NP-MRD: Showing NP-Card for [6-({2-[2-(3,4-dihydroxyphenyl)ethoxy]-5-{[3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-6-(hydroxymethyl)-3-[(3,4,5-trihydroxyoxan-2-yl)oxy]oxan-4-yl}oxy)-3,4,5-trihydroxyoxan-2-yl]methyl 3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate (NP0297848)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-10 08:34:27 UTC

Updated at

2022-09-10 08:34:27 UTC

NP-MRD ID

NP0297848

Secondary Accession Numbers

None

Natural Product Identification

Common Name

[6-({2-[2-(3,4-dihydroxyphenyl)ethoxy]-5-{[3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-6-(hydroxymethyl)-3-[(3,4,5-trihydroxyoxan-2-yl)oxy]oxan-4-yl}oxy)-3,4,5-trihydroxyoxan-2-yl]methyl 3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate

Description

[6-({2-[2-(3,4-Dihydroxyphenyl)ethoxy]-5-{[3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-6-(hydroxymethyl)-3-[(3,4,5-trihydroxyoxan-2-yl)oxy]oxan-4-yl}oxy)-3,4,5-trihydroxyoxan-2-yl]methyl 3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate belongs to the class of organic compounds known as annonaceous acetogenins. These are waxy derivatives of fatty acids (usually C32 or C34), containing a terminal carboxylic acid combined with a 2-propanol unit at the C-2 position to form a methyl- substituted alpha,beta-unsaturated-gamma-lactone. One of their interesting structural features is a single, adjacent, or nonadjacent tetrahydrofuran (THF) or tetrahydropyran (THP) system with one or two flanking hydroxyl group(s) at the center of a long hydrocarbon chain. [6-({2-[2-(3,4-dihydroxyphenyl)ethoxy]-5-{[3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-6-(hydroxymethyl)-3-[(3,4,5-trihydroxyoxan-2-yl)oxy]oxan-4-yl}oxy)-3,4,5-trihydroxyoxan-2-yl]methyl 3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate is found in Veronica thomsonii. [6-({2-[2-(3,4-Dihydroxyphenyl)ethoxy]-5-{[3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-6-(hydroxymethyl)-3-[(3,4,5-trihydroxyoxan-2-yl)oxy]oxan-4-yl}oxy)-3,4,5-trihydroxyoxan-2-yl]methyl 3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004241501022D          

 67 72  0  0  0  0            999 V2000
   -7.8592   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1447   -6.6000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1447   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4302   -7.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4302   -8.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7158   -9.0750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013   -8.6625    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   -8.6625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868   -9.9000    0.0000 O   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
   -2.8579   -9.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434  -10.3125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -9.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145  -10.3125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145  -11.1375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289  -11.5500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434  -11.1375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579  -11.5500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579  -12.3750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724  -12.7875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868  -12.3750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013  -12.7875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868  -11.5500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013  -11.1375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724  -11.1375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0573  -10.4701    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289  -12.3750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434  -12.7875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434  -13.6125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579  -14.0250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579  -14.8500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434  -15.2625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434  -16.0875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579  -16.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579  -17.3250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724  -16.0875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868  -16.5000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724  -15.2625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145  -12.7875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000  -12.3750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145  -12.7875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145  -13.6125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000  -11.5500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145  -11.1375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289  -11.5500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289  -12.3750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434  -11.1375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579  -11.5500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724  -11.1375    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
    4.2868   -9.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013  -10.3125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -9.9000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013  -11.1375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158  -11.5500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868  -11.5500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -9.0750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -8.6625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -8.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -7.8375    0.0000 O   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
   -3.1934   -8.3213    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1447   -9.0750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8592   -8.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8592   -7.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5737   -7.4250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  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
  6  5  1  4  0  0  0
  6  7  2  0  0  0  0
  7  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  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
 24 26  1  0  0  0  0
 19 26  1  0  0  0  0
 26 27  1  0  0  0  0
 17 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  2  0  0  0  0
 33 34  1  0  0  0  0
 34 35  2  0  0  0  0
 35 36  1  0  0  0  0
 35 37  1  0  0  0  0
 37 38  1  0  0  0  0
 37 39  2  0  0  0  0
 32 39  1  0  0  0  0
 28 40  1  0  0  0  0
 40 41  1  0  0  0  0
 41 42  1  0  0  0  0
 42 43  1  0  0  0  0
 41 44  1  0  0  0  0
 16 44  1  0  0  0  0
 44 45  1  0  0  0  0
 45 46  1  0  0  0  0
 46 47  2  0  0  0  0
 48 46  1  4  0  0  0
 48 49  2  0  0  0  0
 49 50  1  0  0  0  0
 50 51  2  0  0  0  0
 51 52  1  0  0  0  0
 52 53  2  0  0  0  0
 53 54  1  0  0  0  0
 53 55  1  0  0  0  0
 55 56  1  0  0  0  0
 55 57  2  0  0  0  0
 50 57  1  0  0  0  0
 14 58  1  0  0  0  0
 58 59  1  0  0  0  0
 58 60  1  0  0  0  0
 60 61  1  0  0  0  0
 60 62  1  0  0  0  0
 12 62  1  0  0  0  0
 62 63  1  0  0  0  0
  5 64  2  0  0  0  0
 64 65  1  0  0  0  0
 65 66  2  0  0  0  0
  3 66  1  0  0  0  0
 66 67  1  0  0  0  0
M  END

