NP-MRD: Showing NP-Card for (1s,4as,7s,7as)-4-({[(2r,3r,4s,5s,6r)-3-(acetyloxy)-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)-7-(hydroxymethyl)-1h,4ah,5h,6h,7h,7ah-cyclopenta[c]pyran-1-yl 3-methylbutanoate (NP0223023)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-06 01:00:35 UTC

Updated at

2022-09-06 01:00:35 UTC

NP-MRD ID

NP0223023

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,4as,7s,7as)-4-({[(2r,3r,4s,5s,6r)-3-(acetyloxy)-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)-7-(hydroxymethyl)-1h,4ah,5h,6h,7h,7ah-cyclopenta[c]pyran-1-yl 3-methylbutanoate

Description

[[(1S)-1,4aalpha,5,6,7,7aalpha-Hexahydro-7alpha-(hydroxymethyl)-1alpha-(isovaleryloxy)cyclopenta[c]pyran]-4-yl]methyl 2-O-acetyl-beta-D-glucopyranoside 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. (1s,4as,7s,7as)-4-({[(2r,3r,4s,5s,6r)-3-(acetyloxy)-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)-7-(hydroxymethyl)-1h,4ah,5h,6h,7h,7ah-cyclopenta[c]pyran-1-yl 3-methylbutanoate is found in Viburnum lantana and Viburnum prunifolium. Based on a literature review very few articles have been published on [[(1S)-1,4aalpha,5,6,7,7aalpha-Hexahydro-7alpha-(hydroxymethyl)-1alpha-(isovaleryloxy)cyclopenta[c]pyran]-4-yl]methyl 2-O-acetyl-beta-D-glucopyranoside.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309062203002D          

 34 36  0  0  1  0            999 V2000
    2.1434    8.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    7.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    7.4250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    7.4250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    6.6000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1434    6.1875    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8579    6.6000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    5.3625    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8579    4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    4.9500    0.0000 C   0  0  1  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
    0.7145    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    5.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    6.1875    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0000    6.6000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    3.7125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7145    2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.8875    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
    2.1434    2.8875    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
   -1.4289    4.1250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.2136    3.8701    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.4685    3.0854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2755    2.9139    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6985    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2136    5.2049    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    4.9500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  5  4  1  6  0  0  0
  5  6  1  0  0  0  0
  6  7  1  1  0  0  0
  6  8  1  0  0  0  0
  8  9  1  6  0  0  0
  8 10  1  0  0  0  0
 10 11  1  1  0  0  0
 11 12  1  0  0  0  0
 10 13  1  0  0  0  0
 13 14  1  0  0  0  0
  5 14  1  0  0  0  0
 14 15  1  1  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  1  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  1  0  0  0  0
 20 28  1  0  0  0  0
 28 29  1  6  0  0  0
 29 30  1  1  0  0  0
 30 31  1  0  0  0  0
 29 32  1  0  0  0  0
 32 33  1  0  0  0  0
 34 33  1  6  0  0  0
 17 34  1  0  0  0  0
 28 34  1  0  0  0  0
M  END

