATM   46  O   UNK     0       8.002  -3.080   0.000  0.00  0.00           O+0
CONECT    1   39                                                            
CONECT    2   40                                                            
CONECT    3   42                                                            
CONECT    4   43                                                            
CONECT    5   44                                                            
CONECT    6   45                                                            
CONECT    7   10   24                                                       
CONECT    8   11   24                                                       
CONECT    9   12   25                                                       
CONECT   10    7   28                                                       
CONECT   11    8   28                                                       
CONECT   12    9   33                                                       
CONECT   13   16   26                                                       
CONECT   14   15   27                                                       
CONECT   15   14   39                                                       
CONECT   16   13   40                                                       
CONECT   17   24   31                                                       
CONECT   18   25   32                                                       
CONECT   19   25   34                                                       
CONECT   20   26   35                                                       
CONECT   21   27   36                                                       
CONECT   22   29   37                                                       
CONECT   23   30   38                                                       
CONECT   24    7    8   17                                                  
CONECT   25    9   18   19                                                  
CONECT   26   13   20   29                                                  
CONECT   27   14   21   30                                                  
CONECT   28   10   11   42                                                  
CONECT   29   22   26   32                                                  
CONECT   30   23   27   31                                                  
CONECT   31   17   30   39                                                  
CONECT   32   18   29   40                                                  
CONECT   33   12   34   41                                                  
CONECT   34   19   33   46                                                  
CONECT   35   20   37   43                                                  
CONECT   36   21   38   44                                                  
CONECT   37   22   35   45                                                  
CONECT   38   23   36   46                                                  
CONECT   39    1   15   31                                                  
CONECT   40    2   16   32                                                  
CONECT   41   33                                                            
CONECT   42    3   28                                                       
CONECT   43    4   35                                                       
CONECT   44    5   36                                                       
CONECT   45    6   37                                                       
CONECT   46   34   38                                                       
MASTER        0    0    0    0    0    0    0    0   46    0  102    0
END

