NP-MRD: Showing NP-Card for Vicenin 2 (NP0045991)

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Record Information

Version

2.0

Created at

2022-03-17 19:46:36 UTC

Updated at

2022-03-17 19:46:36 UTC

NP-MRD ID

NP0045991

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Vicenin 2

Description

Vicenin 2 belongs to the class of organic compounds known as flavonoid 8-c-glycosides. Flavonoid 8-C-glycosides are compounds containing a carbohydrate moiety which is C-glycosidically linked to 8-position of a 2-phenylchromen-4-one flavonoid backbone. Vicenin 2 is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Vicenin 2 is found, on average, in the highest concentration within sweet oranges. Vicenin 2 has also been detected, but not quantified in, several different foods, such as cucumbers, flours, hard wheats, rices, and cereals and cereal products. Vicenin 2 is found in Acanthus ebracteatus, Acanthus ilicifolius, Aeluropus lagopoides, Anethum graveolens, Artemisia capillaris, Artemisia frigida, Artemisia herba-alba, Artemisia monosperma, Asplenium normale, Ballota foetida, Ballota hirsuta, Bombax ceiba, Bryum pseudotriquetrum, Camellia sinensis, Centaurea horrida, Centaurea melitensis L., Centaurea montana, Centaurea pseudomaculosa, Cerastium arvense, Cirsium oligophyllum, Citrus aurantiifolia, Citrus japonica, Citrus reticulata, Citrus unshiu , Craspedolobium schochii, Crataegus monogyna, Cucumis sativus, Cydonia oblonga , Carex fraseriana, Cyperus alopecuroides, Ephedra alata, Ephedra antisyphilitica, Ephedra aphylla, Euchresta horsfieldii, Eupatorium serotinum, Galipea trifoliata, Glinus lotoides, Glycyrrhiza aspera, Glycyrrhiza glabra , Glycyrrhiza inflata , Glycyrrhiza macedonica, Glycyrrhiza uralensis , Gnetum africanum, Gnetum gnemon, Gratiola officinalis, Haplopappus schumannii, Hebe parviflora, Hyparrhenia hirta, Japonolirion osense, Justicia ramosa, Lavandula dentata, Linum grandiflorum, Lychnophora ericoides, Lysimachia christinae, Dolichandra unguis-cati, Marrubium vulgare, Medicago truncatula, Meehania urticifolia, Mentha spicata, Glinus oppositifolius, Monachosorum henryi, Moringa oleifera , Moringa peregrine, Moringa stenopetala , Nervilia fordii, Ocimum gratissimum, Ocimum tenuiflorum, Oenothera triangulata, Origanum vulgare , Ostericum sieboldii, Parkinsonia aculeata, Passiflora foetida, Passiflora incarnata, Passiflora pittieri, Phlomis floccosa, Pistia stratiotes, Potentilla anserina, Primula spectabilis, Pyrrosia serpens, Retama raetam, Retama sphaerocarpa, Rhynchosia beddomei, Salvia fruticosa, Salvia lanigera, Salvia spinosa , Salvia triloba , Satureja cuneifolia, Scleropyrum pentandrum, Scoparia dulcis, Scorodocarpus borneensis, Scutellaria albida, Sechium edule, Senna alexandrina, Siphonoglossa buchii, Sophora spp., Spergularia rubra , Stachys aegyptiaca, Stachys officinalis (L.) Trev. , Stellaria dichotoma, Tecoma stans, Teucridium parvifolium, Teucrium leucocladum, Thunbergia laurifolia, Thymbra capitata, Thymus membranaceus, Tragopogon spp., Trichomanes bicorne, Trichomanes crispum, Trichophorum cespitosum, Tripora divaricata, Urtica circularis, Veronica strictissima, Vicia faba , Viola yedoensis, Viola tricolor , Vitex lucens, Wilbrandia ebracteata, Xanthosoma sagittifolium, Xanthosoma violaceum and Ziziphus jujuba. This could make vicenin 2 a potential biomarker for the consumption of these foods.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 05061305272D          

