NP-MRD: Showing NP-Card for 5,7-dihydroxy-3-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2-(3,4,5-trihydroxyphenyl)-1λ⁴-chromen-1-ylium (NP0259827)

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Record Information

Version

2.0

Created at

2022-09-08 01:49:35 UTC

Updated at

2022-09-08 01:49:35 UTC

NP-MRD ID

NP0259827

Secondary Accession Numbers

None

Natural Product Identification

Common Name

5,7-dihydroxy-3-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2-(3,4,5-trihydroxyphenyl)-1λ⁴-chromen-1-ylium

Description

5,7-Dihydroxy-3-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2-(3,4,5-trihydroxyphenyl)-1λ⁴-chromen-1-ylium belongs to the class of organic compounds known as diterpene glycosides. These are diterpenoids in which an isoprene unit is glycosylated. 5,7-Dihydroxy-3-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2-(3,4,5-trihydroxyphenyl)-1λ⁴-chromen-1-ylium is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, 5,7-dihydroxy-3-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2-(3,4,5-trihydroxyphenyl)-1λ⁴-chromen-1-ylium is found, on average, in the highest concentration within a few different foods, such as bilberries, highbush blueberries, and lowbush blueberries. 5,7-Dihydroxy-3-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2-(3,4,5-trihydroxyphenyl)-1λ⁴-chromen-1-ylium has also been detected, but not quantified in, several different foods, such as strawberries, black chokeberries, black crowberries, blackcurrants, and cereals and cereal products. 5,7-dihydroxy-3-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2-(3,4,5-trihydroxyphenyl)-1λ⁴-chromen-1-ylium is found in Vaccinium corymbosum and Vaccinium myrtillus. This could make 5,7-dihydroxy-3-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2-(3,4,5-trihydroxyphenyl)-1λ⁴-chromen-1-ylium a potential biomarker for the consumption of these foods.

Structure

MOL 3D MOL SDF PDB SMILES InChI

Delphinidin 3-O-galactoside
  Mrv1652309231718162D          

 33 36  0  0  0  0            999 V2000
   -1.4289    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    2.4749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2374    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2374    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
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 O   0  3  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -2.4749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -1.2374    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4749    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
 15 16  2  0  0  0  0
  9 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
  7 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  2  0  0  0  0
 23 24  1  0  0  0  0
 23 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  2  0  0  0  0
 19 27  1  0  0  0  0
  5 28  1  0  0  0  0
 28 29  1  0  0  0  0
 28 30  1  0  0  0  0
 30 31  1  0  0  0  0
 30 32  1  0  0  0  0
  3 32  1  0  0  0  0
 32 33  1  0  0  0  0
M  CHG  1  17   1
M  END

     RDKit          3D

 54 57  0  0  0  0  0  0  0  0999 V2000
    4.5228   -2.2493    0.0367 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5399   -1.4148    1.1239 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6843   -0.1725    0.9388 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3725   -0.5570    0.7202 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6821    0.3491   -0.0912 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3597   -0.0636   -0.1176 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7942    0.5663    0.1710 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7263    1.9085    0.5882 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8805    2.5855    0.8917 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7941    3.9052    1.3004 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6183    4.6175    1.4326 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0155    4.5397    1.5958 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2283    3.9191    1.4954 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3855    4.6131    1.8045 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2709    2.6098    1.0866 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1030    1.9231    0.7789 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1265    0.6858    0.3913 O   0  0  0  0  0  3  0  0  0  0  0  0
   -2.0286   -0.0178    0.0838 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2330   -1.4040   -0.3366 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5524   -1.8875   -0.3859 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7985   -3.1883   -0.7760 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1185   -3.6466   -0.8174 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7908   -4.0501   -1.1257 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9487   -5.3599   -1.5256 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4908   -3.5799   -1.0791 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4376   -4.4103   -1.4224 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2303   -2.2561   -0.6828 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2397    0.2228   -1.4988 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0757   -1.0719   -1.9412 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6909    0.6220   -1.4454 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.4056   -0.3118   -2.2135 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2277    0.7767   -0.0645 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.6276    0.6037   -0.1395 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8909   -3.0034    0.1375 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1407   -1.9614    2.0030 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5904   -1.1161    1.3415 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6981    0.3455    1.9401 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8089    1.3807    0.2238 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2074    2.4094    0.6728 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2655    4.2230    1.2392 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9416    5.5682    1.9138 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9115    5.1457    1.1175 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2172    2.1063    1.0022 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3593   -1.2450   -0.1208 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3125   -4.5683   -1.0923 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8545   -5.7669   -1.5831 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4969   -4.0342   -1.3769 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2010   -1.9312   -0.6607 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6788    0.9493   -2.1220 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1272   -1.7355   -1.2127 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8309    1.6095   -1.9692 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0853    0.1341   -2.7806 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0966    1.8331    0.2936 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0237    0.8508    0.7365 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 10 12  1  0
 12 13  2  0
 13 14  1  0
 13 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  1  0
 21 23  2  0
 23 24  1  0
 23 25  1  0
 25 26  1  0
 25 27  2  0
  5 28  1  0
 28 29  1  0
 28 30  1  0
 30 31  1  0
 30 32  1  0
 32 33  1  0
 32  3  1  0
 18  7  1  0
 27 19  1  0
 16  9  1  0
  1 34  1  0
  2 35  1  0
  2 36  1  0
  3 37  1  1
  5 38  1  1
  8 39  1  0
 11 40  1  0
 12 41  1  0
 14 42  1  0
 15 43  1  0
 20 44  1  0
 22 45  1  0
 24 46  1  0
 26 47  1  0
 27 48  1  0
 28 49  1  6
 29 50  1  0
 30 51  1  6
 31 52  1  0
 32 53  1  1
 33 54  1  0
M  CHG  1  17   1
M  END

