NP-MRD: Showing NP-Card for 5,7-dihydroxy-2-(4-hydroxy-3-oxidophenyl)-3-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1λ⁴-chromen-1-ylium (NP0198707)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-04 17:12:01 UTC

Updated at

2022-09-04 17:12:01 UTC

NP-MRD ID

NP0198707

Secondary Accession Numbers

None

Natural Product Identification

Common Name

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

Description

Cyanidin 3-O-beta-D-glucoside betaine 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. 5,7-dihydroxy-2-(4-hydroxy-3-oxidophenyl)-3-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1λ⁴-chromen-1-ylium is found in Acer platanoides, Achillea crithmifolia, Ajuga reptans, Allium altaicum, Allium cepa, Allium sativum, Allium schoenoprasum, Amelanchier alnifolia, Amelanchier sanguinea, Aster tataricus, Berberis integerrima, Camellia polyodonta, Camellia sinensis, Cornus suecica, Cyclamen persicum, Dacrycarpus dacrydioides, Daucus carota, Dracula chimaera, Dyckia niederleinii, Echinacea purpurea, Erythrina fusca, Euphorbia tirucalli, Euterpe edulis, Fragaria ananassa, Geranium sylvaticum, Gossypium hirsutum, Helianthus annuus, Hibiscus syriacus, Keckiella cordifolia, Litchi chinensis, Lobelia chinensis, Malus sylvestris, Morus alba, Oenothera affinis, Oenothera odorata, Oxalis reclinata, Paeonia suffruticosa, Penstemon serrulatus, Petunia exserta, Petunia hybrida, Phalaris arundinacea, Phaseolus vulgaris, Phleum pratense, Aronia melanocarpa, Phragmites australis, Pistacia lentiscus, Pistia stratiotes, Podocarpus totara, Populus deltoides, Populus tremula, Prunus cerasus, Prunus domestica, Prunus persica, Prunus serotina, Punica granatum, Puya ferruginea, Rhaponticum scariosum, Rheum rhaponticum, Rhododendron simsii, Ribes nigrum, Rosa platyacantha, Rubus idaeus, Rubus phoenicolasius, Sambucus canadensis, Sambucus nigra, Secale cereale, Tradescantia pallida, Tricyrtis formosana, Vaccinium angustifolium, Vaccinium arboreum, Vaccinium corymbosum, Vaccinium macrocarpon, Vaccinium myrtillus, Vaccinium padifolium, Vaccinium uliginosum, Vaccinium vitis-idaea, Visnea mocanera, Vitis vinifera and Zea mays. Based on a literature review very few articles have been published on cyanidin 3-O-beta-D-glucoside betaine.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309042219122D          

 32 35  0  0  1  0            999 V2000
   -2.1434   -0.4125    0.0000 O   0  5  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
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   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 O   0  3  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
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   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
    2.8579   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   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
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -3.7125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4289   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.1250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0000   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -3.7125    0.0000 C   0  0  2  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
   -0.7145   -2.8875    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4289   -2.4750    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
   -0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  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  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
  7 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
  5 16  2  0  0  0  0
 16 17  1  0  0  0  0
 18 17  1  6  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  6  0  0  0
 21 22  1  0  0  0  0
 20 23  1  0  0  0  0
 23 24  1  1  0  0  0
 23 25  1  0  0  0  0
 25 26  1  6  0  0  0
 25 27  1  0  0  0  0
 18 27  1  0  0  0  0
 27 28  1  1  0  0  0
  4 29  2  0  0  0  0
 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
  2 31  1  0  0  0  0
 31 32  1  0  0  0  0
M  CHG  2   1  -1   6   1
M  END