COMPND    HMDB0034104
HETATM    1  C1  UNL     1      -4.576   4.738  -4.284  1.00  0.00           C  
HETATM    2  O1  UNL     1      -5.644   3.822  -4.201  1.00  0.00           O  
HETATM    3  C2  UNL     1      -5.766   2.903  -3.159  1.00  0.00           C  
HETATM    4  C3  UNL     1      -6.851   2.019  -3.139  1.00  0.00           C  
HETATM    5  C4  UNL     1      -6.997   1.102  -2.125  1.00  0.00           C  
HETATM    6  C5  UNL     1      -6.083   1.020  -1.095  1.00  0.00           C  
HETATM    7  C6  UNL     1      -6.267   0.048  -0.041  1.00  0.00           C  
HETATM    8  C7  UNL     1      -5.666  -1.314  -0.262  1.00  0.00           C  
HETATM    9  C8  UNL     1      -4.198  -1.329  -0.431  1.00  0.00           C  
HETATM   10  C9  UNL     1      -3.331  -1.313   0.640  1.00  0.00           C  
HETATM   11  C10 UNL     1      -1.934  -1.365   0.482  1.00  0.00           C  
HETATM   12  O2  UNL     1      -1.188  -1.342   1.612  1.00  0.00           O  
HETATM   13  C11 UNL     1      -0.226  -0.406   1.977  1.00  0.00           C  
HETATM   14  C12 UNL     1       0.967  -0.884   2.500  1.00  0.00           C  
HETATM   15  C13 UNL     1       1.974  -0.014   2.882  1.00  0.00           C  
HETATM   16  C14 UNL     1       3.153  -0.501   3.595  1.00  0.00           C  
HETATM   17  C15 UNL     1       4.272  -1.106   2.862  1.00  0.00           C  
HETATM   18  C16 UNL     1       4.986  -0.333   1.850  1.00  0.00           C  
HETATM   19  C17 UNL     1       4.869  -0.584   0.488  1.00  0.00           C  
HETATM   20  C18 UNL     1       5.632   0.128  -0.405  1.00  0.00           C  
HETATM   21  O3  UNL     1       5.529  -0.118  -1.775  1.00  0.00           O  
HETATM   22  C19 UNL     1       4.620  -1.137  -2.178  1.00  0.00           C  
HETATM   23  C20 UNL     1       6.510   1.094   0.064  1.00  0.00           C  
HETATM   24  O4  UNL     1       7.270   1.796  -0.868  1.00  0.00           O  
HETATM   25  C21 UNL     1       8.180   2.808  -0.596  1.00  0.00           C  
HETATM   26  C22 UNL     1       6.637   1.357   1.404  1.00  0.00           C  
HETATM   27  C23 UNL     1       5.864   0.632   2.308  1.00  0.00           C  
HETATM   28  C24 UNL     1       5.969   0.853   3.759  1.00  0.00           C  
HETATM   29  C25 UNL     1       5.818  -0.385   4.547  1.00  0.00           C  
HETATM   30  N1  UNL     1       5.251  -1.525   3.911  1.00  0.00           N  
HETATM   31  C26 UNL     1       6.259  -2.323   3.242  1.00  0.00           C  
HETATM   32  C27 UNL     1       1.794   1.359   2.737  1.00  0.00           C  
HETATM   33  C28 UNL     1       0.603   1.804   2.216  1.00  0.00           C  
HETATM   34  C29 UNL     1      -0.414   0.935   1.834  1.00  0.00           C  
HETATM   35  O5  UNL     1      -1.573   1.448   1.326  1.00  0.00           O  
HETATM   36  C30 UNL     1      -1.383  -1.434  -0.768  1.00  0.00           C  
HETATM   37  O6  UNL     1       0.002  -1.491  -0.966  1.00  0.00           O  
HETATM   38  C31 UNL     1       0.430  -1.577  -2.332  1.00  0.00           C  
HETATM   39  C32 UNL     1      -2.256  -1.448  -1.848  1.00  0.00           C  
HETATM   40  C33 UNL     1      -3.627  -1.397  -1.684  1.00  0.00           C  
HETATM   41  C34 UNL     1      -4.560  -1.409  -2.835  1.00  0.00           C  
HETATM   42  C35 UNL     1      -5.778  -2.191  -2.533  1.00  0.00           C  
HETATM   43  N2  UNL     1      -6.356  -2.066  -1.271  1.00  0.00           N  
HETATM   44  C36 UNL     1      -6.933  -3.297  -0.776  1.00  0.00           C  
HETATM   45  C37 UNL     1      -5.023   1.879  -1.110  1.00  0.00           C  
HETATM   46  C38 UNL     1      -4.868   2.803  -2.123  1.00  0.00           C  
HETATM   47  H1  UNL     1      -4.617   5.451  -3.432  1.00  0.00           H  
HETATM   48  H2  UNL     1      -3.618   4.170  -4.122  1.00  0.00           H  
HETATM   49  H3  UNL     1      -4.556   5.271  -5.257  1.00  0.00           H  
HETATM   50  H4  UNL     1      -7.563   2.106  -3.969  1.00  0.00           H  
HETATM   51  H5  UNL     1      -7.865   0.425  -2.147  1.00  0.00           H  
HETATM   52  H6  UNL     1      -5.896   0.403   0.960  1.00  0.00           H  
