NP-MRD: Showing NP-Card for Xylogranatin D (NP0072583)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-04-28 17:54:48 UTC

Updated at

2022-04-28 17:54:48 UTC

NP-MRD ID

NP0072583

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Xylogranatin D

Description

Xylogranatin D belongs to the class of organic compounds known as tricarboxylic acids and derivatives. These are carboxylic acids containing exactly three carboxyl groups. Xylogranatin D is found in Xylocarpus granatum . Xylogranatin D was first documented in 2006 (PMID: 17020340). Based on a literature review very few articles have been published on Xylogranatin D (PMID: 18046683).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282219542D          

 39 42  0  0  1  0            999 V2000
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 O   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 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  2  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
    0.7145   -0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1100   -0.3837    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2773    0.2871    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5472    0.2583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9844    0.9580    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8089    0.9292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1962    0.2008    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.7590   -0.4989    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9345   -0.4701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4973   -1.1697    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1463   -1.2273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0207    0.1720    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4080   -0.5565    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9708   -1.2561    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2325   -0.5853    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6198   -1.3137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8664    1.7522    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5234    1.3417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6646    1.0156    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2274    1.7152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5971    1.6864    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6147    2.4436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.0625    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
    2.1904   -2.9599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4454   -3.7445    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2704   -3.7445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5253   -2.9599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  3  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
  1 12  1  0  0  0  0
 12 13  1  1  0  0  0
 12 14  1  6  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 15 20  1  0  0  0  0
 20 21  2  0  0  0  0
 19 22  1  6  0  0  0
 18 23  1  1  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 24 26  1  0  0  0  0
 26 27  1  0  0  0  0
 17 28  1  0  0  0  0
 17 29  1  0  0  0  0
 14 30  1  1  0  0  0
 30 31  1  0  0  0  0
 31 32  2  0  0  0  0
 31 33  1  0  0  0  0
  9 34  1  1  0  0  0
  8 35  1  1  0  0  0
 35 36  2  0  0  0  0
 36 37  1  0  0  0  0
 37 38  1  0  0  0  0
 38 39  2  0  0  0  0
 35 39  1  0  0  0  0
M  END

     RDKit          3D

 73 76  0  0  0  0  0  0  0  0999 V2000
    7.0434    3.4128   -0.1747 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4108    2.2673    0.3552 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0937    2.3639    0.8440 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5447    3.5018    0.7759 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4423    1.1672    1.3938 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6675    0.3607    0.3375 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6151    1.2265   -0.2542 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.2513    2.0112   -1.4104 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5183    0.4025   -0.8762 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8865    0.9684   -1.8071 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2534   -0.9408   -0.4024 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0475   -1.6821   -0.8423 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2020   -3.0629   -0.9253 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2954   -3.8249   -2.0494 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4546   -5.2950   -1.9013 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2433   -3.2562   -3.1616 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2581   -1.2290   -0.3038 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.5101   -1.7481    0.9855 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4546    0.2526   -0.1630 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7346    0.4259    0.6888 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9390    0.0726   -0.1421 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.8663   -0.7262    0.7864 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5459   -0.8133   -1.2927 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2087   -0.7879   -2.4328 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3434    0.0986   -2.6213 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9742    0.1108   -3.7299 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7015    0.9120   -1.5660 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7212    1.2588   -0.6231 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.3894    1.9939    0.4775 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9594    3.1623    1.1090 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8831    3.4823    2.0630 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8222    2.5818    2.0320 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5816    1.6798    1.1152 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3909   -1.7258   -1.1394 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4282   -2.8358   -1.7050 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0549   -1.5273    0.4510 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2573   -0.8896    0.9894 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.4564   -1.8597    0.9012 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0596   -0.6995    2.5042 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8214    3.1243   -0.9049 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2910    4.0623   -0.6911 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4538    3.9819    0.6909 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7934    1.4866    2.2239 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2579    0.5281    1.8247 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4338    0.1278   -0.4469 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1495    1.9602    0.4128 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3469    1.9098   -1.4395 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9437    3.0811   -1.3903 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9136    1.5689   -2.3981 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0089   -1.3734   -1.9546 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3455   -5.7377   -1.2761 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4236   -5.5543   -1.4219 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4896   -5.7606   -2.9192 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0822   -2.6364    1.0872 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6109    0.7475    0.3663 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7278    0.7170   -1.1273 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7583    1.4884    1.0320 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6040   -0.2269    1.5626 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8093   -0.9864    0.3087 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0040   -0.1157    1.7021 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3278   -1.6516    1.1397 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8843   -1.4599   -3.2432 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0219    1.9676   -1.1074 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0397    3.6650    0.8297 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8381    4.3261    2.7181 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2306    0.8435    0.9189 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8067   -2.5826    0.7903 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0622   -2.8743    1.1869 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1895   -1.5113    1.6370 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8952   -1.8597   -0.0985 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0255   -0.5632    3.0063 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3436    0.1240    2.6374 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5670   -1.6260    2.8847 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
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  2  0
  9 11  1  0
 11 36  2  0
 36 37  1  0
 37 38  1  1
 37 39  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  2  0
 12 17  1  0
 17 18  1  1
 17 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  1
 21 28  1  0
 28 27  1  0
 27 25  1  0
 25 26  2  0
 25 24  1  0
 24 23  2  0
 23 34  1  0
 34 35  2  0
 28 29  1  0
 29 33  2  0
 33 32  1  0
 32 31  1  0
 31 30  2  0
 37  6  1  0
 34 17  1  0
 30 29  1  0
 23 21  1  0
  1 40  1  0
  1 41  1  0
  1 42  1  0
  5 43  1  0
  5 44  1  0
  6 45  1  6
  7 46  1  1
  8 47  1  0
  8 48  1  0
  8 49  1  0
 36 67  1  0
 38 68  1  0
 38 69  1  0
 38 70  1  0
 39 71  1  0
 39 72  1  0
 39 73  1  0
 12 50  1  6
 15 51  1  0
 15 52  1  0
 15 53  1  0
 18 54  1  0
 19 55  1  0
 19 56  1  0
 20 57  1  0
 20 58  1  0
 22 59  1  0
 22 60  1  0
 22 61  1  0
 28 63  1  6
 24 62  1  0
 33 66  1  0
 31 65  1  0
 30 64  1  0
M  END


  Mrv1652304282219542D          

 39 42  0  0  1  0            999 V2000
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 O   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 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  2  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
    0.7145   -0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1100   -0.3837    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2773    0.2871    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5472    0.2583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9844    0.9580    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8089    0.9292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1962    0.2008    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.7590   -0.4989    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9345   -0.4701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4973   -1.1697    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1463   -1.2273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0207    0.1720    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4080   -0.5565    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9708   -1.2561    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2325   -0.5853    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6198   -1.3137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8664    1.7522    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5234    1.3417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6646    1.0156    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2274    1.7152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5971    1.6864    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6147    2.4436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.0625    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
    2.1904   -2.9599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4454   -3.7445    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2704   -3.7445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5253   -2.9599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  3  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
  1 12  1  0  0  0  0
 12 13  1  1  0  0  0
 12 14  1  6  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 15 20  1  0  0  0  0
 20 21  2  0  0  0  0
 19 22  1  6  0  0  0
 18 23  1  1  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 24 26  1  0  0  0  0
 26 27  1  0  0  0  0
 17 28  1  0  0  0  0
 17 29  1  0  0  0  0
 14 30  1  1  0  0  0
 30 31  1  0  0  0  0
 31 32  2  0  0  0  0
 31 33  1  0  0  0  0
  9 34  1  1  0  0  0
  8 35  1  1  0  0  0
 35 36  2  0  0  0  0
 36 37  1  0  0  0  0
 37 38  1  0  0  0  0
 38 39  2  0  0  0  0
 35 39  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0072583

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)C[C@@H]1[C@@H](C)C(=O)C(=CC1(C)C)[C@@H](OC(C)=O)[C@@]1(O)CC[C@@]2(C)[C@@H](OC(=O)C=C2C1=O)C1=COC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C29H34O10/c1-15-19(11-21(31)36-6)27(3,4)13-18(23(15)33)26(38-16(2)30)29(35)9-8-28(5)20(24(29)34)12-22(32)39-25(28)17-7-10-37-14-17/h7,10,12-15,19,25-26,35H,8-9,11H2,1-6H3/t15-,19-,25+,26-,28-,29-/m1/s1

> <INCHI_KEY>
VUDBFSYVRWYNHG-CWDSGYGTSA-N

> <FORMULA>
C29H34O10

> <MOLECULAR_WEIGHT>
542.581

> <EXACT_MASS>
542.215197295

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
73

> <JCHEM_AVERAGE_POLARIZABILITY>
55.187895392675486

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(R)-[(1R,6S,8aR)-1-(furan-3-yl)-6-hydroxy-8a-methyl-3,5-dioxo-3,5,6,7,8,8a-hexahydro-1H-isochromen-6-yl][(4R,5R)-4-(2-methoxy-2-oxoethyl)-3,3,5-trimethyl-6-oxocyclohex-1-en-1-yl]methyl acetate

> <ALOGPS_LOGP>
2.88

> <JCHEM_LOGP>
3.3165746969999996

> <ALOGPS_LOGS>
-4.30

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
19.37004952990901

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.988522710060291

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8887386340964127

> <JCHEM_POLAR_SURFACE_AREA>
146.41000000000003

> <JCHEM_REFRACTIVITY>
137.00769999999994

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.73e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(R)-[(1R,6S,8aR)-1-(furan-3-yl)-6-hydroxy-8a-methyl-3,5-dioxo-7,8-dihydro-1H-isochromen-6-yl][(4R,5R)-4-(2-methoxy-2-oxoethyl)-3,3,5-trimethyl-6-oxocyclohex-1-en-1-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       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       2.667   1.540   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       8.002  -0.000   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0       6.668  -2.310   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -0.205  -0.716   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       0.518   0.536   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -1.021   0.482   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -1.838   1.788   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -3.377   1.734   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -4.100   0.375   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -3.284  -0.931   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -1.744  -0.877   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      -0.928  -2.183   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      -4.006  -2.291   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -5.639   0.321   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -6.362  -1.039   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      -5.546  -2.345   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0      -7.901  -1.092   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      -8.624  -2.452   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -3.484   3.271   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -4.710   2.504   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       1.241   1.896   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       0.425   3.202   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      -1.115   3.148   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       1.148   4.561   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       4.001  -3.850   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       4.089  -5.525   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0       4.565  -6.990   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0       6.105  -6.990   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       6.581  -5.525   0.000  0.00  0.00           C+0
CONECT    1    2    3   12                                                  
CONECT    2    1                                                            
CONECT    3    1    4    9                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9   35                                                  
CONECT    9    8    3   10   34                                             
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11    1   13   14                                             
CONECT   13   12                                                            
CONECT   14   12   15   30                                                  
CONECT   15   14   16   20                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   28   29                                             
CONECT   18   17   19   23                                                  
CONECT   19   18   20   22                                                  
CONECT   20   19   15   21                                                  
CONECT   21   20                                                            
CONECT   22   19                                                            
CONECT   23   18   24                                                       
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   27                                                       
CONECT   27   26                                                            
CONECT   28   17                                                            
CONECT   29   17                                                            
CONECT   30   14   31                                                       
CONECT   31   30   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31                                                            
CONECT   34    9                                                            
CONECT   35    8   36   39                                                  
CONECT   36   35   37                                                       
CONECT   37   36   38                                                       
CONECT   38   37   39                                                       
CONECT   39   38   35                                                       
MASTER        0    0    0    0    0    0    0    0   39    0   84    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₉H₃₄O₁₀

Average Mass

542.5810 Da

Monoisotopic Mass

542.21520 Da

IUPAC Name

(R)-[(1R,6S,8aR)-1-(furan-3-yl)-6-hydroxy-8a-methyl-3,5-dioxo-3,5,6,7,8,8a-hexahydro-1H-isochromen-6-yl][(4R,5R)-4-(2-methoxy-2-oxoethyl)-3,3,5-trimethyl-6-oxocyclohex-1-en-1-yl]methyl acetate

Traditional Name

(R)-[(1R,6S,8aR)-1-(furan-3-yl)-6-hydroxy-8a-methyl-3,5-dioxo-7,8-dihydro-1H-isochromen-6-yl][(4R,5R)-4-(2-methoxy-2-oxoethyl)-3,3,5-trimethyl-6-oxocyclohex-1-en-1-yl]methyl acetate

CAS Registry Number

Not Available

SMILES

COC(=O)C[C@@H]1[C@@H](C)C(=O)C(=CC1(C)C)[C@@H](OC(C)=O)[C@@]1(O)CC[C@@]2(C)[C@@H](OC(=O)C=C2C1=O)C1=COC=C1

InChI Identifier

InChI=1S/C29H34O10/c1-15-19(11-21(31)36-6)27(3,4)13-18(23(15)33)26(38-16(2)30)29(35)9-8-28(5)20(24(29)34)12-22(32)39-25(28)17-7-10-37-14-17/h7,10,12-15,19,25-26,35H,8-9,11H2,1-6H3/t15-,19-,25+,26-,28-,29-/m1/s1

InChI Key

VUDBFSYVRWYNHG-CWDSGYGTSA-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
Xylocarpus granatum	Plant	KNApSAcK

Chemical Taxonomy

Description

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

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Tricarboxylic acids and derivatives

Direct Parent

Tricarboxylic acids and derivatives

Alternative Parents

Substituents

Tricarboxylic acid or derivatives
Dihydropyranone
Cyclohexenone
Acyloin
Pyran
Cyclic alcohol
Furan
Tertiary alcohol
Heteroaromatic compound
Methyl ester
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Lactone
Ketone
Carboxylic acid ester
Cyclic ketone
Organoheterocyclic compound
Oxacycle
Hydrocarbon derivative
Organooxygen compound
Alcohol
Carbonyl group
Organic oxygen compound
Organic oxide
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

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

Predicted Properties

Property	Value	Source
logP	2.88	ALOGPS
logP	3.32	ChemAxon
logS	-4.3	ALOGPS
pKa (Strongest Acidic)	11.99	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	146.41 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	137.01 m³·mol⁻¹	ChemAxon
Polarizability	55.19 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	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

C00032535

Chemspider ID

10481487

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

16091093

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Wu J, Zhang S, Bruhn T, Xiao Q, Ding H, Bringmann G: Xylogranatins F-R: antifeedants from the Chinese mangrove, Xylocarpus granatum, a new biogenetic pathway to tetranortriterpenoids. Chemistry. 2008;14(4):1129-44. doi: 10.1002/chem.200700663. [PubMed:18046683 ]
Yin S, Fan CQ, Wang XN, Lin LP, Ding J, Yue JM: Xylogranatins A-D: novel tetranortriterpenoids with an unusual 9,10-seco scaffold from marine mangrove Xylocarpus granatum. Org Lett. 2006 Oct 12;8(21):4935-8. doi: 10.1021/ol062101t. [PubMed:17020340 ]

Showing NP-Card for Xylogranatin D (NP0072583)

MOL for NP0072583 (Xylogranatin D)

3D MOL for NP0072583 (Xylogranatin D)

3D SDF for NP0072583 (Xylogranatin D)

3D-SDF for NP0072583 (Xylogranatin D)

PDB for NP0072583 (Xylogranatin D)

3D PDB for NP0072583 (Xylogranatin D)

SMILES for NP0072583 (Xylogranatin D)

INCHI for NP0072583 (Xylogranatin D)

Structure for NP0072583 (Xylogranatin D)

3D Structure for NP0072583 (Xylogranatin D)