NP-MRD: Showing NP-Card for taxifolin 7-glucoside (NP0233425)

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Record Information

Version

2.0

Created at

2022-09-06 15:01:23 UTC

Updated at

2022-09-06 15:01:24 UTC

NP-MRD ID

NP0233425

Secondary Accession Numbers

None

Natural Product Identification

Common Name

taxifolin 7-glucoside

Description

Taxifolin 7-glucoside belongs to the class of organic compounds known as flavonoid-7-o-glycosides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to carbohydrate moiety at the C7-position. taxifolin 7-glucoside is found in Allium cepa, Coleogyne ramosissima, Cuscuta reflexa, Pelargonium reniforme, Picea abies, Pinus sylvestris, Podocarpus nivalis, Pseudotsuga menziesii and Sorghum bicolor. It was first documented in 2005 (PMID: 15713001). Based on a literature review a small amount of articles have been published on Taxifolin 7-glucoside (PMID: 29495517) (PMID: 21341175) (PMID: 17997520) (PMID: 17411068).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309062217012D          

 33 36  0  0  1  0            999 V2000
    1.4289    0.8250    0.0000 O   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   -1.2375    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
    5.0013   -1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -0.0000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.7158    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.1447   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.1447   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -1.6500    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.7158   -2.4750    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   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  2  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   -2.4750    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
   -1.4289   -2.4750    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   -1.2375    0.0000 O   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
    0.7145   -0.4125    0.0000 C   0  0  1  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
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  4  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  9  8  1  6  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  6  0  0  0
 12 13  1  0  0  0  0
 11 14  1  0  0  0  0
 14 15  1  1  0  0  0
 14 16  1  0  0  0  0
 16 17  1  6  0  0  0
 16 18  1  0  0  0  0
  9 18  1  0  0  0  0
 18 19  1  1  0  0  0
  7 20  1  0  0  0  0
 20 21  2  0  0  0  0
  3 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  6  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 27 28  1  0  0  0  0
 27 29  1  0  0  0  0
 29 30  1  0  0  0  0
 29 31  2  0  0  0  0
 24 31  1  0  0  0  0
 23 32  1  0  0  0  0
  2 32  1  0  0  0  0
 32 33  1  1  0  0  0
M  END

     RDKit          3D

 55 58  0  0  0  0  0  0  0  0999 V2000
    2.7846   -3.6894    1.5867 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5417   -2.7320    0.8314 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1865   -2.2083    0.6798 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0825   -2.9755    0.9659 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1521   -4.2750    1.3912 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1766   -2.3844    0.8078 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3193   -1.0733    0.3782 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5849   -0.5698    0.2494 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9877    0.7006   -0.1590 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.6804    1.3896    0.8242 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9351    1.8002    0.4695 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.5542    2.4641    1.6973 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6360    1.5894    2.7603 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7455    0.5849    0.0710 C   0  0  1  0  0  0  0  0  0  0  0  0
   -7.1032    0.9358   -0.1030 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1664    0.1208   -1.2719 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.3605   -1.2312   -1.4607 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7573    0.5739   -1.4459 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.6162    1.7394   -2.1760 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1750   -0.3587    0.1075 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1057   -0.8807    0.2423 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2298   -0.1207   -0.0440 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4827   -0.5793    0.4055 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.6074    0.2143   -0.0785 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7034    0.6143   -1.3901 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7883    1.3758   -1.8414 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7860    1.7322   -0.9415 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8442    2.4879   -1.4312 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7004    1.3390    0.3677 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7182    1.7166    1.2325 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6072    0.5789    0.7951 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5935   -2.0502    0.0336 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.8545   -2.5517    0.2578 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9659   -4.7921    1.5205 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0629   -2.9777    1.0305 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0966    1.3113   -0.3879 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9197    2.4934   -0.3898 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0117    3.3661    1.9892 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5981    2.7714    1.4163 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4533    1.0175    2.7304 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6321   -0.2412    0.7885 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6431    0.1306    0.1070 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7895    0.6485   -2.0484 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3508   -1.4210   -2.4503 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2294   -0.2279   -2.0423 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6402    1.8907   -2.2871 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2281    0.6732   -0.2327 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4217   -0.5689    1.5330 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9634    0.3644   -2.1128 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8720    1.6948   -2.8714 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.6151    2.7967   -0.8637 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6364    1.4162    2.1953 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6099    0.3057    1.8458 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3443   -2.0951   -1.0648 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2563   -2.8337   -0.6090 H   0  0  0  0  0  0  0  0  0  0  0  0
 13 12  1  0
 12 11  1  0
 11 10  1  0
 10  9  1  0
  9  8  1  0
  8  7  1  0
  7  6  2  0
  6  4  1  0
  4  5  1  0
  4  3  2  0
  3  2  1  0
  2  1  2  0
  2 32  1  0
 32 33  1  0
 32 23  1  0
 23 22  1  0
 22 21  1  0
 21 20  2  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 27 29  1  0
 29 30  1  0
 29 31  2  0
  9 18  1  0
 18 19  1  0
 18 16  1  0
 16 17  1  0
 16 14  1  0
 14 15  1  0
 14 11  1  0
 20  7  1  0
 31 24  1  0
 21  3  1  0
 13 40  1  0
 12 38  1  0
 12 39  1  0
 11 37  1  6
  9 36  1  6
  6 35  1  0
  5 34  1  0
 32 54  1  6
 33 55  1  0
 23 48  1  1
 20 47  1  0
 25 49  1  0
 26 50  1  0
 28 51  1  0
 30 52  1  0
 31 53  1  0
 18 45  1  6
 19 46  1  0
 16 43  1  6
 17 44  1  0
 14 41  1  1
 15 42  1  0
M  END


