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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2021-09-23 03:19:07 UTC

Update Date

2021-09-23 03:19:07 UTC

HMDB ID

HMDB0301882

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Apigeninidin 5-(5''-caffeylarabinoside)

Description

Apigeninidin 5-(5''-caffeylarabinoside) is a member of the class of compounds known as anthocyanidin-5-o-glycosides. Anthocyanidin-5-o-glycosides are phenolic compounds containing one anthocyanidin moiety which is O-glycosidically linked to a carbohydrate moiety at the C5-position. Apigeninidin 5-(5''-caffeylarabinoside) is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Apigeninidin 5-(5''-caffeylarabinoside) can be found in sorghum, which makes apigeninidin 5-(5''-caffeylarabinoside) a potential biomarker for the consumption of this food product.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI


  Mrv0541 02241212172D          

 40 44  0  0  0  0            999 V2000
   -0.7661    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4805    2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4805    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7661    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0516    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0516    2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6629    3.3000    0.0000 O   0  3  0  0  0  0  0  0  0  0  0  0
    0.6629    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3773    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3773    2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0918    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8063    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0918    4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8063    2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5207    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5207    4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1950    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2352    4.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2181    1.0550    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8856    0.5701    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.6306   -0.2145    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.8056   -0.2145    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5507    0.5701    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3207   -0.8820    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1155   -0.8820    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6702    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7661    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7122    4.3980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4267    3.9855    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4267    3.1605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7122    2.7479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9977    3.1605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9977    3.9855    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7122    1.9229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9977    1.5104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9977    0.6854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2833    0.2729    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7122    0.2729    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1411    4.3980    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7122    5.2230    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  6  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  7  6  1  0  0  0  0
  5  6  2  0  0  0  0
  5  8  1  0  0  0  0
  7 10  2  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 13 11  2  0  0  0  0
 11 14  1  0  0  0  0
 12 13  1  0  0  0  0
 12 16  2  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
  2 17  1  0  0  0  0
 16 18  1  0  0  0  0
 19 20  1  0  0  0  0
 19 23  1  0  0  0  0
 20 21  1  0  0  0  0
 20 26  1  6  0  0  0
 21 22  1  0  0  0  0
 21 25  1  1  0  0  0
 22 23  1  0  0  0  0
 22 24  1  6  0  0  0
 23 27  1  1  0  0  0
  4 27  1  0  0  0  0
 28 29  2  0  0  0  0
 28 33  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
 31 32  1  0  0  0  0
 32 33  2  0  0  0  0
 31 34  1  0  0  0  0
 34 35  2  0  0  0  0
 35 36  1  0  0  0  0
 36 37  1  0  0  0  0
 36 38  2  0  0  0  0
 26 37  1  0  0  0  0
 29 39  1  0  0  0  0
 28 40  1  0  0  0  0
M  CHG  1   7   1
M  END

