NP-MRD: Showing NP-Card for Glycyrrhizic acid (NP0052079)

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Record Information

Version

2.0

Created at

2022-04-27 23:15:02 UTC

Updated at

2022-04-27 23:15:02 UTC

NP-MRD ID

NP0052079

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Glycyrrhizic acid

Description

(2R,3S,4S,5R,6R)-6-{[(2S,3R,4S,5S,6R)-2-{[(3S,4aR,6aR,6bS,8aS,11S,12aR,14aR,14bS)-11-carboxy-4,4,6a,6b,8a,11,14b-heptamethyl-14-oxo-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,14,14a,14b-icosahydropicen-3-yl]oxy}-6-carboxy-4,5-dihydroxyoxan-3-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid belongs to the class of organic compounds known as triterpene saponins. These are glycosylated derivatives of triterpene sapogenins. The sapogenin moiety backbone is usually based on the oleanane, ursane, taraxastane, bauerane, lanostane, lupeol, lupane, dammarane, cycloartane, friedelane, hopane, 9b,19-cyclo-lanostane, cycloartane, or cycloartanol skeleton. Glycyrrhizic acid is found in Abrus precatorius , Glycyrrhiza aspera, Glycyrrhiza glabra , Glycyrrhiza inflata , Glycyrrhiza kansuensis, Glycyrrhiza radix, Glycyrrhiza uralensis and Stevia rebaudiana . Based on a literature review very few articles have been published on (2R,3S,4S,5R,6R)-6-{[(2S,3R,4S,5S,6R)-2-{[(3S,4aR,6aR,6bS,8aS,11S,12aR,14aR,14bS)-11-carboxy-4,4,6a,6b,8a,11,14b-heptamethyl-14-oxo-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,14,14a,14b-icosahydropicen-3-yl]oxy}-6-carboxy-4,5-dihydroxyoxan-3-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282201152D          

 58 64  0  0  1  0            999 V2000
    6.0770    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4895    0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.0770   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2520   -0.3020    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.8395    0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.2520    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0145    0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.6020   -0.3020    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.0145   -1.0164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8395   -1.0164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770   -0.3020    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3645    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6020    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0145    1.8414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395    0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1270   -0.3020    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5395   -1.0164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -1.0164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1105    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020    1.1270    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1270    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2732    1.9515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3977    1.5642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1261    1.1768    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3689    2.3887    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.0164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1895   -1.0164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6882   -1.1225    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4270    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7766   -0.7392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1058   -1.1265    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3145    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7270    1.1270    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.3145    1.8414    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.7270    2.5559    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.5520    2.5559    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.9645    1.8414    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.5520    1.1270    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.7895    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2020    1.1270    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.2020    2.5559    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.9645    3.2704    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3145    3.2704    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4895    1.8414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0770    2.5559    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.2520    2.5559    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.8395    3.2704    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.2520    3.9849    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.0770    3.9849    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.4895    3.2704    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4895    4.6993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0770    5.4138    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3145    4.6993    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8395    4.6993    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0145    3.2704    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8395    1.8414    0.0000 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
  1  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  4 10  1  6  0  0  0
  8 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
  7 14  1  6  0  0  0
 14 15  2  0  0  0  0
 16 12  1  1  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 11 19  1  0  0  0  0
 17 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 16 23  1  0  0  0  0
 22 24  1  1  0  0  0
 22 25  1  6  0  0  0
 25 26  2  0  0  0  0
 25 27  1  0  0  0  0
 17 28  1  6  0  0  0
 11 29  1  1  0  0  0
  8 30  1  6  0  0  0
  5 31  1  6  0  0  0
  3 32  1  0  0  0  0
  3 33  1  0  0  0  0
  2 34  1  6  0  0  0
 35 34  1  6  0  0  0
 35 36  1  0  0  0  0
 36 37  1  0  0  0  0
 37 38  1  0  0  0  0
 38 39  1  0  0  0  0
 39 40  1  0  0  0  0
 35 40  1  0  0  0  0
 39 41  1  6  0  0  0
 41 42  2  0  0  0  0
 41 43  1  0  0  0  0
 38 44  1  6  0  0  0
 37 45  1  1  0  0  0
 36 46  1  6  0  0  0
 47 46  1  1  0  0  0
 47 48  1  0  0  0  0
 48 49  1  0  0  0  0
 49 50  1  0  0  0  0
 50 51  1  0  0  0  0
 51 52  1  0  0  0  0
 47 52  1  0  0  0  0
 51 53  1  6  0  0  0
 53 54  2  0  0  0  0
 53 55  1  0  0  0  0
 50 56  1  6  0  0  0
 49 57  1  1  0  0  0
 48 58  1  6  0  0  0
M  END

