NP-MRD: Showing NP-Card for (2s,3r,4s,5r,6r)-2-{[(1ar,4r,4as,7r,7as,7bs)-1,1,4,7-tetramethyl-octahydro-1ah-cyclopropa[e]azulen-4-yl]oxy}-4,5-dihydroxy-6-methyloxan-3-yl 2-methylbutanoate (NP0255712)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-07 20:17:39 UTC

Updated at

2022-09-07 20:17:39 UTC

NP-MRD ID

NP0255712

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2s,3r,4s,5r,6r)-2-{[(1ar,4r,4as,7r,7as,7bs)-1,1,4,7-tetramethyl-octahydro-1ah-cyclopropa[e]azulen-4-yl]oxy}-4,5-dihydroxy-6-methyloxan-3-yl 2-methylbutanoate

Description

CHEMBL464464 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. (2s,3r,4s,5r,6r)-2-{[(1ar,4r,4as,7r,7as,7bs)-1,1,4,7-tetramethyl-octahydro-1ah-cyclopropa[e]azulen-4-yl]oxy}-4,5-dihydroxy-6-methyloxan-3-yl 2-methylbutanoate is found in Calendula arvensis. Based on a literature review very few articles have been published on CHEMBL464464.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309072222172D          

 32 35  0  0  1  0            999 V2000
    3.4857    6.3147    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8260    5.8194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9251    5.0003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6839    4.6767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2653    4.5050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5065    4.8287    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3644    3.6860    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7047    3.1906    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8038    2.3716    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5627    2.0479    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6618    1.2289    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8413    1.3145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4382    1.5078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1404    1.0746    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2395    0.2556    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.6609   -0.3326    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8404   -0.2469    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3957    0.4480    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5974    0.2398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5487   -0.5837    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3169   -0.8846    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5251   -1.6829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4596   -0.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6095   -1.3508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2732   -0.6761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1441    1.8762    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3852    2.1999    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2745    1.7046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2861    3.0189    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4727    3.3426    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9459    3.5143    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8467    4.3333    0.0000 O   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  1  0  0  0  0
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  8  7  1  1  0  0  0
  8  9  1  0  0  0  0
  9 10  1  6  0  0  0
 11 10  1  6  0  0  0
 11 12  1  1  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 15 14  1  1  0  0  0
 16 15  1  1  0  0  0
 17 16  1  6  0  0  0
 17 18  1  0  0  0  0
 11 18  1  0  0  0  0
 18 19  1  6  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 17 21  1  0  0  0  0
 21 22  1  6  0  0  0
 16 23  1  0  0  0  0
 15 23  1  0  0  0  0
 23 24  1  0  0  0  0
 23 25  1  0  0  0  0
  9 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  6  0  0  0
 27 29  1  0  0  0  0
 29 30  1  6  0  0  0
 29 31  1  0  0  0  0
  8 31  1  0  0  0  0
 31 32  1  6  0  0  0
M  END

     RDKit          3D

 76 79  0  0  0  0  0  0  0  0999 V2000
   -1.7125    0.2689    2.9934 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3515    1.6578    2.9032 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4663    1.5870    1.9195 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.0970    2.9840    1.8555 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1201    1.1107    0.5782 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3808    1.8281   -0.4606 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5097   -0.0979    0.2533 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2235   -0.5138   -1.0330 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8533   -0.7818   -1.4796 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2032   -0.0713   -1.0761 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3882   -0.7224   -0.8828 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7936   -1.4087   -2.2516 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5155   -1.8144    0.0763 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2021   -1.6432    1.4838 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6526   -0.5359    2.2909 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2966    0.6288    1.8509 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7207    0.9638    0.5183 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5185    0.2250   -0.6863 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4279    1.2049   -1.8709 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6456    2.5649   -1.2948 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2177    2.3766    0.1251 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7618    2.5407    0.3674 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1316   -0.3796    2.6536 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5056   -0.0257    4.0837 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0937   -1.3010    2.0087 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9552   -0.6746   -2.9302 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5720   -1.7592   -3.4703 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1333   -1.3109   -4.8270 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6002   -2.4097   -2.6287 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.6546   -2.7888   -3.4978 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1773   -1.6211   -1.5112 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.4041   -1.1032   -1.9075 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1698    0.1313    3.9260 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5752   -0.4449    2.8872 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1097    0.1762    2.0743 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7242    1.8644    3.9270 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6091    2.4286    2.6731 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2748    0.9233    2.3095 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0216    3.0441    2.4500 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3818    3.1732    0.7959 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3406    3.7480    2.1251 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5847    0.3635   -1.6853 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6191   -1.8890   -1.4200 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2197   -2.3510   -2.3579 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8584   -1.7147   -2.1908 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6992   -0.6955   -3.0633 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8586   -2.6675   -0.3043 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5490   -2.2826   -0.1058 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5817   -2.5917    2.0043 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0810   -1.8009    1.5941 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0435   -0.4625    3.2537 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1414    1.5656    2.4887 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8425    1.1781    0.6085 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4500   -0.3760   -0.9467 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4041    1.2049   -2.3163 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1142    0.9731   -2.6810 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6646    2.9469   -1.3814 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9500    3.3250   -1.7500 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7582    3.1491    0.7410 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2584    2.6522   -0.6337 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2916    1.7665    0.9689 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5348    3.5175    0.8889 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4207    0.6190    4.0094 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6718    0.4783    4.5869 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8235   -0.9555    4.5802 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0043   -1.4734    2.6638 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6226   -2.3295    2.0182 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5145   -1.0086    1.0536 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7463   -2.4871   -3.7462 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9878   -2.1136   -5.5908 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1964   -1.0815   -4.7906 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5981   -0.4213   -5.2127 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1860   -3.4047   -2.2933 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5058   -2.8498   -2.9743 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3594   -2.2784   -0.6389 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2315   -0.5272   -2.6989 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  3  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  0
  8 31  1  0
 31 32  1  0
 31 29  1  0
 29 30  1  0
 29 27  1  0
 27 28  1  0
 27 26  1  0
 26  9  1  0
  9 10  1  0
 11 10  1  6
 11 12  1  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 21  1  0
 21 22  1  0
 21 20  1  0
 20 19  1  0
 19 18  1  0
 16 23  1  0
 23 24  1  0
 23 25  1  0
  9  8  1  0
 18 11  1  0
 23 15  1  0
 18 17  1  0
  1 33  1  0
  1 34  1  0
  1 35  1  0
  2 36  1  0
  2 37  1  0
  3 38  1  1
  4 39  1  0
  4 40  1  0
  4 41  1  0
  8 42  1  6
 31 75  1  1
 32 76  1  0
 29 73  1  1
 30 74  1  0
 27 69  1  6
 28 70  1  0
 28 71  1  0
 28 72  1  0
  9 43  1  6
 12 44  1  0
 12 45  1  0
 12 46  1  0
 13 47  1  0
 13 48  1  0
 14 49  1  0
 14 50  1  0
 15 51  1  1
 16 52  1  1
 17 53  1  1
 21 59  1  1
 22 60  1  0
 22 61  1  0
 22 62  1  0
 20 57  1  0
 20 58  1  0
 19 55  1  0
 19 56  1  0
 18 54  1  6
 24 63  1  0
 24 64  1  0
 24 65  1  0
 25 66  1  0
 25 67  1  0
 25 68  1  0
M  END


  Mrv1652309072222172D          

 32 35  0  0  1  0            999 V2000
    3.4857    6.3147    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8260    5.8194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9251    5.0003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6839    4.6767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2653    4.5050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5065    4.8287    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3644    3.6860    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7047    3.1906    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8038    2.3716    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5627    2.0479    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6618    1.2289    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8413    1.3145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4382    1.5078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1404    1.0746    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2395    0.2556    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.6609   -0.3326    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8404   -0.2469    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3957    0.4480    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5974    0.2398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5487   -0.5837    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3169   -0.8846    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5251   -1.6829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4596   -0.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6095   -1.3508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2732   -0.6761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1441    1.8762    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3852    2.1999    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2745    1.7046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2861    3.0189    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4727    3.3426    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9459    3.5143    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8467    4.3333    0.0000 O   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  1  0  0  0  0
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  8  7  1  1  0  0  0
  8  9  1  0  0  0  0
  9 10  1  6  0  0  0
 11 10  1  6  0  0  0
 11 12  1  1  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 15 14  1  1  0  0  0
 16 15  1  1  0  0  0
 17 16  1  6  0  0  0
 17 18  1  0  0  0  0
 11 18  1  0  0  0  0
 18 19  1  6  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 17 21  1  0  0  0  0
 21 22  1  6  0  0  0
 16 23  1  0  0  0  0
 15 23  1  0  0  0  0
 23 24  1  0  0  0  0
 23 25  1  0  0  0  0
  9 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  6  0  0  0
 27 29  1  0  0  0  0
 29 30  1  6  0  0  0
 29 31  1  0  0  0  0
  8 31  1  0  0  0  0
 31 32  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0255712

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCC(C)C(=O)O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](C)O[C@H]1O[C@]1(C)CC[C@@H]2[C@H]([C@@H]3[C@H](C)CC[C@H]13)C2(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C26H44O6/c1-8-13(2)23(29)31-22-21(28)20(27)15(4)30-24(22)32-26(7)12-11-17-19(25(17,5)6)18-14(3)9-10-16(18)26/h13-22,24,27-28H,8-12H2,1-7H3/t13?,14-,15-,16+,17-,18-,19-,20+,21+,22-,24+,26-/m1/s1

> <INCHI_KEY>
WSKBKHXYHUTYKP-MZBXDKBKSA-N

> <FORMULA>
C26H44O6

> <MOLECULAR_WEIGHT>
452.632

> <EXACT_MASS>
452.313789137

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
76

> <JCHEM_AVERAGE_POLARIZABILITY>
51.6149983970673

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S,3R,4S,5R,6R)-2-{[(1aR,4R,4aS,7R,7aS,7bS)-1,1,4,7-tetramethyl-decahydro-1H-cyclopropa[e]azulen-4-yl]oxy}-4,5-dihydroxy-6-methyloxan-3-yl 2-methylbutanoate

> <JCHEM_LOGP>
4.583792940666667

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.182133955396061

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.738855425434824

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6129051241977876

> <JCHEM_POLAR_SURFACE_AREA>
85.22000000000001

> <JCHEM_REFRACTIVITY>
120.4235

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(2S,3R,4S,5R,6R)-2-{[(1aR,4R,4aS,7R,7aS,7bS)-1,1,4,7-tetramethyl-octahydro-1aH-cyclopropa[e]azulen-4-yl]oxy}-4,5-dihydroxy-6-methyloxan-3-yl 2-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       6.507  11.787   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.275  10.863   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.460   9.334   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.877   8.730   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.229   8.409   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       2.812   9.014   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0       4.414   6.880   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       3.182   5.956   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.367   4.427   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       4.784   3.823   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       4.969   2.294   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.437   2.454   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.418   2.815   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.729   2.006   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.914   0.477   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.834  -0.621   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.302  -0.461   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.472   0.836   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.982   0.448   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.891  -1.090   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.325  -1.651   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.713  -3.141   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       8.325  -1.007   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       8.604  -2.521   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       9.843  -1.262   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       2.136   3.502   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       0.719   4.107   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -0.512   3.182   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       0.534   5.635   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      -0.882   6.240   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       1.766   6.560   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       1.581   8.089   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9   31                                                  
CONECT    9    8   10   26                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   13   18                                             
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   23                                                  
CONECT   16   15   17   23                                                  
CONECT   17   16   18   21                                                  
CONECT   18   17   11   19                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   17   22                                                  
CONECT   22   21                                                            
CONECT   23   16   15   24   25                                             
CONECT   24   23                                                            
CONECT   25   23                                                            
CONECT   26    9   27                                                       
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29    8   32                                                  
CONECT   32   31                                                            
MASTER        0    0    0    0    0    0    0    0   32    0   70    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₆H₄₄O₆

Average Mass

452.6320 Da

Monoisotopic Mass

452.31379 Da

IUPAC Name

(2S,3R,4S,5R,6R)-2-{[(1aR,4R,4aS,7R,7aS,7bS)-1,1,4,7-tetramethyl-decahydro-1H-cyclopropa[e]azulen-4-yl]oxy}-4,5-dihydroxy-6-methyloxan-3-yl 2-methylbutanoate

Traditional Name

(2S,3R,4S,5R,6R)-2-{[(1aR,4R,4aS,7R,7aS,7bS)-1,1,4,7-tetramethyl-octahydro-1aH-cyclopropa[e]azulen-4-yl]oxy}-4,5-dihydroxy-6-methyloxan-3-yl 2-methylbutanoate

CAS Registry Number

Not Available

SMILES

CCC(C)C(=O)O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](C)O[C@H]1O[C@]1(C)CC[C@@H]2[C@H]([C@@H]3[C@H](C)CC[C@H]13)C2(C)C

InChI Identifier

InChI=1S/C26H44O6/c1-8-13(2)23(29)31-22-21(28)20(27)15(4)30-24(22)32-26(7)12-11-17-19(25(17,5)6)18-14(3)9-10-16(18)26/h13-22,24,27-28H,8-12H2,1-7H3/t13?,14-,15-,16+,17-,18-,19-,20+,21+,22-,24+,26-/m1/s1

InChI Key

WSKBKHXYHUTYKP-MZBXDKBKSA-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
Calendula arvensis	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
Aromadendrane sesquiterpenoid
Guaiane sesquiterpenoid
5,10-cycloaromadendrane sesquiterpenoid
Sesquiterpenoid
Hexose monosaccharide
Glycosyl compound
O-glycosyl compound
Fatty acid ester
Fatty acyl
Monosaccharide
Oxane
1,2-diol
Carboxylic acid ester
Secondary alcohol
Organoheterocyclic compound
Acetal
Monocarboxylic acid or derivatives
Oxacycle
Carboxylic acid derivative
Hydrocarbon derivative
Organic oxide
Carbonyl group
Organic oxygen compound
Organooxygen compound
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	4.58	ChemAxon
pKa (Strongest Acidic)	12.74	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	85.22 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	120.42 m³·mol⁻¹	ChemAxon
Polarizability	51.61 Å³	ChemAxon
Number of Rings	4	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

23339935

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

44567060

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2s,3r,4s,5r,6r)-2-{[(1ar,4r,4as,7r,7as,7bs)-1,1,4,7-tetramethyl-octahydro-1ah-cyclopropa[e]azulen-4-yl]oxy}-4,5-dihydroxy-6-methyloxan-3-yl 2-methylbutanoate (NP0255712)

MOL for NP0255712 ((2s,3r,4s,5r,6r)-2-{[(1ar,4r,4as,7r,7as,7bs)-1,1,4,7-tetramethyl-octahydro-1ah-cyclopropa[e]azulen-4-yl]oxy}-4,5-dihydroxy-6-methyloxan-3-yl 2-methylbutanoate)

3D MOL for NP0255712 ((2s,3r,4s,5r,6r)-2-{[(1ar,4r,4as,7r,7as,7bs)-1,1,4,7-tetramethyl-octahydro-1ah-cyclopropa[e]azulen-4-yl]oxy}-4,5-dihydroxy-6-methyloxan-3-yl 2-methylbutanoate)

3D SDF for NP0255712 ((2s,3r,4s,5r,6r)-2-{[(1ar,4r,4as,7r,7as,7bs)-1,1,4,7-tetramethyl-octahydro-1ah-cyclopropa[e]azulen-4-yl]oxy}-4,5-dihydroxy-6-methyloxan-3-yl 2-methylbutanoate)

3D-SDF for NP0255712 ((2s,3r,4s,5r,6r)-2-{[(1ar,4r,4as,7r,7as,7bs)-1,1,4,7-tetramethyl-octahydro-1ah-cyclopropa[e]azulen-4-yl]oxy}-4,5-dihydroxy-6-methyloxan-3-yl 2-methylbutanoate)

PDB for NP0255712 ((2s,3r,4s,5r,6r)-2-{[(1ar,4r,4as,7r,7as,7bs)-1,1,4,7-tetramethyl-octahydro-1ah-cyclopropa[e]azulen-4-yl]oxy}-4,5-dihydroxy-6-methyloxan-3-yl 2-methylbutanoate)

3D PDB for NP0255712 ((2s,3r,4s,5r,6r)-2-{[(1ar,4r,4as,7r,7as,7bs)-1,1,4,7-tetramethyl-octahydro-1ah-cyclopropa[e]azulen-4-yl]oxy}-4,5-dihydroxy-6-methyloxan-3-yl 2-methylbutanoate)

SMILES for NP0255712 ((2s,3r,4s,5r,6r)-2-{[(1ar,4r,4as,7r,7as,7bs)-1,1,4,7-tetramethyl-octahydro-1ah-cyclopropa[e]azulen-4-yl]oxy}-4,5-dihydroxy-6-methyloxan-3-yl 2-methylbutanoate)

INCHI for NP0255712 ((2s,3r,4s,5r,6r)-2-{[(1ar,4r,4as,7r,7as,7bs)-1,1,4,7-tetramethyl-octahydro-1ah-cyclopropa[e]azulen-4-yl]oxy}-4,5-dihydroxy-6-methyloxan-3-yl 2-methylbutanoate)

Structure for NP0255712 ((2s,3r,4s,5r,6r)-2-{[(1ar,4r,4as,7r,7as,7bs)-1,1,4,7-tetramethyl-octahydro-1ah-cyclopropa[e]azulen-4-yl]oxy}-4,5-dihydroxy-6-methyloxan-3-yl 2-methylbutanoate)

3D Structure for NP0255712 ((2s,3r,4s,5r,6r)-2-{[(1ar,4r,4as,7r,7as,7bs)-1,1,4,7-tetramethyl-octahydro-1ah-cyclopropa[e]azulen-4-yl]oxy}-4,5-dihydroxy-6-methyloxan-3-yl 2-methylbutanoate)