NP-MRD: Showing NP-Card for 3-(3,4-Dihydroxyphenyl)-1-(3-beta-D-glucopyranosyl-2,4,6-trihydroxyphenyl)-1-propanone (NP0054044)

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Record Information

Version

2.0

Created at

2022-04-28 00:31:24 UTC

Updated at

2022-04-28 00:31:24 UTC

NP-MRD ID

NP0054044

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3-(3,4-Dihydroxyphenyl)-1-(3-beta-D-glucopyranosyl-2,4,6-trihydroxyphenyl)-1-propanone

Description

Aspalathin belongs to the class of organic compounds known as 2'-hydroxy-dihydrochalcones. These are organic compounds containing dihydrochalcone skeleton that carries a hydroxyl group at the 2'-position. Aspalathin 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. 3-(3,4-Dihydroxyphenyl)-1-(3-beta-D-glucopyranosyl-2,4,6-trihydroxyphenyl)-1-propanone is found in Aspalathus linearis . 3-(3,4-Dihydroxyphenyl)-1-(3-beta-D-glucopyranosyl-2,4,6-trihydroxyphenyl)-1-propanone was first documented in 2021 (PMID: 34685955). Based on a literature review a small amount of articles have been published on aspalathin (PMID: 35008779) (PMID: 34834822) (PMID: 34684871).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282202312D          

 32 34  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   -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  0  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
    0.0000   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -6.6000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -7.4250    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
    2.1434   -1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8579   -0.0000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -1.2375    0.0000 O   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
    2.8579    0.8250    0.0000 O   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
    0.7145   -0.4125    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
  5  7  1  0  0  0  0
  4  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 12 17  1  0  0  0  0
 15 18  1  0  0  0  0
 14 19  1  0  0  0  0
  3 20  1  0  0  0  0
 21  2  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  1  0  0  0  0
 24 29  1  6  0  0  0
 23 30  1  1  0  0  0
 22 31  1  6  0  0  0
  1 32  1  0  0  0  0
M  END

     RDKit          3D

 56 58  0  0  0  0  0  0  0  0999 V2000
    3.0754   -0.8736    1.7054 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0634   -0.1945    1.3083 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2035    1.2190    0.9930 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5345    1.8488    1.1953 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6530    1.3021    0.4303 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5624    0.4490    1.0165 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6450   -0.0655    0.3564 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8700    0.2668   -0.9683 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9756   -0.2791   -1.5876 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9815    1.1096   -1.5625 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1878    1.4612   -2.9010 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8855    1.6296   -0.8931 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7915   -0.9120    1.1950 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7823   -2.2443    1.5139 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9348   -2.9113    1.9349 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3921   -2.9741    1.4241 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5510   -2.3658    1.0162 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6807   -3.1729    0.9534 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5833   -1.0129    0.6842 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8821   -0.5102    0.2484 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.1630   -0.9492   -1.0529 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4754   -0.8718   -1.3889 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.6543   -0.6362   -2.8988 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0420    0.5512   -3.2793 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2928    0.0971   -0.6290 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.1293   -0.5866    0.2882 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5762    1.2152    0.0154 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.7983    2.4672   -0.5680 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0707    0.9760    0.2270 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.7180    1.5249    1.4775 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3986   -0.2807    0.7746 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3852    0.9763    0.4717 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4881    1.7765    1.6552 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8381    1.3867   -0.0636 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7784    1.7368    2.2908 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4376    2.9434    1.0243 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4446    0.1743    2.0688 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3274   -0.7335    0.8679 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2292   -0.1096   -2.5267 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9593    1.1192   -3.4369 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1972    2.2922   -1.3790 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8960   -3.8861    2.1610 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3813   -4.0160    1.6772 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5920   -2.8806    0.6691 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6513   -0.9025    0.9555 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9215   -1.9003   -1.2385 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2788   -1.5006   -3.4811 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7550   -0.5915   -3.0624 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7348    1.2685   -3.1727 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0368    0.5634   -1.3447 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0314   -1.5604    0.1616 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9934    1.3220    1.0601 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8150    3.1960    0.0967 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5072    1.4027   -0.6039 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8538    0.8154    2.1544 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3968    1.8307    0.2609 H   0  0  0  0  0  0  0  0  0  0  0  0
 24 23  1  0
 23 22  1  0
 22 21  1  0
 21 20  1  0
 20 29  1  0
 29 30  1  0
 29 27  1  0
 27 28  1  0
 27 25  1  0
 25 26  1  0
 20 19  1  0
 19 17  2  0
 17 18  1  0
 17 16  1  0
 16 14  2  0
 14 15  1  0
 14 13  1  0
 13  2  1  0
  2  1  2  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5 12  2  0
 12 10  1  0
 10 11  1  0
 10  8  2  0
  8  9  1  0
  8  7  1  0
  7  6  2  0
 13 31  2  0
 31 32  1  0
 25 22  1  0
 31 19  1  0
  6  5  1  0
 24 49  1  0
 23 47  1  0
 23 48  1  0
 22 46  1  6
 20 45  1  1
 29 54  1  6
 30 55  1  0
 27 52  1  1
 28 53  1  0
 25 50  1  6
 26 51  1  0
 18 44  1  0
 16 43  1  0
 15 42  1  0
  3 33  1  0
  3 34  1  0
  4 35  1  0
  4 36  1  0
 12 41  1  0
 11 40  1  0
  9 39  1  0
  7 38  1  0
  6 37  1  0
 32 56  1  0
M  END


