NP-MRD: Showing NP-Card for (+)-9'-isovaleryllariciresinol (NP0035236)

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Record Information

Version

2.0

Created at

2021-06-20 18:44:17 UTC

Updated at

2021-06-30 00:06:06 UTC

NP-MRD ID

NP0035236

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(+)-9'-isovaleryllariciresinol

Provided By

JEOL Database JEOL Logo

Description

(+)-9'-Isovaleroxylariciresinol belongs to the class of organic compounds known as 7,9'-epoxylignans. These are lignans that contain the 7,9'-epoxylignan skeleton, which consists of a tetrahydrofuran that carries a phenyl group, a methyl group, and a benzyl group at the 2-, 3-, 4-position, respectively. (+)-9'-isovaleryllariciresinol is found in Aegle marmelos and Valeriana jatamansi. (+)-9'-isovaleryllariciresinol was first documented in 2010 (PMID: 20151678). Based on a literature review very few articles have been published on (+)-9'-isovaleroxylariciresinol (PMID: 23434131).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306202120443D          

 64 66  0  0  0  0            999 V2000
    2.1567    4.0840   -3.1170 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3034    3.2908   -3.4041 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6238    2.3226   -2.4874 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0011    2.1153   -1.2555 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4103    1.0640   -0.4125 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7229    0.8455    0.9173 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1016   -0.5570    1.1100 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7117   -0.7494    2.5728 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4059   -0.1815    2.7276 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2218   -0.1083    1.4292 C   0  0  2  0  0  0  0  0  0  0  0  0
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   -1.8203   -2.0461    1.8500 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1097   -2.5739    1.9070 C   0  0  0  0  0  0  0  0  0  0  0  0
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    5.1171    0.4587   -2.0306 C   0  0  0  0  0  0  0  0  0  0  0  0
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    5.3173    1.6660   -4.0543 O   0  0  0  0  0  0  0  0  0  0  0  0
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    1.9676    1.6236    1.0806 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8231   -1.3276    0.8172 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.2912    0.9602    1.1898 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.2674   -3.6211    2.1460 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0529   -1.5413    1.5327 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -6.0735    2.1290    0.8864 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5082    1.9625    0.0839 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5660    1.1791    1.0778 H   0  0  0  0  0  0  0  0  0  0  0  0
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    4.8688    2.4319   -4.4628 H   0  0  0  0  0  0  0  0  0  0  0  0
  6  5  1  0  0  0  0
 14 15  1  0  0  0  0
  5 29  1  0  0  0  0
 29 30  2  0  0  0  0
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 12 11  2  0  0  0  0
 31  3  2  0  0  0  0
  3  4  1  0  0  0  0
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M  END

     RDKit          3D

 64 66  0  0  0  0  0  0  0  0999 V2000
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M  END


  Mrv1652306202120443D          

 64 66  0  0  0  0            999 V2000
    2.1567    4.0840   -3.1170 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3034    3.2908   -3.4041 O   0  0  0  0  0  0  0  0  0  0  0  0
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    3.0011    2.1153   -1.2555 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4103    1.0640   -0.4125 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7229    0.8455    0.9173 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1016   -0.5570    1.1100 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7117   -0.7494    2.5728 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4059   -0.1815    2.7276 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2218   -0.1083    1.4292 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6132   -0.6939    1.5326 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8203   -2.0461    1.8500 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1097   -2.5739    1.9070 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1950   -1.7451    1.6607 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.2912    0.9602    1.1898 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.6028   -0.0574   -4.9220 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8413   -0.5492   -0.1618 H   0  0  0  0  0  0  0  0  0  0  0  0
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    4.8688    2.4319   -4.4628 H   0  0  0  0  0  0  0  0  0  0  0  0
  6  5  1  0  0  0  0
 14 15  1  0  0  0  0
  5 29  1  0  0  0  0
 29 30  2  0  0  0  0
 17 18  1  0  0  0  0
 30 31  1  0  0  0  0
 12 11  2  0  0  0  0
 31  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
 10  9  1  0  0  0  0
 20 21  1  0  0  0  0
 14 13  2  0  0  0  0
 21 22  1  0  0  0  0
 11 19  1  0  0  0  0
 22 23  1  0  0  0  0
 19 16  2  0  0  0  0
 23 25  1  0  0  0  0
 16 14  1  0  0  0  0
 25 26  1  0  0  0  0
  9  8  1  0  0  0  0
 31 32  1  0  0  0  0
  8  7  1  0  0  0  0
  3  2  1  0  0  0  0
  7 20  1  0  0  0  0
  2  1  1  0  0  0  0
 20 10  1  0  0  0  0
 23 24  2  0  0  0  0
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 28 60  1  0  0  0  0
 28 61  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0035236

