NP-MRD: Showing NP-Card for 7,8-dehydropenstemoside (NP0032618)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2021-06-19 23:22:34 UTC

Updated at

2021-06-30 00:01:55 UTC

NP-MRD ID

NP0032618

Secondary Accession Numbers

None

Natural Product Identification

Common Name

7,8-dehydropenstemoside

Provided By

JEOL Database JEOL Logo

Description

7,8-Dehydropenstemoside 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. 7,8-dehydropenstemoside is found in Phlomoides rotata and Lamium garganicum. 7,8-dehydropenstemoside was first documented in 2007 (Jensen, S. R., et al.). Based on a literature review very few articles have been published on 7,8-Dehydropenstemoside.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306202101223D          

 52 54  0  0  0  0            999 V2000
   -4.1944    4.0837    2.4345 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7094    2.9861    1.6596 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8696    3.3436    0.6579 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4960    4.4828    0.4096 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4209    2.1692   -0.1248 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4584    0.9334    0.3907 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9991   -0.1964   -0.2278 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0641    0.0277   -1.2945 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9203   -1.1888   -2.0392 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1643   -2.1676   -1.3242 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2109   -1.7862   -1.2851 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0206   -2.7522   -0.5827 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.4503   -2.2037   -0.5299 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.4399   -0.9068    0.0733 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9720   -4.1161   -1.2825 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.7066   -5.0974   -0.5504 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5190   -4.5752   -1.4196 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4821   -5.7862   -2.1908 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3282   -3.4951   -2.0862 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6967   -3.9297   -2.1051 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5297    1.1257   -2.2658 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4135    1.6114   -3.1766 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0500    0.8092   -4.3414 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0518    2.8093   -2.7962 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6509    3.3236   -1.5848 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9962    4.6838   -1.8129 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9236    2.4228   -1.5133 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.0021    3.0390   -2.2559 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3659    4.5915    2.9382 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8723    3.6877    3.1956 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7521    4.7826    1.8033 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8754    0.6823    1.3596 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0976    0.3044   -0.8495 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5650   -2.2663   -0.3068 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6488   -2.8248    0.4481 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8679   -2.0894   -1.5357 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1103   -2.8492    0.0566 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7759   -0.3958   -0.4264 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4242   -4.0489   -2.2802 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4800   -5.9543   -0.9672 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1071   -4.8382   -0.4371 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4659   -5.9355   -2.3860 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0259   -3.3768   -3.1343 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2135   -3.1558   -2.4076 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3692    0.7673   -2.8766 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5187   -0.1221   -4.0113 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7929    0.5644   -4.9950 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7859    1.3588   -4.9376 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8482    3.3539   -3.2858 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0003    3.2400   -0.7070 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5026    4.9697   -1.0195 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6041    3.8156   -2.7026 H   0  0  0  0  0  0  0  0  0  0  0  0
 27  5  1  0  0  0  0
 21  8  1  0  0  0  0
  8  7  1  0  0  0  0
  7  6  1  0  0  0  0
  6  5  2  0  0  0  0
 21 27  1  0  0  0  0
 12 11  1  0  0  0  0
 11 10  1  0  0  0  0
 15 16  1  0  0  0  0
 17 18  1  0  0  0  0
 27 25  1  0  0  0  0
 25 24  1  0  0  0  0
 24 22  2  0  0  0  0
 22 21  1  0  0  0  0
 19 20  1  0  0  0  0
 27 28  1  6  0  0  0
 21 45  1  6  0  0  0
  5  3  1  0  0  0  0
  8  9  1  0  0  0  0
 13 14  1  0  0  0  0
  3  2  1  0  0  0  0
 10 19  1  0  0  0  0
  2  1  1  0  0  0  0
 19 17  1  0  0  0  0
 22 23  1  0  0  0  0
 17 15  1  0  0  0  0
  3  4  2  0  0  0  0
 15 12  1  0  0  0  0
 25 26  1  0  0  0  0
 12 13  1  0  0  0  0
 10  9  1  0  0  0  0
 10 34  1  1  0  0  0
 15 39  1  6  0  0  0
 16 40  1  0  0  0  0
 17 41  1  1  0  0  0
 18 42  1  0  0  0  0
 19 43  1  6  0  0  0
 20 44  1  0  0  0  0
 13 36  1  0  0  0  0
 13 37  1  0  0  0  0
 12 35  1  1  0  0  0
 14 38  1  0  0  0  0
  8 33  1  1  0  0  0
  6 32  1  0  0  0  0
 25 50  1  1  0  0  0
 24 49  1  0  0  0  0
 28 52  1  0  0  0  0
  1 29  1  0  0  0  0
  1 30  1  0  0  0  0
  1 31  1  0  0  0  0
 23 46  1  0  0  0  0
 23 47  1  0  0  0  0
 23 48  1  0  0  0  0
 26 51  1  0  0  0  0
M  END