     RDKit          3D

119124  0  0  0  0  0  0  0  0999 V2000
   -5.1726   -4.1099   -1.7119 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3309   -4.9149   -2.8727 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2816   -5.6477   -3.4130 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0445   -5.5534   -2.7465 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9590   -6.2454   -3.2136 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6564   -6.2025   -2.5738 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4404   -5.4384   -1.5402 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8561   -5.3455   -0.8328 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8250   -6.0262   -1.1985 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9826   -4.5048    0.2325 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0359   -4.2463    1.0762 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6155   -3.1060    2.0718 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4766   -1.9570    1.3910 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4716   -1.1200    1.7876 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5079    0.1025    1.5434 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4410    1.3564    1.5100 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6581    2.1591    2.0170 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5738    1.2421    2.5632 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9140    1.2793    3.9464 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3347    2.1627    4.5750 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8523    0.3542    4.5121 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2940    0.1468    5.6900 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0974    0.6876    7.0062 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0512    0.4188    8.0208 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8734    0.8690    9.3045 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7779    1.5986    9.6916 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6105    2.0497   11.0003 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8334    1.8730    8.7308 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6794    2.6126    9.0452 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0239    1.4113    7.4319 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3336    3.0214    1.0367 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.6135    2.3829    0.5351 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4292    3.2835   -0.1033 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5495    3.5852    0.0686 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1993    3.4544    0.3608 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6115    4.2541   -0.3990 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3956    5.0843    0.4128 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2607    6.0087   -0.3830 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1746    5.2527   -1.2939 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3859    4.8442   -0.8585 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2188    4.1291   -1.7307 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7747    3.8600   -3.0202 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5718    3.1546   -3.8976 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5293    4.2953   -3.4303 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0104    4.0728   -4.6931 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7240    4.9961   -2.5615 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0630    1.9531    0.1733 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8112    1.4989   -0.7657 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3901    0.7359   -1.8035 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0410   -0.4895   -1.8764 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3089   -0.8802   -3.1447 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3393   -0.0340   -3.8556 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.6542   -0.3325   -3.4356 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0175    1.4236   -3.5742 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.9111    1.9544   -2.6734 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5833    1.5371   -3.0900 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2392    1.1216   -4.1188 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8163   -1.8441    1.2447 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6988   -2.1123   -0.0879 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8956   -3.1338    1.9954 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.9717   -3.0053    2.9159 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3296   -3.5770    2.7198 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2511   -3.2289    4.0551 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1031   -7.0331   -4.3477 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3213   -7.1124   -4.9861 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4293   -6.4241   -4.5329 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6805   -6.4958   -5.1732 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4778   -3.2681   -1.9599 