NP-MRD: Showing NP-Card for Glycyrrhetinic acid (NP0001174)

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Record Information

Version

2.0

Created at

2009-01-30 10:07:36 UTC

Updated at

2024-09-17 15:44:20 UTC

NP-MRD ID

NP0001174

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Glycyrrhetinic acid

Description

Glycyrrhetinic acid is a pentacyclic triterpenoid derivative of the beta-amyrin type obtained from the hydrolysis of glycyrrhizic acid, which was first obtained from the herb liquorice. It is used in flavouring and it masks the bitter taste of drugs like aloe and quinine. It is effective in the treatment of peptic ulcer and also has expectorant (antitussive) properties (PMID:32106571 ). In glycyrrhetinic acid the functional group (R) is a hydroxyl group. Research in 2005 demonstrated that with a proper functional group a very effective glycyrrhetinic artificial sweetener can be obtained. When R is an anionic NHCO(CH2)CO2K side chain, the sweetening effect is found to 1200 times that of sugar (human sensory panel data). A shorter or longer spacer reduces the sweetening effect. One explanation is that the taste bud cell receptor has 1.3 Nanometers (13 angstroms) available for docking with the sweetener molecule. In addition the sweetener molecule requires three proton donor positions of which two reside at the extremities to be able to interact efficiently with the receptor cavity.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI


  Mrv1652304202021192D          

 34 38  0  0  1  0            999 V2000
    8.5993  -19.6826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1861  -18.9685    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9002  -18.5554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6150  -18.9672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3291  -18.5539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3283  -17.7289    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    9.6134  -17.3172    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8994  -17.7304    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.1845  -17.3185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4704  -17.7318    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4712  -18.5568    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.7572  -18.9700    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.8986  -16.9054    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6126  -16.4922    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8978  -16.0804    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.3267  -16.0789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0415  -16.4907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0424  -17.3157    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   11.7572  -17.7276    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4713  -17.3143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4705  -16.4893    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   11.7556  -16.0776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7548  -15.2526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4689  -14.8393    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   13.1837  -15.2511    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1845  -16.0761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0557  -14.1253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8807  -14.1245    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4675  -13.4104    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.7057  -14.1237    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.1854  -16.9011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6702  -16.9181    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0432  -18.1407    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7743  -19.6834    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
  2 11  1  0  0  0  0
  2 34  1  0  0  0  0
  3  4  1  0  0  0  0
  3  8  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
  6 18  1  0  0  0  0
  6 33  1  1  0  0  0
  7  8  1  0  0  0  0
  7 14  1  0  0  0  0
  8  9  1  0  0  0  0
  8 13  1  1  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  1  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 17 22  1  0  0  0  0
 18 19  1  0  0  0  0
 18 32  1  6  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 26  1  0  0  0  0
 21 31  1  1  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 24 27  1  6  0  0  0
 24 28  1  1  0  0  0
 25 26  1  0  0  0  0
 28 29  2  0  0  0  0
 28 30  1  0  0  0  0
M  END