     RDKit          3D

120126  0  0  0  0  0  0  0  0999 V2000
   -1.9788   -2.1102   -1.6478 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3832   -0.7571   -1.3935 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.5354    0.0108   -2.7192 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1850    0.0701   -0.4205 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.4874    0.2755   -0.7209 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8951    1.5532   -0.9498 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.4152    1.8127   -2.1860 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7073    3.1204   -2.4398 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.9018    3.1784   -3.2901 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3619    4.2818   -3.6435 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5175    2.0252   -3.7008 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8991    3.9887   -1.2610 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.8956    4.9730   -1.5008 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1965    3.3836    0.0415 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.5886    4.1966    1.0433 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8009    1.9697    0.1885 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.9467    1.1677    0.0693 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1597    0.3625    1.1831 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.0331   -0.9688    0.9394 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1147   -1.4299    0.2034 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.8065   -2.7553   -0.3361 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6876   -3.2767   -0.0913 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7019   -3.4777   -1.1165 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3712   -1.4378    1.0710 C   0  0  1  0  0  0  0  0  0  0  0  0
   -8.5484   -2.7424    1.5151 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1370   -0.5671    2.2963 C   0  0  2  0  0  0  0  0  0  0  0  0
   -9.3911   -0.2867    2.8465 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3935    0.6920    1.9329 C   0  0  1  0  0  0  0  0  0  0  0  0
   -7.1568    1.4161    3.1030 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9265   -0.3521    1.0089 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4291   -0.1108    1.2658 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4174   -0.9963    0.3990 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2164   -2.3956    0.8774 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0443   -0.7537   -1.0455 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8556   -1.6423   -1.9633 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2735   -1.0651   -1.9287 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7869   -1.1431   -0.5119 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.1666   -2.5554   -0.2304 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8520   -0.5536    0.5130 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4759   -0.6992    1.8143 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8527   -0.8212    2.8831 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9303   -0.7050    1.8901 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6975   -0.5226    0.8260 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1844   -0.5481    1.0186 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.5397    0.8269    1.5351 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0010    0.9898    1.7850 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.2592    2.4761    2.0497 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4715    0.2498    2.9634 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3324   -0.6539    2.9793 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8921    0.5981    4.1897 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.7350    0.6598    0.5175 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4043   -0.6864   -0.0265 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9247   -0.9412   -0.2163 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.7604   -2.4266   -0.4584 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3689   -0.1313   -1.3684 C   0  0  0  0  0  0  0  0  0  0  0  0
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    4.0381   -0.2901   -0.4734 C   0  0  1  0  0  0  0  0  0  0  0  0
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   -1.2454   -2.6865   -2.2491 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8796   -1.9996   -2.3201 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1839   -2.6881   -0.7388 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2922    1.0785   -2.6059 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0267   -0.4815   -3.5612 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6337   -0.0533   -2.9935 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6924    1.0959   -0.4580 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9874    2.2210   -0.8422 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8576    3.4961   -3.0898 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2226    1.4443   -4.4718 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9623    4.6225   -1.1634 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7534    4.4952   -1.3296 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2899    3.4810    0.2822 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8630    3.9017    1.9467 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3156    1.7749    1.1768 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2964    0.6232    1.8822 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3072   -0.7389   -0.6400 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5612   -3.0541   -1.4537 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2569   -1.1138    0.5311 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0800   -3.3077    0.9027 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5226   -1.1521    3.0079 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.7313   -1.1700    3.1959 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1039    1.2634    1.2592 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2921    0.8287    3.8944 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4338    0.3937    1.6572 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2559   -1.3539    1.2571 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3206   -0.2827    2.3528 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2543    0.9607    0.9750 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0109   -3.1464    0.1183 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6193   -2.4869    1.6382 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1174   -2.6431    1.5184 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4171    0.2983   -1.2539 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8506   -2.7086   -1.6599 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4801   -1.5407   -2.9843 H   0  0  0  0  0  0  0  0  0  0  0  0
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 11 68  1  0
M  END


  Mrv1652304282201152D          

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    4.8395    3.2704    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.2520    3.9849    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.0770    3.9849    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
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  8 11  1  0  0  0  0
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 12 13  2  0  0  0  0
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  8 30  1  6  0  0  0
  5 31  1  6  0  0  0
  3 32  1  0  0  0  0
  3 33  1  0  0  0  0
  2 34  1  6  0  0  0
 35 34  1  6  0  0  0
 35 36  1  0  0  0  0
 36 37  1  0  0  0  0
 37 38  1  0  0  0  0
 38 39  1  0  0  0  0
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 35 40  1  0  0  0  0
 39 41  1  6  0  0  0
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 38 44  1  6  0  0  0
 37 45  1  1  0  0  0
 36 46  1  6  0  0  0
 47 46  1  1  0  0  0
 47 48  1  0  0  0  0
 48 49  1  0  0  0  0
 49 50  1  0  0  0  0
 50 51  1  0  0  0  0
 51 52  1  0  0  0  0
 47 52  1  0  0  0  0
 51 53  1  6  0  0  0
 53 54  2  0  0  0  0
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 50 56  1  6  0  0  0
 49 57  1  1  0  0  0
 48 58  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0052079

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1(C)[C@H](CC[C@@]2(C)[C@H]1CC[C@]1(C)[C@@H]2C(=O)C=C2[C@@H]3C[C@](C)(CC[C@]3(C)CC[C@@]12C)C(O)=O)O[C@H]1O[C@H]([C@@H](O)[C@H](O)[C@H]1O[C@@H]1O[C@H]([C@@H](O)[C@H](O)[C@H]1O)C(O)=O)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C42H62O16/c1-37(2)21-8-11-42(7)31(20(43)16-18-19-17-39(4,36(53)54)13-12-38(19,3)14-15-41(18,42)6)40(21,5)10-9-22(37)55-35-30(26(47)25(46)29(57-35)33(51)52)58-34-27(48)23(44)24(45)28(56-34)32(49)50/h16,19,21-31,34-35,44-48H,8-15,17H2,1-7H3,(H,49,50)(H,51,52)(H,53,54)/t19-,21-,22-,23-,24-,25-,26-,27+,28+,29+,30+,31+,34-,35-,38+,39-,40-,41+,42+/m0/s1

> <INCHI_KEY>
LPLVUJXQOOQHMX-MYOOOWEVSA-N

> <FORMULA>
C42H62O16

> <MOLECULAR_WEIGHT>
822.942

> <EXACT_MASS>
822.403785916

> <JCHEM_ACCEPTOR_COUNT>
16

> <JCHEM_ATOM_COUNT>
120

> <JCHEM_AVERAGE_POLARIZABILITY>
85.8833319387164

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
8

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R,3S,4S,5R,6S)-6-{[(3S,4aR,6aR,6bS,8aS,11S,12aR,14aR,14bS)-11-carboxy-4,4,6a,6b,8a,11,14b-heptamethyl-14-oxo-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,14,14a,14b-icosahydropicen-3-yl]oxy}-5-{[(2R,3R,4S,5S,6R)-6-carboxy-3,4,5-trihydroxyoxan-2-yl]oxy}-3,4-dihydroxyoxane-2-carboxylic acid

> <ALOGPS_LOGP>
2.78

> <JCHEM_LOGP>
3.1302058209999997

> <ALOGPS_LOGS>
-4.18

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-3

> <JCHEM_PKA>
3.5738490011649686

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.961005004154196

> <JCHEM_PKA_STRONGEST_BASIC>
-3.731980846359378

> <JCHEM_POLAR_SURFACE_AREA>
267.03999999999996

> <JCHEM_REFRACTIVITY>
198.8299000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
5.45e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2R,3S,4S,5R,6S)-6-{[(3S,4aR,6aR,6bS,8aS,11S,12aR,14aR,14bS)-11-carboxy-4,4,6a,6b,8a,11,14b-heptamethyl-14-oxo-2,3,4a,5,6,7,8,9,10,12,12a,14a-dodecahydro-1H-picen-3-yl]oxy}-5-{[(2R,3R,4S,5S,6R)-6-carboxy-3,4,5-trihydroxyoxan-2-yl]oxy}-3,4-dihydroxyoxane-2-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0      11.344   2.104   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      12.114   0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      11.344  -0.564   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.804  -0.564   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       9.034   0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.804   2.104   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.494   0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.724  -0.564   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.494  -1.897   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.034  -1.897   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.184  -0.564   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.414   0.770   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.184   2.104   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.724   2.104   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       7.494   3.437   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       2.874   0.770   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.104  -0.564   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.874  -1.897   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.414  -1.897   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.564  -0.564   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -0.206   0.770   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       0.564   2.104   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       2.104   2.104   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       0.510   3.643   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -0.742   2.920   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      -2.102   2.197   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0      -0.689   4.459   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       1.334  -1.897   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       5.954  -1.897   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       6.885  -2.095   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       8.264   2.104   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      12.650  -1.380   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      11.397  -2.103   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      13.654   0.770   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0      14.424   2.104   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      13.654   3.437   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      14.424   4.771   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      15.964   4.771   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      16.734   3.437   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0      15.964   2.104   0.000  0.00  0.00           O+0
HETATM   41  C   UNK     0      18.274   3.437   0.000  0.00  0.00           C+0
HETATM   42  O   UNK     0      19.044   2.104   0.000  0.00  0.00           O+0
HETATM   43  O   UNK     0      19.044   4.771   0.000  0.00  0.00           O+0
HETATM   44  O   UNK     0      16.734   6.105   0.000  0.00  0.00           O+0
HETATM   45  O   UNK     0      13.654   6.105   0.000  0.00  0.00           O+0
HETATM   46  O   UNK     0      12.114   3.437   0.000  0.00  0.00           O+0
HETATM   47  C   UNK     0      11.344   4.771   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0       9.804   4.771   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0       9.034   6.105   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0       9.804   7.438   0.000  0.00  0.00           C+0
HETATM   51  C   UNK     0      11.344   7.438   0.000  0.00  0.00           C+0
HETATM   52  O   UNK     0      12.114   6.105   0.000  0.00  0.00           O+0
HETATM   53  C   UNK     0      12.114   8.772   0.000  0.00  0.00           C+0
HETATM   54  O   UNK     0      11.344  10.106   0.000  0.00  0.00           O+0
HETATM   55  O   UNK     0      13.654   8.772   0.000  0.00  0.00           O+0
HETATM   56  O   UNK     0       9.034   8.772   0.000  0.00  0.00           O+0
HETATM   57  O   UNK     0       7.494   6.105   0.000  0.00  0.00           O+0
HETATM   58  O   UNK     0       9.034   3.437   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3   34                                                  
CONECT    3    2    4   32   33                                             
CONECT    4    3    5   10                                                  
CONECT    5    4    6    7   31                                             
CONECT    6    5    1                                                       
CONECT    7    5    8   14                                                  
CONECT    8    7    9   11   30                                             
CONECT    9    8   10                                                       
CONECT   10    9    4                                                       
CONECT   11    8   12   19   29                                             
CONECT   12   11   13   16                                                  
CONECT   13   12   14                                                       
CONECT   14   13    7   15                                                  
CONECT   15   14                                                            
CONECT   16   12   17   23                                                  
CONECT   17   16   18   20   28                                             
CONECT   18   17   19                                                       
CONECT   19   18   11                                                       
CONECT   20   17   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23   24   25                                             
CONECT   23   22   16                                                       
CONECT   24   22                                                            
CONECT   25   22   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25                                                            
CONECT   28   17                                                            
CONECT   29   11                                                            
CONECT   30    8                                                            
CONECT   31    5                                                            
CONECT   32    3                                                            
CONECT   33    3                                                            
CONECT   34    2   35                                                       
CONECT   35   34   36   40                                                  
CONECT   36   35   37   46                                                  
CONECT   37   36   38   45                                                  
CONECT   38   37   39   44                                                  
CONECT   39   38   40   41                                                  
CONECT   40   39   35                                                       
CONECT   41   39   42   43                                                  
CONECT   42   41                                                            
CONECT   43   41                                                            
CONECT   44   38                                                            
CONECT   45   37                                                            
CONECT   46   36   47                                                       
CONECT   47   46   48   52                                                  
CONECT   48   47   49   58                                                  
CONECT   49   48   50   57                                                  
CONECT   50   49   51   56                                                  
CONECT   51   50   52   53                                                  
CONECT   52   51   47                                                       
CONECT   53   51   54   55                                                  
CONECT   54   53                                                            
CONECT   55   53                                                            
CONECT   56   50                                                            
CONECT   57   49                                                            
CONECT   58   48                                                            
MASTER        0    0    0    0    0    0    0    0   58    0  128    0
END

View in JSmol

Synonyms

Value	Source
(2R,3S,4S,5R,6R)-6-{[(2S,3R,4S,5S,6R)-2-{[(3S,4ar,6ar,6BS,8as,11S,12ar,14ar,14BS)-11-carboxy-4,4,6a,6b,8a,11,14b-heptamethyl-14-oxo-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,14,14a,14b-icosahydropicen-3-yl]oxy}-6-carboxy-4,5-dihydroxyoxan-3-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylate	Generator

Chemical Formula

C₄₂H₆₂O₁₆

Average Mass

822.9420 Da

Monoisotopic Mass

822.40379 Da

IUPAC Name

(2R,3S,4S,5R,6S)-6-{[(3S,4aR,6aR,6bS,8aS,11S,12aR,14aR,14bS)-11-carboxy-4,4,6a,6b,8a,11,14b-heptamethyl-14-oxo-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,14,14a,14b-icosahydropicen-3-yl]oxy}-5-{[(2R,3R,4S,5S,6R)-6-carboxy-3,4,5-trihydroxyoxan-2-yl]oxy}-3,4-dihydroxyoxane-2-carboxylic acid

Traditional Name

(2R,3S,4S,5R,6S)-6-{[(3S,4aR,6aR,6bS,8aS,11S,12aR,14aR,14bS)-11-carboxy-4,4,6a,6b,8a,11,14b-heptamethyl-14-oxo-2,3,4a,5,6,7,8,9,10,12,12a,14a-dodecahydro-1H-picen-3-yl]oxy}-5-{[(2R,3R,4S,5S,6R)-6-carboxy-3,4,5-trihydroxyoxan-2-yl]oxy}-3,4-dihydroxyoxane-2-carboxylic acid

CAS Registry Number

Not Available

SMILES

CC1(C)[C@H](CC[C@@]2(C)[C@H]1CC[C@]1(C)[C@@H]2C(=O)C=C2[C@@H]3C[C@](C)(CC[C@]3(C)CC[C@@]12C)C(O)=O)O[C@H]1O[C@H]([C@@H](O)[C@H](O)[C@H]1O[C@@H]1O[C@H]([C@@H](O)[C@H](O)[C@H]1O)C(O)=O)C(O)=O

InChI Identifier

InChI=1S/C42H62O16/c1-37(2)21-8-11-42(7)31(20(43)16-18-19-17-39(4,36(53)54)13-12-38(19,3)14-15-41(18,42)6)40(21,5)10-9-22(37)55-35-30(26(47)25(46)29(57-35)33(51)52)58-34-27(48)23(44)24(45)28(56-34)32(49)50/h16,19,21-31,34-35,44-48H,8-15,17H2,1-7H3,(H,49,50)(H,51,52)(H,53,54)/t19-,21-,22-,23-,24-,25-,26-,27+,28+,29+,30+,31+,34-,35-,38+,39-,40-,41+,42+/m0/s1

InChI Key

LPLVUJXQOOQHMX-MYOOOWEVSA-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
Abrus precatorius	Plant	KNApSAcK
Glycyrrhiza aspera	Plant	KNApSAcK
Glycyrrhiza glabra	Plant	KNApSAcK
Glycyrrhiza inflata	Plant	KNApSAcK
Glycyrrhiza kansuensis	Plant	KNApSAcK
Glycyrrhiza radix	Plant	KNApSAcK
Glycyrrhiza uralensis	Plant	KNApSAcK
Stevia rebaudiana	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as triterpene saponins. These are glycosylated derivatives of triterpene sapogenins. The sapogenin moiety backbone is usually based on the oleanane, ursane, taraxastane, bauerane, lanostane, lupeol, lupane, dammarane, cycloartane, friedelane, hopane, 9b,19-cyclo-lanostane, cycloartane, or cycloartanol skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene glycosides

Direct Parent

Triterpene saponins

Alternative Parents

Substituents

Triterpene saponin
Triterpenoid
O-glucuronide
1-o-glucuronide
Glucuronic acid or derivatives
O-glycosyl compound
Glycosyl compound
Disaccharide
Tricarboxylic acid or derivatives
Cyclohexenone
Beta-hydroxy acid
Pyran
Oxane
Hydroxy acid
Secondary alcohol
Ketone
Oxacycle
Organoheterocyclic compound
Polyol
Carboxylic acid
Carboxylic acid derivative
Acetal
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic 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	2.78	ALOGPS
logP	3.13	ChemAxon
logS	-4.2	ALOGPS
pKa (Strongest Acidic)	2.96	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	-3	ChemAxon
Hydrogen Acceptor Count	16	ChemAxon
Hydrogen Donor Count	8	ChemAxon
Polar Surface Area	267.04 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	198.83 m³·mol⁻¹	ChemAxon
Polarizability	85.88 Å³	ChemAxon
Number of Rings	7	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

124604970

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Glycyrrhizic acid (NP0052079)

MOL for NP0052079 (Glycyrrhizic acid)

3D MOL for NP0052079 (Glycyrrhizic acid)

3D SDF for NP0052079 (Glycyrrhizic acid)

3D-SDF for NP0052079 (Glycyrrhizic acid)

PDB for NP0052079 (Glycyrrhizic acid)

3D PDB for NP0052079 (Glycyrrhizic acid)

SMILES for NP0052079 (Glycyrrhizic acid)

INCHI for NP0052079 (Glycyrrhizic acid)

Structure for NP0052079 (Glycyrrhizic acid)

3D Structure for NP0052079 (Glycyrrhizic acid)