NP-MRD: Showing NP-Card for [(2r,3s,4s,5r,6s)-6-[4-(6,8-dihydroxy-4-oxochromen-2-yl)phenoxy]-3,4,5-trihydroxyoxan-2-yl]methyl (2e)-3-(4-hydroxyphenyl)prop-2-enoate (NP0246738)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-07 08:18:07 UTC

Updated at

2022-09-07 08:18:07 UTC

NP-MRD ID

NP0246738

Secondary Accession Numbers

None

Natural Product Identification

Common Name

[(2r,3s,4s,5r,6s)-6-[4-(6,8-dihydroxy-4-oxochromen-2-yl)phenoxy]-3,4,5-trihydroxyoxan-2-yl]methyl (2e)-3-(4-hydroxyphenyl)prop-2-enoate

Description

[(2R,3S,4S,5R,6S)-6-[4-(6,8-dihydroxy-4-oxo-4H-chromen-2-yl)phenoxy]-3,4,5-trihydroxyoxan-2-yl]methyl (2E)-3-(4-hydroxyphenyl)prop-2-enoate belongs to the class of organic compounds known as flavonoid o-glycosides. Flavonoid O-glycosides are compounds containing a carbohydrate moiety which is O-glycosidically linked to the 2-phenylchromen-4-one flavonoid backbone. [(2r,3s,4s,5r,6s)-6-[4-(6,8-dihydroxy-4-oxochromen-2-yl)phenoxy]-3,4,5-trihydroxyoxan-2-yl]methyl (2e)-3-(4-hydroxyphenyl)prop-2-enoate is found in Leucas urticifolia. Based on a literature review very few articles have been published on [(2R,3S,4S,5R,6S)-6-[4-(6,8-dihydroxy-4-oxo-4H-chromen-2-yl)phenoxy]-3,4,5-trihydroxyoxan-2-yl]methyl (2E)-3-(4-hydroxyphenyl)prop-2-enoate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309072210182D          

 42 46  0  0  1  0            999 V2000
   -5.0013   -6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -7.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -8.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -9.0750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -9.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724  -10.3125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724  -11.1375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868   -9.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868   -9.0750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -4.9500    0.0000 C   0  0  1  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
   -2.1434   -3.7125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1434   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -2.4750    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
   -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 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    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
    1.4289   -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  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
   -1.4289   -4.1250    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
   -1.4289   -4.9500    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7145   -5.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -5.3625    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1434   -6.1875    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
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  2  0  0  0  0
  5 11  1  0  0  0  0
  2 12  1  0  0  0  0
 12 13  1  0  0  0  0
 14 13  1  1  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  1  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 24 26  1  0  0  0  0
 26 27  2  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 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
 26 33  1  0  0  0  0
 33 34  1  0  0  0  0
 22 34  1  0  0  0  0
 21 35  1  0  0  0  0
 35 36  2  0  0  0  0
 18 36  1  0  0  0  0
 16 37  1  0  0  0  0
 37 38  1  6  0  0  0
 37 39  1  0  0  0  0
 39 40  1  1  0  0  0
 39 41  1  0  0  0  0
 14 41  1  0  0  0  0
 41 42  1  6  0  0  0
M  END

