NP-MRD: Showing NP-Card for (1r,4ar,7r,7as)-7-hydroxy-7-({[(2e)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}methyl)-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,7ah-cyclopenta[c]pyran-4-carboxylic acid (NP0253622)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-07 17:32:48 UTC

Updated at

2022-09-07 17:32:49 UTC

NP-MRD ID

NP0253622

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r,4ar,7r,7as)-7-hydroxy-7-({[(2e)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}methyl)-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,7ah-cyclopenta[c]pyran-4-carboxylic acid

Description

(1R,4aR,7R,7aS)-7-hydroxy-7-({[(2E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}methyl)-1-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1H,4aH,7H,7aH-cyclopenta[c]pyran-4-carboxylic acid belongs to the class of organic compounds known as iridoid o-glycosides. These are iridoid monoterpenes containing a glycosyl (usually a pyranosyl) moiety linked to the iridoid skeleton. (1r,4ar,7r,7as)-7-hydroxy-7-({[(2e)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}methyl)-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,7ah-cyclopenta[c]pyran-4-carboxylic acid is found in Andromeda polifolia. Based on a literature review very few articles have been published on (1R,4aR,7R,7aS)-7-hydroxy-7-({[(2E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}methyl)-1-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1H,4aH,7H,7aH-cyclopenta[c]pyran-4-carboxylic acid.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309072219322D          

 38 41  0  0  1  0            999 V2000
   -1.0047   -2.6029    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0047   -1.7779    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7192   -1.3654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4336   -1.7779    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1481   -1.3654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8626   -1.7779    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5770   -1.3654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5770   -0.5404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2915   -0.1279    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8626   -0.1279    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1481   -0.5404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2902   -1.3654    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4243   -1.7779    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387   -1.3654    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4743   -2.1191    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538   -0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387   -0.0305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233   -0.2854    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6378    0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.9521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    1.3646    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.3646    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -1.1104    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -1.5229    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6378   -2.3479    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -2.7604    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.0668   -2.3479    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812   -2.7604    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.4957   -2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4957   -1.5229    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812   -3.5854    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.4957   -3.9979    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668   -3.9979    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.0668   -4.8229    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -3.5854    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6378   -3.9979    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233   -1.1104    0.0000 C   0  0  2  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
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  2  0  0  0  0
  5 11  1  0  0  0  0
  2 12  1  0  0  0  0
 12 13  1  0  0  0  0
 14 13  1  1  0  0  0
 14 15  1  6  0  0  0
 14 16  1  0  0  0  0
 16 17  2  0  0  0  0
 18 17  1  1  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
 19 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  6  0  0  0
 27 26  1  6  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  6  0  0  0
 30 31  1  0  0  0  0
 29 32  1  0  0  0  0
 32 33  1  1  0  0  0
 32 34  1  0  0  0  0
 34 35  1  6  0  0  0
 34 36  1  0  0  0  0
 27 36  1  0  0  0  0
 36 37  1  1  0  0  0
 25 38  1  0  0  0  0
 38 18  1  6  0  0  0
 14 38  1  0  0  0  0
M  END

     RDKit          3D

 66 69  0  0  0  0  0  0  0  0999 V2000
    3.6406    2.4155   -0.9184 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6858    1.1704   -0.9161 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9693    0.5507   -0.4943 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0401   -0.7655   -0.4847 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2088   -1.5263   -0.1030 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1807   -2.9122   -0.1255 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2924   -3.6597    0.2358 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4528   -3.0581    0.6261 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5460   -3.8415    0.9810 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.4945   -1.6964    0.6529 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3747   -0.9399    0.2890 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6150    0.4531   -1.2808 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3454    0.6512   -1.6887 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3039    1.2193   -0.7669 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2240    0.4706    0.4018 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4207    2.6632   -0.5987 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7860    3.2878   -0.7119 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7858    2.2815   -0.9611 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.8158    2.5461   -1.9810 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3002    3.8850   -2.2172 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1896    4.1497   -3.0835 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8199    4.9592   -1.5098 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2772    1.5171   -2.6566 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8593    0.1820   -2.4761 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8319   -0.0516   -1.4346 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.6313    0.0359   -0.2719 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7406   -1.1461    0.4100 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.0039   -1.7184    0.3096 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9884   -1.1635    1.0682 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.6172   -0.0329    0.2411 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1176   -0.6207   -0.9127 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5910   -0.5970    2.3856 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.6319   -0.7726    3.2915 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3218   -1.3101    2.8366 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.9775   -0.9123    4.1024 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2461   -1.0242    1.8004 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1465   -1.8396    1.9977 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9877    1.1346   -1.5492 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.8147    1.1435   -0.2054 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1491   -1.3262   -0.7882 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2627   -3.3928   -0.4345 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1905   -4.7315    0.1918 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.6751   -4.1354    1.9276 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.4169   -1.2082    0.9629 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4474    0.1257    0.3230 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4089    1.4397   -2.5407 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9217   -0.2351   -2.2574 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3512   -0.4751    0.1440 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3520    3.2182   -0.3878 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8281    4.3738   -0.6043 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2658    1.8941   -0.0083 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4630    5.6337   -1.1571 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0488    1.7187   -3.4206 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4017   -1.0343   -1.5953 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0762   -1.8766   -0.1452 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8411   -1.8758    1.2527 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4380    0.4597    0.8269 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8437    0.7153   -0.0083 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8835   -0.1518   -1.3010 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3382    0.4861    2.3387 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9561    0.0969    3.6572 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5511   -2.3938    2.8525 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0439   -1.0669    4.3384 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9456    0.0516    1.9748 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4143   -2.7692    2.2005 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7785    1.3313   -2.6235 H   0  0  0  0  0  0  0  0  0  0  0  0
 31 30  1  0
 30 29  1  0
 29 28  1  0
 28 27  1  0
 27 26  1  0
 26 25  1  0
 25 24  1  0
 24 23  1  0
 23 19  2  0
 19 18  1  0
 18 17  1  0
 17 16  2  0
 16 14  1  0
 14 15  1  1
 14 13  1  0
 13 12  1  0
 12  2  1  0
  2  1  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  8 10  1  0
 10 11  2  0
 14 38  1  0
 19 20  1  0
 20 22  1  0
 20 21  2  0
 27 36  1  0
 36 37  1  0
 36 34  1  0
 34 35  1  0
 34 32  1  0
 32 33  1  0
 32 29  1  0
 38 25  1  0
 38 18  1  0
 11  5  1  0
 31 59  1  0
 30 57  1  0
 30 58  1  0
 29 56  1  1
 27 55  1  6
 25 54  1  6
 23 53  1  0
 18 51  1  1
 17 50  1  0
 16 49  1  0
 15 48  1  0
 13 46  1  0
 13 47  1  0
  3 39  1  0
  4 40  1  0
  6 41  1  0
  7 42  1  0
  9 43  1  0
 10 44  1  0
 11 45  1  0
 38 66  1  6
 22 52  1  0
 36 64  1  1
 37 65  1  0
 34 62  1  1
 35 63  1  0
 32 60  1  6
 33 61  1  0
M  END


  Mrv1652309072219322D          

 38 41  0  0  1  0            999 V2000
   -1.0047   -2.6029    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0047   -1.7779    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7192   -1.3654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4336   -1.7779    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1481   -1.3654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8626   -1.7779    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5770   -1.3654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5770   -0.5404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2915   -0.1279    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8626   -0.1279    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1481   -0.5404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2902   -1.3654    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4243   -1.7779    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387   -1.3654    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4743   -2.1191    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538   -0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387   -0.0305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233   -0.2854    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6378    0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.9521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    1.3646    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.3646    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -1.1104    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -1.5229    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6378   -2.3479    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -2.7604    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.0668   -2.3479    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812   -2.7604    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.4957   -2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4957   -1.5229    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812   -3.5854    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.4957   -3.9979    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668   -3.9979    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.0668   -4.8229    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -3.5854    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6378   -3.9979    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233   -1.1104    0.0000 C   0  0  2  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
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  2  0  0  0  0
  5 11  1  0  0  0  0
  2 12  1  0  0  0  0
 12 13  1  0  0  0  0
 14 13  1  1  0  0  0
 14 15  1  6  0  0  0
 14 16  1  0  0  0  0
 16 17  2  0  0  0  0
 18 17  1  1  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
 19 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  6  0  0  0
 27 26  1  6  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  6  0  0  0
 30 31  1  0  0  0  0
 29 32  1  0  0  0  0
 32 33  1  1  0  0  0
 32 34  1  0  0  0  0
 34 35  1  6  0  0  0
 34 36  1  0  0  0  0
 27 36  1  0  0  0  0
 36 37  1  1  0  0  0
 25 38  1  0  0  0  0
 38 18  1  6  0  0  0
 14 38  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0253622

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC[C@H]1O[C@@H](O[C@H]2OC=C([C@@H]3C=C[C@](O)(COC(=O)\C=C\C4=CC=C(O)C=C4)[C@@H]23)C(O)=O)[C@H](O)[C@@H](O)[C@@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C25H28O13/c26-9-16-19(29)20(30)21(31)24(37-16)38-23-18-14(15(10-35-23)22(32)33)7-8-25(18,34)11-36-17(28)6-3-12-1-4-13(27)5-2-12/h1-8,10,14,16,18-21,23-24,26-27,29-31,34H,9,11H2,(H,32,33)/b6-3+/t14-,16+,18+,19+,20-,21+,23+,24-,25-/m0/s1

> <INCHI_KEY>
WJPRKOJNQIZCGY-ZYCVDZNZSA-N

> <FORMULA>
C25H28O13

> <MOLECULAR_WEIGHT>
536.486

> <EXACT_MASS>
536.152990962

> <JCHEM_ACCEPTOR_COUNT>
12

> <JCHEM_ATOM_COUNT>
66

> <JCHEM_AVERAGE_POLARIZABILITY>
51.991462147787786

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,4aR,7R,7aS)-7-hydroxy-7-({[(2E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}methyl)-1-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1H,4aH,7H,7aH-cyclopenta[c]pyran-4-carboxylic acid

> <JCHEM_LOGP>
-0.5622886276666665

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
9.397900300827887

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.0966800307769455

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9810847602026636

> <JCHEM_POLAR_SURFACE_AREA>
212.67

> <JCHEM_REFRACTIVITY>
126.56599999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(1R,4aR,7R,7aS)-7-hydroxy-7-({[(2E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}methyl)-1-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1H,4aH,7aH-cyclopenta[c]pyran-4-carboxylic acid

> <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  O   UNK     0      -1.875  -4.859   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      -1.875  -3.319   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -3.209  -2.549   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -4.543  -3.319   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -5.876  -2.549   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -7.210  -3.319   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -8.544  -2.549   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -8.544  -1.009   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -9.877  -0.239   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      -7.210  -0.239   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -5.876  -1.009   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -0.542  -2.549   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       0.792  -3.319   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.126  -2.549   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       2.752  -3.956   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       1.220  -1.303   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.126  -0.057   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.590  -0.533   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.924   0.237   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.924   1.777   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       6.258   2.547   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       3.590   2.547   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       6.258  -0.533   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       6.258  -2.073   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       4.924  -2.843   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       4.924  -4.383   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       6.258  -5.153   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       7.591  -4.383   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       8.925  -5.153   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      10.259  -4.383   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      10.259  -2.843   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       8.925  -6.693   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      10.259  -7.463   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       7.591  -7.463   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0       7.591  -9.003   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0       6.258  -6.693   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0       4.924  -7.463   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0       3.590  -2.073   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   12                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   11                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10    5                                                       
CONECT   12    2   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   16   38                                             
CONECT   15   14                                                            
CONECT   16   14   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   38                                                  
CONECT   19   18   20   23                                                  
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20                                                            
CONECT   23   19   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26   38                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28   36                                                  
CONECT   28   27   29                                                       
CONECT   29   28   30   32                                                  
CONECT   30   29   31                                                       
CONECT   31   30                                                            
CONECT   32   29   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32   35   36                                                  
CONECT   35   34                                                            
CONECT   36   34   27   37                                                  
CONECT   37   36                                                            
CONECT   38   25   18   14                                                  
MASTER        0    0    0    0    0    0    0    0   38    0   82    0
END

View in JSmol

Synonyms

Value	Source
(1R,4AR,7R,7as)-7-hydroxy-7-({[(2E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}methyl)-1-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1H,4ah,7H,7ah-cyclopenta[c]pyran-4-carboxylate	Generator

Chemical Formula

C₂₅H₂₈O₁₃

Average Mass

536.4860 Da

Monoisotopic Mass

536.15299 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

OC[C@H]1O[C@@H](O[C@H]2OC=C([C@@H]3C=C[C@](O)(COC(=O)\C=C\C4=CC=C(O)C=C4)[C@@H]23)C(O)=O)[C@H](O)[C@@H](O)[C@@H]1O

InChI Identifier

InChI=1S/C25H28O13/c26-9-16-19(29)20(30)21(31)24(37-16)38-23-18-14(15(10-35-23)22(32)33)7-8-25(18,34)11-36-17(28)6-3-12-1-4-13(27)5-2-12/h1-8,10,14,16,18-21,23-24,26-27,29-31,34H,9,11H2,(H,32,33)/b6-3+/t14-,16+,18+,19+,20-,21+,23+,24-,25-/m0/s1

InChI Key

WJPRKOJNQIZCGY-ZYCVDZNZSA-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
Andromeda polifolia	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as iridoid o-glycosides. These are iridoid monoterpenes containing a glycosyl (usually a pyranosyl) moiety linked to the iridoid skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene glycosides

Direct Parent

Iridoid O-glycosides

Alternative Parents

Substituents

Iridoid o-glycoside
Coumaric acid ester
Cinnamic acid or derivatives
Coumaric acid or derivatives
Hexose monosaccharide
Hydroxycinnamic acid or derivatives
Cinnamic acid ester
Glycosyl compound
Iridoid-skeleton
O-glycosyl compound
Monoterpenoid
Bicyclic monoterpenoid
Aromatic monoterpenoid
Styrene
Fatty acid ester
Phenol
1-hydroxy-2-unsubstituted benzenoid
Benzenoid
Fatty acyl
Oxane
Monocyclic benzene moiety
Monosaccharide
Dicarboxylic acid or derivatives
Vinylogous ester
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Tertiary alcohol
Secondary alcohol
Carboxylic acid ester
Oxacycle
Carboxylic acid
Organoheterocyclic compound
Carboxylic acid derivative
Polyol
Acetal
Organic oxide
Organic oxygen compound
Alcohol
Carbonyl group
Organooxygen compound
Primary alcohol
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic 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

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

163185883

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,7r,7as)-7-hydroxy-7-({[(2e)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}methyl)-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,7ah-cyclopenta[c]pyran-4-carboxylic acid (NP0253622)

MOL for NP0253622 ((1r,4ar,7r,7as)-7-hydroxy-7-({[(2e)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}methyl)-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,7ah-cyclopenta[c]pyran-4-carboxylic acid)

3D MOL for NP0253622 ((1r,4ar,7r,7as)-7-hydroxy-7-({[(2e)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}methyl)-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,7ah-cyclopenta[c]pyran-4-carboxylic acid)

3D SDF for NP0253622 ((1r,4ar,7r,7as)-7-hydroxy-7-({[(2e)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}methyl)-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,7ah-cyclopenta[c]pyran-4-carboxylic acid)

3D-SDF for NP0253622 ((1r,4ar,7r,7as)-7-hydroxy-7-({[(2e)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}methyl)-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,7ah-cyclopenta[c]pyran-4-carboxylic acid)

PDB for NP0253622 ((1r,4ar,7r,7as)-7-hydroxy-7-({[(2e)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}methyl)-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,7ah-cyclopenta[c]pyran-4-carboxylic acid)

3D PDB for NP0253622 ((1r,4ar,7r,7as)-7-hydroxy-7-({[(2e)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}methyl)-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,7ah-cyclopenta[c]pyran-4-carboxylic acid)

SMILES for NP0253622 ((1r,4ar,7r,7as)-7-hydroxy-7-({[(2e)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}methyl)-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,7ah-cyclopenta[c]pyran-4-carboxylic acid)

INCHI for NP0253622 ((1r,4ar,7r,7as)-7-hydroxy-7-({[(2e)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}methyl)-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,7ah-cyclopenta[c]pyran-4-carboxylic acid)

Structure for NP0253622 ((1r,4ar,7r,7as)-7-hydroxy-7-({[(2e)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}methyl)-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,7ah-cyclopenta[c]pyran-4-carboxylic acid)

3D Structure for NP0253622 ((1r,4ar,7r,7as)-7-hydroxy-7-({[(2e)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}methyl)-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,7ah-cyclopenta[c]pyran-4-carboxylic acid)