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1535   -3.6426   -1.4574 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7808   -4.7390   -0.8885 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9688   -4.9312   -1.8636 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1570   -6.8015   -2.9391 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2554   -4.8145   -1.1489 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3196   -5.0652    1.7647 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9493   -3.8539    0.6056 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3970   -3.0745    2.8064 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2838   -1.2880    2.9127 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3367    1.7511    2.2808 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3462    2.8185    2.8981 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2902   -0.3431    3.7142 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0684   -0.7257    5.6915 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9180   -0.1510    7.7292 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6539    0.6311   10.0417 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7756    2.5775   11.2082 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9875    2.8165    8.3098 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2171    1.6317    6.7775 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7242    3.9259    1.6236 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1919    2.0513    1.4509 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4464    1.4526   -0.0298 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8807    4.0767   -0.4017 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0545    3.7174    1.4273 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0766    4.3846    0.9553 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8211    5.6044    1.1885 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8951    6.6563    0.2470 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6652    6.7119   -1.0120 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7437    5.0454    0.1314 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1881    3.7854   -1.4151 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2738    2.9498   -4.8134 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4915    3.5754   -5.4165 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7454    5.3446   -2.8682 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1162    1.7106    0.0344 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6981    0.5530   -1.7355 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7732   -1.9209   -3.1049 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4292   -1.0027   -3.8045 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3243   -0.2050   -4.9455 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2288    0.3250   -3.9112 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0952    1.9913   -4.5164 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7988    2.1092   -3.0202 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3724    2.6163   -2.9441 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0656    1.5965   -4.9425 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6870   -1.1778    1.4722 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4514   -1.8148   -0.6465 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2407   -3.9496    1.2794 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7330   -2.3585    3.6322 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3423   -4.6905    2.6924 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1209   -3.0971    4.4857 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2535   -7.5843   -4.7237 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4552   -7.7294   -5.8817 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8677   -7.0403   -5.9914 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  2  0
 19 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 26 28  1  0
 28 29  1  0
 28 30  2  0
 17 31  1  0
 31 32  1  0
 32 33  1  0
 31 34  1  0
 34 35  1  0
 35 36  1  0
 36 37  1  0
 37 38  1  0
 38 39  1  0
 39 40  2  0
 40 41  1  0
 41 42  2  0
 42 43  1  0
 42 44  1  0
 44 45  1  0
 44 46  2  0
 35 47  1  0
 47 48  1  0
 48 49  1  0
 49 50  1  0
 50 51  1  0
 51 52  1  0
 52 53  1  0
 52 54  1  0
 54 55  1  0
 54 56  1  0
 56 57  1  0
 14 58  1  0
 58 59  1  0
 58 60  1  0
 60 61  1  0
 60 62  1  0
 62 63  1  0
  5 64  2  0
 64 65  1  0
 65 66  2  0
 66 67  1  0
 66  3  1  0
 62 12  1  0
 47 16  1  0
 56 49  1  0
 30 23  1  0
 46 39  1  0
  1 68  1  0
  1 69  1  0
  1 70  1  0
  4 71  1  0
  6 72  1  0
  7 73  1  0
 11 74  1  0
 11 75  1  0
 12 76  1  1
 14 77  1  1
 16 78  1  1
 17 79  1  1
 21 80  1  0
 22 81  1  0
 24 82  1  0
 25 83  1  0
 27 84  1  0
 29 85  1  0
 30 86  1  0
 31 87  1  1
 32 88  1  0
 32 89  1  0
 33 90  1  0
 35 91  1  1
 37 92  1  0
 37 93  1  0
 38 94  1  0
 38 95  1  0
 40 96  1  0
 41 97  1  0
 43 98  1  0
 45 99  1  0
 46100  1  0
 47101  1  6
 49102  1  1
 51103  1  0
 51104  1  0
 52105  1  6
 53106  1  0
 54107  1  6
 55108  1  0
 56109  1  1
 57110  1  0
 58111  1  6
 59112  1  0
 60113  1  6
 61114  1  0
 62115  1  1
 63116  1  0
 64117  1  0
 65118  1  0
 67119  1  0
M  END


