NP-MRD: Showing NP-Card for quercetin-3-glucoside (NP0247409)

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Record Information

Version

2.0

Created at

2022-09-07 09:15:28 UTC

Updated at

2022-09-07 09:15:28 UTC

NP-MRD ID

NP0247409

Secondary Accession Numbers

None

Natural Product Identification

Common Name

quercetin-3-glucoside

Description

Quercetin 3-O-glucoside, also known as isoquercitrin or isotrifoliin, belongs to the class of organic compounds known as flavonoid-3-o-glycosides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to carbohydrate moiety at the C3-position. Quercetin 3-O-glucoside is an extremely weak basic (essentially neutral) compound (based on its pKa). Quercetin 3-O-glucoside may be a unique S. quercetin-3-glucoside is found in Sorbus aria, Astragalus bornmuellerianus, Camellia japonica, Camellia sinensis, Caragana spinosa, Dysphania botrys, Globularia bisnagarica, Hypericum brasiliense, Hypericum elegans, Hypericum perforatum, Lagerstroemia speciosa, Lonicera japonica, Marrubium velutinum, Matteuccia struthiopteris, Nelumbo nucifera, Phaseolus vulgaris, Phoenix loureiroi, Phyllanthus virgatus, Fallopia sachalinensis, Potentilla anserina, Salix caprea, Trifolium repens, Tripodanthus acutifolius, Viburnum tinus, Vicia sativa, Volutaria lippii and Warburgia ugandensis. Cerevisiae (yeast) metabolite.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 02241223252D          

 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
    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  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   -2.4750    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  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
    0.0000    0.8250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6674    1.3099    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4125    2.0945    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8974    2.7620    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7179    2.6757    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5619    3.5157    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0468    4.1831    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125    2.0945    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8974    2.7620    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6674    1.3099    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4521    1.0550    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
  7  9  1  0  0  0  0
  9 10  2  0  0  0  0
  3 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  2  0  0  0  0
 13 20  1  0  0  0  0
 12 21  2  0  0  0  0
  2 21  1  0  0  0  0
 21 22  1  0  0  0  0
 23 22  1  1  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  1  0  0  0
 26 27  1  1  0  0  0
 26 28  1  0  0  0  0
 28 29  1  0  0  0  0
 25 30  1  0  0  0  0
 30 31  1  1  0  0  0
 30 32  1  0  0  0  0
 23 32  1  0  0  0  0
 32 33  1  6  0  0  0
M  END

     RDKit          3D

 53 56  0  0  0  0  0  0  0  0999 V2000
    0.2702   -1.1924    2.3545 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7309   -1.0834    1.5886 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8923    0.0525    0.7753 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1317    0.9860    0.8965 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2704    0.7787    0.0615 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3114    0.1892    0.8230 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3974    0.4319   -0.0221 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.7029    0.0001    0.5781 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.7050    0.2884   -0.3446 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7000   -1.4931    0.7819 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7274   -1.8483    1.6874 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3119    1.9334   -0.1516 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5452    2.5803    1.0556 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8049    2.0795   -0.4170 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6937    2.2122   -1.8188 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9793    0.1160   -0.0184 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2506    1.2311   -0.8916 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6182    2.4239   -0.8002 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8952    3.4398   -1.7169 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8093    3.2579   -2.7253 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0433    4.2995   -3.6044 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4647    2.0628   -2.8408 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4010    1.7928   -3.8249 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1632    1.0711   -1.9093 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8760   -0.8911   -0.0249 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7666   -1.9534    0.7046 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7146   -2.9794    0.6741 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5174   -4.0752    1.4859 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4314   -5.1391    1.5023 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4261   -4.1910    2.3189 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4902   -3.1936    2.3586 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3628   -3.2450    3.1772 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6768   -2.0776    1.5417 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0848    0.0269   -0.7287 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2267   -0.0037   -1.0093 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9180    0.5315    1.5002 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4048   -0.0031   -1.2605 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5706   -2.0598   -0.1367 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6859   -1.8055    1.2255 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7180   -1.2798    2.5030 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9046    2.3288   -0.9848 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9193    3.4773    0.9574 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4170    2.9789    0.1014 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7387    1.3046   -2.2163 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9177    2.6592   -0.0245 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3727    4.3778   -1.6164 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6930    4.2120   -4.3451 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6598    2.4527   -4.5155 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6992    0.1135   -2.0156 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5575   -2.8949    0.0336 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2167   -5.1566    2.1365 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2732   -5.0548    2.9571 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2604   -4.0691    3.7557 H   0  0  0  0  0  0  0  0  0  0  0  0
 11 10  1  0
 10  8  1  0
  8  9  1  0
  8  7  1  0
  7  6  1  0
  6  5  1  0
  5  4  1  0
  4  3  1  0
  3 16  2  0
 16 25  1  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 28 29  1  0
 28 30  2  0
 30 31  1  0
 31 32  1  0
 31 33  2  0
 33  2  1  0
  2  1  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 20 22  1  0
 22 23  1  0
 22 24  2  0
  5 14  1  0
 14 15  1  0
 14 12  1  0
 12 13  1  0
 12  7  1  0
  2  3  1  0
 24 17  1  0
 33 26  1  0
 11 40  1  0
 10 38  1  0
 10 39  1  0
  8 36  1  1
  9 37  1  0
  7 35  1  6
  5 34  1  6
 27 50  1  0
 29 51  1  0
 30 52  1  0
 32 53  1  0
 18 45  1  0
 19 46  1  0
 21 47  1  0
 23 48  1  0
 24 49  1  0
 14 43  1  1
 15 44  1  0
 12 41  1  6
 13 42  1  0
M  END


  Mrv0541 02241223252D          

 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
    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  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   -2.4750    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  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
    0.0000    0.8250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6674    1.3099    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4125    2.0945    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8974    2.7620    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7179    2.6757    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5619    3.5157    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0468    4.1831    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125    2.0945    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8974    2.7620    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6674    1.3099    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4521    1.0550    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
  7  9  1  0  0  0  0
  9 10  2  0  0  0  0
  3 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  2  0  0  0  0
 13 20  1  0  0  0  0
 12 21  2  0  0  0  0
  2 21  1  0  0  0  0
 21 22  1  0  0  0  0
 23 22  1  1  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  1  0  0  0
 26 27  1  1  0  0  0
 26 28  1  0  0  0  0
 28 29  1  0  0  0  0
 25 30  1  0  0  0  0
 30 31  1  1  0  0  0
 30 32  1  0  0  0  0
 23 32  1  0  0  0  0
 32 33  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0247409

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC[C@@H](O)[C@H]1O[C@@H](OC2=C(OC3=CC(O)=CC(O)=C3C2=O)C2=CC=C(O)C(O)=C2)[C@H](O)[C@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C21H20O12/c22-6-12(27)19-16(29)17(30)21(32-19)33-20-15(28)14-11(26)4-8(23)5-13(14)31-18(20)7-1-2-9(24)10(25)3-7/h1-5,12,16-17,19,21-27,29-30H,6H2/t12-,16-,17-,19-,21+/m1/s1

> <INCHI_KEY>
OPJZLUXFQFQYAI-GNPVFZCLSA-N

> <FORMULA>
C21H20O12

> <MOLECULAR_WEIGHT>
464.3763

> <EXACT_MASS>
464.095476104

> <JCHEM_ACCEPTOR_COUNT>
12

> <JCHEM_AVERAGE_POLARIZABILITY>
43.38675581764807

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
8

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-{[(2S,3R,4R,5R)-5-[(1R)-1,2-dihydroxyethyl]-3,4-dihydroxyoxolan-2-yl]oxy}-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4H-chromen-4-one

