NP-MRD: Showing NP-Card for 5-hydroxy-2-(4-methoxyphenyl)-7-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}chromen-4-one (NP0224544)

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Record Information

Version

2.0

Created at

2022-09-06 02:55:50 UTC

Updated at

2022-09-06 02:55:50 UTC

NP-MRD ID

NP0224544

Secondary Accession Numbers

None

Natural Product Identification

Common Name

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

Description

5-hydroxy-2-(4-methoxyphenyl)-7-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}chromen-4-one is found in Agastache rugosa, Artemisia monosperma, Artemisia rupestris, Ballota acetabulosa, Betula pendula, Carduus nutans, Chrysanthemum morifolium, Dracocephalum tanguticum, Ficus lyrata, Kaempferia parviflora, Lawsonia inermis, Linaria kurdica, Lupinus polyphyllus, Nardostachys jatamansi, Phlomis aurea, Ramirezella strobilophora, Salvia pratensis, Tanacetum vulgare, Veratrum dahuricum and Verbascum sinaiticum.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533007131513432D          

 37 40  0  0  1  0            999 V2000
    7.8592   -1.2375    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
    5.7158   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -0.4125    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   -0.4125    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
   -0.7145   -2.8875    0.0000 C   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
    6.4302   -1.2375    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    1.2375    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    0.0000    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
    0.0000   -2.4750    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   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 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  2  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    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    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
    2.1434   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -1.6500    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
    3.5724   -0.4125    0.0000 O   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   -3.3000    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -3.3000    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.0625    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.0625    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.8250    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  4  2  1  0  0  0  0
  5  3  2  0  0  0  0
 10  2  2  0  0  0  0
 10  3  1  0  0  0  0
 11  4  2  0  0  0  0
 11  5  1  0  0  0  0
 12  6  2  0  0  0  0
 12  7  1  0  0  0  0
 13  6  1  0  0  0  0
 14  8  1  0  0  0  0
 15  8  2  0  0  0  0
 15 10  1  0  0  0  0
 16  7  2  0  0  0  0
 17  9  1  1  0  0  0
 18 13  2  0  0  0  0
 18 14  1  0  0  0  0
 18 16  1  0  0  0  0
 19 17  1  0  0  0  0
 20 19  1  0  0  0  0
 21 20  1  0  0  0  0
 22 21  1  0  0  0  0
 23  9  1  0  0  0  0
 24 13  1  0  0  0  0
 25 14  2  0  0  0  0
 19 26  1  6  0  0  0
 20 27  1  6  0  0  0
 21 28  1  6  0  0  0
 29  1  1  0  0  0  0
 29 11  1  0  0  0  0
 30 12  1  0  0  0  0
 22 30  1  1  0  0  0
 31 15  1  0  0  0  0
 31 16  1  0  0  0  0
 32 17  1  0  0  0  0
 32 22  1  0  0  0  0
 17 33  1  6  0  0  0
 19 34  1  1  0  0  0
 20 35  1  6  0  0  0
 21 36  1  1  0  0  0
 22 37  1  6  0  0  0
M  END

