NP-MRD: Showing NP-Card for 5-hydroxy-3-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2-(3,4,5-trihydroxyphenyl)chromen-7-one (NP0192235)

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Record Information

Version

2.0

Created at

2022-09-04 09:23:43 UTC

Updated at

2022-09-04 09:23:43 UTC

NP-MRD ID

NP0192235

Secondary Accession Numbers

None

Natural Product Identification

Common Name

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

Description

CHEBI:144776 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. 5-hydroxy-3-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2-(3,4,5-trihydroxyphenyl)chromen-7-one is found in Berberis integerrima, Camellia sinensis, Dacrycarpus dacrydioides, Geranium sylvaticum, Hibiscus syriacus, Malvaviscus arboreus, Penstemon serrulatus, Petunia hybrida, Phaseolus vulgaris, Pistacia lentiscus, Ribes nigrum, Vaccinium arboreum, Vaccinium corymbosum, Vaccinium myrtillus, Vaccinium oxycoccos, Vigna unguiculata and Vitis vinifera. Based on a literature review very few articles have been published on CHEBI:144776.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309042211232D          

 33 36  0  0  1  0            999 V2000
    0.0000    0.0000    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
    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 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
    4.2868   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -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
    4.2868   -2.4750    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.0013   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -3.7125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.7158   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.1250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.2868   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -3.7125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8579   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.8875    0.0000 C   0  0  1  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
    2.8579   -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 C   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
    0.7145   -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  2  0  0  0  0
  4  5  1  0  0  0  0
  5  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  1  0  0  0  0
  9 11  2  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  2  0  0  0  0
  7 15  1  0  0  0  0
  6 16  2  0  0  0  0
 16 17  1  0  0  0  0
 18 17  1  6  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  6  0  0  0
 21 22  1  0  0  0  0
 20 23  1  0  0  0  0
 23 24  1  1  0  0  0
 23 25  1  0  0  0  0
 25 26  1  6  0  0  0
 25 27  1  0  0  0  0
 18 27  1  0  0  0  0
 27 28  1  1  0  0  0
 16 29  1  0  0  0  0
 29 30  2  0  0  0  0
  4 30  1  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
M  END

     RDKit          3D

 53 56  0  0  0  0  0  0  0  0999 V2000
    5.3966    4.5969   -1.8399 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3368    3.9107   -1.7047 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3188    2.9130   -0.7591 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1550    2.1557   -0.6070 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0670    1.2048    0.2595 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9913    0.4465    0.4559 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1052   -0.5763    1.4903 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3146   -0.6812    2.1882 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5003   -1.6099    3.1678 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7256   -1.6680    3.8290 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5154   -2.4933    3.5259 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7571   -3.4237    4.5349 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3169   -2.4271    2.8703 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3028   -3.3028    3.2064 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1414   -1.4643    1.8631 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8529    0.6239   -0.2738 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2510   -0.1250   -0.1001 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4963   -0.1223   -0.7151 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.4481    0.0468    0.2962 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7061    0.0396   -0.2510 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.7809    0.5179    0.6634 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4735    1.8385    1.0244 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9867   -1.3987   -0.7009 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.3209   -1.5844   -1.0197 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0773   -1.6032   -1.9145 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.2998   -2.8197   -2.4989 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6594   -1.4784   -1.3891 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7281   -1.5261   -2.4193 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8666    1.6456   -1.2444 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9865    2.4214   -1.4359 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0525    3.4216   -2.3603 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9774    3.7137   -3.1684 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2321    4.1616   -2.4881 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1748    2.6814   -0.1165 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1192    0.0108    1.9240 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4823   -1.0371    3.5996 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0491   -4.0873    4.8194 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5697   -3.2250    2.7006 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1886   -1.4466    1.3751 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5673    0.6450   -1.4858 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7050    0.6946   -1.1488 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7341    0.5476    0.0902 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9050   -0.0905    1.5720 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0917    2.2634    0.1931 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6352   -2.0791    0.0766 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8142   -1.8103   -0.1788 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2661   -0.7415   -2.6131 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1851   -3.1954   -2.2429 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5116   -2.2518   -0.6221 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0609   -2.2253   -2.2245 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0131    1.7988   -1.8236 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0999    3.2448   -3.1515 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2606    4.9497   -3.2279 H   0  0  0  0  0  0  0  0  0  0  0  0
 22 21  1  0
 21 20  1  0
 20 19  1  0
 19 18  1  0
 18 17  1  0
 17 16  1  0
 16  6  2  0
  6  5  1  0
  5  4  1  0
  4  3  2  0
  3  2  1  0
  2  1  2  0
  2 33  1  0
 33 31  2  0
 31 32  1  0
 31 30  1  0
 30 29  2  0
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  9 10  1  0
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 11 12  1  0
 11 13  1  0
 13 14  1  0
 13 15  2  0
 18 27  1  0
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 27 25  1  0
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 25 23  1  0
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 23 20  1  0
 29 16  1  0
 15  7  1  0
 30  4  1  0
 22 44  1  0
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 20 41  1  6
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  3 34  1  0
 33 53  1  0
 32 52  1  0
 29 51  1  0
  8 35  1  0
 10 36  1  0
 12 37  1  0
 14 38  1  0
 15 39  1  0
 27 49  1  1
 28 50  1  0
 25 47  1  6
 26 48  1  0
 23 45  1  1
 24 46  1  0
M  END


