NP-MRD: Showing NP-Card for Orientin-7-o-rhamnoglucoside (NP0045021)

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Record Information

Version

2.0

Created at

2022-03-10 18:52:52 UTC

Updated at

2022-03-10 22:21:58 UTC

NP-MRD ID

NP0045021

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Orientin-7-o-rhamnoglucoside

Description

Orientin-7-O-rhamnoglucoside is a derivative of the flavone known as orientin. It belongs to the class of organic compounds known as flavonoid 7-O-glycosides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to carbohydrate moiety at the C7-position. Thus, Orientin-7-O-rhamnoglucoside consists of a luteolin flavonoid backbone with a glucose moiety attached at the 8-C position of luteiolin and a rhamnose group attached the 7-O position. Orientin can have a number of sugar moieties attached to it, including glucose (leading to Orientin-7-O-glucoside) and rhamnose (leading to Orientin-7-O-rhamnoglucoside). Orientin-7-O-rhamnoglucoside is a very water soluble flavonoid C-glycoside found in calcium tree and black bamboo. Orientin has been detected, but not quantified in, several different foods including spelts, triticales, red rices, hard wheats, and flaxseeds. Orientin is also found in the passionflower, the A‚àö√üa‚àö‚â† palm, buckwheat sprouts, and in millets. Orientin exhibits antioxidant, antiaging, antiviral, antibacterial, anti-inflammation, vasodilatation and cardioprotective, radiation protective, neuroprotective, antidepressant-like, antiadipogenesis, and antinociceptive activities (https://Doi.Org/10.1155/2016/4104595). Orientin-7-O-rhamnoglucoside is one of several dozen flavonoid glycosides that are known in cannabis plants. It was first isolated and identified as a cannabis constituent in 1973 (PMID: 6991645 ).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652303192001313D          

 53 58  0  0  0  0            999 V2000
   -8.0418   -0.7701   -0.4371 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8547    0.1914   -0.4854 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.7952   -0.4548    0.0395 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5153   -0.0717   -0.3556 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.6797   -0.1152    0.7453 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7431   -1.1482    0.7651 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.4326   -2.1548    1.7940 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.5643   -3.1529    2.1326 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7007   -1.2734    2.9711 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.6591   -2.0930    4.1337 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9420   -0.0319    3.1387 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.5295    0.0142    4.6287 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5990   -1.0129    4.8081 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7833    0.1987    2.4517 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5144   -0.7973    1.4730 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3497   -0.6135    0.7635 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3639    0.5506    0.5345 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1626    1.7921    0.7014 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5469    2.9803    0.4948 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0470    4.1726    0.6683 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8712    2.8765    0.1008 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6891    3.9655   -0.0948 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2393    5.1350    0.0373 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0051    3.7447   -0.4379 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5362    2.4899   -0.5903 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7080    1.4885   -0.4003 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4274    1.6226   -0.0704 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6982    0.4483    0.1256 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2636   -0.8848   -0.0863 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4742   -1.9834    0.1716 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3779   -3.0816    0.1021 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0263   -4.2386    0.9530 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8323   -4.8648    0.7026 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6034   -3.4029   -1.3638 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.9054   -3.8553   -1.6146 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4366   -2.1162   -2.1886 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.1451   -2.2608   -3.3537 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1349   -1.0023   -1.2902 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.3955   -1.5260   -1.1417 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9376    2.2940   -0.9133 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7459    3.2484   -1.4598 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1325    3.0498   -1.6449 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8975    4.0668   -2.2041 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.7447    1.8687   -1.2791 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1017    1.6714   -1.4551 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9210    0.9188   -0.7325 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5830    1.1049   -0.5499 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4121    1.2535   -1.0164 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.2200    1.2085   -1.7868 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5447    1.6588   -1.8885 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.0948    1.8575   -3.1932 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6857    0.6845   -1.8820 C   0  0  2  0  0  0  0  0  0  0  0  0
   -7.9024    1.3317   -2.2173 O   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  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 11 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 28 29  1  0  0  0  0
 29 30  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
 31 34  1  0  0  0  0
 34 35  1  0  0  0  0
 34 36  1  0  0  0  0
 36 37  1  0  0  0  0
 36 38  1  0  0  0  0
 38 39  1  0  0  0  0
 25 40  1  0  0  0  0
 40 41  2  0  0  0  0
 41 42  1  0  0  0  0
 42 43  1  0  0  0  0
 42 44  2  0  0  0  0
 44 45  1  0  0  0  0
 44 46  1  0  0  0  0
 46 47  2  0  0  0  0
  4 48  1  0  0  0  0
 48 49  1  0  0  0  0
 48 50  1  0  0  0  0
 50 51  1  0  0  0  0
 50 52  1  0  0  0  0
 52 53  1  0  0  0  0
 52  2  1  0  0  0  0
 15  6  1  0  0  0  0
 28 17  1  0  0  0  0
 38 29  1  0  0  0  0
 47 40  1  0  0  0  0
 27 21  1  0  0  0  0
M  END

     RDKit          3D

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   -3.7394   -2.6994   -0.2627 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.2715   -2.9173   -1.5244 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8190   -3.8098    0.0990 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.8831   -4.0658   -0.8719 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1538   -3.4465    1.3978 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3005   -4.6122    1.9183 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0850   -5.7353    1.9244 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4855   -2.3077    1.3849 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6536   -1.4379    0.2753 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0952   -0.2694    0.5776 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2489    0.6983    0.7403 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7232    1.9213    1.2613 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0306    3.0153    1.4982 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4860    4.2013    2.0191 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3904    2.9328    1.1995 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1521    4.0528    1.4235 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7236    5.1287    1.8966 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4785    3.9902    1.1069 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.6684   -0.6541   -0.0523 C   0  0  1  0  0  0  0  0  0  0  0  0
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    4.3240   -1.3227   -2.1361 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0570   -1.0125   -1.0008 O   0  0  0  0  0  0  0  0  0  0  0  0
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    1.6110   -3.4825   -0.9591 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3024   -2.4609    0.4266 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7904   -3.5036    1.2461 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8027   -1.1180    0.8702 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1704   -1.3336    2.1355 O   0  0  0  0  0  0  0  0  0  0  0  0
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   10.0891    3.4988   -0.4493 H   0  0  0  0  0  0  0  0  0  0  0  0
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 31 29  2  0
 29 30  1  0
 29 28  1  0
 28 27  2  0
  4 48  1  0
 48 49  1  0
 48 50  1  0
 50 51  1  0
 50 52  1  0
 52 53  1  0
 52  2  1  0
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 36 17  1  0
 46 37  1  0
 27 26  1  0
 35 21  1  0
  1 54  1  0
  1 55  1  0
  1 56  1  0
  2 57  1  1
  4 58  1  6
  6 59  1  6
  7 60  1  1
  8 61  1  0
  9 62  1  1
 10 63  1  0
 11 64  1  1
 12 65  1  0
 12 66  1  0
 13 67  1  0
 15 68  1  6
 18 69  1  0
 20 70  1  0
 24 71  1  0
 37 77  1  6
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 40 79  1  0
 40 80  1  0
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 46 86  1  1
 47 87  1  0
 33 76  1  0
 32 75  1  0
 30 74  1  0
 28 73  1  0
 27 72  1  0
 48 88  1  1
 49 89  1  0
 50 90  1  1
 51 91  1  0
 52 92  1  6
 53 93  1  0
M  END


  Mrv1652303192001313D          

 53 58  0  0  0  0            999 V2000
   -8.0418   -0.7701   -0.4371 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8547    0.1914   -0.4854 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.7952   -0.4548    0.0395 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5153   -0.0717   -0.3556 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.6797   -0.1152    0.7453 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7431   -1.1482    0.7651 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.4326   -2.1548    1.7940 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.5643   -3.1529    2.1326 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7007   -1.2734    2.9711 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.6591   -2.0930    4.1337 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9420   -0.0319    3.1387 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.5295    0.0142    4.6287 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5990   -1.0129    4.8081 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7833    0.1987    2.4517 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5144   -0.7973    1.4730 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3497   -0.6135    0.7635 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3639    0.5506    0.5345 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1626    1.7921    0.7014 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5469    2.9803    0.4948 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0470    4.1726    0.6683 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8712    2.8765    0.1008 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6891    3.9655   -0.0948 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2393    5.1350    0.0373 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0051    3.7447   -0.4379 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5362    2.4899   -0.5903 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7080    1.4885   -0.4003 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4274    1.6226   -0.0704 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6982    0.4483    0.1256 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2636   -0.8848   -0.0863 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4742   -1.9834    0.1716 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3779   -3.0816    0.1021 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0263   -4.2386    0.9530 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8323   -4.8648    0.7026 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6034   -3.4029   -1.3638 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.9054   -3.8553   -1.6146 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4366   -2.1162   -2.1886 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.1451   -2.2608   -3.3537 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1349   -1.0023   -1.2902 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.3955   -1.5260   -1.1417 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9376    2.2940   -0.9133 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7459    3.2484   -1.4598 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1325    3.0498   -1.6449 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8975    4.0668   -2.2041 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.7447    1.8687   -1.2791 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1017    1.6714   -1.4551 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9210    0.9188   -0.7325 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5830    1.1049   -0.5499 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4121    1.2535   -1.0164 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.2200    1.2085   -1.7868 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5447    1.6588   -1.8885 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.0948    1.8575   -3.1932 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6857    0.6845   -1.8820 C   0  0  2  0  0  0  0  0  0  0  0  0
   -7.9024    1.3317   -2.2173 O   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  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 11 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 28 29  1  0  0  0  0
 29 30  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
 31 34  1  0  0  0  0
 34 35  1  0  0  0  0
 34 36  1  0  0  0  0
 36 37  1  0  0  0  0
 36 38  1  0  0  0  0
 38 39  1  0  0  0  0
 25 40  1  0  0  0  0
 40 41  2  0  0  0  0
 41 42  1  0  0  0  0
 42 43  1  0  0  0  0
 42 44  2  0  0  0  0
 44 45  1  0  0  0  0
 44 46  1  0  0  0  0
 46 47  2  0  0  0  0
  4 48  1  0  0  0  0
 48 49  1  0  0  0  0
 48 50  1  0  0  0  0
 50 51  1  0  0  0  0
 50 52  1  0  0  0  0
 52 53  1  0  0  0  0
 52  2  1  0  0  0  0
 15  6  1  0  0  0  0
 28 17  1  0  0  0  0
 38 29  1  0  0  0  0
 47 40  1  0  0  0  0
 27 21  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0045021

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@H]1O[C@H](O[C@@H]2[C@@H](O)[C@@H](O)[C@@H](CO)O[C@@H]2OC2=CC(O)=C3C(=O)C=C(OC3=C2[C@H]2O[C@@H](CO)[C@H](O)[C@H](O)[C@@H]2O)C2=CC(O)=C(O)C=C2)[C@@H](O)[C@@H](O)[C@@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C33H40O20/c1-9-21(40)24(43)28(47)32(48-9)53-31-26(45)23(42)18(8-35)52-33(31)51-16-6-14(39)19-13(38)5-15(10-2-3-11(36)12(37)4-10)49-29(19)20(16)30-27(46)25(44)22(41)17(7-34)50-30/h2-6,9,17-18,21-28,30-37,39-47H,7-8H2,1H3/t9-,17+,18-,21-,22+,23+,24+,25+,26+,27+,28+,30-,31-,32-,33+/m1/s1

> <INCHI_KEY>
JDOFHNMFDMQLAO-MVXLWSPJSA-N

> <FORMULA>
C33H40O20

> <MOLECULAR_WEIGHT>
756.663

> <EXACT_MASS>
756.211293688

> <JCHEM_ACCEPTOR_COUNT>
20

> <JCHEM_ATOM_COUNT>
93

> <JCHEM_AVERAGE_POLARIZABILITY>
72.25596108005686

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
13

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
7-{[(2R,3R,4S,5R,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-{[(2R,3S,4S,5S,6R)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-2-yl]oxy}-2-(3,4-dihydroxyphenyl)-5-hydroxy-8-[(2R,3S,4R,5R,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-4H-chromen-4-one

> <ALOGPS_LOGP>
-0.92

> <JCHEM_LOGP>
-3.3461908653333325

> <ALOGPS_LOGS>
-1.70

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.718363422430048

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.240523391469244

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6491267221642607

> <JCHEM_POLAR_SURFACE_AREA>
335.44

> <JCHEM_REFRACTIVITY>
171.0271

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.51e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
7-{[(2R,3R,4S,5R,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-{[(2R,3S,4S,5S,6R)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-2-yl]oxy}-2-(3,4-dihydroxyphenyl)-5-hydroxy-8-[(2R,3S,4R,5R,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]chromen-4-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 19-MAR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-MAR-20         0                                  
HETATM    1  C   UNK     0      -8.042  -0.770  -0.437  0.00  0.00           C+0
HETATM    2  C   UNK     0      -6.855   0.191  -0.485  0.00  0.00           C+0
HETATM    3  O   UNK     0      -5.795  -0.455   0.040  0.00  0.00           O+0
HETATM    4  C   UNK     0      -4.515  -0.072  -0.356  0.00  0.00           C+0
HETATM    5  O   UNK     0      -3.680  -0.115   0.745  0.00  0.00           O+0
HETATM    6  C   UNK     0      -2.743  -1.148   0.765  0.00  0.00           C+0
HETATM    7  C   UNK     0      -3.433  -2.155   1.794  0.00  0.00           C+0
HETATM    8  O   UNK     0      -2.564  -3.153   2.133  0.00  0.00           O+0
HETATM    9  C   UNK     0      -3.701  -1.273   2.971  0.00  0.00           C+0
HETATM   10  O   UNK     0      -3.659  -2.093   4.134  0.00  0.00           O+0
HETATM   11  C   UNK     0      -2.942  -0.032   3.139  0.00  0.00           C+0
HETATM   12  C   UNK     0      -2.530   0.014   4.629  0.00  0.00           C+0
HETATM   13  O   UNK     0      -1.599  -1.013   4.808  0.00  0.00           O+0
HETATM   14  O   UNK     0      -1.783   0.199   2.452  0.00  0.00           O+0
HETATM   15  C   UNK     0      -1.514  -0.797   1.473  0.00  0.00           C+0
HETATM   16  O   UNK     0      -0.350  -0.614   0.764  0.00  0.00           O+0
HETATM   17  C   UNK     0       0.364   0.551   0.535  0.00  0.00           C+0
HETATM   18  C   UNK     0      -0.163   1.792   0.701  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.547   2.980   0.495  0.00  0.00           C+0
HETATM   20  O   UNK     0      -0.047   4.173   0.668  0.00  0.00           O+0
HETATM   21  C   UNK     0       1.871   2.877   0.101  0.00  0.00           C+0
HETATM   22  C   UNK     0       2.689   3.966  -0.095  0.00  0.00           C+0
HETATM   23  O   UNK     0       2.239   5.135   0.037  0.00  0.00           O+0
HETATM   24  C   UNK     0       4.005   3.745  -0.438  0.00  0.00           C+0
HETATM   25  C   UNK     0       4.536   2.490  -0.590  0.00  0.00           C+0
HETATM   26  O   UNK     0       3.708   1.488  -0.400  0.00  0.00           O+0
HETATM   27  C   UNK     0       2.427   1.623  -0.070  0.00  0.00           C+0
HETATM   28  C   UNK     0       1.698   0.448   0.126  0.00  0.00           C+0
HETATM   29  C   UNK     0       2.264  -0.885  -0.086  0.00  0.00           C+0
HETATM   30  O   UNK     0       1.474  -1.983   0.172  0.00  0.00           O+0
HETATM   31  C   UNK     0       2.378  -3.082   0.102  0.00  0.00           C+0
HETATM   32  C   UNK     0       2.026  -4.239   0.953  0.00  0.00           C+0
HETATM   33  O   UNK     0       0.832  -4.865   0.703  0.00  0.00           O+0
HETATM   34  C   UNK     0       2.603  -3.403  -1.364  0.00  0.00           C+0
HETATM   35  O   UNK     0       3.905  -3.855  -1.615  0.00  0.00           O+0
HETATM   36  C   UNK     0       2.437  -2.116  -2.189  0.00  0.00           C+0
HETATM   37  O   UNK     0       3.145  -2.261  -3.354  0.00  0.00           O+0
HETATM   38  C   UNK     0       3.135  -1.002  -1.290  0.00  0.00           C+0
HETATM   39  O   UNK     0       4.396  -1.526  -1.142  0.00  0.00           O+0
HETATM   40  C   UNK     0       5.938   2.294  -0.913  0.00  0.00           C+0
HETATM   41  C   UNK     0       6.746   3.248  -1.460  0.00  0.00           C+0
HETATM   42  C   UNK     0       8.133   3.050  -1.645  0.00  0.00           C+0
HETATM   43  O   UNK     0       8.898   4.067  -2.204  0.00  0.00           O+0
HETATM   44  C   UNK     0       8.745   1.869  -1.279  0.00  0.00           C+0
HETATM   45  O   UNK     0      10.102   1.671  -1.455  0.00  0.00           O+0
HETATM   46  C   UNK     0       7.921   0.919  -0.733  0.00  0.00           C+0
HETATM   47  C   UNK     0       6.583   1.105  -0.550  0.00  0.00           C+0
HETATM   48  C   UNK     0      -4.412   1.254  -1.016  0.00  0.00           C+0
HETATM   49  O   UNK     0      -3.220   1.208  -1.787  0.00  0.00           O+0
HETATM   50  C   UNK     0      -5.545   1.659  -1.889  0.00  0.00           C+0
HETATM   51  O   UNK     0      -5.095   1.857  -3.193  0.00  0.00           O+0
HETATM   52  C   UNK     0      -6.686   0.685  -1.882  0.00  0.00           C+0
HETATM   53  O   UNK     0      -7.902   1.332  -2.217  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   52                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   48                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7   15                                                  
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   14                                                  
CONECT   12   11   13                                                       
CONECT   13   12                                                            
CONECT   14   11   15                                                       
CONECT   15   14   16    6                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   28                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22   27                                                  
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25                                                       
CONECT   25   24   26   40                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28   21                                                  
CONECT   28   27   29   17                                                  
CONECT   29   28   30   38                                                  
CONECT   30   29   31                                                       
CONECT   31   30   32   34                                                  
CONECT   32   31   33                                                       
CONECT   33   32                                                            
CONECT   34   31   35   36                                                  
CONECT   35   34                                                            
CONECT   36   34   37   38                                                  
CONECT   37   36                                                            
CONECT   38   36   39   29                                                  
CONECT   39   38                                                            
CONECT   40   25   41   47                                                  
CONECT   41   40   42                                                       
CONECT   42   41   43   44                                                  
CONECT   43   42                                                            
CONECT   44   42   45   46                                                  
CONECT   45   44                                                            
CONECT   46   44   47                                                       
CONECT   47   46   40                                                       
CONECT   48    4   49   50                                                  
CONECT   49   48                                                            
CONECT   50   48   51   52                                                  
CONECT   51   50                                                            
CONECT   52   50   53    2                                                  
CONECT   53   52                                                            
MASTER        0    0    0    0    0    0    0    0   53    0  116    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₃H₄₀O₂₀

Average Mass

756.6630 Da

Monoisotopic Mass

756.21129 Da

IUPAC Name

7-{[(2R,3R,4S,5R,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-{[(2R,3S,4S,5S,6R)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-2-yl]oxy}-2-(3,4-dihydroxyphenyl)-5-hydroxy-8-[(2R,3S,4R,5R,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-4H-chromen-4-one

Traditional Name

CAS Registry Number

Not Available

SMILES

C[C@H]1O[C@H](O[C@@H]2[C@@H](O)[C@@H](O)[C@@H](CO)O[C@@H]2OC2=CC(O)=C3C(=O)C=C(OC3=C2[C@H]2O[C@@H](CO)[C@H](O)[C@H](O)[C@@H]2O)C2=CC(O)=C(O)C=C2)[C@@H](O)[C@@H](O)[C@@H]1O

InChI Identifier

InChI=1S/C33H40O20/c1-9-21(40)24(43)28(47)32(48-9)53-31-26(45)23(42)18(8-35)52-33(31)51-16-6-14(39)19-13(38)5-15(10-2-3-11(36)12(37)4-10)49-29(19)20(16)30-27(46)25(44)22(41)17(7-34)50-30/h2-6,9,17-18,21-28,30-37,39-47H,7-8H2,1H3/t9-,17+,18-,21-,22+,23+,24+,25+,26+,27+,28+,30-,31-,32-,33+/m1/s1

InChI Key

JDOFHNMFDMQLAO-MVXLWSPJSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Cannabis sativa	NULL	Not Available

Chemical Taxonomy

Classification

Not classified

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	-0.92	ALOGPS
logP	-3.3	ChemAxon
logS	-1.7	ALOGPS
pKa (Strongest Acidic)	7.24	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	20	ChemAxon
Hydrogen Donor Count	13	ChemAxon
Polar Surface Area	335.44 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	171.03 m³·mol⁻¹	ChemAxon
Polarizability	72.26 Å³	ChemAxon
Number of Rings	6	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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for Orientin-7-o-rhamnoglucoside (NP0045021)

MOL for NP0045021 (Orientin-7-o-rhamnoglucoside)

3D MOL for NP0045021 (Orientin-7-o-rhamnoglucoside)

3D SDF for NP0045021 (Orientin-7-o-rhamnoglucoside)

3D-SDF for NP0045021 (Orientin-7-o-rhamnoglucoside)

PDB for NP0045021 (Orientin-7-o-rhamnoglucoside)

3D PDB for NP0045021 (Orientin-7-o-rhamnoglucoside)

SMILES for NP0045021 (Orientin-7-o-rhamnoglucoside)

INCHI for NP0045021 (Orientin-7-o-rhamnoglucoside)

Structure for NP0045021 (Orientin-7-o-rhamnoglucoside)

3D Structure for NP0045021 (Orientin-7-o-rhamnoglucoside)