     RDKit          3D

 54 57  0  0  0  0  0  0  0  0999 V2000
    9.6524    1.3884    0.6544 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4355    2.1105    0.7082 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2548    1.3952    0.5652 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0499    2.1059    0.6177 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8784    1.4006    0.4763 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8222    0.0275    0.2852 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5546   -0.6740    0.1398 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4205   -2.0220   -0.0565 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1945   -2.6699   -0.1935 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1320   -3.8964   -0.3700 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0597   -1.9207   -0.1287 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2069   -2.4925   -0.2565 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4360   -3.8210   -0.4535 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3020   -1.6034   -0.1706 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1829   -0.2613    0.0245 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2578    0.5881    0.1054 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6028    0.2321    0.0022 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.1943    0.9463   -1.0760 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3883    0.2852   -1.3929 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.9378    0.7485   -2.7013 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1270    0.0393   -2.9362 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3743    0.6005   -0.2841 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.9637   -0.5545    0.2258 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6514    1.3284    0.8508 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.4319    2.6560    0.5067 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3808    0.6599    1.2485 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.5813   -0.4332    2.0895 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1154    0.2395    0.1435 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2354   -0.5564    0.0716 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4243   -0.0011    0.1940 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0224   -0.6347    0.2394 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2377    0.0365    0.3775 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8782    1.0581   -0.3773 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.6608    0.5113    1.3158 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.4480    2.0885    1.0365 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0834    3.1762    0.7662 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9392    1.9233    0.5125 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3013   -2.6399   -0.1125 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1835   -4.5452   -0.5327 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2766   -2.0922   -0.2756 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7713   -0.8483   -0.1593 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1841   -0.7873   -1.4131 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1975    1.8095   -2.7133 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2395    0.5144   -3.5329 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0289   -0.5641   -3.7136 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1786    1.2824   -0.6183 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7953   -0.2484    0.7098 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3451    1.2839    1.7175 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6133    2.7525   -0.4568 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7386    1.3656    1.7929 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0122   -0.3945    2.9007 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1994    1.3041    0.2989 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0459   -1.7010    0.0936 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1706   -0.4962    0.3398 H   0  0  0  0  0  0  0  0  0  0  0  0
 19 20  1  0
 20 21  1  0
 19 18  1  0
 18 17  1  0
 17 16  1  0
 16 15  1  0
 15 14  2  0
 14 12  1  0
 12 13  1  0
 12 11  2  0
 11  9  1  0
  9 10  2  0
  9  8  1  0
  8  7  2  0
  7 30  1  0
 30 29  1  0
 29 28  2  0
  7  6  1  0
  6  5  2  0
  5  4  1  0
  4  3  2  0
  3  2  1  0
  2  1  1  0
  3 32  1  0
 32 31  2  0
 17 26  1  0
 26 27  1  0
 26 24  1  0
 24 25  1  0
 24 22  1  0
 22 23  1  0
 22 19  1  0
 28 15  1  0
 31  6  1  0
 29 11  1  0
 19 42  1  6
 20 43  1  0
 20 44  1  0
 21 45  1  0
 17 41  1  6
 14 40  1  0
 13 39  1  0
  8 38  1  0
 28 52  1  0
  5 37  1  0
  4 36  1  0
  1 33  1  0
  1 34  1  0
  1 35  1  0
 32 54  1  0
 31 53  1  0
 26 50  1  1
 27 51  1  0
 24 48  1  1
 25 49  1  0
 22 46  1  6
 23 47  1  0
M  END


  Mrv1533007131513432D          

 37 40  0  0  1  0            999 V2000
    7.8592   -1.2375    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
    5.7158   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -0.4125    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   -0.4125    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
   -0.7145   -2.8875    0.0000 C   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
    6.4302   -1.2375    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    1.2375    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    0.0000    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
    0.0000   -2.4750    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   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 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  2  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    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    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
    2.1434   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -1.6500    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
    3.5724   -0.4125    0.0000 O   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   -3.3000    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -3.3000    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.0625    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.0625    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.8250    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  4  2  1  0  0  0  0
  5  3  2  0  0  0  0
 10  2  2  0  0  0  0
 10  3  1  0  0  0  0
 11  4  2  0  0  0  0
 11  5  1  0  0  0  0
 12  6  2  0  0  0  0
 12  7  1  0  0  0  0
 13  6  1  0  0  0  0
 14  8  1  0  0  0  0
 15  8  2  0  0  0  0
 15 10  1  0  0  0  0
 16  7  2  0  0  0  0
 17  9  1  1  0  0  0
 18 13  2  0  0  0  0
 18 14  1  0  0  0  0
 18 16  1  0  0  0  0
 19 17  1  0  0  0  0
 20 19  1  0  0  0  0
 21 20  1  0  0  0  0
 22 21  1  0  0  0  0
 23  9  1  0  0  0  0
 24 13  1  0  0  0  0
 25 14  2  0  0  0  0
 19 26  1  6  0  0  0
 20 27  1  6  0  0  0
 21 28  1  6  0  0  0
 29  1  1  0  0  0  0
 29 11  1  0  0  0  0
 30 12  1  0  0  0  0
 22 30  1  1  0  0  0
 31 15  1  0  0  0  0
 31 16  1  0  0  0  0
 32 17  1  0  0  0  0
 32 22  1  0  0  0  0
 17 33  1  6  0  0  0
 19 34  1  1  0  0  0
 20 35  1  6  0  0  0
 21 36  1  1  0  0  0
 22 37  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0224544