Delphinidin 3-O-galactoside
  Mrv1652309231718162D          

 33 36  0  0  0  0            999 V2000
   -1.4289    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    2.4749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2374    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2374    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
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 O   0  3  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -2.4749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -1.2374    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4749    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
 15 16  2  0  0  0  0
  9 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
  7 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  2  0  0  0  0
 23 24  1  0  0  0  0
 23 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  2  0  0  0  0
 19 27  1  0  0  0  0
  5 28  1  0  0  0  0
 28 29  1  0  0  0  0
 28 30  1  0  0  0  0
 30 31  1  0  0  0  0
 30 32  1  0  0  0  0
  3 32  1  0  0  0  0
 32 33  1  0  0  0  0
M  CHG  1  17   1
M  END
> <DATABASE_ID>
NP0259827

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OCC1OC(OC2=CC3=C(O)C=C(O)C=C3[O+]=C2C2=CC(O)=C(O)C(O)=C2)C(O)C(O)C1O

> <INCHI_IDENTIFIER>
InChI=1S/C21H20O12/c22-6-15-17(28)18(29)19(30)21(33-15)32-14-5-9-10(24)3-8(23)4-13(9)31-20(14)7-1-11(25)16(27)12(26)2-7/h1-5,15,17-19,21-22,28-30H,6H2,(H4-,23,24,25,26,27)/p+1

> <INCHI_KEY>
XENHPQQLDPAYIJ-UHFFFAOYSA-O

> <FORMULA>
C21H21O12

> <MOLECULAR_WEIGHT>
465.3842

> <EXACT_MASS>
465.103301136

> <JCHEM_ACCEPTOR_COUNT>
12

> <JCHEM_ATOM_COUNT>
54

> <JCHEM_AVERAGE_POLARIZABILITY>
43.559981705934895

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
9

> <JCHEM_FORMAL_CHARGE>
1

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5,7-dihydroxy-3-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2-(3,4,5-trihydroxyphenyl)-1lambda4-chromen-1-ylium

> <ALOGPS_LOGP>
0.93

> <JCHEM_LOGP>
0.10259999999999869

> <ALOGPS_LOGS>
-2.77

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
7.29353247768773

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.366609768744095

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6483954110345156

> <JCHEM_POLAR_SURFACE_AREA>
213.66999999999996

> <JCHEM_REFRACTIVITY>
118.2384

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
8.54e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5,7-dihydroxy-3-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2-(3,4,5-trihydroxyphenyl)-1lambda4-chromen-1-ylium

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 23-SEP-17   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: Delphinidin 3-O-galactoside                       
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-SEP-17         0                                  
HETATM    1  O   UNK     0      -2.667   6.160   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      -2.667   4.620   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      -1.334   2.310   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       5.335   1.540   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       8.002  -3.080   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       2.667  -3.080   0.000  0.00  0.00           O+1
HETATM   18  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      -1.334  -6.930   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      -2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      -4.001  -5.390   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      -2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      -4.001  -2.310   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       2.667   1.540   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       2.667   4.620   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       0.000   6.160   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   32                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   28                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   18                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   16                                                  
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15    9   17                                                  
CONECT   17   16   18                                                       
CONECT   18   17    7   19                                                  
CONECT   19   18   20   27                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   19                                                       
CONECT   28    5   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30    3   33                                                  
CONECT   33   32                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   72    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₁H₂₁O₁₂

Average Mass

465.3842 Da

Monoisotopic Mass

465.10330 Da

IUPAC Name

5,7-dihydroxy-3-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2-(3,4,5-trihydroxyphenyl)-1lambda4-chromen-1-ylium

Traditional Name

5,7-dihydroxy-3-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2-(3,4,5-trihydroxyphenyl)-1lambda4-chromen-1-ylium

CAS Registry Number

Not Available

SMILES

OCC1OC(OC2=CC3=C(O)C=C(O)C=C3[O+]=C2C2=CC(O)=C(O)C(O)=C2)C(O)C(O)C1O

InChI Identifier

InChI=1S/C21H20O12/c22-6-15-17(28)18(29)19(30)21(33-15)32-14-5-9-10(24)3-8(23)4-13(9)31-20(14)7-1-11(25)16(27)12(26)2-7/h1-5,15,17-19,21-22,28-30H,6H2,(H4-,23,24,25,26,27)/p+1

InChI Key

XENHPQQLDPAYIJ-UHFFFAOYSA-O

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Vaccinium corymbosum	LOTUS Database	35616633
Vaccinium myrtillus	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as diterpene glycosides. These are diterpenoids in which an isoprene unit is glycosylated.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene glycosides

Direct Parent

Diterpene glycosides

Alternative Parents

Substituents

Diterpene glycoside
Oligosaccharide
Diterpenoid
Fatty acyl glycoside
Glycosyl compound
O-glycosyl compound
Fatty acyl
Oxane
Carboxylic acid ester
Secondary alcohol
Acetal
Monocarboxylic acid or derivatives
Organoheterocyclic compound
Oxacycle
Carboxylic acid derivative
Polyol
Organooxygen compound
Alcohol
Hydrocarbon derivative
Organic oxygen compound
Organic oxide
Carbonyl group
Primary alcohol
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	0.93	ALOGPS
logP	0.1	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Acidic)	6.37	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	12	ChemAxon
Hydrogen Donor Count	9	ChemAxon
Polar Surface Area	213.67 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	118.24 m³·mol⁻¹	ChemAxon
Polarizability	43.56 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0130553

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB017202

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

13915667

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 5,7-dihydroxy-3-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2-(3,4,5-trihydroxyphenyl)-1λ⁴-chromen-1-ylium (NP0259827)

MOL for NP0259827 (5,7-dihydroxy-3-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2-(3,4,5-trihydroxyphenyl)-1λ⁴-chromen-1-ylium)

3D MOL for NP0259827 (5,7-dihydroxy-3-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2-(3,4,5-trihydroxyphenyl)-1λ⁴-chromen-1-ylium)

3D SDF for NP0259827 (5,7-dihydroxy-3-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2-(3,4,5-trihydroxyphenyl)-1λ⁴-chromen-1-ylium)

3D-SDF for NP0259827 (5,7-dihydroxy-3-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2-(3,4,5-trihydroxyphenyl)-1λ⁴-chromen-1-ylium)

PDB for NP0259827 (5,7-dihydroxy-3-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2-(3,4,5-trihydroxyphenyl)-1λ⁴-chromen-1-ylium)

3D PDB for NP0259827 (5,7-dihydroxy-3-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2-(3,4,5-trihydroxyphenyl)-1λ⁴-chromen-1-ylium)

SMILES for NP0259827 (5,7-dihydroxy-3-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2-(3,4,5-trihydroxyphenyl)-1λ⁴-chromen-1-ylium)

INCHI for NP0259827 (5,7-dihydroxy-3-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2-(3,4,5-trihydroxyphenyl)-1λ⁴-chromen-1-ylium)

Structure for NP0259827 (5,7-dihydroxy-3-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2-(3,4,5-trihydroxyphenyl)-1λ⁴-chromen-1-ylium)

3D Structure for NP0259827 (5,7-dihydroxy-3-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2-(3,4,5-trihydroxyphenyl)-1λ⁴-chromen-1-ylium)