HMDB0011628
     RDKit          3D
Glycyrrhetinic acid
 80 84  0  0  0  0  0  0  0  0999 V2000
    4.6063    0.3583   -2.0694 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8407    0.1672   -0.6120 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8375    1.2605   -0.1825 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5793    0.4002    0.2346 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9953    1.6867   -0.2050 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5775    1.6663   -0.6588 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7025    0.7366    0.1956 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8145    1.2294    1.6007 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2719   -0.6210   -0.0458 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3836   -1.6411    0.5020 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7550   -2.7472    1.0033 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0588   -1.4108    0.4923 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5844   -0.2498    0.1320 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0571   -0.1367    0.1624 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7150   -0.9401   -0.9612 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1360   -1.2294   -0.4595 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.8746   -2.1235   -1.4244 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0358   -1.9628    0.8283 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5237   -1.5078    1.8815 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3888   -3.1956    0.9115 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8020    0.0889   -0.2522 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9146    1.2734   -0.5635 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6131    1.2283    0.2144 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.9798    1.6082    1.6562 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7233    2.3110   -0.3035 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3221    2.1303    0.2740 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6931    0.8662   -0.2789 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7476    0.9856   -1.8028 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7063   -0.7721    0.3603 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6663   -1.3158    1.7989 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2506   -1.9397   -0.4784 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6433   -2.2701   -0.0264 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5279   -1.1164   -0.2925 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.4643   -0.9857    0.7546 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0600   -0.5333   -2.5956 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1825    1.2274   -2.5065 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5759    0.5053   -2.3784 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2404    0.9237    0.8167 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3869    2.2464   -0.1385 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6931    1.1749   -0.8878 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0363    0.5818    1.2613 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5720    2.1668   -1.0556 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0576    2.4828    0.5994 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4494    1.3937   -1.7246 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1320    2.6770   -0.5495 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1403    0.7126    2.3082 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4931    2.3144    1.5792 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8624    1.2795    1.9830 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2574   -0.7629   -1.1696 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7442   -2.2244    0.7932 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3824   -0.6693    1.1069 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8026   -0.3726   -1.8923 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1674   -1.8692   -1.1783 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2271   -2.9974   -1.6268 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7717   -2.5106   -0.8982 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1302   -1.6072   -2.3696 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7189   -3.4940    0.1944 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6479    0.1470   -0.9967 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2517    0.1455    0.7383 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7788    1.4344   -1.6334 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4641    2.1775   -0.1701 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9667    1.1836    1.9332 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0186    2.7340    1.6939 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2434    1.2011    2.3766 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0929    3.2790    0.1477 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7337    2.4608   -1.3811 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4956    1.9340    1.3705 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7696    3.0418    0.0723 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4509    2.0358   -2.0833 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7647    0.8540   -2.1727 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1178    0.2277   -2.3014 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8838   -2.3755    1.8693 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4730   -0.7533    2.3556 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7349   -1.0897    2.3125 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6450   -2.8579   -0.3471 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2604   -1.7176   -1.5441 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7265   -2.5640    1.0245 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9526   -3.1832   -0.6165 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1614   -1.3721   -1.1930 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3110   -1.4199    0.5632 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  1
  7  9  1  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 16 18  1  1
 18 19  2  0
 18 20  1  0
 16 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  1
 23 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  6
  9 29  1  0
 29 30  1  1
 29 31  1  0
 31 32  1  0
 32 33  1  0
 33 34  1  0
 33  2  1  0
 29  4  1  0
 27  7  1  0
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 23 14  1  0
  1 35  1  0
  1 36  1  0
  1 37  1  0
  3 38  1  0
  3 39  1  0
  3 40  1  0
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  5 42  1  0
  5 43  1  0
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  8 46  1  0
  8 47  1  0
  8 48  1  0
  9 49  1  0
 12 50  1  0
 14 51  1  0
 15 52  1  0
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 17 54  1  0
 17 55  1  0
 17 56  1  0
 20 57  1  0
 21 58  1  0
 21 59  1  0
 22 60  1  0
 22 61  1  0
 24 62  1  0
 24 63  1  0
 24 64  1  0
 25 65  1  0
 25 66  1  0
 26 67  1  0
 26 68  1  0
 28 69  1  0
 28 70  1  0
 28 71  1  0
 30 72  1  0
 30 73  1  0
 30 74  1  0
 31 75  1  0
 31 76  1  0
 32 77  1  0
 32 78  1  0
 33 79  1  6
 34 80  1  0
M  END


  Mrv1652304202021192D          

 34 38  0  0  1  0            999 V2000
    8.5993  -19.6826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1861  -18.9685    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9002  -18.5554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6150  -18.9672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3291  -18.5539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3283  -17.7289    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    9.6134  -17.3172    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8994  -17.7304    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.1845  -17.3185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4704  -17.7318    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4712  -18.5568    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.7572  -18.9700    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.8986  -16.9054    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6126  -16.4922    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8978  -16.0804    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.3267  -16.0789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0415  -16.4907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0424  -17.3157    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   11.7572  -17.7276    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4713  -17.3143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4705  -16.4893    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   11.7556  -16.0776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7548  -15.2526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4689  -14.8393    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   13.1837  -15.2511    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1845  -16.0761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0557  -14.1253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8807  -14.1245    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4675  -13.4104    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.7057  -14.1237    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.1854  -16.9011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6702  -16.9181    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0432  -18.1407    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7743  -19.6834    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
  2 11  1  0  0  0  0
  2 34  1  0  0  0  0
  3  4  1  0  0  0  0
  3  8  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
  6 18  1  0  0  0  0
  6 33  1  1  0  0  0
  7  8  1  0  0  0  0
  7 14  1  0  0  0  0
  8  9  1  0  0  0  0
  8 13  1  1  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  1  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 17 22  1  0  0  0  0
 18 19  1  0  0  0  0
 18 32  1  6  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 26  1  0  0  0  0
 21 31  1  1  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 24 27  1  6  0  0  0
 24 28  1  1  0  0  0
 25 26  1  0  0  0  0
 28 29  2  0  0  0  0
 28 30  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0001174