> <ALOGPS_LOGP>
0.57

> <JCHEM_LOGP>
-0.14483529600000053

> <ALOGPS_LOGS>
-2.45

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
8.451136982218799

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.433961727037409

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9745070957240873

> <JCHEM_POLAR_SURFACE_AREA>
206.6

> <JCHEM_REFRACTIVITY>
109.27550000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.66e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
quercetin-3-glucoside

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         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       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       2.667  -3.080   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -4.001  -5.390   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      -2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -4.001  -2.310   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       1.246   2.445   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       0.770   3.910   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       1.675   5.156   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       3.207   4.995   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       1.049   6.563   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       1.954   7.808   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      -0.770   3.910   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      -1.675   5.156   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      -1.246   2.445   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      -2.711   1.969   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   21                                                  
CONECT    3    2    4   10                                                  
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9    3   11                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   21                                                  
CONECT   13   12   14   20                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   13                                                       
CONECT   21   12    2   22                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24   32                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26   30                                                  
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   29                                                       
CONECT   29   28                                                            
CONECT   30   25   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30   23   33                                                  
CONECT   33   32                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   72    0
END

View in JSmol

Synonyms

Value	Source
2-(3,4-Dihidroxyphenyl)-3-(beta-D-glucofuranosyloxy)-5,7-dihydroxy-4H-1-benzopyran-4-one	ChEBI
3,3',4',5,7-Pentahydroxyflavone 3-beta-D-glucofuranoside	ChEBI
Isoquercitrin	ChEBI
Isoquercitroside	ChEBI
Isotrifoliin	ChEBI
2-(3,4-Dihidroxyphenyl)-3-(b-D-glucofuranosyloxy)-5,7-dihydroxy-4H-1-benzopyran-4-one	Generator
2-(3,4-Dihidroxyphenyl)-3-(β-D-glucofuranosyloxy)-5,7-dihydroxy-4H-1-benzopyran-4-one	Generator
3,3',4',5,7-Pentahydroxyflavone 3-b-D-glucofuranoside	Generator
3,3',4',5,7-Pentahydroxyflavone 3-β-D-glucofuranoside	Generator
Quercetin 3-O-glucoside	ChEBI
2-(3,4-Dihydroxyphenyl)-3-(beta-D-glucofuranosyloxy)-5,7-dihydroxy-4H-1-benzopyran-4-one	MeSH
4H-1-Benzopyran-4-one, 2-(3,4-dihydroxyphenyl)-3-(beta-D-glucofuranosyloxy)-5,7-dihydroxy	MeSH
Flavone, 3,3',4',5,7-pentahydroxy-, 3-beta-D-glucofuranoside	MeSH
Isoquercetin	MeSH
Isoquercitin	MeSH
Quercetin 3-(beta-D-glucofuranoside)	MeSH
Quercetin 3-O-beta-D-glucofuranoside	MeSH
Quercetin-3-O-beta-glucoside	MeSH
Quercetin-3-O-glucoside	MeSH
Quercetin-3-glucoside	MeSH
Trifoliin	MeSH
Trifoliin a	MeSH

Chemical Formula

C₂₁H₂₀O₁₂

Average Mass

464.3763 Da

Monoisotopic Mass

464.09548 Da

IUPAC Name

3-{[(2S,3R,4R,5R)-5-[(1R)-1,2-dihydroxyethyl]-3,4-dihydroxyoxolan-2-yl]oxy}-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4H-chromen-4-one

Traditional Name

quercetin-3-glucoside

CAS Registry Number

Not Available

SMILES

OC[C@@H](O)[C@H]1O[C@@H](OC2=C(OC3=CC(O)=CC(O)=C3C2=O)C2=CC=C(O)C(O)=C2)[C@H](O)[C@H]1O

InChI Identifier

InChI=1S/C21H20O12/c22-6-12(27)19-16(29)17(30)21(32-19)33-20-15(28)14-11(26)4-8(23)5-13(14)31-18(20)7-1-2-9(24)10(25)3-7/h1-5,12,16-17,19,21-27,29-30H,6H2/t12-,16-,17-,19-,21+/m1/s1

InChI Key

OPJZLUXFQFQYAI-GNPVFZCLSA-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
Aria edulis	LOTUS Database	35616633
Astragalus bornmuellerianus	LOTUS Database	35616633
Camellia japonica	LOTUS Database	35616633
Camellia sinensis	LOTUS Database	35616633
Caragana spinosa	LOTUS Database	35616633
Chenopodium botrys	LOTUS Database	35616633
Globularia bisnagarica	LOTUS Database	35616633
Hypericum brasiliense	LOTUS Database	35616633
Hypericum elegans	LOTUS Database	35616633
Hypericum perforatum	LOTUS Database	35616633
Lagerstroemia speciosa	LOTUS Database	35616633
Lonicera japonica	LOTUS Database	35616633
Marrubium velutinum	LOTUS Database	35616633
Matteuccia struthiopteris	LOTUS Database	35616633
Nelumbo nucifera	LOTUS Database	35616633
Phaseolus vulgaris	LOTUS Database	35616633
Phoenix loureiroi	LOTUS Database	35616633
Phyllanthus virgatus	LOTUS Database	35616633
Polygonum sachalinense	LOTUS Database	35616633
Potentilla anserina	LOTUS Database	35616633
Salix caprea	LOTUS Database	35616633
Trifolium repens	LOTUS Database	35616633
Tripodanthus acutifolius	LOTUS Database	35616633
Viburnum tinus	LOTUS Database	35616633
Vicia sativa	LOTUS Database	35616633
Volutaria lippii	LOTUS Database	35616633
Warburgia ugandensis	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as flavonoid-3-o-glycosides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to carbohydrate moiety at the C3-position.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavonoid glycosides

Direct Parent

Flavonoid-3-O-glycosides

Alternative Parents

Substituents

Flavonoid-3-o-glycoside
3'-hydroxyflavonoid
4'-hydroxyflavonoid
5-hydroxyflavonoid
7-hydroxyflavonoid
Flavone
Hydroxyflavonoid
Chromone
Glycosyl compound
O-glycosyl compound
Benzopyran
1-benzopyran
Pentose monosaccharide
Catechol
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Pyranone
Pyran
Monocyclic benzene moiety
Benzenoid
Monosaccharide
Heteroaromatic compound
Vinylogous acid
Tetrahydrofuran
Secondary alcohol
Oxacycle
Acetal
Organoheterocyclic compound
Hydrocarbon derivative
Organooxygen compound
Alcohol
Organic oxygen compound
Organic oxide
Primary alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

beta-D-glucoside (CHEBI:28299 )
monosaccharide derivative (CHEBI:28299 )
tetrahydroxyflavone (CHEBI:28299 )
quercetin O-glucoside (CHEBI:28299 )

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	0.57	ALOGPS
logP	-0.14	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Acidic)	6.43	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	12	ChemAxon
Hydrogen Donor Count	8	ChemAxon
Polar Surface Area	206.6 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	109.28 m³·mol⁻¹	ChemAxon
Polarizability	43.39 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

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Isoquercetin

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

28299

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for quercetin-3-glucoside (NP0247409)

MOL for NP0247409 (quercetin-3-glucoside)

3D MOL for NP0247409 (quercetin-3-glucoside)

3D SDF for NP0247409 (quercetin-3-glucoside)

3D-SDF for NP0247409 (quercetin-3-glucoside)

PDB for NP0247409 (quercetin-3-glucoside)

3D PDB for NP0247409 (quercetin-3-glucoside)

SMILES for NP0247409 (quercetin-3-glucoside)

INCHI for NP0247409 (quercetin-3-glucoside)

Structure for NP0247409 (quercetin-3-glucoside)

3D Structure for NP0247409 (quercetin-3-glucoside)