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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2021-09-23 03:19:41 UTC

Update Date

2021-09-23 03:19:41 UTC

HMDB ID

HMDB0301883

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Pelargonidin 3-p-coumarylglucoside

Description

Pelargonidin 3-p-coumarylglucoside is a member of the class of compounds known as anthocyanidin 3-o-6-p-coumaroyl glycosides. Anthocyanidin 3-o-6-p-coumaroyl glycosides are anthocyanidin 3-O-glycosides where the carbohydrate moiety is esterified at the C6 position with a p-coumaric acid. P-coumaric acid is an organic derivative of cinnamic acid, that carries a hydroxyl group at the 4-position of the benzene ring. Pelargonidin 3-p-coumarylglucoside is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Pelargonidin 3-p-coumarylglucoside can be found in common grape, which makes pelargonidin 3-p-coumarylglucoside a potential biomarker for the consumption of this food product.

Structure

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

  Mrv0541 02241223292D          

 42 46  0  0  0  0            999 V2000
   -1.0209   -0.7975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0209    0.0275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3093   -1.2100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7497   -1.2100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3093    0.4228    0.0000 O   0  3  0  0  0  0  0  0  0  0  0  0
   -1.7497    0.4228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3850   -0.7975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4646   -0.7975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7497   -2.0419    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3850    0.0275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4646    0.0275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0965    0.4228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1797    0.4228    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8219    0.0275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0965    1.2546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5334    0.4228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8219    1.6671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5334    1.2546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2519    1.6671    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1020   -1.2055    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3876   -2.4430    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3876   -3.2680    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1021   -3.6805    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8165   -3.2680    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8165   -2.4430    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1020   -2.0305    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5310   -2.0305    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5310   -3.6805    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1021   -4.5055    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3269   -3.6805    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3269   -4.5055    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2144   -5.2200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0394   -5.2200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4519   -5.9345    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0394   -6.6490    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2144   -6.6489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8019   -5.9345    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2769   -5.9345    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9769   -5.9345    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5644   -5.2200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7394   -5.2200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3269   -5.9345    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  2  0  0  0  0
  1  4  1  0  0  0  0
  2  5  2  0  0  0  0
  2  6  1  0  0  0  0
  3  7  1  0  0  0  0
  4  8  2  0  0  0  0
  4  9  1  0  0  0  0
  5 10  1  0  0  0  0
  6 11  2  0  0  0  0
 10 12  1  0  0  0  0
 11 13  1  0  0  0  0
 12 14  2  0  0  0  0
 12 15  1  0  0  0  0
 14 16  1  0  0  0  0
 15 17  2  0  0  0  0
 16 18  2  0  0  0  0
 18 19  1  0  0  0  0
  7 10  2  0  0  0  0
  8 11  1  0  0  0  0
 17 18  1  0  0  0  0
  7 20  1  0  0  0  0
 26 20  1  1  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 21 26  1  0  0  0  0
 25 27  1  6  0  0  0
 24 28  1  1  0  0  0
 23 29  1  6  0  0  0
 22 30  1  1  0  0  0
 30 31  1  0  0  0  0
 41 31  1  0  0  0  0
 32 33  2  0  0  0  0
 33 34  1  0  0  0  0
 34 35  2  0  0  0  0
 35 36  1  0  0  0  0
 36 37  2  0  0  0  0
 32 37  1  0  0  0  0
 34 38  1  0  0  0  0
 37 39  1  0  0  0  0
 39 40  2  0  0  0  0
 40 41  1  0  0  0  0
 41 42  2  0  0  0  0
M  CHG  1   5   1
M  END

HMDB0301883
     RDKit          3D
Pelargonidin 3-p-coumarylglucoside
 69 73  0  0  0  0  0  0  0  0999 V2000
    3.2202   -2.4597    0.2752 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8853   -1.4916    0.7081 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3328   -1.4287    0.4121 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0767   -0.4300    0.8455 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4978   -0.3024    0.5951 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2234   -1.2221   -0.1193 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5892   -1.0585   -0.3349 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2499    0.0311    0.1637 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6267    0.2281   -0.0348 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.5423    0.9720    0.8863 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1808    0.7865    1.0882 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2485   -0.5196    1.4443 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8889   -0.4772    1.7832 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0756   -0.4232    0.5099 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2794   -0.3747    0.7954 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0755   -0.5731   -0.3497 C   0  0  1  0  0  0  0  0  0  0  0  0
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   -3.4760    1.8150    0.4335 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6631    2.4564    0.6644 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.6072    4.5110    1.2777 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9846    4.3607    1.2950 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1537    3.6792    1.1139 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3994    4.2797    1.3356 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0774    2.3689    0.7029 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8366    1.7639    0.4804 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7677    0.5332    0.0943 O   0  0  0  0  0  3  0  0  0  0  0  0
   -4.6380   -0.1466   -0.1488 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8418   -1.5054   -0.5667 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0497   -2.1308   -0.2576 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3219   -3.4078   -0.6976 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4265   -4.1200   -1.4552 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6966   -5.4236   -1.9077 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2384   -3.5162   -1.7654 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9783   -2.2192   -1.3113 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3183   -0.1395   -1.5956 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2701   -1.2578   -2.1588 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5807    1.0235   -1.3901 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1682    2.1742   -1.1403 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5234    0.7856   -0.2522 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8310    0.6156   -0.7091 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7991   -2.2029   -0.1653 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5328    0.3308    1.4307 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7458   -2.1083   -0.5393 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.1290   -1.7922   -0.8963 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.1188   -0.4828   -0.5718 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.0847    1.8265    1.2713 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6265    1.5200    1.6516 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6025   -1.3406    2.4212 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7187    0.4223    2.3962 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2545   -1.3185   -0.0890 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1184   -1.7060   -0.4160 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5437    2.3417    0.5720 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6643    4.2224    1.1621 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0267    5.3856    1.6177 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2436    3.7585    1.1946 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0031    1.8320    0.5600 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7914   -1.5870    0.3504 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2764   -3.8376   -0.4232 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1525   -5.4910   -2.8088 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5113   -4.0600   -2.3649 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0570   -1.8021   -1.6307 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1130    0.1892   -2.3092 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1603   -2.1042   -1.8545 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1822    1.1524   -2.3407 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1205    1.9764   -1.3335 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5369    1.7073    0.3791 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0176    1.2416   -1.4523 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  2  0
  2 12  1  0
 12 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  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 21 23  1  0
 23 24  2  0
 24 25  1  0
 24 26  1  0
 26 27  2  0
 27 28  1  0
 28 29  2  0
 29 30  1  0
 30 31  2  0
 31 32  1  0
 32 33  2  0
 33 34  1  0
 33 35  1  0
 35 36  2  0
 16 37  1  0
 37 38  1  0
 37 39  1  0
 39 40  1  0
 39 41  1  0
 41 42  1  0
 11  5  1  0
 41 14  1  0
 29 18  1  0
 36 30  1  0
 27 20  1  0
  3 43  1  0
  4 44  1  0
  6 45  1  0
  7 46  1  0
  9 47  1  0
 10 48  1  0
 11 49  1  0
 13 50  1  0
 13 51  1  0
 14 52  1  6
 16 53  1  6
 19 54  1  0
 22 55  1  0
 23 56  1  0
 25 57  1  0
 26 58  1  0
 31 59  1  0
 32 60  1  0
 34 61  1  0
 35 62  1  0
 36 63  1  0
 37 64  1  6
 38 65  1  0
 39 66  1  6
 40 67  1  0
 41 68  1  1
 42 69  1  0
M  CHG  1  28   1
M  END

  Mrv0541 02241223292D          

 42 46  0  0  0  0            999 V2000
   -1.0209   -0.7975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0209    0.0275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3093   -1.2100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7497   -1.2100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3093    0.4228    0.0000 O   0  3  0  0  0  0  0  0  0  0  0  0
   -1.7497    0.4228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3850   -0.7975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4646   -0.7975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7497   -2.0419    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3850    0.0275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.0965    0.4228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.0965    1.2546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5334    0.4228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8219    1.6671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.1021   -3.6805    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
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    1.8165   -2.4430    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1020   -2.0305    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5310   -2.0305    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5310   -3.6805    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1021   -4.5055    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3269   -3.6805    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.0394   -5.2200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4519   -5.9345    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.2144   -6.6489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8019   -5.9345    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2769   -5.9345    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9769   -5.9345    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5644   -5.2200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7394   -5.2200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3269   -5.9345    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  2  0  0  0  0
  1  4  1  0  0  0  0
  2  5  2  0  0  0  0
  2  6  1  0  0  0  0
  3  7  1  0  0  0  0
  4  8  2  0  0  0  0
  4  9  1  0  0  0  0
  5 10  1  0  0  0  0
  6 11  2  0  0  0  0
 10 12  1  0  0  0  0
 11 13  1  0  0  0  0
 12 14  2  0  0  0  0
 12 15  1  0  0  0  0
 14 16  1  0  0  0  0
 15 17  2  0  0  0  0
 16 18  2  0  0  0  0
 18 19  1  0  0  0  0
  7 10  2  0  0  0  0
  8 11  1  0  0  0  0
 17 18  1  0  0  0  0
  7 20  1  0  0  0  0
 26 20  1  1  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 21 26  1  0  0  0  0
 25 27  1  6  0  0  0
 24 28  1  1  0  0  0
 23 29  1  6  0  0  0
 22 30  1  1  0  0  0
 30 31  1  0  0  0  0
 41 31  1  0  0  0  0
 32 33  2  0  0  0  0
 33 34  1  0  0  0  0
 34 35  2  0  0  0  0
 35 36  1  0  0  0  0
 36 37  2  0  0  0  0
 32 37  1  0  0  0  0
 34 38  1  0  0  0  0
 37 39  1  0  0  0  0
 39 40  2  0  0  0  0
 40 41  1  0  0  0  0
 41 42  2  0  0  0  0
M  CHG  1   5   1
M  END
> <DATABASE_ID>
HMDB0301883

> <DATABASE_NAME>
hmdb

> <SMILES>
O[C@@H]1[C@@H](COC(=O)\C=C\C2=CC=C(O)C=C2)O[C@@H](OC2=C([O+]=C3C=C(O)C=C(O)C3=C2)C2=CC=C(O)C=C2)[C@H](O)[C@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C30H26O12/c31-17-6-1-15(2-7-17)3-10-25(35)39-14-24-26(36)27(37)28(38)30(42-24)41-23-13-20-21(34)11-19(33)12-22(20)40-29(23)16-4-8-18(32)9-5-16/h1-13,24,26-28,30,36-38H,14H2,(H3-,31,32,33,34,35)/p+1/t24-,26-,27+,28-,30-/m1/s1

> <INCHI_KEY>
VZPBBOAZFCREMQ-SHPGVJHPSA-O

> <FORMULA>
C30H27O12

> <MOLECULAR_WEIGHT>
579.5282

> <EXACT_MASS>
579.150251328

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_AVERAGE_POLARIZABILITY>
58.434026676022974

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
1

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
5,7-dihydroxy-2-(4-hydroxyphenyl)-3-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-({[(2E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}methyl)oxan-2-yl]oxy}-1λ⁴-chromen-1-ylium

> <ALOGPS_LOGP>
2.80

> <JCHEM_LOGP>
4.0851

> <ALOGPS_LOGS>
-4.34

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
7.53036967202837

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.396386122917065

> <JCHEM_PKA_STRONGEST_BASIC>
-3.64911035489539

> <JCHEM_POLAR_SURFACE_AREA>
199.51

> <JCHEM_REFRACTIVITY>
155.82520000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.83e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5,7-dihydroxy-2-(4-hydroxyphenyl)-3-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-({[(2E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}methyl)oxan-2-yl]oxy}-1λ⁴-chromen-1-ylium

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0301883
     RDKit          3D
Pelargonidin 3-p-coumarylglucoside
 69 73  0  0  0  0  0  0  0  0999 V2000
    3.2202   -2.4597    0.2752 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8853   -1.4916    0.7081 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3328   -1.4287    0.4121 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0767   -0.4300    0.8455 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4978   -0.3024    0.5951 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2234   -1.2221   -0.1193 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5892   -1.0585   -0.3349 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2499    0.0311    0.1637 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6267    0.2281   -0.0348 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.5423    0.9720    0.8863 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1808    0.7865    1.0882 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2485   -0.5196    1.4443 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8889   -0.4772    1.7832 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0756   -0.4232    0.5099 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2794   -0.3747    0.7954 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0755   -0.5731   -0.3497 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.2585   -0.0538   -0.1685 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4206    0.4486    0.0075 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4760    1.8150    0.4335 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6631    2.4564    0.6644 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7329    3.7745    1.0781 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6072    4.5110    1.2777 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9846    4.3607    1.2950 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1537    3.6792    1.1139 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3994    4.2797    1.3356 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0774    2.3689    0.7029 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8366    1.7639    0.4804 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7677    0.5332    0.0943 O   0  0  0  0  0  3  0  0  0  0  0  0
   -4.6380   -0.1466   -0.1488 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8418   -1.5054   -0.5667 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0497   -2.1308   -0.2576 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3219   -3.4078   -0.6976 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4265   -4.1200   -1.4552 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6966   -5.4236   -1.9077 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2384   -3.5162   -1.7654 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9783   -2.2192   -1.3113 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3183   -0.1395   -1.5956 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2701   -1.2578   -2.1588 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5807    1.0235   -1.3901 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1682    2.1742   -1.1403 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5234    0.7856   -0.2522 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8310    0.6156   -0.7091 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7991   -2.2029   -0.1653 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5328    0.3308    1.4307 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7458   -2.1083   -0.5393 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.1290   -1.7922   -0.8963 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.1188   -0.4828   -0.5718 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.0847    1.8265    1.2713 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6265    1.5200    1.6516 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6025   -1.3406    2.4212 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7187    0.4223    2.3962 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2545   -1.3185   -0.0890 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1184   -1.7060   -0.4160 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5437    2.3417    0.5720 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6643    4.2224    1.1621 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0267    5.3856    1.6177 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2436    3.7585    1.1946 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0031    1.8320    0.5600 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7914   -1.5870    0.3504 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2764   -3.8376   -0.4232 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1525   -5.4910   -2.8088 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5113   -4.0600   -2.3649 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0570   -1.8021   -1.6307 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1130    0.1892   -2.3092 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1603   -2.1042   -1.8545 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1822    1.1524   -2.3407 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1205    1.9764   -1.3335 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5369    1.7073    0.3791 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0176    1.2416   -1.4523 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  2  0
  2 12  1  0
 12 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  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 21 23  1  0
 23 24  2  0
 24 25  1  0
 24 26  1  0
 26 27  2  0
 27 28  1  0
 28 29  2  0
 29 30  1  0
 30 31  2  0
 31 32  1  0
 32 33  2  0
 33 34  1  0
 33 35  1  0
 35 36  2  0
 16 37  1  0
 37 38  1  0
 37 39  1  0
 39 40  1  0
 39 41  1  0
 41 42  1  0
 11  5  1  0
 41 14  1  0
 29 18  1  0
 36 30  1  0
 27 20  1  0
  3 43  1  0
  4 44  1  0
  6 45  1  0
  7 46  1  0
  9 47  1  0
 10 48  1  0
 11 49  1  0
 13 50  1  0
 13 51  1  0
 14 52  1  6
 16 53  1  6
 19 54  1  0
 22 55  1  0
 23 56  1  0
 25 57  1  0
 26 58  1  0
 31 59  1  0
 32 60  1  0
 34 61  1  0
 35 62  1  0
 36 63  1  0
 37 64  1  6
 38 65  1  0
 39 66  1  6
 40 67  1  0
 41 68  1  1
 42 69  1  0
M  CHG  1  28   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      -1.906  -1.489   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.906   0.051   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.577  -2.259   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -3.266  -2.259   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      -0.577   0.789   0.000  0.00  0.00           O+1
HETATM    6  C   UNK     0      -3.266   0.789   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.719  -1.489   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -4.601  -1.489   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -3.266  -3.812   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       0.719   0.051   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -4.601   0.051   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.047   0.789   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -5.935   0.789   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       3.401   0.051   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.047   2.342   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.729   0.789   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.401   3.112   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.729   2.342   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       6.070   3.112   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       2.057  -2.250   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       0.724  -4.560   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       0.724  -6.100   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       2.057  -6.870   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       3.391  -6.100   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       3.391  -4.560   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       2.057  -3.790   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       4.725  -3.790   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0       4.725  -6.870   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0       2.057  -8.410   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      -0.610  -6.870   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      -0.610  -8.410   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      -6.000  -9.744   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -7.540  -9.744   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      -8.310 -11.078   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      -7.540 -12.411   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      -6.000 -12.411   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      -5.230 -11.078   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0      -9.850 -11.078   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0      -3.690 -11.078   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      -2.920  -9.744   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      -1.380  -9.744   0.000  0.00  0.00           C+0
HETATM   42  O   UNK     0      -0.610 -11.078   0.000  0.00  0.00           O+0
CONECT    1    2    3    4                                                  
CONECT    2    1    5    6                                                  
CONECT    3    1    7                                                       
CONECT    4    1    8    9                                                  
CONECT    5    2   10                                                       
CONECT    6    2   11                                                       
CONECT    7    3   10   20                                                  
CONECT    8    4   11                                                       
CONECT    9    4                                                            
CONECT   10    5   12    7                                                  
CONECT   11    6   13    8                                                  
CONECT   12   10   14   15                                                  
CONECT   13   11                                                            
CONECT   14   12   16                                                       
CONECT   15   12   17                                                       
CONECT   16   14   18                                                       
CONECT   17   15   18                                                       
CONECT   18   16   19   17                                                  
CONECT   19   18                                                            
CONECT   20    7   26                                                       
CONECT   21   22   26                                                       
CONECT   22   21   23   30                                                  
CONECT   23   22   24   29                                                  
CONECT   24   23   25   28                                                  
CONECT   25   24   26   27                                                  
CONECT   26   20   25   21                                                  
CONECT   27   25                                                            
CONECT   28   24                                                            
CONECT   29   23                                                            
CONECT   30   22   31                                                       
CONECT   31   30   41                                                       
CONECT   32   33   37                                                       
CONECT   33   32   34                                                       
CONECT   34   33   35   38                                                  
CONECT   35   34   36                                                       
CONECT   36   35   37                                                       
CONECT   37   36   32   39                                                  
CONECT   38   34                                                            
CONECT   39   37   40                                                       
CONECT   40   39   41                                                       
CONECT   41   31   40   42                                                  
CONECT   42   41                                                            
MASTER        0    0    0    0    0    0    0    0   42    0   92    0
END

COMPND    HMDB0301883
HETATM    1  O1  UNL     1       3.220  -2.460   0.275  1.00  0.00           O  
HETATM    2  C1  UNL     1       3.885  -1.492   0.708  1.00  0.00           C  
HETATM    3  C2  UNL     1       5.333  -1.429   0.412  1.00  0.00           C  
HETATM    4  C3  UNL     1       6.077  -0.430   0.846  1.00  0.00           C  
HETATM    5  C4  UNL     1       7.498  -0.302   0.595  1.00  0.00           C  
HETATM    6  C5  UNL     1       8.223  -1.222  -0.119  1.00  0.00           C  
HETATM    7  C6  UNL     1       9.589  -1.058  -0.335  1.00  0.00           C  
HETATM    8  C7  UNL     1      10.250   0.031   0.164  1.00  0.00           C  
HETATM    9  O2  UNL     1      11.627   0.228  -0.035  1.00  0.00           O  
HETATM   10  C8  UNL     1       9.542   0.972   0.886  1.00  0.00           C  
HETATM   11  C9  UNL     1       8.181   0.786   1.088  1.00  0.00           C  
HETATM   12  O3  UNL     1       3.249  -0.520   1.444  1.00  0.00           O  
HETATM   13  C10 UNL     1       1.889  -0.477   1.783  1.00  0.00           C  
HETATM   14  C11 UNL     1       1.076  -0.423   0.510  1.00  0.00           C  
HETATM   15  O4  UNL     1      -0.279  -0.375   0.795  1.00  0.00           O  
HETATM   16  C12 UNL     1      -1.075  -0.573  -0.350  1.00  0.00           C  
HETATM   17  O5  UNL     1      -2.258  -0.054  -0.168  1.00  0.00           O  
HETATM   18  C13 UNL     1      -3.421   0.449   0.007  1.00  0.00           C  
HETATM   19  C14 UNL     1      -3.476   1.815   0.433  1.00  0.00           C  
HETATM   20  C15 UNL     1      -4.663   2.456   0.664  1.00  0.00           C  
HETATM   21  C16 UNL     1      -4.733   3.775   1.078  1.00  0.00           C  
HETATM   22  O6  UNL     1      -3.607   4.511   1.278  1.00  0.00           O  
HETATM   23  C17 UNL     1      -5.985   4.361   1.295  1.00  0.00           C  
HETATM   24  C18 UNL     1      -7.154   3.679   1.114  1.00  0.00           C  
HETATM   25  O7  UNL     1      -8.399   4.280   1.336  1.00  0.00           O  
HETATM   26  C19 UNL     1      -7.077   2.369   0.703  1.00  0.00           C  
HETATM   27  C20 UNL     1      -5.837   1.764   0.480  1.00  0.00           C  
HETATM   28  O8  UNL     1      -5.768   0.533   0.094  1.00  0.00           O1+
HETATM   29  C21 UNL     1      -4.638  -0.147  -0.149  1.00  0.00           C  
HETATM   30  C22 UNL     1      -4.842  -1.505  -0.567  1.00  0.00           C  
HETATM   31  C23 UNL     1      -6.050  -2.131  -0.258  1.00  0.00           C  
HETATM   32  C24 UNL     1      -6.322  -3.408  -0.698  1.00  0.00           C  
HETATM   33  C25 UNL     1      -5.427  -4.120  -1.455  1.00  0.00           C  
HETATM   34  O9  UNL     1      -5.697  -5.424  -1.908  1.00  0.00           O  
HETATM   35  C26 UNL     1      -4.238  -3.516  -1.765  1.00  0.00           C  
HETATM   36  C27 UNL     1      -3.978  -2.219  -1.311  1.00  0.00           C  
HETATM   37  C28 UNL     1      -0.318  -0.139  -1.596  1.00  0.00           C  
HETATM   38  O10 UNL     1       0.270  -1.258  -2.159  1.00  0.00           O  
HETATM   39  C29 UNL     1       0.581   1.024  -1.390  1.00  0.00           C  
HETATM   40  O11 UNL     1      -0.168   2.174  -1.140  1.00  0.00           O  
HETATM   41  C30 UNL     1       1.523   0.786  -0.252  1.00  0.00           C  
HETATM   42  O12 UNL     1       2.831   0.616  -0.709  1.00  0.00           O  
HETATM   43  H1  UNL     1       5.799  -2.203  -0.165  1.00  0.00           H  
HETATM   44  H2  UNL     1       5.533   0.331   1.431  1.00  0.00           H  
HETATM   45  H3  UNL     1       7.746  -2.108  -0.539  1.00  0.00           H  
HETATM   46  H4  UNL     1      10.129  -1.792  -0.896  1.00  0.00           H  
HETATM   47  H5  UNL     1      12.119  -0.483  -0.572  1.00  0.00           H  
HETATM   48  H6  UNL     1      10.085   1.827   1.271  1.00  0.00           H  
HETATM   49  H7  UNL     1       7.626   1.520   1.652  1.00  0.00           H  
HETATM   50  H8  UNL     1       1.603  -1.341   2.421  1.00  0.00           H  
HETATM   51  H9  UNL     1       1.719   0.422   2.396  1.00  0.00           H  
HETATM   52  H10 UNL     1       1.255  -1.318  -0.089  1.00  0.00           H  
HETATM   53  H11 UNL     1      -1.118  -1.706  -0.416  1.00  0.00           H  
HETATM   54  H12 UNL     1      -2.544   2.342   0.572  1.00  0.00           H  
HETATM   55  H13 UNL     1      -2.664   4.222   1.162  1.00  0.00           H  
HETATM   56  H14 UNL     1      -6.027   5.386   1.618  1.00  0.00           H  
HETATM   57  H15 UNL     1      -9.244   3.758   1.195  1.00  0.00           H  
HETATM   58  H16 UNL     1      -8.003   1.832   0.560  1.00  0.00           H  
HETATM   59  H17 UNL     1      -6.791  -1.587   0.350  1.00  0.00           H  
HETATM   60  H18 UNL     1      -7.276  -3.838  -0.423  1.00  0.00           H  
HETATM   61  H19 UNL     1      -6.152  -5.491  -2.809  1.00  0.00           H  
HETATM   62  H20 UNL     1      -3.511  -4.060  -2.365  1.00  0.00           H  
HETATM   63  H21 UNL     1      -3.057  -1.802  -1.631  1.00  0.00           H  
HETATM   64  H22 UNL     1      -1.113   0.189  -2.309  1.00  0.00           H  
HETATM   65  H23 UNL     1      -0.160  -2.104  -1.854  1.00  0.00           H  
HETATM   66  H24 UNL     1       1.182   1.152  -2.341  1.00  0.00           H  
HETATM   67  H25 UNL     1      -1.121   1.976  -1.333  1.00  0.00           H  
HETATM   68  H26 UNL     1       1.537   1.707   0.379  1.00  0.00           H  
HETATM   69  H27 UNL     1       3.018   1.242  -1.452  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3   12
CONECT    3    4    4   43
CONECT    4    5   44
CONECT    5    6    6   11
CONECT    6    7   45
CONECT    7    8    8   46
CONECT    8    9   10
CONECT    9   47
CONECT   10   11   11   48
CONECT   11   49
CONECT   12   13
CONECT   13   14   50   51
CONECT   14   15   41   52
CONECT   15   16
CONECT   16   17   37   53
CONECT   17   18
CONECT   18   19   19   29
CONECT   19   20   54
CONECT   20   21   21   27
CONECT   21   22   23
CONECT   22   55
CONECT   23   24   24   56
CONECT   24   25   26
CONECT   25   57
CONECT   26   27   27   58
CONECT   27   28
CONECT   28   29   29
CONECT   29   30
CONECT   30   31   31   36
CONECT   31   32   59
CONECT   32   33   33   60
CONECT   33   34   35
CONECT   34   61
CONECT   35   36   36   62
CONECT   36   63
CONECT   37   38   39   64
CONECT   38   65
CONECT   39   40   41   66
CONECT   40   67
CONECT   41   42   68
CONECT   42   69
END

HMDB0301883
     RDKit          3D
Pelargonidin 3-p-coumarylglucoside
 69 73  0  0  0  0  0  0  0  0999 V2000
    3.2202   -2.4597    0.2752 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8853   -1.4916    0.7081 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3328   -1.4287    0.4121 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0767   -0.4300    0.8455 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4978   -0.3024    0.5951 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2234   -1.2221   -0.1193 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5892   -1.0585   -0.3349 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2499    0.0311    0.1637 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6267    0.2281   -0.0348 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.5423    0.9720    0.8863 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1808    0.7865    1.0882 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2485   -0.5196    1.4443 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8889   -0.4772    1.7832 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0756   -0.4232    0.5099 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2794   -0.3747    0.7954 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0755   -0.5731   -0.3497 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.2585   -0.0538   -0.1685 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4206    0.4486    0.0075 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4760    1.8150    0.4335 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6631    2.4564    0.6644 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7329    3.7745    1.0781 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6072    4.5110    1.2777 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9846    4.3607    1.2950 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1537    3.6792    1.1139 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3994    4.2797    1.3356 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0774    2.3689    0.7029 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8366    1.7639    0.4804 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7677    0.5332    0.0943 O   0  0  0  0  0  3  0  0  0  0  0  0
   -4.6380   -0.1466   -0.1488 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8418   -1.5054   -0.5667 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0497   -2.1308   -0.2576 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3219   -3.4078   -0.6976 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4265   -4.1200   -1.4552 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6966   -5.4236   -1.9077 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2384   -3.5162   -1.7654 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9783   -2.2192   -1.3113 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3183   -0.1395   -1.5956 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2701   -1.2578   -2.1588 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5807    1.0235   -1.3901 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1682    2.1742   -1.1403 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5234    0.7856   -0.2522 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8310    0.6156   -0.7091 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7991   -2.2029   -0.1653 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5328    0.3308    1.4307 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7458   -2.1083   -0.5393 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.1290   -1.7922   -0.8963 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.1188   -0.4828   -0.5718 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.0847    1.8265    1.2713 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6265    1.5200    1.6516 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6025   -1.3406    2.4212 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7187    0.4223    2.3962 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2545   -1.3185   -0.0890 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1184   -1.7060   -0.4160 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5437    2.3417    0.5720 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6643    4.2224    1.1621 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0267    5.3856    1.6177 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2436    3.7585    1.1946 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0031    1.8320    0.5600 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7914   -1.5870    0.3504 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2764   -3.8376   -0.4232 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1525   -5.4910   -2.8088 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5113   -4.0600   -2.3649 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0570   -1.8021   -1.6307 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1130    0.1892   -2.3092 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1603   -2.1042   -1.8545 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1822    1.1524   -2.3407 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1205    1.9764   -1.3335 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5369    1.7073    0.3791 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0176    1.2416   -1.4523 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  2  0
  2 12  1  0
 12 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  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 21 23  1  0
 23 24  2  0
 24 25  1  0
 24 26  1  0
 26 27  2  0
 27 28  1  0
 28 29  2  0
 29 30  1  0
 30 31  2  0
 31 32  1  0
 32 33  2  0
 33 34  1  0
 33 35  1  0
 35 36  2  0
 16 37  1  0
 37 38  1  0
 37 39  1  0
 39 40  1  0
 39 41  1  0
 41 42  1  0
 11  5  1  0
 41 14  1  0
 29 18  1  0
 36 30  1  0
 27 20  1  0
  3 43  1  0
  4 44  1  0
  6 45  1  0
  7 46  1  0
  9 47  1  0
 10 48  1  0
 11 49  1  0
 13 50  1  0
 13 51  1  0
 14 52  1  6
 16 53  1  6
 19 54  1  0
 22 55  1  0
 23 56  1  0
 25 57  1  0
 26 58  1  0
 31 59  1  0
 32 60  1  0
 34 61  1  0
 35 62  1  0
 36 63  1  0
 37 64  1  6
 38 65  1  0
 39 66  1  6
 40 67  1  0
 41 68  1  1
 42 69  1  0
M  CHG  1  28   1
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₃₀H₂₇O₁₂

Average Molecular Weight

579.5282

Monoisotopic Molecular Weight

579.150251328

IUPAC Name

5,7-dihydroxy-2-(4-hydroxyphenyl)-3-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-({[(2E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}methyl)oxan-2-yl]oxy}-1λ⁴-chromen-1-ylium

Traditional Name

5,7-dihydroxy-2-(4-hydroxyphenyl)-3-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-({[(2E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}methyl)oxan-2-yl]oxy}-1λ⁴-chromen-1-ylium

CAS Registry Number

Not Available

SMILES

O[C@@H]1[C@@H](COC(=O)\C=C\C2=CC=C(O)C=C2)O[C@@H](OC2=C([O+]=C3C=C(O)C=C(O)C3=C2)C2=CC=C(O)C=C2)[C@H](O)[C@H]1O

InChI Identifier

InChI=1S/C30H26O12/c31-17-6-1-15(2-7-17)3-10-25(35)39-14-24-26(36)27(37)28(38)30(42-24)41-23-13-20-21(34)11-19(33)12-22(20)40-29(23)16-4-8-18(32)9-5-16/h1-13,24,26-28,30,36-38H,14H2,(H3-,31,32,33,34,35)/p+1/t24-,26-,27+,28-,30-/m1/s1

InChI Key

VZPBBOAZFCREMQ-SHPGVJHPSA-O

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as anthocyanidin 3-o-6-p-coumaroyl glycosides. These are anthocyanidin 3-O-glycosides where the carbohydrate moiety is esterified at the C6 position with a p-coumaric acid. P-coumaric acid is an organic derivative of cinnamic acid, that carries a hydroxyl group at the 4-position of the benzene ring.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavonoid glycosides

Direct Parent

Anthocyanidin 3-O-6-p-coumaroyl glycosides

Alternative Parents

Substituents

Anthocyanidin 3-o-6-p-coumaroyl-glycoside
Anthocyanidin-3-o-glycoside
Anthocyanin
Flavonoid-3-o-glycoside
Hydroxyflavonoid
4'-hydroxyflavonoid
5-hydroxyflavonoid
7-hydroxyflavonoid
Anthocyanidin
Coumaric acid ester
Cinnamic acid or derivatives
Coumaric acid or derivatives
Cinnamic acid ester
Hydroxycinnamic acid or derivatives
O-glycosyl compound
Glycosyl compound
1-benzopyran
Benzopyran
Styrene
1-hydroxy-2-unsubstituted benzenoid
Fatty acid ester
Phenol
1-hydroxy-4-unsubstituted benzenoid
Fatty acyl
Monocyclic benzene moiety
Benzenoid
Oxane
Monosaccharide
Heteroaromatic compound
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Secondary alcohol
Carboxylic acid ester
Monocarboxylic acid or derivatives
Acetal
Polyol
Oxacycle
Organoheterocyclic compound
Carboxylic acid derivative
Organic oxygen compound
Alcohol
Organooxygen compound
Organic oxide
Hydrocarbon derivative
Carbonyl group
Organic cation
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

monosaccharide derivative (CHEBI:80475 )
anthocyanidin glycoside (CHEBI:80475 )
cinnamate ester (CHEBI:80475 )
Anthocyanidins (C16368 )
Anthocyanidins and anthocyanins (C16368 )

Ontology

Not Available

Exogenous (HMDB: HMDB0301883)

Food

Fruit

Berry

Common grape (FooDB: FOOD00204)

Process

Not Available

Role

Not Available

Physical Properties

State

Liquid

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	2.8	ALOGPS
logP	4.09	ChemAxon
logS	-4.3	ALOGPS
pKa (Strongest Acidic)	6.4	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	199.51 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	155.83 m³·mol⁻¹	ChemAxon
Polarizability	58.43 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]+	232.449	32859911
AllCCS	[M+H-H2O]+	231.029	32859911
AllCCS	[M+Na]+	234.093	32859911
AllCCS	[M+NH4]+	233.731	32859911
AllCCS	[M-H]-	224.002	32859911
AllCCS	[M+Na-2H]-	225.496	32859911
AllCCS	[M+HCOO]-	227.289	32859911
DeepCCS	[M+H]+	224.1	30932474
DeepCCS	[M-H]-	222.002	30932474
DeepCCS	[M-2H]-	255.473	30932474
DeepCCS	[M+Na]+	229.841	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 - Pelargonidin 3-p-coumarylglucoside 10V, Positive-QTOF	splash10-001i-0100090000-3c842f1d3d8e87100b9f	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pelargonidin 3-p-coumarylglucoside 20V, Positive-QTOF	splash10-000i-0000090000-b602d3bccb1fc4036340	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pelargonidin 3-p-coumarylglucoside 40V, Positive-QTOF	splash10-01t9-0900000000-1c7470c5306d42be291f	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pelargonidin 3-p-coumarylglucoside 10V, Negative-QTOF	splash10-004i-0000090000-5edc59562ba1e58d8f45	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pelargonidin 3-p-coumarylglucoside 20V, Negative-QTOF	splash10-004i-1100090000-a911e2e9152bcb7ffb50	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pelargonidin 3-p-coumarylglucoside 40V, Negative-QTOF	splash10-0bvl-8910000000-5a578b0b83ec90798441	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

FDB001570

KNApSAcK ID

Not Available

Chemspider ID

34999387

KEGG Compound ID

C16368

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

80475

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 Pelargonidin 3-p-coumarylglucoside (HMDB0301883)

MOL for HMDB0301883 (Pelargonidin 3-p-coumarylglucoside)

3D MOL for HMDB0301883 (Pelargonidin 3-p-coumarylglucoside)

3D SDF for HMDB0301883 (Pelargonidin 3-p-coumarylglucoside)

3D-SDF for HMDB0301883 (Pelargonidin 3-p-coumarylglucoside)

PDB for HMDB0301883 (Pelargonidin 3-p-coumarylglucoside)

3D PDB for HMDB0301883 (Pelargonidin 3-p-coumarylglucoside)

SMILES for HMDB0301883 (Pelargonidin 3-p-coumarylglucoside)

INCHI for HMDB0301883 (Pelargonidin 3-p-coumarylglucoside)

Structure for HMDB0301883 (Pelargonidin 3-p-coumarylglucoside)

3D Structure for HMDB0301883 (Pelargonidin 3-p-coumarylglucoside)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

MS/MS Spectra