HETATM   53  H7  UNL     1      -7.364  -0.096   0.098  1.00  0.00           H  
HETATM   54  H8  UNL     1      -5.859  -1.871   0.708  1.00  0.00           H  
HETATM   55  H9  UNL     1      -3.763  -1.259   1.636  1.00  0.00           H  
HETATM   56  H10 UNL     1       1.114  -1.962   2.610  1.00  0.00           H  
HETATM   57  H11 UNL     1       3.487   0.352   4.264  1.00  0.00           H  
HETATM   58  H12 UNL     1       2.777  -1.249   4.403  1.00  0.00           H  
HETATM   59  H13 UNL     1       3.943  -2.092   2.429  1.00  0.00           H  
HETATM   60  H14 UNL     1       4.157  -1.354   0.183  1.00  0.00           H  
HETATM   61  H15 UNL     1       4.852  -2.095  -1.644  1.00  0.00           H  
HETATM   62  H16 UNL     1       3.597  -0.879  -1.902  1.00  0.00           H  
HETATM   63  H17 UNL     1       4.744  -1.362  -3.246  1.00  0.00           H  
HETATM   64  H18 UNL     1       7.758   3.824  -0.717  1.00  0.00           H  
HETATM   65  H19 UNL     1       8.708   2.729   0.377  1.00  0.00           H  
HETATM   66  H20 UNL     1       8.996   2.729  -1.375  1.00  0.00           H  
HETATM   67  H21 UNL     1       7.308   2.099   1.800  1.00  0.00           H  
HETATM   68  H22 UNL     1       5.381   1.734   4.104  1.00  0.00           H  
HETATM   69  H23 UNL     1       7.043   1.211   3.913  1.00  0.00           H  
HETATM   70  H24 UNL     1       5.129  -0.143   5.418  1.00  0.00           H  
HETATM   71  H25 UNL     1       6.789  -0.678   5.013  1.00  0.00           H  
HETATM   72  H26 UNL     1       6.542  -3.206   3.859  1.00  0.00           H  
HETATM   73  H27 UNL     1       7.167  -1.680   3.036  1.00  0.00           H  
HETATM   74  H28 UNL     1       5.919  -2.695   2.276  1.00  0.00           H  
HETATM   75  H29 UNL     1       2.575   2.041   3.026  1.00  0.00           H  
HETATM   76  H30 UNL     1       0.453   2.880   2.101  1.00  0.00           H  
HETATM   77  H31 UNL     1      -1.704   2.459   1.222  1.00  0.00           H  
HETATM   78  H32 UNL     1      -0.125  -2.490  -2.718  1.00  0.00           H  
HETATM   79  H33 UNL     1       1.489  -1.797  -2.452  1.00  0.00           H  
HETATM   80  H34 UNL     1       0.046  -0.724  -2.900  1.00  0.00           H  
HETATM   81  H35 UNL     1      -1.858  -1.497  -2.858  1.00  0.00           H  
HETATM   82  H36 UNL     1      -4.004  -1.907  -3.683  1.00  0.00           H  
HETATM   83  H37 UNL     1      -4.737  -0.375  -3.222  1.00  0.00           H  
HETATM   84  H38 UNL     1      -6.538  -1.930  -3.330  1.00  0.00           H  
HETATM   85  H39 UNL     1      -5.550  -3.271  -2.760  1.00  0.00           H  
HETATM   86  H40 UNL     1      -8.040  -3.294  -0.866  1.00  0.00           H  
HETATM   87  H41 UNL     1      -6.552  -4.135  -1.413  1.00  0.00           H  
HETATM   88  H42 UNL     1      -6.592  -3.492   0.255  1.00  0.00           H  
HETATM   89  H43 UNL     1      -4.250   1.891  -0.338  1.00  0.00           H  
HETATM   90  H44 UNL     1      -4.016   3.498  -2.138  1.00  0.00           H  
CONECT    1    2   47   48   49
CONECT    2    3
CONECT    3    4    4   46
CONECT    4    5   50
CONECT    5    6    6   51
CONECT    6    7   45
CONECT    7    8   52   53
CONECT    8    9   43   54
CONECT    9   10   10   40
CONECT   10   11   55
CONECT   11   12   36   36
CONECT   12   13
CONECT   13   14   14   34
CONECT   14   15   56
CONECT   15   16   32   32
CONECT   16   17   57   58
CONECT   17   18   30   59
CONECT   18   19   19   27
CONECT   19   20   60
CONECT   20   21   23   23
CONECT   21   22
CONECT   22   61   62   63
CONECT   23   24   26
CONECT   24   25
CONECT   25   64   65   66
CONECT   26   27   27   67
CONECT   27   28
CONECT   28   29   68   69
CONECT   29   30   70   71
CONECT   30   31
CONECT   31   72   73   74
CONECT   32   33   75
CONECT   33   34   34   76
CONECT   34   35
CONECT   35   77
CONECT   36   37   39
CONECT   37   38
CONECT   38   78   79   80
CONECT   39   40   40   81
CONECT   40   41
CONECT   41   42   82   83
CONECT   42   43   84   85
CONECT   43   44
CONECT   44   86   87   88
CONECT   45   46   46   89
CONECT   46   90
END

