NP-MRD: Showing NP-Card for deacetylipecoside (NP0267923)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-08 12:51:59 UTC

Updated at

2022-09-08 12:51:59 UTC

NP-MRD ID

NP0267923

Secondary Accession Numbers

None

Natural Product Identification

Common Name

deacetylipecoside

Description

Deacetylipecoside 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. deacetylipecoside is found in Apis cerana. deacetylipecoside was first documented in 2008 (PMID: 18927081). Based on a literature review very few articles have been published on deacetylipecoside.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309082214522D          

 37 40  0  0  1  0            999 V2000
   -0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7145   -2.8875    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4289   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -2.8875    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1434   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -4.1250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8579   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -5.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -3.7125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.2868   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -2.8875    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.2868   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -2.4750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.8579   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  1  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
    4.2868   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    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
  1  2  2  0  0  0  0
  3  2  1  6  0  0  0
  3  4  1  0  0  0  0
  4  5  1  1  0  0  0
  6  5  1  6  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  6  0  0  0
  9 10  1  0  0  0  0
  8 11  1  0  0  0  0
 11 12  1  1  0  0  0
 11 13  1  0  0  0  0
 13 14  1  6  0  0  0
 13 15  1  0  0  0  0
  6 15  1  0  0  0  0
 15 16  1  1  0  0  0
  4 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
 22 23  1  0  0  0  0
 19 24  1  0  0  0  0
  3 24  1  0  0  0  0
 24 25  1  6  0  0  0
 26 25  1  1  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
 30 37  1  0  0  0  0
 26 37  1  0  0  0  0
M  END

     RDKit          3D

 70 73  0  0  0  0  0  0  0  0999 V2000
    1.0603    2.8725   -2.9031 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2412    1.9672   -2.3621 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5781    1.1050   -1.2089 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9071    1.6922   -0.6756 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1543    0.9864    0.5037 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3667    0.2805    0.4415 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0456   -1.0560    0.6084 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1163   -1.8439    0.9738 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5696   -3.2577    1.1828 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9891   -3.7330   -0.0102 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7353   -1.4201    2.2869 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.1021   -1.2344    2.0736 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1698   -0.0743    2.7163 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8456   -0.1930    3.1203 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2695    0.8317    1.4893 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.6064    0.8681    1.0875 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6849    3.0398   -0.3027 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4026    3.5008   -0.1776 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7003    2.7171   -0.0402 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9919    3.3467    0.0855 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0992    2.8155    0.2379 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0460    4.7583    0.0330 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2685    5.4624    0.1474 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3834    1.2840   -0.0279 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4126    0.2717    0.0622 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4596   -0.0063   -0.8969 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.9913   -0.3941   -2.2289 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1472   -0.3587   -3.0993 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9795   -1.5653   -2.8330 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8515   -1.9933   -1.4345 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4946   -3.1840   -1.0860 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4441   -3.6864    0.1935 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1017   -4.8889    0.5172 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7399   -2.9881    1.1394 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6731   -3.4714    2.4343 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0968   -1.7963    0.7882 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1434   -1.2999   -0.4638 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625    3.0791   -2.5617 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7494    3.4836   -3.7609 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7401    1.9239   -2.8651 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8264    0.0754   -1.4326 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7021    1.5539   -1.4041 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8002    0.4908   -0.5619 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8578   -1.8990    0.1502 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3523   -3.9710    1.4507 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7719   -3.2717    1.9439 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1408   -4.1997    0.1687 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6137   -2.1838    3.0834 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6252   -1.6473    2.8185 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7633    0.3207    3.5456 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6816   -1.0909    3.5088 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9532    1.8629    1.7695 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1727    1.0923    1.8622 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2404    4.5631   -0.1872 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3658    6.0042    1.0996 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3094    6.1625   -0.7342 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1185    4.7486   -0.0146 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2829    1.1474    0.8819 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9605   -0.7390    0.3474 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9641    0.5101    1.0482 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2928    0.6623   -1.0621 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5400   -1.3237   -2.2293 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8822   -0.2163   -4.1568 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7624    0.5385   -2.8033 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6142   -2.3782   -3.5233 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0500   -1.4251   -3.0873 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0609   -3.7494   -1.8384 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0373   -5.2195    1.4689 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1463   -2.9469    3.1372 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5720   -1.3122    1.5662 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 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  2  0
 31 32  1  0
 32 33  1  0
 32 34  2  0
 34 35  1  0
 34 36  1  0
 36 37  2  0
 24 19  1  0
 37 26  1  0
 15  6  1  0
 37 30  1  0
 23 55  1  0
 23 56  1  0
 23 57  1  0
 18 54  1  0
  4 42  1  6
  6 43  1  6
  8 44  1  6
  9 45  1  0
  9 46  1  0
 10 47  1  0
 11 48  1  1
 12 49  1  0
 13 50  1  1
 14 51  1  0
 15 52  1  1
 16 53  1  0
  3 41  1  6
  2 40  1  0
  1 38  1  0
  1 39  1  0
 24 58  1  1
 25 59  1  0
 25 60  1  0
 26 61  1  6
 27 62  1  0
 28 63  1  0
 28 64  1  0
 29 65  1  0
 29 66  1  0
 31 67  1  0
 33 68  1  0
 35 69  1  0
 36 70  1  0
M  END


  Mrv1652309082214522D          

 37 40  0  0  1  0            999 V2000
   -0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7145   -2.8875    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4289   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -2.8875    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1434   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -4.1250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8579   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -5.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -3.7125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.2868   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -2.8875    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.2868   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -2.4750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.8579   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  1  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
    4.2868   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    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
  1  2  2  0  0  0  0
  3  2  1  6  0  0  0
  3  4  1  0  0  0  0
  4  5  1  1  0  0  0
  6  5  1  6  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  6  0  0  0
  9 10  1  0  0  0  0
  8 11  1  0  0  0  0
 11 12  1  1  0  0  0
 11 13  1  0  0  0  0
 13 14  1  6  0  0  0
 13 15  1  0  0  0  0
  6 15  1  0  0  0  0
 15 16  1  1  0  0  0
  4 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
 22 23  1  0  0  0  0
 19 24  1  0  0  0  0
  3 24  1  0  0  0  0
 24 25  1  6  0  0  0
 26 25  1  1  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
 30 37  1  0  0  0  0
 26 37  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0267923

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)C1=CO[C@@H](O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)[C@H](C=C)[C@@H]1C[C@H]1NCCC2=CC(O)=C(O)C=C12

> <INCHI_IDENTIFIER>
InChI=1S/C25H33NO11/c1-3-12-14(7-16-13-8-18(29)17(28)6-11(13)4-5-26-16)15(23(33)34-2)10-35-24(12)37-25-22(32)21(31)20(30)19(9-27)36-25/h3,6,8,10,12,14,16,19-22,24-32H,1,4-5,7,9H2,2H3/t12-,14+,16-,19-,20-,21+,22-,24+,25+/m1/s1

> <INCHI_KEY>
MTAVTRZTGFLKSC-MDXCLUIBSA-N

> <FORMULA>
C25H33NO11

> <MOLECULAR_WEIGHT>
523.535

> <EXACT_MASS>
523.205360887

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_ATOM_COUNT>
70

> <JCHEM_AVERAGE_POLARIZABILITY>
53.30120476797289

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <JCHEM_LOGP>
-0.4953218893567712

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
12.114250764448235

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.576337081208216

> <JCHEM_PKA_STRONGEST_BASIC>
8.65605913456705

> <JCHEM_POLAR_SURFACE_AREA>
187.4

> <JCHEM_REFRACTIVITY>
127.69559999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
deacetylipecoside

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 08-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   08-SEP-22         0                                  
HETATM    1  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      -2.667  -4.620   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      -4.001  -5.390   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -4.001  -6.930   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -5.335  -7.700   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -5.335  -9.240   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      -6.668 -10.010   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      -6.668  -6.930   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -8.002  -7.700   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      -6.668  -5.390   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      -8.002  -4.620   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      -5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -5.335  -3.080   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0      -1.334  -6.930   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       0.000  -7.700   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.667  -7.700   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       2.667  -9.240   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       4.001  -6.930   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       2.667  -4.620   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       8.002  -0.000   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       8.002  -3.080   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
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   24                                                  
CONECT    4    3    5   17                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7   15                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   11                                                  
CONECT    9    8   10                                                       
CONECT   10    9                                                            
CONECT   11    8   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13    6   16                                                  
CONECT   16   15                                                            
CONECT   17    4   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   24                                                  
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23                                                       
CONECT   23   22                                                            
CONECT   24   19    3   25                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27   37                                                  
CONECT   27   26   28                                                       
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   30   26                                                  
MASTER        0    0    0    0    0    0    0    0   37    0   80    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₅H₃₃NO₁₁

Average Mass

523.5350 Da

Monoisotopic Mass

523.20536 Da

IUPAC Name

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

Traditional Name

deacetylipecoside

CAS Registry Number

Not Available

SMILES

COC(=O)C1=CO[C@@H](O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)[C@H](C=C)[C@@H]1C[C@H]1NCCC2=CC(O)=C(O)C=C12

InChI Identifier

InChI=1S/C25H33NO11/c1-3-12-14(7-16-13-8-18(29)17(28)6-11(13)4-5-26-16)15(23(33)34-2)10-35-24(12)37-25-22(32)21(31)20(30)19(9-27)36-25/h3,6,8,10,12,14,16,19-22,24-32H,1,4-5,7,9H2,2H3/t12-,14+,16-,19-,20-,21+,22-,24+,25+/m1/s1

InChI Key

MTAVTRZTGFLKSC-MDXCLUIBSA-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
Apis cerana	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
O-glycosyl compound
Secoiridoid-skeleton
Glycosyl compound
Tetrahydroisoquinoline
Monoterpenoid
Aromatic monoterpenoid
Bicyclic monoterpenoid
Aralkylamine
1-hydroxy-2-unsubstituted benzenoid
Sugar acid
Benzenoid
Oxane
Monosaccharide
Vinylogous ester
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Methyl ester
Secondary alcohol
Amino acid or derivatives
Carboxylic acid ester
Acetal
Carboxylic acid derivative
Secondary aliphatic amine
Oxacycle
Monocarboxylic acid or derivatives
Azacycle
Organoheterocyclic compound
Secondary amine
Polyol
Hydrocarbon derivative
Amine
Organic oxide
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Carbonyl group
Organonitrogen compound
Organooxygen compound
Primary alcohol
Alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

beta-D-glucoside (CHEBI:18106 )
methyl ester (CHEBI:18106 )
isoquinoline alkaloid (CHEBI:18106 )
Isoquinoline alkaloids (C07307 )

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	-0.5	ChemAxon
pKa (Strongest Acidic)	9.58	ChemAxon
pKa (Strongest Basic)	8.66	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	187.4 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	127.7 m³·mol⁻¹	ChemAxon
Polarizability	53.3 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

C00051867

Chemspider ID

390030

KEGG Compound ID

C07307

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

441259

PDB ID

Not Available

ChEBI ID

18106

Good Scents ID

Not Available

References

General References

Nomura T, Quesada AL, Kutchan TM: The new beta-D-glucosidase in terpenoid-isoquinoline alkaloid biosynthesis in Psychotria ipecacuanha. J Biol Chem. 2008 Dec 12;283(50):34650-9. doi: 10.1074/jbc.M806953200. Epub 2008 Oct 16. [PubMed:18927081 ]
LOTUS database [Link]

Showing NP-Card for deacetylipecoside (NP0267923)

MOL for NP0267923 (deacetylipecoside)

3D MOL for NP0267923 (deacetylipecoside)

3D SDF for NP0267923 (deacetylipecoside)

3D-SDF for NP0267923 (deacetylipecoside)

PDB for NP0267923 (deacetylipecoside)

3D PDB for NP0267923 (deacetylipecoside)

SMILES for NP0267923 (deacetylipecoside)

INCHI for NP0267923 (deacetylipecoside)

Structure for NP0267923 (deacetylipecoside)

3D Structure for NP0267923 (deacetylipecoside)