NP-MRD: Showing NP-Card for 1,2',3',8,10'-pentahydroxy-3,5',7'-trimethoxy-2',6-dimethyl-1',3'-dihydro-[2,9'-bianthracene]-4',9,10-trione (NP0197456)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-04 15:43:52 UTC

Updated at

2022-09-04 15:43:52 UTC

NP-MRD ID

NP0197456

Secondary Accession Numbers

None

Natural Product Identification

Common Name

1,2',3',8,10'-pentahydroxy-3,5',7'-trimethoxy-2',6-dimethyl-1',3'-dihydro-[2,9'-bianthracene]-4',9,10-trione

Description

1,2',3',8,10'-Pentahydroxy-3,5',7'-trimethoxy-2',6-dimethyl-1',2',3',4',9,10-hexahydro-[2,9'-bianthracene]-4',9,10-trione belongs to the class of organic compounds known as arylnaphthalene lignans. These are lignans containing the arylnaphthalene skeleton, especially 9-(2H-1,3-benzodioxol-5-yl)-1H,3H-naphtho[2,3-c]furan-1-one or a derivative thereof. Arylnaphthalene lignans occur in nature and exhibit diverse biological activities. 1,2',3',8,10'-pentahydroxy-3,5',7'-trimethoxy-2',6-dimethyl-1',3'-dihydro-[2,9'-bianthracene]-4',9,10-trione is found in Cortinarius sinapicolor. 1,2',3',8,10'-Pentahydroxy-3,5',7'-trimethoxy-2',6-dimethyl-1',2',3',4',9,10-hexahydro-[2,9'-bianthracene]-4',9,10-trione is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004231522132D          

 44 49  0  0  0  0            999 V2000
   -1.4289   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -5.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0993   -4.2683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5690   -3.3498    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  5  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
 16 19  1  0  0  0  0
 19 20  1  0  0  0  0
 11 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 23 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 26 28  1  0  0  0  0
 28 29  2  0  0  0  0
 29 30  1  0  0  0  0
 29 31  1  0  0  0  0
 31 32  2  0  0  0  0
 32 33  1  0  0  0  0
 32 34  1  0  0  0  0
 34 35  2  0  0  0  0
 28 35  1  0  0  0  0
 35 36  1  0  0  0  0
 36 37  2  0  0  0  0
 36 38  1  0  0  0  0
 25 38  2  0  0  0  0
 38 39  1  0  0  0  0
 39 40  2  0  0  0  0
 22 40  1  0  0  0  0
 40 41  1  0  0  0  0
 41 42  1  0  0  0  0
 21 43  1  0  0  0  0
  8 43  1  0  0  0  0
 43 44  2  0  0  0  0
  3 44  1  0  0  0  0
M  END

     RDKit          3D

 72 77  0  0  0  0  0  0  0  0999 V2000
   -2.1375   -3.8604   -4.3926 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8631   -2.9018   -3.4477 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4762   -2.1845   -2.5362 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8052   -2.2273   -2.1794 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4081   -1.4235   -1.1965 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6458   -1.5008   -0.8957 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8904   -1.7999   -0.8099 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5610   -0.5089   -0.5429 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1062    0.3515    0.4105 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4134    0.2967    0.7527 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2742    1.2984    1.0352 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9326    1.3817    0.7162 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4544    0.5069   -0.2260 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0434    0.4968   -0.5192 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5317    1.2429   -1.4830 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2509    2.0969   -2.3309 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3401    2.8694   -3.3356 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8983    1.2050   -1.6818 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6745    0.3885   -0.8776 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1124   -0.3922    0.1180 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7483   -0.3368    0.2967 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1157   -1.0893    1.2774 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9760   -1.2260    0.9437 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4755   -1.9389    1.8466 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4253   -1.2775    0.7758 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2149   -2.0581    1.6050 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7231   -2.8462    2.5887 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6177   -2.0561    1.4417 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1628   -1.2735    0.4535 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6736   -1.3051    0.3693 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3765   -0.5129   -0.3579 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9731   -0.4871   -0.2237 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1203    0.3439   -1.0541 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6335    1.0626   -1.9729 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2509   -0.4553   -0.8802 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6792   -1.2542   -1.8458 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1179    2.4030    1.4074 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4751    2.2323    2.9049 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4107    2.9505    3.6909 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4850    0.8622    3.2089 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8435    2.8385    3.0910 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.7520    4.2051    2.7496 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7548    2.2243    2.0515 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9647    2.5290    2.0685 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0328   -3.6321   -5.0278 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3467   -4.8786   -3.9507 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2650   -4.0263   -5.0940 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4152   -2.9404   -2.7222 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4681   -1.6326   -1.7652 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5247   -1.2234   -0.0471 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0316   -2.9070   -0.5392 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0340    0.7391    1.2781 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0502    2.2396   -3.9474 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4662    3.2062   -4.0521 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8033    3.7636   -2.9247 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3533    1.8042   -2.4621 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3475   -1.7030    1.9505 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8673   -3.0733    2.9552 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2032   -2.6606    2.1005 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.0192   -0.8517    1.3079 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.9566   -0.6589   -0.4716 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.0076   -2.3704    0.2704 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8048    0.0945   -1.1287 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6270   -1.1453   -2.0556 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4849    3.4404    1.2025 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0492    2.2978    1.3688 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7847    3.5253    4.5550 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1599    3.6122    3.0072 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3265    2.1716    4.0131 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3644    0.7616    4.2048 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2719    2.6971    4.0973 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5305    4.4808    2.1924 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  5  8  2  0
  8  9  1  0
  9 10  1  0
  9 11  2  0
 11 43  1  0
 43 44  2  0
 43 41  1  0
 41 42  1  0
 41 38  1  0
 38 39  1  0
 38 40  1  1
 38 37  1  0
 37 12  1  0
 12 13  2  0
 13 35  1  0
 35 36  2  0
 13 14  1  0
 14 21  2  0
 21 22  1  0
 21 20  1  0
 20 19  2  0
 19 18  1  0
 18 15  2  0
 15 16  1  0
 16 17  1  0
 19 33  1  0
 33 34  2  0
 33 32  1  0
 32 31  2  0
 31 29  1  0
 29 30  1  0
 29 28  2  0
 28 26  1  0
 26 27  1  0
 26 25  2  0
 25 23  1  0
 23 24  2  0
 36  3  1  0
 15 14  1  0
 25 32  1  0
 35  8  1  0
 23 20  1  0
 12 11  1  0
  1 45  1  0
  1 46  1  0
  1 47  1  0
  4 48  1  0
  7 49  1  0
  7 50  1  0
  7 51  1  0
 10 52  1  0
 41 71  1  1
 42 72  1  0
 39 67  1  0
 39 68  1  0
 39 69  1  0
 40 70  1  0
 37 65  1  0
 37 66  1  0
 36 64  1  0
 22 57  1  0
 18 56  1  0
 17 53  1  0
 17 54  1  0
 17 55  1  0
 31 63  1  0
 30 60  1  0
 30 61  1  0
 30 62  1  0
 28 59  1  0
 27 58  1  0
M  END


  Mrv1533004231522132D          

 44 49  0  0  0  0            999 V2000
   -1.4289   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -5.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0993   -4.2683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5690   -3.3498    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  5  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
 16 19  1  0  0  0  0
 19 20  1  0  0  0  0
 11 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 23 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 26 28  1  0  0  0  0
 28 29  2  0  0  0  0
 29 30  1  0  0  0  0
 29 31  1  0  0  0  0
 31 32  2  0  0  0  0
 32 33  1  0  0  0  0
 32 34  1  0  0  0  0
 34 35  2  0  0  0  0
 28 35  1  0  0  0  0
 35 36  1  0  0  0  0
 36 37  2  0  0  0  0
 36 38  1  0  0  0  0
 25 38  2  0  0  0  0
 38 39  1  0  0  0  0
 39 40  2  0  0  0  0
 22 40  1  0  0  0  0
 40 41  1  0  0  0  0
 41 42  1  0  0  0  0
 21 43  1  0  0  0  0
  8 43  1  0  0  0  0
 43 44  2  0  0  0  0
  3 44  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0197456

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(OC)=C2C(O)=C3C(=O)C(O)C(C)(O)CC3=C(C2=C1)C1=C(O)C2=C(C=C1OC)C(=O)C1=CC(C)=CC(O)=C1C2=O

> <INCHI_IDENTIFIER>
InChI=1S/C33H28O11/c1-12-6-15-22(18(34)7-12)28(36)24-16(27(15)35)10-20(44-5)26(30(24)38)21-14-8-13(42-3)9-19(43-4)23(14)29(37)25-17(21)11-33(2,41)32(40)31(25)39/h6-10,32,34,37-38,40-41H,11H2,1-5H3

> <INCHI_KEY>
FWOHGTUCKDNPLQ-UHFFFAOYSA-N

> <FORMULA>
C33H28O11

> <MOLECULAR_WEIGHT>
600.576

> <EXACT_MASS>
600.163161722

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_ATOM_COUNT>
72

> <JCHEM_AVERAGE_POLARIZABILITY>
61.55084346004138

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
1,8-dihydroxy-3-methoxy-6-methyl-2-(2,3,10-trihydroxy-5,7-dimethoxy-2-methyl-4-oxo-1,2,3,4-tetrahydroanthracen-9-yl)-9,10-dihydroanthracene-9,10-dione

> <ALOGPS_LOGP>
3.48

> <JCHEM_LOGP>
5.277605813666667

> <ALOGPS_LOGS>
-4.72

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
7.918419550910016

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.057201557237978

> <JCHEM_PKA_STRONGEST_BASIC>
-3.379298214866246

> <JCHEM_POLAR_SURFACE_AREA>
180.04999999999998

> <JCHEM_REFRACTIVITY>
158.87149999999994

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.14e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1,8-dihydroxy-3-methoxy-6-methyl-2-(2,3,10-trihydroxy-5,7-dimethoxy-2-methyl-4-oxo-1,3-dihydroanthracen-9-yl)anthracene-9,10-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 23-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-APR-15         0                                  
HETATM    1  C   UNK     0      -2.667  -7.700   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -1.334  -6.930   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       0.000  -7.700   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000  -9.240   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334 -10.010   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       1.334 -11.550   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       2.667 -12.320   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.667  -9.240   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.001 -10.010   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       4.001 -11.550   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       5.335  -9.240   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.668 -10.010   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       6.668 -11.550   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       8.002  -9.240   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       9.336 -10.010   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       8.002  -7.700   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       9.519  -7.967   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       8.529  -6.253   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       6.668  -6.930   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.335  -7.700   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       1.334  -5.390   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       0.000  -3.080   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      -1.334  -0.770   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0       5.335  -0.000   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   41  O   UNK     0       6.668  -5.390   0.000  0.00  0.00           O+0
HETATM   42  C   UNK     0       8.002  -4.620   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0       2.667  -7.700   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   44                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    8                                                  
CONECT    6    5    7                                                       
CONECT    7    6                                                            
CONECT    8    5    9   43                                                  
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   20                                                  
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17   18   19                                             
CONECT   17   16                                                            
CONECT   18   16                                                            
CONECT   19   16   20                                                       
CONECT   20   19   11   21                                                  
CONECT   21   20   22   43                                                  
CONECT   22   21   23   40                                                  
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26   38                                                  
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   29   35                                                  
CONECT   29   28   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   32                                                       
CONECT   32   31   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32   35                                                       
CONECT   35   34   28   36                                                  
CONECT   36   35   37   38                                                  
CONECT   37   36                                                            
CONECT   38   36   25   39                                                  
CONECT   39   38   40                                                       
CONECT   40   39   22   41                                                  
CONECT   41   40   42                                                       
CONECT   42   41                                                            
CONECT   43   21    8   44                                                  
CONECT   44   43    3                                                       
MASTER        0    0    0    0    0    0    0    0   44    0   98    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₃H₂₈O₁₁

Average Mass

600.5760 Da

Monoisotopic Mass

600.16316 Da

IUPAC Name

1,8-dihydroxy-3-methoxy-6-methyl-2-(2,3,10-trihydroxy-5,7-dimethoxy-2-methyl-4-oxo-1,2,3,4-tetrahydroanthracen-9-yl)-9,10-dihydroanthracene-9,10-dione

Traditional Name

1,8-dihydroxy-3-methoxy-6-methyl-2-(2,3,10-trihydroxy-5,7-dimethoxy-2-methyl-4-oxo-1,3-dihydroanthracen-9-yl)anthracene-9,10-dione

CAS Registry Number

Not Available

SMILES

COC1=CC(OC)=C2C(O)=C3C(=O)C(O)C(C)(O)CC3=C(C2=C1)C1=C(O)C2=C(C=C1OC)C(=O)C1=CC(C)=CC(O)=C1C2=O

InChI Identifier

InChI=1S/C33H28O11/c1-12-6-15-22(18(34)7-12)28(36)24-16(27(15)35)10-20(44-5)26(30(24)38)21-14-8-13(42-3)9-19(43-4)23(14)29(37)25-17(21)11-33(2,41)32(40)31(25)39/h6-10,32,34,37-38,40-41H,11H2,1-5H3

InChI Key

FWOHGTUCKDNPLQ-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, 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
Cortinarius sinapicolor	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as arylnaphthalene lignans. These are lignans containing the arylnaphthalene skeleton, especially 9-(2H-1,3-benzodioxol-5-yl)-1H,3H-naphtho[2,3-c]furan-1-one or a derivative thereof. Arylnaphthalene lignans occur in nature and exhibit diverse biological activities.

Kingdom

Organic compounds

Super Class

Lignans, neolignans and related compounds

Class

Arylnaphthalene lignans

Sub Class

Not Available

Direct Parent

Arylnaphthalene lignans

Alternative Parents

Substituents

Arylnaphthalene lignan skeleton
9,10-anthraquinone
Anthraquinone
Anthracene
1-naphthol
Tetralin
Anisole
Aryl ketone
Aryl alkyl ketone
Alkyl aryl ether
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Benzenoid
Vinylogous acid
Tertiary alcohol
Secondary alcohol
Ketone
1,2-diol
Polyol
Ether
Organooxygen compound
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Alcohol
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	3.48	ALOGPS
logP	5.28	ChemAxon
logS	-4.7	ALOGPS
pKa (Strongest Acidic)	7.06	ChemAxon
pKa (Strongest Basic)	-3.4	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	180.05 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	158.87 m³·mol⁻¹	ChemAxon
Polarizability	61.55 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	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

Not Available

METLIN ID

Not Available

PubChem Compound

85193080

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 1,2',3',8,10'-pentahydroxy-3,5',7'-trimethoxy-2',6-dimethyl-1',3'-dihydro-[2,9'-bianthracene]-4',9,10-trione (NP0197456)

MOL for NP0197456 (1,2',3',8,10'-pentahydroxy-3,5',7'-trimethoxy-2',6-dimethyl-1',3'-dihydro-[2,9'-bianthracene]-4',9,10-trione)

3D MOL for NP0197456 (1,2',3',8,10'-pentahydroxy-3,5',7'-trimethoxy-2',6-dimethyl-1',3'-dihydro-[2,9'-bianthracene]-4',9,10-trione)

3D SDF for NP0197456 (1,2',3',8,10'-pentahydroxy-3,5',7'-trimethoxy-2',6-dimethyl-1',3'-dihydro-[2,9'-bianthracene]-4',9,10-trione)

3D-SDF for NP0197456 (1,2',3',8,10'-pentahydroxy-3,5',7'-trimethoxy-2',6-dimethyl-1',3'-dihydro-[2,9'-bianthracene]-4',9,10-trione)

PDB for NP0197456 (1,2',3',8,10'-pentahydroxy-3,5',7'-trimethoxy-2',6-dimethyl-1',3'-dihydro-[2,9'-bianthracene]-4',9,10-trione)

3D PDB for NP0197456 (1,2',3',8,10'-pentahydroxy-3,5',7'-trimethoxy-2',6-dimethyl-1',3'-dihydro-[2,9'-bianthracene]-4',9,10-trione)

SMILES for NP0197456 (1,2',3',8,10'-pentahydroxy-3,5',7'-trimethoxy-2',6-dimethyl-1',3'-dihydro-[2,9'-bianthracene]-4',9,10-trione)

INCHI for NP0197456 (1,2',3',8,10'-pentahydroxy-3,5',7'-trimethoxy-2',6-dimethyl-1',3'-dihydro-[2,9'-bianthracene]-4',9,10-trione)

Structure for NP0197456 (1,2',3',8,10'-pentahydroxy-3,5',7'-trimethoxy-2',6-dimethyl-1',3'-dihydro-[2,9'-bianthracene]-4',9,10-trione)

3D Structure for NP0197456 (1,2',3',8,10'-pentahydroxy-3,5',7'-trimethoxy-2',6-dimethyl-1',3'-dihydro-[2,9'-bianthracene]-4',9,10-trione)