NP-MRD: Showing NP-Card for Quercetin 3-beta-O-glucuronide (NP0043958)

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Record Information

Version

1.0

Created at

2021-06-22 17:42:48 UTC

Updated at

2021-08-20 00:00:49 UTC

NP-MRD ID

NP0043958

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Quercetin 3-beta-O-glucuronide

Description

Miquelianin, also known as quercituron, belongs to the class of organic compounds known as flavonoid-3-o-glucuronides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to glucuronic acid at the C3-position. Thus, miquelianin is considered to be a flavonoid. Miquelianin is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Quercetin 3-beta-O-glucuronide is found in Alnus sieboldiana, Foeniculum vulgare , Arachis hypogaea, Callistemon citrinus, Campanula glomerata, Centella asiatica, Centella erecta, Clematis rehderiana, Clematis stans, Cornus mas, Corsinia coriandrina, Corylus heterophylla, Cyclocarya paliurus, Diospyros cathayensis, Epilobium hirsutum, Eucalyptus consideniana, Eucalyptus globulus, Euphorbia retusa, Gaultheria pyroloides, Hamamelis virginiana, Hypericum aucheri, Hypericum henryi, Hypericum hirsutum, Hypericum laricifolium, Morella rubra, Nelumbo nucifera, Persicaria decipiens, Phaseolus vulgaris, Fallopia sachalinensis, Potentilla anserina, Rosa multiflora, Rubus glaucus, Schinus molle, Tamarix nilotica, Vigna radiata, Vitis vinifera and Vitis vinifera. It was first documented in 1999 (PMID: 10479312). Based on a literature review a significant number of articles have been published on miquelianin (PMID: 19061313) (PMID: 11809447) (PMID: 14735439) (PMID: 15742803).

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI


  Mrv1652306222119422D          

 34 37  0  0  1  0            999 V2000
   -0.7145   -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
   -1.4289   -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
    0.0000   -2.4750    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
    0.7145   -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
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    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
    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
    2.1434   -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
    4.2868   -1.6500    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
    0.0000    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  1  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  2  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
    1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -3.7125    0.0000 O   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  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
  5  6  2  0  0  0  0
  1  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
 11 12  2  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
 11 16  1  0  0  0  0
 16 17  1  0  0  0  0
  7 17  1  0  0  0  0
 14 18  1  0  0  0  0
 12 19  1  0  0  0  0
  8 20  1  0  0  0  0
 21 20  1  1  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 21 26  1  0  0  0  0
 25 27  1  1  0  0  0
 27 28  2  0  0  0  0
 27 29  1  0  0  0  0
 24 30  1  6  0  0  0
 23 31  1  1  0  0  0
 22 32  1  6  0  0  0
  4 33  1  0  0  0  0
  3 34  1  0  0  0  0
M  END