     RDKit          3D

 52 54  0  0  0  0  0  0  0  0999 V2000
   -4.1944    4.0837    2.4345 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7094    2.9861    1.6596 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8696    3.3436    0.6579 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4960    4.4828    0.4096 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4209    2.1692   -0.1248 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4584    0.9334    0.3907 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9991   -0.1964   -0.2278 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0641    0.0277   -1.2945 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9203   -1.1888   -2.0392 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1643   -2.1676   -1.3242 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2109   -1.7862   -1.2851 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0206   -2.7522   -0.5827 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.4503   -2.2037   -0.5299 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4399   -0.9068    0.0733 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9720   -4.1161   -1.2825 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.7066   -5.0974   -0.5504 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5190   -4.5752   -1.4196 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4821   -5.7862   -2.1908 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3282   -3.4951   -2.0862 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6967   -3.9297   -2.1051 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5297    1.1257   -2.2658 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4135    1.6114   -3.1766 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0500    0.8092   -4.3414 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0518    2.8093   -2.7962 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6509    3.3236   -1.5848 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9962    4.6838   -1.8129 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9236    2.4228   -1.5133 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.0021    3.0390   -2.2559 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3659    4.5915    2.9382 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8723    3.6877    3.1956 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7521    4.7826    1.8033 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8754    0.6823    1.3596 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0976    0.3044   -0.8495 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5650   -2.2663   -0.3068 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6488   -2.8248    0.4481 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8679   -2.0894   -1.5357 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1103   -2.8492    0.0566 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7759   -0.3958   -0.4264 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4242   -4.0489   -2.2802 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4800   -5.9543   -0.9672 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1071   -4.8382   -0.4371 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4659   -5.9355   -2.3860 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0259   -3.3768   -3.1343 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2135   -3.1558   -2.4076 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3692    0.7673   -2.8766 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5187   -0.1221   -4.0113 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7929    0.5644   -4.9950 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7859    1.3588   -4.9376 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8482    3.3539   -3.2858 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0003    3.2400   -0.7070 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5026    4.9697   -1.0195 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6041    3.8156   -2.7026 H   0  0  0  0  0  0  0  0  0  0  0  0
 27  5  1  0
 21  8  1  0
  8  7  1  0
  7  6  1  0
  6  5  2  0
 21 27  1  0
 12 11  1  0
 11 10  1  0
 15 16  1  0
 17 18  1  0
 27 25  1  0
 25 24  1  0
 24 22  2  0
 22 21  1  0
 19 20  1  0
 27 28  1  6
 21 45  1  6
  5  3  1  0
  8  9  1  0
 13 14  1  0
  3  2  1  0
 10 19  1  0
  2  1  1  0
 19 17  1  0
 22 23  1  0
 17 15  1  0
  3  4  2  0
 15 12  1  0
 25 26  1  0
 12 13  1  0
 10  9  1  0
 10 34  1  1
 15 39  1  6
 16 40  1  0
 17 41  1  1
 18 42  1  0
 19 43  1  6
 20 44  1  0
 13 36  1  0
 13 37  1  0
 12 35  1  1
 14 38  1  0
  8 33  1  1
  6 32  1  0
 25 50  1  1
 24 49  1  0
 28 52  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
 23 46  1  0
 23 47  1  0
 23 48  1  0
 26 51  1  0
M  END


  Mrv1652306202101223D          

 52 54  0  0  0  0            999 V2000
   -4.1944    4.0837    2.4345 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7094    2.9861    1.6596 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8696    3.3436    0.6579 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4960    4.4828    0.4096 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4209    2.1692   -0.1248 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4584    0.9334    0.3907 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9991   -0.1964   -0.2278 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0641    0.0277   -1.2945 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9203   -1.1888   -2.0392 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1643   -2.1676   -1.3242 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2109   -1.7862   -1.2851 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0206   -2.7522   -0.5827 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.4503   -2.2037   -0.5299 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.4399   -0.9068    0.0733 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9720   -4.1161   -1.2825 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.7066   -5.0974   -0.5504 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5190   -4.5752   -1.4196 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4821   -5.7862   -2.1908 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3282   -3.4951   -2.0862 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6967   -3.9297   -2.1051 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5297    1.1257   -2.2658 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4135    1.6114   -3.1766 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0500    0.8092   -4.3414 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0518    2.8093   -2.7962 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6509    3.3236   -1.5848 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9962    4.6838   -1.8129 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9236    2.4228   -1.5133 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.0021    3.0390   -2.2559 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3659    4.5915    2.9382 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8723    3.6877    3.1956 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7521    4.7826    1.8033 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8754    0.6823    1.3596 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0976    0.3044   -0.8495 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5650   -2.2663   -0.3068 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6488   -2.8248    0.4481 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8679   -2.0894   -1.5357 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1103   -2.8492    0.0566 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7759   -0.3958   -0.4264 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4242   -4.0489   -2.2802 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4800   -5.9543   -0.9672 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1071   -4.8382   -0.4371 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4659   -5.9355   -2.3860 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0259   -3.3768   -3.1343 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2135   -3.1558   -2.4076 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3692    0.7673   -2.8766 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5187   -0.1221   -4.0113 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7929    0.5644   -4.9950 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7859    1.3588   -4.9376 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8482    3.3539   -3.2858 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0003    3.2400   -0.7070 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5026    4.9697   -1.0195 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6041    3.8156   -2.7026 H   0  0  0  0  0  0  0  0  0  0  0  0
 27  5  1  0  0  0  0
 21  8  1  0  0  0  0
  8  7  1  0  0  0  0
  7  6  1  0  0  0  0
  6  5  2  0  0  0  0
 21 27  1  0  0  0  0
 12 11  1  0  0  0  0
 11 10  1  0  0  0  0
 15 16  1  0  0  0  0
 17 18  1  0  0  0  0
 27 25  1  0  0  0  0
 25 24  1  0  0  0  0
 24 22  2  0  0  0  0
 22 21  1  0  0  0  0
 19 20  1  0  0  0  0
 27 28  1  6  0  0  0
 21 45  1  6  0  0  0
  5  3  1  0  0  0  0
  8  9  1  0  0  0  0
 13 14  1  0  0  0  0
  3  2  1  0  0  0  0
 10 19  1  0  0  0  0
  2  1  1  0  0  0  0
 19 17  1  0  0  0  0
 22 23  1  0  0  0  0
 17 15  1  0  0  0  0
  3  4  2  0  0  0  0
 15 12  1  0  0  0  0
 25 26  1  0  0  0  0
 12 13  1  0  0  0  0
 10  9  1  0  0  0  0
 10 34  1  1  0  0  0
 15 39  1  6  0  0  0
 16 40  1  0  0  0  0
 17 41  1  1  0  0  0
 18 42  1  0  0  0  0
 19 43  1  6  0  0  0
 20 44  1  0  0  0  0
 13 36  1  0  0  0  0
 13 37  1  0  0  0  0
 12 35  1  1  0  0  0
 14 38  1  0  0  0  0
  8 33  1  1  0  0  0
  6 32  1  0  0  0  0
 25 50  1  1  0  0  0
 24 49  1  0  0  0  0
 28 52  1  0  0  0  0
  1 29  1  0  0  0  0
  1 30  1  0  0  0  0
  1 31  1  0  0  0  0
 23 46  1  0  0  0  0
 23 47  1  0  0  0  0
 23 48  1  0  0  0  0
 26 51  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0032618

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C17H24O11/c1-6-3-9(19)17(24)7(14(23)25-2)5-26-15(10(6)17)28-16-13(22)12(21)11(20)8(4-18)27-16/h3,5,8-13,15-16,18-22,24H,4H2,1-2H3/t8-,9-,10+,11-,12+,13-,15+,16+,17-/m1/s1

> <INCHI_KEY>
WUZGENDUAYSYJW-BKDJBYHXSA-N

> <FORMULA>
C17H24O11

> <MOLECULAR_WEIGHT>
404.368

> <EXACT_MASS>
404.131861593

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
52

> <JCHEM_AVERAGE_POLARIZABILITY>
38.911409840366986

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
-1.53

> <JCHEM_LOGP>
-2.7511769096666665

> <ALOGPS_LOGS>
-1.02

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.544970839265133

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.989130076806084

> <JCHEM_PKA_STRONGEST_BASIC>
-2.981084761605876

> <JCHEM_POLAR_SURFACE_AREA>
175.37

> <JCHEM_REFRACTIVITY>
89.10669999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.86e+01 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 52 54  0  0  0  0  0  0  0  0999 V2000
   -4.1944    4.0837    2.4345 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7094    2.9861    1.6596 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8696    3.3436    0.6579 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4960    4.4828    0.4096 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4209    2.1692   -0.1248 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4584    0.9334    0.3907 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9991   -0.1964   -0.2278 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0641    0.0277   -1.2945 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9203   -1.1888   -2.0392 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1643   -2.1676   -1.3242 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2109   -1.7862   -1.2851 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0206   -2.7522   -0.5827 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.4503   -2.2037   -0.5299 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4399   -0.9068    0.0733 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9720   -4.1161   -1.2825 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.7066   -5.0974   -0.5504 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5190   -4.5752   -1.4196 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4821   -5.7862   -2.1908 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3282   -3.4951   -2.0862 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6967   -3.9297   -2.1051 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5297    1.1257   -2.2658 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4135    1.6114   -3.1766 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0500    0.8092   -4.3414 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0518    2.8093   -2.7962 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6509    3.3236   -1.5848 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9962    4.6838   -1.8129 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9236    2.4228   -1.5133 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.0021    3.0390   -2.2559 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3659    4.5915    2.9382 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8723    3.6877    3.1956 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7521    4.7826    1.8033 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8754    0.6823    1.3596 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0976    0.3044   -0.8495 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5650   -2.2663   -0.3068 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6488   -2.8248    0.4481 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8679   -2.0894   -1.5357 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1103   -2.8492    0.0566 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7759   -0.3958   -0.4264 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4242   -4.0489   -2.2802 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4800   -5.9543   -0.9672 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1071   -4.8382   -0.4371 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4659   -5.9355   -2.3860 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0259   -3.3768   -3.1343 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2135   -3.1558   -2.4076 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3692    0.7673   -2.8766 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5187   -0.1221   -4.0113 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7929    0.5644   -4.9950 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7859    1.3588   -4.9376 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8482    3.3539   -3.2858 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0003    3.2400   -0.7070 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5026    4.9697   -1.0195 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6041    3.8156   -2.7026 H   0  0  0  0  0  0  0  0  0  0  0  0
 27  5  1  0
 21  8  1  0
  8  7  1  0
  7  6  1  0
  6  5  2  0
 21 27  1  0
 12 11  1  0
 11 10  1  0
 15 16  1  0
 17 18  1  0
 27 25  1  0
 25 24  1  0
 24 22  2  0
 22 21  1  0
 19 20  1  0
 27 28  1  6
 21 45  1  6
  5  3  1  0
  8  9  1  0
 13 14  1  0
  3  2  1  0
 10 19  1  0
  2  1  1  0
 19 17  1  0
 22 23  1  0
 17 15  1  0
  3  4  2  0
 15 12  1  0
 25 26  1  0
 12 13  1  0
 10  9  1  0
 10 34  1  1
 15 39  1  6
 16 40  1  0
 17 41  1  1
 18 42  1  0
 19 43  1  6
 20 44  1  0
 13 36  1  0
 13 37  1  0
 12 35  1  1
 14 38  1  0
  8 33  1  1
  6 32  1  0
 25 50  1  1
 24 49  1  0
 28 52  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
 23 46  1  0
 23 47  1  0
 23 48  1  0
 26 51  1  0
M  END

HEADER    PROTEIN                                 20-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-JUN-21         0                                  
HETATM    1  C   UNK     0      -4.194   4.084   2.434  0.00  0.00           C+0
HETATM    2  O   UNK     0      -3.709   2.986   1.660  0.00  0.00           O+0
HETATM    3  C   UNK     0      -2.870   3.344   0.658  0.00  0.00           C+0
HETATM    4  O   UNK     0      -2.496   4.483   0.410  0.00  0.00           O+0
HETATM    5  C   UNK     0      -2.421   2.169  -0.125  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.458   0.933   0.391  0.00  0.00           C+0
HETATM    7  O   UNK     0      -1.999  -0.196  -0.228  0.00  0.00           O+0
HETATM    8  C   UNK     0      -1.064   0.028  -1.295  0.00  0.00           C+0
HETATM    9  O   UNK     0      -0.920  -1.189  -2.039  0.00  0.00           O+0
HETATM   10  C   UNK     0      -0.164  -2.168  -1.324  0.00  0.00           C+0
HETATM   11  O   UNK     0       1.211  -1.786  -1.285  0.00  0.00           O+0
HETATM   12  C   UNK     0       2.021  -2.752  -0.583  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.450  -2.204  -0.530  0.00  0.00           C+0
HETATM   14  O   UNK     0       3.440  -0.907   0.073  0.00  0.00           O+0
HETATM   15  C   UNK     0       1.972  -4.116  -1.283  0.00  0.00           C+0
HETATM   16  O   UNK     0       2.707  -5.097  -0.550  0.00  0.00           O+0
HETATM   17  C   UNK     0       0.519  -4.575  -1.420  0.00  0.00           C+0
HETATM   18  O   UNK     0       0.482  -5.786  -2.191  0.00  0.00           O+0
HETATM   19  C   UNK     0      -0.328  -3.495  -2.086  0.00  0.00           C+0
HETATM   20  O   UNK     0      -1.697  -3.930  -2.105  0.00  0.00           O+0
HETATM   21  C   UNK     0      -1.530   1.126  -2.266  0.00  0.00           C+0
HETATM   22  C   UNK     0      -0.414   1.611  -3.177  0.00  0.00           C+0
HETATM   23  C   UNK     0       0.050   0.809  -4.341  0.00  0.00           C+0
HETATM   24  C   UNK     0       0.052   2.809  -2.796  0.00  0.00           C+0
HETATM   25  C   UNK     0      -0.651   3.324  -1.585  0.00  0.00           C+0
HETATM   26  O   UNK     0      -0.996   4.684  -1.813  0.00  0.00           O+0
HETATM   27  C   UNK     0      -1.924   2.423  -1.513  0.00  0.00           C+0
HETATM   28  O   UNK     0      -3.002   3.039  -2.256  0.00  0.00           O+0
HETATM   29  H   UNK     0      -3.366   4.591   2.938  0.00  0.00           H+0
HETATM   30  H   UNK     0      -4.872   3.688   3.196  0.00  0.00           H+0
HETATM   31  H   UNK     0      -4.752   4.783   1.803  0.00  0.00           H+0
HETATM   32  H   UNK     0      -2.875   0.682   1.360  0.00  0.00           H+0
HETATM   33  H   UNK     0      -0.098   0.304  -0.850  0.00  0.00           H+0
HETATM   34  H   UNK     0      -0.565  -2.266  -0.307  0.00  0.00           H+0
HETATM   35  H   UNK     0       1.649  -2.825   0.448  0.00  0.00           H+0
HETATM   36  H   UNK     0       3.868  -2.089  -1.536  0.00  0.00           H+0
HETATM   37  H   UNK     0       4.110  -2.849   0.057  0.00  0.00           H+0
HETATM   38  H   UNK     0       2.776  -0.396  -0.426  0.00  0.00           H+0
HETATM   39  H   UNK     0       2.424  -4.049  -2.280  0.00  0.00           H+0
HETATM   40  H   UNK     0       2.480  -5.954  -0.967  0.00  0.00           H+0
HETATM   41  H   UNK     0       0.107  -4.838  -0.437  0.00  0.00           H+0
HETATM   42  H   UNK     0      -0.466  -5.936  -2.386  0.00  0.00           H+0
HETATM   43  H   UNK     0      -0.026  -3.377  -3.134  0.00  0.00           H+0
HETATM   44  H   UNK     0      -2.213  -3.156  -2.408  0.00  0.00           H+0
HETATM   45  H   UNK     0      -2.369   0.767  -2.877  0.00  0.00           H+0
HETATM   46  H   UNK     0       0.519  -0.122  -4.011  0.00  0.00           H+0
HETATM   47  H   UNK     0      -0.793   0.564  -4.995  0.00  0.00           H+0
HETATM   48  H   UNK     0       0.786   1.359  -4.938  0.00  0.00           H+0
HETATM   49  H   UNK     0       0.848   3.354  -3.286  0.00  0.00           H+0
HETATM   50  H   UNK     0      -0.000   3.240  -0.707  0.00  0.00           H+0
HETATM   51  H   UNK     0      -1.503   4.970  -1.020  0.00  0.00           H+0
HETATM   52  H   UNK     0      -2.604   3.816  -2.703  0.00  0.00           H+0
CONECT    1    2   29   30   31                                             
CONECT    2    3    1                                                       
CONECT    3    5    2    4                                                  
CONECT    4    3                                                            
CONECT    5   27    6    3                                                  
CONECT    6    7    5   32                                                  
CONECT    7    8    6                                                       
CONECT    8   21    7    9   33                                             
CONECT    9    8   10                                                       
CONECT   10   11   19    9   34                                             
CONECT   11   12   10                                                       
CONECT   12   11   15   13   35                                             
CONECT   13   14   12   36   37                                             
CONECT   14   13   38                                                       
CONECT   15   16   17   12   39                                             
CONECT   16   15   40                                                       
CONECT   17   18   19   15   41                                             
CONECT   18   17   42                                                       
CONECT   19   20   10   17   43                                             
CONECT   20   19   44                                                       
CONECT   21    8   27   22   45                                             
CONECT   22   24   21   23                                                  
CONECT   23   22   46   47   48                                             
CONECT   24   25   22   49                                                  
CONECT   25   27   24   26   50                                             
CONECT   26   25   51                                                       
CONECT   27    5   21   25   28                                             
CONECT   28   27   52                                                       
CONECT   29    1                                                            
CONECT   30    1                                                            
CONECT   31    1                                                            
CONECT   32    6                                                            
CONECT   33    8                                                            
CONECT   34   10                                                            
CONECT   35   12                                                            
CONECT   36   13                                                            
CONECT   37   13                                                            
CONECT   38   14                                                            
CONECT   39   15                                                            
CONECT   40   16                                                            
CONECT   41   17                                                            
CONECT   42   18                                                            
CONECT   43   19                                                            
CONECT   44   20                                                            
CONECT   45   21                                                            
CONECT   46   23                                                            
CONECT   47   23                                                            
CONECT   48   23                                                            
CONECT   49   24                                                            
CONECT   50   25                                                            
CONECT   51   26                                                            
CONECT   52   28                                                            
MASTER        0    0    0    0    0    0    0    0   52    0  108    0
END

RDKit          3D

52 54  0  0  0  0  0  0  0  0999 V2000
   -4.1944    4.0837    2.4345 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7094    2.9861    1.6596 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8696    3.3436    0.6579 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4960    4.4828    0.4096 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4209    2.1692   -0.1248 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4584    0.9334    0.3907 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9991   -0.1964   -0.2278 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0641    0.0277   -1.2945 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9203   -1.1888   -2.0392 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1643   -2.1676   -1.3242 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2109   -1.7862   -1.2851 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0206   -2.7522   -0.5827 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.4503   -2.2037   -0.5299 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4399   -0.9068    0.0733 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9720   -4.1161   -1.2825 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.7066   -5.0974   -0.5504 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5190   -4.5752   -1.4196 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4821   -5.7862   -2.1908 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3282   -3.4951   -2.0862 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6967   -3.9297   -2.1051 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5297    1.1257   -2.2658 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4135    1.6114   -3.1766 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0500    0.8092   -4.3414 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0518    2.8093   -2.7962 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6509    3.3236   -1.5848 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9962    4.6838   -1.8129 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9236    2.4228   -1.5133 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.0021    3.0390   -2.2559 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3659    4.5915    2.9382 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8723    3.6877    3.1956 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7521    4.7826    1.8033 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8754    0.6823    1.3596 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0976    0.3044   -0.8495 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5650   -2.2663   -0.3068 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6488   -2.8248    0.4481 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8679   -2.0894   -1.5357 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1103   -2.8492    0.0566 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7759   -0.3958   -0.4264 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4242   -4.0489   -2.2802 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4800   -5.9543   -0.9672 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1071   -4.8382   -0.4371 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4659   -5.9355   -2.3860 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0259   -3.3768   -3.1343 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2135   -3.1558   -2.4076 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3692    0.7673   -2.8766 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5187   -0.1221   -4.0113 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7929    0.5644   -4.9950 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7859    1.3588   -4.9376 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8482    3.3539   -3.2858 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0003    3.2400   -0.7070 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5026    4.9697   -1.0195 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6041    3.8156   -2.7026 H   0  0  0  0  0  0  0  0  0  0  0  0
 27  5  1  0
 21  8  1  0
  8  7  1  0
  7  6  1  0
  6  5  2  0
 21 27  1  0
 12 11  1  0
 11 10  1  0
 15 16  1  0
 17 18  1  0
 27 25  1  0
 25 24  1  0
 24 22  2  0
 22 21  1  0
 19 20  1  0
 27 28  1  6
 21 45  1  6
  5  3  1  0
  8  9  1  0
 13 14  1  0
  3  2  1  0
 10 19  1  0
  2  1  1  0
 19 17  1  0
 22 23  1  0
 17 15  1  0
  3  4  2  0
 15 12  1  0
 25 26  1  0
 12 13  1  0
 10  9  1  0
 10 34  1  1
 15 39  1  6
 16 40  1  0
 17 41  1  1
 18 42  1  0
 19 43  1  6
 20 44  1  0
 13 36  1  0
 13 37  1  0
 12 35  1  1
 14 38  1  0
  8 33  1  1
  6 32  1  0
 25 50  1  1
 24 49  1  0
 28 52  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
 23 46  1  0
 23 47  1  0
 23 48  1  0
 26 51  1  0
M  END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₇H₂₄O₁₁

Average Mass

404.3680 Da

Monoisotopic Mass

404.13186 Da

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

[H]OC([H])([H])[C@@]1([H])O[C@@]([H])(O[C@]2([H])OC([H])=C(C(=O)OC([H])([H])[H])[C@@]3(O[H])[C@]([H])(O[H])C([H])=C(C([H])([H])[H])[C@@]23[H])[C@]([H])(O[H])[C@@]([H])(O[H])[C@]1([H])O[H]

InChI Identifier

InChI=1S/C17H24O11/c1-6-3-9(19)17(24)7(14(23)25-2)5-26-15(10(6)17)28-16-13(22)12(21)11(20)8(4-18)27-16/h3,5,8-13,15-16,18-22,24H,4H2,1-2H3/t8-,9-,10+,11-,12+,13-,15+,16+,17-/m1/s1

InChI Key

WUZGENDUAYSYJW-BKDJBYHXSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Lamiophlomis rotata	LOTUS Database	35616633
Lamium garganicum	JEOL database	Jensen, S. R., et al, J. Nat. Prod. 70, 29 (2007)

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
Hexose monosaccharide
Glycosyl compound
Iridoid-skeleton
O-glycosyl compound
Bicyclic monoterpenoid
Monoterpenoid
Monosaccharide
Oxane
Methyl ester
Tertiary alcohol
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Vinylogous ester
Secondary alcohol
Carboxylic acid ester
Polyol
Carboxylic acid derivative
Oxacycle
Monocarboxylic acid or derivatives
Acetal
Organoheterocyclic compound
Organic oxide
Alcohol
Hydrocarbon derivative
Organic oxygen compound
Carbonyl group
Primary 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	-1.5	ALOGPS
logP	-2.8	ChemAxon
logS	-1	ALOGPS
pKa (Strongest Acidic)	11.99	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	175.37 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	89.11 m³·mol⁻¹	ChemAxon
Polarizability	38.91 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	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

28509367

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

70684135

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Jensen, S. R., et al. (2007). Jensen, S. R., et al, J. Nat. Prod. 70, 29 (2007) . J. Nat. Prod..

Showing NP-Card for 7,8-dehydropenstemoside (NP0032618)

MOL for NP0032618 (7,8-dehydropenstemoside)

3D MOL for NP0032618 (7,8-dehydropenstemoside)

3D SDF for NP0032618 (7,8-dehydropenstemoside)

3D-SDF for NP0032618 (7,8-dehydropenstemoside)

PDB for NP0032618 (7,8-dehydropenstemoside)

3D PDB for NP0032618 (7,8-dehydropenstemoside)

SMILES for NP0032618 (7,8-dehydropenstemoside)

INCHI for NP0032618 (7,8-dehydropenstemoside)

Structure for NP0032618 (7,8-dehydropenstemoside)

3D Structure for NP0032618 (7,8-dehydropenstemoside)