  Mrv1533004241501022D          

 67 72  0  0  0  0            999 V2000
   -7.8592   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1447   -6.6000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1447   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4302   -7.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4302   -8.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7158   -9.0750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013   -8.6625    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   -8.6625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868   -9.9000    0.0000 O   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
   -2.8579   -9.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434  -10.3125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -9.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145  -10.3125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145  -11.1375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289  -11.5500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434  -11.1375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579  -11.5500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579  -12.3750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724  -12.7875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868  -12.3750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013  -12.7875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868  -11.5500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013  -11.1375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724  -11.1375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0573  -10.4701    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289  -12.3750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434  -12.7875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434  -13.6125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579  -14.0250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579  -14.8500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434  -15.2625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434  -16.0875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579  -16.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579  -17.3250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724  -16.0875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868  -16.5000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724  -15.2625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145  -12.7875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000  -12.3750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145  -12.7875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145  -13.6125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000  -11.5500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145  -11.1375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289  -11.5500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289  -12.3750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434  -11.1375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579  -11.5500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724  -11.1375    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
    4.2868   -9.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013  -10.3125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -9.9000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013  -11.1375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158  -11.5500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868  -11.5500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -9.0750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -8.6625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -8.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -7.8375    0.0000 O   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
   -3.1934   -8.3213    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1447   -9.0750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8592   -8.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8592   -7.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5737   -7.4250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  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
  6  5  1  4  0  0  0
  6  7  2  0  0  0  0
  7  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  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
 24 26  1  0  0  0  0
 19 26  1  0  0  0  0
 26 27  1  0  0  0  0
 17 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  2  0  0  0  0
 33 34  1  0  0  0  0
 34 35  2  0  0  0  0
 35 36  1  0  0  0  0
 35 37  1  0  0  0  0
 37 38  1  0  0  0  0
 37 39  2  0  0  0  0
 32 39  1  0  0  0  0
 28 40  1  0  0  0  0
 40 41  1  0  0  0  0
 41 42  1  0  0  0  0
 42 43  1  0  0  0  0
 41 44  1  0  0  0  0
 16 44  1  0  0  0  0
 44 45  1  0  0  0  0
 45 46  1  0  0  0  0
 46 47  2  0  0  0  0
 48 46  1  4  0  0  0
 48 49  2  0  0  0  0
 49 50  1  0  0  0  0
 50 51  2  0  0  0  0
 51 52  1  0  0  0  0
 52 53  2  0  0  0  0
 53 54  1  0  0  0  0
 53 55  1  0  0  0  0
 55 56  1  0  0  0  0
 55 57  2  0  0  0  0
 50 57  1  0  0  0  0
 14 58  1  0  0  0  0
 58 59  1  0  0  0  0
 58 60  1  0  0  0  0
 60 61  1  0  0  0  0
 60 62  1  0  0  0  0
 12 62  1  0  0  0  0
 62 63  1  0  0  0  0
  5 64  2  0  0  0  0
 64 65  1  0  0  0  0
 65 66  2  0  0  0  0
  3 66  1  0  0  0  0
 66 67  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0297848

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(C=CC(=O)OCC2OC(OC3C(OC(=O)C=CC4=CC=C(O)C(O)=C4)C(CO)OC(OCCC4=CC=C(O)C(O)=C4)C3OC3OCC(O)C(O)C3O)C(O)C(O)C2O)=CC=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C44H52O23/c1-59-29-16-21(4-9-25(29)48)5-10-32(52)61-19-31-35(55)36(56)38(58)43(64-31)66-40-39(65-33(53)11-6-20-2-7-23(46)26(49)14-20)30(17-45)63-44(60-13-12-22-3-8-24(47)27(50)15-22)41(40)67-42-37(57)34(54)28(51)18-62-42/h2-11,14-16,28,30-31,34-51,54-58H,12-13,17-19H2,1H3

> <INCHI_KEY>
YRWQLJBYLFCVNM-UHFFFAOYSA-N

> <FORMULA>
C44H52O23

> <MOLECULAR_WEIGHT>
948.877

> <EXACT_MASS>
948.289937934

> <JCHEM_ACCEPTOR_COUNT>
21

> <JCHEM_ATOM_COUNT>
119

> <JCHEM_AVERAGE_POLARIZABILITY>
93.7679933565972

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
12

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
[6-({2-[2-(3,4-dihydroxyphenyl)ethoxy]-5-{[3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-6-(hydroxymethyl)-3-[(3,4,5-trihydroxyoxan-2-yl)oxy]oxan-4-yl}oxy)-3,4,5-trihydroxyoxan-2-yl]methyl 3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate

> <ALOGPS_LOGP>
1.77

> <JCHEM_LOGP>
1.2046688206666674

> <ALOGPS_LOGS>
-3.17

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.496604302977701

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.953776590155904

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6786408636978374

> <JCHEM_POLAR_SURFACE_AREA>
359.97

> <JCHEM_REFRACTIVITY>
224.40940000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
19

