NP-MRD: Showing NP-Card for 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-{[(2r,3s,4r,5r,6s)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}chromen-4-one (NP0223638)

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Record Information

Version

2.0

Created at

2022-09-06 01:47:25 UTC

Updated at

2022-09-06 01:47:25 UTC

NP-MRD ID

NP0223638

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-{[(2r,3s,4r,5r,6s)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}chromen-4-one

Description

Isoquercitin, also known as trifoliin, 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. 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-{[(2r,3s,4r,5r,6s)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}chromen-4-one is found in Alnus japonica, Conyza filaginoides, Corchorus olitorius, Eucalyptus viminalis, Geranium collinum, Hippophae rhamnoides, Chaiturus marrubiastrum, Lepisorus contortus, Rheum rhaponticum, Rhododendron dauricum, Solidago canadensis, Sorbus tianschanica, Stylosanthes erecta and Trifolium arvense. 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-{[(2r,3s,4r,5r,6s)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}chromen-4-one was first documented in 2013 (PMID: 23786717). Based on a literature review a significant number of articles have been published on isoquercitin (PMID: 35472682) (PMID: 35482747) (PMID: 35431593) (PMID: 33356000) (PMID: 33305598) (PMID: 32458896).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309062203472D          

 33 36  0  0  1  0            999 V2000
    1.4289   -2.4750    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
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -3.7125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4289   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.1250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0000   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -3.7125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4289   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.8875    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4289   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    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
    4.2868   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  5  4  1  1  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
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  8  9  1  0  0  0  0
  7 10  1  0  0  0  0
 10 11  1  6  0  0  0
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  5 14  1  0  0  0  0
 14 15  1  6  0  0  0
  3 16  2  0  0  0  0
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 28 30  2  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 31 33  2  0  0  0  0
  2 33  1  0  0  0  0
 26 33  1  0  0  0  0
M  END

     RDKit          3D

 53 56  0  0  0  0  0  0  0  0999 V2000
    0.1852    2.5264   -1.7930 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7996    1.8580   -1.3915 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6835    0.5108   -1.0200 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5683   -0.0603   -1.0977 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4997    0.0547   -0.0156 C   0  0  1  0  0  0  0  0  0  0  0  0
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    2.7094   -0.9472    1.5750 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.3156   -2.1985    2.1335 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0229   -1.8217    3.2981 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8358    0.0503    1.3503 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.4488    1.2437    1.9593 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9281    0.2727   -0.1463 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.9509   -0.9735   -0.8094 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6327    0.9395   -0.5619 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6129    2.1845    0.1018 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7741   -0.1748   -0.5950 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8114   -1.5584   -0.1856 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9254   -2.0527    0.4995 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0618   -3.3629    0.8806 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0603   -4.2599    0.5836 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1861   -5.5999    0.9672 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9438   -3.8299   -0.0882 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0625   -4.7403   -0.3843 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8423   -2.4830   -0.4610 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9372    0.4937   -0.5473 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0816    1.7321   -0.8792 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3386    2.3366   -0.7934 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5101    3.6574   -1.1440 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7919    4.2158   -1.0394 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4206    4.3644   -1.5787 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1632    3.8102   -1.6793 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0688    4.5170   -2.1150 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0241    2.4760   -1.3179 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0400    0.5807    0.8589 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9827   -0.5701    2.3501 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0596   -2.6215    1.4326 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5401   -2.9607    2.3937 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4127   -1.7082    4.0689 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7948   -0.3196    1.7618 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2004    1.8833    2.0487 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8135    0.8740   -0.4312 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3077   -1.0111   -1.5478 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5875    1.0383   -1.6484 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9661    2.9090   -0.4410 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7060   -1.3363    0.7280 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9269   -3.7218    1.4070 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4462   -6.2500    0.7447 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8877   -4.4023   -0.8854 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0438   -2.2146   -1.0147 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1744    1.7482   -0.4464 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9878    5.1672   -1.2769 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5904    5.4067   -1.8483 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1336    5.4819   -2.3840 H   0  0  0  0  0  0  0  0  0  0  0  0
  9  8  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
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 22 23  1  0
 22 24  2  0
  5 14  1  0
 14 15  1  0
 14 12  1  0
 12 13  1  0
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 10 11  1  0
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  2  3  1  0
 24 17  1  0
 33 26  1  0
  9 38  1  0
  8 36  1  0
  8 37  1  0
  7 35  1  1
  5 34  1  1
 27 50  1  0
 29 51  1  0
 30 52  1  0
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 18 45  1  0
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 23 48  1  0
 24 49  1  0
 14 43  1  6
 15 44  1  0
 12 41  1  1
 13 42  1  0
 10 39  1  1
 11 40  1  0
M  END


