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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2021-09-24 03:32:25 UTC

Update Date

2021-09-24 03:32:25 UTC

HMDB ID

HMDB0303647

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Pelargonidin 3-(6''-malonylglucoside)

Description

Pelargonidin 3-(6''-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. Pelargonidin 3-(6''-malonylglucoside) is practically insoluble (in water) and a weakly acidic compound (based on its pKa). Pelargonidin 3-(6''-malonylglucoside) can be found in cloudberry, lupine, red raspberry, and strawberry, which makes pelargonidin 3-(6''-malonylglucoside) a potential biomarker for the consumption of these food products.

Structure

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

Pelargonidin 3-O-(6''-malonyl-glucoside)
  Mrv1652309231720592D          

 37 40  0  0  1  0            999 V2000
    0.0000   -6.6000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -6.1875    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7145   -5.3625    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0000   -4.9499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -5.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.9499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.9499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -5.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -4.9499    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -5.3625    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.8579   -4.9499    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -7.8375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0012   -7.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7158   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4302   -7.8375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7158   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0012   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0012   -5.3625    0.0000 O   0  3  0  0  0  0  0  0  0  0  0  0
   -4.2868   -4.9499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0012   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0012   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868   -2.4749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -6.1875    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8579   -6.6000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -6.6000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4289   -7.4250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1  0  0  0
  2  3  1  0  0  0  0
  3  4  1  6  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  2  0  0  0  0
  3 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  6  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
 23 24  2  0  0  0  0
 17 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 15 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 30 31  1  0  0  0  0
 30 32  1  0  0  0  0
 32 33  2  0  0  0  0
 27 33  1  0  0  0  0
 13 34  1  0  0  0  0
 34 35  1  1  0  0  0
 34 36  1  0  0  0  0
  2 36  1  0  0  0  0
 36 37  1  6  0  0  0
M  CHG  1  25   1
M  END

HMDB0303647
     RDKit          3D
Pelargonidin 3-(6''-malonylglucoside)
 60 63  0  0  0  0  0  0  0  0999 V2000
    6.4098    3.0358   -0.9300 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2625    2.1209   -1.0584 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6035    2.3823   -0.9250 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7868    0.7576   -1.3564 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2917    0.7181   -1.4561 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6194    1.7435   -1.2970 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6754   -0.4709   -1.7263 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2891   -0.6830   -1.8506 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5888   -0.3318   -0.5422 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2176   -0.5569   -0.6879 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5268   -0.2915    0.4966 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8132   -0.5532    0.2546 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9218    0.2078    0.2980 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7616    1.5506    0.6524 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8730    2.3564    0.7065 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7660    3.6959    1.0532 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4997    4.1838    1.3406 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8891    4.4927    1.1035 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1185    3.9413    0.8052 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2692    4.7477    0.8543 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2007    2.6190    0.4660 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0812    1.7865    0.4064 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1946    0.5365    0.0811 O   0  0  0  0  0  3  0  0  0  0  0  0
   -3.1594   -0.3037    0.0084 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4347   -1.6747   -0.3682 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4770   -2.6359   -0.4818 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8025   -3.9487   -0.8504 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1158   -4.2542   -1.0978 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4639   -5.5471   -1.4643 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1090   -3.3115   -0.9933 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7603   -2.0382   -0.6315 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9574   -1.2511    1.6014 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5180   -0.4923    2.6217 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0532   -2.1210    1.0250 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6227   -2.8148   -0.1042 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1454   -1.1595    0.5668 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.4444   -0.3244    1.6413 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.1550    2.0727   -0.1331 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1649    0.4016   -2.3364 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0692    0.0299   -0.5701 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0738   -1.7237   -2.1485 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8960   -0.0270   -2.6808 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7915    0.7384   -0.3295 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6918    0.7485    0.7784 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8184    1.9812    0.8832 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3438    5.1500    1.6009 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8157    5.5448    1.3745 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5143    5.2237   -0.0244 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1802    2.1791    0.2282 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4243   -2.4580   -0.3002 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0129   -4.6845   -0.9302 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7074   -6.2500   -0.7533 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1564   -3.5719   -1.1948 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5569   -1.2812   -0.5475 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1312   -1.8214    2.0233 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5864   -1.0604    3.4342 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4379   -2.8586    1.7556 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8099   -3.3330    0.0415 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0499   -1.7333    0.2792 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3713    0.6212    1.3884 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
 10 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  2  0
 11 32  1  0
 32 33  1  0
 32 34  1  0
 34 35  1  0
 34 36  1  0
 36 37  1  0
 36  9  1  0
 24 13  1  0
 31 25  1  0
 22 15  1  0
  3 38  1  0
  4 39  1  0
  4 40  1  0
  8 41  1  0
  8 42  1  0
  9 43  1  1
 11 44  1  1
 14 45  1  0
 17 46  1  0
 18 47  1  0
 20 48  1  0
 21 49  1  0
 26 50  1  0
 27 51  1  0
 29 52  1  0
 30 53  1  0
 31 54  1  0
 32 55  1  1
 33 56  1  0
 34 57  1  1
 35 58  1  0
 36 59  1  6
 37 60  1  0
M  CHG  1  23   1
M  END

Pelargonidin 3-O-(6''-malonyl-glucoside)
  Mrv1652309231720592D          

 37 40  0  0  1  0            999 V2000
    0.0000   -6.6000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -6.1875    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7145   -5.3625    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0000   -4.9499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -5.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.9499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.9499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -5.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -4.9499    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -5.3625    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.8579   -4.9499    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -7.8375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0012   -7.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7158   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4302   -7.8375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7158   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0012   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0012   -5.3625    0.0000 O   0  3  0  0  0  0  0  0  0  0  0  0
   -4.2868   -4.9499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0012   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0012   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868   -2.4749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -6.1875    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8579   -6.6000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -6.6000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4289   -7.4250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1  0  0  0
  2  3  1  0  0  0  0
  3  4  1  6  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  2  0  0  0  0
  3 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  6  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
 23 24  2  0  0  0  0
 17 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 15 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 30 31  1  0  0  0  0
 30 32  1  0  0  0  0
 32 33  2  0  0  0  0
 27 33  1  0  0  0  0
 13 34  1  0  0  0  0
 34 35  1  1  0  0  0
 34 36  1  0  0  0  0
  2 36  1  0  0  0  0
 36 37  1  6  0  0  0
M  CHG  1  25   1
M  END
> <DATABASE_ID>
HMDB0303647

> <DATABASE_NAME>
hmdb

> <SMILES>
O[C@@H]1[C@@H](COC(=O)CC(O)=O)O[C@@H](OC2=CC3=C(O)C=C(O)C=C3[O+]=C2C2=CC=C(O)C=C2)[C@H](O)[C@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C24H22O13/c25-11-3-1-10(2-4-11)23-16(7-13-14(27)5-12(26)6-15(13)35-23)36-24-22(33)21(32)20(31)17(37-24)9-34-19(30)8-18(28)29/h1-7,17,20-22,24,31-33H,8-9H2,(H3-,25,26,27,28,29)/p+1/t17-,20-,21+,22-,24-/m1/s1

