NP-MRD: Showing NP-Card for (2r,3s,4s,5r,6s)-2-({[(2r,3r,4r)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}methyl)-6-(3,4,5-trimethoxyphenoxy)oxane-3,4,5-triol (NP0229060)

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Record Information

Version

2.0

Created at

2022-09-06 08:58:00 UTC

Updated at

2022-09-06 08:58:00 UTC

NP-MRD ID

NP0229060

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2r,3s,4s,5r,6s)-2-({[(2r,3r,4r)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}methyl)-6-(3,4,5-trimethoxyphenoxy)oxane-3,4,5-triol

Description

Kelampayoside A belongs to the class of organic compounds known as phenolic glycosides. These are organic compounds containing a phenolic structure attached to a glycosyl moiety. Some examples of phenolic structures include lignans, and flavonoids. Among the sugar units found in natural glycosides are D-glucose, L-Fructose, and L rhamnose. (2r,3s,4s,5r,6s)-2-({[(2r,3r,4r)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}methyl)-6-(3,4,5-trimethoxyphenoxy)oxane-3,4,5-triol is found in Acer nikoense, Acer saccharum, Alibertia edulis, Betula ermanii, Betula maximowicziana, Bretschneidera sinensis, Carallia brachiata, Cinnamomum aromaticum, Dracaena cambodiana, Morinda coreia, Nauclea orientalis, Neolamarckia cadamba, Smilax glabra and Strychnos axillaris. Kelampayoside A is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309272007332D          

 33 35  0  0  0  0            999 V2000
 2503.7624 2502.2269    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2504.4764 2501.8136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2503.7624 2500.5779    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2504.4764 2500.9890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2502.3323 2503.0514    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2503.0463 2503.4627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2500.9041 2500.5779    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2499.4782 2498.1044    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2498.7642 2498.5156    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2498.2567 2496.6580    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2496.2375 2496.9198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2495.5234 2497.3330    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2497.1643 2496.5372    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2502.3343 2499.7534    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2502.3343 2498.1044    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2500.9041 2497.2799    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2502.3329 2502.2268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2501.6185 2501.8143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2501.6185 2500.9892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2502.3329 2500.5767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2503.0474 2500.9892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2503.0474 2501.8143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2500.9056 2499.7533    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 2500.1911 2499.3408    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2500.1911 2498.5157    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 2500.9056 2498.1033    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 2501.6201 2498.5157    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 2501.6201 2499.3408    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 2497.3788 2498.5988    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2496.7113 2498.1138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2496.9663 2497.3292    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 2497.7913 2497.3292    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 2498.0462 2498.1138    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  3  4  1  0  0  0  0
  5  6  1  0  0  0  0
  8  9  1  0  0  0  0
 11 12  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 17  1  0  0  0  0
 17  5  1  0  0  0  0
 19  7  1  0  0  0  0
 21  3  1  0  0  0  0
  1 22  1  0  0  0  0
 23 28  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 29 30  1  0  0  0  0
 29 33  1  0  0  0  0
 28 14  1  6  0  0  0
 27 15  1  1  0  0  0
 26 16  1  6  0  0  0
 25  8  1  1  0  0  0
 23  7  1  1  0  0  0
 31 13  1  6  0  0  0
 31 11  1  0  0  0  0
 32 10  1  6  0  0  0
 33  9  1  1  0  0  0
M  END

