NP-MRD: Showing NP-Card for aiphanol (NP0038952)

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Record Information

Version

2.0

Created at

2021-06-20 21:30:38 UTC

Updated at

2021-06-30 00:12:01 UTC

NP-MRD ID

NP0038952

Secondary Accession Numbers

None

Natural Product Identification

Common Name

aiphanol

Provided By

JEOL Database JEOL Logo

Description

aiphanol is found in Aiphanes aculeata. aiphanol was first documented in 2001 (PMID: 11440571). Based on a literature review a small amount of articles have been published on aiphanol (PMID: 12956057) (PMID: 33776065).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306202123303D          

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M  END

     RDKit          3D

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M  END


  Mrv1652306202123303D          

 57 60  0  0  0  0            999 V2000
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   -0.8253   -6.8865    5.8495 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0881   -5.5264    6.6905 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2487   -4.0805    2.5877 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5823   -3.7922   -0.7045 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0338   -0.1058    0.6024 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4804    2.1124   -0.5112 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3484    1.8770   -1.6252 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6299    3.6689   -0.3579 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0953    7.1111    0.1835 H   0  0  0  0  0  0  0  0  0  0  0  0
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    2.3637    0.1218   -3.0271 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1198   -2.3103   -3.3256 H   0  0  0  0  0  0  0  0  0  0  0  0
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    0.9715   -6.5008   -1.5889 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6877   -5.5136   -2.7542 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.2351   -7.4650    0.2223 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2454   -6.0289    0.6549 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7272   -7.6556    1.1509 H   0  0  0  0  0  0  0  0  0  0  0  0
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  8  7  1  0  0  0  0
  7  6  1  0  0  0  0
  6 25  1  0  0  0  0
 25 24  1  0  0  0  0
 11 10  1  0  0  0  0
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 20 13  1  0  0  0  0
  6  5  1  0  0  0  0
 10  9  1  0  0  0  0
  5  4  1  0  0  0  0
  9  8  2  0  0  0  0
  4  3  2  0  0  0  0
 17 18  1  0  0  0  0
  3 32  1  0  0  0  0
 23 22  2  0  0  0  0
 32 29  2  0  0  0  0
 13 14  2  0  0  0  0
 29 28  1  0  0  0  0
 28  5  2  0  0  0  0
 22 21  1  0  0  0  0
 32 33  1  0  0  0  0
 21 10  2  0  0  0  0
  3  2  1  0  0  0  0
 23  8  1  0  0  0  0
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  2  1  1  0  0  0  0
 15 17  2  0  0  0  0
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 13 12  1  0  0  0  0
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 18 20  2  0  0  0  0
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  6 38  1  6  0  0  0
 25 49  1  1  0  0  0
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  4 37  1  0  0  0  0
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 31 56  1  0  0  0  0
 16 43  1  0  0  0  0
 19 45  1  0  0  0  0
 27 52  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0038952

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C([H])C(\C([H])=C(/[H])C2=C([H])C([H])=C3O[C@]([H])(C([H])([H])O[H])[C@]([H])(OC3=C2[H])C2=C([H])C(OC([H])([H])[H])=C(O[H])C(OC([H])([H])[H])=C2[H])=C([H])C(O[H])=C1[H]

> <INCHI_IDENTIFIER>
InChI=1S/C25H24O8/c1-30-21-10-16(11-22(31-2)24(21)29)25-23(13-26)32-19-6-5-14(9-20(19)33-25)3-4-15-7-17(27)12-18(28)8-15/h3-12,23,25-29H,13H2,1-2H3/b4-3+/t23-,25-/m1/s1

> <INCHI_KEY>
KDMFHGGHQLUIRH-OOODPRFPSA-N

> <FORMULA>
C25H24O8

> <MOLECULAR_WEIGHT>
452.459

> <EXACT_MASS>
452.147117733

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
57

> <JCHEM_AVERAGE_POLARIZABILITY>
48.84799565645257

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5-[(E)-2-[(2R,3R)-3-(4-hydroxy-3,5-dimethoxyphenyl)-2-(hydroxymethyl)-2,3-dihydro-1,4-benzodioxin-6-yl]ethenyl]benzene-1,3-diol