> <INCHI_KEY>
XLZUBCUKXQFBKB-JZWLZXDTSA-O

> <FORMULA>
C24H23O13

> <MOLECULAR_WEIGHT>
519.4316

> <EXACT_MASS>
519.113865822

> <JCHEM_ACCEPTOR_COUNT>
12

> <JCHEM_ATOM_COUNT>
60

> <JCHEM_AVERAGE_POLARIZABILITY>
48.88325338945592

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
1

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
1.90

> <JCHEM_LOGP>
0.9598999999999989

> <ALOGPS_LOGS>
-3.25

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
6.397137470862175

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.2955237885215536

> <JCHEM_PKA_STRONGEST_BASIC>
-3.64910309071837

> <JCHEM_POLAR_SURFACE_AREA>
216.57999999999998

> <JCHEM_REFRACTIVITY>
129.77219999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.14e-01 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0303647
     RDKit          3D
Pelargonidin 3-(6''-malonylglucoside)
 60 63  0  0  0  0  0  0  0  0999 V2000
    6.4098    3.0358   -0.9300 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2625    2.1209   -1.0584 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6035    2.3823   -0.9250 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7868    0.7576   -1.3564 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2917    0.7181   -1.4561 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6194    1.7435   -1.2970 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6754   -0.4709   -1.7263 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2891   -0.6830   -1.8506 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5888   -0.3318   -0.5422 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2176   -0.5569   -0.6879 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5268   -0.2915    0.4966 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8132   -0.5532    0.2546 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9218    0.2078    0.2980 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7616    1.5506    0.6524 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8730    2.3564    0.7065 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7660    3.6959    1.0532 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4997    4.1838    1.3406 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8891    4.4927    1.1035 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1185    3.9413    0.8052 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2692    4.7477    0.8543 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2007    2.6190    0.4660 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0812    1.7865    0.4064 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1946    0.5365    0.0811 O   0  0  0  0  0  3  0  0  0  0  0  0
   -3.1594   -0.3037    0.0084 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4347   -1.6747   -0.3682 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4770   -2.6359   -0.4818 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8025   -3.9487   -0.8504 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1158   -4.2542   -1.0978 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4639   -5.5471   -1.4643 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1090   -3.3115   -0.9933 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7603   -2.0382   -0.6315 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9574   -1.2511    1.6014 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5180   -0.4923    2.6217 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0532   -2.1210    1.0250 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6227   -2.8148   -0.1042 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1454   -1.1595    0.5668 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.4444   -0.3244    1.6413 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.1550    2.0727   -0.1331 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1649    0.4016   -2.3364 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0692    0.0299   -0.5701 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0738   -1.7237   -2.1485 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8960   -0.0270   -2.6808 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7915    0.7384   -0.3295 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6918    0.7485    0.7784 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8184    1.9812    0.8832 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3438    5.1500    1.6009 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8157    5.5448    1.3745 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5143    5.2237   -0.0244 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1802    2.1791    0.2282 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4243   -2.4580   -0.3002 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0129   -4.6845   -0.9302 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7074   -6.2500   -0.7533 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1564   -3.5719   -1.1948 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5569   -1.2812   -0.5475 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1312   -1.8214    2.0233 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5864   -1.0604    3.4342 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4379   -2.8586    1.7556 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8099   -3.3330    0.0415 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0499   -1.7333    0.2792 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3713    0.6212    1.3884 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
 10 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  2  0
 11 32  1  0
 32 33  1  0
 32 34  1  0
 34 35  1  0
 34 36  1  0
 36 37  1  0
 36  9  1  0
 24 13  1  0
 31 25  1  0
 22 15  1  0
  3 38  1  0
  4 39  1  0
  4 40  1  0
  8 41  1  0
  8 42  1  0
  9 43  1  1
 11 44  1  1
 14 45  1  0
 17 46  1  0
 18 47  1  0
 20 48  1  0
 21 49  1  0
 26 50  1  0
 27 51  1  0
 29 52  1  0
 30 53  1  0
 31 54  1  0
 32 55  1  1
 33 56  1  0
 34 57  1  1
 35 58  1  0
 36 59  1  6
 37 60  1  0
M  CHG  1  23   1
M  END

HEADER    PROTEIN                                 23-SEP-17   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: Pelargonidin 3-O-(6''-malonyl-glucoside)          
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-SEP-17         0                                  
HETATM    1  O   UNK     0       0.000 -12.320   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      -1.334 -11.550   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.334 -10.010   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000  -9.240   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       1.334 -10.010   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       2.667  -9.240   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       2.667  -7.700   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       4.001 -10.010   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.335  -9.240   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       6.668 -10.010   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       5.335  -7.700   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0      -2.667  -9.240   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      -4.001 -10.010   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      -5.335  -9.240   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      -6.668 -10.010   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -6.668 -11.550   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -8.002 -12.320   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -8.002 -13.860   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -6.668 -14.630   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      -9.336 -14.630   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0     -10.669 -13.860   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0     -12.003 -14.630   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0     -10.669 -12.320   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -9.336 -11.550   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      -9.336 -10.010   0.000  0.00  0.00           O+1
HETATM   26  C   UNK     0      -8.002  -9.240   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -8.002  -7.700   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -9.336  -6.930   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -9.336  -5.390   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -8.002  -4.620   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      -8.002  -3.080   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      -6.668  -5.390   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -6.668  -6.930   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      -4.001 -11.550   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0      -5.335 -12.320   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0      -2.667 -12.320   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0      -2.667 -13.860   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   36                                                  
CONECT    3    2    4   12                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9                                                            
CONECT   12    3   13                                                       
CONECT   13   12   14   34                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   26                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   24                                                  
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24                                                       
CONECT   24   23   17   25                                                  
CONECT   25   24   26                                                       
CONECT   26   25   15   27                                                  
CONECT   27   26   28   33                                                  
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30   33                                                       
CONECT   33   32   27                                                       
CONECT   34   13   35   36                                                  
CONECT   35   34                                                            
CONECT   36   34    2   37                                                  
CONECT   37   36                                                            
MASTER        0    0    0    0    0    0    0    0   37    0   80    0
END

COMPND    HMDB0303647
HETATM    1  O1  UNL     1       6.410   3.036  -0.930  1.00  0.00           O  
HETATM    2  C1  UNL     1       7.262   2.121  -1.058  1.00  0.00           C  
HETATM    3  O2  UNL     1       8.604   2.382  -0.925  1.00  0.00           O  
HETATM    4  C2  UNL     1       6.787   0.758  -1.356  1.00  0.00           C  
HETATM    5  C3  UNL     1       5.292   0.718  -1.456  1.00  0.00           C  
HETATM    6  O3  UNL     1       4.619   1.744  -1.297  1.00  0.00           O  
HETATM    7  O4  UNL     1       4.675  -0.471  -1.726  1.00  0.00           O  
HETATM    8  C4  UNL     1       3.289  -0.683  -1.851  1.00  0.00           C  
HETATM    9  C5  UNL     1       2.589  -0.332  -0.542  1.00  0.00           C  
HETATM   10  O5  UNL     1       1.218  -0.557  -0.688  1.00  0.00           O  
HETATM   11  C6  UNL     1       0.527  -0.292   0.497  1.00  0.00           C  
HETATM   12  O6  UNL     1      -0.813  -0.553   0.255  1.00  0.00           O  
HETATM   13  C7  UNL     1      -1.922   0.208   0.298  1.00  0.00           C  
HETATM   14  C8  UNL     1      -1.762   1.551   0.652  1.00  0.00           C  
HETATM   15  C9  UNL     1      -2.873   2.356   0.707  1.00  0.00           C  
HETATM   16  C10 UNL     1      -2.766   3.696   1.053  1.00  0.00           C  
HETATM   17  O7  UNL     1      -1.500   4.184   1.341  1.00  0.00           O  
HETATM   18  C11 UNL     1      -3.889   4.493   1.104  1.00  0.00           C  
HETATM   19  C12 UNL     1      -5.119   3.941   0.805  1.00  0.00           C  
HETATM   20  O8  UNL     1      -6.269   4.748   0.854  1.00  0.00           O  
HETATM   21  C13 UNL     1      -5.201   2.619   0.466  1.00  0.00           C  
HETATM   22  C14 UNL     1      -4.081   1.787   0.406  1.00  0.00           C  
HETATM   23  O9  UNL     1      -4.195   0.537   0.081  1.00  0.00           O1+
HETATM   24  C15 UNL     1      -3.159  -0.304   0.008  1.00  0.00           C  
HETATM   25  C16 UNL     1      -3.435  -1.675  -0.368  1.00  0.00           C  
HETATM   26  C17 UNL     1      -2.477  -2.636  -0.482  1.00  0.00           C  
HETATM   27  C18 UNL     1      -2.802  -3.949  -0.850  1.00  0.00           C  
HETATM   28  C19 UNL     1      -4.116  -4.254  -1.098  1.00  0.00           C  
HETATM   29  O10 UNL     1      -4.464  -5.547  -1.464  1.00  0.00           O  
HETATM   30  C20 UNL     1      -5.109  -3.311  -0.993  1.00  0.00           C  
HETATM   31  C21 UNL     1      -4.760  -2.038  -0.632  1.00  0.00           C  
HETATM   32  C22 UNL     1       0.957  -1.251   1.601  1.00  0.00           C  
HETATM   33  O11 UNL     1       1.518  -0.492   2.622  1.00  0.00           O  
HETATM   34  C23 UNL     1       2.053  -2.121   1.025  1.00  0.00           C  
HETATM   35  O12 UNL     1       1.623  -2.815  -0.104  1.00  0.00           O  
HETATM   36  C24 UNL     1       3.145  -1.160   0.567  1.00  0.00           C  
HETATM   37  O13 UNL     1       3.444  -0.324   1.641  1.00  0.00           O  
HETATM   38  H1  UNL     1       9.155   2.073  -0.133  1.00  0.00           H  
HETATM   39  H2  UNL     1       7.165   0.402  -2.336  1.00  0.00           H  
HETATM   40  H3  UNL     1       7.069   0.030  -0.570  1.00  0.00           H  
HETATM   41  H4  UNL     1       3.074  -1.724  -2.148  1.00  0.00           H  
HETATM   42  H5  UNL     1       2.896  -0.027  -2.681  1.00  0.00           H  
HETATM   43  H6  UNL     1       2.791   0.738  -0.330  1.00  0.00           H  
HETATM   44  H7  UNL     1       0.692   0.748   0.778  1.00  0.00           H  
HETATM   45  H8  UNL     1      -0.818   1.981   0.883  1.00  0.00           H  
HETATM   46  H9  UNL     1      -1.344   5.150   1.601  1.00  0.00           H  
HETATM   47  H10 UNL     1      -3.816   5.545   1.374  1.00  0.00           H  
HETATM   48  H11 UNL     1      -6.514   5.224  -0.024  1.00  0.00           H  
HETATM   49  H12 UNL     1      -6.180   2.179   0.228  1.00  0.00           H  
HETATM   50  H13 UNL     1      -1.424  -2.458  -0.300  1.00  0.00           H  
HETATM   51  H14 UNL     1      -2.013  -4.684  -0.930  1.00  0.00           H  
HETATM   52  H15 UNL     1      -4.707  -6.250  -0.753  1.00  0.00           H  
HETATM   53  H16 UNL     1      -6.156  -3.572  -1.195  1.00  0.00           H  
HETATM   54  H17 UNL     1      -5.557  -1.281  -0.547  1.00  0.00           H  
HETATM   55  H18 UNL     1       0.131  -1.821   2.023  1.00  0.00           H  
HETATM   56  H19 UNL     1       1.586  -1.060   3.434  1.00  0.00           H  
HETATM   57  H20 UNL     1       2.438  -2.859   1.756  1.00  0.00           H  
HETATM   58  H21 UNL     1       0.810  -3.333   0.042  1.00  0.00           H  
HETATM   59  H22 UNL     1       4.050  -1.733   0.279  1.00  0.00           H  
HETATM   60  H23 UNL     1       3.371   0.621   1.388  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    4
CONECT    3   38
CONECT    4    5   39   40
CONECT    5    6    6    7
CONECT    7    8
CONECT    8    9   41   42
CONECT    9   10   36   43
CONECT   10   11
CONECT   11   12   32   44
CONECT   12   13
CONECT   13   14   14   24
CONECT   14   15   45
CONECT   15   16   16   22
CONECT   16   17   18
CONECT   17   46
CONECT   18   19   19   47
CONECT   19   20   21
CONECT   20   48
CONECT   21   22   22   49
CONECT   22   23
CONECT   23   24   24
CONECT   24   25
CONECT   25   26   26   31
CONECT   26   27   50
CONECT   27   28   28   51
CONECT   28   29   30
CONECT   29   52
CONECT   30   31   31   53
CONECT   31   54
CONECT   32   33   34   55
CONECT   33   56
CONECT   34   35   36   57
CONECT   35   58
CONECT   36   37   59
CONECT   37   60
END