     RDKit          3D

 52 55  0  0  0  0  0  0  0  0999 V2000
   -0.4350   -4.6871    1.8031 O   0  0  0  0  0  1  0  0  0  0  0  0
   -1.4841   -3.8175    1.6182 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2477   -2.5420    1.0808 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2453   -1.6433    0.8768 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1046   -0.3165    0.3335 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1972    0.4417    0.1981 O   0  0  0  0  0  3  0  0  0  0  0  0
   -3.2063    1.6451   -0.2743 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3906    2.3317   -0.3678 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4511    3.6174   -0.8649 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6541    4.3089   -0.9575 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3038    4.2083   -1.2688 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0663    3.5556   -1.1966 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9349    4.2010   -1.6196 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0405    2.2795   -0.6981 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8856    1.5768   -0.5939 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9311    0.2656   -0.0709 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2184   -0.4690    0.0466 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4712   -0.0905   -0.2898 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0898   -0.9301   -1.2193 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3820   -0.6551   -1.4955 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.1495   -1.9772   -1.5054 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5024   -1.7646   -1.7865 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0848    0.3448   -0.6812 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.2659    1.5504   -1.4020 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5310    0.6734    0.6474 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.4709    0.7042    1.6696 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3743   -0.2441    0.9588 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6439    0.1662    2.0684 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5332   -2.0779    1.2409 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8141   -3.2998    1.7638 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7561   -4.1720    1.9484 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0135   -5.4398    2.4859 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2426   -2.3120    0.8396 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3540    1.9065   -0.0566 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6674    5.2484   -1.3253 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2620    5.2246   -1.6751 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0333    3.8033   -1.5976 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0315    2.0071   -0.9002 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5718    0.9204   -0.7038 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4243   -0.3148   -2.5755 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9961   -2.5516   -0.5692 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7646   -2.6424   -2.3307 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0835   -1.8678   -1.0085 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1456   -0.0144   -0.5170 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6828    1.2774   -2.2650 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0839    1.7125    0.6316 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0344    1.1809    2.4353 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7654   -1.2656    1.0374 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9045    1.0541    2.3677 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3556   -1.3797    1.0895 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7911   -3.6410    2.0446 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2715   -6.0901    2.6305 H   0  0  0  0  0  0  0  0  0  0  0  0
 22 21  1  0
 21 20  1  0
 20 19  1  0
 19 18  1  0
 18 17  1  0
 17 16  1  0
 16  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
  9 11  2  0
 11 12  1  0
 12 13  1  0
 12 14  2  0
 14 15  1  0
  5  4  1  0
  4 29  2  0
 29 30  1  0
 30 31  2  0
 31 32  1  0
 31  2  1  0
  2  1  1  0
  2  3  2  0
 18 27  1  0
 27 28  1  0
 27 25  1  0
 25 26  1  0
 25 23  1  0
 23 24  1  0
 23 20  1  0
 15 16  2  0
  3  4  1  0
 14  7  1  0
 22 43  1  0
 21 41  1  0
 21 42  1  0
 20 40  1  6
 18 39  1  6
  8 34  1  0
 10 35  1  0
 11 36  1  0
 13 37  1  0
 15 38  1  0
 29 50  1  0
 30 51  1  0
 32 52  1  0
  3 33  1  0
 27 48  1  1
 28 49  1  0
 25 46  1  6
 26 47  1  0
 23 44  1  1
 24 45  1  0
M  CHG  2   1  -1   6   1
M  END


  Mrv1652309042219122D          

 32 35  0  0  1  0            999 V2000
   -2.1434   -0.4125    0.0000 O   0  5  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
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   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 O   0  3  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
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   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
    2.8579   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   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
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -3.7125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4289   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.1250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0000   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -3.7125    0.0000 C   0  0  2  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
   -0.7145   -2.8875    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4289   -2.4750    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
   -0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  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  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
  7 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
  5 16  2  0  0  0  0
 16 17  1  0  0  0  0
 18 17  1  6  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  6  0  0  0
 21 22  1  0  0  0  0
 20 23  1  0  0  0  0
 23 24  1  1  0  0  0
 23 25  1  0  0  0  0
 25 26  1  6  0  0  0
 25 27  1  0  0  0  0
 18 27  1  0  0  0  0
 27 28  1  1  0  0  0
  4 29  2  0  0  0  0
 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
  2 31  1  0  0  0  0
 31 32  1  0  0  0  0
M  CHG  2   1  -1   6   1
M  END
> <DATABASE_ID>
NP0198707

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C21H20O11/c22-7-16-17(27)18(28)19(29)21(32-16)31-15-6-10-12(25)4-9(23)5-14(10)30-20(15)8-1-2-11(24)13(26)3-8/h1-6,16-19,21-22,27-29H,7H2,(H3-,23,24,25,26)/t16-,17-,18+,19-,21-/m1/s1

> <INCHI_KEY>
RKWHWFONKJEUEF-GQUPQBGVSA-N

> <FORMULA>
C21H20O11

> <MOLECULAR_WEIGHT>
448.38

> <EXACT_MASS>
448.100561464

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_ATOM_COUNT>
52

> <JCHEM_AVERAGE_POLARIZABILITY>
42.46470267764702

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <JCHEM_LOGP>
0.38699999999999934

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
7.457961070975373

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.388329617449456

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9810923799280262

> <JCHEM_POLAR_SURFACE_AREA>
196.26999999999998

> <JCHEM_REFRACTIVITY>
126.80780000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