 42 46  0  0  0  0            999 V2000
   -2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    2.4750    0.0000 C   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
   -1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    3.7125    0.0000 C   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
   -3.5724    2.0625    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    0.8250    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
    1.4289    3.3000    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
    1.4289    0.0000    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
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    3.7125    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    0.8250    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
    0.0000    3.3000    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
    0.0000    2.4750    0.0000 C   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
    2.1434   -0.4125    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
    3.5724   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 O   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
    0.7145    4.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 O   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
    4.2868    0.0000    0.0000 O   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
    2.8579    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 O   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
    1.4289    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  1  0  0  0  0
  4  2  2  0  0  0  0
  8  1  2  0  0  0  0
  8  2  1  0  0  0  0
  9  3  2  0  0  0  0
  9  4  1  0  0  0  0
 10  5  1  0  0  0  0
 11  5  2  0  0  0  0
 11  8  1  0  0  0  0
 12  6  1  0  0  0  0
 13  7  1  0  0  0  0
 14 10  1  0  0  0  0
 17 12  1  0  0  0  0
 18 13  1  0  0  0  0
 19 14  2  0  0  0  0
 19 15  1  0  0  0  0
 20 15  2  0  0  0  0
 20 16  1  0  0  0  0
 21 17  1  0  0  0  0
 22 18  1  0  0  0  0
 23 21  1  0  0  0  0
 24 22  1  0  0  0  0
 25 14  1  0  0  0  0
 25 16  2  0  0  0  0
 26 15  1  0  0  0  0
 26 23  1  0  0  0  0
 27 16  1  0  0  0  0
 27 24  1  0  0  0  0
 28  6  1  0  0  0  0
 29  7  1  0  0  0  0
 30  9  1  0  0  0  0
 31 10  2  0  0  0  0
 32 17  1  0  0  0  0
 33 18  1  0  0  0  0
 34 19  1  0  0  0  0
 35 20  1  0  0  0  0
 36 21  1  0  0  0  0
 37 22  1  0  0  0  0
 38 23  1  0  0  0  0
 39 24  1  0  0  0  0
 40 11  1  0  0  0  0
 40 25  1  0  0  0  0
 41 12  1  0  0  0  0
 41 26  1  0  0  0  0
 42 13  1  0  0  0  0
 42 27  1  0  0  0  0
M  END


  Mrv0541 05061305272D          

 42 46  0  0  0  0            999 V2000
   -2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    2.4750    0.0000 C   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
   -1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    3.7125    0.0000 C   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
   -3.5724    2.0625    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    0.8250    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
    1.4289    3.3000    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
    1.4289    0.0000    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
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    3.7125    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    0.8250    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
    0.0000    3.3000    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
    0.0000    2.4750    0.0000 C   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
    2.1434   -0.4125    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
    3.5724   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 O   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
    0.7145    4.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 O   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
    4.2868    0.0000    0.0000 O   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
    2.8579    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 O   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
    1.4289    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  1  0  0  0  0
  4  2  2  0  0  0  0
  8  1  2  0  0  0  0
  8  2  1  0  0  0  0
  9  3  2  0  0  0  0
  9  4  1  0  0  0  0
 10  5  1  0  0  0  0
 11  5  2  0  0  0  0
 11  8  1  0  0  0  0
 12  6  1  0  0  0  0
 13  7  1  0  0  0  0
 14 10  1  0  0  0  0
 17 12  1  0  0  0  0
 18 13  1  0  0  0  0
 19 14  2  0  0  0  0
 19 15  1  0  0  0  0
 20 15  2  0  0  0  0
 20 16  1  0  0  0  0
 21 17  1  0  0  0  0
 22 18  1  0  0  0  0
 23 21  1  0  0  0  0
 24 22  1  0  0  0  0
 25 14  1  0  0  0  0
 25 16  2  0  0  0  0
 26 15  1  0  0  0  0
 26 23  1  0  0  0  0
 27 16  1  0  0  0  0
 27 24  1  0  0  0  0
 28  6  1  0  0  0  0
 29  7  1  0  0  0  0
 30  9  1  0  0  0  0
 31 10  2  0  0  0  0
 32 17  1  0  0  0  0
 33 18  1  0  0  0  0
 34 19  1  0  0  0  0
 35 20  1  0  0  0  0
 36 21  1  0  0  0  0
 37 22  1  0  0  0  0
 38 23  1  0  0  0  0
 39 24  1  0  0  0  0
 40 11  1  0  0  0  0
 40 25  1  0  0  0  0
 41 12  1  0  0  0  0
 41 26  1  0  0  0  0
 42 13  1  0  0  0  0
 42 27  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0045991

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OCC1OC(C(O)C(O)C1O)C1=C(O)C(C2OC(CO)C(O)C(O)C2O)=C2OC(=CC(=O)C2=C1O)C1=CC=C(O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C27H30O15/c28-6-12-17(32)21(36)23(38)26(41-12)15-19(34)14-10(31)5-11(8-1-3-9(30)4-2-8)40-25(14)16(20(15)35)27-24(39)22(37)18(33)13(7-29)42-27/h1-5,12-13,17-18,21-24,26-30,32-39H,6-7H2

> <INCHI_KEY>
FIAAVMJLAGNUKW-UHFFFAOYSA-N

> <FORMULA>
C27H30O15

> <MOLECULAR_WEIGHT>
594.5181

> <EXACT_MASS>
594.15847029

> <JCHEM_ACCEPTOR_COUNT>
15

> <JCHEM_AVERAGE_POLARIZABILITY>
57.5816809914175

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
11

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
5,7-dihydroxy-2-(4-hydroxyphenyl)-6,8-bis[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-4H-chromen-4-one

> <ALOGPS_LOGP>
-0.97

> <JCHEM_LOGP>
-2.8079526763333336

> <ALOGPS_LOGS>
-1.78

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
8.477498109060173

> <JCHEM_PKA_STRONGEST_ACIDIC>
5.763431124601631

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6447308976215727

> <JCHEM_POLAR_SURFACE_AREA>
267.28999999999996

> <JCHEM_REFRACTIVITY>
139.15049999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
9.88e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5,7-dihydroxy-2-(4-hydroxyphenyl)-6,8-bis[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]chromen-4-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0      -4.001   3.850   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -5.335   1.540   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -5.335   4.620   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -6.668   2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.667   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.001   6.930   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -4.001   2.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -6.668   3.850   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -2.667   1.540   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  C   UNK     0       2.667   6.160   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.667   0.000   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  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.334   6.930   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       0.000   6.160   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       6.668  -5.390   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0       5.335   6.160   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0      -8.002   4.620   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0      -1.334  -2.310   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0       8.002  -3.080   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0       1.334   8.470   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
HETATM   35  O   UNK     0       4.001   2.310   0.000  0.00  0.00           O+0
HETATM   36  O   UNK     0       8.002   0.000   0.000  0.00  0.00           O+0
HETATM   37  O   UNK     0      -1.334   6.930   0.000  0.00  0.00           O+0
HETATM   38  O   UNK     0       5.335   1.540   0.000  0.00  0.00           O+0
HETATM   39  O   UNK     0      -1.334   3.850   0.000  0.00  0.00           O+0
HETATM   40  O   UNK     0      -1.334   2.310   0.000  0.00  0.00           O+0
HETATM   41  O   UNK     0       4.001  -2.310   0.000  0.00  0.00           O+0
HETATM   42  O   UNK     0       2.667   4.620   0.000  0.00  0.00           O+0
CONECT    1    3    8                                                       
CONECT    2    4    8                                                       
CONECT    3    1    9                                                       
CONECT    4    2    9                                                       
CONECT    5   10   11                                                       
CONECT    6   12   28                                                       
CONECT    7   13   29                                                       
CONECT    8    1    2   11                                                  
CONECT    9    3    4   30                                                  
CONECT   10    5   14   31                                                  
CONECT   11    5    8   40                                                  
CONECT   12    6   17   41                                                  
CONECT   13    7   18   42                                                  
CONECT   14   10   19   25                                                  
CONECT   15   19   20   26                                                  
CONECT   16   20   25   27                                                  
CONECT   17   12   21   32                                                  
CONECT   18   13   22   33                                                  
CONECT   19   14   15   34                                                  
CONECT   20   15   16   35                                                  
CONECT   21   17   23   36                                                  
CONECT   22   18   24   37                                                  
CONECT   23   21   26   38                                                  
CONECT   24   22   27   39                                                  
CONECT   25   14   16   40                                                  
CONECT   26   15   23   41                                                  
CONECT   27   16   24   42                                                  
CONECT   28    6                                                            
CONECT   29    7                                                            
CONECT   30    9                                                            
CONECT   31   10                                                            
CONECT   32   17                                                            
CONECT   33   18                                                            
CONECT   34   19                                                            
CONECT   35   20                                                            
CONECT   36   21                                                            
CONECT   37   22                                                            
CONECT   38   23                                                            
CONECT   39   24                                                            
CONECT   40   11   25                                                       
CONECT   41   12   26                                                       
CONECT   42   13   27                                                       
MASTER        0    0    0    0    0    0    0    0   42    0   92    0
END

View in JSmol

Synonyms

Value	Source
5,7,4'-Trihydroxyflavone-6,8-di-C-glucoside	HMDB
6,8-Di-b-D-glucopyranosyl-5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one, 9ci	HMDB
6,8-Di-C-glucopyranosylapigenin	HMDB
6,8-Di-C-glucosyl-4',5,7-trihydroxyflavone	HMDB
6,8-Di-C-glucosylapigenin	HMDB
Apigenin 6,8-di-C-glucoside	HMDB
Vicenin-2	HMDB
Vicenin-1	MeSH
6-C-beta-D-Xylopyranosyl-8-C-beta-D-glucopyranosyl apigenin	MeSH
Vicenin	MeSH

Chemical Formula

C₂₇H₃₀O₁₅

Average Mass

594.5181 Da

Monoisotopic Mass

594.15847 Da

IUPAC Name

5,7-dihydroxy-2-(4-hydroxyphenyl)-6,8-bis[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-4H-chromen-4-one

Traditional Name

5,7-dihydroxy-2-(4-hydroxyphenyl)-6,8-bis[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]chromen-4-one

CAS Registry Number

23666-13-9

SMILES

OCC1OC(C(O)C(O)C1O)C1=C(O)C(C2OC(CO)C(O)C(O)C2O)=C2OC(=CC(=O)C2=C1O)C1=CC=C(O)C=C1

InChI Identifier

InChI=1S/C27H30O15/c28-6-12-17(32)21(36)23(38)26(41-12)15-19(34)14-10(31)5-11(8-1-3-9(30)4-2-8)40-25(14)16(20(15)35)27-24(39)22(37)18(33)13(7-29)42-27/h1-5,12-13,17-18,21-24,26-30,32-39H,6-7H2

InChI Key

FIAAVMJLAGNUKW-UHFFFAOYSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Acanthus ebracteatus	LOTUS Database	35616633
Acanthus ilicifolius	LOTUS Database	35616633
Aeluropus lagopoides	LOTUS Database	35616633
Anethum graveolens	LOTUS Database	35616633
Artemisia capillaris	LOTUS Database	35616633
Artemisia frigida	LOTUS Database	35616633
Artemisia herba-alba	LOTUS Database	35616633
Artemisia monosperma	LOTUS Database	35616633
Asplenium normale	LOTUS Database	35616633
Avena sativa L.	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Ballota foetida	Plant	KNApSAcK
Ballota hirsuta	LOTUS Database	35616633
Bombax ceiba	LOTUS Database	35616633
Bryum pseudotriquetrum	LOTUS Database	35616633
Camellia sinensis	LOTUS Database	35616633
Centaurea horrida	LOTUS Database	35616633
Centaurea melitensis L.	Plant	KNApSAcK
Centaurea montana	LOTUS Database	35616633
Centaurea pseudomaculosa	LOTUS Database	35616633
Cerastium arvense	Plant	KNApSAcK
Cirsium oligophyllum	Plant	KNApSAcK
Citrus aurantiifolia	LOTUS Database	35616633
Citrus japonica	LOTUS Database	35616633
Citrus limon	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Citrus reticulata	LOTUS Database	35616633
Citrus unshiu	Plant	KNApSAcK
Citrus X sinensis (L.) Osbeck (pro. sp.)	FooDB	PHENOL EXPLORER
Craspedolobium schochii	LOTUS Database	35616633
Crataegus monogyna	LOTUS Database	35616633
Cucumis sativus	LOTUS Database	35616633
Cucumis sativus L.	FooDB	KNAPSACK
Cydonia oblonga	Plant	KNApSAcK
Cymophyllus fraseri	LOTUS Database	35616633
Cyperus alopecuroides	Plant	KNApSAcK
Ephedra alata	LOTUS Database	35616633
Ephedra antisyphilitica	LOTUS Database	35616633
Ephedra aphylla	Plant	KNApSAcK
Euchresta horsfieldii	LOTUS Database	35616633
Eupatorium serotinum	Plant	KNApSAcK
Galipea trifoliata	LOTUS Database	35616633
Glinus lotoides	LOTUS Database	35616633
Glycyrrhiza aspera	LOTUS Database	35616633
Glycyrrhiza glabra	Plant	KNApSAcK
Glycyrrhiza inflata	Plant	KNApSAcK
Glycyrrhiza macedonica	LOTUS Database	35616633
Glycyrrhiza uralensis	Plant	KNApSAcK
Gnetum africanum	LOTUS Database	35616633
Gnetum gnemon	LOTUS Database	35616633
Gratiola officinalis	LOTUS Database	35616633
Haplopappus schumannii	LOTUS Database	35616633
Hebe parviflora	Plant	KNApSAcK
Hyparrhenia hirta	LOTUS Database	35616633
Japonolirion osense	Plant	KNApSAcK
Justicia ramosa	LOTUS Database	35616633
Lavandula dentata	LOTUS Database	35616633
Linum grandiflorum	LOTUS Database	35616633
Linum usitatissimum	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Lychnophora ericoides	LOTUS Database	35616633
Lysimachia christinae	LOTUS Database	35616633
Macfadyena unguis-cati	LOTUS Database	35616633
Marrubium vulgare	LOTUS Database	35616633
Medicago truncatula	Plant	KNApSAcK
Meehania urticifolia	Plant	KNApSAcK
Mentha spicata	LOTUS Database	35616633
Mollugo oppositifolia	LOTUS Database	35616633
Monachosorum henryi	LOTUS Database	35616633
Moringa oleifera	Plant	KNApSAcK
Moringa peregrina	Plant	KNApSAcK
Moringa stenopetala	Plant	KNApSAcK
Nervilia fordii	LOTUS Database	35616633
Ocimum basilicum	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Ocimum gratissimum	LOTUS Database	35616633
Ocimum tenuiflorum	LOTUS Database	35616633
Oenothera triangulata	LOTUS Database	35616633
Origanum vulgare	Plant	KNApSAcK
Ostericum sieboldii	LOTUS Database	35616633
Parkinsonia aculeata	LOTUS Database	35616633
Passiflora foetida	LOTUS Database	35616633
Passiflora incarnata	LOTUS Database	35616633
Passiflora pittieri	LOTUS Database	35616633
Phlomis floccosa	LOTUS Database	35616633
Pistia stratiotes	LOTUS Database	35616633
Potentilla anserina	LOTUS Database	35616633
Primula spectabilis	LOTUS Database	35616633
Pyrrosia serpens	LOTUS Database	35616633
Retama raetam	LOTUS Database	35616633
Retama sphaerocarpa	LOTUS Database	35616633
Rhynchosia beddomei	LOTUS Database	35616633
Salvia fruticosa	LOTUS Database	35616633
Salvia lanigera	Plant	KNApSAcK
Salvia officinalis	FooDB	KNAPSACK
Salvia spinosa	Plant	KNApSAcK
Salvia triloba	Plant	KNApSAcK
Satureja cuneifolia	LOTUS Database	35616633
Scleropyrum pentandrum	LOTUS Database	35616633
Scoparia dulcis	LOTUS Database	35616633
Scorodocarpus borneensis	LOTUS Database	35616633
Scutellaria albida	LOTUS Database	35616633
Sechium edule	LOTUS Database	35616633
Senna alexandrina	LOTUS Database	35616633
Siphonoglossa buchii	Plant	KNApSAcK
Sophora spp.	Plant	KNApSAcK
Spergularia rubra	Plant	KNApSAcK
Stachys aegyptiaca	LOTUS Database	35616633
Stachys officinalis (L.) Trev.	Plant	KNApSAcK
Stellaria dichotoma	Plant	KNApSAcK
Tecoma stans	LOTUS Database	35616633
Teucridium parvifolium	Plant	KNApSAcK
Teucrium leucocladum	LOTUS Database	35616633
Thunbergia laurifolia	LOTUS Database	35616633
Thymbra capitata	LOTUS Database	35616633
Thymus membranaceus	Plant	KNApSAcK
Tragopogon porrifolius	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Tragopogon spp.	Plant	KNApSAcK
Trichomanes bicorne	LOTUS Database	35616633
Trichomanes crispum	LOTUS Database	35616633
Trichophorum cespitosum	LOTUS Database	35616633
Trigonella foenum-graecum	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Tripora divaricata	Plant	KNApSAcK
Triticum aestivum	FooDB	KNAPSACK
Urtica circularis	LOTUS Database	35616633
Veronica strictissima	LOTUS Database	35616633
Vicia faba	Plant	KNApSAcK
Viola philippica	Plant	KNApSAcK
Viola tricolor	Plant	KNApSAcK
Vitex lucens	Plant	KNApSAcK
Wilbrandia ebracteata	LOTUS Database	35616633
Xanthosoma sagittifolium	LOTUS Database	35616633
Xanthosoma violaceum	LOTUS Database	35616633
Ziziphus jujuba	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as flavonoid 8-c-glycosides. Flavonoid 8-C-glycosides are compounds containing a carbohydrate moiety which is C-glycosidically linked to 8-position of a 2-phenylchromen-4-one flavonoid backbone.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavonoid glycosides

Direct Parent

Flavonoid 8-C-glycosides

Alternative Parents

Substituents

Flavonoid-8-c-glycoside
Hydroxyflavonoid
4'-hydroxyflavonoid
5-hydroxyflavonoid
7-hydroxyflavonoid
Flavone
Phenolic glycoside
Hexose monosaccharide
Glycosyl compound
C-glycosyl compound
Chromone
1-benzopyran
Benzopyran
Pyranone
Phenol
1-hydroxy-2-unsubstituted benzenoid
Pyran
Monosaccharide
Monocyclic benzene moiety
Benzenoid
Oxane
Heteroaromatic compound
Vinylogous acid
Secondary alcohol
Ether
Dialkyl ether
Organoheterocyclic compound
Oxacycle
Polyol
Primary alcohol
Organic oxide
Organic oxygen compound
Alcohol
Hydrocarbon derivative
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic 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	-0.97	ALOGPS
logP	-2.8	ChemAxon
logS	-1.8	ALOGPS
pKa (Strongest Acidic)	5.76	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	15	ChemAxon
Hydrogen Donor Count	11	ChemAxon
Polar Surface Area	267.29 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	139.15 m³·mol⁻¹	ChemAxon
Polarizability	57.58 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0030708

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB 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

3084407

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Vicenin 2 (NP0045991)

MOL for NP0045991 (Vicenin 2)

3D MOL for NP0045991 (Vicenin 2)

3D SDF for NP0045991 (Vicenin 2)

3D-SDF for NP0045991 (Vicenin 2)

PDB for NP0045991 (Vicenin 2)

3D PDB for NP0045991 (Vicenin 2)

SMILES for NP0045991 (Vicenin 2)

INCHI for NP0045991 (Vicenin 2)

Structure for NP0045991 (Vicenin 2)

3D Structure for NP0045991 (Vicenin 2)