NP-MRD: Showing NP-Card for (2r,3s,4s,5r,6s)-5-{[(2s,3r,4r)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-2-(hydroxymethyl)-6-(3,4,5-trimethoxyphenoxy)oxane-3,4-diol (NP0328180)

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Record Information

Version

1.0

Created at

2022-09-12 11:25:17 UTC

Updated at

2022-09-12 11:25:17 UTC

NP-MRD ID

NP0328180

Secondary Accession Numbers

None

Natural Product Identification

Common Name

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

Description

Khaephuoside 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)-5-{[(2s,3r,4r)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-2-(hydroxymethyl)-6-(3,4,5-trimethoxyphenoxy)oxane-3,4-diol is found in Albizia julibrissin. Based on a literature review very few articles have been published on Khaephuoside A.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309122213252D          

 33 35  0  0  1  0            999 V2000
    6.1166   -5.7288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6316   -5.0614    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9672   -4.3077    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4823   -3.6403    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8178   -2.8866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3329   -2.2192    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5124   -2.3054    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.1769   -3.0591    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3564   -3.1453    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0208   -3.8990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2004   -3.9852    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8715   -2.4779    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0510   -2.5641    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2070   -1.7242    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7221   -1.0568    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0275   -1.6380    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.3631   -0.8843    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8781   -0.2169    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0531   -0.2169    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7982    0.5678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4656    1.0527    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.9136    1.6658    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0177    1.6658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8247    1.4942    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1331    0.5678    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.9177    0.8227    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6383   -2.8004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1232   -3.4678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9437   -3.3816    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.4286   -4.0490    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7877   -4.2215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2726   -4.8889    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9371   -5.6426    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  7  6  1  6  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  6  0  0  0
 10 11  1  0  0  0  0
  9 12  1  0  0  0  0
 12 13  1  1  0  0  0
 12 14  1  0  0  0  0
 14 15  1  6  0  0  0
 14 16  1  0  0  0  0
  7 16  1  0  0  0  0
 16 17  1  1  0  0  0
 18 17  1  6  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  1  0  0  0
 21 23  1  6  0  0  0
 23 24  1  0  0  0  0
 21 25  1  0  0  0  0
 18 25  1  0  0  0  0
 25 26  1  1  0  0  0
  5 27  2  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
 28 31  2  0  0  0  0
  3 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
M  END

     RDKit          3D

 63 65  0  0  0  0  0  0  0  0999 V2000
   -4.5728    1.4470    0.2366 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7054    0.0472    0.3045 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6017   -0.7327   -0.0943 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4295   -0.1290   -0.5368 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3403   -0.8774   -0.9306 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1498   -0.3753   -1.3783 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1167    0.9877   -1.4940 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6063    1.2086   -2.7870 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7528    2.5361   -3.0800 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4926    2.6116   -4.4218 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7173    1.9750   -4.2304 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3750    3.3962   -2.0473 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6492    4.6005   -1.8592 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6863    2.7779   -0.7374 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0535    2.9242   -0.4196 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3084    1.3298   -0.5870 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9857    1.0248    0.7241 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8445    0.0772    1.2095 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2068   -1.0975    1.6549 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3364   -1.7701    2.1796 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8841   -0.7438    3.1335 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2507   -0.8991    3.3457 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0950   -0.8505    4.4162 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5178    0.1328    5.2780 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5564    0.5624    2.4618 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.7086    1.2491    2.1036 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4410   -2.2784   -0.8749 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5886   -2.9017   -0.4412 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6438   -4.2760   -0.4029 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6151   -5.1351   -0.7745 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6386   -2.0974   -0.0625 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7868   -2.7315    0.3718 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7754   -3.0534   -0.5850 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7208    1.8162    0.8653 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2856    1.7489   -0.8128 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4668    1.9884    0.5416 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3837    0.9643   -0.5683 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6791    1.6740   -1.2236 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2620    2.9783   -3.3128 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6010    3.6654   -4.7542 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9021    1.9990   -5.1289 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4821    2.5994   -4.2784 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3501    3.7664   -2.4906 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6626    4.8580   -0.8861 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1592    3.3598    0.0651 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2341    3.8200   -0.0660 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1793    0.7102   -0.8807 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6161   -0.2654    0.5009 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0463   -1.9040    1.3403 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0531   -2.7143    2.6747 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6771   -0.9723    2.4566 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1985   -1.8728    4.8346 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0246   -0.6499    4.1352 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2618   -0.2208    5.8443 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9207    1.2232    3.0810 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2586    0.7677    1.4541 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5726   -2.8465   -1.1897 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6823   -4.7739   -0.2542 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8180   -6.1314   -0.3180 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4002   -5.1865   -1.8439 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8583   -2.2487   -1.3686 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7817   -3.1080   -0.1018 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5715   -3.9839   -1.1339 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
  8  9  1  0
  9 10  1  0
 10 11  1  0
  9 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
 14 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  1
 21 23  1  0
 23 24  1  0
 21 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
 16  7  1  0
 25 18  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  6
 10 40  1  0
 10 41  1  0
 11 42  1  0
 12 43  1  6
 13 44  1  0
 14 45  1  1
 15 46  1  0
 16 47  1  6
 18 48  1  6
 20 49  1  0
 20 50  1  0
 22 51  1  0
 23 52  1  0
 23 53  1  0
 24 54  1  0
 25 55  1  1
 26 56  1  0
 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


