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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2009-01-30 10:07:36 UTC

Update Date

2022-03-07 02:51:12 UTC

HMDB ID

HMDB0011628

Secondary Accession Numbers

HMDB11628

Metabolite 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
 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


  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>
HMDB0011628

> <DATABASE_NAME>
hmdb

> <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 Stereo Labels

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 Molecular Weight

470.6838

Monoisotopic Molecular Weight

470.33960996

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

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

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 18850581)

Cellular substructure

Extracellular (HMDB: HMDB0011628)
Membrane (HMDB: HMDB0011628)

Source

Exogenous

Exogenous (HMDB: HMDB0011628)

Food

Animal origin

Poultry

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Endogenous

Endogenous (HMDB: HMDB0011628)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	296 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular 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

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	213.515	31661259
DarkChem	[M-H]-	203.101	31661259
DeepCCS	[M-2H]-	248.64	30932474
DeepCCS	[M+Na]+	223.223	30932474
AllCCS	[M+H]+	217.2	32859911
AllCCS	[M+H-H2O]+	215.6	32859911
AllCCS	[M+NH4]+	218.7	32859911
AllCCS	[M+Na]+	219.1	32859911
AllCCS	[M-H]-	213.7	32859911
AllCCS	[M+Na-2H]-	215.7	32859911
AllCCS	[M+HCOO]-	218.1	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	9.62 minutes	32390414
Predicted by Siyang on May 30, 2022	20.5308 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.42 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	3261.9 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	388.3 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	257.7 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	178.0 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	605.5 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	860.5 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	987.1 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	99.9 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1608.2 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	633.5 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1920.5 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	623.1 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	558.7 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	225.1 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	492.8 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	8.6 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Glycyrrhetinic acid	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	3768.1	Standard polar	33892256
Glycyrrhetinic acid	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	3512.6	Standard non polar	33892256
Glycyrrhetinic acid	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	3950.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Glycyrrhetinic acid,1TMS,isomer #1	CC1(C)C2CC[C@]3(C)C(C(=O)C=C4C5C[C@@](C)(C(=O)O)CC[C@]5(C)CC[C@]43C)[C@@]2(C)CC[C@@H]1O[Si](C)(C)C	4017.4	Semi standard non polar	33892256
Glycyrrhetinic acid,1TMS,isomer #2	CC1(C)C2CC[C@]3(C)C(C(=O)C=C4C5C[C@@](C)(C(=O)O[Si](C)(C)C)CC[C@]5(C)CC[C@]43C)[C@@]2(C)CC[C@@H]1O	3943.4	Semi standard non polar	33892256
Glycyrrhetinic acid,1TMS,isomer #3	CC1(C)C2CC[C@]3(C)C(=C(O[Si](C)(C)C)C=C4C5C[C@@](C)(C(=O)O)CC[C@]5(C)CC[C@]43C)[C@@]2(C)CC[C@@H]1O	3943.9	Semi standard non polar	33892256
Glycyrrhetinic acid,2TMS,isomer #1	CC1(C)C2CC[C@]3(C)C(C(=O)C=C4C5C[C@@](C)(C(=O)O[Si](C)(C)C)CC[C@]5(C)CC[C@]43C)[C@@]2(C)CC[C@@H]1O[Si](C)(C)C	3933.4	Semi standard non polar	33892256
Glycyrrhetinic acid,2TMS,isomer #2	CC1(C)C2CC[C@]3(C)C(=C(O[Si](C)(C)C)C=C4C5C[C@@](C)(C(=O)O)CC[C@]5(C)CC[C@]43C)[C@@]2(C)CC[C@@H]1O[Si](C)(C)C	3919.0	Semi standard non polar	33892256
Glycyrrhetinic acid,2TMS,isomer #3	CC1(C)C2CC[C@]3(C)C(=C(O[Si](C)(C)C)C=C4C5C[C@@](C)(C(=O)O[Si](C)(C)C)CC[C@]5(C)CC[C@]43C)[C@@]2(C)CC[C@@H]1O	3876.6	Semi standard non polar	33892256
Glycyrrhetinic acid,3TMS,isomer #1	CC1(C)C2CC[C@]3(C)C(=C(O[Si](C)(C)C)C=C4C5C[C@@](C)(C(=O)O[Si](C)(C)C)CC[C@]5(C)CC[C@]43C)[C@@]2(C)CC[C@@H]1O[Si](C)(C)C	3823.9	Semi standard non polar	33892256
Glycyrrhetinic acid,3TMS,isomer #1	CC1(C)C2CC[C@]3(C)C(=C(O[Si](C)(C)C)C=C4C5C[C@@](C)(C(=O)O[Si](C)(C)C)CC[C@]5(C)CC[C@]43C)[C@@]2(C)CC[C@@H]1O[Si](C)(C)C	3712.5	Standard non polar	33892256
Glycyrrhetinic acid,3TMS,isomer #1	CC1(C)C2CC[C@]3(C)C(=C(O[Si](C)(C)C)C=C4C5C[C@@](C)(C(=O)O[Si](C)(C)C)CC[C@]5(C)CC[C@]43C)[C@@]2(C)CC[C@@H]1O[Si](C)(C)C	3841.5	Standard polar	33892256
Glycyrrhetinic acid,1TBDMS,isomer #1	CC1(C)C2CC[C@]3(C)C(C(=O)C=C4C5C[C@@](C)(C(=O)O)CC[C@]5(C)CC[C@]43C)[C@@]2(C)CC[C@@H]1O[Si](C)(C)C(C)(C)C	4208.3	Semi standard non polar	33892256
Glycyrrhetinic acid,1TBDMS,isomer #2	CC1(C)C2CC[C@]3(C)C(C(=O)C=C4C5C[C@@](C)(C(=O)O[Si](C)(C)C(C)(C)C)CC[C@]5(C)CC[C@]43C)[C@@]2(C)CC[C@@H]1O	4175.5	Semi standard non polar	33892256
Glycyrrhetinic acid,1TBDMS,isomer #3	CC1(C)C2CC[C@]3(C)C(=C(O[Si](C)(C)C(C)(C)C)C=C4C5C[C@@](C)(C(=O)O)CC[C@]5(C)CC[C@]43C)[C@@]2(C)CC[C@@H]1O	4161.5	Semi standard non polar	33892256
Glycyrrhetinic acid,2TBDMS,isomer #1	CC1(C)C2CC[C@]3(C)C(C(=O)C=C4C5C[C@@](C)(C(=O)O[Si](C)(C)C(C)(C)C)CC[C@]5(C)CC[C@]43C)[C@@]2(C)CC[C@@H]1O[Si](C)(C)C(C)(C)C	4367.1	Semi standard non polar	33892256
Glycyrrhetinic acid,2TBDMS,isomer #2	CC1(C)C2CC[C@]3(C)C(=C(O[Si](C)(C)C(C)(C)C)C=C4C5C[C@@](C)(C(=O)O)CC[C@]5(C)CC[C@]43C)[C@@]2(C)CC[C@@H]1O[Si](C)(C)C(C)(C)C	4324.0	Semi standard non polar	33892256
Glycyrrhetinic acid,2TBDMS,isomer #3	CC1(C)C2CC[C@]3(C)C(=C(O[Si](C)(C)C(C)(C)C)C=C4C5C[C@@](C)(C(=O)O[Si](C)(C)C(C)(C)C)CC[C@]5(C)CC[C@]43C)[C@@]2(C)CC[C@@H]1O	4322.4	Semi standard non polar	33892256
Glycyrrhetinic acid,3TBDMS,isomer #1	CC1(C)C2CC[C@]3(C)C(=C(O[Si](C)(C)C(C)(C)C)C=C4C5C[C@@](C)(C(=O)O[Si](C)(C)C(C)(C)C)CC[C@]5(C)CC[C@]43C)[C@@]2(C)CC[C@@H]1O[Si](C)(C)C(C)(C)C	4435.3	Semi standard non polar	33892256
Glycyrrhetinic acid,3TBDMS,isomer #1	CC1(C)C2CC[C@]3(C)C(=C(O[Si](C)(C)C(C)(C)C)C=C4C5C[C@@](C)(C(=O)O[Si](C)(C)C(C)(C)C)CC[C@]5(C)CC[C@]43C)[C@@]2(C)CC[C@@H]1O[Si](C)(C)C(C)(C)C	4428.0	Standard non polar	33892256
Glycyrrhetinic acid,3TBDMS,isomer #1	CC1(C)C2CC[C@]3(C)C(=C(O[Si](C)(C)C(C)(C)C)C=C4C5C[C@@](C)(C(=O)O[Si](C)(C)C(C)(C)C)CC[C@]5(C)CC[C@]43C)[C@@]2(C)CC[C@@H]1O[Si](C)(C)C(C)(C)C	4085.4	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Glycyrrhetinic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4l-0217900000-aadc516f5cfd224a8c71	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Glycyrrhetinic acid GC-MS (2 TMS) - 70eV, Positive	splash10-0f6t-0000192000-c460e8d231076de78a05	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Glycyrrhetinic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Glycyrrhetinic acid ESI-TOF 10V, Negative-QTOF	splash10-0a4i-0000930000-25139768b4507e334b4a	2018-05-25	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Glycyrrhetinic acid ESI-TOF 20V, Negative-QTOF	splash10-0a4i-0000930000-25139768b4507e334b4a	2018-05-25	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Glycyrrhetinic acid ESI-TOF 50V, Negative-QTOF	splash10-00or-0000900000-ada4fdd603d1852beae8	2018-05-25	