  Mrv1652309062203472D          

 33 36  0  0  1  0            999 V2000
    1.4289   -2.4750    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
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -3.7125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4289   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.1250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0000   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -3.7125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4289   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.8875    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4289   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    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
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    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  5  4  1  1  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  1  0  0  0
  8  9  1  0  0  0  0
  7 10  1  0  0  0  0
 10 11  1  6  0  0  0
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 12 13  1  1  0  0  0
 12 14  1  0  0  0  0
  5 14  1  0  0  0  0
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  3 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
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 22 24  2  0  0  0  0
 17 24  1  0  0  0  0
 16 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
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 31 33  2  0  0  0  0
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M  END
> <DATABASE_ID>
NP0223638

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC[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](O)[C@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C21H20O12/c22-6-13-15(27)17(29)18(30)21(32-13)33-20-16(28)14-11(26)4-8(23)5-12(14)31-19(20)7-1-2-9(24)10(25)3-7/h1-5,13,15,17-18,21-27,29-30H,6H2/t13-,15-,17+,18-,21+/m0/s1

> <INCHI_KEY>
OVSQVDMCBVZWGM-LQSBFMDOSA-N

> <FORMULA>
C21H20O12

> <MOLECULAR_WEIGHT>
464.379

> <EXACT_MASS>
464.095476084

> <JCHEM_ACCEPTOR_COUNT>
12

> <JCHEM_ATOM_COUNT>
53

> <JCHEM_AVERAGE_POLARIZABILITY>
43.07217698062724

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
8

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <JCHEM_LOGP>
-0.14483529600000053

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
7.87252087509293

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.372405531686565

> <JCHEM_PKA_STRONGEST_BASIC>
-2.98109237118166

> <JCHEM_POLAR_SURFACE_AREA>
206.6

> <JCHEM_REFRACTIVITY>
109.27550000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-{[(2R,3S,4R,5R,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}chromen-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  -4.620   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       0.000  -3.080   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       1.334  -5.390   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.667  -7.700   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       2.667  -9.240   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       0.000  -7.700   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       0.000  -9.240   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      -1.334  -6.930   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -2.667  -7.700   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -2.667  -4.620   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -2.667   0.000   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -2.667   1.540   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      -4.001   2.310   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      -1.334   3.850   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       2.667   0.000   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       8.002  -0.000   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       5.335  -4.620   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   33                                                  
CONECT    3    2    4   16                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   14                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   10                                                  
CONECT    8    7    9                                                       
CONECT    9    8                                                            
CONECT   10    7   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12    5   15                                                  
CONECT   15   14                                                            
CONECT   16    3   17   25                                                  
CONECT   17   16   18   24                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   17                                                       
CONECT   25   16   26                                                       
CONECT   26   25   27   33                                                  
CONECT   27   26   28                                                       
CONECT   28   27   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   31                                                       
CONECT   31   30   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31    2   26                                                  
MASTER        0    0    0    0    0    0    0    0   33    0   72    0
END