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1(C)[C@@H](O)CC[C@@]2(C)C1CC[C@]1(C)C2C(=O)C=C2C3C[C@](C)(CC[C@]3(C)CC[C@@]12C)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C30H46O4/c1-25(2)21-8-11-30(7)23(28(21,5)10-9-22(25)32)20(31)16-18-19-17-27(4,24(33)34)13-12-26(19,3)14-15-29(18,30)6/h16,19,21-23,32H,8-15,17H2,1-7H3,(H,33,34)/t19?,21?,22-,23?,26+,27-,28-,29+,30+/m0/s1

> <INCHI_KEY>
MPDGHEJMBKOTSU-WFJWTYAKSA-N

> <FORMULA>
C30H46O4

> <MOLECULAR_WEIGHT>
470.6838

> <EXACT_MASS>
470.33960996

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
80

> <JCHEM_AVERAGE_POLARIZABILITY>
55.3864348876561

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S,4aS,6aS,6bR,10S,12aS)-10-hydroxy-2,4a,6a,6b,9,9,12a-heptamethyl-13-oxo-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicene-2-carboxylic acid

> <ALOGPS_LOGP>
5.45

> <JCHEM_LOGP>
6.031328036333333

> <ALOGPS_LOGS>
-5.44

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
19.48941909028516

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.444331881347185

> <JCHEM_PKA_STRONGEST_BASIC>
-0.8351069321304386

> <JCHEM_POLAR_SURFACE_AREA>
74.6

> <JCHEM_REFRACTIVITY>
134.2685

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.72e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S,4aS,6aS,6bR,10S,12aS)-10-hydroxy-2,4a,6a,6b,9,9,12a-heptamethyl-13-oxo-3,4,5,6,7,8,8a,10,11,12,12b,14b-dodecahydro-1H-picene-2-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0011628
     RDKit          3D
Glycyrrhetinic acid
 80 84  0  0  0  0  0  0  0  0999 V2000
    4.6063    0.3583   -2.0694 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8407    0.1672   -0.6120 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8375    1.2605   -0.1825 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5793    0.4002    0.2346 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9953    1.6867   -0.2050 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5775    1.6663   -0.6588 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7025    0.7366    0.1956 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8145    1.2294    1.6007 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2719   -0.6210   -0.0458 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3836   -1.6411    0.5020 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7550   -2.7472    1.0033 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0588   -1.4108    0.4923 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5844   -0.2498    0.1320 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0571   -0.1367    0.1624 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7150   -0.9401   -0.9612 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1360   -1.2294   -0.4595 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.8746   -2.1235   -1.4244 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0358   -1.9628    0.8283 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5237   -1.5078    1.8815 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3888   -3.1956    0.9115 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8020    0.0889   -0.2522 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9146    1.2734   -0.5635 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6131    1.2283    0.2144 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.9798    1.6082    1.6562 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7233    2.3110   -0.3035 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3221    2.1303    0.2740 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6931    0.8662   -0.2789 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7476    0.9856   -1.8028 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7063   -0.7721    0.3603 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6663   -1.3158    1.7989 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2506   -1.9397   -0.4784 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6433   -2.2701   -0.0264 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5279   -1.1164   -0.2925 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.4643   -0.9857    0.7546 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0600   -0.5333   -2.5956 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1825    1.2274   -2.5065 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5759    0.5053   -2.3784 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2404    0.9237    0.8167 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3869    2.2464   -0.1385 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6931    1.1749   -0.8878 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0363    0.5818    1.2613 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5720    2.1668   -1.0556 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0576    2.4828    0.5994 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4494    1.3937   -1.7246 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1320    2.6770   -0.5495 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1403    0.7126    2.3082 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4931    2.3144    1.5792 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8624    1.2795    1.9830 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2574   -0.7629   -1.1696 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7442   -2.2244    0.7932 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3824   -0.6693    1.1069 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8026   -0.3726   -1.8923 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1674   -1.8692   -1.1783 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2271   -2.9974   -1.6268 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7717   -2.5106   -0.8982 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1302   -1.6072   -2.3696 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7189   -3.4940    0.1944 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6479    0.1470   -0.9967 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2517    0.1455    0.7383 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7788    1.4344   -1.6334 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4641    2.1775   -0.1701 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9667    1.1836    1.9332 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0186    2.7340    1.6939 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2434    1.2011    2.3766 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0929    3.2790    0.1477 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7337    2.4608   -1.3811 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4956    1.9340    1.3705 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7696    3.0418    0.0723 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4509    2.0358   -2.0833 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7647    0.8540   -2.1727 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1178    0.2277   -2.3014 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8838   -2.3755    1.8693 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4730   -0.7533    2.3556 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7349   -1.0897    2.3125 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6450   -2.8579   -0.3471 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2604   -1.7176   -1.5441 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7265   -2.5640    1.0245 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9526   -3.1832   -0.6165 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1614   -1.3721   -1.1930 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3110   -1.4199    0.5632 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  1
  7  9  1  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 16 18  1  1
 18 19  2  0
 18 20  1  0
 16 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  1
 23 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  6
  9 29  1  0
 29 30  1  1
 29 31  1  0
 31 32  1  0
 32 33  1  0
 33 34  1  0
 33  2  1  0
 29  4  1  0
 27  7  1  0
 27 13  1  0
 23 14  1  0
  1 35  1  0
  1 36  1  0
  1 37  1  0
  3 38  1  0
  3 39  1  0
  3 40  1  0
  4 41  1  0
  5 42  1  0
  5 43  1  0
  6 44  1  0
  6 45  1  0
  8 46  1  0
  8 47  1  0
  8 48  1  0
  9 49  1  0
 12 50  1  0
 14 51  1  0
 15 52  1  0
 15 53  1  0
 17 54  1  0
 17 55  1  0
 17 56  1  0
 20 57  1  0
 21 58  1  0
 21 59  1  0
 22 60  1  0
 22 61  1  0
 24 62  1  0
 24 63  1  0
 24 64  1  0
 25 65  1  0
 25 66  1  0
 26 67  1  0
 26 68  1  0
 28 69  1  0
 28 70  1  0
 28 71  1  0
 30 72  1  0
 30 73  1  0
 30 74  1  0
 31 75  1  0
 31 76  1  0
 32 77  1  0
 32 78  1  0
 33 79  1  6
 34 80  1  0
M  END