     RDKit          3D

 68 72  0  0  0  0  0  0  0  0999 V2000
   -4.5000    1.6128    3.6225 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0417    1.0821    2.6212 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4586    0.7294    2.6446 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0133    0.1733    1.5943 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4053   -0.1897    1.5760 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2516    0.0277    2.6213 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.6005   -0.3406    2.5650 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.1056   -0.9350    1.4457 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.4597   -1.3030    1.3945 O   0  0  0  0  0  0  0  0  0  0  0  0
  -10.2648   -1.1752    0.3505 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9422   -0.7979    0.4412 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2378    0.8517    1.5100 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8548    1.1965    1.4917 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3325    0.7912    0.1259 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0142    1.0911    0.0555 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2711    0.6095   -0.9735 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7926   -0.1212   -0.4272 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1385    0.0735   -0.5666 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0025   -0.8035    0.1117 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3627   -0.6446   -0.0025 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9310    0.3572   -0.7677 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3768    0.5001   -0.8681 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9996    1.4492   -1.6399 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3818    1.5478   -1.7074 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9528    2.4219   -2.4182 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.1685    0.6775   -0.9862 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5505    0.7326   -1.0176 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3233   -0.1487   -0.2880 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7095   -0.0817   -0.3294 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.6561   -1.0848    0.4726 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2789   -1.1387    0.5037 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6224   -2.0921    1.2789 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.4843   -0.2562   -0.2275 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1786   -0.3226   -0.1860 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0892    1.2030   -1.4213 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6880    1.0688   -1.3269 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9813   -0.1827   -2.0250 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.2311    0.5821   -3.1715 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2183   -0.8725   -1.6001 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.2844   -2.2251   -1.9415 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4923   -0.6998   -0.0999 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.7941   -1.1346    0.1337 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0200    0.9318    3.5217 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3784   -0.0183    0.6917 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9060    0.4963    3.5336 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.2265   -0.1493    3.4062 H   0  0  0  0  0  0  0  0  0  0  0  0
  -13.1199   -0.6136    1.0419 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.6978   -1.6481   -0.5206 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2857   -0.9798   -0.4006 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7805    2.2958    1.6038 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3092    0.7244    2.3082 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8882    1.3499   -0.6566 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1571    1.4905   -1.5019 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5825   -1.5993    0.7153 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0552   -1.3064    0.5086 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4104    2.1608   -2.2293 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.0392    1.4992   -1.6398 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.1763   -0.6451   -1.0587 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.2510   -1.7907    1.0559 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6245   -2.1654    1.3302 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4590    1.9937   -2.0239 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0534    1.7565   -1.8582 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2587   -0.9804   -2.3728 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5027    1.4883   -2.9458 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1127   -0.3965   -2.1008 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1601   -2.3189   -2.9171 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7275   -1.2671    0.4308 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3675   -0.5874   -0.4902 H   0  0  0  0  0  0  0  0  0  0  0  0
 42 41  1  0
 41 14  1  0
 14 13  1  0
 13 12  1  0
 12  2  1  0
  2  1  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  8 10  1  0
 10 11  2  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 35  1  0
 35 36  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 24 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 34  1  0
 16 37  1  0
 37 38  1  0
 37 39  1  0
 39 40  1  0
 39 41  1  0
 11  5  1  0
 36 18  1  0
 34 22  1  0
 33 26  1  0
 42 68  1  0
 41 67  1  1
 14 52  1  6
 13 50  1  0
 13 51  1  0
  3 43  1  0
  4 44  1  0
  6 45  1  0
  7 46  1  0
  9 47  1  0
 10 48  1  0
 11 49  1  0
 16 53  1  6
 19 54  1  0
 20 55  1  0
 35 61  1  0
 36 62  1  0
 23 56  1  0
 27 57  1  0
 29 58  1  0
 30 59  1  0
 32 60  1  0
 37 63  1  6
 38 64  1  0
 39 65  1  6
 40 66  1  0
M  END


  Mrv1652309072210182D          

 42 46  0  0  1  0            999 V2000
   -5.0013   -6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -7.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -8.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -9.0750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -9.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724  -10.3125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724  -11.1375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868   -9.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868   -9.0750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -4.9500    0.0000 C   0  0  1  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
   -2.1434   -3.7125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1434   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -2.4750    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
   -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 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    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
    1.4289   -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  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
   -1.4289   -4.1250    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
   -1.4289   -4.9500    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7145   -5.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -5.3625    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1434   -6.1875    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
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  2  0  0  0  0
  5 11  1  0  0  0  0
  2 12  1  0  0  0  0
 12 13  1  0  0  0  0
 14 13  1  1  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  1  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 24 26  1  0  0  0  0
 26 27  2  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 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
 26 33  1  0  0  0  0
 33 34  1  0  0  0  0
 22 34  1  0  0  0  0
 21 35  1  0  0  0  0
 35 36  2  0  0  0  0
 18 36  1  0  0  0  0
 16 37  1  0  0  0  0
 37 38  1  6  0  0  0
 37 39  1  0  0  0  0
 39 40  1  1  0  0  0
 39 41  1  0  0  0  0
 14 41  1  0  0  0  0
 41 42  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0246738

> <DATABASE_NAME>
NP-MRD

> <SMILES>
O[C@@H]1[C@@H](COC(=O)\C=C\C2=CC=C(O)C=C2)O[C@@H](OC2=CC=C(C=C2)C2=CC(=O)C3=CC(O)=CC(O)=C3O2)[C@H](O)[C@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C30H26O12/c31-17-6-1-15(2-7-17)3-10-25(35)39-14-24-26(36)27(37)28(38)30(42-24)40-19-8-4-16(5-9-19)23-13-21(33)20-11-18(32)12-22(34)29(20)41-23/h1-13,24,26-28,30-32,34,36-38H,14H2/b10-3+/t24-,26-,27+,28-,30-/m1/s1