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@]1(CO)O[C@@]([H])(OC2=CC(O)=C3C(=O)C=C(OC3=C2)C2=CC=C(OC)C=C2)[C@]([H])(O)[C@@]([H])(O)[C@]1([H])O

> <INCHI_IDENTIFIER>
InChI=1S/C22H22O10/c1-29-11-4-2-10(3-5-11)15-8-14(25)18-13(24)6-12(7-16(18)31-15)30-22-21(28)20(27)19(26)17(9-23)32-22/h2-8,17,19-24,26-28H,9H2,1H3/t17-,19-,20+,21-,22-/m1/s1

> <INCHI_KEY>
NLZCOTZRUWYPTP-MIUGBVLSSA-N

> <FORMULA>
C22H22O10

> <MOLECULAR_WEIGHT>
446.408

> <EXACT_MASS>
446.121296908

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
54

> <JCHEM_AVERAGE_POLARIZABILITY>
44.15680524731964

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
0.72

> <JCHEM_LOGP>
0.5845150963333339

> <ALOGPS_LOGS>
-2.86

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.200113032927037

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.3142197967002165

> <JCHEM_PKA_STRONGEST_BASIC>
-2.981092343758667

> <JCHEM_POLAR_SURFACE_AREA>
155.14

> <JCHEM_REFRACTIVITY>
109.54059999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.18e-01 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 13-JUL-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   13-JUL-15         0                                  
HETATM    1  C   UNK     0      14.670  -2.310   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.336  -2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      10.669  -0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      10.669  -3.080   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      12.003  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.001  -0.770   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      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.336  -0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      12.003  -2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.001   2.310   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       8.002   0.000   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.667  -3.080   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  O   UNK     0      -1.334  -6.930   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       4.001   3.850   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0       6.668   3.850   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0       1.334  -6.930   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0       4.001  -5.390   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0       4.001  -2.310   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0      13.337  -3.080   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0       1.334  -0.770   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0       6.668  -0.770   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0       0.000  -3.080   0.000  0.00  0.00           O+0
HETATM   33  H   UNK     0       0.000  -6.160   0.000  0.00  0.00           H+0
HETATM   34  H   UNK     0       2.667  -6.160   0.000  0.00  0.00           H+0
HETATM   35  H   UNK     0       1.334  -3.850   0.000  0.00  0.00           H+0
HETATM   36  H   UNK     0       4.001  -3.850   0.000  0.00  0.00           H+0
HETATM   37  H   UNK     0       2.667  -1.540   0.000  0.00  0.00           H+0
CONECT    1   29                                                            
CONECT    2    4   10                                                       
CONECT    3    5   10                                                       
CONECT    4    2   11                                                       
CONECT    5    3   11                                                       
CONECT    6   12   13                                                       
CONECT    7   12   16                                                       
CONECT    8   14   15                                                       
CONECT    9   17   23                                                       
CONECT   10    2    3   15                                                  
CONECT   11    4    5   29                                                  
CONECT   12    6    7   30                                                  
CONECT   13    6   18   24                                                  
CONECT   14    8   18   25                                                  
CONECT   15    8   10   31                                                  
CONECT   16    7   18   31                                                  
CONECT   17    9   19   32   33                                             
CONECT   18   13   14   16                                                  
CONECT   19   17   20   26   34                                             
CONECT   20   19   21   27   35                                             
CONECT   21   20   22   28   36                                             
CONECT   22   21   30   32   37                                             
CONECT   23    9                                                            
CONECT   24   13                                                            
CONECT   25   14                                                            
CONECT   26   19                                                            
CONECT   27   20                                                            
CONECT   28   21                                                            
CONECT   29    1   11                                                       
CONECT   30   12   22                                                       
CONECT   31   15   16                                                       
CONECT   32   17   22                                                       
CONECT   33   17                                                            
CONECT   34   19                                                            
CONECT   35   20                                                            
CONECT   36   21                                                            
CONECT   37   22                                                            
MASTER        0    0    0    0    0    0    0    0   37    0   80    0
END