View in JSmol

Synonyms

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

Chemical Formula

C₂₁H₂₀O₁₂

Average Mass

464.3790 Da

Monoisotopic Mass

464.09548 Da

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

OC[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](O)[C@H]1O

InChI Identifier

InChI=1S/C21H20O12/c22-6-13-15(27)17(29)18(30)21(32-13)33-20-16(28)14-11(26)4-8(23)5-12(14)31-19(20)7-1-2-9(24)10(25)3-7/h1-5,13,15,17-18,21-27,29-30H,6H2/t13-,15-,17+,18-,21+/m0/s1

InChI Key

OVSQVDMCBVZWGM-LQSBFMDOSA-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
Alnus japonica	LOTUS Database	35616633
Conyza filaginoides	LOTUS Database	35616633
Corchorus olitorius	LOTUS Database	35616633
Eucalyptus viminalis	LOTUS Database	35616633
Geranium collinum	LOTUS Database	35616633
Hippophae rhamnoides	LOTUS Database	35616633
Leonurus marrubiastrum	LOTUS Database	35616633
Lepisorus contortus	LOTUS Database	35616633
Rheum rhaponticum	LOTUS Database	35616633
Rhododendron dauricum	LOTUS Database	35616633
Solidago canadensis	LOTUS Database	35616633
Sorbus tianschanica	LOTUS Database	35616633
Stylosanthes erecta	LOTUS Database	35616633
Trifolium arvense	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
Hydroxyflavonoid
3'-hydroxyflavonoid
4'-hydroxyflavonoid
5-hydroxyflavonoid
7-hydroxyflavonoid
Flavone
Hexose monosaccharide
Chromone
Glycosyl compound
O-glycosyl compound
Benzopyran
1-benzopyran
Catechol
1-hydroxy-2-unsubstituted benzenoid
Phenol
Pyranone
1-hydroxy-4-unsubstituted benzenoid
Monocyclic benzene moiety
Benzenoid
Pyran
Monosaccharide
Oxane
Vinylogous acid
Heteroaromatic compound
Secondary alcohol
Organoheterocyclic compound
Oxacycle
Polyol
Acetal
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Alcohol
Primary alcohol
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	-0.14	ChemAxon
pKa (Strongest Acidic)	6.37	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	4	ChemAxon
Refractivity	109.28 m³·mol⁻¹	ChemAxon
Polarizability	43.07 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

8989274

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Isoquercetin

METLIN ID

Not Available

PubChem Compound

10813969

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Xie J, Zhao J, Zhang N, Xu H, Yang J, Ye J, Jiang J: Efficient production of isoquercitin, icariin and icariside II by a novel thermostable alpha-l-rhamnosidase PodoRha from Paenibacillus odorifer with high alpha-1, 6-/alpha-1, 2- glycoside specificity. Enzyme Microb Technol. 2022 Aug;158:110039. doi: 10.1016/j.enzmictec.2022.110039. Epub 2022 Apr 7. [PubMed:35472682 ]
Shi Y, Yang L, Yu M, Li Z, Ke Z, Qian X, Ruan X, He L, Wei F, Zhao Y, Wang Q: Seasonal variation influences flavonoid biosynthesis path and content, and antioxidant activity of metabolites in Tetrastigma hemsleyanum Diels & Gilg. PLoS One. 2022 Apr 28;17(4):e0265954. doi: 10.1371/journal.pone.0265954. eCollection 2022. [PubMed:35482747 ]
Zekeya N, Ibrahim M, Mamiro B, Ndossi H, Kilonzo M, Mkangara M, Chacha M, Chilongola J, Kideghesho J: Potential of natural phenolic antioxidant compounds from Bersama abyssinica (Meliathacea) for treatment of chronic diseases. Saudi J Biol Sci. 2022 Jun;29(6):103273. doi: 10.1016/j.sjbs.2022.03.023. Epub 2022 Mar 23. [PubMed:35431593 ]
Lee EH, Park HJ, Kim HH, Jung HY, Kang IK, Cho YJ: Isolated isoquercitrin from Green ball apple peel inhibits photoaging in CCD-986Sk fibroblasts cells via modulation of the MMPs signaling. J Cosmet Dermatol. 2021 Sep;20(9):2932-2939. doi: 10.1111/jocd.13903. Epub 2021 Jan 15. [PubMed:33356000 ]
Chestnut C, Subramaniam D, Dandawate P, Padhye S, Taylor J 3rd, Weir S, Anant S: Targeting Major Signaling Pathways of Bladder Cancer with Phytochemicals: A Review. Nutr Cancer. 2021;73(11-12):2249-2271. doi: 10.1080/01635581.2020.1856895. Epub 2020 Dec 11. [PubMed:33305598 ]
Zagrean-Tuza C, Mot AC, Chmiel T, Bende A, Turcu I: Sugar matters: sugar moieties as reactivity-tuning factors in quercetin O-glycosides. Food Funct. 2020 Jun 24;11(6):5293-5307. doi: 10.1039/d0fo00319k. [PubMed:32458896 ]
Li J, Yang X, Li X, Zhang Z, Wei Z, Xing Z, Deng S, Duan F: Okra polysaccharides/gelatin complex coacervate as pH-responsive and intestine-targeting delivery protects isoquercitin bioactivity. Int J Biol Macromol. 2020 Sep 15;159:487-496. doi: 10.1016/j.ijbiomac.2020.05.067. Epub 2020 May 15. [PubMed:32422271 ]
Kazzem M, Sun YT, Low M, Seto SW, Chang D, Lee S, Suresh H, Khoo CS, Bensoussan A, Kiat H: Chromatographic Analysis and Anti-Oxidative Property of Naoxinqing Tablet, a Proprietary Preparation of Diospyros Kaki Leaves. Molecules. 2019 Mar 20;24(6):1101. doi: 10.3390/molecules24061101. [PubMed:30897753 ]
Orfali Gd, Duarte AC, Bonadio V, Martinez NP, de Araujo ME, Priviero FB, Carvalho PO, Priolli DG: Review of anticancer mechanisms of isoquercitin. World J Clin Oncol. 2016 Apr 10;7(2):189-99. doi: 10.5306/wjco.v7.i2.189. [PubMed:27081641 ]
Sahreen S, Khan MR, Khan RA, Shah NA: Effect of Carissa opaca leaves extract on lipid peroxidation, antioxidant activity and reproductive hormones in male rats. Lipids Health Dis. 2013 Jun 20;12:90. doi: 10.1186/1476-511X-12-90. [PubMed:23786717 ]
LOTUS database [Link]

Showing NP-Card for 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-{[(2r,3s,4r,5r,6s)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}chromen-4-one (NP0223638)

MOL for NP0223638 (2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-{[(2r,3s,4r,5r,6s)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}chromen-4-one)

3D MOL for NP0223638 (2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-{[(2r,3s,4r,5r,6s)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}chromen-4-one)

3D SDF for NP0223638 (2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-{[(2r,3s,4r,5r,6s)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}chromen-4-one)

3D-SDF for NP0223638 (2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-{[(2r,3s,4r,5r,6s)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}chromen-4-one)

PDB for NP0223638 (2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-{[(2r,3s,4r,5r,6s)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}chromen-4-one)

3D PDB for NP0223638 (2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-{[(2r,3s,4r,5r,6s)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}chromen-4-one)

SMILES for NP0223638 (2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-{[(2r,3s,4r,5r,6s)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}chromen-4-one)

INCHI for NP0223638 (2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-{[(2r,3s,4r,5r,6s)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}chromen-4-one)

Structure for NP0223638 (2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-{[(2r,3s,4r,5r,6s)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}chromen-4-one)

3D Structure for NP0223638 (2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-{[(2r,3s,4r,5r,6s)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}chromen-4-one)