HMDB0303647
     RDKit          3D
Pelargonidin 3-(6''-malonylglucoside)
 60 63  0  0  0  0  0  0  0  0999 V2000
    6.4098    3.0358   -0.9300 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2625    2.1209   -1.0584 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6035    2.3823   -0.9250 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7868    0.7576   -1.3564 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2917    0.7181   -1.4561 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6194    1.7435   -1.2970 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6754   -0.4709   -1.7263 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2891   -0.6830   -1.8506 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5888   -0.3318   -0.5422 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2176   -0.5569   -0.6879 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5268   -0.2915    0.4966 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8132   -0.5532    0.2546 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9218    0.2078    0.2980 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7616    1.5506    0.6524 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8730    2.3564    0.7065 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7660    3.6959    1.0532 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4997    4.1838    1.3406 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8891    4.4927    1.1035 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1185    3.9413    0.8052 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2692    4.7477    0.8543 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2007    2.6190    0.4660 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0812    1.7865    0.4064 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1946    0.5365    0.0811 O   0  0  0  0  0  3  0  0  0  0  0  0
   -3.1594   -0.3037    0.0084 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4347   -1.6747   -0.3682 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4770   -2.6359   -0.4818 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8025   -3.9487   -0.8504 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1158   -4.2542   -1.0978 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4639   -5.5471   -1.4643 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1090   -3.3115   -0.9933 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7603   -2.0382   -0.6315 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9574   -1.2511    1.6014 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5180   -0.4923    2.6217 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0532   -2.1210    1.0250 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6227   -2.8148   -0.1042 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1454   -1.1595    0.5668 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.4444   -0.3244    1.6413 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.1550    2.0727   -0.1331 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1649    0.4016   -2.3364 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0692    0.0299   -0.5701 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0738   -1.7237   -2.1485 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8960   -0.0270   -2.6808 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7915    0.7384   -0.3295 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6918    0.7485    0.7784 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8184    1.9812    0.8832 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3438    5.1500    1.6009 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8157    5.5448    1.3745 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5143    5.2237   -0.0244 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1802    2.1791    0.2282 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4243   -2.4580   -0.3002 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0129   -4.6845   -0.9302 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7074   -6.2500   -0.7533 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1564   -3.5719   -1.1948 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5569   -1.2812   -0.5475 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1312   -1.8214    2.0233 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5864   -1.0604    3.4342 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4379   -2.8586    1.7556 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8099   -3.3330    0.0415 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0499   -1.7333    0.2792 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3713    0.6212    1.3884 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
 10 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  2  0
 11 32  1  0
 32 33  1  0
 32 34  1  0
 34 35  1  0
 34 36  1  0
 36 37  1  0
 36  9  1  0
 24 13  1  0
 31 25  1  0
 22 15  1  0
  3 38  1  0
  4 39  1  0
  4 40  1  0
  8 41  1  0
  8 42  1  0
  9 43  1  1
 11 44  1  1
 14 45  1  0
 17 46  1  0
 18 47  1  0
 20 48  1  0
 21 49  1  0
 26 50  1  0
 27 51  1  0
 29 52  1  0
 30 53  1  0
 31 54  1  0
 32 55  1  1
 33 56  1  0
 34 57  1  1
 35 58  1  0
 36 59  1  6
 37 60  1  0
M  CHG  1  23   1
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Pelargonidin 3-O-(6-O-malonyl-b-D-glucoside)	Generator
Pelargonidin 3-O-(6-O-malonyl-β-D-glucoside)	Generator

