NP-MRD: Showing NP-Card for (1s,4as,6r,7s,7as)-6,7-dihydroxy-7-methyl-4-[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)-2-methoxyoxan-2-yl]-1h,4ah,5h,6h,7ah-cyclopenta[c]pyran-1-yl 3-methylbutanoate (NP0241872)

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Record Information

Version

2.0

Created at

2022-09-07 02:03:28 UTC

Updated at

2022-09-07 02:03:28 UTC

NP-MRD ID

NP0241872

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,4as,6r,7s,7as)-6,7-dihydroxy-7-methyl-4-[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)-2-methoxyoxan-2-yl]-1h,4ah,5h,6h,7ah-cyclopenta[c]pyran-1-yl 3-methylbutanoate

Description

88586-75-8 Belongs to the class of organic compounds known as iridoids and derivatives. These are monoterpenes containing a skeleton structurally characterized by the presence of a cylopentane fused to a pyran ( forming a 4,7-dimethylcyclopenta[c]pyran), or a derivative where the pentane moiety is open. (1s,4as,6r,7s,7as)-6,7-dihydroxy-7-methyl-4-[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)-2-methoxyoxan-2-yl]-1h,4ah,5h,6h,7ah-cyclopenta[c]pyran-1-yl 3-methylbutanoate is found in Penstemon richardsonii and Penstemon serrulatus. Based on a literature review very few articles have been published on 88586-75-8.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309072204032D          

 32 34  0  0  1  0            999 V2000
   -2.0572    6.6762    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5269    6.0442    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    6.1875    0.0000 C   0  0  2  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  1  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
   -2.2136    5.2049    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6985    4.5375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.5235    4.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2136    3.8701    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8208    3.3116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0505    3.0613    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9966    6.9627    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4663    7.5947    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7485    8.3700    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5610    8.5132    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3461    7.4515    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8764    8.0835    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6283    6.6762    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4408    6.5330    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0980    6.0442    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3802    5.2690    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  3  2  1  6  0  0  0
  3  4  1  1  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  1  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
  7 15  1  0  0  0  0
 15 16  1  6  0  0  0
  4 16  1  0  0  0  0
 16 17  1  6  0  0  0
 17 18  1  0  0  0  0
 18 19  1  6  0  0  0
 18 20  1  0  0  0  0
 15 20  1  0  0  0  0
 20 21  1  1  0  0  0
 20 22  1  6  0  0  0
  3 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  6  0  0  0
 25 26  1  0  0  0  0
 24 27  1  0  0  0  0
 27 28  1  1  0  0  0
 27 29  1  0  0  0  0
 29 30  1  6  0  0  0
 29 31  1  0  0  0  0
  3 31  1  0  0  0  0
 31 32  1  1  0  0  0
M  END

     RDKit          3D

 66 68  0  0  0  0  0  0  0  0999 V2000
   -1.2335    1.8723    1.3540 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2256    0.8985    1.5708 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4000    0.1995    0.3489 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1032   -0.3900   -0.0613 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5810   -0.0432   -1.2246 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6278   -0.5288   -1.7116 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6389   -0.6872   -0.7288 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2908    0.5345   -0.4328 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5891    0.8351   -0.7168 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2648   -0.0707   -1.2998 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2340    2.1379   -0.3853 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6588    2.2059   -0.8126 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8215    2.0274   -2.2966 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5554    1.2733   -0.0254 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1204   -1.4017    0.4741 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3187   -1.3578    0.7412 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7376   -2.7582    0.6905 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2350   -3.4788   -0.1827 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0324   -3.0827   -1.5017 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5271   -2.8819    0.3670 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8997   -3.4770    1.6788 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5171   -3.1059   -0.5490 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7912    1.1389   -0.5848 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0922    1.4692   -0.6229 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.3714    2.8509   -1.1775 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7389    3.1117   -1.1816 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8248    1.3569    0.6889 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.1535    1.7197    0.4885 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7576   -0.0974    1.0641 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.9155   -0.1886    2.4662 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4933   -0.7806    0.5935 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.7954   -1.4447   -0.5679 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2711    1.4188    1.0478 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0641    2.4175    2.3120 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5667    2.6076    0.6085 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1410    0.6736   -1.8420 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4126   -1.3086   -1.2237 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1941    2.3307    0.7196 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6680    2.9505   -0.8520 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0141    3.2423   -0.5662 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9148    2.4792   -2.7831 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9312    0.9580   -2.5704 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6911    2.6333   -2.6195 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5052    0.2300   -0.4006 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2612    1.3446    1.0375 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5939    1.6703   -0.0918 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6803   -1.0101    1.3455 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4965   -0.9981    1.8100 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7605   -2.9973    0.4106 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6120   -3.2099    1.7220 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1985   -4.5757   -0.0630 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1172   -3.8294   -2.1457 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0233   -3.5060    1.7263 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5676   -2.8761    2.5279 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5391   -4.5258    1.7070 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2670   -3.6598   -0.1985 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6142    0.7505   -1.3228 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7991    3.6267   -0.6173 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0385    2.9449   -2.2383 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9328    4.0596   -1.3168 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4258    2.0283    1.4678 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5860    1.8189    1.3805 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6652   -0.5812    0.6470 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8935   -1.1552    2.6767 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1916   -1.4230    1.4447 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0001   -2.3858   -0.4340 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  3  2  1  1
  3 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 24 27  1  0
 27 28  1  0
 27 29  1  0
 29 30  1  0
 29 31  1  0
 31 32  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  1  0
  7 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
 20 22  1  6
 31  3  1  0
 16  4  1  0
 20 15  1  0
  1 33  1  0
  1 34  1  0
  1 35  1  0
 24 57  1  6
 25 58  1  0
 25 59  1  0
 26 60  1  0
 27 61  1  1
 28 62  1  0
 29 63  1  6
 30 64  1  0
 31 65  1  1
 32 66  1  0
  5 36  1  0
  7 37  1  6
 11 38  1  0
 11 39  1  0
 12 40  1  0
 13 41  1  0
 13 42  1  0
 13 43  1  0
 14 44  1  0
 14 45  1  0
 14 46  1  0
 15 47  1  1
 16 48  1  1
 17 49  1  0
 17 50  1  0
 18 51  1  6
 19 52  1  0
 21 53  1  0
 21 54  1  0
 21 55  1  0
 22 56  1  0
M  END


  Mrv1652309072204032D          

 32 34  0  0  1  0            999 V2000
   -2.0572    6.6762    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5269    6.0442    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    6.1875    0.0000 C   0  0  2  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  1  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
   -2.2136    5.2049    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6985    4.5375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.5235    4.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2136    3.8701    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8208    3.3116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0505    3.0613    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9966    6.9627    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4663    7.5947    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7485    8.3700    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5610    8.5132    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3461    7.4515    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8764    8.0835    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6283    6.6762    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4408    6.5330    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0980    6.0442    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3802    5.2690    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  3  2  1  6  0  0  0
  3  4  1  1  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  1  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
  7 15  1  0  0  0  0
 15 16  1  6  0  0  0
  4 16  1  0  0  0  0
 16 17  1  6  0  0  0
 17 18  1  0  0  0  0
 18 19  1  6  0  0  0
 18 20  1  0  0  0  0
 15 20  1  0  0  0  0
 20 21  1  1  0  0  0
 20 22  1  6  0  0  0
  3 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  6  0  0  0
 25 26  1  0  0  0  0
 24 27  1  0  0  0  0
 27 28  1  1  0  0  0
 27 29  1  0  0  0  0
 29 30  1  6  0  0  0
 29 31  1  0  0  0  0
  3 31  1  0  0  0  0
 31 32  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0241872

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C21H34O11/c1-9(2)5-14(24)31-19-15-10(6-13(23)20(15,3)28)11(8-30-19)21(29-4)18(27)17(26)16(25)12(7-22)32-21/h8-10,12-13,15-19,22-23,25-28H,5-7H2,1-4H3/t10-,12-,13-,15-,16-,17+,18-,19+,20-,21-/m1/s1

> <INCHI_KEY>
CBSFNBFNBQFAQG-ALWYBGAQSA-N

> <FORMULA>
C21H34O11

> <MOLECULAR_WEIGHT>
462.492

> <EXACT_MASS>
462.210111915

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
66

> <JCHEM_AVERAGE_POLARIZABILITY>
45.878183792319284

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <JCHEM_LOGP>
-1.4795012346666683

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.000953175495027

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.037334195826421

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9815768880847093

> <JCHEM_POLAR_SURFACE_AREA>
175.37

> <JCHEM_REFRACTIVITY>
106.96570000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(1S,4aS,6R,7S,7aS)-6,7-dihydroxy-7-methyl-4-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)-2-methoxyoxan-2-yl]-1H,4aH,5H,6H,7aH-cyclopenta[c]pyran-1-yl 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      -3.840  12.462   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -2.850  11.283   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -1.334  11.550   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.334  10.010   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000   9.240   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       0.000   7.700   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      -1.334   6.930   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -1.334   5.390   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       0.000   3.080   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       1.334   5.390   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.001   5.390   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.667   3.080   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -2.667   7.700   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -2.667   9.240   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -4.132   9.716   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -5.037   8.470   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -6.577   8.470   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      -4.132   7.224   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -5.266   6.182   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      -3.828   5.714   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      -1.860  12.997   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      -0.870  14.177   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -1.397  15.624   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      -2.914  15.891   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       0.646  13.909   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       1.636  15.089   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       1.173  12.462   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       2.689  12.195   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       0.183  11.283   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       0.710   9.835   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   23   31                                             
CONECT    4    3    5   16                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8   15                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12                                                            
CONECT   15    7   16   20                                                  
CONECT   16   15    4   17                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   15   21   22                                             
CONECT   21   20                                                            
CONECT   22   20                                                            
CONECT   23    3   24                                                       
CONECT   24   23   25   27                                                  
CONECT   25   24   26                                                       
CONECT   26   25                                                            
CONECT   27   24   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29    3   32                                                  
CONECT   32   31                                                            
MASTER        0    0    0    0    0    0    0    0   32    0   68    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₁H₃₄O₁₁

Average Mass

462.4920 Da

Monoisotopic Mass

462.21011 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

CO[C@@]1(O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O)C1=CO[C@@H](OC(=O)CC(C)C)[C@H]2[C@@H]1C[C@@H](O)[C@@]2(C)O

InChI Identifier

InChI=1S/C21H34O11/c1-9(2)5-14(24)31-19-15-10(6-13(23)20(15,3)28)11(8-30-19)21(29-4)18(27)17(26)16(25)12(7-22)32-21/h8-10,12-13,15-19,22-23,25-28H,5-7H2,1-4H3/t10-,12-,13-,15-,16-,17+,18-,19+,20-,21-/m1/s1

InChI Key

CBSFNBFNBQFAQG-ALWYBGAQSA-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
Penstemon richardsonii	LOTUS Database	35616633
Penstemon serrulatus	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as iridoids and derivatives. These are monoterpenes containing a skeleton structurally characterized by the presence of a cylopentane fused to a pyran ( forming a 4,7-dimethylcyclopenta[c]pyran), or a derivative where the pentane moiety is open.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Monoterpenoids

Direct Parent

Iridoids and derivatives

Alternative Parents

Substituents

Iridoid-skeleton
Glycosyl compound
C-glycosyl compound
Bicyclic monoterpenoid
Ketal
Fatty acid ester
Fatty acyl
Oxane
Monosaccharide
Tertiary alcohol
Cyclic alcohol
Secondary alcohol
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Polyol
Monocarboxylic acid or derivatives
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

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

160732

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

184883

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,6r,7s,7as)-6,7-dihydroxy-7-methyl-4-[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)-2-methoxyoxan-2-yl]-1h,4ah,5h,6h,7ah-cyclopenta[c]pyran-1-yl 3-methylbutanoate (NP0241872)

MOL for NP0241872 ((1s,4as,6r,7s,7as)-6,7-dihydroxy-7-methyl-4-[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)-2-methoxyoxan-2-yl]-1h,4ah,5h,6h,7ah-cyclopenta[c]pyran-1-yl 3-methylbutanoate)

3D MOL for NP0241872 ((1s,4as,6r,7s,7as)-6,7-dihydroxy-7-methyl-4-[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)-2-methoxyoxan-2-yl]-1h,4ah,5h,6h,7ah-cyclopenta[c]pyran-1-yl 3-methylbutanoate)

3D SDF for NP0241872 ((1s,4as,6r,7s,7as)-6,7-dihydroxy-7-methyl-4-[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)-2-methoxyoxan-2-yl]-1h,4ah,5h,6h,7ah-cyclopenta[c]pyran-1-yl 3-methylbutanoate)

3D-SDF for NP0241872 ((1s,4as,6r,7s,7as)-6,7-dihydroxy-7-methyl-4-[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)-2-methoxyoxan-2-yl]-1h,4ah,5h,6h,7ah-cyclopenta[c]pyran-1-yl 3-methylbutanoate)

PDB for NP0241872 ((1s,4as,6r,7s,7as)-6,7-dihydroxy-7-methyl-4-[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)-2-methoxyoxan-2-yl]-1h,4ah,5h,6h,7ah-cyclopenta[c]pyran-1-yl 3-methylbutanoate)

3D PDB for NP0241872 ((1s,4as,6r,7s,7as)-6,7-dihydroxy-7-methyl-4-[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)-2-methoxyoxan-2-yl]-1h,4ah,5h,6h,7ah-cyclopenta[c]pyran-1-yl 3-methylbutanoate)

SMILES for NP0241872 ((1s,4as,6r,7s,7as)-6,7-dihydroxy-7-methyl-4-[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)-2-methoxyoxan-2-yl]-1h,4ah,5h,6h,7ah-cyclopenta[c]pyran-1-yl 3-methylbutanoate)

INCHI for NP0241872 ((1s,4as,6r,7s,7as)-6,7-dihydroxy-7-methyl-4-[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)-2-methoxyoxan-2-yl]-1h,4ah,5h,6h,7ah-cyclopenta[c]pyran-1-yl 3-methylbutanoate)

Structure for NP0241872 ((1s,4as,6r,7s,7as)-6,7-dihydroxy-7-methyl-4-[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)-2-methoxyoxan-2-yl]-1h,4ah,5h,6h,7ah-cyclopenta[c]pyran-1-yl 3-methylbutanoate)

3D Structure for NP0241872 ((1s,4as,6r,7s,7as)-6,7-dihydroxy-7-methyl-4-[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)-2-methoxyoxan-2-yl]-1h,4ah,5h,6h,7ah-cyclopenta[c]pyran-1-yl 3-methylbutanoate)