  Mrv1652309042211232D          

 33 36  0  0  1  0            999 V2000
    0.0000    0.0000    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
    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 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
    4.2868   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -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
    4.2868   -2.4750    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.0013   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -3.7125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.7158   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.1250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.2868   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -3.7125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8579   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.8875    0.0000 C   0  0  1  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
    2.8579   -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 C   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
    0.7145   -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  2  0  0  0  0
  4  5  1  0  0  0  0
  5  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  1  0  0  0  0
  9 11  2  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  2  0  0  0  0
  7 15  1  0  0  0  0
  6 16  2  0  0  0  0
 16 17  1  0  0  0  0
 18 17  1  6  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  6  0  0  0
 21 22  1  0  0  0  0
 20 23  1  0  0  0  0
 23 24  1  1  0  0  0
 23 25  1  0  0  0  0
 25 26  1  6  0  0  0
 25 27  1  0  0  0  0
 18 27  1  0  0  0  0
 27 28  1  1  0  0  0
 16 29  1  0  0  0  0
 29 30  2  0  0  0  0
  4 30  1  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
M  END
> <DATABASE_ID>
NP0192235

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC[C@H]1O[C@@H](OC2=C(OC3=CC(=O)C=C(O)C3=C2)C2=CC(O)=C(O)C(O)=C2)[C@H](O)[C@@H](O)[C@@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C21H20O12/c22-6-15-17(28)18(29)19(30)21(33-15)32-14-5-9-10(24)3-8(23)4-13(9)31-20(14)7-1-11(25)16(27)12(26)2-7/h1-5,15,17-19,21-22,24-30H,6H2/t15-,17-,18+,19-,21-/m1/s1

> <INCHI_KEY>
XIIACXXCJBZLHS-PEVLUNPASA-N

> <FORMULA>
C21H20O12

> <MOLECULAR_WEIGHT>
464.379

> <EXACT_MASS>
464.095476084

> <JCHEM_ACCEPTOR_COUNT>
12

> <JCHEM_ATOM_COUNT>
53

> <JCHEM_AVERAGE_POLARIZABILITY>
43.3913148427349

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
8

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <JCHEM_LOGP>
-1.7399104739999998

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.188011171650116

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.3902740605692125

> <JCHEM_PKA_STRONGEST_BASIC>
2.701632000076093

> <JCHEM_POLAR_SURFACE_AREA>
206.6

> <JCHEM_REFRACTIVITY>
113.26230000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
5-hydroxy-3-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2-(3,4,5-trihydroxyphenyl)chromen-7-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-22         0                                  
HETATM    1  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       5.335   0.000   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       8.002  -0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.336   2.310   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       9.336   3.850   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      10.669   1.540   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      12.003   2.310   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      10.669  -0.000   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      12.003  -0.770   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       9.336  -0.770   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       8.002  -3.080   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       8.002  -4.620   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       9.336  -5.390   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       9.336  -6.930   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      10.669  -7.700   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      12.003  -6.930   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       8.002  -7.700   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       8.002  -9.240   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       6.668  -6.930   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       5.335  -7.700   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       6.668  -5.390   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       5.335  -4.620   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   33                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   30                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7   16                                                  
CONECT    7    6    8   15                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13    7                                                       
CONECT   16    6   17   29                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   27                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21   23                                                  
CONECT   21   20   22                                                       
CONECT   22   21                                                            
CONECT   23   20   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   18   28                                                  
CONECT   28   27                                                            
CONECT   29   16   30                                                       
CONECT   30   29    4   31                                                  
CONECT   31   30   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31    2                                                       
MASTER        0    0    0    0    0    0    0    0   33    0   72    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₁H₂₀O₁₂