HEADER    PROTEIN                                 20-APR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-APR-20         0                                  
HETATM    1  C   UNK     0      16.052 -36.741   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      15.281 -35.408   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      16.614 -34.637   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      17.948 -35.405   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      19.281 -34.634   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      19.279 -33.094   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      17.945 -32.325   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      16.612 -33.097   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      15.278 -32.328   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      13.945 -33.099   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      13.946 -34.639   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      12.613 -35.411   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      16.611 -31.557   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      17.944 -30.785   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      16.609 -30.017   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      19.277 -30.014   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      20.611 -30.783   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      20.612 -32.323   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      21.947 -33.092   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      23.280 -32.320   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      23.278 -30.780   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      21.944 -30.012   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      21.942 -28.472   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      23.275 -27.700   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      24.610 -28.469   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      24.611 -30.009   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      22.504 -26.367   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      24.044 -26.366   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      23.273 -25.033   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0      25.584 -26.364   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      24.613 -31.549   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      21.784 -31.580   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      20.614 -33.863   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      14.512 -36.742   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   11   34                                             
CONECT    3    2    4    8                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   18   33                                             
CONECT    7    6    8   14                                                  
CONECT    8    3    7    9   13                                             
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11    2   10   12                                                  
CONECT   12   11                                                            
CONECT   13    8                                                            
CONECT   14    7   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17                                                       
CONECT   17   16   18   22                                                  
CONECT   18    6   17   19   32                                             
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22   26   31                                             
CONECT   22   17   21   23                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25   27   28                                             
CONECT   25   24   26                                                       
CONECT   26   21   25                                                       
CONECT   27   24                                                            
CONECT   28   24   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28                                                            
CONECT   31   21                                                            
CONECT   32   18                                                            
CONECT   33    6                                                            
CONECT   34    2                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   76    0
END

