NP-MRD: Showing NP-Card for methyl (4r,5s,6r)-5-ethenyl-4-[(1s)-1h,2h,3h,4h,9h-pyrido[3,4-b]indol-1-ylmethyl]-6-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5,6-dihydro-4h-pyran-3-carboxylate (NP0272481)

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Record Information

Version

2.0

Created at

2022-09-08 19:07:20 UTC

Updated at

2022-09-08 19:07:20 UTC

NP-MRD ID

NP0272481

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl (4r,5s,6r)-5-ethenyl-4-[(1s)-1h,2h,3h,4h,9h-pyrido[3,4-b]indol-1-ylmethyl]-6-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5,6-dihydro-4h-pyran-3-carboxylate

Description

(2R)-2alpha-(beta-D-Glucopyranosyloxy)-3beta-vinyl-4beta-[[(1S)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-1alpha-yl]methyl]-3,4-dihydro-2H-pyran-5-carboxylic acid methyl ester belongs to the class of organic compounds known as terpene glycosides. These are prenol lipids containing a carbohydrate moiety glycosidically bound to a terpene backbone. methyl (4r,5s,6r)-5-ethenyl-4-[(1s)-1h,2h,3h,4h,9h-pyrido[3,4-b]indol-1-ylmethyl]-6-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5,6-dihydro-4h-pyran-3-carboxylate is found in Uncaria rhynchophylla. Based on a literature review very few articles have been published on (2R)-2alpha-(beta-D-Glucopyranosyloxy)-3beta-vinyl-4beta-[[(1S)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-1alpha-yl]methyl]-3,4-dihydro-2H-pyran-5-carboxylic acid methyl ester.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309082221072D          

 38 42  0  0  1  0            999 V2000
    5.3194    0.6825    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7674    0.0694    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0223   -0.7152    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.8293   -0.8867    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.3813   -0.2736    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1883   -0.4451    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.7403    0.1680    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5473   -0.0036    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    9.0993    0.6095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9063    0.4380    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.8022   -0.7882    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    9.6092   -0.9597    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.2502   -1.4013    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.5051   -2.1859    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4432   -1.2298    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.8912   -1.8429    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0842   -1.6713    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5322   -2.2844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7252   -2.1129    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1732   -2.7260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3662   -2.5545    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4281   -3.5106    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8761   -4.1237    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4703   -1.3283    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.6633   -1.1567    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4084   -0.3721    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.9604    0.2410    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7054    1.0256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8985    1.1971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3464    0.5840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6014   -0.2006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9339   -0.6855    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2665   -0.2006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4595   -0.3721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0925    0.2410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1624    1.0256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9694    1.1971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5214    0.5840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  3  2  1  6  0  0  0
  3  4  1  0  0  0  0
  4  5  1  1  0  0  0
  6  5  1  6  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  6  0  0  0
  9 10  1  0  0  0  0
  8 11  1  0  0  0  0
 11 12  1  1  0  0  0
 11 13  1  0  0  0  0
 13 14  1  6  0  0  0
 13 15  1  0  0  0  0
  6 15  1  0  0  0  0
 15 16  1  1  0  0  0
  4 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  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
 22 23  1  0  0  0  0
 19 24  1  0  0  0  0
  3 24  1  0  0  0  0
 24 25  1  6  0  0  0
 26 25  1  1  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
 26 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  2  0  0  0  0
 34 35  1  0  0  0  0
 35 36  2  0  0  0  0
 36 37  1  0  0  0  0
 37 38  2  0  0  0  0
 30 38  1  0  0  0  0
 33 38  1  0  0  0  0
M  END

     RDKit          3D

 72 76  0  0  0  0  0  0  0  0999 V2000
    2.1258   -3.1509   -1.3792 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.9891    0.8105    0.2812 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3574    1.0482    0.2753 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5678    2.1291    1.1192 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8375    2.6243    1.1533 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.7622    4.0894    0.7023 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9993    4.6939    0.6867 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8371    1.9015    0.3102 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.1182    0.6429    0.8586 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3362    1.7568   -1.0950 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.5544    2.9228   -1.8350 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8628    1.4586   -1.0803 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.6595    0.3334   -1.9134 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7564   -0.2975    1.9158 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.4395   -1.7746   -1.0065 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.6837   -1.9801   -1.9637 N   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.6599    0.0824   -0.6571 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2601   -0.0670   -0.7581 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7515    1.1302   -0.7731 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7430    2.0706   -0.6857 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7516    3.4422   -0.6599 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9422    4.1652   -0.5625 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1401    3.5000   -0.4899 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1325    2.1368   -0.5153 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9409    1.4089   -0.6130 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1391   -2.5787   -2.3015 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5815   -4.1216   -1.4083 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5691   -3.2324    0.6027 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0293   -0.8476   -1.2941 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5434   -0.9529    1.0670 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8573    0.1689    0.6795 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2279    2.6423    2.2198 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1305    4.6419    1.4423 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3042    4.1064   -0.2979 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3362    4.8691    1.5952 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8226    2.4629    0.3196 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0523    0.3797    0.6393 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8847    0.9218   -1.5981 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5456    3.0079   -1.9148 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2941    2.3071   -1.5082 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.1155   -1.1715   -1.9186 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3023   -2.8466   -1.3526 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2641   -1.9492    0.1085 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2724   -2.7887   -2.4306 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -5.6845   -2.1916   -2.4561 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -7.0640    1.5958   -0.4593 H   0  0  0  0  0  0  0  0  0  0  0  0
 23 22  1  0
 22 20  1  0
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 17  4  1  0
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  5  6  1  0
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  8  9  1  0
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 11 12  1  0
 11 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
  4  3  1  0
  3  2  1  0
  2  1  2  3
  3 24  1  0
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 31 26  1  0
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 38 30  1  0
 23 56  1  0
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 23 58  1  0
 18 55  1  0
  4 43  1  1
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 10 48  1  0
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  3 42  1  6
  2 41  1  0
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  1 40  1  0
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 29 66  1  0
 29 67  1  0
 32 68  1  0
 34 69  1  0
 35 70  1  0
 36 71  1  0
 37 72  1  0
M  END


  Mrv1652309082221072D          

 38 42  0  0  1  0            999 V2000
    5.3194    0.6825    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7674    0.0694    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0223   -0.7152    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.8293   -0.8867    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.3813   -0.2736    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1883   -0.4451    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.7403    0.1680    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5473   -0.0036    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    9.0993    0.6095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9063    0.4380    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.8022   -0.7882    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    9.6092   -0.9597    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.2502   -1.4013    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.5051   -2.1859    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4432   -1.2298    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.8912   -1.8429    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    3.3662   -2.5545    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4281   -3.5106    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    4.4703   -1.3283    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.6633   -1.1567    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4084   -0.3721    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.9604    0.2410    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7054    1.0256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8985    1.1971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3464    0.5840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6014   -0.2006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9339   -0.6855    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2665   -0.2006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4595   -0.3721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0925    0.2410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1624    1.0256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9694    1.1971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5214    0.5840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  3  2  1  6  0  0  0
  3  4  1  0  0  0  0
  4  5  1  1  0  0  0
  6  5  1  6  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  6  0  0  0
  9 10  1  0  0  0  0
  8 11  1  0  0  0  0
 11 12  1  1  0  0  0
 11 13  1  0  0  0  0
 13 14  1  6  0  0  0
 13 15  1  0  0  0  0
  6 15  1  0  0  0  0
 15 16  1  1  0  0  0
  4 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  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
 22 23  1  0  0  0  0
 19 24  1  0  0  0  0
  3 24  1  0  0  0  0
 24 25  1  6  0  0  0
 26 25  1  1  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
 26 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  2  0  0  0  0
 34 35  1  0  0  0  0
 35 36  2  0  0  0  0
 36 37  1  0  0  0  0
 37 38  2  0  0  0  0
 30 38  1  0  0  0  0
 33 38  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0272481

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)C1=CO[C@H](O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)[C@@H](C=C)[C@H]1C[C@@H]1NCCC2=C1NC1=CC=CC=C21

> <INCHI_IDENTIFIER>
InChI=1S/C27H34N2O9/c1-3-13-16(10-19-21-15(8-9-28-19)14-6-4-5-7-18(14)29-21)17(25(34)35-2)12-36-26(13)38-27-24(33)23(32)22(31)20(11-30)37-27/h3-7,12-13,16,19-20,22-24,26-33H,1,8-11H2,2H3/t13-,16+,19-,20+,22+,23-,24+,26+,27-/m0/s1

> <INCHI_KEY>
XBAMJZTXGWPTRM-ZHCRJAQZSA-N

> <FORMULA>
C27H34N2O9

> <MOLECULAR_WEIGHT>
530.574

> <EXACT_MASS>
530.226430683

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
72

> <JCHEM_AVERAGE_POLARIZABILITY>
54.16392588393933

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
methyl (2R,3S,4R)-3-ethenyl-4-{[(1S)-1H,2H,3H,4H,9H-pyrido[3,4-b]indol-1-yl]methyl}-2-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,4-dihydro-2H-pyran-5-carboxylate