  Mrv1652309122213252D          

 33 35  0  0  1  0            999 V2000
    6.1166   -5.7288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6316   -5.0614    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9672   -4.3077    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4823   -3.6403    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8178   -2.8866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3329   -2.2192    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5124   -2.3054    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.1769   -3.0591    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3564   -3.1453    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0208   -3.8990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2004   -3.9852    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8715   -2.4779    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0510   -2.5641    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2070   -1.7242    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7221   -1.0568    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0275   -1.6380    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.3631   -0.8843    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8781   -0.2169    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0531   -0.2169    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7982    0.5678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4656    1.0527    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.9136    1.6658    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0177    1.6658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8247    1.4942    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1331    0.5678    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.9177    0.8227    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6383   -2.8004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1232   -3.4678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9437   -3.3816    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.4286   -4.0490    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7877   -4.2215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2726   -4.8889    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9371   -5.6426    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  7  6  1  6  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  6  0  0  0
 10 11  1  0  0  0  0
  9 12  1  0  0  0  0
 12 13  1  1  0  0  0
 12 14  1  0  0  0  0
 14 15  1  6  0  0  0
 14 16  1  0  0  0  0
  7 16  1  0  0  0  0
 16 17  1  1  0  0  0
 18 17  1  6  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  1  0  0  0
 21 23  1  6  0  0  0
 23 24  1  0  0  0  0
 21 25  1  0  0  0  0
 18 25  1  0  0  0  0
 25 26  1  1  0  0  0
  5 27  2  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
 28 31  2  0  0  0  0
  3 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0328180

> <DATABASE_NAME>
NP-MRD

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

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

> <INCHI_KEY>
RTNAFZDXHULVPS-HDLUHPEBSA-N

> <FORMULA>
C20H30O13

> <MOLECULAR_WEIGHT>
478.447

> <EXACT_MASS>
478.168641026

> <JCHEM_ACCEPTOR_COUNT>
13

> <JCHEM_ATOM_COUNT>
63

> <JCHEM_AVERAGE_POLARIZABILITY>
46.52389620566604

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <JCHEM_LOGP>
-2.3479004560000005

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.652098411875446

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.807562252769637

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9810925693395296

> <JCHEM_POLAR_SURFACE_AREA>
185.98999999999998

> <JCHEM_REFRACTIVITY>
106.24309999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

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

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 12-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-SEP-22         0                                  
HETATM    1  C   UNK     0      11.418 -10.694   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      10.512  -9.448   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      11.139  -8.041   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      10.234  -6.795   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      10.860  -5.388   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       9.955  -4.142   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       8.423  -4.303   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       7.797  -5.710   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       6.265  -5.871   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.639  -7.278   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       4.107  -7.439   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       5.360  -4.625   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       3.829  -4.786   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       5.986  -3.219   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       5.081  -1.973   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       7.518  -3.058   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       8.144  -1.651   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       7.239  -0.405   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       5.699  -0.405   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       5.223   1.060   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       6.469   1.965   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       5.439   3.109   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       7.500   3.109   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       9.006   2.789   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       7.715   1.060   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       9.180   1.536   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      12.392  -5.227   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      13.297  -6.473   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      14.828  -6.312   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      15.733  -7.558   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      12.670  -7.880   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      13.576  -9.126   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0      12.949 -10.533   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   31                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   27                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   16                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   12                                                  
CONECT   10    9   11                                                       
CONECT   11   10                                                            
CONECT   12    9   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14    7   17                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   25                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22   23   25                                             
CONECT   22   21                                                            
CONECT   23   21   24                                                       
CONECT   24   23                                                            
CONECT   25   21   18   26                                                  
CONECT   26   25                                                            
CONECT   27    5   28                                                       
CONECT   28   27   29   31                                                  
CONECT   29   28   30                                                       
CONECT   30   29                                                            
CONECT   31   28    3   32                                                  
CONECT   32   31   33                                                       
CONECT   33   32                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   70    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₀H₃₀O₁₃

Average Mass

478.4470 Da

Monoisotopic Mass

478.16864 Da

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

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

InChI Key

RTNAFZDXHULVPS-HDLUHPEBSA-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
Albizia julibrissin	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
Acetal
Oxacycle
Organoheterocyclic compound
Ether
Hydrocarbon derivative
Primary alcohol
Alcohol
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic 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	-2.3	ChemAxon
pKa (Strongest Acidic)	11.81	ChemAxon
pKa (Strongest Basic)	-3	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	46.52 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

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00037371

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

15747353

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)-5-{[(2s,3r,4r)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-2-(hydroxymethyl)-6-(3,4,5-trimethoxyphenoxy)oxane-3,4-diol (NP0328180)

MOL for NP0328180 ((2r,3s,4s,5r,6s)-5-{[(2s,3r,4r)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-2-(hydroxymethyl)-6-(3,4,5-trimethoxyphenoxy)oxane-3,4-diol)

3D MOL for NP0328180 ((2r,3s,4s,5r,6s)-5-{[(2s,3r,4r)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-2-(hydroxymethyl)-6-(3,4,5-trimethoxyphenoxy)oxane-3,4-diol)

3D SDF for NP0328180 ((2r,3s,4s,5r,6s)-5-{[(2s,3r,4r)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-2-(hydroxymethyl)-6-(3,4,5-trimethoxyphenoxy)oxane-3,4-diol)

3D-SDF for NP0328180 ((2r,3s,4s,5r,6s)-5-{[(2s,3r,4r)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-2-(hydroxymethyl)-6-(3,4,5-trimethoxyphenoxy)oxane-3,4-diol)

PDB for NP0328180 ((2r,3s,4s,5r,6s)-5-{[(2s,3r,4r)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-2-(hydroxymethyl)-6-(3,4,5-trimethoxyphenoxy)oxane-3,4-diol)

3D PDB for NP0328180 ((2r,3s,4s,5r,6s)-5-{[(2s,3r,4r)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-2-(hydroxymethyl)-6-(3,4,5-trimethoxyphenoxy)oxane-3,4-diol)

SMILES for NP0328180 ((2r,3s,4s,5r,6s)-5-{[(2s,3r,4r)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-2-(hydroxymethyl)-6-(3,4,5-trimethoxyphenoxy)oxane-3,4-diol)

INCHI for NP0328180 ((2r,3s,4s,5r,6s)-5-{[(2s,3r,4r)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-2-(hydroxymethyl)-6-(3,4,5-trimethoxyphenoxy)oxane-3,4-diol)

Structure for NP0328180 ((2r,3s,4s,5r,6s)-5-{[(2s,3r,4r)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-2-(hydroxymethyl)-6-(3,4,5-trimethoxyphenoxy)oxane-3,4-diol)

3D Structure for NP0328180 ((2r,3s,4s,5r,6s)-5-{[(2s,3r,4r)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-2-(hydroxymethyl)-6-(3,4,5-trimethoxyphenoxy)oxane-3,4-diol)