View in JSmol

Synonyms

Value	Source
Tilianin	ChEMBL

Chemical Formula

C₂₂H₂₂O₁₀

Average Mass

446.4080 Da

Monoisotopic Mass

446.12130 Da

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

[H][C@]1(CO)O[C@@]([H])(OC2=CC(O)=C3C(=O)C=C(OC3=C2)C2=CC=C(OC)C=C2)[C@]([H])(O)[C@@]([H])(O)[C@]1([H])O

InChI Identifier

InChI=1S/C22H22O10/c1-29-11-4-2-10(3-5-11)15-8-14(25)18-13(24)6-12(7-16(18)31-15)30-22-21(28)20(27)19(26)17(9-23)32-22/h2-8,17,19-24,26-28H,9H2,1H3/t17-,19-,20+,21-,22-/m1/s1

InChI Key

NLZCOTZRUWYPTP-MIUGBVLSSA-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
Agastache rugosa	LOTUS Database	35616633
Artemisia monosperma	LOTUS Database	35616633
Artemisia rupestris	LOTUS Database	35616633
Ballota acetabulosa	LOTUS Database	35616633
Betula pendula	LOTUS Database	35616633
Carduus nutans	LOTUS Database	35616633
Chrysanthemum morifolium	LOTUS Database	35616633
Dracocephalum tanguticum	LOTUS Database	35616633
Ficus lyrata	LOTUS Database	35616633
Kaempferia parviflora	LOTUS Database	35616633
Lawsonia inermis	LOTUS Database	35616633
Linaria kurdica	LOTUS Database	35616633
Lupinus polyphyllus	LOTUS Database	35616633
Nardostachys jatamansi	LOTUS Database	35616633
Phlomis aurea	LOTUS Database	35616633
Ramirezella strobilophora	LOTUS Database	35616633
Salvia pratensis	LOTUS Database	35616633
Tanacetum vulgare	LOTUS Database	35616633
Veratrum dahuricum	LOTUS Database	35616633
Verbascum sinaiticum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as flavonoid-7-o-glycosides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to carbohydrate moiety at the C7-position.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavonoid glycosides

Direct Parent

Flavonoid-7-O-glycosides

Alternative Parents

Substituents

Flavonoid-7-o-glycoside
4p-methoxyflavonoid-skeleton
Hydroxyflavonoid
5-hydroxyflavonoid
Flavone
Phenolic glycoside
Hexose monosaccharide
Glycosyl compound
O-glycosyl compound
Chromone
Benzopyran
1-benzopyran
Phenoxy compound
Phenol ether
Anisole
Methoxybenzene
Pyranone
1-hydroxy-2-unsubstituted benzenoid
1-hydroxy-4-unsubstituted benzenoid
Alkyl aryl ether
Pyran
Monosaccharide
Oxane
Monocyclic benzene moiety
Benzenoid
Heteroaromatic compound
Vinylogous acid
Secondary alcohol
Acetal
Oxacycle
Organoheterocyclic compound
Polyol
Ether
Organic oxide
Organic oxygen compound
Primary alcohol
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	0.72	ALOGPS
logP	0.58	ChemAxon
logS	-2.9	ALOGPS
pKa (Strongest Acidic)	7.31	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	155.14 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	109.54 m³·mol⁻¹	ChemAxon
Polarizability	44.16 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	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

FDB006051

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

5321954

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-2-(4-methoxyphenyl)-7-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}chromen-4-one (NP0224544)

MOL for NP0224544 (5-hydroxy-2-(4-methoxyphenyl)-7-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}chromen-4-one)

3D MOL for NP0224544 (5-hydroxy-2-(4-methoxyphenyl)-7-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}chromen-4-one)

3D SDF for NP0224544 (5-hydroxy-2-(4-methoxyphenyl)-7-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}chromen-4-one)

3D-SDF for NP0224544 (5-hydroxy-2-(4-methoxyphenyl)-7-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}chromen-4-one)

PDB for NP0224544 (5-hydroxy-2-(4-methoxyphenyl)-7-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}chromen-4-one)

3D PDB for NP0224544 (5-hydroxy-2-(4-methoxyphenyl)-7-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}chromen-4-one)

SMILES for NP0224544 (5-hydroxy-2-(4-methoxyphenyl)-7-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}chromen-4-one)

INCHI for NP0224544 (5-hydroxy-2-(4-methoxyphenyl)-7-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}chromen-4-one)

Structure for NP0224544 (5-hydroxy-2-(4-methoxyphenyl)-7-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}chromen-4-one)

3D Structure for NP0224544 (5-hydroxy-2-(4-methoxyphenyl)-7-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}chromen-4-one)