NP-MRD: Showing NP-Card for (-)-4',6'-Diacetylviburnolide A (NP0074991)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-04-28 20:18:24 UTC

Updated at

2022-04-28 20:18:24 UTC

NP-MRD ID

NP0074991

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(-)-4',6'-Diacetylviburnolide A

Description

[(2R,3R,4R,5R,6S)-6-[(3S,3'R,3aR,6S,6aR)-6-hydroxy-3'-(4-hydroxyphenyl)-tetrahydro-2H-spiro[furo[3,2-b]furan-3,2'-oxolane]-2,5'-dioneoxy]-3-(acetyloxy)-4,5-dihydroxyoxan-2-yl]methyl acetate belongs to the class of organic compounds known as tetracarboxylic acids and derivatives. These are carboxylic acids containing exactly four carboxyl groups. (-)-4',6'-Diacetylviburnolide A is found in Guidia socotrana (Balf f.). Based on a literature review very few articles have been published on [(2R,3R,4R,5R,6S)-6-[(3S,3'R,3aR,6S,6aR)-6-hydroxy-3'-(4-hydroxyphenyl)-tetrahydro-2H-spiro[furo[3,2-b]furan-3,2'-oxolane]-2,5'-dioneoxy]-3-(acetyloxy)-4,5-dihydroxyoxan-2-yl]methyl acetate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282222182D          

 40 44  0  0  1  0            999 V2000
    2.7128   -1.4388    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.2474   -0.8104    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8149   -0.1078    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0131   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0762    0.5206    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9500   -1.1246    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8869   -1.9472    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0851   -2.1413    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7709   -2.9042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6526   -1.4388    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1872   -0.8104    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9930   -0.0085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2015    0.2242    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0073    1.0260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6046    1.5951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3961    1.3624    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5903    0.5605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4105    2.3969    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0102   -1.1246    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.9471   -1.9472    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1453   -2.1413    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7128   -0.6921    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1783   -2.0672    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4552   -2.8443    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.2667   -2.9930    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5437   -3.7702    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0091   -4.3986    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1976   -4.2498    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9207   -3.4727    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6631   -4.8782    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9400   -5.6554    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4055   -6.2838    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6824   -7.0609    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5940   -6.1350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2860   -5.1757    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0975   -5.3244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6321   -4.6960    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3745   -6.1016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3551   -3.9189    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8013   -2.3646    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  6  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4  6  1  0  0  0  0
  1  6  1  0  0  0  0
  6  7  1  6  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
  6 11  1  0  0  0  0
 11 12  1  6  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 12 17  1  0  0  0  0
 15 18  1  0  0  0  0
  2 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
  1 21  1  0  0  0  0
 19 22  1  1  0  0  0
  1 23  1  1  0  0  0
 24 23  1  1  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 24 29  1  0  0  0  0
 28 30  1  1  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  2  0  0  0  0
 32 34  1  0  0  0  0
 27 35  1  1  0  0  0
 35 36  1  0  0  0  0
 36 37  2  0  0  0  0
 36 38  1  0  0  0  0
 26 39  1  1  0  0  0
 25 40  1  6  0  0  0
M  END

     RDKit          3D

 68 72  0  0  0  0  0  0  0  0999 V2000
    3.9774   -4.8022   -0.2152 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2090   -3.5311   -0.0945 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7798   -2.5256    0.3058 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9096   -3.4820   -0.4182 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9461   -2.5137   -0.4376 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0115   -1.3822   -1.3743 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1148   -0.5568   -1.3160 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0750    0.7523   -0.9878 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2242    0.9016    0.3244 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5312    1.6105    1.1486 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6226    2.9661    0.8783 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5386    3.7051    2.0134 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2355    2.7893    3.1727 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8638    3.3300    3.8873 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2260    1.5452    2.5131 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3141    0.3400    3.0824 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6566    0.2773    2.7386 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4965   -0.3982    3.3711 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8675    1.1045    1.5758 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.5021    2.3197    2.1734 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7624    1.8616    2.5171 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4324    2.1566    3.5708 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1856    0.9584    1.4194 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8768    0.8003    0.5910 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.0205   -0.4115   -0.1417 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5433   -0.2917   -1.4430 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7358   -1.3586   -2.2674 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4275   -2.6264   -1.8720 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6236   -3.7224   -2.7142 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9152   -2.7859   -0.6101 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7201   -1.6910    0.2291 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0864    1.4665   -1.8556 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4874    2.3054   -2.8120 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8678    0.4537   -2.6257 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.0432    0.9490   -3.1628 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2674   -0.6121   -1.5017 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5814    0.2521   -0.4442 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8686    0.5622   -0.1244 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2410    1.4714    1.0020 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8313    0.0870   -0.7774 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4396   -4.8617   -1.2350 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3483   -5.6921    0.0067 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8156   -4.7755    0.5147 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7935   -2.0900    0.6322 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0380   -3.0922   -0.5517 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8701   -1.8626   -2.4194 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9013    1.2900   -1.2632 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3334    4.4131    1.8674 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3905    4.3492    2.2243 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0287    2.6973    3.9141 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6256    3.2653    3.2420 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2921    1.4756    2.3177 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9683    1.4499    0.8447 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4819   -0.0165    1.8338 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9515    1.6923   -0.1146 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8226    0.6852   -1.8541 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1459   -1.2507   -3.2843 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9999   -3.5650   -3.6285 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6680   -3.7973   -0.2914 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3153   -1.8595    1.1921 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8260    2.0358   -1.2402 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9364    3.1888   -2.8446 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2764   -0.1230   -3.3299 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6297    0.1722   -3.3593 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1463   -1.1257   -1.9426 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0674    2.5266    0.7505 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2960    1.3571    1.2894 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6415    1.2389    1.9121 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
 10  9  1  6
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 17 19  1  0
 19 20  1  1
 20 21  1  0
 21 22  2  0
 21 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 28 29  1  0
 28 30  1  0
 30 31  2  0
  8 32  1  0
 32 33  1  0
 32 34  1  0
 34 35  1  0
 34 36  1  0
 36 37  1  0
 37 38  1  0
 38 39  1  0
 38 40  2  0
 36  6  1  0
 15 10  1  0
 24 19  1  0
 31 25  1  0
 19 10  1  0
  1 41  1  0
  1 42  1  0
  1 43  1  0
  5 44  1  0
  5 45  1  0
  6 46  1  6
  8 47  1  6
 12 48  1  0
 12 49  1  0
 13 50  1  1
 14 51  1  0
 15 52  1  6
 23 53  1  0
 23 54  1  0
 24 55  1  6
 26 56  1  0
 27 57  1  0
 29 58  1  0
 30 59  1  0
 31 60  1  0
 32 61  1  1
 33 62  1  0
 34 63  1  6
 35 64  1  0
 36 65  1  6
 39 66  1  0
 39 67  1  0
 39 68  1  0
M  END


  Mrv1652304282222182D          

 40 44  0  0  1  0            999 V2000
    2.7128   -1.4388    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.2474   -0.8104    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8149   -0.1078    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0131   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0762    0.5206    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9500   -1.1246    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8869   -1.9472    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0851   -2.1413    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7709   -2.9042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6526   -1.4388    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1872   -0.8104    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9930   -0.0085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2015    0.2242    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0073    1.0260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6046    1.5951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3961    1.3624    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5903    0.5605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4105    2.3969    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0102   -1.1246    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.9471   -1.9472    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1453   -2.1413    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7128   -0.6921    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1783   -2.0672    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4552   -2.8443    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.2667   -2.9930    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5437   -3.7702    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0091   -4.3986    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1976   -4.2498    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9207   -3.4727    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6631   -4.8782    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9400   -5.6554    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4055   -6.2838    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6824   -7.0609    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5940   -6.1350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2860   -5.1757    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0975   -5.3244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6321   -4.6960    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3745   -6.1016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3551   -3.9189    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8013   -2.3646    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  6  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4  6  1  0  0  0  0
  1  6  1  0  0  0  0
  6  7  1  6  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
  6 11  1  0  0  0  0
 11 12  1  6  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 12 17  1  0  0  0  0
 15 18  1  0  0  0  0
  2 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
  1 21  1  0  0  0  0
 19 22  1  1  0  0  0
  1 23  1  1  0  0  0
 24 23  1  1  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 24 29  1  0  0  0  0
 28 30  1  1  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  2  0  0  0  0
 32 34  1  0  0  0  0
 27 35  1  1  0  0  0
 35 36  1  0  0  0  0
 36 37  2  0  0  0  0
 36 38  1  0  0  0  0
 26 39  1  1  0  0  0
 25 40  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0074991

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)OC[C@H]1O[C@@H](O[C@]23OC[C@H](O)[C@H]2OC(=O)[C@@]32OC(=O)C[C@@H]2C2=CC=C(O)C=C2)[C@H](O)[C@@H](O)[C@H]1OC(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C25H28O15/c1-10(26)34-9-16-20(36-11(2)27)18(31)19(32)22(37-16)40-25-21(15(29)8-35-25)38-23(33)24(25)14(7-17(30)39-24)12-3-5-13(28)6-4-12/h3-6,14-16,18-22,28-29,31-32H,7-9H2,1-2H3/t14-,15+,16-,18-,19-,20+,21-,22+,24-,25-/m1/s1

> <INCHI_KEY>
QHPQAHUEQHZVON-AKIICMJHSA-N

> <FORMULA>
C25H28O15

> <MOLECULAR_WEIGHT>
568.484

> <EXACT_MASS>
568.142820202

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_ATOM_COUNT>
68

> <JCHEM_AVERAGE_POLARIZABILITY>
53.08414972100832

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
[(2R,3R,4R,5R,6S)-6-[(3S,3'R,3aR,6S,6aR)-6-hydroxy-3'-(4-hydroxyphenyl)-tetrahydro-2H-spiro[furo[3,2-b]furan-3,2'-oxolane]-2,5'-dioneoxy]-3-(acetyloxy)-4,5-dihydroxyoxan-2-yl]methyl acetate

> <ALOGPS_LOGP>
0.08

> <JCHEM_LOGP>
-0.7225406973333336

> <ALOGPS_LOGS>
-1.84

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.220693868322238

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.497831281726539

> <JCHEM_PKA_STRONGEST_BASIC>
-3.5800790498057626

> <JCHEM_POLAR_SURFACE_AREA>
213.80999999999997

> <JCHEM_REFRACTIVITY>
122.01129999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
8.22e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[(2R,3R,4R,5R,6S)-6-[(3S,3'R,3aR,6S,6aR)-6-hydroxy-3'-(4-hydroxyphenyl)-dihydro-5H-spiro[furo[3,2-b]furan-3,2'-oxolane]-2,5'-dioneoxy]-3-(acetyloxy)-4,5-dihydroxyoxan-2-yl]methyl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0       5.064  -2.686   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.062  -1.513   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       5.255  -0.201   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       3.758  -0.564   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       3.876   0.972   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       3.640  -2.099   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       3.522  -3.635   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       2.026  -3.997   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       1.439  -5.421   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       1.218  -2.686   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.216  -1.513   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.854  -0.016   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.376   0.418   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.014   1.915   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.129   2.978   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.606   2.543   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.969   1.046   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       0.766   4.474   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       7.486  -2.099   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       7.368  -3.635   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       5.871  -3.997   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       8.797  -1.292   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       4.066  -3.859   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       4.583  -5.309   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       6.098  -5.587   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       6.615  -7.038   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       5.617  -8.211   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       4.102  -7.933   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       3.585  -6.482   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       3.104  -9.106   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       3.621 -10.557   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       2.624 -11.730   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       3.140 -13.180   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       1.109 -11.452   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0       6.134  -9.661   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0       7.649  -9.939   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0       8.647  -8.766   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0       8.166 -11.390   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0       8.130  -7.315   0.000  0.00  0.00           O+0
HETATM   40  O   UNK     0       7.096  -4.414   0.000  0.00  0.00           O+0
CONECT    1    2    6   21   23                                             
CONECT    2    1    3   19                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    1    7   11                                             
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10    6   12                                                  
CONECT   12   11   13   17                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   18                                                  
CONECT   16   15   17                                                       
CONECT   17   16   12                                                       
CONECT   18   15                                                            
CONECT   19    2   20   22                                                  
CONECT   20   19   21                                                       
CONECT   21   20    1                                                       
CONECT   22   19                                                            
CONECT   23    1   24                                                       
CONECT   24   23   25   29                                                  
CONECT   25   24   26   40                                                  
CONECT   26   25   27   39                                                  
CONECT   27   26   28   35                                                  
CONECT   28   27   29   30                                                  
CONECT   29   28   24                                                       
CONECT   30   28   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32                                                            
CONECT   35   27   36                                                       
CONECT   36   35   37   38                                                  
CONECT   37   36                                                            
CONECT   38   36                                                            
CONECT   39   26                                                            
CONECT   40   25                                                            
MASTER        0    0    0    0    0    0    0    0   40    0   88    0
END

View in JSmol

Synonyms

Value	Source
[(2R,3R,4R,5R,6S)-6-[(3S,3'r,3AR,6S,6ar)-6-hydroxy-3'-(4-hydroxyphenyl)-tetrahydro-2H-spiro[furo[3,2-b]furan-3,2'-oxolane]-2,5'-dioneoxy]-3-(acetyloxy)-4,5-dihydroxyoxan-2-yl]methyl acetic acid	Generator

Chemical Formula

C₂₅H₂₈O₁₅

Average Mass

568.4840 Da

Monoisotopic Mass

568.14282 Da

IUPAC Name

[(2R,3R,4R,5R,6S)-6-[(3S,3'R,3aR,6S,6aR)-6-hydroxy-3'-(4-hydroxyphenyl)-tetrahydro-2H-spiro[furo[3,2-b]furan-3,2'-oxolane]-2,5'-dioneoxy]-3-(acetyloxy)-4,5-dihydroxyoxan-2-yl]methyl acetate

Traditional Name

[(2R,3R,4R,5R,6S)-6-[(3S,3'R,3aR,6S,6aR)-6-hydroxy-3'-(4-hydroxyphenyl)-dihydro-5H-spiro[furo[3,2-b]furan-3,2'-oxolane]-2,5'-dioneoxy]-3-(acetyloxy)-4,5-dihydroxyoxan-2-yl]methyl acetate

CAS Registry Number

Not Available

SMILES

CC(=O)OC[C@H]1O[C@@H](O[C@]23OC[C@H](O)[C@H]2OC(=O)[C@@]32OC(=O)C[C@@H]2C2=CC=C(O)C=C2)[C@H](O)[C@@H](O)[C@H]1OC(C)=O

InChI Identifier

InChI=1S/C25H28O15/c1-10(26)34-9-16-20(36-11(2)27)18(31)19(32)22(37-16)40-25-21(15(29)8-35-25)38-23(33)24(25)14(7-17(30)39-24)12-3-5-13(28)6-4-12/h3-6,14-16,18-22,28-29,31-32H,7-9H2,1-2H3/t14-,15+,16-,18-,19-,20+,21-,22+,24-,25-/m1/s1

InChI Key

QHPQAHUEQHZVON-AKIICMJHSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Guidia socotrana (Balf f.)	-	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as tetracarboxylic acids and derivatives. These are carboxylic acids containing exactly four carboxyl groups.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Tetracarboxylic acids and derivatives

Direct Parent

Tetracarboxylic acids and derivatives

Alternative Parents

Substituents

Tetracarboxylic acid or derivatives
O-glycosyl compound
Glycosyl compound
Disaccharide
Isosorbide
Furofuran
1-hydroxy-2-unsubstituted benzenoid
Ketal
Phenol
Benzenoid
Oxane
Gamma butyrolactone
Monocyclic benzene moiety
Tetrahydrofuran
Secondary alcohol
Lactone
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Acetal
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
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	0.08	ALOGPS
logP	-0.72	ChemAxon
logS	-1.8	ALOGPS
pKa (Strongest Acidic)	9.5	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	213.81 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	122.01 m³·mol⁻¹	ChemAxon
Polarizability	53.08 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	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

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

162884219

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for (-)-4',6'-Diacetylviburnolide A (NP0074991)

MOL for NP0074991 ((-)-4',6'-Diacetylviburnolide A)

3D MOL for NP0074991 ((-)-4',6'-Diacetylviburnolide A)

3D SDF for NP0074991 ((-)-4',6'-Diacetylviburnolide A)

3D-SDF for NP0074991 ((-)-4',6'-Diacetylviburnolide A)

PDB for NP0074991 ((-)-4',6'-Diacetylviburnolide A)

3D PDB for NP0074991 ((-)-4',6'-Diacetylviburnolide A)

SMILES for NP0074991 ((-)-4',6'-Diacetylviburnolide A)

INCHI for NP0074991 ((-)-4',6'-Diacetylviburnolide A)

Structure for NP0074991 ((-)-4',6'-Diacetylviburnolide A)

3D Structure for NP0074991 ((-)-4',6'-Diacetylviburnolide A)