COMPND    HMDB0011628
HETATM    1  C1  UNL     1       4.606   0.358  -2.069  1.00  0.00           C  
HETATM    2  C2  UNL     1       4.841   0.167  -0.612  1.00  0.00           C  
HETATM    3  C3  UNL     1       5.838   1.260  -0.183  1.00  0.00           C  
HETATM    4  C4  UNL     1       3.579   0.400   0.235  1.00  0.00           C  
HETATM    5  C5  UNL     1       2.995   1.687  -0.205  1.00  0.00           C  
HETATM    6  C6  UNL     1       1.577   1.666  -0.659  1.00  0.00           C  
HETATM    7  C7  UNL     1       0.703   0.737   0.196  1.00  0.00           C  
HETATM    8  C8  UNL     1       0.815   1.229   1.601  1.00  0.00           C  
HETATM    9  C9  UNL     1       1.272  -0.621  -0.046  1.00  0.00           C  
HETATM   10  C10 UNL     1       0.384  -1.641   0.502  1.00  0.00           C  
HETATM   11  O1  UNL     1       0.755  -2.747   1.003  1.00  0.00           O  
HETATM   12  C11 UNL     1      -1.059  -1.411   0.492  1.00  0.00           C  
HETATM   13  C12 UNL     1      -1.584  -0.250   0.132  1.00  0.00           C  
HETATM   14  C13 UNL     1      -3.057  -0.137   0.162  1.00  0.00           C  
HETATM   15  C14 UNL     1      -3.715  -0.940  -0.961  1.00  0.00           C  
HETATM   16  C15 UNL     1      -5.136  -1.229  -0.460  1.00  0.00           C  
HETATM   17  C16 UNL     1      -5.875  -2.123  -1.424  1.00  0.00           C  
HETATM   18  C17 UNL     1      -5.036  -1.963   0.828  1.00  0.00           C  
HETATM   19  O2  UNL     1      -5.524  -1.508   1.881  1.00  0.00           O  
HETATM   20  O3  UNL     1      -4.389  -3.196   0.912  1.00  0.00           O  
HETATM   21  C18 UNL     1      -5.802   0.089  -0.252  1.00  0.00           C  
HETATM   22  C19 UNL     1      -4.915   1.273  -0.564  1.00  0.00           C  
HETATM   23  C20 UNL     1      -3.613   1.228   0.214  1.00  0.00           C  
HETATM   24  C21 UNL     1      -3.980   1.608   1.656  1.00  0.00           C  
HETATM   25  C22 UNL     1      -2.723   2.311  -0.303  1.00  0.00           C  
HETATM   26  C23 UNL     1      -1.322   2.130   0.274  1.00  0.00           C  
HETATM   27  C24 UNL     1      -0.693   0.866  -0.279  1.00  0.00           C  
HETATM   28  C25 UNL     1      -0.748   0.986  -1.803  1.00  0.00           C  
HETATM   29  C26 UNL     1       2.706  -0.772   0.360  1.00  0.00           C  
HETATM   30  C27 UNL     1       2.666  -1.316   1.799  1.00  0.00           C  
HETATM   31  C28 UNL     1       3.251  -1.940  -0.478  1.00  0.00           C  
HETATM   32  C29 UNL     1       4.643  -2.270  -0.026  1.00  0.00           C  
HETATM   33  C30 UNL     1       5.528  -1.116  -0.292  1.00  0.00           C  
HETATM   34  O4  UNL     1       6.464  -0.986   0.755  1.00  0.00           O  
HETATM   35  H1  UNL     1       5.060  -0.533  -2.596  1.00  0.00           H  
HETATM   36  H2  UNL     1       5.183   1.227  -2.507  1.00  0.00           H  
HETATM   37  H3  UNL     1       3.576   0.505  -2.378  1.00  0.00           H  
HETATM   38  H4  UNL     1       6.240   0.924   0.817  1.00  0.00           H  
HETATM   39  H5  UNL     1       5.387   2.246  -0.138  1.00  0.00           H  
HETATM   40  H6  UNL     1       6.693   1.175  -0.888  1.00  0.00           H  
HETATM   41  H7  UNL     1       4.036   0.582   1.261  1.00  0.00           H  
HETATM   42  H8  UNL     1       3.572   2.167  -1.056  1.00  0.00           H  
HETATM   43  H9  UNL     1       3.058   2.483   0.599  1.00  0.00           H  
HETATM   44  H10 UNL     1       1.449   1.394  -1.725  1.00  0.00           H  
HETATM   45  H11 UNL     1       1.132   2.677  -0.550  1.00  0.00           H  
HETATM   46  H12 UNL     1       0.140   0.713   2.308  1.00  0.00           H  
HETATM   47  H13 UNL     1       0.493   2.314   1.579  1.00  0.00           H  
HETATM   48  H14 UNL     1       1.862   1.280   1.983  1.00  0.00           H  
HETATM   49  H15 UNL     1       1.257  -0.763  -1.170  1.00  0.00           H  
HETATM   50  H16 UNL     1      -1.744  -2.224   0.793  1.00  0.00           H  
HETATM   51  H17 UNL     1      -3.382  -0.669   1.107  1.00  0.00           H  
HETATM   52  H18 UNL     1      -3.803  -0.373  -1.892  1.00  0.00           H  
HETATM   53  H19 UNL     1      -3.167  -1.869  -1.178  1.00  0.00           H  
HETATM   54  H20 UNL     1      -5.227  -2.997  -1.627  1.00  0.00           H  
HETATM   55  H21 UNL     1      -6.772  -2.511  -0.898  1.00  0.00           H  
HETATM   56  H22 UNL     1      -6.130  -1.607  -2.370  1.00  0.00           H  
HETATM   57  H23 UNL     1      -3.719  -3.494   0.194  1.00  0.00           H  
HETATM   58  H24 UNL     1      -6.648   0.147  -0.997  1.00  0.00           H  
HETATM   59  H25 UNL     1      -6.252   0.146   0.738  1.00  0.00           H  
HETATM   60  H26 UNL     1      -4.779   1.434  -1.633  1.00  0.00           H  
HETATM   61  H27 UNL     1      -5.464   2.177  -0.170  1.00  0.00           H  
HETATM   62  H28 UNL     1      -4.967   1.184   1.933  1.00  0.00           H  
HETATM   63  H29 UNL     1      -4.019   2.734   1.694  1.00  0.00           H  
HETATM   64  H30 UNL     1      -3.243   1.201   2.377  1.00  0.00           H  
HETATM   65  H31 UNL     1      -3.093   3.279   0.148  1.00  0.00           H  
HETATM   66  H32 UNL     1      -2.734   2.461  -1.381  1.00  0.00           H  
HETATM   67  H33 UNL     1      -1.496   1.934   1.371  1.00  0.00           H  
HETATM   68  H34 UNL     1      -0.770   3.042   0.072  1.00  0.00           H  
HETATM   69  H35 UNL     1      -0.451   2.036  -2.083  1.00  0.00           H  
HETATM   70  H36 UNL     1      -1.765   0.854  -2.173  1.00  0.00           H  
HETATM   71  H37 UNL     1      -0.118   0.228  -2.301  1.00  0.00           H  
HETATM   72  H38 UNL     1       2.884  -2.375   1.869  1.00  0.00           H  
HETATM   73  H39 UNL     1       3.473  -0.753   2.356  1.00  0.00           H  
HETATM   74  H40 UNL     1       1.735  -1.090   2.313  1.00  0.00           H  
HETATM   75  H41 UNL     1       2.645  -2.858  -0.347  1.00  0.00           H  
HETATM   76  H42 UNL     1       3.260  -1.718  -1.544  1.00  0.00           H  
HETATM   77  H43 UNL     1       4.727  -2.564   1.025  1.00  0.00           H  
HETATM   78  H44 UNL     1       4.953  -3.183  -0.616  1.00  0.00           H  
HETATM   79  H45 UNL     1       6.161  -1.372  -1.193  1.00  0.00           H  
HETATM   80  H46 UNL     1       7.311  -1.420   0.563  1.00  0.00           H  
CONECT    1    2   35   36   37
CONECT    2    3    4   33
CONECT    3   38   39   40
CONECT    4    5   29   41
CONECT    5    6   42   43
CONECT    6    7   44   45
CONECT    7    8    9   27
CONECT    8   46   47   48
CONECT    9   10   29   49
CONECT   10   11   11   12
CONECT   12   13   13   50
CONECT   13   14   27
CONECT   14   15   23   51
CONECT   15   16   52   53
CONECT   16   17   18   21
CONECT   17   54   55   56
CONECT   18   19   19   20
CONECT   20   57
CONECT   21   22   58   59
CONECT   22   23   60   61
CONECT   23   24   25
CONECT   24   62   63   64
CONECT   25   26   65   66
CONECT   26   27   67   68
CONECT   27   28
CONECT   28   69   70   71
CONECT   29   30   31
CONECT   30   72   73   74
CONECT   31   32   75   76
CONECT   32   33   77   78
CONECT   33   34   79
CONECT   34   80
END

HMDB0011628
     RDKit          3D
Glycyrrhetinic acid
 80 84  0  0  0  0  0  0  0  0999 V2000
    4.6063    0.3583   -2.0694 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8407    0.1672   -0.6120 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8375    1.2605   -0.1825 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5793    0.4002    0.2346 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9953    1.6867   -0.2050 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5775    1.6663   -0.6588 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7025    0.7366    0.1956 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8145    1.2294    1.6007 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2719   -0.6210   -0.0458 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3836   -1.6411    0.5020 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7550   -2.7472    1.0033 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0588   -1.4108    0.4923 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5844   -0.2498    0.1320 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0571   -0.1367    0.1624 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7150   -0.9401   -0.9612 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1360   -1.2294   -0.4595 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.8746   -2.1235   -1.4244 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0358   -1.9628    0.8283 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5237   -1.5078    1.8815 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3888   -3.1956    0.9115 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8020    0.0889   -0.2522 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9146    1.2734   -0.5635 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6131    1.2283    0.2144 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.9798    1.6082    1.6562 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7233    2.3110   -0.3035 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3221    2.1303    0.2740 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6931    0.8662   -0.2789 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7476    0.9856   -1.8028 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7063   -0.7721    0.3603 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6663   -1.3158    1.7989 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2506   -1.9397   -0.4784 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6433   -2.2701   -0.0264 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5279   -1.1164   -0.2925 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.4643   -0.9857    0.7546 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0600   -0.5333   -2.5956 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1825    1.2274   -2.5065 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5759    0.5053   -2.3784 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2404    0.9237    0.8167 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3869    2.2464   -0.1385 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6931    1.1749   -0.8878 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0363    0.5818    1.2613 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5720    2.1668   -1.0556 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0576    2.4828    0.5994 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4494    1.3937   -1.7246 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1320    2.6770   -0.5495 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1403    0.7126    2.3082 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4931    2.3144    1.5792 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8624    1.2795    1.9830 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2574   -0.7629   -1.1696 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7442   -2.2244    0.7932 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3824   -0.6693    1.1069 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8026   -0.3726   -1.8923 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1674   -1.8692   -1.1783 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2271   -2.9974   -1.6268 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7717   -2.5106   -0.8982 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1302   -1.6072   -2.3696 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7189   -3.4940    0.1944 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6479    0.1470   -0.9967 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2517    0.1455    0.7383 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7788    1.4344   -1.6334 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4641    2.1775   -0.1701 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9667    1.1836    1.9332 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0186    2.7340    1.6939 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2434    1.2011    2.3766 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0929    3.2790    0.1477 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7337    2.4608   -1.3811 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4956    1.9340    1.3705 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7696    3.0418    0.0723 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4509    2.0358   -2.0833 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7647    0.8540   -2.1727 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1178    0.2277   -2.3014 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8838   -2.3755    1.8693 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4730   -0.7533    2.3556 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7349   -1.0897    2.3125 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6450   -2.8579   -0.3471 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2604   -1.7176   -1.5441 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7265   -2.5640    1.0245 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9526   -3.1832   -0.6165 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1614   -1.3721   -1.1930 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3110   -1.4199    0.5632 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  1
  7  9  1  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 16 18  1  1
 18 19  2  0
 18 20  1  0
 16 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  1
 23 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  6
  9 29  1  0
 29 30  1  1
 29 31  1  0
 31 32  1  0
 32 33  1  0
 33 34  1  0
 33  2  1  0
 29  4  1  0
 27  7  1  0
 27 13  1  0
 23 14  1  0
  1 35  1  0
  1 36  1  0
  1 37  1  0
  3 38  1  0
  3 39  1  0
  3 40  1  0
  4 41  1  0
  5 42  1  0
  5 43  1  0
  6 44  1  0
  6 45  1  0
  8 46  1  0
  8 47  1  0
  8 48  1  0
  9 49  1  0
 12 50  1  0
 14 51  1  0
 15 52  1  0
 15 53  1  0
 17 54  1  0
 17 55  1  0
 17 56  1  0
 20 57  1  0
 21 58  1  0
 21 59  1  0
 22 60  1  0
 22 61  1  0
 24 62  1  0
 24 63  1  0
 24 64  1  0
 25 65  1  0
 25 66  1  0
 26 67  1  0
 26 68  1  0
 28 69  1  0
 28 70  1  0
 28 71  1  0
 30 72  1  0
 30 73  1  0
 30 74  1  0
 31 75  1  0
 31 76  1  0
 32 77  1  0
 32 78  1  0
 33 79  1  6
 34 80  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Value	Source
Glycyrrhetinate	Generator
18b-Glycyrrhetic acid	HMDB
18b-Glycyrrhetinic acid	HMDB
18b-Glycyrrhtinic acid	HMDB
3-Glycyrrhetinic acid	HMDB
3-Hydroxy-11-oxoolean-12-en-29-Oate	HMDB
3-Hydroxy-11-oxoolean-12-en-29-Oic acid	HMDB
3-Hydroxy-11-oxoolean-12-en-29-Oic acid (acd/name 4.0)	HMDB
3b-Hydroxy-11-oxo-olean-12-en-30-Oate	HMDB
3b-Hydroxy-11-oxo-olean-12-en-30-Oic acid	HMDB
3b-Hydroxy-11-oxoolean-12-en-30-Oate	HMDB
3b-Hydroxy-11-oxoolean-12-en-30-Oic acid	HMDB
a-Glycyrrhetinic acid	HMDB
alpha-Glycyrrhetinic acid	HMDB
b-Glycyrrhetic acid	HMDB
beta-Glycyrrhetic acid	HMDB
Biosone	HMDB
Enoxolone	HMDB
Glycyrrhetic acid	HMDB
Glycyrrhetin	HMDB
Uralenic acid	HMDB
Acid, glycyrrhetinic	HMDB
Dexo brand OF glycyrrhetinic acid	HMDB
Po 12	HMDB
Rhetinic acid	HMDB
Acid, glycyrrhetic	HMDB
Plantes et médecines brand OF glycyrrhetinic acid	HMDB
Acid, rhetinic	HMDB
Acid, uralenic	HMDB
Arthrodont	HMDB
Glyciram	HMDB
Glycyram	HMDB
Jintan	HMDB
(2S,4AS,6as,6BR,10S,12as)-10-hydroxy-2,4a,6a,6b,9,9,12a-heptamethyl-13-oxo-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicene-2-carboxylate	HMDB
12, Po	HMDB
Glycyrrhetinic acid	HMDB, MeSH

Chemical Formula

C₃₀H₄₆O₄

Average Mass

470.6838 Da

Monoisotopic Mass

470.33961 Da

IUPAC Name

(2S,4aS,6aS,6bR,10S,12aS)-10-hydroxy-2,4a,6a,6b,9,9,12a-heptamethyl-13-oxo-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicene-2-carboxylic acid

Traditional Name

(2S,4aS,6aS,6bR,10S,12aS)-10-hydroxy-2,4a,6a,6b,9,9,12a-heptamethyl-13-oxo-3,4,5,6,7,8,8a,10,11,12,12b,14b-dodecahydro-1H-picene-2-carboxylic acid

CAS Registry Number

471-53-4

SMILES

CC1(C)[C@@H](O)CC[C@@]2(C)C1CC[C@]1(C)C2C(=O)C=C2C3C[C@](C)(CC[C@]3(C)CC[C@@]12C)C(O)=O

InChI Identifier

InChI=1S/C30H46O4/c1-25(2)21-8-11-30(7)23(28(21,5)10-9-22(25)32)20(31)16-18-19-17-27(4,24(33)34)13-12-26(19,3)14-15-29(18,30)6/h16,19,21-23,32H,8-15,17H2,1-7H3,(H,33,34)/t19?,21?,22-,23?,26+,27-,28-,29+,30+/m0/s1

InChI Key

MPDGHEJMBKOTSU-WFJWTYAKSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, 100%_DMSO, experimental)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

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	¹³C NMR Spectrum (1D, 252 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	¹³C NMR Spectrum (1D, 75 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	¹³C NMR Spectrum (1D, 126 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	¹³C NMR Spectrum (1D, 176 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	¹³C NMR Spectrum (1D, 226 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
Echinopora lamellosa	LOTUS Database	35616633
Glycyrrhiza aspera	KNApSAcK Database	22123792
Glycyrrhiza glabra	KNApSAcK Database	22123792
Glycyrrhiza inflata	KNApSAcK Database	22123792
Glycyrrhiza kansuensis	KNApSAcK Database	22123792
Glycyrrhiza radix	KNApSAcK Database	22123792
Glycyrrhiza uralensis	KNApSAcK Database	22123792
Glycyrrhiza yunnanensis	KNApSAcK Database	22123792

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Triterpenoids

Direct Parent

Triterpenoids

Alternative Parents

Substituents

Triterpenoid
Cyclohexenone
Cyclic alcohol
Secondary alcohol
Ketone
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	296 °C	Not Available
Boiling Point	588.34 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	0.011 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	5.498 (est)	The Good Scents Company Information System

Predicted Properties

Property	Value	Source
Water Solubility	0.0017 g/L	ALOGPS
logP	5.45	ALOGPS
logP	6.03	ChemAxon
logS	-5.4	ALOGPS
pKa (Strongest Acidic)	4.44	ChemAxon
pKa (Strongest Basic)	-0.84	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	74.6 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	134.27 m³·mol⁻¹	ChemAxon
Polarizability	55.39 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon