NP-MRD: Showing NP-Card for (2r,3r,4s,5r,6r)-2-[(acetyloxy)methyl]-5-{[(2s,3s,4r)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-6-[2-(3,4-dihydroxyphenyl)ethoxy]-4-{[(2s,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-3-yl (2e)-3-(3,4-dihydroxyphenyl)prop-2-enoate (NP0150690)

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Record Information

Version

2.0

Created at

2022-09-02 06:53:04 UTC

Updated at

2022-09-02 06:53:05 UTC

NP-MRD ID

NP0150690

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2r,3r,4s,5r,6r)-2-[(acetyloxy)methyl]-5-{[(2s,3s,4r)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-6-[2-(3,4-dihydroxyphenyl)ethoxy]-4-{[(2s,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-3-yl (2e)-3-(3,4-dihydroxyphenyl)prop-2-enoate

Description

LUTEOSIDE A belongs to the class of organic compounds known as oligosaccharides. These are carbohydrates made up of 3 to 10 monosaccharide units linked to each other through glycosidic bonds. (2r,3r,4s,5r,6r)-2-[(acetyloxy)methyl]-5-{[(2s,3s,4r)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-6-[2-(3,4-dihydroxyphenyl)ethoxy]-4-{[(2s,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-3-yl (2e)-3-(3,4-dihydroxyphenyl)prop-2-enoate is found in Markhamia lutea and Markhamia stipulata. (2r,3r,4s,5r,6r)-2-[(acetyloxy)methyl]-5-{[(2s,3s,4r)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-6-[2-(3,4-dihydroxyphenyl)ethoxy]-4-{[(2s,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-3-yl (2e)-3-(3,4-dihydroxyphenyl)prop-2-enoate was first documented in 1998 (PMID: 9599250). Based on a literature review very few articles have been published on LUTEOSIDE A.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309022208532D          

 56 60  0  0  1  0            999 V2000
   -4.5647  -12.0653    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7443  -11.9791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2593  -12.6465    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4087  -11.2254    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5882  -11.1392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2527  -10.3855    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.7376   -9.7181    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4020   -8.9644    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.8870   -8.2970    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7074   -8.3832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1924   -7.7158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0128   -7.8020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4978   -7.1345    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3182   -7.2208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6538   -7.9745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4743   -8.0607    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1689   -8.6419    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5044   -9.3956    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3484   -8.5557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5815   -8.8782    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.2460   -8.1245    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7309   -7.4570    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.5559   -7.4570    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8109   -6.6724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -6.1875    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5914   -5.5744    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6954   -5.5744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4405   -4.7898    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4760   -6.6724    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6914   -6.4175    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0966   -9.5456    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2761   -9.4594    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0594   -8.7057    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4255   -8.0382    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0900   -7.2846    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3449   -6.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7305   -7.1983    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0661   -6.4447    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2155   -7.8658    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0359   -7.7795    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8799   -8.6195    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3648   -9.2869    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4322  -10.2993    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9473  -10.9667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2828  -11.7204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1033  -11.8066    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7979  -12.3878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1335  -13.1415    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6485  -13.8089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1720  -13.7227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6569  -14.3901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3213  -15.1438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8062  -15.8113    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4992  -15.2301    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8347  -15.9837    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9841  -14.5626    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  6  5  1  1  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  1  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  2  0  0  0  0
 12 19  1  0  0  0  0
  8 20  1  0  0  0  0
 20 21  1  6  0  0  0
 22 21  1  6  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  1  0  0  0
 25 27  1  6  0  0  0
 27 28  1  0  0  0  0
 25 29  1  0  0  0  0
 22 29  1  0  0  0  0
 29 30  1  6  0  0  0
 20 31  1  0  0  0  0
 31 32  1  1  0  0  0
 33 32  1  6  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  1  0  0  0
 35 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
 33 41  1  0  0  0  0
 41 42  1  1  0  0  0
 31 43  1  0  0  0  0
  6 43  1  0  0  0  0
 43 44  1  6  0  0  0
 44 45  1  0  0  0  0
 45 46  2  0  0  0  0
 45 47  1  0  0  0  0
 47 48  2  0  0  0  0
 48 49  1  0  0  0  0
 49 50  2  0  0  0  0
 50 51  1  0  0  0  0
 51 52  2  0  0  0  0
 52 53  1  0  0  0  0
 52 54  1  0  0  0  0
 54 55  1  0  0  0  0
 54 56  2  0  0  0  0
 49 56  1  0  0  0  0
M  END

     RDKit          3D

102106  0  0  0  0  0  0  0  0999 V2000
   -4.4580    1.6137    2.3881 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4240    1.4036    0.9286 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3957    1.5030    0.1707 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1926    1.0636    0.3502 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0555    0.8430   -1.0331 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6314    0.5124   -1.3334 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8559    1.5868   -0.9191 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3530    1.1730   -0.3859 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0417    2.3243   -0.0160 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2773    2.3723   -0.6487 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0357    3.6175   -0.2596 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3187    4.8505   -0.6208 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    5.3949   -1.8650 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9019    6.5544   -2.2269 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0041    7.1608   -1.3522 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3685    8.3161   -1.7594 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7753    6.6042   -0.1238 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1224    7.2094    0.7516 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4322    5.4533    0.2367 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0539    0.4036    0.8980 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3324    0.0779    1.4059 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6076    0.7487    2.5960 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7606    1.4828    2.4765 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4776    1.4321    3.6410 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9003    0.3802    4.5285 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2387    0.9309    5.6181 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9121   -0.6628    4.9558 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8884   -0.1718    5.7866 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8643   -0.3021    3.6541 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3642   -1.4244    3.0358 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.9799   -2.1474    2.0853 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.9876   -2.9259    1.5540 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2471   -2.4508    1.9017 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.3527   -2.9889    1.0563 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4819   -2.7214    3.3758 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.3037   -1.7534    3.9429 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1880   -2.8580    4.1262 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.8315   -4.2103    4.1881 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0673   -2.0499    3.5470 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8980   -2.5224    4.1973 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1864   -0.8195   -0.8459 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1664   -1.3915   -1.6386 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3134   -2.5670   -2.3168 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3874   -3.2063   -2.2653 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7906   -3.1262   -3.1346 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9467   -2.4951   -3.2266 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0886   -2.9449   -3.9916 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1096   -4.1051   -4.7220 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2261   -4.5000   -5.4427 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3450   -3.7253   -5.4372 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4555   -4.1489   -6.1733 O   0  0  0  0  0  0  0  0  0  0  0  0
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    6.5070   -1.7867   -4.7265 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2363   -2.1842   -4.0072 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0433    2.5142    2.6802 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9555    0.7600    2.8971 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4374    1.6830    2.8149 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2843    1.8135   -1.5460 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7702    0.0851   -1.4081 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5255    0.4908   -2.4508 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9728    0.6092   -1.0809 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0948    2.3182   -1.7334 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8649    1.4792   -0.3616 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0184    3.5768   -0.7772 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2505    3.6084    0.8191 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2688    4.9229   -2.5546 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0944    6.9808   -3.2013 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2875    8.7738   -1.1396 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2983    6.8068    1.6596 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2732    4.9918    1.1942 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4081    1.1096    1.5823 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7311    1.3810    2.8454 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5503    2.4160    4.1622 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5484    1.1442    3.4350 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6663    1.8048    5.8190 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3464   -1.4386    5.5354 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3534   -1.1894    4.0906 H   0  0  0  0  0  0  0  0  0  0  0  0
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    2.0508   -2.2353    3.5080 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0457   -1.6961    0.6916 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0247   -2.7221    1.8539 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2216   -1.3491    1.7853 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3094   -2.8497    1.6067 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4598   -2.4106    0.1145 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2783   -4.0858    0.8669 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0178   -3.6886    3.4435 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0467   -1.5094    4.8632 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3587   -2.5257    5.1706 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8433   -4.2554    4.0962 H   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


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M  END
> <DATABASE_ID>
NP0150690

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H]1O[C@@H](O[C@@H]2[C@@H](O[C@@H]3OC[C@](O)(CO)[C@@H]3O)[C@H](OCCC3=CC=C(O)C(O)=C3)O[C@H](COC(C)=O)[C@H]2OC(=O)\C=C\C2=CC=C(O)C(O)=C2)[C@H](O)[C@H](O)[C@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C36H46O20/c1-16-26(44)27(45)28(46)33(52-16)55-30-29(54-25(43)8-5-18-3-6-20(39)22(41)11-18)24(13-50-17(2)38)53-34(49-10-9-19-4-7-21(40)23(42)12-19)31(30)56-35-32(47)36(48,14-37)15-51-35/h3-8,11-12,16,24,26-35,37,39-42,44-48H,9-10,13-15H2,1-2H3/b8-5+/t16-,24+,26-,27+,28+,29+,30-,31+,32+,33-,34+,35-,36+/m0/s1

> <INCHI_KEY>
CHCBSUXEBKZFGJ-SLPDEROOSA-N

> <FORMULA>
C36H46O20

> <MOLECULAR_WEIGHT>
798.744

> <EXACT_MASS>
798.258243881

> <JCHEM_ACCEPTOR_COUNT>
18

> <JCHEM_ATOM_COUNT>
102

> <JCHEM_AVERAGE_POLARIZABILITY>
77.25352736211391

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
10

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R,3R,4S,5R,6R)-2-[(acetyloxy)methyl]-5-{[(2S,3S,4R)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-6-[2-(3,4-dihydroxyphenyl)ethoxy]-4-{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-3-yl (2E)-3-(3,4-dihydroxyphenyl)prop-2-enoate

> <ALOGPS_LOGP>
1.03

> <JCHEM_LOGP>
-0.015948289333332616

> <ALOGPS_LOGS>
-2.78

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.641911110067483

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.009816474691963

> <JCHEM_PKA_STRONGEST_BASIC>
-3.676505498167413

> <JCHEM_POLAR_SURFACE_AREA>
310.28

> <JCHEM_REFRACTIVITY>
184.22480000000007

> <JCHEM_ROTATABLE_BOND_COUNT>
16

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.34e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2R,3R,4S,5R,6R)-2-[(acetyloxy)methyl]-5-{[(2S,3S,4R)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-6-[2-(3,4-dihydroxyphenyl)ethoxy]-4-{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-3-yl (2E)-3-(3,4-dihydroxyphenyl)prop-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 02-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-SEP-22         0                                  
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HETATM    2  C   UNK     0      -6.989 -22.361   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -6.084 -23.607   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      -6.363 -20.954   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      -4.831 -20.793   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -4.205 -19.386   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -5.110 -18.140   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -4.484 -16.734   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -5.389 -15.488   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      -6.921 -15.649   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -7.826 -14.403   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -9.357 -14.564   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0     -10.262 -13.318   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0     -11.794 -13.479   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0     -12.420 -14.886   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0     -13.952 -15.047   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0     -11.515 -16.132   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0     -12.142 -17.538   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      -9.984 -15.971   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -2.952 -16.573   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      -2.326 -15.166   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      -3.231 -13.920   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      -4.771 -13.920   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      -5.247 -12.455   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -4.001 -11.550   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      -2.971 -10.406   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      -5.031 -10.406   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      -4.556  -8.941   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      -2.755 -12.455   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      -1.291 -11.979   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      -2.047 -17.818   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      -0.515 -17.657   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       0.111 -16.251   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      -0.794 -15.005   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0      -0.168 -13.598   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      -0.644 -12.133   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       1.364 -13.437   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0       1.990 -12.030   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0       2.269 -14.683   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0       3.800 -14.522   0.000  0.00  0.00           O+0
HETATM   41  C   UNK     0       1.642 -16.090   0.000  0.00  0.00           C+0
HETATM   42  O   UNK     0       2.548 -17.336   0.000  0.00  0.00           O+0
HETATM   43  C   UNK     0      -2.673 -19.225   0.000  0.00  0.00           C+0
HETATM   44  O   UNK     0      -1.768 -20.471   0.000  0.00  0.00           O+0
HETATM   45  C   UNK     0      -2.395 -21.878   0.000  0.00  0.00           C+0
HETATM   46  O   UNK     0      -3.926 -22.039   0.000  0.00  0.00           O+0
HETATM   47  C   UNK     0      -1.489 -23.124   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0      -2.116 -24.531   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0      -1.211 -25.777   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0       0.321 -25.616   0.000  0.00  0.00           C+0
HETATM   51  C   UNK     0       1.226 -26.862   0.000  0.00  0.00           C+0
HETATM   52  C   UNK     0       0.600 -28.268   0.000  0.00  0.00           C+0
HETATM   53  O   UNK     0       1.505 -29.514   0.000  0.00  0.00           O+0
HETATM   54  C   UNK     0      -0.932 -28.429   0.000  0.00  0.00           C+0
HETATM   55  O   UNK     0      -1.558 -29.836   0.000  0.00  0.00           O+0
HETATM   56  C   UNK     0      -1.837 -27.184   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   43                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   20                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   19                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   12                                                       
CONECT   20    8   21   31                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23   29                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26   27   29                                             
CONECT   26   25                                                            
CONECT   27   25   28                                                       
CONECT   28   27                                                            
CONECT   29   25   22   30                                                  
CONECT   30   29                                                            
CONECT   31   20   32   43                                                  
CONECT   32   31   33                                                       
CONECT   33   32   34   41                                                  
CONECT   34   33   35                                                       
CONECT   35   34   36   37                                                  
CONECT   36   35                                                            
CONECT   37   35   38   39                                                  
CONECT   38   37                                                            
CONECT   39   37   40   41                                                  
CONECT   40   39                                                            
CONECT   41   39   33   42                                                  
CONECT   42   41                                                            
CONECT   43   31    6   44                                                  
CONECT   44   43   45                                                       
CONECT   45   44   46   47                                                  
CONECT   46   45                                                            
CONECT   47   45   48                                                       
CONECT   48   47   49                                                       
CONECT   49   48   50   56                                                  
CONECT   50   49   51                                                       
CONECT   51   50   52                                                       
CONECT   52   51   53   54                                                  
CONECT   53   52                                                            
CONECT   54   52   55   56                                                  
CONECT   55   54                                                            
CONECT   56   54   49                                                       
MASTER        0    0    0    0    0    0    0    0   56    0  120    0
END

View in JSmol

Synonyms

Value	Source
1-O-(3,4-Dihydroxyphenyl)ethyl apiofuranosyl-1-2-rhamnopyranosyl(1-3)-4-caffeoyl-6-acetylglucopyranoside	MeSH

Chemical Formula

C₃₆H₄₆O₂₀

Average Mass

798.7440 Da

Monoisotopic Mass

798.25824 Da

IUPAC Name

(2R,3R,4S,5R,6R)-2-[(acetyloxy)methyl]-5-{[(2S,3S,4R)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-6-[2-(3,4-dihydroxyphenyl)ethoxy]-4-{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-3-yl (2E)-3-(3,4-dihydroxyphenyl)prop-2-enoate

Traditional Name

CAS Registry Number

Not Available

SMILES

C[C@@H]1O[C@@H](O[C@@H]2[C@@H](O[C@@H]3OC[C@](O)(CO)[C@@H]3O)[C@H](OCCC3=CC=C(O)C(O)=C3)O[C@H](COC(C)=O)[C@H]2OC(=O)\C=C\C2=CC=C(O)C(O)=C2)[C@H](O)[C@H](O)[C@H]1O

InChI Identifier

InChI=1S/C36H46O20/c1-16-26(44)27(45)28(46)33(52-16)55-30-29(54-25(43)8-5-18-3-6-20(39)22(41)11-18)24(13-50-17(2)38)53-34(49-10-9-19-4-7-21(40)23(42)12-19)31(30)56-35-32(47)36(48,14-37)15-51-35/h3-8,11-12,16,24,26-35,37,39-42,44-48H,9-10,13-15H2,1-2H3/b8-5+/t16-,24+,26-,27+,28+,29+,30-,31+,32+,33-,34+,35-,36+/m0/s1

InChI Key

CHCBSUXEBKZFGJ-SLPDEROOSA-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
Markhamia lutea	LOTUS Database	35616633
Markhamia stipulata	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as oligosaccharides. These are carbohydrates made up of 3 to 10 monosaccharide units linked to each other through glycosidic bonds.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Oligosaccharides

Alternative Parents

Substituents

Oligosaccharide
Cinnamic acid or derivatives
Hydroxycinnamic acid or derivatives
Coumaric acid or derivatives
Cinnamic acid ester
O-glycosyl compound
Glycosyl compound
Tyrosol derivative
Styrene
Catechol
Phenol
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Fatty acid ester
Monocyclic benzene moiety
Fatty acyl
Benzenoid
Dicarboxylic acid or derivatives
Oxane
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Tetrahydrofuran
Tertiary alcohol
Carboxylic acid ester
Secondary alcohol
Acetal
Organoheterocyclic compound
Oxacycle
Carboxylic acid derivative
Polyol
Alcohol
Hydrocarbon derivative
Carbonyl group
Organic oxide
Primary alcohol
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic 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	1.03	ALOGPS
logP	-0.016	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Acidic)	9.01	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	18	ChemAxon
Hydrogen Donor Count	10	ChemAxon
Polar Surface Area	310.28 Å²	ChemAxon
Rotatable Bond Count	16	ChemAxon
Refractivity	184.22 m³·mol⁻¹	ChemAxon
Polarizability	77.25 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