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C([H])C([H])=C(C([H])=C1OC([H])([H])[H])[C@@]1([H])OC([H])([H])[C@]([H])(C([H])([H])C2=C([H])C(OC([H])([H])[H])=C(O[H])C([H])=C2[H])[C@]1([H])C([H])([H])OC(=O)C([H])([H])C([H])(C([H])([H])[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C25H32O7/c1-15(2)9-24(28)31-14-19-18(10-16-5-7-20(26)22(11-16)29-3)13-32-25(19)17-6-8-21(27)23(12-17)30-4/h5-8,11-12,15,18-19,25-27H,9-10,13-14H2,1-4H3/t18-,19-,25+/m0/s1

> <INCHI_KEY>
VOGRFGIBINTSKJ-XHNVNVPESA-N

> <FORMULA>
C25H32O7

> <MOLECULAR_WEIGHT>
444.524

> <EXACT_MASS>
444.21480337

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
64

> <JCHEM_AVERAGE_POLARIZABILITY>
47.476017494824376

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
[(2S,3R,4R)-2-(4-hydroxy-3-methoxyphenyl)-4-[(4-hydroxy-3-methoxyphenyl)methyl]oxolan-3-yl]methyl 3-methylbutanoate

> <ALOGPS_LOGP>
3.99

> <JCHEM_LOGP>
4.178559333666666

> <ALOGPS_LOGS>
-4.85

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
10.423201531141554

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.751300225120694

> <JCHEM_PKA_STRONGEST_BASIC>
-4.037868039774152

> <JCHEM_POLAR_SURFACE_AREA>
94.45

> <JCHEM_REFRACTIVITY>
120.12160000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.28e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[(2S,3R,4R)-2-(4-hydroxy-3-methoxyphenyl)-4-[(4-hydroxy-3-methoxyphenyl)methyl]oxolan-3-yl]methyl 3-methylbutanoate

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 64 66  0  0  0  0  0  0  0  0999 V2000
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  6  5  1  0
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 29 30  2  0
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 31  3  2  0
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 23 24  2  0
 16 17  1  0
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 26 28  1  0
 13 12  1  0
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 18 48  1  0
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 28 60  1  0
 28 61  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       2.157   4.084  -3.117  0.00  0.00           C+0
HETATM    2  O   UNK     0       3.303   3.291  -3.404  0.00  0.00           O+0
HETATM    3  C   UNK     0       3.624   2.323  -2.487  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.001   2.115  -1.256  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.410   1.064  -0.413  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.723   0.846   0.917  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.102  -0.557   1.110  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.712  -0.749   2.573  0.00  0.00           C+0
HETATM    9  O   UNK     0       0.406  -0.182   2.728  0.00  0.00           O+0
HETATM   10  C   UNK     0      -0.222  -0.108   1.429  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.613  -0.694   1.533  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.820  -2.046   1.850  0.00  0.00           C+0
HETATM   13  C   UNK     0      -3.110  -2.574   1.907  0.00  0.00           C+0
HETATM   14  C   UNK     0      -4.195  -1.745   1.661  0.00  0.00           C+0
HETATM   15  O   UNK     0      -5.450  -2.289   1.711  0.00  0.00           O+0
HETATM   16  C   UNK     0      -4.028  -0.388   1.372  0.00  0.00           C+0
HETATM   17  O   UNK     0      -5.190   0.307   1.153  0.00  0.00           O+0
HETATM   18  C   UNK     0      -5.066   1.716   0.993  0.00  0.00           C+0
HETATM   19  C   UNK     0      -2.734   0.132   1.313  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.740  -0.802   0.449  0.00  0.00           C+0
HETATM   21  C   UNK     0       0.579  -0.358  -1.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      -0.607  -0.950  -1.559  0.00  0.00           O+0
HETATM   23  C   UNK     0      -1.643  -0.113  -1.849  0.00  0.00           C+0
HETATM   24  O   UNK     0      -1.638   1.098  -1.674  0.00  0.00           O+0
HETATM   25  C   UNK     0      -2.802  -0.927  -2.382  0.00  0.00           C+0
HETATM   26  C   UNK     0      -4.013  -0.070  -2.780  0.00  0.00           C+0
HETATM   27  C   UNK     0      -5.265  -0.943  -2.884  0.00  0.00           C+0
HETATM   28  C   UNK     0      -3.773   0.654  -4.106  0.00  0.00           C+0
HETATM   29  C   UNK     0       4.483   0.250  -0.807  0.00  0.00           C+0
HETATM   30  C   UNK     0       5.117   0.459  -2.031  0.00  0.00           C+0
HETATM   31  C   UNK     0       4.681   1.486  -2.856  0.00  0.00           C+0
HETATM   32  O   UNK     0       5.317   1.666  -4.054  0.00  0.00           O+0
HETATM   33  H   UNK     0       2.317   4.696  -2.223  0.00  0.00           H+0
HETATM   34  H   UNK     0       2.001   4.763  -3.961  0.00  0.00           H+0
HETATM   35  H   UNK     0       1.260   3.463  -3.018  0.00  0.00           H+0
HETATM   36  H   UNK     0       2.187   2.756  -0.930  0.00  0.00           H+0
HETATM   37  H   UNK     0       3.486   1.014   1.689  0.00  0.00           H+0
HETATM   38  H   UNK     0       1.968   1.624   1.081  0.00  0.00           H+0
HETATM   39  H   UNK     0       2.823  -1.328   0.817  0.00  0.00           H+0
HETATM   40  H   UNK     0       1.641  -1.815   2.821  0.00  0.00           H+0
HETATM   41  H   UNK     0       2.401  -0.283   3.283  0.00  0.00           H+0
HETATM   42  H   UNK     0      -0.291   0.960   1.190  0.00  0.00           H+0
HETATM   43  H   UNK     0      -0.976  -2.698   2.061  0.00  0.00           H+0
HETATM   44  H   UNK     0      -3.267  -3.621   2.146  0.00  0.00           H+0
HETATM   45  H   UNK     0      -6.053  -1.541   1.533  0.00  0.00           H+0
HETATM   46  H   UNK     0      -4.608   2.176   1.875  0.00  0.00           H+0
HETATM   47  H   UNK     0      -6.074   2.129   0.886  0.00  0.00           H+0
HETATM   48  H   UNK     0      -4.508   1.962   0.084  0.00  0.00           H+0
HETATM   49  H   UNK     0      -2.566   1.179   1.078  0.00  0.00           H+0
HETATM   50  H   UNK     0       0.563  -1.887   0.478  0.00  0.00           H+0
HETATM   51  H   UNK     0       1.414  -0.736  -1.599  0.00  0.00           H+0
HETATM   52  H   UNK     0       0.570   0.731  -1.093  0.00  0.00           H+0
HETATM   53  H   UNK     0      -2.453  -1.511  -3.241  0.00  0.00           H+0
HETATM   54  H   UNK     0      -3.091  -1.623  -1.585  0.00  0.00           H+0
HETATM   55  H   UNK     0      -4.197   0.687  -2.007  0.00  0.00           H+0
HETATM   56  H   UNK     0      -6.138  -0.341  -3.158  0.00  0.00           H+0
HETATM   57  H   UNK     0      -5.141  -1.726  -3.640  0.00  0.00           H+0
HETATM   58  H   UNK     0      -5.482  -1.427  -1.926  0.00  0.00           H+0
HETATM   59  H   UNK     0      -2.903   1.315  -4.049  0.00  0.00           H+0
HETATM   60  H   UNK     0      -4.638   1.270  -4.373  0.00  0.00           H+0
HETATM   61  H   UNK     0      -3.603  -0.057  -4.922  0.00  0.00           H+0
HETATM   62  H   UNK     0       4.841  -0.549  -0.162  0.00  0.00           H+0
HETATM   63  H   UNK     0       5.946  -0.171  -2.338  0.00  0.00           H+0
HETATM   64  H   UNK     0       4.869   2.432  -4.463  0.00  0.00           H+0
CONECT    1    2   33   34   35                                             
CONECT    2    3    1                                                       
CONECT    3   31    4    2                                                  
CONECT    4    3    5   36                                                  
CONECT    5    6   29    4                                                  
CONECT    6    5    7   37   38                                             
CONECT    7    8   20    6   39                                             
CONECT    8    9    7   40   41                                             
CONECT    9   10    8                                                       
CONECT   10    9   20   11   42                                             
CONECT   11   12   19   10                                                  
CONECT   12   11   13   43                                                  
CONECT   13   14   12   44                                                  
CONECT   14   15   13   16                                                  
CONECT   15   14   45                                                       
CONECT   16   19   14   17                                                  
CONECT   17   18   16                                                       
CONECT   18   17   46   47   48                                             
CONECT   19   11   16   49                                                  
CONECT   20   21    7   10   50                                             
CONECT   21   20   22   51   52                                             
CONECT   22   21   23                                                       
CONECT   23   22   25   24                                                  
CONECT   24   23                                                            
CONECT   25   23   26   53   54                                             
CONECT   26   25   27   28   55                                             
CONECT   27   26   56   57   58                                             
CONECT   28   26   59   60   61                                             
CONECT   29    5   30   62                                                  
CONECT   30   29   31   63                                                  
CONECT   31   30    3   32                                                  
CONECT   32   31   64                                                       
CONECT   33    1                                                            
CONECT   34    1                                                            
CONECT   35    1                                                            
CONECT   36    4                                                            
CONECT   37    6                                                            
CONECT   38    6                                                            
CONECT   39    7                                                            
CONECT   40    8                                                            
CONECT   41    8                                                            
CONECT   42   10                                                            
CONECT   43   12                                                            
CONECT   44   13                                                            
CONECT   45   15                                                            
CONECT   46   18                                                            
CONECT   47   18                                                            
CONECT   48   18                                                            
CONECT   49   19                                                            
CONECT   50   20                                                            
CONECT   51   21                                                            
CONECT   52   21                                                            
CONECT   53   25                                                            
CONECT   54   25                                                            
CONECT   55   26                                                            
CONECT   56   27                                                            
CONECT   57   27                                                            
CONECT   58   27                                                            
CONECT   59   28                                                            
CONECT   60   28                                                            
CONECT   61   28                                                            
CONECT   62   29                                                            
CONECT   63   30                                                            
CONECT   64   32                                                            
MASTER        0    0    0    0    0    0    0    0   64    0  132    0
END

RDKit          3D

64 66  0  0  0  0  0  0  0  0999 V2000
    2.1567    4.0840   -3.1170 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3034    3.2908   -3.4041 O   0  0  0  0  0  0  0  0  0  0  0  0
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    3.0011    2.1153   -1.2555 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4103    1.0640   -0.4125 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7229    0.8455    0.9173 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1016   -0.5570    1.1100 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7117   -0.7494    2.5728 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4059   -0.1815    2.7276 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2218   -0.1083    1.4292 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6132   -0.6939    1.5326 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8203   -2.0461    1.8500 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1097   -2.5739    1.9070 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1950   -1.7451    1.6607 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.7398   -0.8019    0.4492 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5788   -0.3578   -1.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.6376    1.0978   -1.6737 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8020   -0.9270   -2.3821 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0131   -0.0697   -2.7795 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.2646   -0.9429   -2.8841 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7728    0.6540   -4.1065 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4831    0.2499   -0.8068 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1171    0.4587   -2.0306 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6813    1.4857   -2.8560 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3173    1.6660   -4.0543 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3166    4.6957   -2.2231 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0011    4.7627   -3.9611 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2596    3.4635   -3.0185 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1870    2.7556   -0.9297 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4863    1.0135    1.6894 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9676    1.6236    1.0806 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8231   -1.3276    0.8172 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6407   -1.8150    2.8206 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4009   -0.2830    3.2828 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2912    0.9602    1.1898 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9760   -2.6981    2.0611 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2674   -3.6211    2.1460 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0529   -1.5413    1.5327 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6084    2.1758    1.8751 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0735    2.1290    0.8864 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5082    1.9625    0.0839 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5660    1.1791    1.0778 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5626   -1.8865    0.4781 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4136   -0.7362   -1.5989 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5699    0.7313   -1.0928 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4530   -1.5114   -3.2413 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0909   -1.6229   -1.5854 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1966    0.6865   -2.0070 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1375   -0.3410   -3.1581 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1412   -1.7263   -3.6397 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4823   -1.4265   -1.9257 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9026    1.3150   -4.0487 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6384    1.2701   -4.3727 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6028   -0.0574   -4.9220 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8413   -0.5492   -0.1618 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9464   -0.1711   -2.3385 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8688    2.4319   -4.4628 H   0  0  0  0  0  0  0  0  0  0  0  0
  6  5  1  0
 14 15  1  0
  5 29  1  0
 29 30  2  0
 17 18  1  0
 30 31  1  0
 12 11  2  0
 31  3  2  0
  3  4  1  0
  4  5  2  0
 10  9  1  0
 20 21  1  0
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 11 19  1  0
 22 23  1  0
 19 16  2  0
 23 25  1  0
 16 14  1  0
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  9  8  1  0
 31 32  1  0
  8  7  1  0
  3  2  1  0
  7 20  1  0
  2  1  1  0
 20 10  1  0
 23 24  2  0
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  7  6  1  0
 26 28  1  0
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 12 43  1  0
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  6 37  1  0
  6 38  1  0
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 32 64  1  0
  1 33  1  0
  1 34  1  0
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 27 56  1  0
 27 57  1  0
 27 58  1  0
 28 59  1  0
 28 60  1  0
 28 61  1  0
M  END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₅H₃₂O₇

Average Mass

444.5240 Da

Monoisotopic Mass

444.21480 Da

IUPAC Name

[(2S,3R,4R)-2-(4-hydroxy-3-methoxyphenyl)-4-[(4-hydroxy-3-methoxyphenyl)methyl]oxolan-3-yl]methyl 3-methylbutanoate

Traditional Name

[(2S,3R,4R)-2-(4-hydroxy-3-methoxyphenyl)-4-[(4-hydroxy-3-methoxyphenyl)methyl]oxolan-3-yl]methyl 3-methylbutanoate

CAS Registry Number

Not Available

SMILES

[H]OC1=C([H])C([H])=C(C([H])=C1OC([H])([H])[H])[C@@]1([H])OC([H])([H])[C@]([H])(C([H])([H])C2=C([H])C(OC([H])([H])[H])=C(O[H])C([H])=C2[H])[C@]1([H])C([H])([H])OC(=O)C([H])([H])C([H])(C([H])([H])[H])C([H])([H])[H]

InChI Identifier

InChI=1S/C25H32O7/c1-15(2)9-24(28)31-14-19-18(10-16-5-7-20(26)22(11-16)29-3)13-32-25(19)17-6-8-21(27)23(12-17)30-4/h5-8,11-12,15,18-19,25-27H,9-10,13-14H2,1-4H3/t18-,19-,25+/m0/s1

InChI Key

VOGRFGIBINTSKJ-XHNVNVPESA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
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, 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, 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, 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
Aegle marmelos	LOTUS Database	35616633
Valeriana jatamansi	JEOL database	Lin, S., et al, J. Nat. Prod. 73, 632 (2010)

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 7,9'-epoxylignans. These are lignans that contain the 7,9'-epoxylignan skeleton, which consists of a tetrahydrofuran that carries a phenyl group, a methyl group, and a benzyl group at the 2-, 3-, 4-position, respectively.

Kingdom

Organic compounds

Super Class

Lignans, neolignans and related compounds

Class

Furanoid lignans

Sub Class

Tetrahydrofuran lignans

Direct Parent

7,9'-epoxylignans

Alternative Parents

Substituents

7,9p-epoxylignan
Methoxyphenol
Phenoxy compound
Anisole
Methoxybenzene
Phenol ether
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Fatty acid ester
Phenol
Monocyclic benzene moiety
Fatty acyl
Benzenoid
Oxolane
Carboxylic acid ester
Monocarboxylic acid or derivatives
Organoheterocyclic compound
Oxacycle
Ether
Dialkyl ether
Carboxylic acid derivative
Organooxygen compound
Carbonyl group
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	3.99	ALOGPS
logP	4.18	ChemAxon
logS	-4.8	ALOGPS
pKa (Strongest Acidic)	9.75	ChemAxon
pKa (Strongest Basic)	-4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	94.45 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	120.12 m³·mol⁻¹	ChemAxon
Polarizability	47.48 Å³	ChemAxon
Number of Rings	3	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

Not Available

Chemspider ID

24671214

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

46211187

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Li J, Mahdi F, Du L, Jekabsons MB, Zhou YD, Nagle DG: Semisynthetic studies identify mitochondria poisons from botanical dietary supplements--geranyloxycoumarins from Aegle marmelos. Bioorg Med Chem. 2013 Apr 1;21(7):1795-803. doi: 10.1016/j.bmc.2013.01.048. Epub 2013 Feb 4. [PubMed:23434131 ]
Lin S, Chen T, Liu XH, Shen YH, Li HL, Shan L, Liu RH, Xu XK, Zhang WD, Wang H: Iridoids and lignans from Valeriana jatamansi. J Nat Prod. 2010 Apr 23;73(4):632-8. doi: 10.1021/np900795c. [PubMed:20151678 ]
Lin, S., et al. (2010). Lin, S., et al, J. Nat. Prod. 73, 632 (2010). J. Nat. Prod..

Showing NP-Card for (+)-9'-isovaleryllariciresinol (NP0035236)

MOL for NP0035236 ((+)-9'-isovaleryllariciresinol)

3D MOL for NP0035236 ((+)-9'-isovaleryllariciresinol)

3D SDF for NP0035236 ((+)-9'-isovaleryllariciresinol)

3D-SDF for NP0035236 ((+)-9'-isovaleryllariciresinol)

PDB for NP0035236 ((+)-9'-isovaleryllariciresinol)

3D PDB for NP0035236 ((+)-9'-isovaleryllariciresinol)

SMILES for NP0035236 ((+)-9'-isovaleryllariciresinol)

INCHI for NP0035236 ((+)-9'-isovaleryllariciresinol)

Structure for NP0035236 ((+)-9'-isovaleryllariciresinol)

3D Structure for NP0035236 ((+)-9'-isovaleryllariciresinol)