NP-MRD: Showing NP-Card for methyl 4-[(2-acetyl-6,7-dihydroxy-3,4-dihydro-1h-isoquinolin-1-yl)methyl]-5-ethenyl-6-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5,6-dihydro-4h-pyran-3-carboxylate (NP0197174)

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Record Information

Version

2.0

Created at

2022-09-04 15:23:26 UTC

Updated at

2022-09-04 15:23:26 UTC

NP-MRD ID

NP0197174

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl 4-[(2-acetyl-6,7-dihydroxy-3,4-dihydro-1h-isoquinolin-1-yl)methyl]-5-ethenyl-6-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5,6-dihydro-4h-pyran-3-carboxylate

Description

Ipecoside belongs to the class of organic compounds known as terpene glycosides. These are prenol lipids containing a carbohydrate moiety glycosidically bound to a terpene backbone. methyl 4-[(2-acetyl-6,7-dihydroxy-3,4-dihydro-1h-isoquinolin-1-yl)methyl]-5-ethenyl-6-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5,6-dihydro-4h-pyran-3-carboxylate is found in Carapichea ipecacuanha. Ipecoside is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004201502172D          

 40 43  0  0  0  0            999 V2000
    4.6418   -2.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9989   -2.0519    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1449   -2.2045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2574   -1.7961    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7879   -2.9166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3400   -3.5297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0850   -4.3143    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2781   -4.4858    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0011   -5.3006    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5752   -5.8835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3737   -5.6762    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9525   -6.2640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7510   -6.0566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3299   -6.6445    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7329   -7.0592    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3117   -7.6471    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9343   -7.2666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7147   -8.0618    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3555   -6.6787    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5570   -6.8861    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7260   -3.8727    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9508   -4.2653    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4289   -4.9387    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9810   -3.0881    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3139   -2.5079    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 N   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
    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
    4.2020    0.1880    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
    4.5146   -1.5653    0.0000 O   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
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1422   -1.5484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9489   -1.3105    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7456   -2.1909    0.0000 C   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
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  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  1  0  0  0  0
 13 14  1  0  0  0  0
 12 15  1  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  1  0  0  0  0
 10 19  1  0  0  0  0
 19 20  1  0  0  0  0
  8 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 21 24  1  0  0  0  0
  5 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 32 34  2  0  0  0  0
 34 35  1  0  0  0  0
 34 36  1  0  0  0  0
 36 37  2  0  0  0  0
 26 37  1  0  0  0  0
 30 37  1  0  0  0  0
 27 38  1  0  0  0  0
 38 39  2  0  0  0  0
 38 40  1  0  0  0  0
M  END

