NP-MRD: Showing NP-Card for (8R,8'R)-4-hydroxycubebinone (NP0027952)

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Record Information

Version

1.0

Created at

2021-06-19 19:58:04 UTC

Updated at

2021-06-29 23:54:25 UTC

NP-MRD ID

NP0027952

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(8R,8'R)-4-hydroxycubebinone

Provided By

JEOL Database JEOL Logo

Description

(8R,8'R)-4-hydroxycubebinone is found in Piper cubeba. It was first documented in 2005 (Usia, T., et al.). Based on a literature review very few articles have been published on (8R,8'R)-4-hydroxycubebinone.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306192121583D          

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M  END

     RDKit          3D

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  Mrv1652306192121583D          

 54 57  0  0  0  0            999 V2000
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    0.1653   -0.2552   -4.5728 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7631    2.4344   -3.1157 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1641    6.2067   -1.3004 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1813    6.4742   -3.0936 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6351    6.7220   -2.1244 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2674    0.9054   -3.5448 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7439    5.2855   -3.1832 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7468    4.7799   -1.4758 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4981   -1.5009    1.1037 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5313    0.3833    4.5108 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0557   -1.1801    5.1675 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8647    0.1171    5.1836 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7488    3.1006    3.6338 H   0  0  0  0  0  0  0  0  0  0  0  0
 29 26  2  0  0  0  0
  2  1  1  0  0  0  0
 10  9  1  0  0  0  0
 29 30  1  0  0  0  0
 26 25  1  0  0  0  0
 26 27  1  0  0  0  0
  9  8  1  0  0  0  0
 27 28  1  0  0  0  0
 25  5  2  0  0  0  0
 14 21  2  0  0  0  0
 21 20  1  0  0  0  0
  8  7  1  0  0  0  0
 19 16  1  0  0  0  0
  5  4  1  0  0  0  0
 16 15  2  0  0  0  0
 15 14  1  0  0  0  0
 19 20  2  0  0  0  0
  4  3  2  0  0  0  0
  7 12  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
 20 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 19  1  0  0  0  0
 12 13  1  0  0  0  0
 16 17  1  0  0  0  0
  3 29  1  0  0  0  0
 17 18  1  0  0  0  0
 13 14  1  0  0  0  0
 10 11  2  0  0  0  0
 12 10  1  0  0  0  0
 12 40  1  6  0  0  0
  3  2  1  0  0  0  0
  7 37  1  1  0  0  0
  8 38  1  0  0  0  0
  8 39  1  0  0  0  0
 25 50  1  0  0  0  0
  4 34  1  0  0  0  0
  6 35  1  0  0  0  0
  6 36  1  0  0  0  0
 13 41  1  0  0  0  0
 13 42  1  0  0  0  0
  1 31  1  0  0  0  0
  1 32  1  0  0  0  0
  1 33  1  0  0  0  0
 30 54  1  0  0  0  0
 28 51  1  0  0  0  0
 28 52  1  0  0  0  0
 28 53  1  0  0  0  0
 21 47  1  0  0  0  0
 15 43  1  0  0  0  0
 23 48  1  0  0  0  0
 23 49  1  0  0  0  0
 18 44  1  0  0  0  0
 18 45  1  0  0  0  0
 18 46  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0027952

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C(OC([H])([H])[H])C([H])=C(C([H])=C1OC([H])([H])[H])C([H])([H])[C@@]1([H])C([H])([H])OC(=O)[C@]1([H])C([H])([H])C1=C([H])C2=C(OC([H])([H])O2)C(OC([H])([H])[H])=C1[H]

> <INCHI_IDENTIFIER>
InChI=1S/C22H24O8/c1-25-16-6-12(7-17(26-2)20(16)23)4-14-10-28-22(24)15(14)5-13-8-18(27-3)21-19(9-13)29-11-30-21/h6-9,14-15,23H,4-5,10-11H2,1-3H3/t14-,15+/m0/s1

> <INCHI_KEY>
LSSNBHGWOAHIQS-LSDHHAIUSA-N

> <FORMULA>
C22H24O8

> <MOLECULAR_WEIGHT>
416.426

> <EXACT_MASS>
416.147117733

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
54

> <JCHEM_AVERAGE_POLARIZABILITY>
42.29372782838448

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3R,4R)-4-[(4-hydroxy-3,5-dimethoxyphenyl)methyl]-3-[(7-methoxy-2H-1,3-benzodioxol-5-yl)methyl]oxolan-2-one

> <ALOGPS_LOGP>
2.55

> <JCHEM_LOGP>
3.060910034666666

> <ALOGPS_LOGS>
-4.26

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.34018578933225

> <JCHEM_PKA_STRONGEST_BASIC>
-4.2679476510828165

> <JCHEM_POLAR_SURFACE_AREA>
92.68000000000002

> <JCHEM_REFRACTIVITY>
105.88360000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.31e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3R,4R)-4-[(4-hydroxy-3,5-dimethoxyphenyl)methyl]-3-[(7-methoxy-2H-1,3-benzodioxol-5-yl)methyl]oxolan-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 54 57  0  0  0  0  0  0  0  0999 V2000
   -2.4127    4.4995    0.8870 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9769    3.6602    1.8902 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0778    2.3221    1.5890 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7038    1.7331    0.3817 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8492    0.3514    0.1938 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4215   -0.2894   -1.1038 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9014   -0.3976   -1.2212 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2829   -1.4320   -0.3011 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9763   -1.7486   -0.9011 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9262   -1.4600   -2.2364 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8325   -1.6902   -3.0198 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4243   -0.8886   -2.5835 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3935    0.1438   -3.7159 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1792    1.4979   -3.3656 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6845    2.5765   -3.0653 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1951    3.8392   -2.6972 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1631    4.7594   -2.4148 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7379    6.1035   -2.2266 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1781    3.9955   -2.6454 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0244    2.9491   -2.9507 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5628    1.6991   -3.3125 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3397    3.2847   -2.8460 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2383    4.6591   -2.4393 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8785    5.1134   -2.3021 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3776   -0.4265    1.2332 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7630    0.1448    2.4534 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2525   -0.7750    3.3402 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6916   -0.3119    4.6090 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6075    1.5230    2.6198 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9574    2.1578    3.7858 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3870    5.5196    1.2820 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0341    4.5078   -0.0144 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3827    4.2053    0.6596 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2944    2.3277   -0.4288 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8231    0.3122   -1.9289 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8861   -1.2784   -1.2066 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4313    0.5648   -0.9836 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8723   -2.3524   -0.2244 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1117   -1.0360    0.7045 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0313   -1.7438   -2.9123 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4182    0.2854   -4.0844 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1653   -0.2552   -4.5728 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7631    2.4344   -3.1157 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1641    6.2067   -1.3004 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1813    6.4742   -3.0936 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6351    6.7220   -2.1244 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2674    0.9054   -3.5448 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7439    5.2855   -3.1832 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7468    4.7799   -1.4758 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4981   -1.5009    1.1037 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5313    0.3833    4.5108 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0557   -1.1801    5.1675 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8647    0.1171    5.1836 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7488    3.1006    3.6338 H   0  0  0  0  0  0  0  0  0  0  0  0
 29 26  2  0
  2  1  1  0
 10  9  1  0
 29 30  1  0
 26 25  1  0
 26 27  1  0
  9  8  1  0
 27 28  1  0
 25  5  2  0
 14 21  2  0
 21 20  1  0
  8  7  1  0
 19 16  1  0
  5  4  1  0
 16 15  2  0
 15 14  1  0
 19 20  2  0
  4  3  2  0
  7 12  1  0
  5  6  1  0
  6  7  1  0
 20 22  1  0
 22 23  1  0
 23 24  1  0
 24 19  1  0
 12 13  1  0
 16 17  1  0
  3 29  1  0
 17 18  1  0
 13 14  1  0
 10 11  2  0
 12 10  1  0
 12 40  1  6
  3  2  1  0
  7 37  1  1
  8 38  1  0
  8 39  1  0
 25 50  1  0
  4 34  1  0
  6 35  1  0
  6 36  1  0
 13 41  1  0
 13 42  1  0
  1 31  1  0
  1 32  1  0
  1 33  1  0
 30 54  1  0
 28 51  1  0
 28 52  1  0
 28 53  1  0
 21 47  1  0
 15 43  1  0
 23 48  1  0
 23 49  1  0
 18 44  1  0
 18 45  1  0
 18 46  1  0
M  END

HEADER    PROTEIN                                 19-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-JUN-21         0                                  
HETATM    1  C   UNK     0      -2.413   4.500   0.887  0.00  0.00           C+0
HETATM    2  O   UNK     0      -2.977   3.660   1.890  0.00  0.00           O+0
HETATM    3  C   UNK     0      -3.078   2.322   1.589  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.704   1.733   0.382  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.849   0.351   0.194  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.422  -0.289  -1.104  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.901  -0.398  -1.221  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.283  -1.432  -0.301  0.00  0.00           C+0
HETATM    9  O   UNK     0       0.976  -1.749  -0.901  0.00  0.00           O+0
HETATM   10  C   UNK     0       0.926  -1.460  -2.236  0.00  0.00           C+0
HETATM   11  O   UNK     0       1.833  -1.690  -3.020  0.00  0.00           O+0
HETATM   12  C   UNK     0      -0.424  -0.889  -2.583  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.394   0.144  -3.716  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.179   1.498  -3.366  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.685   2.576  -3.065  0.00  0.00           C+0
HETATM   16  C   UNK     0      -0.195   3.839  -2.697  0.00  0.00           C+0
HETATM   17  O   UNK     0      -1.163   4.759  -2.415  0.00  0.00           O+0
HETATM   18  C   UNK     0      -0.738   6.104  -2.227  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.178   3.995  -2.645  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.024   2.949  -2.951  0.00  0.00           C+0
HETATM   21  C   UNK     0       1.563   1.699  -3.313  0.00  0.00           C+0
HETATM   22  O   UNK     0       3.340   3.285  -2.846  0.00  0.00           O+0
HETATM   23  C   UNK     0       3.238   4.659  -2.439  0.00  0.00           C+0
HETATM   24  O   UNK     0       1.879   5.113  -2.302  0.00  0.00           O+0
HETATM   25  C   UNK     0      -3.378  -0.427   1.233  0.00  0.00           C+0
HETATM   26  C   UNK     0      -3.763   0.145   2.453  0.00  0.00           C+0
HETATM   27  O   UNK     0      -4.253  -0.775   3.340  0.00  0.00           O+0
HETATM   28  C   UNK     0      -4.692  -0.312   4.609  0.00  0.00           C+0
HETATM   29  C   UNK     0      -3.607   1.523   2.620  0.00  0.00           C+0
HETATM   30  O   UNK     0      -3.957   2.158   3.786  0.00  0.00           O+0
HETATM   31  H   UNK     0      -2.387   5.520   1.282  0.00  0.00           H+0
HETATM   32  H   UNK     0      -3.034   4.508  -0.014  0.00  0.00           H+0
HETATM   33  H   UNK     0      -1.383   4.205   0.660  0.00  0.00           H+0
HETATM   34  H   UNK     0      -2.294   2.328  -0.429  0.00  0.00           H+0
HETATM   35  H   UNK     0      -2.823   0.312  -1.929  0.00  0.00           H+0
HETATM   36  H   UNK     0      -2.886  -1.278  -1.207  0.00  0.00           H+0
HETATM   37  H   UNK     0      -0.431   0.565  -0.984  0.00  0.00           H+0
HETATM   38  H   UNK     0      -0.872  -2.352  -0.224  0.00  0.00           H+0
HETATM   39  H   UNK     0      -0.112  -1.036   0.705  0.00  0.00           H+0
HETATM   40  H   UNK     0      -1.031  -1.744  -2.912  0.00  0.00           H+0
HETATM   41  H   UNK     0      -1.418   0.285  -4.084  0.00  0.00           H+0
HETATM   42  H   UNK     0       0.165  -0.255  -4.573  0.00  0.00           H+0
HETATM   43  H   UNK     0      -1.763   2.434  -3.116  0.00  0.00           H+0
HETATM   44  H   UNK     0      -0.164   6.207  -1.300  0.00  0.00           H+0
HETATM   45  H   UNK     0      -0.181   6.474  -3.094  0.00  0.00           H+0
HETATM   46  H   UNK     0      -1.635   6.722  -2.124  0.00  0.00           H+0
HETATM   47  H   UNK     0       2.267   0.905  -3.545  0.00  0.00           H+0
HETATM   48  H   UNK     0       3.744   5.285  -3.183  0.00  0.00           H+0
HETATM   49  H   UNK     0       3.747   4.780  -1.476  0.00  0.00           H+0
HETATM   50  H   UNK     0      -3.498  -1.501   1.104  0.00  0.00           H+0
HETATM   51  H   UNK     0      -5.531   0.383   4.511  0.00  0.00           H+0
HETATM   52  H   UNK     0      -5.056  -1.180   5.168  0.00  0.00           H+0
HETATM   53  H   UNK     0      -3.865   0.117   5.184  0.00  0.00           H+0
HETATM   54  H   UNK     0      -3.749   3.101   3.634  0.00  0.00           H+0
CONECT    1    2   31   32   33                                             
CONECT    2    1    3                                                       
CONECT    3    4   29    2                                                  
CONECT    4    5    3   34                                                  
CONECT    5   25    4    6                                                  
CONECT    6    5    7   35   36                                             
CONECT    7    8   12    6   37                                             
CONECT    8    9    7   38   39                                             
CONECT    9   10    8                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12    7   13   10   40                                             
CONECT   13   12   14   41   42                                             
CONECT   14   21   15   13                                                  
CONECT   15   16   14   43                                                  
CONECT   16   19   15   17                                                  
CONECT   17   16   18                                                       
CONECT   18   17   44   45   46                                             
CONECT   19   16   20   24                                                  
CONECT   20   21   19   22                                                  
CONECT   21   14   20   47                                                  
CONECT   22   20   23                                                       
CONECT   23   22   24   48   49                                             
CONECT   24   23   19                                                       
CONECT   25   26    5   50                                                  
CONECT   26   29   25   27                                                  
CONECT   27   26   28                                                       
CONECT   28   27   51   52   53                                             
CONECT   29   26   30    3                                                  
CONECT   30   29   54                                                       
CONECT   31    1                                                            
CONECT   32    1                                                            
CONECT   33    1                                                            
CONECT   34    4                                                            
CONECT   35    6                                                            
CONECT   36    6                                                            
CONECT   37    7                                                            
CONECT   38    8                                                            
CONECT   39    8                                                            
CONECT   40   12                                                            
CONECT   41   13                                                            
CONECT   42   13                                                            
CONECT   43   15                                                            
CONECT   44   18                                                            
CONECT   45   18                                                            
CONECT   46   18                                                            
CONECT   47   21                                                            
CONECT   48   23                                                            
CONECT   49   23                                                            
CONECT   50   25                                                            
CONECT   51   28                                                            
CONECT   52   28                                                            
CONECT   53   28                                                            
CONECT   54   30                                                            
MASTER        0    0    0    0    0    0    0    0   54    0  114    0
END

RDKit          3D

54 57  0  0  0  0  0  0  0  0999 V2000
   -2.4127    4.4995    0.8870 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9769    3.6602    1.8902 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0778    2.3221    1.5890 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7038    1.7331    0.3817 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8492    0.3514    0.1938 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4215   -0.2894   -1.1038 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9014   -0.3976   -1.2212 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2829   -1.4320   -0.3011 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9763   -1.7486   -0.9011 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9262   -1.4600   -2.2364 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8325   -1.6902   -3.0198 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4243   -0.8886   -2.5835 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3935    0.1438   -3.7159 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1792    1.4979   -3.3656 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6845    2.5765   -3.0653 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1951    3.8392   -2.6972 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1631    4.7594   -2.4148 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7379    6.1035   -2.2266 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1781    3.9955   -2.6454 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0244    2.9491   -2.9507 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5628    1.6991   -3.3125 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3397    3.2847   -2.8460 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2383    4.6591   -2.4393 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8785    5.1134   -2.3021 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3776   -0.4265    1.2332 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7630    0.1448    2.4534 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2525   -0.7750    3.3402 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6916   -0.3119    4.6090 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6075    1.5230    2.6198 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9574    2.1578    3.7858 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3870    5.5196    1.2820 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0341    4.5078   -0.0144 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3827    4.2053    0.6596 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2944    2.3277   -0.4288 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8231    0.3122   -1.9289 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8861   -1.2784   -1.2066 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4313    0.5648   -0.9836 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8723   -2.3524   -0.2244 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1117   -1.0360    0.7045 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0313   -1.7438   -2.9123 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4182    0.2854   -4.0844 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1653   -0.2552   -4.5728 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7631    2.4344   -3.1157 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1641    6.2067   -1.3004 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1813    6.4742   -3.0936 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6351    6.7220   -2.1244 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2674    0.9054   -3.5448 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7439    5.2855   -3.1832 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7468    4.7799   -1.4758 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4981   -1.5009    1.1037 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5313    0.3833    4.5108 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0557   -1.1801    5.1675 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8647    0.1171    5.1836 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7488    3.1006    3.6338 H   0  0  0  0  0  0  0  0  0  0  0  0
 29 26  2  0
  2  1  1  0
 10  9  1  0
 29 30  1  0
 26 25  1  0
 26 27  1  0
  9  8  1  0
 27 28  1  0
 25  5  2  0
 14 21  2  0
 21 20  1  0
  8  7  1  0
 19 16  1  0
  5  4  1  0
 16 15  2  0
 15 14  1  0
 19 20  2  0
  4  3  2  0
  7 12  1  0
  5  6  1  0
  6  7  1  0
 20 22  1  0
 22 23  1  0
 23 24  1  0
 24 19  1  0
 12 13  1  0
 16 17  1  0
  3 29  1  0
 17 18  1  0
 13 14  1  0
 10 11  2  0
 12 10  1  0
 12 40  1  6
  3  2  1  0
  7 37  1  1
  8 38  1  0
  8 39  1  0
 25 50  1  0
  4 34  1  0
  6 35  1  0
  6 36  1  0
 13 41  1  0
 13 42  1  0
  1 31  1  0
  1 32  1  0
  1 33  1  0
 30 54  1  0
 28 51  1  0
 28 52  1  0
 28 53  1  0
 21 47  1  0
 15 43  1  0
 23 48  1  0
 23 49  1  0
 18 44  1  0
 18 45  1  0
 18 46  1  0
M  END

View in JSmol View DFT Assignments 3D Conformers

Synonyms

Not Available

Chemical Formula

C₂₂H₂₄O₈

Average Mass

416.4260 Da

Monoisotopic Mass

416.14712 Da

IUPAC Name

(3R,4R)-4-[(4-hydroxy-3,5-dimethoxyphenyl)methyl]-3-[(7-methoxy-2H-1,3-benzodioxol-5-yl)methyl]oxolan-2-one

Traditional Name

(3R,4R)-4-[(4-hydroxy-3,5-dimethoxyphenyl)methyl]-3-[(7-methoxy-2H-1,3-benzodioxol-5-yl)methyl]oxolan-2-one

CAS Registry Number

Not Available

SMILES

[H]OC1=C(OC([H])([H])[H])C([H])=C(C([H])=C1OC([H])([H])[H])C([H])([H])[C@@]1([H])C([H])([H])OC(=O)[C@]1([H])C([H])([H])C1=C([H])C2=C(OC([H])([H])O2)C(OC([H])([H])[H])=C1[H]

InChI Identifier

InChI=1S/C22H24O8/c1-25-16-6-12(7-17(26-2)20(16)23)4-14-10-28-22(24)15(14)5-13-8-18(27-3)21-19(9-13)29-11-30-21/h6-9,14-15,23H,4-5,10-11H2,1-3H3/t14-,15+/m0/s1

InChI Key

LSSNBHGWOAHIQS-LSDHHAIUSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 125 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 150 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 175 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 225 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 250 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Piper cubeba	JEOL database	Usia, T., et al, J. Nat. Prod. 68, 64 (2005)

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as dibenzylbutyrolactone lignans. These are lignan compounds containing a 3,4-dibenzyloxolan-2-one moiety.

Kingdom

Organic compounds

Super Class

Lignans, neolignans and related compounds

Class

Furanoid lignans

Sub Class

Tetrahydrofuran lignans

Direct Parent

Dibenzylbutyrolactone lignans

Alternative Parents

Substituents

Dibenzylbutyrolactone
Lignan lactone
Methoxyphenol
Dimethoxybenzene
M-dimethoxybenzene
Benzodioxole
Phenol ether
Anisole
Phenoxy compound
Methoxybenzene
Phenol
Alkyl aryl ether
Monocyclic benzene moiety
Benzenoid
Gamma butyrolactone
Oxolane
Lactone
Carboxylic acid ester
Acetal
Oxacycle
Carboxylic acid derivative
Organoheterocyclic compound
Ether
Monocarboxylic acid or derivatives
Carbonyl group
Organic oxide
Organooxygen compound
Hydrocarbon derivative
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

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

Predicted Properties

Property	Value	Source
logP	2.55	ALOGPS
logP	3.06	ChemAxon
logS	-4.3	ALOGPS
pKa (Strongest Acidic)	9.34	ChemAxon
pKa (Strongest Basic)	-4.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	92.68 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	105.88 m³·mol⁻¹	ChemAxon
Polarizability	42.29 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

Not Available

Chemspider ID

2282416

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

3013841

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Usia, T., et al. (2005). Usia, T., et al, J. Nat. Prod. 68, 64 (2005). J. Nat. Prod..

Showing NP-Card for (8R,8'R)-4-hydroxycubebinone (NP0027952)

MOL for NP0027952 ((8R,8'R)-4-hydroxycubebinone)

3D MOL for NP0027952 ((8R,8'R)-4-hydroxycubebinone)

3D SDF for NP0027952 ((8R,8'R)-4-hydroxycubebinone)

3D-SDF for NP0027952 ((8R,8'R)-4-hydroxycubebinone)

PDB for NP0027952 ((8R,8'R)-4-hydroxycubebinone)

3D PDB for NP0027952 ((8R,8'R)-4-hydroxycubebinone)

SMILES for NP0027952 ((8R,8'R)-4-hydroxycubebinone)

INCHI for NP0027952 ((8R,8'R)-4-hydroxycubebinone)

Structure for NP0027952 ((8R,8'R)-4-hydroxycubebinone)

3D Structure for NP0027952 ((8R,8'R)-4-hydroxycubebinone)