Average Mass

464.3790 Da

Monoisotopic Mass

464.09548 Da

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

OC[C@H]1O[C@@H](OC2=C(OC3=CC(=O)C=C(O)C3=C2)C2=CC(O)=C(O)C(O)=C2)[C@H](O)[C@@H](O)[C@@H]1O

InChI Identifier

InChI=1S/C21H20O12/c22-6-15-17(28)18(29)19(30)21(33-15)32-14-5-9-10(24)3-8(23)4-13(9)31-20(14)7-1-11(25)16(27)12(26)2-7/h1-5,15,17-19,21-22,24-30H,6H2/t15-,17-,18+,19-,21-/m1/s1

InChI Key

XIIACXXCJBZLHS-PEVLUNPASA-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
Berberis integerrima	LOTUS Database	35616633
Camellia sinensis	LOTUS Database	35616633
Dacrycarpus dacrydioides	LOTUS Database	35616633
Geranium sylvaticum	LOTUS Database	35616633
Hibiscus syriacus	LOTUS Database	35616633
Malvaviscus arboreus	LOTUS Database	35616633
Penstemon serrulatus	LOTUS Database	35616633
Petunia hybrida	LOTUS Database	35616633
Phaseolus vulgaris	LOTUS Database	35616633
Pistacia lentiscus	LOTUS Database	35616633
Ribes nigrum	LOTUS Database	35616633
Vaccinium arboreum	LOTUS Database	35616633
Vaccinium corymbosum	LOTUS Database	35616633
Vaccinium myrtillus	LOTUS Database	35616633
Vaccinium oxycoccos	LOTUS Database	35616633
Vigna unguiculata	LOTUS Database	35616633
Vitis vinifera	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
Hydroxyflavonoid
Hexose monosaccharide
Glycosyl compound
O-glycosyl compound
Benzopyran
1-benzopyran
Benzenetriol
Pyrogallol derivative
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Monosaccharide
Benzenoid
Monocyclic benzene moiety
Oxane
Heteroaromatic compound
Vinylogous acid
Secondary alcohol
Cyclic ketone
Organoheterocyclic compound
Oxacycle
Acetal
Polyol
Primary alcohol
Organic oxide
Organic oxygen compound
Alcohol
Hydrocarbon derivative
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

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

Predicted Properties

Property	Value	Source
logP	-1.7	ChemAxon
pKa (Strongest Acidic)	7.39	ChemAxon
pKa (Strongest Basic)	2.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	12	ChemAxon
Hydrogen Donor Count	8	ChemAxon
Polar Surface Area	206.6 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	113.26 m³·mol⁻¹	ChemAxon
Polarizability	43.39 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

165559

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 5-hydroxy-3-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2-(3,4,5-trihydroxyphenyl)chromen-7-one (NP0192235)

MOL for NP0192235 (5-hydroxy-3-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2-(3,4,5-trihydroxyphenyl)chromen-7-one)

3D MOL for NP0192235 (5-hydroxy-3-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2-(3,4,5-trihydroxyphenyl)chromen-7-one)

3D SDF for NP0192235 (5-hydroxy-3-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2-(3,4,5-trihydroxyphenyl)chromen-7-one)

3D-SDF for NP0192235 (5-hydroxy-3-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2-(3,4,5-trihydroxyphenyl)chromen-7-one)

PDB for NP0192235 (5-hydroxy-3-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2-(3,4,5-trihydroxyphenyl)chromen-7-one)

3D PDB for NP0192235 (5-hydroxy-3-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2-(3,4,5-trihydroxyphenyl)chromen-7-one)

SMILES for NP0192235 (5-hydroxy-3-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2-(3,4,5-trihydroxyphenyl)chromen-7-one)

INCHI for NP0192235 (5-hydroxy-3-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2-(3,4,5-trihydroxyphenyl)chromen-7-one)

Structure for NP0192235 (5-hydroxy-3-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2-(3,4,5-trihydroxyphenyl)chromen-7-one)

3D Structure for NP0192235 (5-hydroxy-3-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2-(3,4,5-trihydroxyphenyl)chromen-7-one)