  Mrv1652309062217012D          

 33 36  0  0  1  0            999 V2000
    1.4289    0.8250    0.0000 O   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   -1.2375    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
    5.0013   -1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -0.0000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.7158    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.1447   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.1447   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -1.6500    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.7158   -2.4750    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   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  2  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   -2.4750    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
   -1.4289   -2.4750    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   -1.2375    0.0000 O   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
    0.7145   -0.4125    0.0000 C   0  0  1  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
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  4  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  9  8  1  6  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  6  0  0  0
 12 13  1  0  0  0  0
 11 14  1  0  0  0  0
 14 15  1  1  0  0  0
 14 16  1  0  0  0  0
 16 17  1  6  0  0  0
 16 18  1  0  0  0  0
  9 18  1  0  0  0  0
 18 19  1  1  0  0  0
  7 20  1  0  0  0  0
 20 21  2  0  0  0  0
  3 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  6  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 27 28  1  0  0  0  0
 27 29  1  0  0  0  0
 29 30  1  0  0  0  0
 29 31  2  0  0  0  0
 24 31  1  0  0  0  0
 23 32  1  0  0  0  0
  2 32  1  0  0  0  0
 32 33  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0233425

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC[C@H]1O[C@@H](OC2=CC(O)=C3C(=O)[C@H](O)[C@H](OC3=C2)C2=CC=C(O)C(O)=C2)[C@H](O)[C@@H](O)[C@@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C21H22O12/c22-6-13-15(26)17(28)19(30)21(33-13)31-8-4-11(25)14-12(5-8)32-20(18(29)16(14)27)7-1-2-9(23)10(24)3-7/h1-5,13,15,17-26,28-30H,6H2/t13-,15-,17+,18+,19-,20-,21-/m1/s1

> <INCHI_KEY>
BJAHHJOBSKZTFE-JUIPTLLLSA-N

> <FORMULA>
C21H22O12

> <MOLECULAR_WEIGHT>
466.395

> <EXACT_MASS>
466.111126148

> <JCHEM_ACCEPTOR_COUNT>
12

> <JCHEM_ATOM_COUNT>
55

> <JCHEM_AVERAGE_POLARIZABILITY>
43.871751272230654

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
8

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R,3R)-2-(3,4-dihydroxyphenyl)-3,5-dihydroxy-7-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,4-dihydro-2H-1-benzopyran-4-one

> <JCHEM_LOGP>
-0.45168382533333346

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.285823702779366

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.43352050437835

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9810923437586574

> <JCHEM_POLAR_SURFACE_AREA>
206.59999999999997

> <JCHEM_REFRACTIVITY>
106.75329999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(2R,3R)-2-(3,4-dihydroxyphenyl)-3,5-dihydroxy-7-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2,3-dihydro-1-benzopyran-4-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-SEP-22         0                                  
HETATM    1  O   UNK     0       2.667   1.540   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       5.335   1.540   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       8.002  -3.080   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       9.336  -2.310   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       9.336  -0.770   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      10.669  -0.000   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      10.669   1.540   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      12.003   2.310   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      12.003  -0.770   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      13.337  -0.000   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      12.003  -2.310   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      13.337  -3.080   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      10.669  -3.080   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      10.669  -4.620   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       2.667  -3.080   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      -4.001  -5.390   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      -2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      -4.001  -2.310   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       0.000  -0.000   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   32                                                  
CONECT    3    2    4   21                                                  
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6    8   20                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   18                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   14                                                  
CONECT   12   11   13                                                       
CONECT   13   12                                                            
CONECT   14   11   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16    9   19                                                  
CONECT   19   18                                                            
CONECT   20    7   21                                                       
CONECT   21   20    3   22                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24   32                                                  
CONECT   24   23   25   31                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   24                                                       
CONECT   32   23    2   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

C₂₁H₂₂O₁₂

Average Mass

466.3950 Da

Monoisotopic Mass

466.11113 Da

IUPAC Name

(2R,3R)-2-(3,4-dihydroxyphenyl)-3,5-dihydroxy-7-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,4-dihydro-2H-1-benzopyran-4-one

Traditional Name

(2R,3R)-2-(3,4-dihydroxyphenyl)-3,5-dihydroxy-7-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2,3-dihydro-1-benzopyran-4-one

CAS Registry Number

Not Available

SMILES

OC[C@H]1O[C@@H](OC2=CC(O)=C3C(=O)[C@H](O)[C@H](OC3=C2)C2=CC=C(O)C(O)=C2)[C@H](O)[C@@H](O)[C@@H]1O

InChI Identifier

InChI=1S/C21H22O12/c22-6-13-15(26)17(28)19(30)21(33-13)31-8-4-11(25)14-12(5-8)32-20(18(29)16(14)27)7-1-2-9(23)10(24)3-7/h1-5,13,15,17-26,28-30H,6H2/t13-,15-,17+,18+,19-,20-,21-/m1/s1

InChI Key

BJAHHJOBSKZTFE-JUIPTLLLSA-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
Allium cepa	LOTUS Database	35616633
Coleogyne ramosissima	LOTUS Database	35616633
Cuscuta reflexa	LOTUS Database	35616633
Pelargonium reniforme	LOTUS Database	35616633
Picea abies	LOTUS Database	35616633
Pinus sylvestris	LOTUS Database	35616633
Podocarpus nivalis	LOTUS Database	35616633
Pseudotsuga menziesii	LOTUS Database	35616633
Sorghum bicolor	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as flavonoid-7-o-glycosides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to carbohydrate moiety at the C7-position.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavonoid glycosides

Direct Parent

Flavonoid-7-O-glycosides

Alternative Parents

Substituents

Flavonoid-7-o-glycoside
3'-hydroxyflavonoid
3-hydroxyflavonoid
4'-hydroxyflavonoid
5-hydroxyflavonoid
Hydroxyflavonoid
Flavanonol
Flavanone
Flavan
Phenolic glycoside
Fatty acyl glycoside of mono- or disaccharide
Fatty acyl glycoside
Alkyl glycoside
Hexose monosaccharide
Glycosyl compound
Chromone
O-glycosyl compound
Benzopyran
Chromane
1-benzopyran
Catechol
Aryl alkyl ketone
Aryl ketone
Alkyl aryl ether
Phenol
1-hydroxy-2-unsubstituted benzenoid
1-hydroxy-4-unsubstituted benzenoid
Monocyclic benzene moiety
Oxane
Fatty acyl
Benzenoid
Monosaccharide
Vinylogous acid
Ketone
Secondary alcohol
Organoheterocyclic compound
Oxacycle
Polyol
Acetal
Ether
Organooxygen compound
Hydrocarbon derivative
Aldehyde
Alcohol
Organic oxide
Organic oxygen compound
Primary alcohol
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	-0.45	ChemAxon
pKa (Strongest Acidic)	8.43	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	12	ChemAxon
Hydrogen Donor Count	8	ChemAxon
Polar Surface Area	206.6 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	106.75 m³·mol⁻¹	ChemAxon
Polarizability	43.87 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	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00008709

Chemspider ID

32698210

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

14282775

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Corea G, Fattorusso E, Lanzotti V, Capasso R, Izzo AA: Antispasmodic saponins from bulbs of red onion, Allium cepa L. var. Tropea. J Agric Food Chem. 2005 Feb 23;53(4):935-40. doi: 10.1021/jf048404o. [PubMed:15713001 ]
Peixoto H, Roxo M, Koolen H, da Silva F, Silva E, Braun MS, Wang X, Wink M: Calycophyllum spruceanum (Benth.), the Amazonian "Tree of Youth" Prolongs Longevity and Enhances Stress Resistance in Caenorhabditis elegans. Molecules. 2018 Feb 27;23(3):534. doi: 10.3390/molecules23030534. [PubMed:29495517 ]
Hamalainen M, Nieminen R, Asmawi MZ, Vuorela P, Vapaatalo H, Moilanen E: Effects of flavonoids on prostaglandin E2 production and on COX-2 and mPGES-1 expressions in activated macrophages. Planta Med. 2011 Sep;77(13):1504-11. doi: 10.1055/s-0030-1270762. Epub 2011 Feb 21. [PubMed:21341175 ]
Slimestad R, Fossen T, Vagen IM: Onions: a source of unique dietary flavonoids. J Agric Food Chem. 2007 Dec 12;55(25):10067-80. doi: 10.1021/jf0712503. Epub 2007 Nov 13. [PubMed:17997520 ]
Japon-Lujan R, Luque de Castro MD: Static-dynamic superheated liquid extraction of hydroxytyrosol and other biophenols from alperujo (a semisolid residue of the olive oil industry). J Agric Food Chem. 2007 May 2;55(9):3629-34. doi: 10.1021/jf0636770. Epub 2007 Apr 6. [PubMed:17411068 ]
LOTUS database [Link]

Showing NP-Card for taxifolin 7-glucoside (NP0233425)

MOL for NP0233425 (taxifolin 7-glucoside)

3D MOL for NP0233425 (taxifolin 7-glucoside)

3D SDF for NP0233425 (taxifolin 7-glucoside)

3D-SDF for NP0233425 (taxifolin 7-glucoside)

PDB for NP0233425 (taxifolin 7-glucoside)

3D PDB for NP0233425 (taxifolin 7-glucoside)

SMILES for NP0233425 (taxifolin 7-glucoside)

INCHI for NP0233425 (taxifolin 7-glucoside)

Structure for NP0233425 (taxifolin 7-glucoside)

3D Structure for NP0233425 (taxifolin 7-glucoside)