NP0043958
     RDKit          3D

 52 55  0  0  0  0  0  0  0  0999 V2000
   -5.4151    1.5952   -1.6550 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2719    1.7511   -1.1598 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6372    2.9835   -1.1921 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5975    0.6154   -0.5385 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.3455    0.9225   -0.0325 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6009   -0.2530    0.2205 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4695    0.2056    0.9689 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6872    0.6154    0.3911 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7950   -0.1173    0.1723 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8980   -1.5099    0.5675 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0833   -2.1823    1.4141 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2451   -3.5407    1.6896 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2530   -4.2612    1.1057 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4330   -5.6249    1.3682 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0919   -3.6016    0.2454 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1216   -4.3117   -0.3580 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9274   -2.2657   -0.0221 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8776    0.4284   -0.4365 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9490    1.6539   -0.8451 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1046    2.1494   -1.4677 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1948    3.4504   -1.9069 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3501    3.9238   -2.5226 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0916    4.2588   -1.7091 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9463    3.7774   -1.0951 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8359    4.5944   -0.8970 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8601    2.4750   -0.6571 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7355    1.9636   -0.0439 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2615    2.6786    0.1396 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3239   -1.2650    0.9797 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.9262   -2.5415    0.4974 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8229   -1.2731    0.9186 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.3045   -1.8397    2.1082 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3758    0.0919    0.6797 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.7303    0.1177    0.4595 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1292    3.1958   -2.0544 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4833   -0.2548   -1.2373 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2844   -0.5854   -0.7723 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3041   -1.6394    1.9090 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5523   -3.9926    2.3725 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8247   -6.1284    1.9995 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2853   -5.2801   -0.1993 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6354   -1.8144   -0.7169 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9490    1.4719   -1.6009 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1154    4.3449   -2.0158 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1465    5.2995   -2.0534 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8116    5.5626   -1.1868 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0115   -1.2692    2.0677 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3609   -3.2390    1.0384 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1562   -1.9684    0.1099 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4516   -1.1647    2.8133 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0995    0.7505    1.5400 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0466    1.0466    0.6002 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
 15 17  2  0
  9 18  1  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  1  0
 21 23  2  0
 23 24  1  0
 24 25  1  0
 24 26  2  0
 26 27  1  0
 27 28  2  0
  6 29  1  0
 29 30  1  0
 29 31  1  0
 31 32  1  0
 31 33  1  0
 33 34  1  0
 33  4  1  0
 27  8  1  0
 17 10  1  0
 26 19  1  0
  3 35  1  0
  4 36  1  6
  6 37  1  6
 11 38  1  0
 12 39  1  0
 14 40  1  0
 16 41  1  0
 17 42  1  0
 20 43  1  0
 22 44  1  0
 23 45  1  0
 25 46  1  0
 29 47  1  1
 30 48  1  0
 31 49  1  6
 32 50  1  0
 33 51  1  1
 34 52  1  0
M  END


  Mrv1652306222119422D          

 34 37  0  0  1  0            999 V2000
   -0.7145   -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
   -1.4289   -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
    0.0000   -2.4750    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
    0.7145   -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
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    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
    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
    2.1434   -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
    4.2868   -1.6500    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
    0.0000    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  1  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  2  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
    1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -3.7125    0.0000 O   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  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
  5  6  2  0  0  0  0
  1  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
 11 12  2  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
 11 16  1  0  0  0  0
 16 17  1  0  0  0  0
  7 17  1  0  0  0  0
 14 18  1  0  0  0  0
 12 19  1  0  0  0  0
  8 20  1  0  0  0  0
 21 20  1  1  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 21 26  1  0  0  0  0
 25 27  1  1  0  0  0
 27 28  2  0  0  0  0
 27 29  1  0  0  0  0
 24 30  1  6  0  0  0
 23 31  1  1  0  0  0
 22 32  1  6  0  0  0
  4 33  1  0  0  0  0
  3 34  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0043958

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C21H18O13/c22-7-4-10(25)12-11(5-7)32-17(6-1-2-8(23)9(24)3-6)18(13(12)26)33-21-16(29)14(27)15(28)19(34-21)20(30)31/h1-5,14-16,19,21-25,27-29H,(H,30,31)/t14-,15-,16+,19-,21+/m0/s1

> <INCHI_KEY>
DUBCCGAQYVUYEU-ZUGPOPFOSA-N

> <FORMULA>
C21H18O13

> <MOLECULAR_WEIGHT>
478.362

> <EXACT_MASS>
478.07474064

> <JCHEM_ACCEPTOR_COUNT>
13

> <JCHEM_ATOM_COUNT>
52

> <JCHEM_AVERAGE_POLARIZABILITY>
43.54762984523291

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
8

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2S,3S,4S,5R,6S)-6-{[2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxo-4H-chromen-3-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid

> <ALOGPS_LOGP>
1.37

> <JCHEM_LOGP>
0.17543924199999955

> <ALOGPS_LOGS>
-2.30

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
6.372487259298597

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.6505516813380225

> <JCHEM_PKA_STRONGEST_BASIC>
-3.7319986993890746

> <JCHEM_POLAR_SURFACE_AREA>
223.66999999999996

> <JCHEM_REFRACTIVITY>
109.1429

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.40e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S,3S,4S,5R,6S)-6-{[2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxochromen-3-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

NP0043958
     RDKit          3D

 52 55  0  0  0  0  0  0  0  0999 V2000
   -5.4151    1.5952   -1.6550 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2719    1.7511   -1.1598 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6372    2.9835   -1.1921 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5975    0.6154   -0.5385 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.3455    0.9225   -0.0325 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6009   -0.2530    0.2205 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4695    0.2056    0.9689 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6872    0.6154    0.3911 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7950   -0.1173    0.1723 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8980   -1.5099    0.5675 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0833   -2.1823    1.4141 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2451   -3.5407    1.6896 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2530   -4.2612    1.1057 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4330   -5.6249    1.3682 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0919   -3.6016    0.2454 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1216   -4.3117   -0.3580 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9274   -2.2657   -0.0221 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8776    0.4284   -0.4365 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9490    1.6539   -0.8451 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1046    2.1494   -1.4677 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1948    3.4504   -1.9069 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3501    3.9238   -2.5226 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0916    4.2588   -1.7091 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9463    3.7774   -1.0951 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8359    4.5944   -0.8970 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8601    2.4750   -0.6571 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7355    1.9636   -0.0439 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2615    2.6786    0.1396 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3239   -1.2650    0.9797 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.9262   -2.5415    0.4974 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8229   -1.2731    0.9186 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.3045   -1.8397    2.1082 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3758    0.0919    0.6797 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.7303    0.1177    0.4595 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1292    3.1958   -2.0544 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4833   -0.2548   -1.2373 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2844   -0.5854   -0.7723 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3041   -1.6394    1.9090 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5523   -3.9926    2.3725 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8247   -6.1284    1.9995 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2853   -5.2801   -0.1993 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6354   -1.8144   -0.7169 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9490    1.4719   -1.6009 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1154    4.3449   -2.0158 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1465    5.2995   -2.0534 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8116    5.5626   -1.1868 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0115   -1.2692    2.0677 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3609   -3.2390    1.0384 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1562   -1.9684    0.1099 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4516   -1.1647    2.8133 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0995    0.7505    1.5400 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0466    1.0466    0.6002 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
 15 17  2  0
  9 18  1  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  1  0
 21 23  2  0
 23 24  1  0
 24 25  1  0
 24 26  2  0
 26 27  1  0
 27 28  2  0
  6 29  1  0
 29 30  1  0
 29 31  1  0
 31 32  1  0
 31 33  1  0
 33 34  1  0
 33  4  1  0
 27  8  1  0
 17 10  1  0
 26 19  1  0
  3 35  1  0
  4 36  1  6
  6 37  1  6
 11 38  1  0
 12 39  1  0
 14 40  1  0
 16 41  1  0
 17 42  1  0
 20 43  1  0
 22 44  1  0
 23 45  1  0
 25 46  1  0
 29 47  1  1
 30 48  1  0
 31 49  1  6
 32 50  1  0
 33 51  1  1
 34 52  1  0
M  END