> <ALOGPS_LOGP>
3.16

> <JCHEM_LOGP>
3.7540861256666673

> <ALOGPS_LOGS>
-4.56

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.326400616256578

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.568270357316385

> <JCHEM_PKA_STRONGEST_BASIC>
-2.990414902728963

> <JCHEM_POLAR_SURFACE_AREA>
117.84000000000002

> <JCHEM_REFRACTIVITY>
121.58459999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.26e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5-[(E)-2-[(2R,3R)-3-(4-hydroxy-3,5-dimethoxyphenyl)-2-(hydroxymethyl)-2,3-dihydro-1,4-benzodioxin-6-yl]ethenyl]benzene-1,3-diol

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 57 60  0  0  0  0  0  0  0  0999 V2000
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    1.8094   -0.4475   -2.2845 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6655   -1.8263   -2.4654 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9485   -2.5775   -1.5387 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8659   -3.9237   -1.7689 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4259   -4.6465   -0.5956 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1073   -6.0676   -1.0736 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9792   -6.0642   -2.0021 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5282   -5.4103    1.1266 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0287   -6.1165    2.2207 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1709   -6.8824    2.2244 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8659   -7.0006    0.9875 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3417   -6.0805    3.4491 C   0  0  0  0  0  0  0  0  0  0  0  0
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    4.6299    3.6689   -0.3579 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0953    7.1111    0.1835 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9870    7.6401   -0.4589 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1092    6.4485   -1.6252 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5646    4.3058   -1.6499 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3637    0.1218   -3.0271 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1198   -2.3103   -3.3256 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2724   -4.6882    0.1036 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1538   -6.7285   -0.2424 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9715   -6.5008   -1.5889 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6877   -5.5136   -2.7542 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0342   -5.4293    0.1655 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2351   -7.4650    0.2223 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2454   -6.0289    0.6549 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7272   -7.6556    1.1509 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6892   -7.2073    4.1214 H   0  0  0  0  0  0  0  0  0  0  0  0
 23 24  1  0
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  6 25  1  0
 25 24  1  0
 11 10  1  0
 25 26  1  0
 20 13  1  0
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 10  9  1  0
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  9  8  2  0
  4  3  2  0
 17 18  1  0
  3 32  1  0
 23 22  2  0
 32 29  2  0
 13 14  2  0
 29 28  1  0
 28  5  2  0
 22 21  1  0
 32 33  1  0
 21 10  2  0
  3  2  1  0
 23  8  1  0
 29 30  1  0
 14 15  1  0
  2  1  1  0
 15 17  2  0
 30 31  1  0
 13 12  1  0
 15 16  1  0
 18 20  2  0
 18 19  1  0
 12 11  2  0
 26 27  1  0
 17 44  1  0
 20 46  1  0
 14 42  1  0
 12 41  1  0
 11 40  1  0
  9 39  1  0
 22 48  1  0
 21 47  1  0
  6 38  1  6
 25 49  1  1
 26 50  1  0
 26 51  1  0
  4 37  1  0
 28 53  1  0
 33 57  1  0
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  1 35  1  0
  1 36  1  0
 31 54  1  0
 31 55  1  0
 31 56  1  0
 16 43  1  0
 19 45  1  0
 27 52  1  0
M  END

HEADER    PROTEIN                                 20-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-JUN-21         0                                  
HETATM    1  C   UNK     0      -0.812  -5.794   5.914  0.00  0.00           C+0
HETATM    2  O   UNK     0      -0.367  -5.213   4.698  0.00  0.00           O+0
HETATM    3  C   UNK     0      -1.160  -5.350   3.591  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.671  -4.654   2.478  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.342  -4.669   1.244  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.784  -3.933   0.038  0.00  0.00           C+0
HETATM    7  O   UNK     0      -0.408  -2.613   0.479  0.00  0.00           O+0
HETATM    8  C   UNK     0       0.345  -1.948  -0.451  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.500  -0.574  -0.262  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.244   0.189  -1.171  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.352   1.640  -0.957  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.453   2.357  -1.238  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.565   3.805  -1.007  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.788   4.325  -0.562  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.935   5.696  -0.362  0.00  0.00           C+0
HETATM   16  O   UNK     0       5.145   6.146   0.081  0.00  0.00           O+0
HETATM   17  C   UNK     0       2.885   6.571  -0.609  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.678   6.057  -1.067  0.00  0.00           C+0
HETATM   19  O   UNK     0       0.668   6.941  -1.313  0.00  0.00           O+0
HETATM   20  C   UNK     0       1.508   4.688  -1.273  0.00  0.00           C+0
HETATM   21  C   UNK     0       1.809  -0.448  -2.285  0.00  0.00           C+0
HETATM   22  C   UNK     0       1.666  -1.826  -2.465  0.00  0.00           C+0
HETATM   23  C   UNK     0       0.949  -2.578  -1.539  0.00  0.00           C+0
HETATM   24  O   UNK     0       0.866  -3.924  -1.769  0.00  0.00           O+0
HETATM   25  C   UNK     0       0.426  -4.646  -0.596  0.00  0.00           C+0
HETATM   26  C   UNK     0       0.107  -6.068  -1.074  0.00  0.00           C+0
HETATM   27  O   UNK     0      -0.979  -6.064  -2.002  0.00  0.00           O+0
HETATM   28  C   UNK     0      -2.528  -5.410   1.127  0.00  0.00           C+0
HETATM   29  C   UNK     0      -3.029  -6.117   2.221  0.00  0.00           C+0
HETATM   30  O   UNK     0      -4.171  -6.882   2.224  0.00  0.00           O+0
HETATM   31  C   UNK     0      -4.866  -7.001   0.988  0.00  0.00           C+0
HETATM   32  C   UNK     0      -2.342  -6.080   3.449  0.00  0.00           C+0
HETATM   33  O   UNK     0      -2.879  -6.801   4.487  0.00  0.00           O+0
HETATM   34  H   UNK     0      -1.781  -5.387   6.223  0.00  0.00           H+0
HETATM   35  H   UNK     0      -0.825  -6.886   5.849  0.00  0.00           H+0
HETATM   36  H   UNK     0      -0.088  -5.526   6.691  0.00  0.00           H+0
HETATM   37  H   UNK     0       0.249  -4.080   2.588  0.00  0.00           H+0
HETATM   38  H   UNK     0      -1.582  -3.792  -0.705  0.00  0.00           H+0
HETATM   39  H   UNK     0       0.034  -0.106   0.602  0.00  0.00           H+0
HETATM   40  H   UNK     0       0.480   2.112  -0.511  0.00  0.00           H+0
HETATM   41  H   UNK     0       3.348   1.877  -1.625  0.00  0.00           H+0
HETATM   42  H   UNK     0       4.630   3.669  -0.358  0.00  0.00           H+0
HETATM   43  H   UNK     0       5.095   7.111   0.184  0.00  0.00           H+0
HETATM   44  H   UNK     0       2.987   7.640  -0.459  0.00  0.00           H+0
HETATM   45  H   UNK     0      -0.109   6.449  -1.625  0.00  0.00           H+0
HETATM   46  H   UNK     0       0.565   4.306  -1.650  0.00  0.00           H+0
HETATM   47  H   UNK     0       2.364   0.122  -3.027  0.00  0.00           H+0
HETATM   48  H   UNK     0       2.120  -2.310  -3.326  0.00  0.00           H+0
HETATM   49  H   UNK     0       1.272  -4.688   0.104  0.00  0.00           H+0
HETATM   50  H   UNK     0      -0.154  -6.729  -0.242  0.00  0.00           H+0
HETATM   51  H   UNK     0       0.972  -6.501  -1.589  0.00  0.00           H+0
HETATM   52  H   UNK     0      -0.688  -5.514  -2.754  0.00  0.00           H+0
HETATM   53  H   UNK     0      -3.034  -5.429   0.166  0.00  0.00           H+0
HETATM   54  H   UNK     0      -4.235  -7.465   0.222  0.00  0.00           H+0
HETATM   55  H   UNK     0      -5.245  -6.029   0.655  0.00  0.00           H+0
HETATM   56  H   UNK     0      -5.727  -7.656   1.151  0.00  0.00           H+0
HETATM   57  H   UNK     0      -3.689  -7.207   4.121  0.00  0.00           H+0
CONECT    1    2   34   35   36                                             
CONECT    2    3    1                                                       
CONECT    3    4   32    2                                                  
CONECT    4    5    3   37                                                  
CONECT    5    6    4   28                                                  
CONECT    6    7   25    5   38                                             
CONECT    7    8    6                                                       
CONECT    8    7    9   23                                                  
CONECT    9   10    8   39                                                  
CONECT   10   11    9   21                                                  
CONECT   11   10   12   40                                                  
CONECT   12   13   11   41                                                  
CONECT   13   20   14   12                                                  
CONECT   14   13   15   42                                                  
CONECT   15   14   17   16                                                  
CONECT   16   15   43                                                       
CONECT   17   18   15   44                                                  
CONECT   18   17   20   19                                                  
CONECT   19   18   45                                                       
CONECT   20   13   18   46                                                  
CONECT   21   22   10   47                                                  
CONECT   22   23   21   48                                                  
CONECT   23   24   22    8                                                  
CONECT   24   23   25                                                       
CONECT   25    6   24   26   49                                             
CONECT   26   25   27   50   51                                             
CONECT   27   26   52                                                       
CONECT   28   29    5   53                                                  
CONECT   29   32   28   30                                                  
CONECT   30   29   31                                                       
CONECT   31   30   54   55   56                                             
CONECT   32    3   29   33                                                  
CONECT   33   32   57                                                       
CONECT   34    1                                                            
CONECT   35    1                                                            
CONECT   36    1                                                            
CONECT   37    4                                                            
CONECT   38    6                                                            
CONECT   39    9                                                            
CONECT   40   11                                                            
CONECT   41   12                                                            
CONECT   42   14                                                            
CONECT   43   16                                                            
CONECT   44   17                                                            
CONECT   45   19                                                            
CONECT   46   20                                                            
CONECT   47   21                                                            
CONECT   48   22                                                            
CONECT   49   25                                                            
CONECT   50   26                                                            
CONECT   51   26                                                            
CONECT   52   27                                                            
CONECT   53   28                                                            
CONECT   54   31                                                            
CONECT   55   31                                                            
CONECT   56   31                                                            
CONECT   57   33                                                            
MASTER        0    0    0    0    0    0    0    0   57    0  120    0
END

RDKit          3D

57 60  0  0  0  0  0  0  0  0999 V2000
   -0.8123   -5.7942    5.9144 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3673   -5.2128    4.6976 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1603   -5.3501    3.5914 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6714   -4.6540    2.4785 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3418   -4.6693    1.2436 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7841   -3.9333    0.0380 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4084   -2.6127    0.4786 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3451   -1.9481   -0.4509 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.2443    0.1894   -1.1705 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3524    1.6400   -0.9573 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4527    2.3573   -1.2379 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5652    3.8051   -1.0073 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7876    4.3254   -0.5618 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.8094   -0.4475   -2.2845 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6655   -1.8263   -2.4654 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9485   -2.5775   -1.5387 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8659   -3.9237   -1.7689 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4259   -4.6465   -0.5956 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1073   -6.0676   -1.0736 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9792   -6.0642   -2.0021 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5282   -5.4103    1.1266 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0287   -6.1165    2.2207 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1709   -6.8824    2.2244 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8659   -7.0006    0.9875 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3417   -6.0805    3.4491 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8790   -6.8011    4.4872 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7805   -5.3870    6.2227 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8253   -6.8865    5.8495 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0881   -5.5264    6.6905 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2487   -4.0805    2.5877 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5823   -3.7922   -0.7045 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0338   -0.1058    0.6024 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4804    2.1124   -0.5112 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3484    1.8770   -1.6252 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6299    3.6689   -0.3579 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0953    7.1111    0.1835 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9870    7.6401   -0.4589 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1092    6.4485   -1.6252 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5646    4.3058   -1.6499 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3637    0.1218   -3.0271 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1198   -2.3103   -3.3256 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2724   -4.6882    0.1036 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1538   -6.7285   -0.2424 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9715   -6.5008   -1.5889 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6877   -5.5136   -2.7542 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0342   -5.4293    0.1655 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2351   -7.4650    0.2223 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2454   -6.0289    0.6549 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7272   -7.6556    1.1509 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6892   -7.2073    4.1214 H   0  0  0  0  0  0  0  0  0  0  0  0
 23 24  1  0
  8  7  1  0
  7  6  1  0
  6 25  1  0
 25 24  1  0
 11 10  1  0
 25 26  1  0
 20 13  1  0
  6  5  1  0
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  5  4  1  0
  9  8  2  0
  4  3  2  0
 17 18  1  0
  3 32  1  0
 23 22  2  0
 32 29  2  0
 13 14  2  0
 29 28  1  0
 28  5  2  0
 22 21  1  0
 32 33  1  0
 21 10  2  0
  3  2  1  0
 23  8  1  0
 29 30  1  0
 14 15  1  0
  2  1  1  0
 15 17  2  0
 30 31  1  0
 13 12  1  0
 15 16  1  0
 18 20  2  0
 18 19  1  0
 12 11  2  0
 26 27  1  0
 17 44  1  0
 20 46  1  0
 14 42  1  0
 12 41  1  0
 11 40  1  0
  9 39  1  0
 22 48  1  0
 21 47  1  0
  6 38  1  6
 25 49  1  1
 26 50  1  0
 26 51  1  0
  4 37  1  0
 28 53  1  0
 33 57  1  0
  1 34  1  0
  1 35  1  0
  1 36  1  0
 31 54  1  0
 31 55  1  0
 31 56  1  0
 16 43  1  0
 19 45  1  0
 27 52  1  0
M  END

View in JSmol

Synonyms

Value	Source
(+)-Aiphanol	ChEBI

Chemical Formula

C₂₅H₂₄O₈

Average Mass

452.4590 Da

Monoisotopic Mass

452.14712 Da

IUPAC Name

5-[(E)-2-[(2R,3R)-3-(4-hydroxy-3,5-dimethoxyphenyl)-2-(hydroxymethyl)-2,3-dihydro-1,4-benzodioxin-6-yl]ethenyl]benzene-1,3-diol

Traditional Name

5-[(E)-2-[(2R,3R)-3-(4-hydroxy-3,5-dimethoxyphenyl)-2-(hydroxymethyl)-2,3-dihydro-1,4-benzodioxin-6-yl]ethenyl]benzene-1,3-diol

CAS Registry Number

Not Available

SMILES

[H]OC1=C([H])C(\C([H])=C(/[H])C2=C([H])C([H])=C3O[C@]([H])(C([H])([H])O[H])[C@]([H])(OC3=C2[H])C2=C([H])C(OC([H])([H])[H])=C(O[H])C(OC([H])([H])[H])=C2[H])=C([H])C(O[H])=C1[H]

InChI Identifier

InChI=1S/C25H24O8/c1-30-21-10-16(11-22(31-2)24(21)29)25-23(13-26)32-19-6-5-14(9-20(19)33-25)3-4-15-7-17(27)12-18(28)8-15/h3-12,23,25-29H,13H2,1-2H3/b4-3+/t23-,25-/m1/s1

InChI Key

KDMFHGGHQLUIRH-OOODPRFPSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Aiphanes aculeata	KNApSAcK Database	22123792
Aiphanes horrida	JEOL database	Lee, D., et al, Org. Lett. 3, 2169 (2001)

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	3.16	ALOGPS
logP	3.75	ChemAxon
logS	-4.6	ALOGPS
pKa (Strongest Acidic)	8.57	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	117.84 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	121.58 m³·mol⁻¹	ChemAxon
Polarizability	48.85 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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

C00054839

Chemspider ID

8542043

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10366595

PDB ID

Not Available

ChEBI ID

65377

Good Scents ID

Not Available

References

General References

Lee D, Cuendet M, Vigo JS, Graham JG, Cabieses F, Fong HH, Pezzuto JM, Kinghorn AD: A novel cyclooxygenase-inhibitory stilbenolignan from the seeds of Aiphanes aculeata. Org Lett. 2001 Jul 12;3(14):2169-71. doi: 10.1021/ol015985j. [PubMed:11440571 ]
Banwell MG, Bezos A, Chand S, Dannhardt G, Kiefer W, Nowe U, Parish CR, Savage GP, Ulbrich H: Convergent synthesis and preliminary biological evaluations of the stilbenolignan (+/-)-aiphanol and various congeners. Org Biomol Chem. 2003 Jul 21;1(14):2427-9. doi: 10.1039/b305106d. [PubMed:12956057 ]
Cetin A: In silico studies on stilbenolignan analogues as SARS-CoV-2 Mpro inhibitors. Chem Phys Lett. 2021 May 16;771:138563. doi: 10.1016/j.cplett.2021.138563. Epub 2021 Mar 22. [PubMed:33776065 ]
Lee, D., et al. (2001). Lee, D., et al, Org. Lett. 3, 2169 (2001). Org. Lett..

Showing NP-Card for aiphanol (NP0038952)

MOL for NP0038952 (aiphanol)

3D MOL for NP0038952 (aiphanol)

3D SDF for NP0038952 (aiphanol)

3D-SDF for NP0038952 (aiphanol)

PDB for NP0038952 (aiphanol)

3D PDB for NP0038952 (aiphanol)

SMILES for NP0038952 (aiphanol)

INCHI for NP0038952 (aiphanol)

Structure for NP0038952 (aiphanol)

3D Structure for NP0038952 (aiphanol)