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
6.37e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[6-({2-[2-(3,4-dihydroxyphenyl)ethoxy]-5-{[3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-6-(hydroxymethyl)-3-[(3,4,5-trihydroxyoxan-2-yl)oxy]oxan-4-yl}oxy)-3,4,5-trihydroxyoxan-2-yl]methyl 3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-APR-15         0                                  
HETATM    1  C   UNK     0     -14.670 -11.550   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0     -13.337 -12.320   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0     -13.337 -13.860   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0     -12.003 -14.630   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0     -12.003 -16.170   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0     -10.669 -16.940   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -9.336 -16.170   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -8.002 -16.940   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -6.668 -16.170   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0      -8.002 -18.480   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      -6.668 -19.250   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -5.335 -18.480   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -4.001 -19.250   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      -2.667 -18.480   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -1.334 -19.250   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      -1.334 -20.790   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -2.667 -21.560   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -4.001 -20.790   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      -5.335 -21.560   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      -5.335 -23.100   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      -6.668 -23.870   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -8.002 -23.100   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      -9.336 -23.870   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      -8.002 -21.560   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      -9.336 -20.790   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      -6.668 -20.790   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      -7.574 -19.544   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      -2.667 -23.100   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      -4.001 -23.870   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      -4.001 -25.410   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -5.335 -26.180   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -5.335 -27.720   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -4.001 -28.490   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      -4.001 -30.030   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      -5.335 -30.800   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0      -5.335 -32.340   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0      -6.668 -30.030   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0      -8.002 -30.800   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0      -6.668 -28.490   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0      -1.334 -23.870   0.000  0.00  0.00           O+0
HETATM   41  C   UNK     0      -0.000 -23.100   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0       1.334 -23.870   0.000  0.00  0.00           C+0
HETATM   43  O   UNK     0       1.334 -25.410   0.000  0.00  0.00           O+0
HETATM   44  C   UNK     0      -0.000 -21.560   0.000  0.00  0.00           C+0
HETATM   45  O   UNK     0       1.334 -20.790   0.000  0.00  0.00           O+0
HETATM   46  C   UNK     0       2.667 -21.560   0.000  0.00  0.00           C+0
HETATM   47  O   UNK     0       2.667 -23.100   0.000  0.00  0.00           O+0
HETATM   48  C   UNK     0       4.001 -20.790   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0       5.335 -21.560   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0       6.668 -20.790   0.000  0.00  0.00           C+0
HETATM   51  C   UNK     0       6.668 -19.250   0.000  0.00  0.00           C+0
HETATM   52  C   UNK     0       8.002 -18.480   0.000  0.00  0.00           C+0
HETATM   53  C   UNK     0       9.336 -19.250   0.000  0.00  0.00           C+0
HETATM   54  O   UNK     0      10.669 -18.480   0.000  0.00  0.00           O+0
HETATM   55  C   UNK     0       9.336 -20.790   0.000  0.00  0.00           C+0
HETATM   56  O   UNK     0      10.669 -21.560   0.000  0.00  0.00           O+0
HETATM   57  C   UNK     0       8.002 -21.560   0.000  0.00  0.00           C+0
HETATM   58  C   UNK     0      -2.667 -16.940   0.000  0.00  0.00           C+0
HETATM   59  O   UNK     0      -1.334 -16.170   0.000  0.00  0.00           O+0
HETATM   60  C   UNK     0      -4.001 -16.170   0.000  0.00  0.00           C+0
HETATM   61  O   UNK     0      -4.001 -14.630   0.000  0.00  0.00           O+0
HETATM   62  C   UNK     0      -5.335 -16.940   0.000  0.00  0.00           C+0
HETATM   63  O   UNK     0      -5.961 -15.533   0.000  0.00  0.00           O+0
HETATM   64  C   UNK     0     -13.337 -16.940   0.000  0.00  0.00           C+0
HETATM   65  C   UNK     0     -14.670 -16.170   0.000  0.00  0.00           C+0
HETATM   66  C   UNK     0     -14.670 -14.630   0.000  0.00  0.00           C+0
HETATM   67  O   UNK     0     -16.004 -13.860   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   66                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   64                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   62                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   58                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   44                                                  
CONECT   17   16   18   28                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20   26                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   19   27                                                  
CONECT   27   26                                                            
CONECT   28   17   29   40                                                  
CONECT   29   28   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   33   39                                                  
CONECT   33   32   34                                                       
CONECT   34   33   35                                                       
CONECT   35   34   36   37                                                  
CONECT   36   35                                                            
CONECT   37   35   38   39                                                  
CONECT   38   37                                                            
CONECT   39   37   32                                                       
CONECT   40   28   41                                                       
CONECT   41   40   42   44                                                  
CONECT   42   41   43                                                       
CONECT   43   42                                                            
CONECT   44   41   16   45                                                  
CONECT   45   44   46                                                       
CONECT   46   45   47   48                                                  
CONECT   47   46                                                            
CONECT   48   46   49                                                       
CONECT   49   48   50                                                       
CONECT   50   49   51   57                                                  
CONECT   51   50   52                                                       
CONECT   52   51   53                                                       
CONECT   53   52   54   55                                                  
CONECT   54   53                                                            
CONECT   55   53   56   57                                                  
CONECT   56   55                                                            
CONECT   57   55   50                                                       
CONECT   58   14   59   60                                                  
CONECT   59   58                                                            
CONECT   60   58   61   62                                                  
CONECT   61   60                                                            
CONECT   62   60   12   63                                                  
CONECT   63   62                                                            
CONECT   64    5   65                                                       
CONECT   65   64   66                                                       
CONECT   66   65    3   67                                                  
CONECT   67   66                                                            
MASTER        0    0    0    0    0    0    0    0   67    0  144    0
END