HEADER    PROTEIN                                 22-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   22-JUN-21         0                                  
HETATM    1  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       2.667   1.540   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       2.667  -3.080   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       8.002  -3.080   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       5.335   1.540   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -1.334   3.850   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       1.334   3.850   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       1.334   2.310   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       2.667   6.160   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0       4.001   3.850   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0       0.000   6.160   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0      -2.667   4.620   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0      -2.667   1.540   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0      -1.334  -6.930   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0      -4.001  -5.390   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4   34                                                  
CONECT    4    3    5   33                                                  
CONECT    5    4    6                                                       
CONECT    6    5    1    7                                                  
CONECT    7    6    8   17                                                  
CONECT    8    7    9   20                                                  
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   16                                                  
CONECT   12   11   13   19                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   18                                                  
CONECT   15   14   16                                                       
CONECT   16   15   11   17                                                  
CONECT   17   16    7                                                       
CONECT   18   14                                                            
CONECT   19   12                                                            
CONECT   20    8   21                                                       
CONECT   21   20   22   26                                                  
CONECT   22   21   23   32                                                  
CONECT   23   22   24   31                                                  
CONECT   24   23   25   30                                                  
CONECT   25   24   26   27                                                  
CONECT   26   25   21                                                       
CONECT   27   25   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27                                                            
CONECT   30   24                                                            
CONECT   31   23                                                            
CONECT   32   22                                                            
CONECT   33    4                                                            
CONECT   34    3                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   74    0
END

COMPND    NP0043958
HETATM    1  O1  UNL     1      -5.415   1.595  -1.655  1.00  0.00           O  
HETATM    2  C1  UNL     1      -4.272   1.751  -1.160  1.00  0.00           C  
HETATM    3  O2  UNL     1      -3.637   2.983  -1.192  1.00  0.00           O  
HETATM    4  C2  UNL     1      -3.597   0.615  -0.538  1.00  0.00           C  
HETATM    5  O3  UNL     1      -2.345   0.923  -0.033  1.00  0.00           O  
HETATM    6  C3  UNL     1      -1.601  -0.253   0.220  1.00  0.00           C  
HETATM    7  O4  UNL     1      -0.469   0.206   0.969  1.00  0.00           O  
HETATM    8  C4  UNL     1       0.687   0.615   0.391  1.00  0.00           C  
HETATM    9  C5  UNL     1       1.795  -0.117   0.172  1.00  0.00           C  