Chemical Formula

C₂₄H₂₃O₁₃

Average Molecular Weight

519.4316

Monoisotopic Molecular Weight

519.113865822

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

O[C@@H]1[C@@H](COC(=O)CC(O)=O)O[C@@H](OC2=CC3=C(O)C=C(O)C=C3[O+]=C2C2=CC=C(O)C=C2)[C@H](O)[C@H]1O

InChI Identifier

InChI=1S/C24H22O13/c25-11-3-1-10(2-4-11)23-16(7-13-14(27)5-12(26)6-15(13)35-23)36-24-22(33)21(32)20(31)17(37-24)9-34-19(30)8-18(28)29/h1-7,17,20-22,24,31-33H,8-9H2,(H3-,25,26,27,28,29)/p+1/t17-,20-,21+,22-,24-/m1/s1

InChI Key

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

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

beta-D-glucoside (CHEBI:31965 )
anthocyanin cation (CHEBI:31965 )
Anthocyanidins (C12642 )
Anthocyanidins and anthocyanins (C12642 )

Ontology

Not Available

Exogenous (HMDB: HMDB0303647)

Lupine (FooDB: FOOD00104)

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	1.9	ALOGPS
logP	0.96	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	3.3	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	12	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	216.58 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	129.77 m³·mol⁻¹	ChemAxon
Polarizability	48.88 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]+	215.449	32859911
AllCCS	[M+H-H2O]+	213.628	32859911
AllCCS	[M+Na]+	217.58	32859911
AllCCS	[M+NH4]+	217.109	32859911
AllCCS	[M-H]-	212.935	32859911
AllCCS	[M+Na-2H]-	213.99	32859911
AllCCS	[M+HCOO]-	215.302	32859911
DeepCCS	[M+H]+	210.119	30932474
DeepCCS	[M-H]-	207.777	30932474
DeepCCS	[M-2H]-	241.222	30932474
DeepCCS	[M+Na]+	215.906	30932474

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Predicted by Siyang on May 30, 2022	11.2252 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	5.17 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2939.5 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	227.3 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	144.4 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	164.8 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	122.2 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	691.8 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	637.8 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	112.2 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1033.3 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	483.5 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	2043.0 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	384.0 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	500.1 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	483.9 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	150.8 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	190.4 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 - Pelargonidin 3-(6''-malonylglucoside) 10V, Positive-QTOF	splash10-00di-0000090000-cb1a1b98c6c9e5c97914	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pelargonidin 3-(6''-malonylglucoside) 20V, Positive-QTOF	splash10-00di-0000290000-f4973fa1969c99f8a909	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pelargonidin 3-(6''-malonylglucoside) 40V, Positive-QTOF	splash10-0gxw-7930020000-5c614c6c09dbf076ba11	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pelargonidin 3-(6''-malonylglucoside) 10V, Negative-QTOF	splash10-014i-1000090000-1c8d9cf6a3f493a72215	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pelargonidin 3-(6''-malonylglucoside) 20V, Negative-QTOF	splash10-066r-9100160000-f5dba1ee5c7b0ae723ed	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pelargonidin 3-(6''-malonylglucoside) 40V, Negative-QTOF	splash10-0pb9-9600000000-dc27c6e2da063fe4f3fa	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

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

443913

PDB ID

Not Available

ChEBI ID

31965

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-(6''-malonylglucoside) (HMDB0303647)

MOL for HMDB0303647 (Pelargonidin 3-(6''-malonylglucoside))

3D MOL for HMDB0303647 (Pelargonidin 3-(6''-malonylglucoside))

3D SDF for HMDB0303647 (Pelargonidin 3-(6''-malonylglucoside))

3D-SDF for HMDB0303647 (Pelargonidin 3-(6''-malonylglucoside))

PDB for HMDB0303647 (Pelargonidin 3-(6''-malonylglucoside))

3D PDB for HMDB0303647 (Pelargonidin 3-(6''-malonylglucoside))

SMILES for HMDB0303647 (Pelargonidin 3-(6''-malonylglucoside))

INCHI for HMDB0303647 (Pelargonidin 3-(6''-malonylglucoside))

Structure for HMDB0303647 (Pelargonidin 3-(6''-malonylglucoside))

3D Structure for HMDB0303647 (Pelargonidin 3-(6''-malonylglucoside))

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

MS/MS Spectra