View in JSmol

Synonyms

Value	Source
[6-({2-[2-(3,4-dihydroxyphenyl)ethoxy]-5-{[3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-6-(hydroxymethyl)-3-[(3,4,5-trihydroxyoxan-2-yl)oxy]oxan-4-yl}oxy)-3,4,5-trihydroxyoxan-2-yl]methyl 3-(4-hydroxy-3-methoxyphenyl)prop-2-enoic acid	Generator

Chemical Formula

C₄₄H₅₂O₂₃

Average Mass

948.8770 Da

Monoisotopic Mass

948.28994 Da

IUPAC Name

Traditional Name

CAS Registry Number

Not Available

SMILES

COC1=CC(C=CC(=O)OCC2OC(OC3C(OC(=O)C=CC4=CC=C(O)C(O)=C4)C(CO)OC(OCCC4=CC=C(O)C(O)=C4)C3OC3OCC(O)C(O)C3O)C(O)C(O)C2O)=CC=C1O

InChI Identifier

InChI=1S/C44H52O23/c1-59-29-16-21(4-9-25(29)48)5-10-32(52)61-19-31-35(55)36(56)38(58)43(64-31)66-40-39(65-33(53)11-6-20-2-7-23(46)26(49)14-20)30(17-45)63-44(60-13-12-22-3-8-24(47)27(50)15-22)41(40)67-42-37(57)34(54)28(51)18-62-42/h2-11,14-16,28,30-31,34-51,54-58H,12-13,17-19H2,1H3

InChI Key

YRWQLJBYLFCVNM-UHFFFAOYSA-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
Veronica thomsonii	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as annonaceous acetogenins. These are waxy derivatives of fatty acids (usually C32 or C34), containing a terminal carboxylic acid combined with a 2-propanol unit at the C-2 position to form a methyl- substituted alpha,beta-unsaturated-gamma-lactone. One of their interesting structural features is a single, adjacent, or nonadjacent tetrahydrofuran (THF) or tetrahydropyran (THP) system with one or two flanking hydroxyl group(s) at the center of a long hydrocarbon chain.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty alcohols

Direct Parent

Annonaceous acetogenins

Alternative Parents

Substituents

Annonaceae acetogenin skeleton
Long chain fatty alcohol
2-furanone
Dihydrofuran
Tetrahydrofuran
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Secondary alcohol
Lactone
Carboxylic acid ester
Monocarboxylic acid or derivatives
Ether
Dialkyl ether
Carboxylic acid derivative
Organoheterocyclic compound
Oxacycle
Organooxygen compound
Hydrocarbon derivative
Alcohol
Carbonyl group
Organic oxygen compound
Organic oxide
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic 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	1.77	ALOGPS
logP	1.2	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	8.95	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	21	ChemAxon
Hydrogen Donor Count	12	ChemAxon
Polar Surface Area	359.97 Å²	ChemAxon
Rotatable Bond Count	19	ChemAxon
Refractivity	224.41 m³·mol⁻¹	ChemAxon
Polarizability	93.77 Å³	ChemAxon
Number of Rings	6	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