> <INCHI_KEY>
GBLAJVQSEVWRNT-OTDDKLKWSA-N

> <FORMULA>
C30H26O12

> <MOLECULAR_WEIGHT>
578.526

> <EXACT_MASS>
578.142426277

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_ATOM_COUNT>
68

> <JCHEM_AVERAGE_POLARIZABILITY>
57.2248460223923

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
[(2R,3S,4S,5R,6S)-6-[4-(6,8-dihydroxy-4-oxo-4H-chromen-2-yl)phenoxy]-3,4,5-trihydroxyoxan-2-yl]methyl (2E)-3-(4-hydroxyphenyl)prop-2-enoate

> <JCHEM_LOGP>
2.518946436666666

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.450247341069367

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.754777955473262

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6491102894891405

> <JCHEM_POLAR_SURFACE_AREA>
192.43999999999997

> <JCHEM_REFRACTIVITY>
146.6069

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
[(2R,3S,4S,5R,6S)-6-[4-(6,8-dihydroxy-4-oxochromen-2-yl)phenoxy]-3,4,5-trihydroxyoxan-2-yl]methyl (2E)-3-(4-hydroxyphenyl)prop-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 07-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-SEP-22         0                                  
HETATM    1  O   UNK     0      -9.336 -11.550   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      -8.002 -12.320   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -8.002 -13.860   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -6.668 -14.630   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -6.668 -16.170   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -5.335 -16.940   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -5.335 -18.480   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -6.668 -19.250   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -6.668 -20.790   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      -8.002 -18.480   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -8.002 -16.940   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -6.668 -11.550   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      -6.668 -10.010   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -5.335  -9.240   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -5.335  -7.700   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      -4.001  -6.930   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -4.001  -5.390   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      -2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       0.000  -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  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       2.667   1.540   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
HETATM   34  O   UNK     0       2.667  -3.080   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      -2.667  -7.700   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0      -1.334  -6.930   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0      -2.667  -9.240   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0      -1.334 -10.010   0.000  0.00  0.00           O+0
HETATM   41  C   UNK     0      -4.001 -10.010   0.000  0.00  0.00           C+0
HETATM   42  O   UNK     0      -4.001 -11.550   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   12                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   11                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10    5                                                       
CONECT   12    2   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   41                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   37                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   36                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22   35                                                  
CONECT   22   21   23   34                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   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   26   34                                                  
CONECT   34   33   22                                                       
CONECT   35   21   36                                                       
CONECT   36   35   18                                                       
CONECT   37   16   38   39                                                  
CONECT   38   37                                                            
CONECT   39   37   40   41                                                  
CONECT   40   39                                                            
CONECT   41   39   14   42                                                  
CONECT   42   41                                                            
MASTER        0    0    0    0    0    0    0    0   42    0   92    0
END

View in JSmol

Synonyms

Value	Source
[(2R,3S,4S,5R,6S)-6-[4-(6,8-Dihydroxy-4-oxo-4H-chromen-2-yl)phenoxy]-3,4,5-trihydroxyoxan-2-yl]methyl (2E)-3-(4-hydroxyphenyl)prop-2-enoic acid	Generator

Chemical Formula

C₃₀H₂₆O₁₂

Average Mass

578.5260 Da

Monoisotopic Mass

578.14243 Da

IUPAC Name

[(2R,3S,4S,5R,6S)-6-[4-(6,8-dihydroxy-4-oxo-4H-chromen-2-yl)phenoxy]-3,4,5-trihydroxyoxan-2-yl]methyl (2E)-3-(4-hydroxyphenyl)prop-2-enoate

Traditional Name

[(2R,3S,4S,5R,6S)-6-[4-(6,8-dihydroxy-4-oxochromen-2-yl)phenoxy]-3,4,5-trihydroxyoxan-2-yl]methyl (2E)-3-(4-hydroxyphenyl)prop-2-enoate

CAS Registry Number

Not Available

SMILES

O[C@@H]1[C@@H](COC(=O)\C=C\C2=CC=C(O)C=C2)O[C@@H](OC2=CC=C(C=C2)C2=CC(=O)C3=CC(O)=CC(O)=C3O2)[C@H](O)[C@H]1O

InChI Identifier

InChI=1S/C30H26O12/c31-17-6-1-15(2-7-17)3-10-25(35)39-14-24-26(36)27(37)28(38)30(42-24)40-19-8-4-16(5-9-19)23-13-21(33)20-11-18(32)12-22(34)29(20)41-23/h1-13,24,26-28,30-32,34,36-38H,14H2/b10-3+/t24-,26-,27+,28-,30-/m1/s1

InChI Key

GBLAJVQSEVWRNT-OTDDKLKWSA-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
Leucas urticifolia	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as flavonoid o-glycosides. Flavonoid O-glycosides are compounds containing a carbohydrate moiety which is O-glycosidically linked to the 2-phenylchromen-4-one flavonoid backbone.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavonoid glycosides

Direct Parent

Flavonoid O-glycosides

Alternative Parents

Substituents

Flavonoid o-glycoside
Flavonoid-4p-o-glycoside
Hydroxyflavonoid
6-hydroxyflavonoid
8-hydroxyflavonoid
Flavone
Phenolic glycoside
Coumaric acid ester
Hydroxycinnamic acid or derivatives
Cinnamic acid or derivatives
Coumaric acid or derivatives
Cinnamic acid ester
Glycosyl compound
O-glycosyl compound
Chromone
Benzopyran
1-benzopyran
Phenol ether
Phenoxy compound
Styrene
Fatty acid ester
Pyranone
Phenol
1-hydroxy-2-unsubstituted benzenoid
1-hydroxy-4-unsubstituted benzenoid
Pyran
Benzenoid
Oxane
Fatty acyl
Monosaccharide
Monocyclic benzene moiety
Heteroaromatic compound
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Secondary alcohol
Carboxylic acid ester
Acetal
Organoheterocyclic compound
Oxacycle
Carboxylic acid derivative
Polyol
Monocarboxylic acid or derivatives
Organic oxide
Carbonyl group
Organic oxygen compound
Hydrocarbon derivative
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	2.52	ChemAxon
pKa (Strongest Acidic)	8.75	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	192.44 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	146.61 m³·mol⁻¹	ChemAxon
Polarizability	57.22 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	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

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

163190278

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for [(2r,3s,4s,5r,6s)-6-[4-(6,8-dihydroxy-4-oxochromen-2-yl)phenoxy]-3,4,5-trihydroxyoxan-2-yl]methyl (2e)-3-(4-hydroxyphenyl)prop-2-enoate (NP0246738)

MOL for NP0246738 ([(2r,3s,4s,5r,6s)-6-[4-(6,8-dihydroxy-4-oxochromen-2-yl)phenoxy]-3,4,5-trihydroxyoxan-2-yl]methyl (2e)-3-(4-hydroxyphenyl)prop-2-enoate)

3D MOL for NP0246738 ([(2r,3s,4s,5r,6s)-6-[4-(6,8-dihydroxy-4-oxochromen-2-yl)phenoxy]-3,4,5-trihydroxyoxan-2-yl]methyl (2e)-3-(4-hydroxyphenyl)prop-2-enoate)

3D SDF for NP0246738 ([(2r,3s,4s,5r,6s)-6-[4-(6,8-dihydroxy-4-oxochromen-2-yl)phenoxy]-3,4,5-trihydroxyoxan-2-yl]methyl (2e)-3-(4-hydroxyphenyl)prop-2-enoate)

3D-SDF for NP0246738 ([(2r,3s,4s,5r,6s)-6-[4-(6,8-dihydroxy-4-oxochromen-2-yl)phenoxy]-3,4,5-trihydroxyoxan-2-yl]methyl (2e)-3-(4-hydroxyphenyl)prop-2-enoate)

PDB for NP0246738 ([(2r,3s,4s,5r,6s)-6-[4-(6,8-dihydroxy-4-oxochromen-2-yl)phenoxy]-3,4,5-trihydroxyoxan-2-yl]methyl (2e)-3-(4-hydroxyphenyl)prop-2-enoate)

3D PDB for NP0246738 ([(2r,3s,4s,5r,6s)-6-[4-(6,8-dihydroxy-4-oxochromen-2-yl)phenoxy]-3,4,5-trihydroxyoxan-2-yl]methyl (2e)-3-(4-hydroxyphenyl)prop-2-enoate)

SMILES for NP0246738 ([(2r,3s,4s,5r,6s)-6-[4-(6,8-dihydroxy-4-oxochromen-2-yl)phenoxy]-3,4,5-trihydroxyoxan-2-yl]methyl (2e)-3-(4-hydroxyphenyl)prop-2-enoate)

INCHI for NP0246738 ([(2r,3s,4s,5r,6s)-6-[4-(6,8-dihydroxy-4-oxochromen-2-yl)phenoxy]-3,4,5-trihydroxyoxan-2-yl]methyl (2e)-3-(4-hydroxyphenyl)prop-2-enoate)

Structure for NP0246738 ([(2r,3s,4s,5r,6s)-6-[4-(6,8-dihydroxy-4-oxochromen-2-yl)phenoxy]-3,4,5-trihydroxyoxan-2-yl]methyl (2e)-3-(4-hydroxyphenyl)prop-2-enoate)

3D Structure for NP0246738 ([(2r,3s,4s,5r,6s)-6-[4-(6,8-dihydroxy-4-oxochromen-2-yl)phenoxy]-3,4,5-trihydroxyoxan-2-yl]methyl (2e)-3-(4-hydroxyphenyl)prop-2-enoate)