     RDKit          3D

 63 65  0  0  0  0  0  0  0  0999 V2000
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   -4.5723    0.0798    1.2047 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3584   -0.3555    0.6842 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6002    0.4715   -0.0882 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.3079   -1.9182    0.2423 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7159   -1.7538   -0.2638 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4141   -0.7399    0.3381 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6901   -0.6848   -0.2101 C   0  0  2  0  0  0  0  0  0  0  0  0
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    5.7229    1.3993    0.3081 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.0304    1.7457   -0.0408 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9324    2.5944    0.7503 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8677    3.5330   -0.2719 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0094    0.6722   -0.7812 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.9067    0.4663   -1.8464 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7389   -3.2051   -0.2735 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1087   -3.8074    0.6544 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1045   -3.0768   -1.6355 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9432   -3.5406   -2.6351 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3812   -1.6710   -1.9050 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4187   -1.6020   -2.7983 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0754    1.7452   -0.3336 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2915    2.1885    0.1851 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7611    3.4696   -0.0666 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9586    4.3122   -0.8708 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0649    1.3463    0.9724 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2432    1.8130    1.4598 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5049    1.7541    0.8914 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9377   -2.6827    1.3539 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5006   -2.5678    3.0430 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8416   -2.0390    2.6532 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0143   -1.3442    0.8888 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2223   -1.8398    0.0587 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4089   -2.0545    1.3614 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6501   -1.5655   -1.3595 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2205   -2.7536   -0.1415 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7811   -1.4611   -0.9702 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7028    0.4636    1.9813 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9144    0.5739    2.1125 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4640    0.9348   -0.3929 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4081    3.0695    1.6340 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8956    2.2547    0.9539 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2390    4.4197    0.0082 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1190    1.2052   -1.1633 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5368   -0.1993   -2.4814 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6056   -3.9119   -0.3964 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2271   -3.5342    1.5506 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7984   -3.7295   -1.6346 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7592   -3.1000   -3.5133 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4802   -1.0993   -2.3077 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4373   -0.7097   -3.2259 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4832    2.4362   -0.9552 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3845    5.3395   -0.7697 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9546    4.3648   -0.3646 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -8.2798    1.8194    1.6960 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6785    0.9005    0.2107 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
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  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
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 17 18  1  0
 15 19  1  0
 19 20  1  0
  9 21  1  0
 21 22  1  0
 21 23  1  0
 23 24  1  0
 23 25  1  0
 25 26  1  0
  5 27  2  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
 28 31  2  0
 31 32  1  0
 32 33  1  0
 31  3  1  0
 25  7  1  0
 19 12  1  0
  1 34  1  0
  1 35  1  0
  1 36  1  0
  4 37  1  0
  7 38  1  1
  9 39  1  1
 10 40  1  0
 10 41  1  0
 12 42  1  6
 14 43  1  0
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 16 45  1  0
 17 46  1  0
 17 47  1  0
 18 48  1  0
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 25 55  1  6
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 27 57  1  0
 30 58  1  0
 30 59  1  0
 30 60  1  0
 33 61  1  0
 33 62  1  0
 33 63  1  0
M  END


  Mrv1652309272007332D          

 33 35  0  0  0  0            999 V2000
 2503.7624 2502.2269    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2504.4764 2501.8136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2503.7624 2500.5779    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2504.4764 2500.9890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2502.3323 2503.0514    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2503.0463 2503.4627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2500.9041 2500.5779    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2499.4782 2498.1044    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2498.7642 2498.5156    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2498.2567 2496.6580    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2496.2375 2496.9198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2495.5234 2497.3330    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2497.1643 2496.5372    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2502.3343 2499.7534    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2502.3343 2498.1044    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2500.9041 2497.2799    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2502.3329 2502.2268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2501.6185 2501.8143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2501.6185 2500.9892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2502.3329 2500.5767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2503.0474 2500.9892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2503.0474 2501.8143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2500.9056 2499.7533    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 2500.1911 2499.3408    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2500.1911 2498.5157    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 2500.9056 2498.1033    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 2501.6201 2498.5157    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 2501.6201 2499.3408    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 2497.3788 2498.5988    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2496.7113 2498.1138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2496.9663 2497.3292    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 2497.7913 2497.3292    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 2498.0462 2498.1138    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  3  4  1  0  0  0  0
  5  6  1  0  0  0  0
  8  9  1  0  0  0  0
 11 12  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
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 22 17  1  0  0  0  0
 17  5  1  0  0  0  0
 19  7  1  0  0  0  0
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  1 22  1  0  0  0  0
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 25 26  1  0  0  0  0
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 27 28  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
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 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 29 30  1  0  0  0  0
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 28 14  1  6  0  0  0
 27 15  1  1  0  0  0
 26 16  1  6  0  0  0
 25  8  1  1  0  0  0
 23  7  1  1  0  0  0
 31 13  1  6  0  0  0
 31 11  1  0  0  0  0
 32 10  1  6  0  0  0
 33  9  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0229060

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(O[C@@H]2O[C@H](CO[C@@H]3OC[C@](O)(CO)[C@H]3O)[C@@H](O)[C@H](O)[C@H]2O)=CC(OC)=C1OC

> <INCHI_IDENTIFIER>
InChI=1S/C20H30O13/c1-27-10-4-9(5-11(28-2)16(10)29-3)32-18-15(24)14(23)13(22)12(33-18)6-30-19-17(25)20(26,7-21)8-31-19/h4-5,12-15,17-19,21-26H,6-8H2,1-3H3/t12-,13-,14+,15-,17+,18-,19-,20-/m1/s1

> <INCHI_KEY>
CKGKQISENBKOCA-FHXQZXMCSA-N

> <FORMULA>
C20H30O13

> <MOLECULAR_WEIGHT>
478.447

> <EXACT_MASS>
478.168641026

> <JCHEM_ACCEPTOR_COUNT>
13

> <JCHEM_ATOM_COUNT>
63

> <JCHEM_AVERAGE_POLARIZABILITY>
46.612319676765516

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R,3S,4S,5R,6S)-2-({[(2R,3R,4R)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}methyl)-6-(3,4,5-trimethoxyphenoxy)oxane-3,4,5-triol

> <ALOGPS_LOGP>
-0.99

> <JCHEM_LOGP>
-2.3479004560000005

> <ALOGPS_LOGS>
-1.64

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.311723442969438

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.701739641197952

> <JCHEM_PKA_STRONGEST_BASIC>
-3.1423790163389214

> <JCHEM_POLAR_SURFACE_AREA>
185.98999999999998

> <JCHEM_REFRACTIVITY>
106.24309999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.09e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2R,3S,4S,5R,6S)-2-({[(2R,3R,4R)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}methyl)-6-(3,4,5-trimethoxyphenoxy)oxane-3,4,5-triol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 27-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-SEP-20         0                                  
HETATM    1  O   UNK     0    4673.6904670.824   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0    4675.0234670.052   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0    4673.6904667.745   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0    4675.0234668.513   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0    4671.0204672.363   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0    4672.3534673.130   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0    4668.3544667.745   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0    4665.6934663.128   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0    4664.3604663.896   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0    4663.4134660.428   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0    4659.6434660.917   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0    4658.3104661.688   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0    4661.3734660.203   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0    4671.0244666.206   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0    4671.0244663.128   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0    4668.3544661.589   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0    4671.0214670.823   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0    4669.6884670.053   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0    4669.6884668.513   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0    4671.0214667.743   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0    4672.3554668.513   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0    4672.3554670.053   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0    4668.3574666.206   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0    4667.0234665.436   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0    4667.0234663.896   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0    4668.3574663.126   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0    4669.6914663.896   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0    4669.6914665.436   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0    4661.7744664.051   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0    4660.5284663.146   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0    4661.0044661.681   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0    4662.5444661.681   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0    4663.0204663.146   0.000  0.00  0.00           C+0
CONECT    1    2   22                                                       
CONECT    2    1                                                            
CONECT    3    4   21                                                       
CONECT    4    3                                                            
CONECT    5    6   17                                                       
CONECT    6    5                                                            
CONECT    7   19   23                                                       
CONECT    8    9   25                                                       
CONECT    9    8   33                                                       
CONECT   10   32                                                            
CONECT   11   12   31                                                       
CONECT   12   11                                                            
CONECT   13   31                                                            
CONECT   14   28                                                            
CONECT   15   27                                                            
CONECT   16   26                                                            
CONECT   17   18   22    5                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20    7                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22    3                                                  
CONECT   22   21   17    1                                                  
CONECT   23   28   24    7                                                  
CONECT   24   23   25                                                       
CONECT   25   26   24    8                                                  
CONECT   26   25   27   16                                                  
CONECT   27   26   28   15                                                  
CONECT   28   23   27   14                                                  
CONECT   29   30   33                                                       
CONECT   30   31   29                                                       
CONECT   31   30   32   13   11                                             
CONECT   32   31   33   10                                                  
CONECT   33   32   29    9                                                  
MASTER        0    0    0    0    0    0    0    0   33    0   70    0
END

View in JSmol

Synonyms

Value	Source
Kelampayoside a	MeSH
3,4,5-Trimethoxyphenyl 6-O-D-apio-beta-D-furanosyl-beta-D-glucopyranoside	PhytoBank
3,4,5-Trimethoxyphenyl 6-O-D-apio-β-D-furanosyl-β-D-glucopyranoside	PhytoBank
3,4,5-Trimethoxyphenol 1-O-beta-D-apiofuranosyl-(1->6)-beta-D-glucopyranoside	PhytoBank
3,4,5-Trimethoxyphenol 1-O-β-D-apiofuranosyl-(1→6)-β-D-glucopyranoside	PhytoBank
3,4,5-Trimethoxyphenol 1-O-beta-D-apiofuranosyl-(1→6)-beta-D-glucopyranoside	PhytoBank

Chemical Formula

C₂₀H₃₀O₁₃

Average Mass

478.4470 Da

Monoisotopic Mass

478.16864 Da

IUPAC Name

(2R,3S,4S,5R,6S)-2-({[(2R,3R,4R)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}methyl)-6-(3,4,5-trimethoxyphenoxy)oxane-3,4,5-triol

Traditional Name

(2R,3S,4S,5R,6S)-2-({[(2R,3R,4R)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}methyl)-6-(3,4,5-trimethoxyphenoxy)oxane-3,4,5-triol

CAS Registry Number

Not Available

SMILES

COC1=CC(O[C@@H]2O[C@H](CO[C@@H]3OC[C@](O)(CO)[C@H]3O)[C@@H](O)[C@H](O)[C@H]2O)=CC(OC)=C1OC

InChI Identifier

InChI=1S/C20H30O13/c1-27-10-4-9(5-11(28-2)16(10)29-3)32-18-15(24)14(23)13(22)12(33-18)6-30-19-17(25)20(26,7-21)8-31-19/h4-5,12-15,17-19,21-26H,6-8H2,1-3H3/t12-,13-,14+,15-,17+,18-,19-,20-/m1/s1

InChI Key

CKGKQISENBKOCA-FHXQZXMCSA-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
Acer nikoense	LOTUS Database	35616633
Acer saccharum	LOTUS Database	35616633
Alibertia edulis	LOTUS Database	35616633
Betula ermanii	LOTUS Database	35616633
Betula maximowicziana	LOTUS Database	35616633
Bretschneidera sinensis	LOTUS Database	35616633
Carallia brachiata	LOTUS Database	35616633
Cinnamomum aromaticum	LOTUS Database	35616633
Dracaena cambodiana	LOTUS Database	35616633
Morinda coreia	LOTUS Database	35616633
Nauclea orientalis	LOTUS Database	35616633
Neolamarckia cadamba	LOTUS Database	35616633
Smilax glabra	LOTUS Database	35616633
Strychnos axillaris	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenolic glycosides. These are organic compounds containing a phenolic structure attached to a glycosyl moiety. Some examples of phenolic structures include lignans, and flavonoids. Among the sugar units found in natural glycosides are D-glucose, L-Fructose, and L rhamnose.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Phenolic glycosides

Alternative Parents

Substituents

Phenolic glycoside
Disaccharide
O-glycosyl compound
Phenoxy compound
Anisole
Methoxybenzene
Phenol ether
Alkyl aryl ether
Monocyclic benzene moiety
Benzenoid
Oxane
Tetrahydrofuran
Tertiary alcohol
Secondary alcohol
Polyol
Ether
Organoheterocyclic compound
Acetal
Oxacycle
Hydrocarbon derivative
Alcohol
Primary alcohol
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

glycoside (CHEBI:68963 )

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	-0.99	ALOGPS
logP	-2.3	ChemAxon
logS	-1.6	ALOGPS
pKa (Strongest Acidic)	11.7	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	13	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	185.99 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	106.24 m³·mol⁻¹	ChemAxon
Polarizability	46.61 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	Yes	ChemAxon

External Links

HMDB ID

HMDB0038714

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

8728028

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10552637

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2r,3s,4s,5r,6s)-2-({[(2r,3r,4r)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}methyl)-6-(3,4,5-trimethoxyphenoxy)oxane-3,4,5-triol (NP0229060)

MOL for NP0229060 ((2r,3s,4s,5r,6s)-2-({[(2r,3r,4r)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}methyl)-6-(3,4,5-trimethoxyphenoxy)oxane-3,4,5-triol)

3D MOL for NP0229060 ((2r,3s,4s,5r,6s)-2-({[(2r,3r,4r)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}methyl)-6-(3,4,5-trimethoxyphenoxy)oxane-3,4,5-triol)

3D SDF for NP0229060 ((2r,3s,4s,5r,6s)-2-({[(2r,3r,4r)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}methyl)-6-(3,4,5-trimethoxyphenoxy)oxane-3,4,5-triol)

3D-SDF for NP0229060 ((2r,3s,4s,5r,6s)-2-({[(2r,3r,4r)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}methyl)-6-(3,4,5-trimethoxyphenoxy)oxane-3,4,5-triol)

PDB for NP0229060 ((2r,3s,4s,5r,6s)-2-({[(2r,3r,4r)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}methyl)-6-(3,4,5-trimethoxyphenoxy)oxane-3,4,5-triol)

3D PDB for NP0229060 ((2r,3s,4s,5r,6s)-2-({[(2r,3r,4r)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}methyl)-6-(3,4,5-trimethoxyphenoxy)oxane-3,4,5-triol)

SMILES for NP0229060 ((2r,3s,4s,5r,6s)-2-({[(2r,3r,4r)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}methyl)-6-(3,4,5-trimethoxyphenoxy)oxane-3,4,5-triol)

INCHI for NP0229060 ((2r,3s,4s,5r,6s)-2-({[(2r,3r,4r)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}methyl)-6-(3,4,5-trimethoxyphenoxy)oxane-3,4,5-triol)

Structure for NP0229060 ((2r,3s,4s,5r,6s)-2-({[(2r,3r,4r)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}methyl)-6-(3,4,5-trimethoxyphenoxy)oxane-3,4,5-triol)

3D Structure for NP0229060 ((2r,3s,4s,5r,6s)-2-({[(2r,3r,4r)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}methyl)-6-(3,4,5-trimethoxyphenoxy)oxane-3,4,5-triol)