NP-MRD: Showing NP-Card for [(2r,3s,4s,5r,6s)-5-(acetyloxy)-3,4-dihydroxy-6-[(9r)-1,4,5-trihydroxy-7-(hydroxymethyl)-10-oxo-9h-anthracen-9-yl]oxan-2-yl]methyl acetate (NP0325956)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-12 07:06:26 UTC

Updated at

2022-09-12 07:06:26 UTC

NP-MRD ID

NP0325956

Secondary Accession Numbers

None

Natural Product Identification

Common Name

[(2r,3s,4s,5r,6s)-5-(acetyloxy)-3,4-dihydroxy-6-[(9r)-1,4,5-trihydroxy-7-(hydroxymethyl)-10-oxo-9h-anthracen-9-yl]oxan-2-yl]methyl acetate

Description

[(2R,3S,4S,5R,6S)-5-(acetyloxy)-3,4-dihydroxy-6-[(9R)-1,4,5-trihydroxy-7-(hydroxymethyl)-10-oxo-9,10-dihydroanthracen-9-yl]oxan-2-yl]methyl acetate belongs to the class of organic compounds known as anthracenes. These are organic compounds containing a system of three linearly fused benzene rings. [(2r,3s,4s,5r,6s)-5-(acetyloxy)-3,4-dihydroxy-6-[(9r)-1,4,5-trihydroxy-7-(hydroxymethyl)-10-oxo-9h-anthracen-9-yl]oxan-2-yl]methyl acetate is found in Aloe perfoliata. Based on a literature review very few articles have been published on [(2R,3S,4S,5R,6S)-5-(acetyloxy)-3,4-dihydroxy-6-[(9R)-1,4,5-trihydroxy-7-(hydroxymethyl)-10-oxo-9,10-dihydroanthracen-9-yl]oxan-2-yl]methyl acetate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309122209062D          

 37 40  0  0  1  0            999 V2000
   -1.4289    3.3000    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
   -0.7145    4.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    3.3000    0.0000 O   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
    1.4289    3.3000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 C   0  0  1  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
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -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
    3.5724   -1.2375    0.0000 O   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
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 O   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
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 O   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
    0.0000    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 O   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
    2.8579    2.4750    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    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
    5.0013    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    3.3000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5724    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    3.7125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1434    4.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  6  5  1  6  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  6  0  0  0
  9 10  1  6  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 12 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  2  0  0  0  0
 10 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 22 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 26 28  2  0  0  0  0
 21 28  1  0  0  0  0
  9 28  1  0  0  0  0
  8 29  1  0  0  0  0
 29 30  1  1  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 31 33  2  0  0  0  0
 29 34  1  0  0  0  0
 34 35  1  6  0  0  0
 34 36  1  0  0  0  0
  6 36  1  0  0  0  0
 36 37  1  1  0  0  0
M  END

     RDKit          3D

 63 66  0  0  0  0  0  0  0  0999 V2000
    5.0916   -2.5401   -3.2066 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7287   -2.1888   -2.7500 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0101   -1.4834   -3.4888 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2364   -2.6172   -1.5397 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9681   -2.3262   -1.0444 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7152   -0.8496   -0.8628 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4675   -0.6839   -0.3895 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0363    0.6727   -0.2368 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1480    0.5351    0.6265 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.0215   -0.6194    0.2651 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9490   -1.2859   -0.9130 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6088   -2.5090   -1.0920 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5332   -3.2467   -2.3769 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2849   -4.4087   -2.2918 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3429   -3.0375   -0.0471 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4189   -2.3559    1.1477 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1580   -2.9031    2.1760 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7552   -1.1216    1.3185 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0796   -0.2858    2.4698 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7212   -0.7518    3.4301 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6009    1.1311    2.4175 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1681    2.0275    3.3117 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8619    1.6210    4.4144 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0300    3.4171    3.0925 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3428    3.8021    2.0025 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7461    2.9292    1.0673 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1083    3.4754    0.0033 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8731    1.5766    1.2933 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1232    1.4648    0.3726 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8236    2.3537   -0.4589 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1076    3.6623   -0.2471 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8633    4.5214   -1.2173 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7261    4.1963    0.8095 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2059    0.5968    1.0867 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6299   -0.2400    2.0207 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7988   -0.2415   -0.0140 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.7050    0.5347   -0.7185 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0878   -3.4624   -3.8471 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7667   -2.7923   -2.3537 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5828   -1.6848   -3.7413 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8339   -2.8633   -0.0664 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2197   -2.7976   -1.7189 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7887   -0.3766   -1.8542 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2198    0.9457   -1.2417 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5851    0.0225    1.5706 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3910   -0.8887   -1.7325 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9332   -2.6486   -3.2236 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4822   -3.5688   -2.6146 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2476   -4.2491   -2.5315 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8661   -4.0001   -0.1636 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6436   -3.7828    2.0877 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0825    0.7754    4.7913 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4858    4.0852    3.8152 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2102    4.8748    1.7826 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7220    3.0726   -0.7718 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7650    2.0399    1.2364 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1748    3.8850   -2.0735 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1786    5.3182   -1.5330 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7378    4.9068   -0.6545 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9541    1.2950    1.4820 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3173   -0.3881    2.7403 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3695   -1.0578    0.4618 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6073    0.5181   -0.2766 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 29  1  0
 29 30  1  0
 30 31  1  0
 31 32  1  0
 31 33  2  0
 29 34  1  0
 34 35  1  0
 34 36  1  0
 36 37  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 12 15  2  0
 15 16  1  0
 16 17  1  0
 16 18  2  0
 18 19  1  0
 19 20  2  0
 19 21  1  0
 21 22  2  0
 22 23  1  0
 22 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  1  0
 26 28  2  0
 36  6  1  0
 28  9  1  0
 18 10  1  0
 28 21  1  0
  1 38  1  0
  1 39  1  0
  1 40  1  0
  5 41  1  0
  5 42  1  0
  6 43  1  6
  8 44  1  6
 29 56  1  1
 32 57  1  0
 32 58  1  0
 32 59  1  0
 34 60  1  1
 35 61  1  0
 36 62  1  1
 37 63  1  0
  9 45  1  1
 11 46  1  0
 13 47  1  0
 13 48  1  0
 14 49  1  0
 15 50  1  0
 17 51  1  0
 23 52  1  0
 24 53  1  0
 25 54  1  0
 27 55  1  0
M  END


  Mrv1652309122209062D          

 37 40  0  0  1  0            999 V2000
   -1.4289    3.3000    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
   -0.7145    4.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    3.3000    0.0000 O   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
    1.4289    3.3000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 C   0  0  1  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
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -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
    3.5724   -1.2375    0.0000 O   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
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 O   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
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 O   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
    0.0000    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 O   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
    2.8579    2.4750    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    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
    5.0013    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    3.3000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5724    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    3.7125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1434    4.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  6  5  1  6  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  6  0  0  0
  9 10  1  6  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 12 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  2  0  0  0  0
 10 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 22 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 26 28  2  0  0  0  0
 21 28  1  0  0  0  0
  9 28  1  0  0  0  0
  8 29  1  0  0  0  0
 29 30  1  1  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 31 33  2  0  0  0  0
 29 34  1  0  0  0  0
 34 35  1  6  0  0  0
 34 36  1  0  0  0  0
  6 36  1  0  0  0  0
 36 37  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0325956

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)OC[C@H]1O[C@H]([C@H](OC(C)=O)[C@@H](O)[C@@H]1O)[C@@H]1C2=CC(CO)=CC(O)=C2C(=O)C2=C(O)C=CC(O)=C12

> <INCHI_IDENTIFIER>
InChI=1S/C25H26O12/c1-9(27)35-8-16-21(32)23(34)25(36-10(2)28)24(37-16)18-12-5-11(7-26)6-15(31)17(12)22(33)20-14(30)4-3-13(29)19(18)20/h3-6,16,18,21,23-26,29-32,34H,7-8H2,1-2H3/t16-,18-,21-,23+,24+,25-/m1/s1

> <INCHI_KEY>
LCGFTZURIZOVSV-MWDSBHAUSA-N

> <FORMULA>
C25H26O12

> <MOLECULAR_WEIGHT>
518.471

> <EXACT_MASS>
518.142426277

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
63

> <JCHEM_AVERAGE_POLARIZABILITY>
49.53980920371695

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
[(2R,3S,4S,5R,6S)-5-(acetyloxy)-3,4-dihydroxy-6-[(9R)-1,4,5-trihydroxy-7-(hydroxymethyl)-10-oxo-9,10-dihydroanthracen-9-yl]oxan-2-yl]methyl acetate

> <JCHEM_LOGP>
0.9936752246666662

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.00814127586312

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.309814342630899

> <JCHEM_PKA_STRONGEST_BASIC>
-2.884587110579039

> <JCHEM_POLAR_SURFACE_AREA>
200.27999999999997

> <JCHEM_REFRACTIVITY>
124.07699999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
[(2R,3S,4S,5R,6S)-5-(acetyloxy)-3,4-dihydroxy-6-[(9R)-1,4,5-trihydroxy-7-(hydroxymethyl)-10-oxo-9H-anthracen-9-yl]oxan-2-yl]methyl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 12-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-SEP-22         0                                  
HETATM    1  C   UNK     0      -2.667   6.160   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.334   6.930   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -1.334   8.470   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      -0.000   6.160   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       1.334   6.930   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667   6.160   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       2.667   4.620   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       4.001   3.850   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       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       9.336   2.310   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      10.669   1.540   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       8.002  -0.000   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       6.668  -2.310   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       4.001  -2.310   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       0.000   1.540   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       1.334   3.850   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       5.335   4.620   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       6.668   3.850   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       8.002   4.620   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       9.336   3.850   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       8.002   6.160   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       5.335   6.160   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0       6.668   6.930   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0       4.001   6.930   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0       4.001   8.470   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   36                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   29                                                  
CONECT    9    8   10   28                                                  
CONECT   10    9   11   18                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   15                                                  
CONECT   13   12   14                                                       
CONECT   14   13                                                            
CONECT   15   12   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   10   19                                                  
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22   28                                                  
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   21    9                                                  
CONECT   29    8   30   34                                                  
CONECT   30   29   31                                                       
CONECT   31   30   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31                                                            
CONECT   34   29   35   36                                                  
CONECT   35   34                                                            
CONECT   36   34    6   37                                                  
CONECT   37   36                                                            
MASTER        0    0    0    0    0    0    0    0   37    0   80    0
END

View in JSmol

Synonyms

Value	Source
[(2R,3S,4S,5R,6S)-5-(Acetyloxy)-3,4-dihydroxy-6-[(9R)-1,4,5-trihydroxy-7-(hydroxymethyl)-10-oxo-9,10-dihydroanthracen-9-yl]oxan-2-yl]methyl acetic acid	Generator

Chemical Formula

C₂₅H₂₆O₁₂

Average Mass

518.4710 Da

Monoisotopic Mass

518.14243 Da

IUPAC Name

[(2R,3S,4S,5R,6S)-5-(acetyloxy)-3,4-dihydroxy-6-[(9R)-1,4,5-trihydroxy-7-(hydroxymethyl)-10-oxo-9,10-dihydroanthracen-9-yl]oxan-2-yl]methyl acetate

Traditional Name

[(2R,3S,4S,5R,6S)-5-(acetyloxy)-3,4-dihydroxy-6-[(9R)-1,4,5-trihydroxy-7-(hydroxymethyl)-10-oxo-9H-anthracen-9-yl]oxan-2-yl]methyl acetate

CAS Registry Number

Not Available

SMILES

CC(=O)OC[C@H]1O[C@H]([C@H](OC(C)=O)[C@@H](O)[C@@H]1O)[C@@H]1C2=CC(CO)=CC(O)=C2C(=O)C2=C(O)C=CC(O)=C12

InChI Identifier

InChI=1S/C25H26O12/c1-9(27)35-8-16-21(32)23(34)25(36-10(2)28)24(37-16)18-12-5-11(7-26)6-15(31)17(12)22(33)20-14(30)4-3-13(29)19(18)20/h3-6,16,18,21,23-26,29-32,34H,7-8H2,1-2H3/t16-,18-,21-,23+,24+,25-/m1/s1

InChI Key

LCGFTZURIZOVSV-MWDSBHAUSA-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
Aloe perfoliata	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as anthracenes. These are organic compounds containing a system of three linearly fused benzene rings.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Anthracenes

Sub Class

Not Available

Direct Parent

Anthracenes

Alternative Parents

Substituents

Anthracene
C-glycosyl compound
Glycosyl compound
Aryl ketone
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Dicarboxylic acid or derivatives
Monosaccharide
Oxane
Vinylogous acid
Carboxylic acid ester
Ketone
Secondary alcohol
Carboxylic acid derivative
Dialkyl ether
Oxacycle
Ether
Organoheterocyclic compound
Polyol
Organic oxygen compound
Hydrocarbon derivative
Organic oxide
Carbonyl group
Aromatic alcohol
Primary alcohol
Organooxygen compound
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	0.99	ChemAxon
pKa (Strongest Acidic)	8.31	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	200.28 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	124.08 m³·mol⁻¹	ChemAxon
Polarizability	49.54 Å³	ChemAxon
Number of Rings	4	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

46844574

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for [(2r,3s,4s,5r,6s)-5-(acetyloxy)-3,4-dihydroxy-6-[(9r)-1,4,5-trihydroxy-7-(hydroxymethyl)-10-oxo-9h-anthracen-9-yl]oxan-2-yl]methyl acetate (NP0325956)

MOL for NP0325956 ([(2r,3s,4s,5r,6s)-5-(acetyloxy)-3,4-dihydroxy-6-[(9r)-1,4,5-trihydroxy-7-(hydroxymethyl)-10-oxo-9h-anthracen-9-yl]oxan-2-yl]methyl acetate)

3D MOL for NP0325956 ([(2r,3s,4s,5r,6s)-5-(acetyloxy)-3,4-dihydroxy-6-[(9r)-1,4,5-trihydroxy-7-(hydroxymethyl)-10-oxo-9h-anthracen-9-yl]oxan-2-yl]methyl acetate)

3D SDF for NP0325956 ([(2r,3s,4s,5r,6s)-5-(acetyloxy)-3,4-dihydroxy-6-[(9r)-1,4,5-trihydroxy-7-(hydroxymethyl)-10-oxo-9h-anthracen-9-yl]oxan-2-yl]methyl acetate)

3D-SDF for NP0325956 ([(2r,3s,4s,5r,6s)-5-(acetyloxy)-3,4-dihydroxy-6-[(9r)-1,4,5-trihydroxy-7-(hydroxymethyl)-10-oxo-9h-anthracen-9-yl]oxan-2-yl]methyl acetate)

PDB for NP0325956 ([(2r,3s,4s,5r,6s)-5-(acetyloxy)-3,4-dihydroxy-6-[(9r)-1,4,5-trihydroxy-7-(hydroxymethyl)-10-oxo-9h-anthracen-9-yl]oxan-2-yl]methyl acetate)

3D PDB for NP0325956 ([(2r,3s,4s,5r,6s)-5-(acetyloxy)-3,4-dihydroxy-6-[(9r)-1,4,5-trihydroxy-7-(hydroxymethyl)-10-oxo-9h-anthracen-9-yl]oxan-2-yl]methyl acetate)

SMILES for NP0325956 ([(2r,3s,4s,5r,6s)-5-(acetyloxy)-3,4-dihydroxy-6-[(9r)-1,4,5-trihydroxy-7-(hydroxymethyl)-10-oxo-9h-anthracen-9-yl]oxan-2-yl]methyl acetate)

INCHI for NP0325956 ([(2r,3s,4s,5r,6s)-5-(acetyloxy)-3,4-dihydroxy-6-[(9r)-1,4,5-trihydroxy-7-(hydroxymethyl)-10-oxo-9h-anthracen-9-yl]oxan-2-yl]methyl acetate)

Structure for NP0325956 ([(2r,3s,4s,5r,6s)-5-(acetyloxy)-3,4-dihydroxy-6-[(9r)-1,4,5-trihydroxy-7-(hydroxymethyl)-10-oxo-9h-anthracen-9-yl]oxan-2-yl]methyl acetate)

3D Structure for NP0325956 ([(2r,3s,4s,5r,6s)-5-(acetyloxy)-3,4-dihydroxy-6-[(9r)-1,4,5-trihydroxy-7-(hydroxymethyl)-10-oxo-9h-anthracen-9-yl]oxan-2-yl]methyl acetate)