     RDKit          3D

 75 78  0  0  0  0  0  0  0  0999 V2000
    2.2000    0.5421   -2.9836 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7350   -0.1317   -1.9415 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8371    0.5077   -0.9513 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4730    0.5453    0.3899 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8727    0.3692    0.3255 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5331    1.4695    0.8126 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.3127    1.1930    1.9306 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2843    0.2379    1.6827 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.0441    0.0239    2.9766 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0486   -0.9198    2.8426 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2566    0.6316    0.6245 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.3293    1.3482    1.1746 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6538    1.3571   -0.5306 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.4384    0.5227   -1.6386 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4220    2.1361   -0.2035 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.7221    3.4206    0.2822 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9918   -0.4399    1.2735 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5308   -1.6349    0.7650 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2250   -1.5739   -0.3470 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7173   -2.8540   -0.8859 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4202   -3.9057   -0.2841 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4823   -2.9348   -2.0161 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9593   -4.1819   -2.5411 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4813   -0.2990   -0.9646 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6171    0.5287   -0.5107 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9502   -0.0341   -0.6308 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.0445    0.9375   -0.3165 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8380    2.2392    0.0001 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9070    3.0950    0.3088 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6601    4.4186    0.6276 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1709    2.5495    0.2745 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2870    3.3317    0.5688 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4095    1.2129   -0.0487 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3325    0.3840   -0.3517 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5683   -1.0176   -0.7171 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4396   -1.9480   -0.4108 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2987   -1.1777    0.1602 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8501   -1.5639    1.4203 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2459   -2.8586    2.0282 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0923   -0.8321    2.0928 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9127    1.5741   -3.1025 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8522    0.1073   -3.7186 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0073   -1.1635   -1.8006 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5643    1.5283   -1.3301 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2907    1.5516    0.8282 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7889    2.2430    1.1441 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8220   -0.7547    1.4234 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5517    0.9914    3.2401 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3594   -0.1856    3.8250 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5675   -0.9033    3.6900 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7114   -0.3159    0.2178 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9710    1.4902    0.4365 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4244    2.1044   -0.8842 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7704   -0.1639   -1.4816 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8286    2.2836   -1.1382 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9494    3.7358    0.7947 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7550   -2.5990    1.2254 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4393   -5.0047   -2.0448 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6208   -4.1859   -3.6148 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0457   -4.2425   -2.5631 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6285   -0.4992   -2.0973 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4036    0.8846    0.5622 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5134    1.5245   -1.0696 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1148   -0.3343   -1.7573 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8237    2.6571    0.0226 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4260    5.0294    0.8482 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2857    4.2875    0.8141 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4342    0.8230   -0.0630 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6691   -1.0164   -1.8484 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5437   -1.3964   -0.3212 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0349   -2.4590   -1.2990 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7919   -2.6925    0.3088 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2022   -3.6120    1.1941 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2770   -2.8343    2.4332 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5601   -3.1474    2.8382 H   0  0  0  0  0  0  0  0  0  0  0  0
 23 22  1  0
 22 20  1  0
 20 21  2  0
 20 19  1  0
 19 18  2  0
 18 17  1  0
 17  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  8 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
  4  3  1  0
  3  2  1  0
  2  1  2  3
  3 24  1  0
 24 25  1  0
 25 26  1  0
 26 37  1  0
 37 36  1  0
 36 35  1  0
 35 34  1  0
 34 33  2  0
 33 31  1  0
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 29 30  1  0
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 37 38  1  0
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 38 40  2  0
 24 19  1  0
 27 26  1  0
 15  6  1  0
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 23 58  1  0
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 18 57  1  0
  4 45  1  1
  6 46  1  1
  8 47  1  6
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  9 49  1  0
 10 50  1  0
 11 51  1  6
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 15 55  1  6
 16 56  1  0
  3 44  1  6
  2 43  1  0
  1 41  1  0
  1 42  1  0
 24 61  1  6
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 25 63  1  0
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 36 71  1  0
 36 72  1  0
 35 69  1  0
 35 70  1  0
 33 68  1  0
 32 67  1  0
 30 66  1  0
 28 65  1  0
 39 73  1  0
 39 74  1  0
 39 75  1  0
M  END


  Mrv1533004201502172D          

 40 43  0  0  0  0            999 V2000
    4.6418   -2.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9989   -2.0519    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1449   -2.2045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2574   -1.7961    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7879   -2.9166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3400   -3.5297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0850   -4.3143    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2781   -4.4858    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0011   -5.3006    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5752   -5.8835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3737   -5.6762    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9525   -6.2640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7510   -6.0566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3299   -6.6445    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7329   -7.0592    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3117   -7.6471    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9343   -7.2666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7147   -8.0618    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3555   -6.6787    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.7260   -3.8727    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9508   -4.2653    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4289   -4.9387    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9810   -3.0881    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3139   -2.5079    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 N   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
    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
    4.2020    0.1880    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
    4.5146   -1.5653    0.0000 O   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
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1422   -1.5484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9489   -1.3105    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7456   -2.1909    0.0000 C   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
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  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  1  0  0  0  0
 13 14  1  0  0  0  0
 12 15  1  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  1  0  0  0  0
 10 19  1  0  0  0  0
 19 20  1  0  0  0  0
  8 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 21 24  1  0  0  0  0
  5 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 32 34  2  0  0  0  0
 34 35  1  0  0  0  0
 34 36  1  0  0  0  0
 36 37  2  0  0  0  0
 26 37  1  0  0  0  0
 30 37  1  0  0  0  0
 27 38  1  0  0  0  0
 38 39  2  0  0  0  0
 38 40  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0197174

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)C1=COC(OC2OC(CO)C(O)C(O)C2O)C(C=C)C1CC1N(CCC2=CC(O)=C(O)C=C12)C(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C27H35NO12/c1-4-14-16(8-18-15-9-20(32)19(31)7-13(15)5-6-28(18)12(2)30)17(25(36)37-3)11-38-26(14)40-27-24(35)23(34)22(33)21(10-29)39-27/h4,7,9,11,14,16,18,21-24,26-27,29,31-35H,1,5-6,8,10H2,2-3H3