HMDB0301882
     RDKit          3D
Apigeninidin 5-(5''-caffeylarabinoside)
 65 69  0  0  0  0  0  0  0  0999 V2000
    5.1272    2.1886   -3.0774 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8714    1.6222   -1.9904 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9881    1.1652   -1.1735 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7056    0.5722   -0.0343 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7205    0.0597    0.8925 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3443   -0.5492    2.0693 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2592   -1.0395    2.9581 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5991   -0.9255    2.6765 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5500   -1.4188    3.5693 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.9876   -0.3179    1.5017 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3382   -0.1992    1.2107 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.0433    0.1814    0.5972 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5529    1.4511   -1.6053 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5443    1.9328   -2.4736 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1550    1.6530   -1.8843 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9578    0.3163   -1.7040 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1759   -0.0943   -2.3955 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3036   -0.0804   -1.6039 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1187   -1.1413   -1.2448 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9287   -2.4475   -1.6378 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8200   -3.4253   -1.2090 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5612   -4.7290   -1.6495 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8921   -3.1304   -0.4003 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1055   -1.8134    0.0112 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1290   -1.5369    0.7821 O   0  0  0  0  0  3  0  0  0  0  0  0
   -5.3689   -0.3070    1.1948 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5099   -0.0170    2.0504 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3405   -1.0810    2.4178 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4445   -0.9254    3.2207 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7800    0.3288    3.7065 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.9018    0.4735    4.5195 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9788    1.3817    3.3574 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8646    1.2076    2.5438 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5378    0.7194    0.8178 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4553    0.4324    0.0035 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2207   -0.8543   -0.4168 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2450    0.8546   -3.5741 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7090    0.5227   -4.5101 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1610    2.1631   -2.8875 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9176    2.7600   -2.2483 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0042    1.3089   -1.4928 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6593    0.4420    0.2608 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2824   -0.6393    2.2920 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9207   -1.5106    3.8708 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.5330   -1.3388    3.3696 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.6487    0.2425    0.3552 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4405    0.6445   -0.3032 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6017    3.0369   -2.5882 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6148    1.5037   -3.4939 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1328    2.2143   -0.9252 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0351   -1.1213   -2.7469 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0936   -2.6832   -2.2688 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0001   -4.9842   -2.5276 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5734   -3.9340   -0.0837 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1175   -2.0858    2.0605 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0859   -1.7473    3.5043 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.8260    0.6679    4.1608 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2091    2.3634    3.7151 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2570    2.0638    2.2908 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7039    1.7660    1.1425 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7761    1.2028   -0.3180 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2400    0.9183   -4.0236 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2616    0.3464   -5.3914 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6088    2.8446   -3.6372 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8754    2.5254   -1.2756 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 10 12  2  0
  2 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  1  0
 21 23  2  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  1  0
 27 28  2  0
 28 29  1  0
 29 30  2  0
 30 31  1  0
 30 32  1  0
 32 33  2  0
 26 34  2  0
 34 35  1  0
 35 36  2  0
 17 37  1  0
 37 38  1  0
 37 39  1  0
 39 40  1  0
 12  5  1  0
 39 15  1  0
 36 19  1  0
 36 24  1  0
 33 27  1  0
  3 41  1  0
  4 42  1  0
  6 43  1  0
  7 44  1  0
  9 45  1  0
 11 46  1  0
 12 47  1  0
 14 48  1  0
 14 49  1  0
 15 50  1  1
 17 51  1  6
 20 52  1  0
 22 53  1  0
 23 54  1  0
 28 55  1  0
 29 56  1  0
 31 57  1  0
 32 58  1  0
 33 59  1  0
 34 60  1  0
 35 61  1  0
 37 62  1  6
 38 63  1  0
 39 64  1  6
 40 65  1  0
M  CHG  1  25   1
M  END


  Mrv0541 02241212172D          

 40 44  0  0  0  0            999 V2000
   -0.7661    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4805    2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4805    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7661    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0516    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0516    2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6629    3.3000    0.0000 O   0  3  0  0  0  0  0  0  0  0  0  0
    0.6629    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3773    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3773    2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0918    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8063    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0918    4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8063    2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5207    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5207    4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1950    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2352    4.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2181    1.0550    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8856    0.5701    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.6306   -0.2145    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.8056   -0.2145    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5507    0.5701    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3207   -0.8820    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1155   -0.8820    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6702    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7661    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7122    4.3980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4267    3.9855    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4267    3.1605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7122    2.7479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9977    3.1605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9977    3.9855    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7122    1.9229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9977    1.5104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9977    0.6854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2833    0.2729    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7122    0.2729    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1411    4.3980    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7122    5.2230    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  6  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  7  6  1  0  0  0  0
  5  6  2  0  0  0  0
  5  8  1  0  0  0  0
  7 10  2  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 13 11  2  0  0  0  0
 11 14  1  0  0  0  0
 12 13  1  0  0  0  0
 12 16  2  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
  2 17  1  0  0  0  0
 16 18  1  0  0  0  0
 19 20  1  0  0  0  0
 19 23  1  0  0  0  0
 20 21  1  0  0  0  0
 20 26  1  6  0  0  0
 21 22  1  0  0  0  0
 21 25  1  1  0  0  0
 22 23  1  0  0  0  0
 22 24  1  6  0  0  0
 23 27  1  1  0  0  0
  4 27  1  0  0  0  0
 28 29  2  0  0  0  0
 28 33  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
 31 32  1  0  0  0  0
 32 33  2  0  0  0  0
 31 34  1  0  0  0  0
 34 35  2  0  0  0  0
 35 36  1  0  0  0  0
 36 37  1  0  0  0  0
 36 38  2  0  0  0  0
 26 37  1  0  0  0  0
 29 39  1  0  0  0  0
 28 40  1  0  0  0  0
M  CHG  1   7   1
M  END
> <DATABASE_ID>
HMDB0301882

> <DATABASE_NAME>
hmdb

> <SMILES>
O[C@H]1[C@H](COC(=O)\C=C\C2=CC(O)=C(O)C=C2)O[C@@H](OC2=CC(O)=CC3=C2C=CC(=[O+]3)C2=CC=C(O)C=C2)[C@@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C29H24O11/c30-17-5-3-16(4-6-17)22-9-7-19-23(38-22)12-18(31)13-24(19)39-29-28(36)27(35)25(40-29)14-37-26(34)10-2-15-1-8-20(32)21(33)11-15/h1-13,25,27-29,35-36H,14H2,(H3-,30,31,32,33,34)/p+1/t25-,27-,28+,29+/m0/s1

> <INCHI_KEY>
BBZCRSFPHPHYKT-ANHREMPLSA-O

> <FORMULA>
C29H25O11

> <MOLECULAR_WEIGHT>
549.5022

> <EXACT_MASS>
549.139686642

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_AVERAGE_POLARIZABILITY>
55.98315905529735

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
1

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
5-{[(2S,3R,4R,5S)-5-({[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}methyl)-3,4-dihydroxyoxolan-2-yl]oxy}-7-hydroxy-2-(4-hydroxyphenyl)-1λ⁴-chromen-1-ylium

> <ALOGPS_LOGP>
3.85

> <JCHEM_LOGP>
4.7576

> <ALOGPS_LOGS>
-4.87

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.458595049473091

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.841584862351974

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6803150134013283

> <JCHEM_POLAR_SURFACE_AREA>
179.28

> <JCHEM_REFRACTIVITY>
149.86270000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
7.86e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5-{[(2S,3R,4R,5S)-5-({[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}methyl)-3,4-dihydroxyoxolan-2-yl]oxy}-7-hydroxy-2-(4-hydroxyphenyl)-1λ⁴-chromen-1-ylium

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0301882
     RDKit          3D
Apigeninidin 5-(5''-caffeylarabinoside)
 65 69  0  0  0  0  0  0  0  0999 V2000
    5.1272    2.1886   -3.0774 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8714    1.6222   -1.9904 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9881    1.1652   -1.1735 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7056    0.5722   -0.0343 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7205    0.0597    0.8925 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3443   -0.5492    2.0693 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2592   -1.0395    2.9581 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5991   -0.9255    2.6765 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5500   -1.4188    3.5693 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.9876   -0.3179    1.5017 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3382   -0.1992    1.2107 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.0433    0.1814    0.5972 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5529    1.4511   -1.6053 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5443    1.9328   -2.4736 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1550    1.6530   -1.8843 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9578    0.3163   -1.7040 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1759   -0.0943   -2.3955 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3036   -0.0804   -1.6039 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1187   -1.1413   -1.2448 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9287   -2.4475   -1.6378 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8200   -3.4253   -1.2090 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5612   -4.7290   -1.6495 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8921   -3.1304   -0.4003 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1055   -1.8134    0.0112 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1290   -1.5369    0.7821 O   0  0  0  0  0  3  0  0  0  0  0  0
   -5.3689   -0.3070    1.1948 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5099   -0.0170    2.0504 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3405   -1.0810    2.4178 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4445   -0.9254    3.2207 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7800    0.3288    3.7065 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.9018    0.4735    4.5195 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9788    1.3817    3.3574 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8646    1.2076    2.5438 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5378    0.7194    0.8178 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4553    0.4324    0.0035 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2207   -0.8543   -0.4168 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2450    0.8546   -3.5741 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7090    0.5227   -4.5101 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1610    2.1631   -2.8875 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9176    2.7600   -2.2483 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0042    1.3089   -1.4928 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6593    0.4420    0.2608 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2824   -0.6393    2.2920 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9207   -1.5106    3.8708 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.5330   -1.3388    3.3696 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.6487    0.2425    0.3552 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4405    0.6445   -0.3032 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6017    3.0369   -2.5882 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6148    1.5037   -3.4939 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1328    2.2143   -0.9252 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0351   -1.1213   -2.7469 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0936   -2.6832   -2.2688 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0001   -4.9842   -2.5276 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5734   -3.9340   -0.0837 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1175   -2.0858    2.0605 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0859   -1.7473    3.5043 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.8260    0.6679    4.1608 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2091    2.3634    3.7151 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2570    2.0638    2.2908 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7039    1.7660    1.1425 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7761    1.2028   -0.3180 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2400    0.9183   -4.0236 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2616    0.3464   -5.3914 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6088    2.8446   -3.6372 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8754    2.5254   -1.2756 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 10 12  2  0
  2 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  1  0
 21 23  2  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  1  0
 27 28  2  0
 28 29  1  0
 29 30  2  0
 30 31  1  0
 30 32  1  0
 32 33  2  0
 26 34  2  0
 34 35  1  0
 35 36  2  0
 17 37  1  0
 37 38  1  0
 37 39  1  0
 39 40  1  0
 12  5  1  0
 39 15  1  0
 36 19  1  0
 36 24  1  0
 33 27  1  0
  3 41  1  0
  4 42  1  0
  6 43  1  0
  7 44  1  0
  9 45  1  0
 11 46  1  0
 12 47  1  0
 14 48  1  0
 14 49  1  0
 15 50  1  1
 17 51  1  6
 20 52  1  0
 22 53  1  0
 23 54  1  0
 28 55  1  0
 29 56  1  0
 31 57  1  0
 32 58  1  0
 33 59  1  0
 34 60  1  0
 35 61  1  0
 37 62  1  6
 38 63  1  0
 39 64  1  6
 40 65  1  0
M  CHG  1  25   1
M  END