C00037442

Chemspider ID

8804507

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10629144

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Kernan MR, Amarquaye A, Chen JL, Chan J, Sesin DF, Parkinson N, Ye Z, Barrett M, Bales C, Stoddart CA, Sloan B, Blanc P, Limbach C, Mrisho S, Rozhon EJ: Antiviral phenylpropanoid glycosides from the medicinal plant Markhamia lutea. J Nat Prod. 1998 May;61(5):564-70. doi: 10.1021/np9703914. [PubMed:9599250 ]
LOTUS database [Link]

Showing NP-Card for (2r,3r,4s,5r,6r)-2-[(acetyloxy)methyl]-5-{[(2s,3s,4r)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-6-[2-(3,4-dihydroxyphenyl)ethoxy]-4-{[(2s,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-3-yl (2e)-3-(3,4-dihydroxyphenyl)prop-2-enoate (NP0150690)

MOL for NP0150690 ((2r,3r,4s,5r,6r)-2-[(acetyloxy)methyl]-5-{[(2s,3s,4r)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-6-[2-(3,4-dihydroxyphenyl)ethoxy]-4-{[(2s,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-3-yl (2e)-3-(3,4-dihydroxyphenyl)prop-2-enoate)

3D MOL for NP0150690 ((2r,3r,4s,5r,6r)-2-[(acetyloxy)methyl]-5-{[(2s,3s,4r)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-6-[2-(3,4-dihydroxyphenyl)ethoxy]-4-{[(2s,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-3-yl (2e)-3-(3,4-dihydroxyphenyl)prop-2-enoate)

3D SDF for NP0150690 ((2r,3r,4s,5r,6r)-2-[(acetyloxy)methyl]-5-{[(2s,3s,4r)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-6-[2-(3,4-dihydroxyphenyl)ethoxy]-4-{[(2s,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-3-yl (2e)-3-(3,4-dihydroxyphenyl)prop-2-enoate)

3D-SDF for NP0150690 ((2r,3r,4s,5r,6r)-2-[(acetyloxy)methyl]-5-{[(2s,3s,4r)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-6-[2-(3,4-dihydroxyphenyl)ethoxy]-4-{[(2s,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-3-yl (2e)-3-(3,4-dihydroxyphenyl)prop-2-enoate)

PDB for NP0150690 ((2r,3r,4s,5r,6r)-2-[(acetyloxy)methyl]-5-{[(2s,3s,4r)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-6-[2-(3,4-dihydroxyphenyl)ethoxy]-4-{[(2s,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-3-yl (2e)-3-(3,4-dihydroxyphenyl)prop-2-enoate)

3D PDB for NP0150690 ((2r,3r,4s,5r,6r)-2-[(acetyloxy)methyl]-5-{[(2s,3s,4r)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-6-[2-(3,4-dihydroxyphenyl)ethoxy]-4-{[(2s,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-3-yl (2e)-3-(3,4-dihydroxyphenyl)prop-2-enoate)

SMILES for NP0150690 ((2r,3r,4s,5r,6r)-2-[(acetyloxy)methyl]-5-{[(2s,3s,4r)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-6-[2-(3,4-dihydroxyphenyl)ethoxy]-4-{[(2s,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-3-yl (2e)-3-(3,4-dihydroxyphenyl)prop-2-enoate)

INCHI for NP0150690 ((2r,3r,4s,5r,6r)-2-[(acetyloxy)methyl]-5-{[(2s,3s,4r)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-6-[2-(3,4-dihydroxyphenyl)ethoxy]-4-{[(2s,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-3-yl (2e)-3-(3,4-dihydroxyphenyl)prop-2-enoate)

Structure for NP0150690 ((2r,3r,4s,5r,6r)-2-[(acetyloxy)methyl]-5-{[(2s,3s,4r)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-6-[2-(3,4-dihydroxyphenyl)ethoxy]-4-{[(2s,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-3-yl (2e)-3-(3,4-dihydroxyphenyl)prop-2-enoate)

3D Structure for NP0150690 ((2r,3r,4s,5r,6r)-2-[(acetyloxy)methyl]-5-{[(2s,3s,4r)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-6-[2-(3,4-dihydroxyphenyl)ethoxy]-4-{[(2s,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-3-yl (2e)-3-(3,4-dihydroxyphenyl)prop-2-enoate)