  Mrv1652304282202312D          

 32 34  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   -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  0  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
    0.0000   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -6.6000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -7.4250    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
    2.1434   -1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8579   -0.0000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -1.2375    0.0000 O   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
    2.8579    0.8250    0.0000 O   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
    0.7145   -0.4125    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
  5  7  1  0  0  0  0
  4  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 12 17  1  0  0  0  0
 15 18  1  0  0  0  0
 14 19  1  0  0  0  0
  3 20  1  0  0  0  0
 21  2  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  1  0  0  0  0
 24 29  1  6  0  0  0
 23 30  1  1  0  0  0
 22 31  1  6  0  0  0
  1 32  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0054044

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC[C@H]1O[C@H]([C@H](O)[C@@H](O)[C@@H]1O)C1=C(O)C=C(O)C(C(=O)CCC2=CC(O)=C(O)C=C2)=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C21H24O11/c22-7-14-17(28)19(30)20(31)21(32-14)16-13(27)6-12(26)15(18(16)29)10(24)4-2-8-1-3-9(23)11(25)5-8/h1,3,5-6,14,17,19-23,25-31H,2,4,7H2/t14-,17-,19+,20-,21+/m1/s1

> <INCHI_KEY>
VCPUQYKWJRESOC-VJXVFPJBSA-N

> <FORMULA>
C21H24O11

> <MOLECULAR_WEIGHT>
452.412

> <EXACT_MASS>
452.131861593

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_ATOM_COUNT>
56

> <JCHEM_AVERAGE_POLARIZABILITY>
43.6187857499225

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
9

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-(3,4-dihydroxyphenyl)-1-{2,4,6-trihydroxy-3-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]phenyl}propan-1-one

> <ALOGPS_LOGP>
0.03

> <JCHEM_LOGP>
0.8346543059999996

> <ALOGPS_LOGS>
-2.26

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.044301906180667

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.538555145957981

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6447308917779946

> <JCHEM_POLAR_SURFACE_AREA>
208.36999999999998

> <JCHEM_REFRACTIVITY>
108.8065

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.49e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-(3,4-dihydroxyphenyl)-1-{2,4,6-trihydroxy-3-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]phenyl}propan-1-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         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  O   UNK     0      -1.334  -5.390   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       2.667  -7.700   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  C   UNK     0      -0.000  -9.240   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.334 -10.010   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.334 -11.550   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -2.667 -12.320   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -4.001 -11.550   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -4.001 -10.010   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -2.667  -9.240   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -5.335 -12.320   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      -2.667 -13.860   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       4.001  -5.390   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       5.335  -0.000   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       5.335  -3.080   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       8.002  -3.080   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       9.336  -2.310   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0       8.002  -0.000   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0       5.335   1.540   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0       2.667   0.000   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0       1.334  -0.770   0.000  0.00  0.00           O+0
CONECT    1    2    6   32                                                  
CONECT    2    1    3   21                                                  
CONECT    3    2    4   20                                                  
CONECT    4    3    5    8                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5    1                                                       
CONECT    7    5                                                            
CONECT    8    4    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   17                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   19                                                  
CONECT   15   14   16   18                                                  
CONECT   16   15   17                                                       
CONECT   17   16   12                                                       
CONECT   18   15                                                            
CONECT   19   14                                                            
CONECT   20    3                                                            
CONECT   21    2   22   26                                                  
CONECT   22   21   23   31                                                  
CONECT   23   22   24   30                                                  
CONECT   24   23   25   29                                                  
CONECT   25   24   26   27                                                  
CONECT   26   25   21                                                       
CONECT   27   25   28                                                       
CONECT   28   27                                                            
CONECT   29   24                                                            
CONECT   30   23                                                            
CONECT   31   22                                                            
CONECT   32    1                                                            
MASTER        0    0    0    0    0    0    0    0   32    0   68    0
END