     RDKit          3D

 70 72  0  0  0  0  0  0  0  0999 V2000
   -5.2300    4.3266   -0.9585 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9128    2.9658   -1.4631 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0002    2.7332   -2.6740 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5255    1.9624   -0.6144 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2070    0.6567   -0.9830 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.2379   -0.2626   -0.3514 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.3315   -1.4531   -1.0663 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9606   -0.4904    1.1098 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.0454   -0.2244    1.9129 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7612    0.3114    1.5592 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.4336   -0.0789    2.9941 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5547    0.2989    3.7580 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6929   -0.0373    0.7729 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8349    0.2081   -0.5705 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.5449   -0.9744   -1.2491 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4211   -0.8747   -2.0366 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1833   -0.5381   -1.2459 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4975    0.5705   -1.5106 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6313    0.8539   -0.7685 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5238   -0.2476   -0.5278 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5734    0.1726    0.3278 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9043    0.2187   -0.0547 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1698   -0.1411   -1.2449 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9817    0.6622    0.8604 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3445    2.1038    0.6468 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1009    2.9365    0.9053 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8321    2.3903   -0.7553 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7830   -1.4069    0.0391 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2292   -2.7151   -0.5814 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5321   -3.2234   -0.0133 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6710   -4.5427   -0.4946 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1418   -3.6581   -0.0557 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1089   -2.8485   -0.3205 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3067   -1.4053   -0.1629 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.1151    4.3407    0.1577 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5668    5.0977   -1.3681 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3069    4.4967   -1.1588 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3029    0.5034   -2.0923 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2205    0.2561   -0.4317 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9091   -1.3529   -1.8738 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6523   -1.5731    1.2004 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8487   -0.6234    1.4525 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9457    1.3963    1.5744 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5933    0.5414    3.3756 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2588   -1.1637    3.1029 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9326    1.1565    3.4342 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0499    0.9459   -0.8568 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2209   -1.7869   -2.6274 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5662   -0.0655   -2.7827 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1145    1.2077   -2.3158 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0100   -0.5177   -1.4871 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6911    0.5395    1.9102 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8515    0.0060    0.6756 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1387    2.3598    1.3688 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4434    2.3877    1.5978 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5174    3.1121   -0.0160 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4056    3.9349    1.2748 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8295    1.4952   -1.3974 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1797    3.1466   -1.2476 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8599    2.8201   -0.7486 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0499   -1.4872    1.1296 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2668   -2.6806   -1.6734 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4482   -3.2615    1.0763 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3929   -2.6129   -0.3331 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0835   -5.1320    0.1685 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3299   -3.7719    1.0360 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1505   -4.6218   -0.5930 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9052   -3.1472    0.4014 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4573   -3.1239   -1.3140 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1475   -1.0709    0.8174 H   0  0  0  0  0  0  0  0  0  0  0  0
 26 25  1  0
 25 27  1  0
 25 24  1  0
 24 22  1  0
 22 23  2  0
 22 21  1  0
 21 20  1  0
 20 19  1  0
 19 18  1  0
 18 17  2  0
 17 16  1  0
 16 15  1  0
 15 14  1  0
 14 13  1  0
 13 10  1  0
 10 11  1  0
 11 12  1  0
 10  8  1  0
  8  9  1  0
  8  6  1  0
  6  7  1  0
  6  5  1  0
  5  4  1  0
  4  2  1  0
  2  1  1  0
  2  3  2  0
 17 34  1  0
 34 33  1  0
 33 32  1  0
 32 29  1  0
 29 30  1  0
 30 31  1  0
 29 28  1  0
 28 20  1  0
  5 14  1  0
 28 34  1  0
 26 55  1  0
 26 56  1  0
 26 57  1  0
 25 54  1  0
 27 58  1  0
 27 59  1  0
 27 60  1  0
 24 52  1  0
 24 53  1  0
 20 51  1  6
 18 50  1  0
 16 48  1  0
 16 49  1  0
 14 47  1  6
 10 43  1  1
 11 44  1  0
 11 45  1  0
 12 46  1  0
  8 41  1  6
  9 42  1  0
  6 39  1  1
  7 40  1  0
  5 38  1  6
  1 35  1  0
  1 36  1  0
  1 37  1  0
 34 70  1  1
 33 68  1  0
 33 69  1  0
 32 66  1  0
 32 67  1  0
 29 62  1  6
 30 63  1  0
 30 64  1  0
 31 65  1  0
 28 61  1  1
M  END


  Mrv1652309062203002D          

 34 36  0  0  1  0            999 V2000
    2.1434    8.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    7.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    7.4250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    7.4250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    6.6000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1434    6.1875    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8579    6.6000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    5.3625    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8579    4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    4.9500    0.0000 C   0  0  1  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
    0.7145    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    5.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    6.1875    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0000    6.6000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    3.7125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7145    2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.8875    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
    2.1434    2.8875    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
   -1.4289    4.1250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.2136    3.8701    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.4685    3.0854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2755    2.9139    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6985    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2136    5.2049    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    4.9500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  5  4  1  6  0  0  0
  5  6  1  0  0  0  0
  6  7  1  1  0  0  0
  6  8  1  0  0  0  0
  8  9  1  6  0  0  0
  8 10  1  0  0  0  0
 10 11  1  1  0  0  0
 11 12  1  0  0  0  0
 10 13  1  0  0  0  0
 13 14  1  0  0  0  0
  5 14  1  0  0  0  0
 14 15  1  1  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  1  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  1  0  0  0  0
 20 28  1  0  0  0  0
 28 29  1  6  0  0  0
 29 30  1  1  0  0  0
 30 31  1  0  0  0  0
 29 32  1  0  0  0  0
 32 33  1  0  0  0  0
 34 33  1  6  0  0  0
 17 34  1  0  0  0  0
 28 34  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0223023

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)CC(=O)O[C@@H]1OC=C(CO[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2OC(C)=O)[C@H]2CC[C@H](CO)[C@@H]12

> <INCHI_IDENTIFIER>
InChI=1S/C23H36O11/c1-11(2)6-17(27)34-22-18-13(7-24)4-5-15(18)14(9-30-22)10-31-23-21(32-12(3)26)20(29)19(28)16(8-25)33-23/h9,11,13,15-16,18-25,28-29H,4-8,10H2,1-3H3/t13-,15-,16-,18-,19-,20+,21-,22+,23-/m1/s1

> <INCHI_KEY>
SCXWDHJIINFXNY-VSHZGDBNSA-N

> <FORMULA>
C23H36O11

> <MOLECULAR_WEIGHT>
488.53

> <EXACT_MASS>
488.225761979

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
70

> <JCHEM_AVERAGE_POLARIZABILITY>
49.78307936321594

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,4aS,7S,7aS)-4-({[(2R,3R,4S,5S,6R)-3-(acetyloxy)-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)-7-(hydroxymethyl)-1H,4aH,5H,6H,7H,7aH-cyclopenta[c]pyran-1-yl 3-methylbutanoate

> <JCHEM_LOGP>
-0.4244222699999999

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.002647402223367

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.694903764109611

> <JCHEM_PKA_STRONGEST_BASIC>
-2.6007264027621195

> <JCHEM_POLAR_SURFACE_AREA>
161.21

> <JCHEM_REFRACTIVITY>
115.1015

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1S,4aS,7S,7aS)-4-({[(2R,3R,4S,5S,6R)-3-(acetyloxy)-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)-7-(hydroxymethyl)-1H,4aH,5H,6H,7H,7aH-cyclopenta[c]pyran-1-yl 3-methylbutanoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-SEP-22         0                                  
HETATM    1  C   UNK     0       4.001  16.170   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.001  14.630   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       5.335  13.860   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       2.667  13.860   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       2.667  12.320   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.001  11.550   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       5.335  12.320   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       4.001  10.010   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       5.335   9.240   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       2.667   9.240   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.667   7.700   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       1.334   6.930   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0       1.334  10.010   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       1.334  11.550   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -0.000  12.320   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      -1.334  11.550   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -1.334  10.010   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.000   9.240   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       0.000   7.700   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      -1.334   6.930   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      -1.334   5.390   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       0.000   3.080   0.000  0.00  0.00           O+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       4.001   5.390   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       2.667   3.080   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -2.667   7.700   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -4.132   7.224   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -4.608   5.759   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      -6.114   5.439   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      -5.037   8.470   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -4.132   9.716   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      -2.667   9.240   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6   14                                                  
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   13                                                  
CONECT   11   10   12                                                       
CONECT   12   11                                                            
CONECT   13   10   14                                                       
CONECT   14   13    5   15                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   34                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21   28                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25                                                       
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25                                                            
CONECT   28   20   29   34                                                  
CONECT   29   28   30   32                                                  
CONECT   30   29   31                                                       
CONECT   31   30                                                            
CONECT   32   29   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33   17   28                                                  
MASTER        0    0    0    0    0    0    0    0   34    0   72    0
END

View in JSmol

Synonyms

Value	Source
[[(1S)-1,4Aalpha,5,6,7,7aalpha-hexahydro-7a-(hydroxymethyl)-1a-(isovaleryloxy)cyclopenta[c]pyran]-4-yl]methyl 2-O-acetyl-b-D-glucopyranoside	Generator
[[(1S)-1,4Aalpha,5,6,7,7aalpha-hexahydro-7α-(hydroxymethyl)-1α-(isovaleryloxy)cyclopenta[c]pyran]-4-yl]methyl 2-O-acetyl-β-D-glucopyranoside	Generator

Chemical Formula

C₂₃H₃₆O₁₁

Average Mass

488.5300 Da

Monoisotopic Mass

488.22576 Da

IUPAC Name

(1S,4aS,7S,7aS)-4-({[(2R,3R,4S,5S,6R)-3-(acetyloxy)-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)-7-(hydroxymethyl)-1H,4aH,5H,6H,7H,7aH-cyclopenta[c]pyran-1-yl 3-methylbutanoate

Traditional Name

(1S,4aS,7S,7aS)-4-({[(2R,3R,4S,5S,6R)-3-(acetyloxy)-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)-7-(hydroxymethyl)-1H,4aH,5H,6H,7H,7aH-cyclopenta[c]pyran-1-yl 3-methylbutanoate

CAS Registry Number

Not Available

SMILES

CC(C)CC(=O)O[C@@H]1OC=C(CO[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2OC(C)=O)[C@H]2CC[C@H](CO)[C@@H]12

InChI Identifier

InChI=1S/C23H36O11/c1-11(2)6-17(27)34-22-18-13(7-24)4-5-15(18)14(9-30-22)10-31-23-21(32-12(3)26)20(29)19(28)16(8-25)33-23/h9,11,13,15-16,18-25,28-29H,4-8,10H2,1-3H3/t13-,15-,16-,18-,19-,20+,21-,22+,23-/m1/s1

InChI Key

SCXWDHJIINFXNY-VSHZGDBNSA-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
Viburnum lantana L.	LOTUS Database	35616633
Viburnum prunifolium	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
Hexose monosaccharide
Glycosyl compound
Iridoid-skeleton
O-glycosyl compound
Bicyclic monoterpenoid
Monoterpenoid
Fatty acid ester
Oxane
Fatty acyl
Monosaccharide
Dicarboxylic acid or derivatives
Secondary alcohol
Carboxylic acid ester
Organoheterocyclic compound
Oxacycle
Acetal
Carboxylic acid derivative
Primary alcohol
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Carbonyl group
Alcohol
Organooxygen compound
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	-0.42	ChemAxon
pKa (Strongest Acidic)	12.69	ChemAxon
pKa (Strongest Basic)	-2.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	161.21 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	115.1 m³·mol⁻¹	ChemAxon
Polarizability	49.78 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	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

14109593

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1s,4as,7s,7as)-4-({[(2r,3r,4s,5s,6r)-3-(acetyloxy)-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)-7-(hydroxymethyl)-1h,4ah,5h,6h,7h,7ah-cyclopenta[c]pyran-1-yl 3-methylbutanoate (NP0223023)

MOL for NP0223023 ((1s,4as,7s,7as)-4-({[(2r,3r,4s,5s,6r)-3-(acetyloxy)-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)-7-(hydroxymethyl)-1h,4ah,5h,6h,7h,7ah-cyclopenta[c]pyran-1-yl 3-methylbutanoate)

3D MOL for NP0223023 ((1s,4as,7s,7as)-4-({[(2r,3r,4s,5s,6r)-3-(acetyloxy)-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)-7-(hydroxymethyl)-1h,4ah,5h,6h,7h,7ah-cyclopenta[c]pyran-1-yl 3-methylbutanoate)

3D SDF for NP0223023 ((1s,4as,7s,7as)-4-({[(2r,3r,4s,5s,6r)-3-(acetyloxy)-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)-7-(hydroxymethyl)-1h,4ah,5h,6h,7h,7ah-cyclopenta[c]pyran-1-yl 3-methylbutanoate)

3D-SDF for NP0223023 ((1s,4as,7s,7as)-4-({[(2r,3r,4s,5s,6r)-3-(acetyloxy)-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)-7-(hydroxymethyl)-1h,4ah,5h,6h,7h,7ah-cyclopenta[c]pyran-1-yl 3-methylbutanoate)

PDB for NP0223023 ((1s,4as,7s,7as)-4-({[(2r,3r,4s,5s,6r)-3-(acetyloxy)-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)-7-(hydroxymethyl)-1h,4ah,5h,6h,7h,7ah-cyclopenta[c]pyran-1-yl 3-methylbutanoate)

3D PDB for NP0223023 ((1s,4as,7s,7as)-4-({[(2r,3r,4s,5s,6r)-3-(acetyloxy)-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)-7-(hydroxymethyl)-1h,4ah,5h,6h,7h,7ah-cyclopenta[c]pyran-1-yl 3-methylbutanoate)

SMILES for NP0223023 ((1s,4as,7s,7as)-4-({[(2r,3r,4s,5s,6r)-3-(acetyloxy)-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)-7-(hydroxymethyl)-1h,4ah,5h,6h,7h,7ah-cyclopenta[c]pyran-1-yl 3-methylbutanoate)

INCHI for NP0223023 ((1s,4as,7s,7as)-4-({[(2r,3r,4s,5s,6r)-3-(acetyloxy)-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)-7-(hydroxymethyl)-1h,4ah,5h,6h,7h,7ah-cyclopenta[c]pyran-1-yl 3-methylbutanoate)

Structure for NP0223023 ((1s,4as,7s,7as)-4-({[(2r,3r,4s,5s,6r)-3-(acetyloxy)-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)-7-(hydroxymethyl)-1h,4ah,5h,6h,7h,7ah-cyclopenta[c]pyran-1-yl 3-methylbutanoate)

3D Structure for NP0223023 ((1s,4as,7s,7as)-4-({[(2r,3r,4s,5s,6r)-3-(acetyloxy)-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)-7-(hydroxymethyl)-1h,4ah,5h,6h,7h,7ah-cyclopenta[c]pyran-1-yl 3-methylbutanoate)