NP-MRD: Showing NP-Card for shanzhiside (NP0032825)

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Record Information

Version

2.0

Created at

2021-06-19 23:32:15 UTC

Updated at

2021-06-30 00:02:15 UTC

NP-MRD ID

NP0032825

Secondary Accession Numbers

None

Natural Product Identification

Common Name

shanzhiside

Provided By

JEOL Database JEOL Logo

Description

(1S,4aS,5R,7S,7aS)-5,7-dihydroxy-7-methyl-1-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1H,4aH,5H,6H,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. shanzhiside is found in Barleria lupulina , Castilleja indivisa, Castilleja integra, Castilleja tenuiflora, Gardenia jasminoides , Genipa americana and Phlomoides hamosa. shanzhiside was first documented in 2007 (Ono, M., et al.). Based on a literature review very few articles have been published on (1S,4aS,5R,7S,7aS)-5,7-dihydroxy-7-methyl-1-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1H,4aH,5H,6H,7H,7aH-cyclopenta[c]pyran-4-carboxylic acid.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306202101323D          

 51 53  0  0  0  0            999 V2000
    1.0502   -1.6237   -2.3530 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7964   -2.5682   -1.1865 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0183   -3.2868   -0.9564 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3219   -3.5781   -1.4845 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8731   -4.0010   -0.1171 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6520   -5.3913    0.0834 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1296   -3.1547    0.9342 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0014   -2.7682    2.0917 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3723   -3.8422    3.0321 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1830   -5.0298    2.8290 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9619   -3.4038    4.1533 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3951   -1.5009    2.2697 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1261   -0.4625    1.4195 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6793   -0.8335    0.1028 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1072    0.3174   -0.5216 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0961    1.2890   -0.8697 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.9081    0.8000   -1.9381 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9065    1.7505   -2.3363 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.8071    1.1145   -3.4042 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.9441    1.9207   -3.6913 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2406    3.0314   -2.8670 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.2180    4.0082   -3.2420 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3208    3.6109   -1.7917 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6227    4.7413   -2.3360 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3320    2.5526   -1.3099 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4456    3.1034   -0.2361 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3935   -1.9321    0.1571 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4315   -2.1757   -3.2201 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1449   -1.0978   -2.6686 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8180   -0.8860   -2.0954 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1755   -3.8762   -1.7158 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0341   -4.4351   -2.0665 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1272   -3.0927   -2.0494 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9571   -3.8369   -0.0934 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8407   -5.5903    1.0254 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7301   -3.7192    1.3232 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1384   -4.2165    4.6719 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9638   -1.1494    3.1233 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5496   -1.1760   -0.4720 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7132    1.5118    0.0105 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5401    1.9968   -1.4731 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2525    0.9417   -4.3331 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1629    0.1363   -3.0637 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6272    2.8469   -3.7670 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6499    2.8083   -3.7647 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7101    4.8388   -3.3641 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9101    4.0026   -0.9533 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0687    4.9561   -1.6763 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3762    2.3115   -2.1126 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9603    2.3539    0.1261 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2809   -1.5349    0.6702 H   0  0  0  0  0  0  0  0  0  0  0  0
  7  8  1  0  0  0  0
 27 14  1  0  0  0  0
 14 13  1  0  0  0  0
 13 12  1  0  0  0  0
 12  8  2  0  0  0  0
 27  7  1  0  0  0  0
 18 17  1  0  0  0  0
 17 16  1  0  0  0  0
 21 22  1  0  0  0  0
 23 24  1  0  0  0  0
  7  5  1  0  0  0  0
  5  4  1  0  0  0  0
  4  2  1  0  0  0  0
  2 27  1  0  0  0  0
 25 26  1  0  0  0  0
  7 36  1  1  0  0  0
 14 15  1  0  0  0  0
  8  9  1  0  0  0  0
  9 11  1  0  0  0  0
 19 20  1  0  0  0  0
  9 10  2  0  0  0  0
 16 25  1  0  0  0  0
  5  6  1  0  0  0  0
 25 23  1  0  0  0  0
 27 51  1  1  0  0  0
 23 21  1  0  0  0  0
  2  3  1  1  0  0  0
 21 18  1  0  0  0  0
  2  1  1  0  0  0  0
 18 19  1  0  0  0  0
 16 15  1  0  0  0  0
 16 40  1  1  0  0  0
 21 45  1  6  0  0  0
 22 46  1  0  0  0  0
 23 47  1  1  0  0  0
 24 48  1  0  0  0  0
 25 49  1  6  0  0  0
 26 50  1  0  0  0  0
 19 42  1  0  0  0  0
 19 43  1  0  0  0  0
 18 41  1  1  0  0  0
 20 44  1  0  0  0  0
 14 39  1  6  0  0  0
 12 38  1  0  0  0  0
  5 34  1  6  0  0  0
  4 32  1  0  0  0  0
  4 33  1  0  0  0  0
 11 37  1  0  0  0  0
  6 35  1  0  0  0  0
  3 31  1  0  0  0  0
  1 28  1  0  0  0  0
  1 29  1  0  0  0  0
  1 30  1  0  0  0  0
M  END

     RDKit          3D

 51 53  0  0  0  0  0  0  0  0999 V2000
    1.0502   -1.6237   -2.3530 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7964   -2.5682   -1.1865 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0183   -3.2868   -0.9564 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3219   -3.5781   -1.4845 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8731   -4.0010   -0.1171 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6520   -5.3913    0.0834 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1296   -3.1547    0.9342 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0014   -2.7682    2.0917 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3723   -3.8422    3.0321 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1830   -5.0298    2.8290 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9619   -3.4038    4.1533 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3951   -1.5009    2.2697 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1261   -0.4625    1.4195 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6793   -0.8335    0.1028 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1072    0.3174   -0.5216 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0961    1.2890   -0.8697 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.9081    0.8000   -1.9381 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9065    1.7505   -2.3363 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.8071    1.1145   -3.4042 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9441    1.9207   -3.6913 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2406    3.0314   -2.8670 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.2180    4.0082   -3.2420 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3208    3.6109   -1.7917 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6227    4.7413   -2.3360 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3320    2.5526   -1.3099 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4456    3.1034   -0.2361 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3935   -1.9321    0.1571 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4315   -2.1757   -3.2201 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1449   -1.0978   -2.6686 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8180   -0.8860   -2.0954 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1755   -3.8762   -1.7158 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0341   -4.4351   -2.0665 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1272   -3.0927   -2.0494 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9571   -3.8369   -0.0934 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8407   -5.5903    1.0254 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7301   -3.7192    1.3232 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1384   -4.2165    4.6719 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9638   -1.1494    3.1233 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5496   -1.1760   -0.4720 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7132    1.5118    0.0105 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5401    1.9968   -1.4731 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2525    0.9417   -4.3331 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1629    0.1363   -3.0637 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6272    2.8469   -3.7670 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6499    2.8083   -3.7647 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7101    4.8388   -3.3641 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9101    4.0026   -0.9533 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0687    4.9561   -1.6763 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3762    2.3115   -2.1126 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9603    2.3539    0.1261 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2809   -1.5349    0.6702 H   0  0  0  0  0  0  0  0  0  0  0  0
  7  8  1  0
 27 14  1  0
 14 13  1  0
 13 12  1  0
 12  8  2  0
 27  7  1  0
 18 17  1  0
 17 16  1  0
 21 22  1  0
 23 24  1  0
  7  5  1  0
  5  4  1  0
  4  2  1  0
  2 27  1  0
 25 26  1  0
  7 36  1  1
 14 15  1  0
  8  9  1  0
  9 11  1  0
 19 20  1  0
  9 10  2  0
 16 25  1  0
  5  6  1  0
 25 23  1  0
 27 51  1  1
 23 21  1  0
  2  3  1  1
 21 18  1  0
  2  1  1  0
 18 19  1  0
 16 15  1  0
 16 40  1  1
 21 45  1  6
 22 46  1  0
 23 47  1  1
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 19 42  1  0
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 12 38  1  0
  5 34  1  6
  4 32  1  0
  4 33  1  0
 11 37  1  0
  6 35  1  0
  3 31  1  0
  1 28  1  0
  1 29  1  0
  1 30  1  0
M  END