HETATM   10  C6  UNL     1       1.898  -1.510   0.567  1.00  0.00           C  
HETATM   11  C7  UNL     1       1.083  -2.182   1.414  1.00  0.00           C  
HETATM   12  C8  UNL     1       1.245  -3.541   1.690  1.00  0.00           C  
HETATM   13  C9  UNL     1       2.253  -4.261   1.106  1.00  0.00           C  
HETATM   14  O5  UNL     1       2.433  -5.625   1.368  1.00  0.00           O  
HETATM   15  C10 UNL     1       3.092  -3.602   0.245  1.00  0.00           C  
HETATM   16  O6  UNL     1       4.122  -4.312  -0.358  1.00  0.00           O  
HETATM   17  C11 UNL     1       2.927  -2.266  -0.022  1.00  0.00           C  
HETATM   18  O7  UNL     1       2.878   0.428  -0.436  1.00  0.00           O  
HETATM   19  C12 UNL     1       2.949   1.654  -0.845  1.00  0.00           C  
HETATM   20  C13 UNL     1       4.105   2.149  -1.468  1.00  0.00           C  
HETATM   21  C14 UNL     1       4.195   3.450  -1.907  1.00  0.00           C  
HETATM   22  O8  UNL     1       5.350   3.924  -2.523  1.00  0.00           O  
HETATM   23  C15 UNL     1       3.092   4.259  -1.709  1.00  0.00           C  
HETATM   24  C16 UNL     1       1.946   3.777  -1.095  1.00  0.00           C  
HETATM   25  O9  UNL     1       0.836   4.594  -0.897  1.00  0.00           O  
HETATM   26  C17 UNL     1       1.860   2.475  -0.657  1.00  0.00           C  
HETATM   27  C18 UNL     1       0.735   1.964  -0.044  1.00  0.00           C  
HETATM   28  O10 UNL     1      -0.262   2.679   0.140  1.00  0.00           O  
HETATM   29  C19 UNL     1      -2.324  -1.265   0.980  1.00  0.00           C  
HETATM   30  O11 UNL     1      -1.926  -2.541   0.497  1.00  0.00           O  
HETATM   31  C20 UNL     1      -3.823  -1.273   0.919  1.00  0.00           C  
HETATM   32  O12 UNL     1      -4.304  -1.840   2.108  1.00  0.00           O  
HETATM   33  C21 UNL     1      -4.376   0.092   0.680  1.00  0.00           C  
HETATM   34  O13 UNL     1      -5.730   0.118   0.459  1.00  0.00           O  
HETATM   35  H1  UNL     1      -3.129   3.196  -2.054  1.00  0.00           H  
HETATM   36  H2  UNL     1      -3.483  -0.255  -1.237  1.00  0.00           H  
HETATM   37  H3  UNL     1      -1.284  -0.585  -0.772  1.00  0.00           H  
HETATM   38  H4  UNL     1       0.304  -1.639   1.909  1.00  0.00           H  
HETATM   39  H5  UNL     1       0.552  -3.993   2.372  1.00  0.00           H  
HETATM   40  H6  UNL     1       1.825  -6.128   1.999  1.00  0.00           H  
HETATM   41  H7  UNL     1       4.285  -5.280  -0.199  1.00  0.00           H  
HETATM   42  H8  UNL     1       3.635  -1.814  -0.717  1.00  0.00           H  
HETATM   43  H9  UNL     1       4.949   1.472  -1.601  1.00  0.00           H  
HETATM   44  H10 UNL     1       6.115   4.345  -2.016  1.00  0.00           H  
HETATM   45  H11 UNL     1       3.147   5.299  -2.053  1.00  0.00           H  
HETATM   46  H12 UNL     1       0.812   5.563  -1.187  1.00  0.00           H  
HETATM   47  H13 UNL     1      -2.011  -1.269   2.068  1.00  0.00           H  
HETATM   48  H14 UNL     1      -2.361  -3.239   1.038  1.00  0.00           H  
HETATM   49  H15 UNL     1      -4.156  -1.968   0.110  1.00  0.00           H  
HETATM   50  H16 UNL     1      -4.452  -1.165   2.813  1.00  0.00           H  
HETATM   51  H17 UNL     1      -4.099   0.750   1.540  1.00  0.00           H  
HETATM   52  H18 UNL     1      -6.047   1.047   0.600  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    4
CONECT    3   35
CONECT    4    5   33   36
CONECT    5    6
CONECT    6    7   29   37
CONECT    7    8
CONECT    8    9    9   27
CONECT    9   10   18
CONECT   10   11   11   17
CONECT   11   12   38
CONECT   12   13   13   39
CONECT   13   14   15
CONECT   14   40
CONECT   15   16   17   17
CONECT   16   41
CONECT   17   42
CONECT   18   19
CONECT   19   20   20   26
CONECT   20   21   43
CONECT   21   22   23   23
CONECT   22   44
CONECT   23   24   45
CONECT   24   25   26   26
CONECT   25   46
CONECT   26   27
CONECT   27   28   28
CONECT   29   30   31   47
CONECT   30   48
CONECT   31   32   33   49
CONECT   32   50
CONECT   33   34   51
CONECT   34   52
END

NP0043958
     RDKit          3D

52 55  0  0  0  0  0  0  0  0999 V2000
   -5.4151    1.5952   -1.6550 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2719    1.7511   -1.1598 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6372    2.9835   -1.1921 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5975    0.6154   -0.5385 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.3455    0.9225   -0.0325 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6009   -0.2530    0.2205 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4695    0.2056    0.9689 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6872    0.6154    0.3911 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7950   -0.1173    0.1723 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8980   -1.5099    0.5675 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0833   -2.1823    1.4141 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2451   -3.5407    1.6896 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2530   -4.2612    1.1057 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4330   -5.6249    1.3682 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0919   -3.6016    0.2454 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1216   -4.3117   -0.3580 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9274   -2.2657   -0.0221 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8776    0.4284   -0.4365 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9490    1.6539   -0.8451 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1046    2.1494   -1.4677 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1948    3.4504   -1.9069 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3501    3.9238   -2.5226 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0916    4.2588   -1.7091 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9463    3.7774   -1.0951 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8359    4.5944   -0.8970 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8601    2.4750   -0.6571 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7355    1.9636   -0.0439 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2615    2.6786    0.1396 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3239   -1.2650    0.9797 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.9262   -2.5415    0.4974 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8229   -1.2731    0.9186 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.3045   -1.8397    2.1082 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3758    0.0919    0.6797 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.7303    0.1177    0.4595 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1292    3.1958   -2.0544 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4833   -0.2548   -1.2373 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2844   -0.5854   -0.7723 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3041   -1.6394    1.9090 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5523   -3.9926    2.3725 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8247   -6.1284    1.9995 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2853   -5.2801   -0.1993 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6354   -1.8144   -0.7169 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9490    1.4719   -1.6009 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1154    4.3449   -2.0158 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1465    5.2995   -2.0534 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8116    5.5626   -1.1868 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0115   -1.2692    2.0677 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3609   -3.2390    1.0384 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1562   -1.9684    0.1099 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4516   -1.1647    2.8133 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0995    0.7505    1.5400 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0466    1.0466    0.6002 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
 15 17  2  0
  9 18  1  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  1  0
 21 23  2  0
 23 24  1  0
 24 25  1  0
 24 26  2  0
 26 27  1  0
 27 28  2  0
  6 29  1  0
 29 30  1  0
 29 31  1  0
 31 32  1  0
 31 33  1  0
 33 34  1  0
 33  4  1  0
 27  8  1  0
 17 10  1  0
 26 19  1  0
  3 35  1  0
  4 36  1  6
  6 37  1  6
 11 38  1  0
 12 39  1  0
 14 40  1  0
 16 41  1  0
 17 42  1  0
 20 43  1  0
 22 44  1  0
 23 45  1  0
 25 46  1  0
 29 47  1  1
 30 48  1  0
 31 49  1  6
 32 50  1  0
 33 51  1  1
 34 52  1  0
M  END

View in JSmol

Synonyms

Value	Source
Quercetin 3-O-glucuronide	ChEBI
Quercetin-3-O-beta-D-glucuronopyranoside	ChEBI
Quercetin-3-O-glucoronoside	ChEBI
Quercituron	ChEBI
Quercetin-3-O-b-D-glucuronopyranoside	Generator
Quercetin-3-O-β-D-glucuronopyranoside	Generator
Quercetin 3-O-beta-D-glucopyranoside	MeSH
Quercetin 3-O-beta-glucopyranoside	MeSH
Quercetin 3-O-glucopyranoside	MeSH
Querciturone	MeSH

Chemical Formula

C₂₁H₁₈O₁₃

Average Mass

478.3620 Da

Monoisotopic Mass

478.07474 Da

IUPAC Name

(2S,3S,4S,5R,6S)-6-{[2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxo-4H-chromen-3-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid

Traditional Name

(2S,3S,4S,5R,6S)-6-{[2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxochromen-3-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C21H18O13/c22-7-4-10(25)12-11(5-7)32-17(6-1-2-8(23)9(24)3-6)18(13(12)26)33-21-16(29)14(27)15(28)19(34-21)20(30)31/h1-5,14-16,19,21-25,27-29H,(H,30,31)/t14-,15-,16+,19-,21+/m0/s1

