NP-MRD: Showing NP-Card for (1r,4ar,5s,6r,8as)-5-hydroxy-6-(3-methoxy-3-oxoprop-1-en-2-yl)-8a-methyl-4-({[(2r,4s,5s,6s)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)-octahydro-1h-naphthalen-1-yl 2-hydroxy-3-methylbutanoate (NP0246838)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-07 08:25:49 UTC

Updated at

2022-09-07 08:25:49 UTC

NP-MRD ID

NP0246838

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r,4ar,5s,6r,8as)-5-hydroxy-6-(3-methoxy-3-oxoprop-1-en-2-yl)-8a-methyl-4-({[(2r,4s,5s,6s)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)-octahydro-1h-naphthalen-1-yl 2-hydroxy-3-methylbutanoate

Description

Ixerisoside J 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. (1r,4ar,5s,6r,8as)-5-hydroxy-6-(3-methoxy-3-oxoprop-1-en-2-yl)-8a-methyl-4-({[(2r,4s,5s,6s)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)-octahydro-1h-naphthalen-1-yl 2-hydroxy-3-methylbutanoate is found in Ixeris repens. Based on a literature review very few articles have been published on Ixerisoside J.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309072210252D          

 39 41  0  0  1  0            999 V2000
   -2.8579    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    3.3000    0.0000 O   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
   -2.1434    1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4289    0.8250    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  2  0  0  0  0  0  0  0  0  0
   -1.4289   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4289   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 O   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 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -1.6500    0.0000 C   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
   -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 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7158   -0.0000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.4302   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1447   -0.0000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -7.8592   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8592   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1447    0.8250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -7.8592    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4302    1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.4302    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7158    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    0.0000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.8579    0.8250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.5724    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  7  2  1  1  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  1  0  0  0
 10 12  1  0  0  0  0
 12 13  1  6  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
 12 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 26 25  1  6  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  1  0  0  0
 29 30  1  0  0  0  0
 28 31  1  0  0  0  0
 31 32  1  1  0  0  0
 31 33  1  0  0  0  0
 33 34  1  6  0  0  0
 33 35  1  0  0  0  0
 26 35  1  0  0  0  0
 35 36  1  0  0  0  0
 37 23  1  1  0  0  0
 10 37  1  0  0  0  0
 37 38  1  0  0  0  0
  7 38  1  0  0  0  0
 38 39  1  1  0  0  0
M  END

     RDKit          3D

 83 85  0  0  0  0  0  0  0  0999 V2000
   -1.9990    4.6004   -0.4602 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0186    4.0092    0.1903 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1586    4.8509    0.5121 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1505    4.3801    1.1369 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2146    6.1646    0.1458 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2993    7.0230    0.4177 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0351    2.5838    0.6131 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.3361    1.8853    0.4290 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5166    1.1840   -0.8827 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4173    0.1998   -1.2183 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0835    0.3692   -2.6582 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9634   -1.1937   -1.0314 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.2649   -1.1210   -0.4364 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4124   -1.5712   -1.0100 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3546   -2.0957   -2.1495 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7344   -1.4715   -0.3505 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.5705   -0.8564    0.9080 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3067   -2.8458   -0.0724 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4040   -3.6595    0.8371 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6214   -3.6009   -1.3320 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1532   -2.0650   -0.1541 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3417   -1.9803   -0.3146 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8515   -0.5480   -0.3788 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7589   -0.3991   -1.5162 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8788   -1.2036   -1.4642 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7458   -1.0030   -0.4305 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.9847   -0.6679   -1.0140 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9873   -0.4337   -0.1136 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.0379    0.9991    0.4010 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9001    1.4020    1.0460 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1044   -1.3998    1.0148 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.6893   -0.7221    2.1059 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8200   -1.9835    1.5034 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.0993   -3.1244    2.2439 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9819   -2.3104    0.2835 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.8030   -3.0684   -0.5875 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2859    0.3711   -0.2471 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1036    1.8062   -0.0222 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4899    2.4765   -1.1431 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8914    5.6439   -0.7170 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9225    4.1510   -0.7746 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8939    7.8368    1.0788 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6610    7.4861   -0.5322 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1391    6.4968    0.9098 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8706    2.6352    1.7366 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1603    2.6291    0.5124 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5178    1.1883    1.2887 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5279    0.7254   -0.8684 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5952    1.9799   -1.6791 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0042    0.8019   -3.1588 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3034    1.1276   -2.8747 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9458   -0.5912   -3.2008 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1560   -1.6921   -2.0288 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4605   -0.9298   -0.9669 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4972   -0.5874    1.1870 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2664   -2.6839    0.4697 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8726   -4.4634    0.2876 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0118   -4.1847    1.6278 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6735   -3.0147    1.3626 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6319   -2.9578   -2.2300 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6222   -4.0896   -1.2915 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8892   -4.4358   -1.4987 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3824   -1.9048    0.9375 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4297   -3.1274   -0.3645 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7529   -2.5223    0.5744 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6393   -2.5789   -1.1988 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4664   -0.4215    0.5660 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3245   -0.5794   -2.5187 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1591    0.6599   -1.5895 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4306   -0.2277    0.2820 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9507   -0.5309   -0.7067 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8799    1.0440    1.1233 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3229    1.6650   -0.4417 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8641    1.2184    2.0034 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7591   -2.2538    0.7122 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5015   -1.2131    2.3854 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2265   -1.2884    2.1278 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6325   -3.8964    1.8594 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0695   -2.8715    0.5359 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4675   -3.9826   -0.6870 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7692    0.0868    0.7503 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9405    1.8052    0.6996 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3967    2.8676   -1.1210 H   0  0  0  0  0  0  0  0  0  0  0  0
  6  5  1  0
  5  3  1  0
  3  4  2  0
  3  2  1  0
  2  1  2  3
  2  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  6
 10 12  1  0
 12 21  1  0
 21 22  1  0
 22 23  1  0
 23 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
 28 31  1  0
 31 32  1  0
 31 33  1  0
 33 34  1  0
 33 35  1  0
 35 36  1  0
 23 37  1  0
 37 38  1  0
 38 39  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
 18 20  1  0
 38  7  1  0
 37 10  1  0
 35 26  1  0
  6 42  1  0
  6 43  1  0
  6 44  1  0
  1 40  1  0
  1 41  1  0
  7 45  1  1
  8 46  1  0
  8 47  1  0
  9 48  1  0
  9 49  1  0
 11 50  1  0
 11 51  1  0
 11 52  1  0
 12 53  1  6
 21 63  1  0
 21 64  1  0
 22 65  1  0
 22 66  1  0
 23 67  1  1
 24 68  1  0
 24 69  1  0
 26 70  1  1
 28 71  1  6
 29 72  1  0
 29 73  1  0
 30 74  1  0
 31 75  1  6
 32 76  1  0
 33 77  1  1
 34 78  1  0
 35 79  1  1
 36 80  1  0
 37 81  1  1
 38 82  1  1
 39 83  1  0
 16 54  1  6
 17 55  1  0
 18 56  1  0
 19 57  1  0
 19 58  1  0
 19 59  1  0
 20 60  1  0
 20 61  1  0
 20 62  1  0
M  END


  Mrv1652309072210252D          

 39 41  0  0  1  0            999 V2000
   -2.8579    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    3.3000    0.0000 O   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
   -2.1434    1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4289    0.8250    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  2  0  0  0  0  0  0  0  0  0
   -1.4289   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4289   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 O   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 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -1.6500    0.0000 C   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
   -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 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7158   -0.0000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.4302   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1447   -0.0000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -7.8592   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8592   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1447    0.8250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -7.8592    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4302    1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.4302    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7158    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    0.0000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.8579    0.8250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.5724    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  7  2  1  1  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  1  0  0  0
 10 12  1  0  0  0  0
 12 13  1  6  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
 12 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 26 25  1  6  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  1  0  0  0
 29 30  1  0  0  0  0
 28 31  1  0  0  0  0
 31 32  1  1  0  0  0
 31 33  1  0  0  0  0
 33 34  1  6  0  0  0
 33 35  1  0  0  0  0
 26 35  1  0  0  0  0
 35 36  1  0  0  0  0
 37 23  1  1  0  0  0
 10 37  1  0  0  0  0
 37 38  1  0  0  0  0
  7 38  1  0  0  0  0
 38 39  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0246838

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)C(=C)[C@H]1CC[C@]2(C)[C@@H](CCC(CO[C@@H]3O[C@@H](CO)[C@@H](O)[C@H](O)C3O)[C@H]2[C@H]1O)OC(=O)C(O)C(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C27H44O12/c1-12(2)19(29)25(35)39-17-7-6-14(11-37-26-23(33)22(32)21(31)16(10-28)38-26)18-20(30)15(8-9-27(17,18)4)13(3)24(34)36-5/h12,14-23,26,28-33H,3,6-11H2,1-2,4-5H3/t14?,15-,16+,17-,18+,19?,20+,21-,22+,23?,26-,27-/m1/s1

> <INCHI_KEY>
WZQRTEWYMMHGLI-YMMSZFTFSA-N

> <FORMULA>
C27H44O12

> <MOLECULAR_WEIGHT>
560.637

> <EXACT_MASS>
560.283276857

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
83

> <JCHEM_AVERAGE_POLARIZABILITY>
58.26777444442821

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,4aR,5S,6R,8aS)-5-hydroxy-6-(3-methoxy-3-oxoprop-1-en-2-yl)-8a-methyl-4-({[(2R,4S,5S,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)-decahydronaphthalen-1-yl 2-hydroxy-3-methylbutanoate

> <JCHEM_LOGP>
-0.015236976999998347

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.592559805209152

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.025943813723664

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9810834118053284

> <JCHEM_POLAR_SURFACE_AREA>
192.43999999999997

> <JCHEM_REFRACTIVITY>
134.7279

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(1R,4aR,5S,6R,8aS)-5-hydroxy-6-(3-methoxy-3-oxoprop-1-en-2-yl)-8a-methyl-4-({[(2R,4S,5S,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)-octahydro-1H-naphthalen-1-yl 2-hydroxy-3-methylbutanoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 07-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-SEP-22         0                                  
HETATM    1  C   UNK     0      -5.335   4.620   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -4.001   3.850   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.667   4.620   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      -1.334   3.850   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0      -2.667   6.160   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      -1.334   6.930   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -4.001   2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.667   1.540   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.667   0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -2.667  -1.540   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -2.667  -3.080   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -1.334  -0.770   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      -0.000  -3.080   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       0.000  -4.620   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -8.002  -0.000   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      -9.336  -0.770   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0     -10.669  -0.000   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0     -12.003  -0.770   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0     -13.337  -0.000   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0     -14.670  -0.770   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0     -14.670  -2.310   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0     -13.337   1.540   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0     -14.670   2.310   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0     -12.003   2.310   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0     -12.003   3.850   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0     -10.669   1.540   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0      -9.336   2.310   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0      -5.335   0.000   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      -5.335   1.540   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0      -6.668   2.310   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    7                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5                                                            
CONECT    7    2    8   38                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   12   37                                             
CONECT   11   10                                                            
CONECT   12   10   13   21                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18                                                            
CONECT   21   12   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24   37                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27   35                                                  
CONECT   27   26   28                                                       
CONECT   28   27   29   31                                                  
CONECT   29   28   30                                                       
CONECT   30   29                                                            
CONECT   31   28   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33   26   36                                                  
CONECT   36   35                                                            
CONECT   37   23   10   38                                                  
CONECT   38   37    7   39                                                  
CONECT   39   38                                                            
MASTER        0    0    0    0    0    0    0    0   39    0   82    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₇H₄₄O₁₂

Average Mass

560.6370 Da

Monoisotopic Mass

560.28328 Da

IUPAC Name

(1R,4aR,5S,6R,8aS)-5-hydroxy-6-(3-methoxy-3-oxoprop-1-en-2-yl)-8a-methyl-4-({[(2R,4S,5S,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)-decahydronaphthalen-1-yl 2-hydroxy-3-methylbutanoate

Traditional Name

(1R,4aR,5S,6R,8aS)-5-hydroxy-6-(3-methoxy-3-oxoprop-1-en-2-yl)-8a-methyl-4-({[(2R,4S,5S,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)-octahydro-1H-naphthalen-1-yl 2-hydroxy-3-methylbutanoate

CAS Registry Number

Not Available

SMILES

COC(=O)C(=C)[C@H]1CC[C@]2(C)[C@@H](CCC(CO[C@@H]3O[C@@H](CO)[C@@H](O)[C@H](O)C3O)[C@H]2[C@H]1O)OC(=O)C(O)C(C)C

InChI Identifier

InChI=1S/C27H44O12/c1-12(2)19(29)25(35)39-17-7-6-14(11-37-26-23(33)22(32)21(31)16(10-28)38-26)18-20(30)15(8-9-27(17,18)4)13(3)24(34)36-5/h12,14-23,26,28-33H,3,6-11H2,1-2,4-5H3/t14?,15-,16+,17-,18+,19?,20+,21-,22+,23?,26-,27-/m1/s1

InChI Key

WZQRTEWYMMHGLI-YMMSZFTFSA-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
Ixeris repens	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
Sesquiterpenoid
Eudesmane, isoeudesmane or cycloeudesmane sesquiterpenoid
Hexose monosaccharide
O-glycosyl compound
Glycosyl compound
Fatty acid ester
Fatty acyl
Oxane
Monosaccharide
Dicarboxylic acid or derivatives
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Methyl ester
Cyclic alcohol
Secondary alcohol
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Polyol
Carboxylic acid derivative
Acetal
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
Carbonyl group
Alcohol
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic 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	-0.015	ChemAxon
pKa (Strongest Acidic)	12.03	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	192.44 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	134.73 m³·mol⁻¹	ChemAxon
Polarizability	58.27 Å³	ChemAxon
Number of Rings	3	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

C00033985

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

101589327

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1r,4ar,5s,6r,8as)-5-hydroxy-6-(3-methoxy-3-oxoprop-1-en-2-yl)-8a-methyl-4-({[(2r,4s,5s,6s)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)-octahydro-1h-naphthalen-1-yl 2-hydroxy-3-methylbutanoate (NP0246838)

MOL for NP0246838 ((1r,4ar,5s,6r,8as)-5-hydroxy-6-(3-methoxy-3-oxoprop-1-en-2-yl)-8a-methyl-4-({[(2r,4s,5s,6s)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)-octahydro-1h-naphthalen-1-yl 2-hydroxy-3-methylbutanoate)

3D MOL for NP0246838 ((1r,4ar,5s,6r,8as)-5-hydroxy-6-(3-methoxy-3-oxoprop-1-en-2-yl)-8a-methyl-4-({[(2r,4s,5s,6s)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)-octahydro-1h-naphthalen-1-yl 2-hydroxy-3-methylbutanoate)

3D SDF for NP0246838 ((1r,4ar,5s,6r,8as)-5-hydroxy-6-(3-methoxy-3-oxoprop-1-en-2-yl)-8a-methyl-4-({[(2r,4s,5s,6s)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)-octahydro-1h-naphthalen-1-yl 2-hydroxy-3-methylbutanoate)

3D-SDF for NP0246838 ((1r,4ar,5s,6r,8as)-5-hydroxy-6-(3-methoxy-3-oxoprop-1-en-2-yl)-8a-methyl-4-({[(2r,4s,5s,6s)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)-octahydro-1h-naphthalen-1-yl 2-hydroxy-3-methylbutanoate)

PDB for NP0246838 ((1r,4ar,5s,6r,8as)-5-hydroxy-6-(3-methoxy-3-oxoprop-1-en-2-yl)-8a-methyl-4-({[(2r,4s,5s,6s)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)-octahydro-1h-naphthalen-1-yl 2-hydroxy-3-methylbutanoate)

3D PDB for NP0246838 ((1r,4ar,5s,6r,8as)-5-hydroxy-6-(3-methoxy-3-oxoprop-1-en-2-yl)-8a-methyl-4-({[(2r,4s,5s,6s)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)-octahydro-1h-naphthalen-1-yl 2-hydroxy-3-methylbutanoate)

SMILES for NP0246838 ((1r,4ar,5s,6r,8as)-5-hydroxy-6-(3-methoxy-3-oxoprop-1-en-2-yl)-8a-methyl-4-({[(2r,4s,5s,6s)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)-octahydro-1h-naphthalen-1-yl 2-hydroxy-3-methylbutanoate)

INCHI for NP0246838 ((1r,4ar,5s,6r,8as)-5-hydroxy-6-(3-methoxy-3-oxoprop-1-en-2-yl)-8a-methyl-4-({[(2r,4s,5s,6s)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)-octahydro-1h-naphthalen-1-yl 2-hydroxy-3-methylbutanoate)

Structure for NP0246838 ((1r,4ar,5s,6r,8as)-5-hydroxy-6-(3-methoxy-3-oxoprop-1-en-2-yl)-8a-methyl-4-({[(2r,4s,5s,6s)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)-octahydro-1h-naphthalen-1-yl 2-hydroxy-3-methylbutanoate)

3D Structure for NP0246838 ((1r,4ar,5s,6r,8as)-5-hydroxy-6-(3-methoxy-3-oxoprop-1-en-2-yl)-8a-methyl-4-({[(2r,4s,5s,6s)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)-octahydro-1h-naphthalen-1-yl 2-hydroxy-3-methylbutanoate)