NP-MRD: Showing NP-Card for (-)-8'-epi-8-hydroxy-aristoligone (NP0032010)

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Record Information

Version

2.0

Created at

2021-06-19 22:55:53 UTC

Updated at

2021-06-30 00:00:57 UTC

NP-MRD ID

NP0032010

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(-)-8'-epi-8-hydroxy-aristoligone

Provided By

JEOL Database JEOL Logo

Description

(?)-8'-Epi-8-Hydroxyaristoligone belongs to the class of organic compounds known as aryltetralin lignans. These are lignans with a structure based on the 1-phenyltetralin skeleton. (-)-8'-epi-8-hydroxy-aristoligone is found in Aristolochia holostylis and Holostylis reniformis. (-)-8'-epi-8-hydroxy-aristoligone was first documented in 2006 (Silva, T., et al.). Based on a literature review very few articles have been published on (?)-8'-Epi-8-Hydroxyaristoligone.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306202100553D          

 54 56  0  0  0  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652306202100553D          

 54 56  0  0  0  0            999 V2000
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   -4.7981   -4.5716   -2.8961 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8993   -0.7778   -2.0344 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1601   -1.8634   -3.4043 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9377   -0.5961   -3.5549 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8969    0.3605   -1.6869 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6605    2.2269    2.2782 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9676    0.6135    2.4523 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1081    2.0447    3.0674 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5662    3.6508    0.3723 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2953    1.3789   -0.2554 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0727    1.1422    2.7685 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3277    1.0871    1.5248 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4533    2.5839    1.8104 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3779   -0.4638   -1.7199 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3076   -0.8223   -1.9900 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9501   -0.6925   -3.7148 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3231   -2.2833   -3.0526 H   0  0  0  0  0  0  0  0  0  0  0  0
  9  8  2  0  0  0  0
 14 15  1  0  0  0  0
 13 10  2  0  0  0  0
 11 12  1  0  0  0  0
 17 16  2  0  0  0  0
 23 24  1  0  0  0  0
 16 13  1  0  0  0  0
  7  6  1  0  0  0  0
 17 18  1  0  0  0  0
 20 21  1  0  0  0  0
  8  7  1  0  0  0  0
  6  5  2  0  0  0  0
  7 23  1  0  0  0  0
  5  4  1  0  0  0  0
 23 20  1  0  0  0  0
  4  3  2  0  0  0  0
 20 18  1  0  0  0  0
  3 26  1  0  0  0  0
 17  8  1  0  0  0  0
 26 25  2  0  0  0  0
 25  6  1  0  0  0  0
 18 19  2  0  0  0  0
  3  2  1  0  0  0  0
 26 27  1  0  0  0  0
 13 14  1  0  0  0  0
 27 28  1  0  0  0  0
 10  9  1  0  0  0  0
  2  1  1  0  0  0  0
 10 11  1  0  0  0  0
 20 22  1  6  0  0  0
  9 35  1  0  0  0  0
 16 42  1  0  0  0  0
  7 34  1  1  0  0  0
 23 47  1  6  0  0  0
 15 39  1  0  0  0  0
 15 40  1  0  0  0  0
 15 41  1  0  0  0  0
 12 36  1  0  0  0  0
 12 37  1  0  0  0  0
 12 38  1  0  0  0  0
 24 48  1  0  0  0  0
 24 49  1  0  0  0  0
 24 50  1  0  0  0  0
 21 43  1  0  0  0  0
 21 44  1  0  0  0  0
 21 45  1  0  0  0  0
  5 33  1  0  0  0  0
  4 32  1  0  0  0  0
 25 51  1  0  0  0  0
 28 52  1  0  0  0  0
 28 53  1  0  0  0  0
 28 54  1  0  0  0  0
  1 29  1  0  0  0  0
  1 30  1  0  0  0  0
  1 31  1  0  0  0  0
 22 46  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0032010

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C22H26O6/c1-12-20(13-7-8-16(25-3)17(9-13)26-4)14-10-18(27-5)19(28-6)11-15(14)21(23)22(12,2)24/h7-12,20,24H,1-6H3/t12-,20+,22+/m0/s1

> <INCHI_KEY>
JSKWJJGGQAJPOM-IPLWYIACSA-N

> <FORMULA>
C22H26O6

> <MOLECULAR_WEIGHT>
386.444

> <EXACT_MASS>
386.172938557

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
54

> <JCHEM_AVERAGE_POLARIZABILITY>
42.09594692633411

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2R,3S,4R)-4-(3,4-dimethoxyphenyl)-2-hydroxy-6,7-dimethoxy-2,3-dimethyl-1,2,3,4-tetrahydronaphthalen-1-one

> <ALOGPS_LOGP>
3.28

> <JCHEM_LOGP>
2.997935466333332

> <ALOGPS_LOGS>
-4.79

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.957683101016606

> <JCHEM_PKA_STRONGEST_BASIC>
-3.692109411615336

> <JCHEM_POLAR_SURFACE_AREA>
74.22000000000001

> <JCHEM_REFRACTIVITY>
105.5002

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.34e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2R,3S,4R)-4-(3,4-dimethoxyphenyl)-2-hydroxy-6,7-dimethoxy-2,3-dimethyl-3,4-dihydronaphthalen-1-one

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 54 56  0  0  0  0  0  0  0  0999 V2000
    4.3814   -4.2277    0.0234 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8138   -3.2582   -0.8471 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7062   -2.5798   -0.4132 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1805   -2.6899    0.8796 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0162   -2.0032    1.2437 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3447   -1.1927    0.3205 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9368   -0.4612    0.7257 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1433   -0.8901   -0.1078 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3609   -2.2495   -0.3926 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4418   -2.6719   -1.1780 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5118   -4.0304   -1.3594 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7298   -4.4264   -2.7117 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3780   -1.7441   -1.6564 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4440   -2.2328   -2.3621 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3985   -1.3012   -2.8554 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1898   -0.3935   -1.3523 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0939    0.0249   -0.5762 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9974    1.4603   -0.2217 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7108    2.2975   -0.7741 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0294    1.8485    0.8958 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.7221    1.6594    2.2467 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7583    3.2521    0.7575 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7069    1.0783    0.7200 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3416    1.4958    1.7680 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8765   -1.0776   -0.9722 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0566   -1.7409   -1.3335 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4334   -1.5318   -2.6370 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8297   -1.3318   -2.8345 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2031   -4.7148   -0.5104 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8011   -3.7548    0.9172 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6524   -5.0009    0.2876 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6507   -3.3111    1.6351 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6369   -2.1170    2.2574 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1821   -0.7569    1.7561 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6725   -3.0084   -0.0227 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2996   -3.7237   -3.4346 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2372   -5.3930   -2.8565 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7981   -4.5716   -2.8961 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8993   -0.7778   -2.0344 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1601   -1.8634   -3.4043 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9377   -0.5961   -3.5549 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8969    0.3605   -1.6869 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6605    2.2269    2.2782 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9676    0.6135    2.4523 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1081    2.0447    3.0674 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5662    3.6508    0.3723 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2953    1.3789   -0.2554 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0727    1.1422    2.7685 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3277    1.0871    1.5248 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4533    2.5839    1.8104 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3779   -0.4638   -1.7199 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3076   -0.8223   -1.9900 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9501   -0.6925   -3.7148 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3231   -2.2833   -3.0526 H   0  0  0  0  0  0  0  0  0  0  0  0
  9  8  2  0
 14 15  1  0
 13 10  2  0
 11 12  1  0
 17 16  2  0
 23 24  1  0
 16 13  1  0
  7  6  1  0
 17 18  1  0
 20 21  1  0
  8  7  1  0
  6  5  2  0
  7 23  1  0
  5  4  1  0
 23 20  1  0
  4  3  2  0
 20 18  1  0
  3 26  1  0
 17  8  1  0
 26 25  2  0
 25  6  1  0
 18 19  2  0
  3  2  1  0
 26 27  1  0
 13 14  1  0
 27 28  1  0
 10  9  1  0
  2  1  1  0
 10 11  1  0
 20 22  1  6
  9 35  1  0
 16 42  1  0
  7 34  1  1
 23 47  1  6
 15 39  1  0
 15 40  1  0
 15 41  1  0
 12 36  1  0
 12 37  1  0
 12 38  1  0
 24 48  1  0
 24 49  1  0
 24 50  1  0
 21 43  1  0
 21 44  1  0
 21 45  1  0
  5 33  1  0
  4 32  1  0
 25 51  1  0
 28 52  1  0
 28 53  1  0
 28 54  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
 22 46  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       4.381  -4.228   0.023  0.00  0.00           C+0
HETATM    2  O   UNK     0       3.814  -3.258  -0.847  0.00  0.00           O+0
HETATM    3  C   UNK     0       2.706  -2.580  -0.413  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.180  -2.690   0.880  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.016  -2.003   1.244  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.345  -1.193   0.321  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.937  -0.461   0.726  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.143  -0.890  -0.108  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.361  -2.249  -0.393  0.00  0.00           C+0
HETATM   10  C   UNK     0      -3.442  -2.672  -1.178  0.00  0.00           C+0
HETATM   11  O   UNK     0      -3.512  -4.030  -1.359  0.00  0.00           O+0
HETATM   12  C   UNK     0      -3.730  -4.426  -2.712  0.00  0.00           C+0
HETATM   13  C   UNK     0      -4.378  -1.744  -1.656  0.00  0.00           C+0
HETATM   14  O   UNK     0      -5.444  -2.233  -2.362  0.00  0.00           O+0
HETATM   15  C   UNK     0      -6.399  -1.301  -2.855  0.00  0.00           C+0
HETATM   16  C   UNK     0      -4.190  -0.394  -1.352  0.00  0.00           C+0
HETATM   17  C   UNK     0      -3.094   0.025  -0.576  0.00  0.00           C+0
HETATM   18  C   UNK     0      -2.997   1.460  -0.222  0.00  0.00           C+0
HETATM   19  O   UNK     0      -3.711   2.297  -0.774  0.00  0.00           O+0
HETATM   20  C   UNK     0      -2.029   1.849   0.896  0.00  0.00           C+0
HETATM   21  C   UNK     0      -2.722   1.659   2.247  0.00  0.00           C+0
HETATM   22  O   UNK     0      -1.758   3.252   0.758  0.00  0.00           O+0
HETATM   23  C   UNK     0      -0.707   1.078   0.720  0.00  0.00           C+0
HETATM   24  C   UNK     0       0.342   1.496   1.768  0.00  0.00           C+0
HETATM   25  C   UNK     0       0.877  -1.078  -0.972  0.00  0.00           C+0
HETATM   26  C   UNK     0       2.057  -1.741  -1.333  0.00  0.00           C+0
HETATM   27  O   UNK     0       2.433  -1.532  -2.637  0.00  0.00           O+0
HETATM   28  C   UNK     0       3.830  -1.332  -2.834  0.00  0.00           C+0
HETATM   29  H   UNK     0       5.203  -4.715  -0.510  0.00  0.00           H+0
HETATM   30  H   UNK     0       4.801  -3.755   0.917  0.00  0.00           H+0
HETATM   31  H   UNK     0       3.652  -5.001   0.288  0.00  0.00           H+0
HETATM   32  H   UNK     0       2.651  -3.311   1.635  0.00  0.00           H+0
HETATM   33  H   UNK     0       0.637  -2.117   2.257  0.00  0.00           H+0
HETATM   34  H   UNK     0      -1.182  -0.757   1.756  0.00  0.00           H+0
HETATM   35  H   UNK     0      -1.673  -3.008  -0.023  0.00  0.00           H+0
HETATM   36  H   UNK     0      -3.300  -3.724  -3.435  0.00  0.00           H+0
HETATM   37  H   UNK     0      -3.237  -5.393  -2.857  0.00  0.00           H+0
HETATM   38  H   UNK     0      -4.798  -4.572  -2.896  0.00  0.00           H+0
HETATM   39  H   UNK     0      -6.899  -0.778  -2.034  0.00  0.00           H+0
HETATM   40  H   UNK     0      -7.160  -1.863  -3.404  0.00  0.00           H+0
HETATM   41  H   UNK     0      -5.938  -0.596  -3.555  0.00  0.00           H+0
HETATM   42  H   UNK     0      -4.897   0.361  -1.687  0.00  0.00           H+0
HETATM   43  H   UNK     0      -3.660   2.227   2.278  0.00  0.00           H+0
HETATM   44  H   UNK     0      -2.968   0.614   2.452  0.00  0.00           H+0
HETATM   45  H   UNK     0      -2.108   2.045   3.067  0.00  0.00           H+0
HETATM   46  H   UNK     0      -2.566   3.651   0.372  0.00  0.00           H+0
HETATM   47  H   UNK     0      -0.295   1.379  -0.255  0.00  0.00           H+0
HETATM   48  H   UNK     0       0.073   1.142   2.769  0.00  0.00           H+0
HETATM   49  H   UNK     0       1.328   1.087   1.525  0.00  0.00           H+0
HETATM   50  H   UNK     0       0.453   2.584   1.810  0.00  0.00           H+0
HETATM   51  H   UNK     0       0.378  -0.464  -1.720  0.00  0.00           H+0
HETATM   52  H   UNK     0       4.308  -0.822  -1.990  0.00  0.00           H+0
HETATM   53  H   UNK     0       3.950  -0.693  -3.715  0.00  0.00           H+0
HETATM   54  H   UNK     0       4.323  -2.283  -3.053  0.00  0.00           H+0
CONECT    1    2   29   30   31                                             
CONECT    2    3    1                                                       
CONECT    3    4   26    2                                                  
CONECT    4    5    3   32                                                  
CONECT    5    6    4   33                                                  
CONECT    6    7    5   25                                                  
CONECT    7    6    8   23   34                                             
CONECT    8    9    7   17                                                  
CONECT    9    8   10   35                                                  
CONECT   10   13    9   11                                                  
CONECT   11   12   10                                                       
CONECT   12   11   36   37   38                                             
CONECT   13   10   16   14                                                  
CONECT   14   15   13                                                       
CONECT   15   14   39   40   41                                             
CONECT   16   17   13   42                                                  
CONECT   17   16   18    8                                                  
CONECT   18   17   20   19                                                  
CONECT   19   18                                                            
CONECT   20   21   23   18   22                                             
CONECT   21   20   43   44   45                                             
CONECT   22   20   46                                                       
CONECT   23   24    7   20   47                                             
CONECT   24   23   48   49   50                                             
CONECT   25   26    6   51                                                  
CONECT   26    3   25   27                                                  
CONECT   27   26   28                                                       
CONECT   28   27   52   53   54                                             
CONECT   29    1                                                            
CONECT   30    1                                                            
CONECT   31    1                                                            
CONECT   32    4                                                            
CONECT   33    5                                                            
CONECT   34    7                                                            
CONECT   35    9                                                            
CONECT   36   12                                                            
CONECT   37   12                                                            
CONECT   38   12                                                            
CONECT   39   15                                                            
CONECT   40   15                                                            
CONECT   41   15                                                            
CONECT   42   16                                                            
CONECT   43   21                                                            
CONECT   44   21                                                            
CONECT   45   21                                                            
CONECT   46   22                                                            
CONECT   47   23                                                            
CONECT   48   24                                                            
CONECT   49   24                                                            
CONECT   50   24                                                            
CONECT   51   25                                                            
CONECT   52   28                                                            
CONECT   53   28                                                            
CONECT   54   28                                                            
MASTER        0    0    0    0    0    0    0    0   54    0  112    0
END

RDKit          3D

54 56  0  0  0  0  0  0  0  0999 V2000
    4.3814   -4.2277    0.0234 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8138   -3.2582   -0.8471 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7062   -2.5798   -0.4132 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1805   -2.6899    0.8796 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0162   -2.0032    1.2437 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3447   -1.1927    0.3205 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9368   -0.4612    0.7257 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1433   -0.8901   -0.1078 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3609   -2.2495   -0.3926 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4418   -2.6719   -1.1780 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5118   -4.0304   -1.3594 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7298   -4.4264   -2.7117 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3780   -1.7441   -1.6564 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4440   -2.2328   -2.3621 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3985   -1.3012   -2.8554 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1898   -0.3935   -1.3523 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0939    0.0249   -0.5762 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9974    1.4603   -0.2217 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7108    2.2975   -0.7741 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0294    1.8485    0.8958 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.7221    1.6594    2.2467 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7583    3.2521    0.7575 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7069    1.0783    0.7200 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3416    1.4958    1.7680 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8765   -1.0776   -0.9722 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0566   -1.7409   -1.3335 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4334   -1.5318   -2.6370 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8297   -1.3318   -2.8345 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2031   -4.7148   -0.5104 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8011   -3.7548    0.9172 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6524   -5.0009    0.2876 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6507   -3.3111    1.6351 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6369   -2.1170    2.2574 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1821   -0.7569    1.7561 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6725   -3.0084   -0.0227 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2996   -3.7237   -3.4346 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2372   -5.3930   -2.8565 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7981   -4.5716   -2.8961 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8993   -0.7778   -2.0344 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1601   -1.8634   -3.4043 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9377   -0.5961   -3.5549 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8969    0.3605   -1.6869 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6605    2.2269    2.2782 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9676    0.6135    2.4523 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1081    2.0447    3.0674 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5662    3.6508    0.3723 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2953    1.3789   -0.2554 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0727    1.1422    2.7685 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3277    1.0871    1.5248 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4533    2.5839    1.8104 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3779   -0.4638   -1.7199 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3076   -0.8223   -1.9900 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9501   -0.6925   -3.7148 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3231   -2.2833   -3.0526 H   0  0  0  0  0  0  0  0  0  0  0  0
  9  8  2  0
 14 15  1  0
 13 10  2  0
 11 12  1  0
 17 16  2  0
 23 24  1  0
 16 13  1  0
  7  6  1  0
 17 18  1  0
 20 21  1  0
  8  7  1  0
  6  5  2  0
  7 23  1  0
  5  4  1  0
 23 20  1  0
  4  3  2  0
 20 18  1  0
  3 26  1  0
 17  8  1  0
 26 25  2  0
 25  6  1  0
 18 19  2  0
  3  2  1  0
 26 27  1  0
 13 14  1  0
 27 28  1  0
 10  9  1  0
  2  1  1  0
 10 11  1  0
 20 22  1  6
  9 35  1  0
 16 42  1  0
  7 34  1  1
 23 47  1  6
 15 39  1  0
 15 40  1  0
 15 41  1  0
 12 36  1  0
 12 37  1  0
 12 38  1  0
 24 48  1  0
 24 49  1  0
 24 50  1  0
 21 43  1  0
 21 44  1  0
 21 45  1  0
  5 33  1  0
  4 32  1  0
 25 51  1  0
 28 52  1  0
 28 53  1  0
 28 54  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
 22 46  1  0
M  END

View in JSmol View DFT Assignments 3D Conformers

Synonyms

Not Available

Chemical Formula

C₂₂H₂₆O₆

Average Mass

386.4440 Da

Monoisotopic Mass

386.17294 Da

IUPAC Name

(2R,3S,4R)-4-(3,4-dimethoxyphenyl)-2-hydroxy-6,7-dimethoxy-2,3-dimethyl-1,2,3,4-tetrahydronaphthalen-1-one

Traditional Name

(2R,3S,4R)-4-(3,4-dimethoxyphenyl)-2-hydroxy-6,7-dimethoxy-2,3-dimethyl-3,4-dihydronaphthalen-1-one

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C22H26O6/c1-12-20(13-7-8-16(25-3)17(9-13)26-4)14-10-18(27-5)19(28-6)11-15(14)21(23)22(12,2)24/h7-12,20,24H,1-6H3/t12-,20+,22+/m0/s1

InChI Key

JSKWJJGGQAJPOM-IPLWYIACSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
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, 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, 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, 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
Aristolochia holostylis	LOTUS Database	35616633
Holostylis reniformis	JEOL database	Silva, T., et al, Phytochemistry 67, 929 (2006)

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as aryltetralin lignans. These are lignans with a structure based on the 1-phenyltetralin skeleton.

Kingdom

Organic compounds

Super Class

Lignans, neolignans and related compounds

Class

Aryltetralin lignans

Sub Class

Not Available

Direct Parent

Aryltetralin lignans

Alternative Parents

Substituents

1-aryltetralin lignan
Tetralin
Dimethoxybenzene
O-dimethoxybenzene
Methoxybenzene
Anisole
Aryl alkyl ketone
Aryl ketone
Phenol ether
Phenoxy compound
Alkyl aryl ether
Monocyclic benzene moiety
Benzenoid
Acyloin
Tertiary alcohol
Ketone
Ether
Organooxygen compound
Organic oxygen compound
Alcohol
Organic oxide
Hydrocarbon derivative
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic 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	3.28	ALOGPS
logP	3	ChemAxon
logS	-4.8	ALOGPS
pKa (Strongest Acidic)	12.96	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	74.22 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	105.5 m³·mol⁻¹	ChemAxon
Polarizability	42.1 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	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Bracket

METLIN ID

Not Available

PubChem Compound

102180985

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Silva, T., et al. (2006). Silva, T., et al, Phytochemistry 67, 929 (2006). Phytochem..

Showing NP-Card for (-)-8'-epi-8-hydroxy-aristoligone (NP0032010)

MOL for NP0032010 ((-)-8'-epi-8-hydroxy-aristoligone)

3D MOL for NP0032010 ((-)-8'-epi-8-hydroxy-aristoligone)

3D SDF for NP0032010 ((-)-8'-epi-8-hydroxy-aristoligone)

3D-SDF for NP0032010 ((-)-8'-epi-8-hydroxy-aristoligone)

PDB for NP0032010 ((-)-8'-epi-8-hydroxy-aristoligone)

3D PDB for NP0032010 ((-)-8'-epi-8-hydroxy-aristoligone)

SMILES for NP0032010 ((-)-8'-epi-8-hydroxy-aristoligone)

INCHI for NP0032010 ((-)-8'-epi-8-hydroxy-aristoligone)

Structure for NP0032010 ((-)-8'-epi-8-hydroxy-aristoligone)

3D Structure for NP0032010 ((-)-8'-epi-8-hydroxy-aristoligone)