> <INCHI_KEY>
QISXROCIXKXUPS-UHFFFAOYSA-N

> <FORMULA>
C27H35NO12

> <MOLECULAR_WEIGHT>
565.572

> <EXACT_MASS>
565.215925571

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_ATOM_COUNT>
75

> <JCHEM_AVERAGE_POLARIZABILITY>
56.29261998803327

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
methyl 4-[(2-acetyl-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinolin-1-yl)methyl]-3-ethenyl-2-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,4-dihydro-2H-pyran-5-carboxylate

> <ALOGPS_LOGP>
0.22

> <JCHEM_LOGP>
-0.49513287666666583

> <ALOGPS_LOGS>
-2.65

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.068598121009273

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.190032438847089

> <JCHEM_PKA_STRONGEST_BASIC>
-1.322452634792219

> <JCHEM_POLAR_SURFACE_AREA>
195.68

> <JCHEM_REFRACTIVITY>
137.26149999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.26e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl 4-[(2-acetyl-6,7-dihydroxy-3,4-dihydro-1H-isoquinolin-1-yl)methyl]-5-ethenyl-6-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5,6-dihydro-4H-pyran-3-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 20-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-APR-15         0                                  
HETATM    1  C   UNK     0       8.665  -4.947   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       7.465  -3.830   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       5.871  -4.115   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       4.214  -3.353   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       5.204  -5.444   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.235  -6.589   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       5.759  -8.053   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       4.252  -8.374   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       3.735  -9.894   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       4.807 -10.983   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       6.298 -10.595   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       7.378 -11.693   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.869 -11.306   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       9.949 -12.403   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       6.968 -13.177   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       8.049 -14.275   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       5.477 -13.564   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       5.067 -15.049   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       4.397 -12.467   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       2.906 -12.854   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       3.222  -7.229   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       1.775  -7.962   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       0.801  -9.219   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       3.698  -5.764   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       2.453  -4.681   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   27  N   UNK     0       1.334  -2.310   0.000  0.00  0.00           N+0
HETATM   28  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       7.844   0.351   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0       8.427  -2.922   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      -0.265  -2.890   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0      -1.771  -2.446   0.000  0.00  0.00           O+0
HETATM   40  C   UNK     0      -1.392  -4.090   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   24                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   21                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   19                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   15                                                  
CONECT   13   12   14                                                       
CONECT   14   13                                                            
CONECT   15   12   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   10   20                                                  
CONECT   20   19                                                            
CONECT   21    8   22   24                                                  
CONECT   22   21   23                                                       
CONECT   23   22                                                            
CONECT   24   21    5   25                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27   37                                                  
CONECT   27   26   28   38                                                  
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   31   37                                                  
CONECT   31   30   32                                                       
CONECT   32   31   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32   35   36                                                  
CONECT   35   34                                                            
CONECT   36   34   37                                                       
CONECT   37   36   26   30                                                  
CONECT   38   27   39   40                                                  
CONECT   39   38                                                            
CONECT   40   38                                                            
MASTER        0    0    0    0    0    0    0    0   40    0   86    0
END

View in JSmol

Synonyms

Value	Source
Methyl 4-[(2-acetyl-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinolin-1-yl)methyl]-3-ethenyl-2-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,4-dihydro-2H-pyran-5-carboxylic acid	Generator

Chemical Formula

C₂₇H₃₅NO₁₂

Average Mass

565.5720 Da

Monoisotopic Mass

565.21593 Da

IUPAC Name

methyl 4-[(2-acetyl-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinolin-1-yl)methyl]-3-ethenyl-2-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,4-dihydro-2H-pyran-5-carboxylate

Traditional Name

methyl 4-[(2-acetyl-6,7-dihydroxy-3,4-dihydro-1H-isoquinolin-1-yl)methyl]-5-ethenyl-6-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5,6-dihydro-4H-pyran-3-carboxylate

CAS Registry Number

Not Available

SMILES

COC(=O)C1=COC(OC2OC(CO)C(O)C(O)C2O)C(C=C)C1CC1N(CCC2=CC(O)=C(O)C=C12)C(C)=O

InChI Identifier

InChI=1S/C27H35NO12/c1-4-14-16(8-18-15-9-20(32)19(31)7-13(15)5-6-28(18)12(2)30)17(25(36)37-3)11-38-26(14)40-27-24(35)23(34)22(33)21(10-29)39-27/h4,7,9,11,14,16,18,21-24,26-27,29,31-35H,1,5-6,8,10H2,2-3H3

InChI Key

QISXROCIXKXUPS-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
Cephaelis ipecacuanha	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as terpene glycosides. These are prenol lipids containing a carbohydrate moiety glycosidically bound to a terpene backbone.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene glycosides

Direct Parent

Terpene glycosides

Alternative Parents

Substituents

Terpene glycoside
Glycosyl compound
Secoiridoid-skeleton
O-glycosyl compound
Aromatic monoterpenoid
Bicyclic monoterpenoid
Monoterpenoid
Tetrahydroisoquinoline
1-hydroxy-2-unsubstituted benzenoid
Sugar acid
Monosaccharide
Oxane
Benzenoid
Enoate ester
Methyl ester
Acetamide
Alpha,beta-unsaturated carboxylic ester
Tertiary carboxylic acid amide
Vinylogous ester
Carboxamide group
Carboxylic acid ester
Secondary alcohol
Organoheterocyclic compound
Polyol
Acetal
Azacycle
Oxacycle
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Primary alcohol
Organic oxide
Organopnictogen compound
Alcohol
Hydrocarbon derivative
Organonitrogen compound
Carbonyl group
Organic oxygen compound
Organic nitrogen compound
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	0.22	ALOGPS
logP	-0.5	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Acidic)	9.19	ChemAxon
pKa (Strongest Basic)	-1.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	195.68 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	137.26 m³·mol⁻¹	ChemAxon
Polarizability	56.29 Å³	ChemAxon
Number of Rings	4	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

4589272

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for methyl 4-[(2-acetyl-6,7-dihydroxy-3,4-dihydro-1h-isoquinolin-1-yl)methyl]-5-ethenyl-6-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5,6-dihydro-4h-pyran-3-carboxylate (NP0197174)

MOL for NP0197174 (methyl 4-[(2-acetyl-6,7-dihydroxy-3,4-dihydro-1h-isoquinolin-1-yl)methyl]-5-ethenyl-6-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5,6-dihydro-4h-pyran-3-carboxylate)

3D MOL for NP0197174 (methyl 4-[(2-acetyl-6,7-dihydroxy-3,4-dihydro-1h-isoquinolin-1-yl)methyl]-5-ethenyl-6-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5,6-dihydro-4h-pyran-3-carboxylate)

3D SDF for NP0197174 (methyl 4-[(2-acetyl-6,7-dihydroxy-3,4-dihydro-1h-isoquinolin-1-yl)methyl]-5-ethenyl-6-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5,6-dihydro-4h-pyran-3-carboxylate)

3D-SDF for NP0197174 (methyl 4-[(2-acetyl-6,7-dihydroxy-3,4-dihydro-1h-isoquinolin-1-yl)methyl]-5-ethenyl-6-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5,6-dihydro-4h-pyran-3-carboxylate)

PDB for NP0197174 (methyl 4-[(2-acetyl-6,7-dihydroxy-3,4-dihydro-1h-isoquinolin-1-yl)methyl]-5-ethenyl-6-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5,6-dihydro-4h-pyran-3-carboxylate)

3D PDB for NP0197174 (methyl 4-[(2-acetyl-6,7-dihydroxy-3,4-dihydro-1h-isoquinolin-1-yl)methyl]-5-ethenyl-6-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5,6-dihydro-4h-pyran-3-carboxylate)

SMILES for NP0197174 (methyl 4-[(2-acetyl-6,7-dihydroxy-3,4-dihydro-1h-isoquinolin-1-yl)methyl]-5-ethenyl-6-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5,6-dihydro-4h-pyran-3-carboxylate)

INCHI for NP0197174 (methyl 4-[(2-acetyl-6,7-dihydroxy-3,4-dihydro-1h-isoquinolin-1-yl)methyl]-5-ethenyl-6-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5,6-dihydro-4h-pyran-3-carboxylate)

Structure for NP0197174 (methyl 4-[(2-acetyl-6,7-dihydroxy-3,4-dihydro-1h-isoquinolin-1-yl)methyl]-5-ethenyl-6-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5,6-dihydro-4h-pyran-3-carboxylate)

3D Structure for NP0197174 (methyl 4-[(2-acetyl-6,7-dihydroxy-3,4-dihydro-1h-isoquinolin-1-yl)methyl]-5-ethenyl-6-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5,6-dihydro-4h-pyran-3-carboxylate)