InChI Key

DUBCCGAQYVUYEU-ZUGPOPFOSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 150 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 250 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 175 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 225 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 125 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Adiantum spp.	KNApSAcK Database	22123792
Alnus sieboldiana	LOTUS Database	35616633
Alpinia elatior	KNApSAcK Database	22123792
Anethum foeniculum	Plant	KNApSAcK
Anethum sowa	KNApSAcK Database	22123792
Arachis hypogaea	LOTUS Database	35616633
Arnica chamissonis	KNApSAcK Database	22123792
Beilschmiedia miersii	KNApSAcK Database	22123792
Callistemon citrinus	LOTUS Database	35616633
Campanula glomerata	LOTUS Database	35616633
Campanula glomerata L.	KNApSAcK Database	22123792
Cautleya spicata	KNApSAcK Database	22123792
Centella asiatica	LOTUS Database	35616633
Centella erecta	LOTUS Database	35616633
Clematis rehderiana	LOTUS Database	35616633
Clematis stans	LOTUS Database	35616633
Cornus mas	LOTUS Database	35616633
Corsinia coriandrina	-	KNApSAcK
Corylus heterophylla	LOTUS Database	35616633
Cyclocarya paliurus	LOTUS Database	35616633
Diospyros cathayensis	LOTUS Database	35616633
Epilobium hirsutum	LOTUS Database	35616633
Eriogonum nudum	KNApSAcK Database	22123792
Eucalyptus consideniana	LOTUS Database	35616633
Eucalyptus globulus	LOTUS Database	35616633
Euphorbia retusa	LOTUS Database	35616633
Euphorbia spp.	KNApSAcK Database	22123792
Foeniculum vulgare	KNApSAcK Database	22123792
Fuchsia fulgens	KNApSAcK Database	22123792
Gaultheria miqueliana	KNApSAcK Database	22123792
Gaultheria pyroloides	LOTUS Database	35616633
Geranium dissectum	KNApSAcK Database	22123792
Gutierrezia wrightii	KNApSAcK Database	22123792
Hamamelis virginiana	LOTUS Database	35616633
Hedychium thyrsiforme	KNApSAcK Database	22123792
Hypericum aucheri	LOTUS Database	35616633
Hypericum henryi	LOTUS Database	35616633
Hypericum hirsutum	LOTUS Database	35616633
Hypericum laricifolium	LOTUS Database	35616633
Hypericum perforatum	KNApSAcK Database	22123792
Monsonia spp.	KNApSAcK Database	22123792
Morella rubra	LOTUS Database	35616633
Nelumbo nucifera	LOTUS Database	35616633
Orlaya spp. Lasthenia spp.	KNApSAcK Database	22123792
Persicaria decipiens	LOTUS Database	35616633
Phaseolus vulgaris	LOTUS Database	35616633
Philydrum lanuginosum	KNApSAcK Database	22123792
Polygonum hydropiper L.	KNApSAcK Database	22123792
Polygonum sachalinense	LOTUS Database	35616633
Polygonum viviparum	KNApSAcK Database	22123792
Populus grandidentata	KNApSAcK Database	22123792
Potentilla anserina	LOTUS Database	35616633
Psidium guaijava	KNApSAcK Database	22123792
Rosa luciae	KNApSAcK Database	22123792
Rosa multiflora	LOTUS Database	35616633
Rubus glaucus	LOTUS Database	35616633
Salvia blepharophylla	KNApSAcK Database	22123792
Schinus molle	LOTUS Database	35616633
Stephanodoria tomentella	KNApSAcK Database	22123792
Tamarix nilotica	LOTUS Database	35616633
Theobroma grandiflorum	KNApSAcK Database	22123792
Vigna radiata	LOTUS Database	35616633
Vitis vinifera	LOTUS Database	35616633
Vitis vinifera L.	Linigton's dataset	19061313

Chemical Taxonomy

Description

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

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavonoid glycosides

Direct Parent

Flavonoid-3-O-glucuronides

Alternative Parents

Substituents

Flavonoid-3-o-glucuronide
Flavonoid-3-o-glycoside
3'-hydroxyflavonoid
4'-hydroxyflavonoid
5-hydroxyflavonoid
7-hydroxyflavonoid
Flavone
Hydroxyflavonoid
1-o-glucuronide
O-glucuronide
Glucuronic acid or derivatives
Hexose monosaccharide
Chromone
Glycosyl compound
O-glycosyl compound
Benzopyran
1-benzopyran
Catechol
Beta-hydroxy acid
Pyranone
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Monosaccharide
Oxane
Hydroxy acid
Monocyclic benzene moiety
Benzenoid
Pyran
Heteroaromatic compound
Vinylogous acid
Secondary alcohol
Monocarboxylic acid or derivatives
Acetal
Polyol
Organoheterocyclic compound
Carboxylic acid derivative
Carboxylic acid
Oxacycle
Organooxygen compound
Organic oxide
Hydrocarbon derivative
Carbonyl group
Organic oxygen compound
Alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

beta-D-glucosiduronic acid (CHEBI:66395 )
quercetin O-glycoside (CHEBI:66395 )

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	927.80 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	6307 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	2.100 (est)	The Good Scents Company Information System

Predicted Properties

Property	Value	Source
logP	1.37	ALOGPS
logP	0.18	ChemAxon
logS	-2.3	ALOGPS
pKa (Strongest Acidic)	2.65	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	13	ChemAxon
Hydrogen Donor Count	8	ChemAxon
Polar Surface Area	223.67 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	109.14 m³·mol⁻¹	ChemAxon
Polarizability	43.55 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

C00005376

Chemspider ID

4438874

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Miquelianin

METLIN ID

Not Available

PubChem Compound

5274585

PDB ID

Not Available

ChEBI ID

66395

Good Scents ID

rw1699061

References

General References

Castillo-Munoz N, Gomez-Alonso S, Garcia-Romero E, Gomez MV, Velders AH, Hermosin-Gutierrez I: Flavonol 3-O-glycosides series of Vitis vinifera Cv. Petit Verdot red wine grapes. J Agric Food Chem. 2009 Jan 14;57(1):209-19. doi: 10.1021/jf802863g. [PubMed:19061313 ]
Calis I, Kuruuzum A, Demirezer LO, Sticher O, Ganci W, Ruedi P: Phenylvaleric acid and flavonoid glycosides from Polygonum salicifolium. J Nat Prod. 1999 Aug;62(8):1101-5. doi: 10.1021/np9900674. [PubMed:10479312 ]
Lu Y, Foo LY: Polyphenolics of Salvia--a review. Phytochemistry. 2002 Jan;59(2):117-40. doi: 10.1016/s0031-9422(01)00415-0. [PubMed:11809447 ]
Juergenliemk G, Boje K, Huewel S, Lohmann C, Galla HJ, Nahrstedt A: In vitro studies indicate that miquelianin (quercetin 3-O-beta-D-glucuronopyranoside) is able to reach the CNS from the small intestine. Planta Med. 2003 Nov;69(11):1013-7. doi: 10.1055/s-2003-45148. [PubMed:14735439 ]
Zhang X, Thuong PT, Jin W, Su ND, Sok DE, Bae K, Kang SS: Antioxidant activity of anthraquinones and flavonoids from flower of Reynoutria sachalinensis. Arch Pharm Res. 2005 Jan;28(1):22-7. doi: 10.1007/BF02975130. [PubMed:15742803 ]

Showing NP-Card for Quercetin 3-beta-O-glucuronide (NP0043958)

MOL for NP0043958 (Quercetin 3-beta-O-glucuronide)

3D MOL for NP0043958 (Quercetin 3-beta-O-glucuronide)

3D SDF for NP0043958 (Quercetin 3-beta-O-glucuronide)

3D-SDF for NP0043958 (Quercetin 3-beta-O-glucuronide)

PDB for NP0043958 (Quercetin 3-beta-O-glucuronide)

3D PDB for NP0043958 (Quercetin 3-beta-O-glucuronide)

SMILES for NP0043958 (Quercetin 3-beta-O-glucuronide)

INCHI for NP0043958 (Quercetin 3-beta-O-glucuronide)

Structure for NP0043958 (Quercetin 3-beta-O-glucuronide)

3D Structure for NP0043958 (Quercetin 3-beta-O-glucuronide)