> <JCHEM_LOGP>
0.5208186083333349

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
13.19852044430446

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.20751973384191

> <JCHEM_PKA_STRONGEST_BASIC>
9.342001657830965

> <JCHEM_POLAR_SURFACE_AREA>
162.73

> <JCHEM_REFRACTIVITY>
134.69779999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
methyl (4R,5S,6R)-5-ethenyl-4-[(1S)-1H,2H,3H,4H,9H-pyrido[3,4-b]indol-1-ylmethyl]-6-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5,6-dihydro-4H-pyran-3-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 08-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   08-SEP-22         0                                  
HETATM    1  C   UNK     0       9.930   1.274   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.899   0.130   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       9.375  -1.335   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      10.881  -1.655   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      11.912  -0.511   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      13.418  -0.831   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      14.449   0.314   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      15.955  -0.007   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      16.985   1.138   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      18.492   0.818   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      16.431  -1.471   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      17.937  -1.791   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      15.400  -2.616   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      15.876  -4.080   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      13.894  -2.296   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      12.864  -3.440   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0      11.357  -3.120   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      10.327  -4.264   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       8.820  -3.944   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       7.790  -5.089   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       6.284  -4.768   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       8.266  -6.553   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       7.235  -7.698   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       8.344  -2.479   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       6.838  -2.159   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       6.362  -0.695   0.000  0.00  0.00           C+0
HETATM   27  N   UNK     0       7.393   0.450   0.000  0.00  0.00           N+0
HETATM   28  C   UNK     0       6.917   1.914   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       5.410   2.235   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       4.380   1.090   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       4.856  -0.374   0.000  0.00  0.00           C+0
HETATM   32  N   UNK     0       3.610  -1.280   0.000  0.00  0.00           N+0
HETATM   33  C   UNK     0       2.364  -0.374   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       0.858  -0.695   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      -0.173   0.450   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       0.303   1.914   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       1.810   2.235   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       2.840   1.090   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   24                                                  
CONECT    4    3    5   17                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7   15                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   11                                                  
CONECT    9    8   10                                                       
CONECT   10    9                                                            
CONECT   11    8   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13    6   16                                                  
CONECT   16   15                                                            
CONECT   17    4   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   24                                                  
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23                                                       
CONECT   23   22                                                            
CONECT   24   19    3   25                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27   31                                                  
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   31   38                                                  
CONECT   31   30   26   32                                                  
CONECT   32   31   33                                                       
CONECT   33   32   34   38                                                  
CONECT   34   33   35                                                       
CONECT   35   34   36                                                       
CONECT   36   35   37                                                       
CONECT   37   36   38                                                       
CONECT   38   37   30   33                                                  
MASTER        0    0    0    0    0    0    0    0   38    0   84    0
END

View in JSmol

Synonyms

Value	Source
(2R)-2a-(b-D-Glucopyranosyloxy)-3b-vinyl-4b-[[(1S)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-1a-yl]methyl]-3,4-dihydro-2H-pyran-5-carboxylate methyl ester	Generator
(2R)-2a-(b-D-Glucopyranosyloxy)-3b-vinyl-4b-[[(1S)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-1a-yl]methyl]-3,4-dihydro-2H-pyran-5-carboxylic acid methyl ester	Generator
(2R)-2alpha-(beta-D-Glucopyranosyloxy)-3beta-vinyl-4beta-[[(1S)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-1alpha-yl]methyl]-3,4-dihydro-2H-pyran-5-carboxylate methyl ester	Generator
(2R)-2Α-(β-D-glucopyranosyloxy)-3β-vinyl-4β-[[(1S)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-1α-yl]methyl]-3,4-dihydro-2H-pyran-5-carboxylate methyl ester	Generator
(2R)-2Α-(β-D-glucopyranosyloxy)-3β-vinyl-4β-[[(1S)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-1α-yl]methyl]-3,4-dihydro-2H-pyran-5-carboxylic acid methyl ester	Generator

Chemical Formula

C₂₇H₃₄N₂O₉

Average Mass

530.5740 Da

Monoisotopic Mass

530.22643 Da

IUPAC Name

methyl (2R,3S,4R)-3-ethenyl-4-{[(1S)-1H,2H,3H,4H,9H-pyrido[3,4-b]indol-1-yl]methyl}-2-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,4-dihydro-2H-pyran-5-carboxylate

Traditional Name

methyl (4R,5S,6R)-5-ethenyl-4-[(1S)-1H,2H,3H,4H,9H-pyrido[3,4-b]indol-1-ylmethyl]-6-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5,6-dihydro-4H-pyran-3-carboxylate

CAS Registry Number

Not Available

SMILES

COC(=O)C1=CO[C@H](O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)[C@@H](C=C)[C@H]1C[C@@H]1NCCC2=C1NC1=CC=CC=C21

InChI Identifier

InChI=1S/C27H34N2O9/c1-3-13-16(10-19-21-15(8-9-28-19)14-6-4-5-7-18(14)29-21)17(25(34)35-2)12-36-26(13)38-27-24(33)23(32)22(31)20(11-30)37-27/h3-7,12-13,16,19-20,22-24,26-33H,1,8-11H2,2H3/t13-,16+,19-,20+,22+,23-,24+,26+,27-/m0/s1

InChI Key

XBAMJZTXGWPTRM-ZHCRJAQZSA-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
Uncaria rhynchophylla	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as terpene glycosides. These are prenol lipids containing a carbohydrate moiety glycosidically bound to a terpene backbone.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene glycosides

Direct Parent

Terpene glycosides

Alternative Parents

Substituents

Terpene glycoside
Harman
Beta-carboline
Pyridoindole
Glycosyl compound
Secoiridoid-skeleton
O-glycosyl compound
Aromatic monoterpenoid
3-alkylindole
Monoterpenoid
Indole
Indole or derivatives
Alkaloid or derivatives
Sugar acid
Aralkylamine
Oxane
Monosaccharide
Benzenoid
Heteroaromatic compound
Vinylogous ester
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Pyrrole
Methyl ester
Secondary alcohol
Amino acid or derivatives
Carboxylic acid ester
Polyol
Secondary amine
Carboxylic acid derivative
Organoheterocyclic compound
Azacycle
Monocarboxylic acid or derivatives
Oxacycle
Acetal
Secondary aliphatic amine
Organic nitrogen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Alcohol
Carbonyl group
Organic oxygen compound
Primary alcohol
Organonitrogen compound
Organooxygen compound
Amine
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
logP	0.52	ChemAxon
pKa (Strongest Acidic)	12.21	ChemAxon
pKa (Strongest Basic)	9.34	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	162.73 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	134.7 m³·mol⁻¹	ChemAxon
Polarizability	54.16 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

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

101552461

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for methyl (4r,5s,6r)-5-ethenyl-4-[(1s)-1h,2h,3h,4h,9h-pyrido[3,4-b]indol-1-ylmethyl]-6-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5,6-dihydro-4h-pyran-3-carboxylate (NP0272481)

MOL for NP0272481 (methyl (4r,5s,6r)-5-ethenyl-4-[(1s)-1h,2h,3h,4h,9h-pyrido[3,4-b]indol-1-ylmethyl]-6-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5,6-dihydro-4h-pyran-3-carboxylate)

3D MOL for NP0272481 (methyl (4r,5s,6r)-5-ethenyl-4-[(1s)-1h,2h,3h,4h,9h-pyrido[3,4-b]indol-1-ylmethyl]-6-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5,6-dihydro-4h-pyran-3-carboxylate)

3D SDF for NP0272481 (methyl (4r,5s,6r)-5-ethenyl-4-[(1s)-1h,2h,3h,4h,9h-pyrido[3,4-b]indol-1-ylmethyl]-6-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5,6-dihydro-4h-pyran-3-carboxylate)

3D-SDF for NP0272481 (methyl (4r,5s,6r)-5-ethenyl-4-[(1s)-1h,2h,3h,4h,9h-pyrido[3,4-b]indol-1-ylmethyl]-6-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5,6-dihydro-4h-pyran-3-carboxylate)

PDB for NP0272481 (methyl (4r,5s,6r)-5-ethenyl-4-[(1s)-1h,2h,3h,4h,9h-pyrido[3,4-b]indol-1-ylmethyl]-6-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5,6-dihydro-4h-pyran-3-carboxylate)

3D PDB for NP0272481 (methyl (4r,5s,6r)-5-ethenyl-4-[(1s)-1h,2h,3h,4h,9h-pyrido[3,4-b]indol-1-ylmethyl]-6-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5,6-dihydro-4h-pyran-3-carboxylate)

SMILES for NP0272481 (methyl (4r,5s,6r)-5-ethenyl-4-[(1s)-1h,2h,3h,4h,9h-pyrido[3,4-b]indol-1-ylmethyl]-6-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5,6-dihydro-4h-pyran-3-carboxylate)

INCHI for NP0272481 (methyl (4r,5s,6r)-5-ethenyl-4-[(1s)-1h,2h,3h,4h,9h-pyrido[3,4-b]indol-1-ylmethyl]-6-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5,6-dihydro-4h-pyran-3-carboxylate)

Structure for NP0272481 (methyl (4r,5s,6r)-5-ethenyl-4-[(1s)-1h,2h,3h,4h,9h-pyrido[3,4-b]indol-1-ylmethyl]-6-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5,6-dihydro-4h-pyran-3-carboxylate)

3D Structure for NP0272481 (methyl (4r,5s,6r)-5-ethenyl-4-[(1s)-1h,2h,3h,4h,9h-pyrido[3,4-b]indol-1-ylmethyl]-6-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5,6-dihydro-4h-pyran-3-carboxylate)