75148978

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for [6-({2-[2-(3,4-dihydroxyphenyl)ethoxy]-5-{[3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-6-(hydroxymethyl)-3-[(3,4,5-trihydroxyoxan-2-yl)oxy]oxan-4-yl}oxy)-3,4,5-trihydroxyoxan-2-yl]methyl 3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate (NP0297848)

MOL for NP0297848 ([6-({2-[2-(3,4-dihydroxyphenyl)ethoxy]-5-{[3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-6-(hydroxymethyl)-3-[(3,4,5-trihydroxyoxan-2-yl)oxy]oxan-4-yl}oxy)-3,4,5-trihydroxyoxan-2-yl]methyl 3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate)

3D MOL for NP0297848 ([6-({2-[2-(3,4-dihydroxyphenyl)ethoxy]-5-{[3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-6-(hydroxymethyl)-3-[(3,4,5-trihydroxyoxan-2-yl)oxy]oxan-4-yl}oxy)-3,4,5-trihydroxyoxan-2-yl]methyl 3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate)

3D SDF for NP0297848 ([6-({2-[2-(3,4-dihydroxyphenyl)ethoxy]-5-{[3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-6-(hydroxymethyl)-3-[(3,4,5-trihydroxyoxan-2-yl)oxy]oxan-4-yl}oxy)-3,4,5-trihydroxyoxan-2-yl]methyl 3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate)

3D-SDF for NP0297848 ([6-({2-[2-(3,4-dihydroxyphenyl)ethoxy]-5-{[3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-6-(hydroxymethyl)-3-[(3,4,5-trihydroxyoxan-2-yl)oxy]oxan-4-yl}oxy)-3,4,5-trihydroxyoxan-2-yl]methyl 3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate)

PDB for NP0297848 ([6-({2-[2-(3,4-dihydroxyphenyl)ethoxy]-5-{[3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-6-(hydroxymethyl)-3-[(3,4,5-trihydroxyoxan-2-yl)oxy]oxan-4-yl}oxy)-3,4,5-trihydroxyoxan-2-yl]methyl 3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate)

3D PDB for NP0297848 ([6-({2-[2-(3,4-dihydroxyphenyl)ethoxy]-5-{[3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-6-(hydroxymethyl)-3-[(3,4,5-trihydroxyoxan-2-yl)oxy]oxan-4-yl}oxy)-3,4,5-trihydroxyoxan-2-yl]methyl 3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate)

SMILES for NP0297848 ([6-({2-[2-(3,4-dihydroxyphenyl)ethoxy]-5-{[3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-6-(hydroxymethyl)-3-[(3,4,5-trihydroxyoxan-2-yl)oxy]oxan-4-yl}oxy)-3,4,5-trihydroxyoxan-2-yl]methyl 3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate)

INCHI for NP0297848 ([6-({2-[2-(3,4-dihydroxyphenyl)ethoxy]-5-{[3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-6-(hydroxymethyl)-3-[(3,4,5-trihydroxyoxan-2-yl)oxy]oxan-4-yl}oxy)-3,4,5-trihydroxyoxan-2-yl]methyl 3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate)

Structure for NP0297848 ([6-({2-[2-(3,4-dihydroxyphenyl)ethoxy]-5-{[3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-6-(hydroxymethyl)-3-[(3,4,5-trihydroxyoxan-2-yl)oxy]oxan-4-yl}oxy)-3,4,5-trihydroxyoxan-2-yl]methyl 3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate)

3D Structure for NP0297848 ([6-({2-[2-(3,4-dihydroxyphenyl)ethoxy]-5-{[3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-6-(hydroxymethyl)-3-[(3,4,5-trihydroxyoxan-2-yl)oxy]oxan-4-yl}oxy)-3,4,5-trihydroxyoxan-2-yl]methyl 3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate)