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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2021-09-23 03:20:47 UTC

Update Date

2021-09-23 03:20:47 UTC

HMDB ID

HMDB0301885

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Cyanidin 3-(3''-malonylglucoside)

Description

Cyanidin 3-(3''-malonylglucoside) is a member of the class of compounds known as anthocyanidin-3-o-glycosides. Anthocyanidin-3-o-glycosides are phenolic compounds containing one anthocyanidin moiety which is O-glycosidically linked to a carbohydrate moiety at the C3-position. Cyanidin 3-(3''-malonylglucoside) is practically insoluble (in water) and a weakly acidic compound (based on its pKa). Cyanidin 3-(3''-malonylglucoside) can be found in garlic, which makes cyanidin 3-(3''-malonylglucoside) a potential biomarker for the consumption of this food product.

Structure

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


  Mrv0541 02241221012D          

 38 41  0  0  0  0            999 V2000
    0.2303    0.0275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9453    0.4228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4640    0.4228    0.0000 O   0  3  0  0  0  0  0  0  0  0  0  0
    0.2303   -0.7975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6671    0.0275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9453    1.2546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1756    0.0275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4640   -1.2134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9453   -1.2134    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3787    0.4228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6671    1.6671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1756   -0.7975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9043    0.4228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3787    1.2546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0869    0.0034    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9043   -1.2134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6193    0.0275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0971    1.6671    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6193   -0.7975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9043   -2.0419    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3343    0.4228    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2308   -2.4509    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2308   -3.2759    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9453   -3.6884    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6598   -3.2759    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6598   -2.4509    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9453   -2.0384    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3743   -2.0384    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3743   -3.6884    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9453   -4.5134    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4836   -3.6884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4836   -4.5134    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2322   -3.6884    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0888   -3.2759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8032   -3.6884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5177   -3.2759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0888   -2.4509    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5177   -2.4509    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  1  0  0  0  0
  1  4  2  0  0  0  0
  2  5  2  0  0  0  0
  2  6  1  0  0  0  0
  3  7  2  0  0  0  0
  4  8  1  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
  7 12  1  0  0  0  0
  7 13  1  0  0  0  0
 10 14  2  0  0  0  0
 10 15  1  0  0  0  0
 12 16  1  0  0  0  0
 13 17  2  0  0  0  0
 14 18  1  0  0  0  0
 16 19  2  0  0  0  0
 16 20  1  0  0  0  0
 17 21  1  0  0  0  0
  8 12  2  0  0  0  0
 11 14  1  0  0  0  0
 17 19  1  0  0  0  0
 27  9  1  1  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
 26 27  1  0  0  0  0
 22 27  1  0  0  0  0
 26 28  1  6  0  0  0
 25 29  1  1  0  0  0
 24 30  1  6  0  0  0
 23 31  1  1  0  0  0
 31 32  1  0  0  0  0
 29 34  1  0  0  0  0
 36 33  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 34 37  2  0  0  0  0
 36 38  2  0  0  0  0
M  CHG  1   3   1
M  END

HMDB0301885
     RDKit          3D
Cyanidin 3-(3''-malonylglucoside)
 61 64  0  0  0  0  0  0  0  0999 V2000
   -8.5037   -2.1697   -0.3205 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3463   -1.8152   -0.7040 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0030   -2.1009   -2.0130 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4962   -1.1434    0.2903 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2081   -0.6125   -0.3080 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9558   -0.7430   -1.5254 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2931    0.0333    0.4933 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0566    0.5929    0.0623 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8940   -0.1397    0.7119 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.8723   -1.5004    0.3755 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6352    0.5609    0.3406 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5496   -0.1212    0.5380 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7316   -0.0154   -0.1354 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7986    0.9844   -1.1083 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9677    1.1396   -1.8241 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0962    2.1250   -2.8105 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0724    2.9919   -3.1266 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3167    2.2033   -3.4782 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3510    1.3439   -3.1739 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5359    1.4753   -3.8722 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1933    0.3940   -2.2057 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9868    0.2651   -1.4980 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8896   -0.6584   -0.5814 O   0  0  0  0  0  3  0  0  0  0  0  0
    2.7775   -0.8420    0.1316 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7889   -1.9217    1.1361 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6862   -2.2523    1.8541 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7111   -3.2739    2.8159 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8761   -3.9674    3.0482 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9006   -4.9781    3.9996 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9912   -3.6137    2.3039 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1784   -4.3065    2.5315 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9655   -2.6232    1.3733 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6655    1.8097    1.0036 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5973    2.5602    0.2456 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4356    4.0185    0.6002 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6690    4.2391    1.9521 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9808    2.0450    0.4608 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.8697    2.8289   -0.2735 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6307   -3.0426   -2.2194 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2023   -1.8835    1.0897 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9832   -0.2873    0.7984 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8980    0.4804   -1.0296 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0770   -0.0232    1.8180 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0586   -2.0141    1.2415 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6883    0.8610   -0.7454 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9989    1.6373   -1.3210 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1943    2.9708   -2.6797 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4293    2.9645   -4.2470 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2558    2.1088   -3.4902 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0029   -0.3056   -1.9342 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7210   -1.7922    1.7586 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8125   -3.5362    3.3918 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1128   -5.2500    4.5433 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0215   -4.0851    2.0172 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8333   -2.3352    0.7843 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3599    2.4390   -0.8319 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0695    4.6722   -0.0302 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3740    4.3329    0.4011 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9602    4.7876    2.3355 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2741    2.1373    1.5353 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6894    2.3512   -0.4960 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  9 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 16 18  1  0
 18 19  2  0
 19 20  1  0
 19 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 28 29  1  0
 28 30  1  0
 30 31  1  0
 30 32  2  0
 11 33  1  0
 33 34  1  0
 34 35  1  0
 35 36  1  0
 34 37  1  0
 37 38  1  0
 37  8  1  0
 24 13  1  0
 32 25  1  0
 22 15  1  0
  3 39  1  0
  4 40  1  0
  4 41  1  0
  8 42  1  6
  9 43  1  1
 10 44  1  0
 11 45  1  6
 14 46  1  0
 17 47  1  0
 18 48  1  0
 20 49  1  0
 21 50  1  0
 26 51  1  0
 27 52  1  0
 29 53  1  0
 31 54  1  0
 32 55  1  0
 34 56  1  6
 35 57  1  0
 35 58  1  0
 36 59  1  0
 37 60  1  1
 38 61  1  0
M  CHG  1  23   1
M  END


  Mrv0541 02241221012D          

 38 41  0  0  0  0            999 V2000
    0.2303    0.0275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9453    0.4228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4640    0.4228    0.0000 O   0  3  0  0  0  0  0  0  0  0  0  0
    0.2303   -0.7975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6671    0.0275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9453    1.2546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1756    0.0275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4640   -1.2134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9453   -1.2134    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3787    0.4228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6671    1.6671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1756   -0.7975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9043    0.4228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3787    1.2546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0869    0.0034    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9043   -1.2134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6193    0.0275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0971    1.6671    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6193   -0.7975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9043   -2.0419    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3343    0.4228    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2308   -2.4509    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2308   -3.2759    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9453   -3.6884    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6598   -3.2759    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6598   -2.4509    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9453   -2.0384    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3743   -2.0384    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3743   -3.6884    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9453   -4.5134    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4836   -3.6884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4836   -4.5134    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2322   -3.6884    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0888   -3.2759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8032   -3.6884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5177   -3.2759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0888   -2.4509    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5177   -2.4509    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  1  0  0  0  0
  1  4  2  0  0  0  0
  2  5  2  0  0  0  0
  2  6  1  0  0  0  0
  3  7  2  0  0  0  0
  4  8  1  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
  7 12  1  0  0  0  0
  7 13  1  0  0  0  0
 10 14  2  0  0  0  0
 10 15  1  0  0  0  0
 12 16  1  0  0  0  0
 13 17  2  0  0  0  0
 14 18  1  0  0  0  0
 16 19  2  0  0  0  0
 16 20  1  0  0  0  0
 17 21  1  0  0  0  0
  8 12  2  0  0  0  0
 11 14  1  0  0  0  0
 17 19  1  0  0  0  0
 27  9  1  1  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
 26 27  1  0  0  0  0
 22 27  1  0  0  0  0
 26 28  1  6  0  0  0
 25 29  1  1  0  0  0
 24 30  1  6  0  0  0
 23 31  1  1  0  0  0
 31 32  1  0  0  0  0
 29 34  1  0  0  0  0
 36 33  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 34 37  2  0  0  0  0
 36 38  2  0  0  0  0
M  CHG  1   3   1
M  END
> <DATABASE_ID>
HMDB0301885

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C24H22O14/c25-8-17-20(33)23(38-19(32)7-18(30)31)21(34)24(37-17)36-16-6-11-13(28)4-10(26)5-15(11)35-22(16)9-1-2-12(27)14(29)3-9/h1-6,17,20-21,23-25,33-34H,7-8H2,(H4-,26,27,28,29,30,31)/p+1/t17-,20-,21-,23+,24-/m1/s1

> <INCHI_KEY>
AWPCCUSBXWEBBS-FYFHWUFJSA-O

> <FORMULA>
C24H23O14

> <MOLECULAR_WEIGHT>
535.431

> <EXACT_MASS>
535.108780444

> <JCHEM_ACCEPTOR_COUNT>
12

> <JCHEM_AVERAGE_POLARIZABILITY>
49.68507051984316

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
8

> <JCHEM_FORMAL_CHARGE>
1

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-{[(2S,3R,4S,5R,6R)-4-[(2-carboxyacetyl)oxy]-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-1λ⁴-chromen-1-ylium

> <ALOGPS_LOGP>
0.85

> <JCHEM_LOGP>
0.6754999999999987

> <ALOGPS_LOGS>
-3.09

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
6.388697761646535

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.355111887378936

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9811117507046605

> <JCHEM_POLAR_SURFACE_AREA>
236.80999999999995

> <JCHEM_REFRACTIVITY>
131.7531

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.67e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-{[(2S,3R,4S,5R,6R)-4-[(2-carboxyacetyl)oxy]-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-1λ⁴-chromen-1-ylium

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0301885
     RDKit          3D
Cyanidin 3-(3''-malonylglucoside)
 61 64  0  0  0  0  0  0  0  0999 V2000
   -8.5037   -2.1697   -0.3205 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3463   -1.8152   -0.7040 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0030   -2.1009   -2.0130 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4962   -1.1434    0.2903 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2081   -0.6125   -0.3080 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9558   -0.7430   -1.5254 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2931    0.0333    0.4933 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0566    0.5929    0.0623 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8940   -0.1397    0.7119 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.8723   -1.5004    0.3755 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6352    0.5609    0.3406 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5496   -0.1212    0.5380 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7316   -0.0154   -0.1354 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7986    0.9844   -1.1083 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9677    1.1396   -1.8241 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0962    2.1250   -2.8105 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0724    2.9919   -3.1266 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3167    2.2033   -3.4782 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3510    1.3439   -3.1739 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5359    1.4753   -3.8722 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1933    0.3940   -2.2057 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9868    0.2651   -1.4980 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8896   -0.6584   -0.5814 O   0  0  0  0  0  3  0  0  0  0  0  0
    2.7775   -0.8420    0.1316 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7889   -1.9217    1.1361 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6862   -2.2523    1.8541 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7111   -3.2739    2.8159 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8761   -3.9674    3.0482 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9006   -4.9781    3.9996 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9912   -3.6137    2.3039 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1784   -4.3065    2.5315 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9655   -2.6232    1.3733 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6655    1.8097    1.0036 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5973    2.5602    0.2456 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4356    4.0185    0.6002 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6690    4.2391    1.9521 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9808    2.0450    0.4608 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.8697    2.8289   -0.2735 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6307   -3.0426   -2.2194 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2023   -1.8835    1.0897 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9832   -0.2873    0.7984 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8980    0.4804   -1.0296 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0770   -0.0232    1.8180 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0586   -2.0141    1.2415 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6883    0.8610   -0.7454 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9989    1.6373   -1.3210 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1943    2.9708   -2.6797 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4293    2.9645   -4.2470 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2558    2.1088   -3.4902 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0029   -0.3056   -1.9342 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7210   -1.7922    1.7586 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8125   -3.5362    3.3918 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1128   -5.2500    4.5433 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0215   -4.0851    2.0172 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8333   -2.3352    0.7843 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3599    2.4390   -0.8319 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0695    4.6722   -0.0302 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3740    4.3329    0.4011 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9602    4.7876    2.3355 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2741    2.1373    1.5353 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6894    2.3512   -0.4960 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  9 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 16 18  1  0
 18 19  2  0
 19 20  1  0
 19 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 28 29  1  0
 28 30  1  0
 30 31  1  0
 30 32  2  0
 11 33  1  0
 33 34  1  0
 34 35  1  0
 35 36  1  0
 34 37  1  0
 37 38  1  0
 37  8  1  0
 24 13  1  0
 32 25  1  0
 22 15  1  0
  3 39  1  0
  4 40  1  0
  4 41  1  0
  8 42  1  6
  9 43  1  1
 10 44  1  0
 11 45  1  6
 14 46  1  0
 17 47  1  0
 18 48  1  0
 20 49  1  0
 21 50  1  0
 26 51  1  0
 27 52  1  0
 29 53  1  0
 31 54  1  0
 32 55  1  0
 34 56  1  6
 35 57  1  0
 35 58  1  0
 36 59  1  0
 37 60  1  1
 38 61  1  0
M  CHG  1  23   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       0.430   0.051   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.765   0.789   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -0.866   0.789   0.000  0.00  0.00           O+1
HETATM    4  C   UNK     0       0.430  -1.489   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.112   0.051   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.765   2.342   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.194   0.051   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.866  -2.265   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       1.765  -2.265   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       4.440   0.789   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.112   3.112   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -2.194  -1.489   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -3.555   0.789   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.440   2.342   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       5.762   0.006   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      -3.555  -2.265   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -4.889   0.051   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       5.781   3.112   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      -4.889  -1.489   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      -3.555  -3.812   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      -6.224   0.789   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       0.431  -4.575   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       0.431  -6.115   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       1.765  -6.885   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       3.098  -6.115   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       3.098  -4.575   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       1.765  -3.805   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       4.432  -3.805   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0       4.432  -6.885   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0       1.765  -8.425   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      -0.903  -6.885   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      -0.903  -8.425   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0       9.767  -6.885   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       5.766  -6.115   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       7.099  -6.885   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       8.433  -6.115   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0       5.766  -4.575   0.000  0.00  0.00           O+0
HETATM   38  O   UNK     0       8.433  -4.575   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   12   13                                                  
CONECT    8    4   12                                                       
CONECT    9    4   27                                                       
CONECT   10    5   14   15                                                  
CONECT   11    6   14                                                       
CONECT   12    7   16    8                                                  
CONECT   13    7   17                                                       
CONECT   14   10   18   11                                                  
CONECT   15   10                                                            
CONECT   16   12   19   20                                                  
CONECT   17   13   21   19                                                  
CONECT   18   14                                                            
CONECT   19   16   17                                                       
CONECT   20   16                                                            
CONECT   21   17                                                            
CONECT   22   23   27                                                       
CONECT   23   22   24   31                                                  
CONECT   24   23   25   30                                                  
CONECT   25   24   26   29                                                  
CONECT   26   25   27   28                                                  
CONECT   27    9   26   22                                                  
CONECT   28   26                                                            
CONECT   29   25   34                                                       
CONECT   30   24                                                            
CONECT   31   23   32                                                       
CONECT   32   31                                                            
CONECT   33   36                                                            
CONECT   34   29   35   37                                                  
CONECT   35   34   36                                                       
CONECT   36   33   35   38                                                  
CONECT   37   34                                                            
CONECT   38   36                                                            
MASTER        0    0    0    0    0    0    0    0   38    0   82    0
END

COMPND    HMDB0301885
HETATM    1  O1  UNL     1      -8.504  -2.170  -0.321  1.00  0.00           O  
HETATM    2  C1  UNL     1      -7.346  -1.815  -0.704  1.00  0.00           C  
HETATM    3  O2  UNL     1      -7.003  -2.101  -2.013  1.00  0.00           O  
HETATM    4  C2  UNL     1      -6.496  -1.143   0.290  1.00  0.00           C  
HETATM    5  C3  UNL     1      -5.208  -0.613  -0.308  1.00  0.00           C  
HETATM    6  O3  UNL     1      -4.956  -0.743  -1.525  1.00  0.00           O  
HETATM    7  O4  UNL     1      -4.293   0.033   0.493  1.00  0.00           O  
HETATM    8  C4  UNL     1      -3.057   0.593   0.062  1.00  0.00           C  
HETATM    9  C5  UNL     1      -1.894  -0.140   0.712  1.00  0.00           C  
HETATM   10  O5  UNL     1      -1.872  -1.500   0.375  1.00  0.00           O  
HETATM   11  C6  UNL     1      -0.635   0.561   0.341  1.00  0.00           C  
HETATM   12  O6  UNL     1       0.550  -0.121   0.538  1.00  0.00           O  
HETATM   13  C7  UNL     1       1.732  -0.015  -0.135  1.00  0.00           C  
HETATM   14  C8  UNL     1       1.799   0.984  -1.108  1.00  0.00           C  
HETATM   15  C9  UNL     1       2.968   1.140  -1.824  1.00  0.00           C  
HETATM   16  C10 UNL     1       3.096   2.125  -2.811  1.00  0.00           C  
HETATM   17  O7  UNL     1       2.072   2.992  -3.127  1.00  0.00           O  
HETATM   18  C11 UNL     1       4.317   2.203  -3.478  1.00  0.00           C  
HETATM   19  C12 UNL     1       5.351   1.344  -3.174  1.00  0.00           C  
HETATM   20  O8  UNL     1       6.536   1.475  -3.872  1.00  0.00           O  
HETATM   21  C13 UNL     1       5.193   0.394  -2.206  1.00  0.00           C  
HETATM   22  C14 UNL     1       3.987   0.265  -1.498  1.00  0.00           C  
HETATM   23  O9  UNL     1       3.890  -0.658  -0.581  1.00  0.00           O1+
HETATM   24  C15 UNL     1       2.778  -0.842   0.132  1.00  0.00           C  
HETATM   25  C16 UNL     1       2.789  -1.922   1.136  1.00  0.00           C  
HETATM   26  C17 UNL     1       1.686  -2.252   1.854  1.00  0.00           C  
HETATM   27  C18 UNL     1       1.711  -3.274   2.816  1.00  0.00           C  
HETATM   28  C19 UNL     1       2.876  -3.967   3.048  1.00  0.00           C  
HETATM   29  O10 UNL     1       2.901  -4.978   4.000  1.00  0.00           O  
HETATM   30  C20 UNL     1       3.991  -3.614   2.304  1.00  0.00           C  
HETATM   31  O11 UNL     1       5.178  -4.307   2.532  1.00  0.00           O  
HETATM   32  C21 UNL     1       3.965  -2.623   1.373  1.00  0.00           C  
HETATM   33  O12 UNL     1      -0.666   1.810   1.004  1.00  0.00           O  
HETATM   34  C22 UNL     1      -1.597   2.560   0.246  1.00  0.00           C  
HETATM   35  C23 UNL     1      -1.436   4.019   0.600  1.00  0.00           C  
HETATM   36  O13 UNL     1      -1.669   4.239   1.952  1.00  0.00           O  
HETATM   37  C24 UNL     1      -2.981   2.045   0.461  1.00  0.00           C  
HETATM   38  O14 UNL     1      -3.870   2.829  -0.273  1.00  0.00           O  
HETATM   39  H1  UNL     1      -6.631  -3.043  -2.219  1.00  0.00           H  
HETATM   40  H2  UNL     1      -6.202  -1.884   1.090  1.00  0.00           H  
HETATM   41  H3  UNL     1      -6.983  -0.287   0.798  1.00  0.00           H  
HETATM   42  H4  UNL     1      -2.898   0.480  -1.030  1.00  0.00           H  
HETATM   43  H5  UNL     1      -2.077  -0.023   1.818  1.00  0.00           H  
HETATM   44  H6  UNL     1      -2.059  -2.014   1.241  1.00  0.00           H  
HETATM   45  H7  UNL     1      -0.688   0.861  -0.745  1.00  0.00           H  
HETATM   46  H8  UNL     1       0.999   1.637  -1.321  1.00  0.00           H  
HETATM   47  H9  UNL     1       1.194   2.971  -2.680  1.00  0.00           H  
HETATM   48  H10 UNL     1       4.429   2.965  -4.247  1.00  0.00           H  
HETATM   49  H11 UNL     1       7.256   2.109  -3.490  1.00  0.00           H  
HETATM   50  H12 UNL     1       6.003  -0.306  -1.934  1.00  0.00           H  
HETATM   51  H13 UNL     1       0.721  -1.792   1.759  1.00  0.00           H  
HETATM   52  H14 UNL     1       0.813  -3.536   3.392  1.00  0.00           H  
HETATM   53  H15 UNL     1       2.113  -5.250   4.543  1.00  0.00           H  
HETATM   54  H16 UNL     1       6.022  -4.085   2.017  1.00  0.00           H  
HETATM   55  H17 UNL     1       4.833  -2.335   0.784  1.00  0.00           H  
HETATM   56  H18 UNL     1      -1.360   2.439  -0.832  1.00  0.00           H  
HETATM   57  H19 UNL     1      -2.069   4.672  -0.030  1.00  0.00           H  
HETATM   58  H20 UNL     1      -0.374   4.333   0.401  1.00  0.00           H  
HETATM   59  H21 UNL     1      -0.960   4.788   2.335  1.00  0.00           H  
HETATM   60  H22 UNL     1      -3.274   2.137   1.535  1.00  0.00           H  
HETATM   61  H23 UNL     1      -4.689   2.351  -0.496  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    4
CONECT    3   39
CONECT    4    5   40   41
CONECT    5    6    6    7
CONECT    7    8
CONECT    8    9   37   42
CONECT    9   10   11   43
CONECT   10   44
CONECT   11   12   33   45
CONECT   12   13
CONECT   13   14   14   24
CONECT   14   15   46
CONECT   15   16   16   22
CONECT   16   17   18
CONECT   17   47
CONECT   18   19   19   48
CONECT   19   20   21
CONECT   20   49
CONECT   21   22   22   50
CONECT   22   23
CONECT   23   24   24
CONECT   24   25
CONECT   25   26   26   32
CONECT   26   27   51
CONECT   27   28   28   52
CONECT   28   29   30
CONECT   29   53
CONECT   30   31   32   32
CONECT   31   54
CONECT   32   55
CONECT   33   34
CONECT   34   35   37   56
CONECT   35   36   57   58
CONECT   36   59
CONECT   37   38   60
CONECT   38   61
END

HMDB0301885
     RDKit          3D
Cyanidin 3-(3''-malonylglucoside)
 61 64  0  0  0  0  0  0  0  0999 V2000
   -8.5037   -2.1697   -0.3205 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3463   -1.8152   -0.7040 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0030   -2.1009   -2.0130 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4962   -1.1434    0.2903 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2081   -0.6125   -0.3080 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9558   -0.7430   -1.5254 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2931    0.0333    0.4933 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0566    0.5929    0.0623 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8940   -0.1397    0.7119 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.8723   -1.5004    0.3755 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6352    0.5609    0.3406 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5496   -0.1212    0.5380 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7316   -0.0154   -0.1354 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7986    0.9844   -1.1083 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9677    1.1396   -1.8241 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0962    2.1250   -2.8105 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0724    2.9919   -3.1266 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3167    2.2033   -3.4782 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3510    1.3439   -3.1739 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5359    1.4753   -3.8722 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1933    0.3940   -2.2057 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9868    0.2651   -1.4980 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8896   -0.6584   -0.5814 O   0  0  0  0  0  3  0  0  0  0  0  0
    2.7775   -0.8420    0.1316 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7889   -1.9217    1.1361 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6862   -2.2523    1.8541 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7111   -3.2739    2.8159 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8761   -3.9674    3.0482 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9006   -4.9781    3.9996 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9912   -3.6137    2.3039 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1784   -4.3065    2.5315 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9655   -2.6232    1.3733 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6655    1.8097    1.0036 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5973    2.5602    0.2456 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4356    4.0185    0.6002 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6690    4.2391    1.9521 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9808    2.0450    0.4608 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.8697    2.8289   -0.2735 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6307   -3.0426   -2.2194 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2023   -1.8835    1.0897 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9832   -0.2873    0.7984 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8980    0.4804   -1.0296 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0770   -0.0232    1.8180 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0586   -2.0141    1.2415 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6883    0.8610   -0.7454 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9989    1.6373   -1.3210 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1943    2.9708   -2.6797 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4293    2.9645   -4.2470 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2558    2.1088   -3.4902 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0029   -0.3056   -1.9342 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7210   -1.7922    1.7586 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8125   -3.5362    3.3918 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1128   -5.2500    4.5433 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0215   -4.0851    2.0172 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8333   -2.3352    0.7843 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3599    2.4390   -0.8319 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0695    4.6722   -0.0302 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3740    4.3329    0.4011 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9602    4.7876    2.3355 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2741    2.1373    1.5353 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6894    2.3512   -0.4960 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  9 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 16 18  1  0
 18 19  2  0
 19 20  1  0
 19 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 28 29  1  0
 28 30  1  0
 30 31  1  0
 30 32  2  0
 11 33  1  0
 33 34  1  0
 34 35  1  0
 35 36  1  0
 34 37  1  0
 37 38  1  0
 37  8  1  0
 24 13  1  0
 32 25  1  0
 22 15  1  0
  3 39  1  0
  4 40  1  0
  4 41  1  0
  8 42  1  6
  9 43  1  1
 10 44  1  0
 11 45  1  6
 14 46  1  0
 17 47  1  0
 18 48  1  0
 20 49  1  0
 21 50  1  0
 26 51  1  0
 27 52  1  0
 29 53  1  0
 31 54  1  0
 32 55  1  0
 34 56  1  6
 35 57  1  0
 35 58  1  0
 36 59  1  0
 37 60  1  1
 38 61  1  0
M  CHG  1  23   1
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₂₄H₂₃O₁₄

Average Molecular Weight

535.431

Monoisotopic Molecular Weight

535.108780444

IUPAC Name

3-{[(2S,3R,4S,5R,6R)-4-[(2-carboxyacetyl)oxy]-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-1λ⁴-chromen-1-ylium

Traditional Name

3-{[(2S,3R,4S,5R,6R)-4-[(2-carboxyacetyl)oxy]-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-1λ⁴-chromen-1-ylium

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C24H22O14/c25-8-17-20(33)23(38-19(32)7-18(30)31)21(34)24(37-17)36-16-6-11-13(28)4-10(26)5-15(11)35-22(16)9-1-2-12(27)14(29)3-9/h1-6,17,20-21,23-25,33-34H,7-8H2,(H4-,26,27,28,29,30,31)/p+1/t17-,20-,21-,23+,24-/m1/s1

InChI Key

AWPCCUSBXWEBBS-FYFHWUFJSA-O

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as anthocyanidin-3-o-glycosides. These are phenolic compounds containing one anthocyanidin moiety which is O-glycosidically linked to a carbohydrate moiety at the C3-position.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavonoid glycosides

Direct Parent

Anthocyanidin-3-O-glycosides

Alternative Parents

Substituents

Anthocyanidin-3-o-glycoside
Flavonoid-3-o-glycoside
Hydroxyflavonoid
3'-hydroxyflavonoid
4'-hydroxyflavonoid
5-hydroxyflavonoid
7-hydroxyflavonoid
Anthocyanidin
Hexose monosaccharide
O-glycosyl compound
Glycosyl compound
1-benzopyran
Benzopyran
Catechol
Phenol
1-hydroxy-2-unsubstituted benzenoid
1-hydroxy-4-unsubstituted benzenoid
Monocyclic benzene moiety
Benzenoid
Dicarboxylic acid or derivatives
1,3-dicarbonyl compound
Monosaccharide
Oxane
Heteroaromatic compound
Secondary alcohol
Carboxylic acid ester
Acetal
Oxacycle
Organoheterocyclic compound
Carboxylic acid derivative
Carboxylic acid
Organooxygen compound
Alcohol
Organic oxygen compound
Organic oxide
Carbonyl group
Primary alcohol
Hydrocarbon derivative
Organic cation
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Exogenous (HMDB: HMDB0301885)

Food

Herb and spice

Herb

Garlic (FooDB: FOOD00008)

Fruit

Berry

Blackberry (FooDB: FOOD00906)
Tropical highland blackberry (FooDB: FOOD00904)

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	0.85	ALOGPS
logP	0.68	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Acidic)	3.36	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	12	ChemAxon
Hydrogen Donor Count	8	ChemAxon
Polar Surface Area	236.81 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	131.75 m³·mol⁻¹	ChemAxon
Polarizability	49.69 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
AllCCS	[M+H]+	217.358	32859911
AllCCS	[M+H-H2O]+	215.608	32859911
AllCCS	[M+Na]+	219.401	32859911
AllCCS	[M+NH4]+	218.949	32859911
AllCCS	[M-H]-	215.609	32859911
AllCCS	[M+Na-2H]-	216.734	32859911
AllCCS	[M+HCOO]-	218.122	32859911
DeepCCS	[M+H]+	220.135	30932474
DeepCCS	[M-H]-	217.796	30932474
DeepCCS	[M-2H]-	251.036	30932474
DeepCCS	[M+Na]+	226.048	30932474

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Predicted by Siyang on May 30, 2022	11.3642 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	5.33 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2321.9 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	209.6 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	89.1 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	143.4 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	98.6 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	557.0 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	693.5 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	116.4 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	904.3 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	493.6 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	2009.4 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	357.2 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	382.3 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	684.6 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	110.0 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	406.9 seconds	40023050

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 - Cyanidin 3-(3''-malonylglucoside) 10V, Positive-QTOF	splash10-000i-0000090000-464e774cd54fc521934e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cyanidin 3-(3''-malonylglucoside) 20V, Positive-QTOF	splash10-00kr-1000190000-c16811598d4d2752ea1e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cyanidin 3-(3''-malonylglucoside) 40V, Positive-QTOF	splash10-01pd-9621030000-5cb6fa6100133938a176	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cyanidin 3-(3''-malonylglucoside) 10V, Negative-QTOF	splash10-001i-1000090000-534f8b91e10796dcbdcf	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cyanidin 3-(3''-malonylglucoside) 20V, Negative-QTOF	splash10-0a59-9000070000-2e348a41277c23435974	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cyanidin 3-(3''-malonylglucoside) 40V, Negative-QTOF	splash10-0pbc-9400000000-e27019d73ed4c52a092c	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

FDB001572

KNApSAcK ID

Not Available

Chemspider ID

30780065

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

102445481

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 Cyanidin 3-(3''-malonylglucoside) (HMDB0301885)

MOL for HMDB0301885 (Cyanidin 3-(3''-malonylglucoside))

3D MOL for HMDB0301885 (Cyanidin 3-(3''-malonylglucoside))

3D SDF for HMDB0301885 (Cyanidin 3-(3''-malonylglucoside))

3D-SDF for HMDB0301885 (Cyanidin 3-(3''-malonylglucoside))

PDB for HMDB0301885 (Cyanidin 3-(3''-malonylglucoside))

3D PDB for HMDB0301885 (Cyanidin 3-(3''-malonylglucoside))

SMILES for HMDB0301885 (Cyanidin 3-(3''-malonylglucoside))

INCHI for HMDB0301885 (Cyanidin 3-(3''-malonylglucoside))

Structure for HMDB0301885 (Cyanidin 3-(3''-malonylglucoside))

3D Structure for HMDB0301885 (Cyanidin 3-(3''-malonylglucoside))

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

MS/MS Spectra