View in JSmol

Synonyms

Value	Source
1-(3-C-beta-D-Glucopyranosyl-2,4,6-trihydroxyphenyl)-3-(3,4-dihydroxyphenyl)-1-propanone	ChEBI
3-(3,4-Dihydroxyphenyl)-1-(3-beta-D-glucopyranosyl-2,4,6-trihydroxyphenyl)-1-propanone	ChEBI
3-(3,4-Dihydroxyphenyl)-3'-beta-D-glucopyranosyl-2',4',6'-trihydroxypropiophenone	ChEBI
1-(3-C-b-D-Glucopyranosyl-2,4,6-trihydroxyphenyl)-3-(3,4-dihydroxyphenyl)-1-propanone	Generator
1-(3-C-Β-D-glucopyranosyl-2,4,6-trihydroxyphenyl)-3-(3,4-dihydroxyphenyl)-1-propanone	Generator
3-(3,4-Dihydroxyphenyl)-1-(3-b-D-glucopyranosyl-2,4,6-trihydroxyphenyl)-1-propanone	Generator
3-(3,4-Dihydroxyphenyl)-1-(3-β-D-glucopyranosyl-2,4,6-trihydroxyphenyl)-1-propanone	Generator
3-(3,4-Dihydroxyphenyl)-3'-b-D-glucopyranosyl-2',4',6'-trihydroxypropiophenone	Generator
3-(3,4-Dihydroxyphenyl)-3'-β-D-glucopyranosyl-2',4',6'-trihydroxypropiophenone	Generator

Chemical Formula

C₂₁H₂₄O₁₁

Average Mass

452.4120 Da

Monoisotopic Mass

452.13186 Da

IUPAC Name

3-(3,4-dihydroxyphenyl)-1-{2,4,6-trihydroxy-3-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]phenyl}propan-1-one

Traditional Name

3-(3,4-dihydroxyphenyl)-1-{2,4,6-trihydroxy-3-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]phenyl}propan-1-one

CAS Registry Number

Not Available

SMILES

OC[C@H]1O[C@H]([C@H](O)[C@@H](O)[C@@H]1O)C1=C(O)C=C(O)C(C(=O)CCC2=CC(O)=C(O)C=C2)=C1O

InChI Identifier

InChI=1S/C21H24O11/c22-7-14-17(28)19(30)20(31)21(32-14)16-13(27)6-12(26)15(18(16)29)10(24)4-2-8-1-3-9(23)11(25)5-8/h1,3,5-6,14,17,19-23,25-31H,2,4,7H2/t14-,17-,19+,20-,21+/m1/s1

InChI Key

VCPUQYKWJRESOC-VJXVFPJBSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Aspalathus linearis	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 2'-hydroxy-dihydrochalcones. These are organic compounds containing dihydrochalcone skeleton that carries a hydroxyl group at the 2'-position.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Linear 1,3-diarylpropanoids

Sub Class

Chalcones and dihydrochalcones

Direct Parent

2'-Hydroxy-dihydrochalcones

Alternative Parents

Substituents

2'-hydroxy-dihydrochalcone
Phenolic glycoside
Cinnamylphenol
Alkyl-phenylketone
Hexose monosaccharide
Glycosyl compound
Acylphloroglucinol derivative
C-glycosyl compound
Butyrophenone
Phloroglucinol derivative
Phenylketone
Benzenetriol
Aryl ketone
Catechol
Aryl alkyl ketone
Benzoyl
1-hydroxy-4-unsubstituted benzenoid
Phenol
1-hydroxy-2-unsubstituted benzenoid
Benzenoid
Monosaccharide
Monocyclic benzene moiety
Oxane
Vinylogous acid
Ketone
Secondary alcohol
Oxacycle
Organoheterocyclic compound
Polyol
Dialkyl ether
Ether
Alcohol
Organic oxygen compound
Primary alcohol
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

polyphenol (CHEBI:79078 )
polyketide (CHEBI:79078 )
C-glycosyl compound (CHEBI:79078 )
catechol (CHEBI:79078 )
dihydrochalcones (CHEBI:79078 )

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	0.03	ALOGPS
logP	0.83	ChemAxon
logS	-2.3	ALOGPS
pKa (Strongest Acidic)	7.54	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	9	ChemAxon
Polar Surface Area	208.37 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	108.81 m³·mol⁻¹	ChemAxon
Polarizability	43.62 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00006096

Chemspider ID

9457391

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Aspalathin

METLIN ID

Not Available

PubChem Compound

11282394

PDB ID

Not Available

ChEBI ID

79078

Good Scents ID

Not Available

References

General References

Kostikova VA, Chernonosov AA, Kuznetsov AA, Petrova NV, Krivenko DA, Chernysheva OA, Wang W, Erst AS: Identification of Flavonoids in the Leaves of Eranthis longistipitata (Ranunculaceae) by Liquid Chromatography with High-Resolution Mass Spectrometry (LC-HRMS). Plants (Basel). 2021 Oct 10;10(10). pii: plants10102146. doi: 10.3390/plants10102146. [PubMed:34685955 ]
Muller CJF, Joubert E, Chellan N, Miura Y, Yagasaki K: New Insights into the Efficacy of Aspalathin and Other Related Phytochemicals in Type 2 Diabetes-A Review. Int J Mol Sci. 2021 Dec 29;23(1):356. doi: 10.3390/ijms23010356. [PubMed:35008779 ]
Akinfenwa AO, Abdul NS, Docrat FT, Marnewick JL, Luckay RC, Hussein AA: Cytotoxic Effects of Phytomediated Silver and Gold Nanoparticles Synthesised from Rooibos (Aspalathus linearis), and Aspalathin. Plants (Basel). 2021 Nov 15;10(11):2460. doi: 10.3390/plants10112460. [PubMed:34834822 ]
Mthembu SXH, Muller CJF, Dludla PV, Madoroba E, Kappo AP, Mazibuko-Mbeje SE: Rooibos Flavonoids, Aspalathin, Isoorientin, and Orientin Ameliorate Antimycin A-Induced Mitochondrial Dysfunction by Improving Mitochondrial Bioenergetics in Cultured Skeletal Muscle Cells. Molecules. 2021 Oct 18;26(20):6289. doi: 10.3390/molecules26206289. [PubMed:34684871 ]

Showing NP-Card for 3-(3,4-Dihydroxyphenyl)-1-(3-beta-D-glucopyranosyl-2,4,6-trihydroxyphenyl)-1-propanone (NP0054044)

MOL for NP0054044 (3-(3,4-Dihydroxyphenyl)-1-(3-beta-D-glucopyranosyl-2,4,6-trihydroxyphenyl)-1-propanone)

3D MOL for NP0054044 (3-(3,4-Dihydroxyphenyl)-1-(3-beta-D-glucopyranosyl-2,4,6-trihydroxyphenyl)-1-propanone)

3D SDF for NP0054044 (3-(3,4-Dihydroxyphenyl)-1-(3-beta-D-glucopyranosyl-2,4,6-trihydroxyphenyl)-1-propanone)

3D-SDF for NP0054044 (3-(3,4-Dihydroxyphenyl)-1-(3-beta-D-glucopyranosyl-2,4,6-trihydroxyphenyl)-1-propanone)

PDB for NP0054044 (3-(3,4-Dihydroxyphenyl)-1-(3-beta-D-glucopyranosyl-2,4,6-trihydroxyphenyl)-1-propanone)

3D PDB for NP0054044 (3-(3,4-Dihydroxyphenyl)-1-(3-beta-D-glucopyranosyl-2,4,6-trihydroxyphenyl)-1-propanone)

SMILES for NP0054044 (3-(3,4-Dihydroxyphenyl)-1-(3-beta-D-glucopyranosyl-2,4,6-trihydroxyphenyl)-1-propanone)

INCHI for NP0054044 (3-(3,4-Dihydroxyphenyl)-1-(3-beta-D-glucopyranosyl-2,4,6-trihydroxyphenyl)-1-propanone)

Structure for NP0054044 (3-(3,4-Dihydroxyphenyl)-1-(3-beta-D-glucopyranosyl-2,4,6-trihydroxyphenyl)-1-propanone)

3D Structure for NP0054044 (3-(3,4-Dihydroxyphenyl)-1-(3-beta-D-glucopyranosyl-2,4,6-trihydroxyphenyl)-1-propanone)