  Mrv1652306202101323D          

 51 53  0  0  0  0            999 V2000
    1.0502   -1.6237   -2.3530 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7964   -2.5682   -1.1865 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0183   -3.2868   -0.9564 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3219   -3.5781   -1.4845 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8731   -4.0010   -0.1171 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6520   -5.3913    0.0834 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1296   -3.1547    0.9342 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0014   -2.7682    2.0917 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3723   -3.8422    3.0321 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1830   -5.0298    2.8290 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9619   -3.4038    4.1533 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3951   -1.5009    2.2697 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1261   -0.4625    1.4195 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6793   -0.8335    0.1028 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1072    0.3174   -0.5216 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0961    1.2890   -0.8697 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.9081    0.8000   -1.9381 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9065    1.7505   -2.3363 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.8071    1.1145   -3.4042 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.9441    1.9207   -3.6913 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2406    3.0314   -2.8670 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.2180    4.0082   -3.2420 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3208    3.6109   -1.7917 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6227    4.7413   -2.3360 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3320    2.5526   -1.3099 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4456    3.1034   -0.2361 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3935   -1.9321    0.1571 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4315   -2.1757   -3.2201 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1449   -1.0978   -2.6686 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8180   -0.8860   -2.0954 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1755   -3.8762   -1.7158 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0341   -4.4351   -2.0665 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1272   -3.0927   -2.0494 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9571   -3.8369   -0.0934 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8407   -5.5903    1.0254 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7301   -3.7192    1.3232 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1384   -4.2165    4.6719 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9638   -1.1494    3.1233 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5496   -1.1760   -0.4720 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7132    1.5118    0.0105 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5401    1.9968   -1.4731 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2525    0.9417   -4.3331 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1629    0.1363   -3.0637 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6272    2.8469   -3.7670 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6499    2.8083   -3.7647 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7101    4.8388   -3.3641 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9101    4.0026   -0.9533 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0687    4.9561   -1.6763 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3762    2.3115   -2.1126 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9603    2.3539    0.1261 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2809   -1.5349    0.6702 H   0  0  0  0  0  0  0  0  0  0  0  0
  7  8  1  0  0  0  0
 27 14  1  0  0  0  0
 14 13  1  0  0  0  0
 13 12  1  0  0  0  0
 12  8  2  0  0  0  0
 27  7  1  0  0  0  0
 18 17  1  0  0  0  0
 17 16  1  0  0  0  0
 21 22  1  0  0  0  0
 23 24  1  0  0  0  0
  7  5  1  0  0  0  0
  5  4  1  0  0  0  0
  4  2  1  0  0  0  0
  2 27  1  0  0  0  0
 25 26  1  0  0  0  0
  7 36  1  1  0  0  0
 14 15  1  0  0  0  0
  8  9  1  0  0  0  0
  9 11  1  0  0  0  0
 19 20  1  0  0  0  0
  9 10  2  0  0  0  0
 16 25  1  0  0  0  0
  5  6  1  0  0  0  0
 25 23  1  0  0  0  0
 27 51  1  1  0  0  0
 23 21  1  0  0  0  0
  2  3  1  1  0  0  0
 21 18  1  0  0  0  0
  2  1  1  0  0  0  0
 18 19  1  0  0  0  0
 16 15  1  0  0  0  0
 16 40  1  1  0  0  0
 21 45  1  6  0  0  0
 22 46  1  0  0  0  0
 23 47  1  1  0  0  0
 24 48  1  0  0  0  0
 25 49  1  6  0  0  0
 26 50  1  0  0  0  0
 19 42  1  0  0  0  0
 19 43  1  0  0  0  0
 18 41  1  1  0  0  0
 20 44  1  0  0  0  0
 14 39  1  6  0  0  0
 12 38  1  0  0  0  0
  5 34  1  6  0  0  0
  4 32  1  0  0  0  0
  4 33  1  0  0  0  0
 11 37  1  0  0  0  0
  6 35  1  0  0  0  0
  3 31  1  0  0  0  0
  1 28  1  0  0  0  0
  1 29  1  0  0  0  0
  1 30  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0032825

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C16H24O11/c1-16(24)2-6(18)8-5(13(22)23)4-25-14(9(8)16)27-15-12(21)11(20)10(19)7(3-17)26-15/h4,6-12,14-15,17-21,24H,2-3H2,1H3,(H,22,23)/t6-,7-,8+,9-,10-,11+,12-,14+,15+,16+/m1/s1

> <INCHI_KEY>
YSIFYNVXJOGADM-KDYWOABDSA-N

> <FORMULA>
C16H24O11

> <MOLECULAR_WEIGHT>
392.357

> <EXACT_MASS>
392.131861593

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_ATOM_COUNT>
51

> <JCHEM_AVERAGE_POLARIZABILITY>
37.161522601415825

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
-2.20

> <JCHEM_LOGP>
-3.421248663666667

> <ALOGPS_LOGS>
-0.60

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
12.203763350254254

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.1814352857802195

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9103179781686617

> <JCHEM_POLAR_SURFACE_AREA>
186.37

> <JCHEM_REFRACTIVITY>
84.06000000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
9.96e+01 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 51 53  0  0  0  0  0  0  0  0999 V2000
    1.0502   -1.6237   -2.3530 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7964   -2.5682   -1.1865 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0183   -3.2868   -0.9564 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3219   -3.5781   -1.4845 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8731   -4.0010   -0.1171 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6520   -5.3913    0.0834 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1296   -3.1547    0.9342 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0014   -2.7682    2.0917 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3723   -3.8422    3.0321 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1830   -5.0298    2.8290 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9619   -3.4038    4.1533 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3951   -1.5009    2.2697 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1261   -0.4625    1.4195 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6793   -0.8335    0.1028 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1072    0.3174   -0.5216 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0961    1.2890   -0.8697 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.9081    0.8000   -1.9381 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9065    1.7505   -2.3363 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.8071    1.1145   -3.4042 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9441    1.9207   -3.6913 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2406    3.0314   -2.8670 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.2180    4.0082   -3.2420 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3208    3.6109   -1.7917 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6227    4.7413   -2.3360 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3320    2.5526   -1.3099 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4456    3.1034   -0.2361 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3935   -1.9321    0.1571 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4315   -2.1757   -3.2201 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1449   -1.0978   -2.6686 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8180   -0.8860   -2.0954 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1755   -3.8762   -1.7158 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0341   -4.4351   -2.0665 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1272   -3.0927   -2.0494 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9571   -3.8369   -0.0934 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8407   -5.5903    1.0254 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7301   -3.7192    1.3232 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1384   -4.2165    4.6719 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9638   -1.1494    3.1233 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5496   -1.1760   -0.4720 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7132    1.5118    0.0105 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5401    1.9968   -1.4731 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2525    0.9417   -4.3331 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1629    0.1363   -3.0637 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6272    2.8469   -3.7670 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6499    2.8083   -3.7647 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7101    4.8388   -3.3641 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9101    4.0026   -0.9533 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0687    4.9561   -1.6763 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3762    2.3115   -2.1126 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9603    2.3539    0.1261 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2809   -1.5349    0.6702 H   0  0  0  0  0  0  0  0  0  0  0  0
  7  8  1  0
 27 14  1  0
 14 13  1  0
 13 12  1  0
 12  8  2  0
 27  7  1  0
 18 17  1  0
 17 16  1  0
 21 22  1  0
 23 24  1  0
  7  5  1  0
  5  4  1  0
  4  2  1  0
  2 27  1  0
 25 26  1  0
  7 36  1  1
 14 15  1  0
  8  9  1  0
  9 11  1  0
 19 20  1  0
  9 10  2  0
 16 25  1  0
  5  6  1  0
 25 23  1  0
 27 51  1  1
 23 21  1  0
  2  3  1  1
 21 18  1  0
  2  1  1  0
 18 19  1  0
 16 15  1  0
 16 40  1  1
 21 45  1  6
 22 46  1  0
 23 47  1  1
 24 48  1  0
 25 49  1  6
 26 50  1  0
 19 42  1  0
 19 43  1  0
 18 41  1  1
 20 44  1  0
 14 39  1  6
 12 38  1  0
  5 34  1  6
  4 32  1  0
  4 33  1  0
 11 37  1  0
  6 35  1  0
  3 31  1  0
  1 28  1  0
  1 29  1  0
  1 30  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       1.050  -1.624  -2.353  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.796  -2.568  -1.187  0.00  0.00           C+0
HETATM    3  O   UNK     0       2.018  -3.287  -0.956  0.00  0.00           O+0
HETATM    4  C   UNK     0      -0.322  -3.578  -1.484  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.873  -4.001  -0.117  0.00  0.00           C+0
HETATM    6  O   UNK     0      -0.652  -5.391   0.083  0.00  0.00           O+0
HETATM    7  C   UNK     0      -0.130  -3.155   0.934  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.001  -2.768   2.092  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.372  -3.842   3.032  0.00  0.00           C+0
HETATM   10  O   UNK     0      -1.183  -5.030   2.829  0.00  0.00           O+0
HETATM   11  O   UNK     0      -1.962  -3.404   4.153  0.00  0.00           O+0
HETATM   12  C   UNK     0      -1.395  -1.501   2.270  0.00  0.00           C+0
HETATM   13  O   UNK     0      -1.126  -0.463   1.420  0.00  0.00           O+0
HETATM   14  C   UNK     0      -0.679  -0.834   0.103  0.00  0.00           C+0
HETATM   15  O   UNK     0      -0.107   0.317  -0.522  0.00  0.00           O+0
HETATM   16  C   UNK     0      -1.096   1.289  -0.870  0.00  0.00           C+0
HETATM   17  O   UNK     0      -1.908   0.800  -1.938  0.00  0.00           O+0
HETATM   18  C   UNK     0      -2.906   1.751  -2.336  0.00  0.00           C+0
HETATM   19  C   UNK     0      -3.807   1.115  -3.404  0.00  0.00           C+0
HETATM   20  O   UNK     0      -4.944   1.921  -3.691  0.00  0.00           O+0
HETATM   21  C   UNK     0      -2.241   3.031  -2.867  0.00  0.00           C+0
HETATM   22  O   UNK     0      -3.218   4.008  -3.242  0.00  0.00           O+0
HETATM   23  C   UNK     0      -1.321   3.611  -1.792  0.00  0.00           C+0
HETATM   24  O   UNK     0      -0.623   4.741  -2.336  0.00  0.00           O+0
HETATM   25  C   UNK     0      -0.332   2.553  -1.310  0.00  0.00           C+0
HETATM   26  O   UNK     0       0.446   3.103  -0.236  0.00  0.00           O+0
HETATM   27  C   UNK     0       0.394  -1.932   0.157  0.00  0.00           C+0
HETATM   28  H   UNK     0       1.432  -2.176  -3.220  0.00  0.00           H+0
HETATM   29  H   UNK     0       0.145  -1.098  -2.669  0.00  0.00           H+0
HETATM   30  H   UNK     0       1.818  -0.886  -2.095  0.00  0.00           H+0
HETATM   31  H   UNK     0       2.176  -3.876  -1.716  0.00  0.00           H+0
HETATM   32  H   UNK     0       0.034  -4.435  -2.067  0.00  0.00           H+0
HETATM   33  H   UNK     0      -1.127  -3.093  -2.049  0.00  0.00           H+0
HETATM   34  H   UNK     0      -1.957  -3.837  -0.093  0.00  0.00           H+0
HETATM   35  H   UNK     0      -0.841  -5.590   1.025  0.00  0.00           H+0
HETATM   36  H   UNK     0       0.730  -3.719   1.323  0.00  0.00           H+0
HETATM   37  H   UNK     0      -2.138  -4.216   4.672  0.00  0.00           H+0
HETATM   38  H   UNK     0      -1.964  -1.149   3.123  0.00  0.00           H+0
HETATM   39  H   UNK     0      -1.550  -1.176  -0.472  0.00  0.00           H+0
HETATM   40  H   UNK     0      -1.713   1.512   0.011  0.00  0.00           H+0
HETATM   41  H   UNK     0      -3.540   1.997  -1.473  0.00  0.00           H+0
HETATM   42  H   UNK     0      -3.252   0.942  -4.333  0.00  0.00           H+0
HETATM   43  H   UNK     0      -4.163   0.136  -3.064  0.00  0.00           H+0
HETATM   44  H   UNK     0      -4.627   2.847  -3.767  0.00  0.00           H+0
HETATM   45  H   UNK     0      -1.650   2.808  -3.765  0.00  0.00           H+0
HETATM   46  H   UNK     0      -2.710   4.839  -3.364  0.00  0.00           H+0
HETATM   47  H   UNK     0      -1.910   4.003  -0.953  0.00  0.00           H+0
HETATM   48  H   UNK     0       0.069   4.956  -1.676  0.00  0.00           H+0
HETATM   49  H   UNK     0       0.376   2.312  -2.113  0.00  0.00           H+0
HETATM   50  H   UNK     0       0.960   2.354   0.126  0.00  0.00           H+0
HETATM   51  H   UNK     0       1.281  -1.535   0.670  0.00  0.00           H+0
CONECT    1    2   28   29   30                                             
CONECT    2    4   27    3    1                                             
CONECT    3    2   31                                                       
CONECT    4    5    2   32   33                                             
CONECT    5    7    4    6   34                                             
CONECT    6    5   35                                                       
CONECT    7    8   27    5   36                                             
CONECT    8    7   12    9                                                  
CONECT    9    8   11   10                                                  
CONECT   10    9                                                            
CONECT   11    9   37                                                       
CONECT   12   13    8   38                                                  
CONECT   13   14   12                                                       
CONECT   14   27   13   15   39                                             
CONECT   15   14   16                                                       
CONECT   16   17   25   15   40                                             
CONECT   17   18   16                                                       
CONECT   18   17   21   19   41                                             
CONECT   19   20   18   42   43                                             
CONECT   20   19   44                                                       
CONECT   21   22   23   18   45                                             
CONECT   22   21   46                                                       
CONECT   23   24   25   21   47                                             
CONECT   24   23   48                                                       
CONECT   25   26   16   23   49                                             
CONECT   26   25   50                                                       
CONECT   27   14    7    2   51                                             
CONECT   28    1                                                            
CONECT   29    1                                                            
CONECT   30    1                                                            
CONECT   31    3                                                            
CONECT   32    4                                                            
CONECT   33    4                                                            
CONECT   34    5                                                            
CONECT   35    6                                                            
CONECT   36    7                                                            
CONECT   37   11                                                            
CONECT   38   12                                                            
CONECT   39   14                                                            
CONECT   40   16                                                            
CONECT   41   18                                                            
CONECT   42   19                                                            
CONECT   43   19                                                            
CONECT   44   20                                                            
CONECT   45   21                                                            
CONECT   46   22                                                            
CONECT   47   23                                                            
CONECT   48   24                                                            
CONECT   49   25                                                            
CONECT   50   26                                                            
CONECT   51   27                                                            
MASTER        0    0    0    0    0    0    0    0   51    0  106    0
END

RDKit          3D

51 53  0  0  0  0  0  0  0  0999 V2000
    1.0502   -1.6237   -2.3530 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7964   -2.5682   -1.1865 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0183   -3.2868   -0.9564 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3219   -3.5781   -1.4845 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8731   -4.0010   -0.1171 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6520   -5.3913    0.0834 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1296   -3.1547    0.9342 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0014   -2.7682    2.0917 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3723   -3.8422    3.0321 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1830   -5.0298    2.8290 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9619   -3.4038    4.1533 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3951   -1.5009    2.2697 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1261   -0.4625    1.4195 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6793   -0.8335    0.1028 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1072    0.3174   -0.5216 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0961    1.2890   -0.8697 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.9081    0.8000   -1.9381 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9065    1.7505   -2.3363 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.8071    1.1145   -3.4042 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9441    1.9207   -3.6913 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2406    3.0314   -2.8670 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.2180    4.0082   -3.2420 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3208    3.6109   -1.7917 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6227    4.7413   -2.3360 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3320    2.5526   -1.3099 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4456    3.1034   -0.2361 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3935   -1.9321    0.1571 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4315   -2.1757   -3.2201 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1449   -1.0978   -2.6686 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8180   -0.8860   -2.0954 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1755   -3.8762   -1.7158 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0341   -4.4351   -2.0665 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1272   -3.0927   -2.0494 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9571   -3.8369   -0.0934 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8407   -5.5903    1.0254 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7301   -3.7192    1.3232 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1384   -4.2165    4.6719 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9638   -1.1494    3.1233 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5496   -1.1760   -0.4720 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7132    1.5118    0.0105 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5401    1.9968   -1.4731 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2525    0.9417   -4.3331 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1629    0.1363   -3.0637 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6272    2.8469   -3.7670 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6499    2.8083   -3.7647 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7101    4.8388   -3.3641 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9101    4.0026   -0.9533 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0687    4.9561   -1.6763 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3762    2.3115   -2.1126 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9603    2.3539    0.1261 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2809   -1.5349    0.6702 H   0  0  0  0  0  0  0  0  0  0  0  0
  7  8  1  0
 27 14  1  0
 14 13  1  0
 13 12  1  0
 12  8  2  0
 27  7  1  0
 18 17  1  0
 17 16  1  0
 21 22  1  0
 23 24  1  0
  7  5  1  0
  5  4  1  0
  4  2  1  0
  2 27  1  0
 25 26  1  0
  7 36  1  1
 14 15  1  0
  8  9  1  0
  9 11  1  0
 19 20  1  0
  9 10  2  0
 16 25  1  0
  5  6  1  0
 25 23  1  0
 27 51  1  1
 23 21  1  0
  2  3  1  1
 21 18  1  0
  2  1  1  0
 18 19  1  0
 16 15  1  0
 16 40  1  1
 21 45  1  6
 22 46  1  0
 23 47  1  1
 24 48  1  0
 25 49  1  6
 26 50  1  0
 19 42  1  0
 19 43  1  0
 18 41  1  1
 20 44  1  0
 14 39  1  6
 12 38  1  0
  5 34  1  6
  4 32  1  0
  4 33  1  0
 11 37  1  0
  6 35  1  0
  3 31  1  0
  1 28  1  0
  1 29  1  0
  1 30  1  0
M  END

View in JSmol

Synonyms

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

Chemical Formula

C₁₆H₂₄O₁₁

Average Mass

392.3570 Da

Monoisotopic Mass

392.13186 Da

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C16H24O11/c1-16(24)2-6(18)8-5(13(22)23)4-25-14(9(8)16)27-15-12(21)11(20)10(19)7(3-17)26-15/h4,6-12,14-15,17-21,24H,2-3H2,1H3,(H,22,23)/t6-,7-,8+,9-,10-,11+,12-,14+,15+,16+/m1/s1

InChI Key

YSIFYNVXJOGADM-KDYWOABDSA-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
Barleria lupulina	Plant	KNApSAcK
Castilleja indivisa	LOTUS Database	35616633
Castilleja integra	Plant	KNApSAcK
Castilleja tenuiflora	LOTUS Database	35616633
Gardenia jasminoides	Plant	KNApSAcK
Genipa americana	JEOL database	Ono, M., et al, Chem. Pharm. Bull. 55, 632 (2007)
Phlomoides hamosa	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
Hexose monosaccharide
Glycosyl compound
Iridoid-skeleton
O-glycosyl compound
Bicyclic monoterpenoid
Monoterpenoid
Monosaccharide
Oxane
Cyclic alcohol
Vinylogous ester
Tertiary alcohol
Secondary alcohol
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Oxacycle
Acetal
Carboxylic acid
Carboxylic acid derivative
Polyol
Organooxygen compound
Alcohol
Hydrocarbon derivative
Organic oxide
Carbonyl group
Organic oxygen compound
Primary alcohol
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

terpene glycoside (CHEBI:80902 )

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	-2.2	ALOGPS
logP	-3.4	ChemAxon
logS	-0.6	ALOGPS
pKa (Strongest Acidic)	4.18	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	186.37 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	84.06 m³·mol⁻¹	ChemAxon
Polarizability	37.16 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	No	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

10122984

KEGG Compound ID

C17066

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Ono, M., et al. (2007). Ono, M., et al, Chem. Pharm. Bull. 55, 632 (2007) . Chem. Pharm. Bull..

Showing NP-Card for shanzhiside (NP0032825)

MOL for NP0032825 (shanzhiside)

3D MOL for NP0032825 (shanzhiside)

3D SDF for NP0032825 (shanzhiside)

3D-SDF for NP0032825 (shanzhiside)

PDB for NP0032825 (shanzhiside)

3D PDB for NP0032825 (shanzhiside)

SMILES for NP0032825 (shanzhiside)

INCHI for NP0032825 (shanzhiside)

Structure for NP0032825 (shanzhiside)

3D Structure for NP0032825 (shanzhiside)