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      -1.430   6.160   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.764   5.390   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.764   3.850   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.430   3.080   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.096   3.850   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.096   5.390   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       1.237   6.160   0.000  0.00  0.00           O+1
HETATM    8  C   UNK     0       1.237   3.080   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.571   3.850   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.571   5.390   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.905   6.160   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.238   8.470   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.905   7.700   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.238   5.390   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.572   6.160   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.572   7.700   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -4.097   6.160   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       7.906   8.470   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      -4.140   1.969   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      -5.386   1.064   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -4.910  -0.400   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -3.370  -0.400   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -2.895   1.064   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      -2.465  -1.646   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0      -5.816  -1.646   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      -6.851   1.540   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      -1.430   1.540   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0     -10.663   8.210   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0     -11.997   7.440   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0     -11.997   5.900   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0     -10.663   5.129   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -9.329   5.900   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -9.329   7.440   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0     -10.663   3.589   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      -9.329   2.819   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      -9.329   1.279   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0      -7.995   0.509   0.000  0.00  0.00           O+0
HETATM   38  O   UNK     0     -10.663   0.509   0.000  0.00  0.00           O+0
HETATM   39  O   UNK     0     -13.330   8.210   0.000  0.00  0.00           O+0
HETATM   40  O   UNK     0     -10.663   9.750   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3   17                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   27                                                  
CONECT    5    4    6    8                                                  
CONECT    6    1    7    5                                                  
CONECT    7    6   10                                                       
CONECT    8    5    9                                                       
CONECT    9    8   10                                                       
CONECT   10    7    9   11                                                  
CONECT   11   10   13   14                                                  
CONECT   12   13   16                                                       
CONECT   13   11   12                                                       
CONECT   14   11   15                                                       
CONECT   15   14   16                                                       
CONECT   16   12   15   18                                                  
CONECT   17    2                                                            
CONECT   18   16                                                            
CONECT   19   20   23                                                       
CONECT   20   19   21   26                                                  
CONECT   21   20   22   25                                                  
CONECT   22   21   23   24                                                  
CONECT   23   19   22   27                                                  
CONECT   24   22                                                            
CONECT   25   21                                                            
CONECT   26   20   37                                                       
CONECT   27   23    4                                                       
CONECT   28   29   33   40                                                  
CONECT   29   28   30   39                                                  
CONECT   30   29   31                                                       
CONECT   31   30   32   34                                                  
CONECT   32   31   33                                                       
CONECT   33   28   32                                                       
CONECT   34   31   35                                                       
CONECT   35   34   36                                                       
CONECT   36   35   37   38                                                  
CONECT   37   36   26                                                       
CONECT   38   36                                                            
CONECT   39   29                                                            
CONECT   40   28                                                            
MASTER        0    0    0    0    0    0    0    0   40    0   88    0
END

COMPND    HMDB0301882
HETATM    1  O1  UNL     1       5.127   2.189  -3.077  1.00  0.00           O  
HETATM    2  C1  UNL     1       4.871   1.622  -1.990  1.00  0.00           C  
HETATM    3  C2  UNL     1       5.988   1.165  -1.173  1.00  0.00           C  
HETATM    4  C3  UNL     1       5.706   0.572  -0.034  1.00  0.00           C  
HETATM    5  C4  UNL     1       6.720   0.060   0.892  1.00  0.00           C  
HETATM    6  C5  UNL     1       6.344  -0.549   2.069  1.00  0.00           C  
HETATM    7  C6  UNL     1       7.259  -1.040   2.958  1.00  0.00           C  
HETATM    8  C7  UNL     1       8.599  -0.925   2.676  1.00  0.00           C  
HETATM    9  O2  UNL     1       9.550  -1.419   3.569  1.00  0.00           O  
HETATM   10  C8  UNL     1       8.988  -0.318   1.502  1.00  0.00           C  
HETATM   11  O3  UNL     1      10.338  -0.199   1.211  1.00  0.00           O  
HETATM   12  C9  UNL     1       8.043   0.181   0.597  1.00  0.00           C  
HETATM   13  O4  UNL     1       3.553   1.451  -1.605  1.00  0.00           O  
HETATM   14  C10 UNL     1       2.544   1.933  -2.474  1.00  0.00           C  
HETATM   15  C11 UNL     1       1.155   1.653  -1.884  1.00  0.00           C  
HETATM   16  O5  UNL     1       0.958   0.316  -1.704  1.00  0.00           O  
HETATM   17  C12 UNL     1      -0.176  -0.094  -2.396  1.00  0.00           C  
HETATM   18  O6  UNL     1      -1.304  -0.080  -1.604  1.00  0.00           O  
HETATM   19  C13 UNL     1      -2.119  -1.141  -1.245  1.00  0.00           C  
HETATM   20  C14 UNL     1      -1.929  -2.448  -1.638  1.00  0.00           C  
HETATM   21  C15 UNL     1      -2.820  -3.425  -1.209  1.00  0.00           C  
HETATM   22  O7  UNL     1      -2.561  -4.729  -1.650  1.00  0.00           O  
HETATM   23  C16 UNL     1      -3.892  -3.130  -0.400  1.00  0.00           C  
HETATM   24  C17 UNL     1      -4.106  -1.813   0.011  1.00  0.00           C  
HETATM   25  O8  UNL     1      -5.129  -1.537   0.782  1.00  0.00           O1+
HETATM   26  C18 UNL     1      -5.369  -0.307   1.195  1.00  0.00           C  
HETATM   27  C19 UNL     1      -6.510  -0.017   2.050  1.00  0.00           C  
HETATM   28  C20 UNL     1      -7.341  -1.081   2.418  1.00  0.00           C  
HETATM   29  C21 UNL     1      -8.444  -0.925   3.221  1.00  0.00           C  
HETATM   30  C22 UNL     1      -8.780   0.329   3.706  1.00  0.00           C  
HETATM   31  O9  UNL     1      -9.902   0.473   4.520  1.00  0.00           O  
HETATM   32  C23 UNL     1      -7.979   1.382   3.357  1.00  0.00           C  
HETATM   33  C24 UNL     1      -6.865   1.208   2.544  1.00  0.00           C  
HETATM   34  C25 UNL     1      -4.538   0.719   0.818  1.00  0.00           C  
HETATM   35  C26 UNL     1      -3.455   0.432   0.004  1.00  0.00           C  
HETATM   36  C27 UNL     1      -3.221  -0.854  -0.417  1.00  0.00           C  
HETATM   37  C28 UNL     1      -0.245   0.855  -3.574  1.00  0.00           C  
HETATM   38  O10 UNL     1       0.709   0.523  -4.510  1.00  0.00           O  
HETATM   39  C29 UNL     1       0.161   2.163  -2.888  1.00  0.00           C  
HETATM   40  O11 UNL     1      -0.918   2.760  -2.248  1.00  0.00           O  
HETATM   41  H1  UNL     1       7.004   1.309  -1.493  1.00  0.00           H  
HETATM   42  H2  UNL     1       4.659   0.442   0.261  1.00  0.00           H  
HETATM   43  H3  UNL     1       5.282  -0.639   2.292  1.00  0.00           H  
HETATM   44  H4  UNL     1       6.921  -1.511   3.871  1.00  0.00           H  
HETATM   45  H5  UNL     1      10.533  -1.339   3.370  1.00  0.00           H  
HETATM   46  H6  UNL     1      10.649   0.242   0.355  1.00  0.00           H  
HETATM   47  H7  UNL     1       8.441   0.645  -0.303  1.00  0.00           H  
HETATM   48  H8  UNL     1       2.602   3.037  -2.588  1.00  0.00           H  
HETATM   49  H9  UNL     1       2.615   1.504  -3.494  1.00  0.00           H  
HETATM   50  H10 UNL     1       1.133   2.214  -0.925  1.00  0.00           H  
HETATM   51  H11 UNL     1       0.035  -1.121  -2.747  1.00  0.00           H  
HETATM   52  H12 UNL     1      -1.094  -2.683  -2.269  1.00  0.00           H  
HETATM   53  H13 UNL     1      -3.000  -4.984  -2.528  1.00  0.00           H  
HETATM   54  H14 UNL     1      -4.573  -3.934  -0.084  1.00  0.00           H  
HETATM   55  H15 UNL     1      -7.118  -2.086   2.060  1.00  0.00           H  
HETATM   56  H16 UNL     1      -9.086  -1.747   3.504  1.00  0.00           H  
HETATM   57  H17 UNL     1     -10.826   0.668   4.161  1.00  0.00           H  
HETATM   58  H18 UNL     1      -8.209   2.363   3.715  1.00  0.00           H  
HETATM   59  H19 UNL     1      -6.257   2.064   2.291  1.00  0.00           H  
HETATM   60  H20 UNL     1      -4.704   1.766   1.142  1.00  0.00           H  
HETATM   61  H21 UNL     1      -2.776   1.203  -0.318  1.00  0.00           H  
HETATM   62  H22 UNL     1      -1.240   0.918  -4.024  1.00  0.00           H  
HETATM   63  H23 UNL     1       0.262   0.346  -5.391  1.00  0.00           H  
HETATM   64  H24 UNL     1       0.609   2.845  -3.637  1.00  0.00           H  
HETATM   65  H25 UNL     1      -0.875   2.525  -1.276  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3   13
CONECT    3    4    4   41
CONECT    4    5   42
CONECT    5    6    6   12
CONECT    6    7   43
CONECT    7    8    8   44
CONECT    8    9   10
CONECT    9   45
CONECT   10   11   12   12
CONECT   11   46
CONECT   12   47
CONECT   13   14
CONECT   14   15   48   49
CONECT   15   16   39   50
CONECT   16   17
CONECT   17   18   37   51
CONECT   18   19
CONECT   19   20   20   36
CONECT   20   21   52
CONECT   21   22   23   23
CONECT   22   53
CONECT   23   24   54
CONECT   24   25   25   36
CONECT   25   26
CONECT   26   27   34   34
CONECT   27   28   28   33
CONECT   28   29   55
CONECT   29   30   30   56
CONECT   30   31   32
CONECT   31   57
CONECT   32   33   33   58
CONECT   33   59
CONECT   34   35   60
CONECT   35   36   36   61
CONECT   37   38   39   62
CONECT   38   63
CONECT   39   40   64
CONECT   40   65
END

HMDB0301882
     RDKit          3D
Apigeninidin 5-(5''-caffeylarabinoside)
 65 69  0  0  0  0  0  0  0  0999 V2000
    5.1272    2.1886   -3.0774 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8714    1.6222   -1.9904 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9881    1.1652   -1.1735 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7056    0.5722   -0.0343 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7205    0.0597    0.8925 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3443   -0.5492    2.0693 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2592   -1.0395    2.9581 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5991   -0.9255    2.6765 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5500   -1.4188    3.5693 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.9876   -0.3179    1.5017 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3382   -0.1992    1.2107 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.0433    0.1814    0.5972 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5529    1.4511   -1.6053 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5443    1.9328   -2.4736 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1550    1.6530   -1.8843 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9578    0.3163   -1.7040 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1759   -0.0943   -2.3955 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3036   -0.0804   -1.6039 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1187   -1.1413   -1.2448 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9287   -2.4475   -1.6378 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8200   -3.4253   -1.2090 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5612   -4.7290   -1.6495 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8921   -3.1304   -0.4003 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1055   -1.8134    0.0112 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1290   -1.5369    0.7821 O   0  0  0  0  0  3  0  0  0  0  0  0
   -5.3689   -0.3070    1.1948 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5099   -0.0170    2.0504 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3405   -1.0810    2.4178 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4445   -0.9254    3.2207 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7800    0.3288    3.7065 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.9018    0.4735    4.5195 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9788    1.3817    3.3574 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8646    1.2076    2.5438 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5378    0.7194    0.8178 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4553    0.4324    0.0035 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2207   -0.8543   -0.4168 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2450    0.8546   -3.5741 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7090    0.5227   -4.5101 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1610    2.1631   -2.8875 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9176    2.7600   -2.2483 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0042    1.3089   -1.4928 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6593    0.4420    0.2608 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2824   -0.6393    2.2920 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9207   -1.5106    3.8708 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.5330   -1.3388    3.3696 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.6487    0.2425    0.3552 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4405    0.6445   -0.3032 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6017    3.0369   -2.5882 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6148    1.5037   -3.4939 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1328    2.2143   -0.9252 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0351   -1.1213   -2.7469 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0936   -2.6832   -2.2688 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0001   -4.9842   -2.5276 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5734   -3.9340   -0.0837 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1175   -2.0858    2.0605 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0859   -1.7473    3.5043 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.8260    0.6679    4.1608 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2091    2.3634    3.7151 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2570    2.0638    2.2908 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7039    1.7660    1.1425 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7761    1.2028   -0.3180 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2400    0.9183   -4.0236 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2616    0.3464   -5.3914 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6088    2.8446   -3.6372 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8754    2.5254   -1.2756 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 10 12  2  0
  2 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  1  0
 21 23  2  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  1  0
 27 28  2  0
 28 29  1  0
 29 30  2  0
 30 31  1  0
 30 32  1  0
 32 33  2  0
 26 34  2  0
 34 35  1  0
 35 36  2  0
 17 37  1  0
 37 38  1  0
 37 39  1  0
 39 40  1  0
 12  5  1  0
 39 15  1  0
 36 19  1  0
 36 24  1  0
 33 27  1  0
  3 41  1  0
  4 42  1  0
  6 43  1  0
  7 44  1  0
  9 45  1  0
 11 46  1  0
 12 47  1  0
 14 48  1  0
 14 49  1  0
 15 50  1  1
 17 51  1  6
 20 52  1  0
 22 53  1  0
 23 54  1  0
 28 55  1  0
 29 56  1  0
 31 57  1  0
 32 58  1  0
 33 59  1  0
 34 60  1  0
 35 61  1  0
 37 62  1  6
 38 63  1  0
 39 64  1  6
 40 65  1  0
M  CHG  1  25   1
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₂₉H₂₅O₁₁

Average Molecular Weight

549.5022

Monoisotopic Molecular Weight

549.139686642

IUPAC Name

5-{[(2S,3R,4R,5S)-5-({[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}methyl)-3,4-dihydroxyoxolan-2-yl]oxy}-7-hydroxy-2-(4-hydroxyphenyl)-1λ⁴-chromen-1-ylium

Traditional Name

5-{[(2S,3R,4R,5S)-5-({[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}methyl)-3,4-dihydroxyoxolan-2-yl]oxy}-7-hydroxy-2-(4-hydroxyphenyl)-1λ⁴-chromen-1-ylium

CAS Registry Number

Not Available

SMILES

O[C@H]1[C@H](COC(=O)\C=C\C2=CC(O)=C(O)C=C2)O[C@@H](OC2=CC(O)=CC3=C2C=CC(=[O+]3)C2=CC=C(O)C=C2)[C@@H]1O

InChI Identifier

InChI=1S/C29H24O11/c30-17-5-3-16(4-6-17)22-9-7-19-23(38-22)12-18(31)13-24(19)39-29-28(36)27(35)25(40-29)14-37-26(34)10-2-15-1-8-20(32)21(33)11-15/h1-13,25,27-29,35-36H,14H2,(H3-,30,31,32,33,34)/p+1/t25-,27-,28+,29+/m0/s1

InChI Key

BBZCRSFPHPHYKT-ANHREMPLSA-O

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as anthocyanidin-5-o-glycosides. These are phenolic compounds containing one anthocyanidin moiety which is O-glycosidically linked to a carbohydrate moiety at the C5-position.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavonoid glycosides

Direct Parent

Anthocyanidin-5-O-glycosides

Alternative Parents

Substituents

Anthocyanidin-5-o-glycoside
Hydroxyflavonoid
4'-hydroxyflavonoid
7-hydroxyflavonoid
Anthocyanidin
Phenolic glycoside
Hydroxycinnamic acid or derivatives
Cinnamic acid ester
Coumaric acid or derivatives
Cinnamic acid or derivatives
O-glycosyl compound
Glycosyl compound
1-benzopyran
Pentose monosaccharide
Benzopyran
Catechol
Styrene
1-hydroxy-4-unsubstituted benzenoid
Fatty acid ester
Phenol
1-hydroxy-2-unsubstituted benzenoid
Benzenoid
Monosaccharide
Fatty acyl
Monocyclic benzene moiety
Heteroaromatic compound
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Tetrahydrofuran
Carboxylic acid ester
1,2-diol
Secondary alcohol
Carboxylic acid derivative
Organoheterocyclic compound
Oxacycle
Acetal
Monocarboxylic acid or derivatives
Organic oxide
Organic oxygen compound
Carbonyl group
Hydrocarbon derivative
Alcohol
Organooxygen compound
Organic cation
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Cereal and cereal product

Cereal

Sorghum (FooDB: FOOD00177)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular 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

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	3.85	ALOGPS
logP	4.76	ChemAxon
logS	-4.9	ALOGPS
pKa (Strongest Acidic)	6.84	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	179.28 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	149.86 m³·mol⁻¹	ChemAxon
Polarizability	55.98 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

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
AllCCS	[M+H]+	227.561	32859911
AllCCS	[M+H-H2O]+	225.99	32859911
AllCCS	[M+Na]+	229.39	32859911
AllCCS	[M+NH4]+	228.986	32859911
AllCCS	[M-H]-	217.3	32859911
AllCCS	[M+Na-2H]-	218.438	32859911
AllCCS	[M+HCOO]-	219.845	32859911
DeepCCS	[M+H]+	221.43	30932474
DeepCCS	[M-H]-	219.278	30932474
DeepCCS	[M-2H]-	252.518	30932474
DeepCCS	[M+Na]+	227.237	30932474

Predicted Kovats Retention Indices

Not Available

Spectra

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Apigeninidin 5-(5''-caffeylarabinoside) 10V, Positive-QTOF	splash10-0udi-0000090000-a57cba00c590d5024cb3	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Apigeninidin 5-(5''-caffeylarabinoside) 20V, Positive-QTOF	splash10-0a4i-0000090000-3e15c0392461319266d3	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Apigeninidin 5-(5''-caffeylarabinoside) 40V, Positive-QTOF	splash10-0lei-0770950000-061e101e3b0aaa176c01	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Apigeninidin 5-(5''-caffeylarabinoside) 10V, Negative-QTOF	splash10-0002-0000090000-f9407df7d5e9b82dd1e3	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Apigeninidin 5-(5''-caffeylarabinoside) 20V, Negative-QTOF	splash10-0002-0000090000-ee39c1c820e88bd6fd25	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Apigeninidin 5-(5''-caffeylarabinoside) 40V, Negative-QTOF	splash10-0pvi-9861060000-295d17d72b481af0f3fc	2016-08-03	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB001569

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

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Showing metabocard for Apigeninidin 5-(5''-caffeylarabinoside) (HMDB0301882)

MOL for HMDB0301882 (Apigeninidin 5-(5''-caffeylarabinoside))

3D MOL for HMDB0301882 (Apigeninidin 5-(5''-caffeylarabinoside))

3D SDF for HMDB0301882 (Apigeninidin 5-(5''-caffeylarabinoside))

3D-SDF for HMDB0301882 (Apigeninidin 5-(5''-caffeylarabinoside))

PDB for HMDB0301882 (Apigeninidin 5-(5''-caffeylarabinoside))

3D PDB for HMDB0301882 (Apigeninidin 5-(5''-caffeylarabinoside))

SMILES for HMDB0301882 (Apigeninidin 5-(5''-caffeylarabinoside))

INCHI for HMDB0301882 (Apigeninidin 5-(5''-caffeylarabinoside))

Structure for HMDB0301882 (Apigeninidin 5-(5''-caffeylarabinoside))

3D Structure for HMDB0301882 (Apigeninidin 5-(5''-caffeylarabinoside))

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

MS/MS Spectra