HMDB0034104
     RDKit          3D
Neferine
 90 95  0  0  0  0  0  0  0  0999 V2000
   -4.5765    4.7380   -4.2840 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6441    3.8223   -4.2011 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7662    2.9032   -3.1594 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8513    2.0188   -3.1387 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9966    1.1024   -2.1251 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0831    1.0196   -1.0955 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2668    0.0482   -0.0410 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6660   -1.3138   -0.2621 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1983   -1.3289   -0.4305 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3306   -1.3132    0.6402 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9344   -1.3646    0.4816 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1880   -1.3424    1.6118 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2258   -0.4062    1.9774 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9672   -0.8842    2.4997 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9739   -0.0140    2.8822 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1531   -0.5007    3.5951 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2723   -1.1062    2.8617 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9863   -0.3330    1.8499 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8692   -0.5839    0.4879 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6318    0.1284   -0.4052 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5289   -0.1175   -1.7745 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6203   -1.1368   -2.1784 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5104    1.0941    0.0637 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2700    1.7956   -0.8678 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1799    2.8080   -0.5961 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6369    1.3570    1.4042 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8638    0.6322    2.3083 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9690    0.8528    3.7592 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8179   -0.3846    4.5468 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2505   -1.5251    3.9107 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.2592   -2.3227    3.2416 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7941    1.3587    2.7365 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6034    1.8035    2.2160 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4140    0.9353    1.8343 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5733    1.4480    1.3262 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3828   -1.4336   -0.7681 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0023   -1.4908   -0.9655 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4300   -1.5767   -2.3317 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2561   -1.4482   -1.8475 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6272   -1.3969   -1.6837 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5600   -1.4088   -2.8351 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7781   -2.1913   -2.5333 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3556   -2.0663   -1.2714 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9331   -3.2968   -0.7763 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0227    1.8791   -1.1097 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8682    2.8034   -2.1230 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6171    5.4507   -3.4319 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6183    4.1704   -4.1225 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5558    5.2708   -5.2567 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5631    2.1062   -3.9695 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8647    0.4250   -2.1470 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8956    0.4029    0.9600 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3639   -0.0961    0.0982 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8594   -1.8707    0.7075 H   0  0  0  0  0  0  0  0  0  0  0  0
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    1.1142   -1.9619    2.6099 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4874    0.3518    4.2641 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7775   -1.2489    4.4032 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9434   -2.0922    2.4292 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1570   -1.3545    0.1831 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8521   -2.0953   -1.6442 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5972   -0.8791   -1.9017 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7440   -1.3618   -3.2459 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7583    3.8241   -0.7173 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7078    2.7292    0.3768 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.9964    2.7286   -1.3752 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3080    2.0985    1.7999 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3810    1.7337    4.1039 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0432    1.2105    3.9125 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1287   -0.1433    5.4183 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7889   -0.6776    5.0134 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5416   -3.2058    3.8594 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1673   -1.6800    3.0363 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9189   -2.6953    2.2764 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5747    2.0406    3.0261 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4529    2.8803    2.1010 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7045    2.4590    1.2219 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1254   -2.4903   -2.7183 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4892   -1.7968   -2.4516 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0459   -0.7241   -2.9000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8579   -1.4969   -2.8583 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0044   -1.9068   -3.6831 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7365   -0.3745   -3.2216 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5377   -1.9302   -3.3301 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5503   -3.2712   -2.7603 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0403   -3.2937   -0.8658 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5522   -4.1346   -1.4129 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5923   -3.4920    0.2547 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2496    1.8907   -0.3381 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0160    3.4977   -2.1384 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
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M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
12'-O-Methylliensinine	HMDB
Neferin	HMDB
Neferine	MeSH

Chemical Formula

C₃₈H₄₄N₂O₆

Average Molecular Weight

624.7658

Monoisotopic Molecular Weight

624.31993715

IUPAC Name

4-[(6,7-dimethoxy-2-methyl-1,2,3,4-tetrahydroisoquinolin-1-yl)methyl]-2-({6-methoxy-1-[(4-methoxyphenyl)methyl]-2-methyl-1,2,3,4-tetrahydroisoquinolin-7-yl}oxy)phenol

Traditional Name

4-[(6,7-dimethoxy-2-methyl-3,4-dihydro-1H-isoquinolin-1-yl)methyl]-2-({6-methoxy-1-[(4-methoxyphenyl)methyl]-2-methyl-3,4-dihydro-1H-isoquinolin-7-yl}oxy)phenol

CAS Registry Number

2292-16-2

SMILES

COC1=CC=C(CC2N(C)CCC3=CC(OC)=C(OC4=C(O)C=CC(CC5N(C)CCC6=CC(OC)=C(OC)C=C56)=C4)C=C23)C=C1

InChI Identifier

InChI=1S/C38H44N2O6/c1-39-15-14-27-21-36(44-5)38(23-30(27)31(39)17-24-7-10-28(42-3)11-8-24)46-34-19-25(9-12-33(34)41)18-32-29-22-37(45-6)35(43-4)20-26(29)13-16-40(32)2/h7-12,19-23,31-32,41H,13-18H2,1-6H3

InChI Key

MIBATSHDJRIUJK-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as benzylisoquinolines. These are organic compounds containing an isoquinoline to which a benzyl group is attached.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Isoquinolines and derivatives

Sub Class

Benzylisoquinolines

Direct Parent

Benzylisoquinolines

Alternative Parents

Substituents

Benzylisoquinoline
Diaryl ether
Tetrahydroisoquinoline
Phenoxy compound
Anisole
Methoxybenzene
Phenol ether
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
Aralkylamine
Phenol
Monocyclic benzene moiety
Benzenoid
Tertiary aliphatic amine
Tertiary amine
Ether
Azacycle
Organooxygen compound
Organonitrogen compound
Hydrocarbon derivative
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Amine
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cell membrane (HMDB: HMDB0034104)

Cellular substructure

Membrane (HMDB: HMDB0034104)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0034104)

Source

Exogenous

Food

Food (HMDB: HMDB0034104)

Coffee and coffee product

Coffee

Arabica coffee (FooDB: FOOD00059)
Robusta coffee (FooDB: FOOD00060)

Coffee and coffee products (FooDB: FOOD00861)

Endogenous

Plant

Coffea (HMDB: HMDB0034104)

Not Available

Nutrient (HMDB: HMDB0034104)

Industrial application

Pharmaceutical industry

Sedative (HMDB: HMDB0034104)

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.0078 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.0024 g/L	ALOGPS
logP	5.94	ALOGPS
logP	5.99	ChemAxon
logS	-5.4	ALOGPS
pKa (Strongest Acidic)	8.98	ChemAxon
pKa (Strongest Basic)	8.42	ChemAxon
Physiological Charge	2	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	72.86 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	181.91 m³·mol⁻¹	ChemAxon
Polarizability	70.17 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	243.511	31661259
DarkChem	[M-H]-	239.985	31661259
DeepCCS	[M-2H]-	268.898	30932474
DeepCCS	[M+Na]+	243.463	30932474
AllCCS	[M+H]+	254.0	32859911
AllCCS	[M+H-H2O]+	252.9	32859911
AllCCS	[M+NH4]+	255.0	32859911
AllCCS	[M+Na]+	255.2	32859911
AllCCS	[M-H]-	234.4	32859911
AllCCS	[M+Na-2H]-	236.4	32859911
AllCCS	[M+HCOO]-	238.7	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Neferine	COC1=CC=C(CC2N(C)CCC3=CC(OC)=C(OC4=C(O)C=CC(CC5N(C)CCC6=CC(OC)=C(OC)C=C56)=C4)C=C23)C=C1	5984.8	Standard polar	33892256
Neferine	COC1=CC=C(CC2N(C)CCC3=CC(OC)=C(OC4=C(O)C=CC(CC5N(C)CCC6=CC(OC)=C(OC)C=C56)=C4)C=C23)C=C1	4722.4	Standard non polar	33892256
Neferine	COC1=CC=C(CC2N(C)CCC3=CC(OC)=C(OC4=C(O)C=CC(CC5N(C)CCC6=CC(OC)=C(OC)C=C56)=C4)C=C23)C=C1	4821.0	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Neferine,1TMS,isomer #1	COC1=CC=C(CC2C3=CC(OC4=CC(CC5C6=CC(OC)=C(OC)C=C6CCN5C)=CC=C4O[Si](C)(C)C)=C(OC)C=C3CCN2C)C=C1	4800.1	Semi standard non polar	33892256
Neferine,1TBDMS,isomer #1	COC1=CC=C(CC2C3=CC(OC4=CC(CC5C6=CC(OC)=C(OC)C=C6CCN5C)=CC=C4O[Si](C)(C)C(C)(C)C)=C(OC)C=C3CCN2C)C=C1	4986.3	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Neferine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4i-0090110000-5011ddd749bf2582c46f	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Neferine GC-MS (1 TMS) - 70eV, Positive	splash10-0a4i-0090011000-35c242e0fe8b2bfe8bdc	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Neferine GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-10-16	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Neferine GC-MS ("Neferine,1TMS,#1" TMS) - 70eV, Positive	Not Available	2021-11-02	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Neferine 10V, Positive-QTOF	splash10-004i-0000049000-d2b32b64d549c2e8f761	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Neferine 20V, Positive-QTOF	splash10-0a4m-0351392000-3658f0c63fd419dd7f0e	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Neferine 40V, Positive-QTOF	splash10-0a4i-0981122000-bc32da800294e1a60b88	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Neferine 10V, Negative-QTOF	splash10-00di-0001009000-df184214f3d21176140b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Neferine 20V, Negative-QTOF	splash10-076r-0047039000-05f9f4d9fecfa02fa1e3	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Neferine 40V, Negative-QTOF	splash10-01ot-0094000000-27a6f5eec68243c466e2	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Neferine 10V, Negative-QTOF	splash10-00di-0000009000-e9f967e70ad3a41e512c	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Neferine 20V, Negative-QTOF	splash10-006x-0011096000-38decd138d0975d20100	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Neferine 40V, Negative-QTOF	splash10-00di-0110197000-9d3326d11f46eae1972e	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Neferine 10V, Positive-QTOF	splash10-004i-0001009000-669e0c83506fa2536d15	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Neferine 20V, Positive-QTOF	splash10-00vl-3430194000-825e71f6670275792adf	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Neferine 40V, Positive-QTOF	splash10-00gi-6473294000-89147f58a303d0ac84fb	2021-09-22	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB012368

KNApSAcK ID

C00053535

Chemspider ID

353522

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

398793

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1840551

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Sugimoto Y, Furutani S, Itoh A, Tanahashi T, Nakajima H, Oshiro H, Sun S, Yamada J: Effects of extracts and neferine from the embryo of Nelumbo nucifera seeds on the central nervous system. Phytomedicine. 2008 Dec;15(12):1117-24. doi: 10.1016/j.phymed.2008.09.005. [PubMed:19010651 ]
(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for Neferine (HMDB0034104)

MOL for HMDB0034104 (Neferine)

3D MOL for HMDB0034104 (Neferine)

3D SDF for HMDB0034104 (Neferine)

3D-SDF for HMDB0034104 (Neferine)

PDB for HMDB0034104 (Neferine)

3D PDB for HMDB0034104 (Neferine)

SMILES for HMDB0034104 (Neferine)

INCHI for HMDB0034104 (Neferine)

Structure for HMDB0034104 (Neferine)

3D Structure for HMDB0034104 (Neferine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra