NP-MRD: Showing NP-Card for Peonidin 3-(6''-malonylglucoside) (NP0054593)

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Record Information

Version

2.0

Created at

2022-04-28 00:53:56 UTC

Updated at

2022-04-28 00:53:56 UTC

NP-MRD ID

NP0054593

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Peonidin 3-(6''-malonylglucoside)

Description

Peonidin 3-(6''-malonylglucoside) is found in Alopecurus spp., Anthoxanthum spp., Avenula spp., Bothriochloa spp., Dactylis spp., Deschampsia spp., Elymus spp., Festuca spp., Hibiscus syriacus , Hordeum spp., Miscanthus spp., Molinia spp., Oryza spp., Phalaris spp., Phleum spp., Poa spp. and Sinarundinaria spp.. 3-{[(2S,3R,4S,5R,6R)-6-{[(2-carboxyacetyl)oxy]methyl}-3,4,5-trihydroxyoxan-2-yl]oxy}-5,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-1λ⁴-chromen-1-ylium is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI

Peonidin 3-O-(6''-malonyl-glucoside)
  Mrv1652310041811352D          

 39 42  0  0  1  0            999 V2000
    0.7145   -4.5375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4289   -4.9499    0.0000 C   0  0  0  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
    2.8579   -4.9499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -5.7750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.9499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0012   -4.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -5.7750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.9499    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -4.5375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4289   -4.9499    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -4.5375    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
   -2.8579   -3.3000    0.0000 C   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
   -4.2868   -3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868   -2.4749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0012   -2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -2.4749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -4.5375    0.0000 O   0  3  0  0  0  0  0  0  0  0  0  0
   -2.8579   -4.9499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -7.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -7.4250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -8.2500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -8.2500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -7.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -3.7125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4289   -3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -3.3000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0000   -2.4749    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -3.7125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4289   -3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  1  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  2  0  0  0  0
  1 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  1  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  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  2  0  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
 20 21  2  0  0  0  0
 15 21  1  0  0  0  0
 21 22  1  0  0  0  0
 16 23  1  0  0  0  0
 23 24  2  0  0  0  0
 13 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  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
 27 30  2  0  0  0  0
 30 31  1  0  0  0  0
 30 32  1  0  0  0  0
 32 33  2  0  0  0  0
 25 33  1  0  0  0  0
 11 34  1  0  0  0  0
 34 35  1  6  0  0  0
 34 36  1  0  0  0  0
 36 37  1  1  0  0  0
 36 38  1  0  0  0  0
  1 38  1  0  0  0  0
 38 39  1  1  0  0  0
M  CHG  1  23   1
M  END

     RDKit          3D

 64 67  0  0  0  0  0  0  0  0999 V2000
   -1.5521   -4.2609   -0.5694 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9265   -4.2566   -0.8880 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6773   -3.0865   -0.8929 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0820   -1.8580   -0.5765 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7472   -0.6731   -0.5593 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2095    0.6365   -0.2446 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0137    1.6997   -0.2775 O   0  0  0  0  0  3  0  0  0  0  0  0
   -3.6301    2.9136   -0.0124 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5302    3.9763   -0.0676 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1455    5.2680    0.2089 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0645    6.3193    0.1477 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8407    5.5310    0.5503 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9037    4.4857    0.6165 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6103    4.7977    0.9623 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3170    3.2184    0.3369 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4524    2.1728    0.3862 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9175    0.8832    0.0913 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0236   -0.1212    0.1535 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3090   -0.1641    0.4570 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1119   -0.6555   -0.5937 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4455   -0.2897   -0.2402 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.2934   -0.1933   -1.4459 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6098    0.1154   -1.2106 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6491   -0.5987   -0.7210 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5094   -1.7985   -0.4050 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0036    0.0234   -0.5405 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9595   -0.9571    0.0052 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6465   -2.1517    0.2732 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2501   -0.5669    0.2369 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9419   -1.0287    0.9418 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8554   -2.4104    0.8425 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9800   -0.6703    2.1176 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3825   -1.3020    3.2667 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6078   -1.0908    1.6474 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3524   -0.9595    2.6286 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1126   -0.7710   -0.8907 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7098   -1.9670   -1.2028 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0124   -3.1518   -1.2125 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6161   -4.3639   -1.5283 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2603   -5.3208   -0.3267 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9322   -3.8855   -1.4210 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2921   -3.6666    0.3083 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0383   -1.8812   -0.3374 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5754    3.7745   -0.3397 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1610    6.7876   -0.7433 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4825    6.5330    0.7787 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1704    4.1897    1.0556 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4306    2.3576    0.6505 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7383    0.8214    0.6994 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2861    0.7893    0.1374 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8786    0.6500   -2.0997 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1821   -1.1084   -2.1102 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9005    0.8375    0.2093 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3324    0.4786   -1.4872 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.6130   -0.2884    1.1460 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9320   -0.6357    1.2267 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6182   -2.7791    1.3520 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9773    0.4371    2.1855 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9893   -0.7476    3.8280 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6859   -2.1139    1.2453 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1987   -1.6529    3.2978 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6801    0.1623   -0.8873 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7622   -2.0234   -1.4554 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5991   -4.4091   -1.7633 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3 38  2  0
 38 39  1  0
 38 37  1  0
 37 36  2  0
 36  5  1  0
  5  4  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  2  0
 24 26  1  0
 26 27  1  0
 27 29  1  0
 27 28  2  0
 21 30  1  0
 30 31  1  0
 30 32  1  0
 32 33  1  0
 32 34  1  0
 34 35  1  0
 15 13  1  0
 13 14  1  0
 13 12  2  0
 12 10  1  0
 10 11  1  0
 10  9  2  0
  4  3  1  0
 17  6  1  0
 34 19  1  0
  9  8  1  0
  1 40  1  0
  1 41  1  0
  1 42  1  0
 39 64  1  0
 37 63  1  0
 36 62  1  0
  4 43  1  0
 16 48  1  0
 19 49  1  1
 21 50  1  1
 22 51  1  0
 22 52  1  0
 26 53  1  0
 26 54  1  0
 29 55  1  0
 30 56  1  1
 31 57  1  0
 32 58  1  1
 33 59  1  0
 34 60  1  6
 35 61  1  0
 14 47  1  0
 12 46  1  0
 11 45  1  0
  9 44  1  0
M  CHG  1   7   1
M  END

Peonidin 3-O-(6''-malonyl-glucoside)
  Mrv1652310041811352D          

 39 42  0  0  1  0            999 V2000
    0.7145   -4.5375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4289   -4.9499    0.0000 C   0  0  0  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
    2.8579   -4.9499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -5.7750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.9499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0012   -4.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -5.7750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.9499    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -4.5375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4289   -4.9499    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -4.5375    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
   -2.8579   -3.3000    0.0000 C   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
   -4.2868   -3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868   -2.4749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0012   -2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -2.4749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -4.5375    0.0000 O   0  3  0  0  0  0  0  0  0  0  0  0
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   -1.4289   -8.2500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -8.2500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -7.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -3.7125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4289   -3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -3.3000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0000   -2.4749    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -3.7125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4289   -3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  1  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  2  0  0  0  0
  1 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  1  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  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  2  0  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
 20 21  2  0  0  0  0
 15 21  1  0  0  0  0
 21 22  1  0  0  0  0
 16 23  1  0  0  0  0
 23 24  2  0  0  0  0
 13 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  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
 27 30  2  0  0  0  0
 30 31  1  0  0  0  0
 30 32  1  0  0  0  0
 32 33  2  0  0  0  0
 25 33  1  0  0  0  0
 11 34  1  0  0  0  0
 34 35  1  6  0  0  0
 34 36  1  0  0  0  0
 36 37  1  1  0  0  0
 36 38  1  0  0  0  0
  1 38  1  0  0  0  0
 38 39  1  1  0  0  0
M  CHG  1  23   1
M  END
> <DATABASE_ID>
NP0054593

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C(O)C=CC(=C1)C1=[O+]C2=C(C=C1O[C@@H]1O[C@H](COC(=O)CC(O)=O)[C@H](O)[C@H](O)[C@H]1O)C(O)=CC(O)=C2

> <INCHI_IDENTIFIER>
InChI=1S/C25H24O14/c1-35-16-4-10(2-3-13(16)27)24-17(7-12-14(28)5-11(26)6-15(12)37-24)38-25-23(34)22(33)21(32)18(39-25)9-36-20(31)8-19(29)30/h2-7,18,21-23,25,32-34H,8-9H2,1H3,(H3-,26,27,28,29,30)/p+1/t18-,21+,22+,23-,25-/m1/s1

> <INCHI_KEY>
CKJPGRXYFVEMFF-WXOQYFMXSA-O

> <FORMULA>
C25H25O14

> <MOLECULAR_WEIGHT>
549.46

> <EXACT_MASS>
549.123881905

> <JCHEM_ACCEPTOR_COUNT>
13

> <JCHEM_ATOM_COUNT>
64

> <JCHEM_AVERAGE_POLARIZABILITY>
51.94670875013297

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
1

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-{[(2S,3R,4S,5R,6R)-6-{[(2-carboxyacetyl)oxy]methyl}-3,4,5-trihydroxyoxan-2-yl]oxy}-5,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-1lambda4-chromen-1-ylium

> <ALOGPS_LOGP>
1.97

> <JCHEM_LOGP>
0.7072

> <ALOGPS_LOGS>
-3.21

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
6.395844916901775

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.2947376378224624

> <JCHEM_PKA_STRONGEST_BASIC>
-3.649103090718371

> <JCHEM_POLAR_SURFACE_AREA>
225.80999999999997

> <JCHEM_REFRACTIVITY>
136.23540000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.58e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-{[(2S,3R,4S,5R,6R)-6-{[(2-carboxyacetyl)oxy]methyl}-3,4,5-trihydroxyoxan-2-yl]oxy}-5,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-1lambda4-chromen-1-ylium

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-OCT-18   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: Peonidin 3-O-(6''-malonyl-glucoside)              
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-OCT-18         0                                  
HETATM    1  C   UNK     0       1.334  -8.470   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.667  -9.240   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       4.001  -8.470   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       5.335  -9.240   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       5.335 -10.780   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       6.668  -8.470   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.002  -9.240   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       9.336  -8.470   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0       8.002 -10.780   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0       0.000  -9.240   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      -1.334  -8.470   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -2.667  -9.240   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      -4.001  -8.470   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -4.001  -6.930   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -5.335  -6.160   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -6.668  -6.930   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -8.002  -6.160   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -8.002  -4.620   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -9.336  -3.850   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      -6.668  -3.850   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      -4.001  -3.850   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      -6.668  -8.470   0.000  0.00  0.00           O+1
HETATM   24  C   UNK     0      -5.335  -9.240   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -5.335 -10.780   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -4.001 -11.550   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -4.001 -13.090   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      -2.667 -13.860   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      -2.667 -15.400   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -5.335 -13.860   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      -5.335 -15.400   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      -6.668 -13.090   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -6.668 -11.550   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      -1.334  -6.930   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0      -2.667  -6.160   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0       0.000  -6.160   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0       0.000  -4.620   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0       2.667  -6.160   0.000  0.00  0.00           O+0
CONECT    1    2   10   38                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7                                                            
CONECT   10    1   11                                                       
CONECT   11   10   12   34                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   24                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   21                                                  
CONECT   16   15   17   23                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21                                                       
CONECT   21   20   15   22                                                  
CONECT   22   21                                                            
CONECT   23   16   24                                                       
CONECT   24   23   13   25                                                  
CONECT   25   24   26   33                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28   30                                                  
CONECT   28   27   29                                                       
CONECT   29   28                                                            
CONECT   30   27   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30   33                                                       
CONECT   33   32   25                                                       
CONECT   34   11   35   36                                                  
CONECT   35   34                                                            
CONECT   36   34   37   38                                                  
CONECT   37   36                                                            
CONECT   38   36    1   39                                                  
CONECT   39   38                                                            
MASTER        0    0    0    0    0    0    0    0   39    0   84    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₅H₂₅O₁₄

Average Mass

549.4600 Da

Monoisotopic Mass

549.12388 Da

IUPAC Name

3-{[(2S,3R,4S,5R,6R)-6-{[(2-carboxyacetyl)oxy]methyl}-3,4,5-trihydroxyoxan-2-yl]oxy}-5,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-1lambda4-chromen-1-ylium

Traditional Name

3-{[(2S,3R,4S,5R,6R)-6-{[(2-carboxyacetyl)oxy]methyl}-3,4,5-trihydroxyoxan-2-yl]oxy}-5,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-1lambda4-chromen-1-ylium

CAS Registry Number

Not Available

SMILES

COC1=C(O)C=CC(=C1)C1=[O+]C2=C(C=C1O[C@@H]1O[C@H](COC(=O)CC(O)=O)[C@H](O)[C@H](O)[C@H]1O)C(O)=CC(O)=C2

InChI Identifier

InChI=1S/C25H24O14/c1-35-16-4-10(2-3-13(16)27)24-17(7-12-14(28)5-11(26)6-15(12)37-24)38-25-23(34)22(33)21(32)18(39-25)9-36-20(31)8-19(29)30/h2-7,18,21-23,25,32-34H,8-9H2,1H3,(H3-,26,27,28,29,30)/p+1/t18-,21+,22+,23-,25-/m1/s1

InChI Key

CKJPGRXYFVEMFF-WXOQYFMXSA-O

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
Alopecurus spp.	Plant	KNApSAcK
Anthoxanthum spp.	Plant	KNApSAcK
Avenula spp.	Plant	KNApSAcK
Bothriochloa spp.	Plant	KNApSAcK
Dactylis spp.	Plant	KNApSAcK
Deschampsia spp.	Plant	KNApSAcK
Elymus spp.	Plant	KNApSAcK
Festuca spp.	Plant	KNApSAcK
Hibiscus syriacus	Plant	KNApSAcK
Hordeum spp.	Plant	KNApSAcK
Miscanthus spp.	Plant	KNApSAcK
Molinia spp.	Plant	KNApSAcK
Oryza spp.	Plant	KNApSAcK
Phalaris spp.	Plant	KNApSAcK
Phleum spp.	Plant	KNApSAcK
Poa spp.	Plant	KNApSAcK
Sinarundinaria spp.	Plant	KNApSAcK

Chemical Taxonomy

Classification

Not classified

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	1.97	ALOGPS
logP	0.71	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	3.29	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	13	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	225.81 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	136.24 m³·mol⁻¹	ChemAxon
Polarizability	51.95 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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Peonidin 3-(6''-malonylglucoside) (NP0054593)

MOL for NP0054593 (Peonidin 3-(6''-malonylglucoside))

3D MOL for NP0054593 (Peonidin 3-(6''-malonylglucoside))

3D SDF for NP0054593 (Peonidin 3-(6''-malonylglucoside))

3D-SDF for NP0054593 (Peonidin 3-(6''-malonylglucoside))

PDB for NP0054593 (Peonidin 3-(6''-malonylglucoside))

3D PDB for NP0054593 (Peonidin 3-(6''-malonylglucoside))

SMILES for NP0054593 (Peonidin 3-(6''-malonylglucoside))

INCHI for NP0054593 (Peonidin 3-(6''-malonylglucoside))

Structure for NP0054593 (Peonidin 3-(6''-malonylglucoside))

3D Structure for NP0054593 (Peonidin 3-(6''-malonylglucoside))