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

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-22         0                                  
HETATM    1  O   UNK     0      -4.001  -0.770   0.000  0.00  0.00           O-1
HETATM    2  C   UNK     0      -2.667   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       2.667   0.000   0.000  0.00  0.00           O+1
HETATM    7  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       8.002  -0.000   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       5.335  -4.620   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       0.000  -3.080   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       1.334  -5.390   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.667  -7.700   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       4.001  -6.930   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       0.000  -7.700   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       0.000  -9.240   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      -1.334  -6.930   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      -2.667  -7.700   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      -2.667  -4.620   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -2.667   1.540   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      -4.001   2.310   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   31                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   29                                                  
CONECT    5    4    6   16                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   14                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12    7   15                                                  
CONECT   15   14   16                                                       
CONECT   16   15    5   17                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   27                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21   23                                                  
CONECT   21   20   22                                                       
CONECT   22   21                                                            
CONECT   23   20   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   18   28                                                  
CONECT   28   27                                                            
CONECT   29    4   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30    2   32                                                  
CONECT   32   31                                                            
MASTER        0    0    0    0    0    0    0    0   32    0   70    0
END

View in JSmol

Synonyms

Value	Source
Cyanidin 3-O-b-D-glucoside betaine	Generator
Cyanidin 3-O-β-D-glucoside betaine	Generator

Chemical Formula

C₂₁H₂₀O₁₁

Average Mass

448.3800 Da

Monoisotopic Mass

448.10056 Da

IUPAC Name

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

Traditional Name

5,7-dihydroxy-2-(4-hydroxy-3-oxidophenyl)-3-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1lambda4-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=C(O)C([O-])=C2)[C@H](O)[C@@H](O)[C@@H]1O

InChI Identifier

InChI=1S/C21H20O11/c22-7-16-17(27)18(28)19(29)21(32-16)31-15-6-10-12(25)4-9(23)5-14(10)30-20(15)8-1-2-11(24)13(26)3-8/h1-6,16-19,21-22,27-29H,7H2,(H3-,23,24,25,26)/t16-,17-,18+,19-,21-/m1/s1

InChI Key

RKWHWFONKJEUEF-GQUPQBGVSA-N

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
Acer platanoides	LOTUS Database	35616633
Achillea crithmifolia	LOTUS Database	35616633
Ajuga reptans	LOTUS Database	35616633
Allium altaicum	LOTUS Database	35616633
Allium cepa	LOTUS Database	35616633
Allium sativum	LOTUS Database	35616633
Allium schoenoprasum	LOTUS Database	35616633
Amelanchier alnifolia	LOTUS Database	35616633
Amelanchier sanguinea	LOTUS Database	35616633
Aster tataricus	LOTUS Database	35616633
Berberis integerrima	LOTUS Database	35616633
Camellia polyodonta	LOTUS Database	35616633
Camellia sinensis	LOTUS Database	35616633
Cornus suecica	LOTUS Database	35616633
Cyclamen persicum	LOTUS Database	35616633
Dacrycarpus dacrydioides	LOTUS Database	35616633
Daucus carota	LOTUS Database	35616633
Dracula chimaera	LOTUS Database	35616633
Dyckia niederleinii	LOTUS Database	35616633
Echinacea purpurea	LOTUS Database	35616633
Erythrina fusca	LOTUS Database	35616633
Euphorbia tirucalli	LOTUS Database	35616633
Euterpe edulis	LOTUS Database	35616633
Fragaria x ananassa	LOTUS Database	35616633
Geranium sylvaticum	LOTUS Database	35616633
Gossypium hirsutum	LOTUS Database	35616633
Helianthus annuus	LOTUS Database	35616633
Hibiscus syriacus	LOTUS Database	35616633
Keckiella cordifolia	LOTUS Database	35616633
Litchi chinensis	LOTUS Database	35616633
Lobelia chinensis	LOTUS Database	35616633
Malus sylvestris	LOTUS Database	35616633
Morus alba	LOTUS Database	35616633
Oenothera affinis	LOTUS Database	35616633
Oenothera odorata	LOTUS Database	35616633
Oxalis reclinata	LOTUS Database	35616633
Paeonia suffruticosa	LOTUS Database	35616633
Penstemon serrulatus	LOTUS Database	35616633
Petunia exserta	LOTUS Database	35616633
Petunia hybrida	LOTUS Database	35616633
Phalaris arundinacea	LOTUS Database	35616633
Phaseolus vulgaris	LOTUS Database	35616633
Phleum pratense	LOTUS Database	35616633
Photinia melanocarpa	LOTUS Database	35616633
Phragmites australis	LOTUS Database	35616633
Pistacia lentiscus	LOTUS Database	35616633
Pistia stratiotes	LOTUS Database	35616633
Podocarpus totara	LOTUS Database	35616633
Populus deltoides	LOTUS Database	35616633
Populus tremula	LOTUS Database	35616633
Prunus cerasus	LOTUS Database	35616633
Prunus domestica	LOTUS Database	35616633
Prunus persica	LOTUS Database	35616633
Prunus serotina	LOTUS Database	35616633
Punica granatum	LOTUS Database	35616633
Puya ferruginea	LOTUS Database	35616633
Rhaponticum scariosum	LOTUS Database	35616633
Rheum rhaponticum	LOTUS Database	35616633
Rhododendron simsii	LOTUS Database	35616633
Ribes nigrum	LOTUS Database	35616633
Rosa platyacantha	LOTUS Database	35616633
Rubus idaeus	LOTUS Database	35616633
Rubus phoenicolasius	LOTUS Database	35616633
Sambucus canadensis	LOTUS Database	35616633
Sambucus nigra	LOTUS Database	35616633
Secale cereale	LOTUS Database	35616633
Tradescantia pallida	LOTUS Database	35616633
Tricyrtis formosana	LOTUS Database	35616633
Vaccinium angustifolium	LOTUS Database	35616633
Vaccinium arboreum	LOTUS Database	35616633
Vaccinium corymbosum	LOTUS Database	35616633
Vaccinium macrocarpon	LOTUS Database	35616633
Vaccinium myrtillus	LOTUS Database	35616633
Vaccinium padifolium	LOTUS Database	35616633
Vaccinium uliginosum	LOTUS Database	35616633
Vaccinium vitis-idaea	LOTUS Database	35616633
Visnea mocanera	LOTUS Database	35616633
Vitis vinifera	LOTUS Database	35616633
Zea mays	LOTUS Database	35616633

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
7-hydroxyflavonoid
Anthocyanidin
Hexose monosaccharide
Glycosyl compound
O-glycosyl compound
1-benzopyran
Benzopyran
Catechol
1-hydroxy-2-unsubstituted benzenoid
Phenol
1-hydroxy-4-unsubstituted benzenoid
Phenoxide
Monocyclic benzene moiety
Benzenoid
Monosaccharide
Oxane
Heteroaromatic compound
Secondary alcohol
Organoheterocyclic compound
Oxacycle
Polyol
Acetal
Primary alcohol
Organic zwitterion
Organic oxide
Organic oxygen compound
Alcohol
Hydrocarbon derivative
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

beta-D-glucoside (CHEBI:61318 )
oxonium betaine (CHEBI:61318 )

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	0.39	ChemAxon
pKa (Strongest Acidic)	6.39	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	196.27 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	126.81 m³·mol⁻¹	ChemAxon
Polarizability	42.46 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

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

26332196

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

61318

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 5,7-dihydroxy-2-(4-hydroxy-3-oxidophenyl)-3-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1λ⁴-chromen-1-ylium (NP0198707)

MOL for NP0198707 (5,7-dihydroxy-2-(4-hydroxy-3-oxidophenyl)-3-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1λ⁴-chromen-1-ylium)

3D MOL for NP0198707 (5,7-dihydroxy-2-(4-hydroxy-3-oxidophenyl)-3-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1λ⁴-chromen-1-ylium)

3D SDF for NP0198707 (5,7-dihydroxy-2-(4-hydroxy-3-oxidophenyl)-3-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1λ⁴-chromen-1-ylium)

3D-SDF for NP0198707 (5,7-dihydroxy-2-(4-hydroxy-3-oxidophenyl)-3-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1λ⁴-chromen-1-ylium)

PDB for NP0198707 (5,7-dihydroxy-2-(4-hydroxy-3-oxidophenyl)-3-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1λ⁴-chromen-1-ylium)

3D PDB for NP0198707 (5,7-dihydroxy-2-(4-hydroxy-3-oxidophenyl)-3-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1λ⁴-chromen-1-ylium)

SMILES for NP0198707 (5,7-dihydroxy-2-(4-hydroxy-3-oxidophenyl)-3-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1λ⁴-chromen-1-ylium)

INCHI for NP0198707 (5,7-dihydroxy-2-(4-hydroxy-3-oxidophenyl)-3-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1λ⁴-chromen-1-ylium)

Structure for NP0198707 (5,7-dihydroxy-2-(4-hydroxy-3-oxidophenyl)-3-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1λ⁴-chromen-1-ylium)

3D Structure for NP0198707 (5,7-dihydroxy-2-(4-hydroxy-3-oxidophenyl)-3-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1λ⁴-chromen-1-ylium)