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Glycyrrhetinic acid ESI-TOF 40V, Negative-QTOF	splash10-014i-0000900000-276dcd237f3df1b55bf7	2018-05-25	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Glycyrrhetinic acid ESI-TOF , Negative-QTOF	splash10-014i-0000911000-952bbb171fba142dba69	2018-05-25	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Glycyrrhetinic acid ESI-TOF 10V, Negative-QTOF	splash10-014u-0000700009-50048523dd30a3c69126	2018-05-25	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Glycyrrhetinic acid ESI-TOF 30V, Negative-QTOF	splash10-014u-0000700009-50048523dd30a3c69126	2018-05-25	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Glycyrrhetinic acid ESI-TOF 10V, Negative-QTOF	splash10-014i-0000900000-125f02720b2a01ba256e	2018-05-25	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Glycyrrhetinic acid ESI-TOF 20V, Negative-QTOF	splash10-014i-0000900000-6466c540accc2a7ad380	2018-05-25	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Glycyrrhetinic acid ESI-TOF 50V, Negative-QTOF	splash10-00or-0000900000-ada4fdd603d1852beae8	2018-05-25	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Glycyrrhetinic acid ESI-TOF 40V, Negative-QTOF	splash10-014i-0000900000-276dcd237f3df1b55bf7	2018-05-25	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Glycyrrhetinic acid ESI-TOF , Negative-QTOF	splash10-014i-0000911000-952bbb171fba142dba69	2018-05-25	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Glycyrrhetinic acid ESI-TOF 10V, Negative-QTOF	splash10-014u-0000700009-50048523dd30a3c69126	2018-05-25	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Glycyrrhetinic acid ESI-TOF 30V, Negative-QTOF	splash10-014i-0000900000-c50958d1a751bbfbca79	2018-05-25	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Glycyrrhetinic acid LC-ESI-qTof , Positive-QTOF	splash10-03dj-9781100000-4553bbbe9a30a0391bb4	2018-05-25	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Glycyrrhetinic acid LC-ESI-QFT , negative-QTOF	splash10-014i-0000900000-027d29bdfec0cb682eab	2018-05-25	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Glycyrrhetinic acid LC-ESI-QFT , negative-QTOF	splash10-014i-0000900000-7d4a004adc92eda07905	2018-05-25	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Glycyrrhetinic acid LC-ESI-QFT , negative-QTOF	splash10-014i-0000900000-04e795c32f4f79f139f3	2018-05-25	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Glycyrrhetinic acid LC-ESI-QFT , negative-QTOF	splash10-0a6r-0004900000-5d9468128c8fc0642c7d	2018-05-25	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Glycyrrhetinic acid 10V, Positive-QTOF	splash10-0udi-0000900000-9677a3bedc1d92d76314	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Glycyrrhetinic acid 20V, Positive-QTOF	splash10-0pdr-0001900000-29bf26f4b3b6b73752a8	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Glycyrrhetinic acid 40V, Positive-QTOF	splash10-0ar0-1609800000-2dedffb68814f07143d4	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Glycyrrhetinic acid 10V, Negative-QTOF	splash10-014i-0000900000-612624a459b00afd684c	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Glycyrrhetinic acid 20V, Negative-QTOF	splash10-0kxr-0000900000-6cf44557b5b0900d64ee	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Glycyrrhetinic acid 40V, Negative-QTOF	splash10-0pb9-1001900000-918ef5666b6581adc583	2017-09-01	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Experimental 2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, 100%_DMSO, experimental)	2012-12-05	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.104 +/- 0.008 uM	Adult (>18 years old)	Both	Normal	18850581	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Enoxolone

METLIN ID

Not Available

PubChem Compound

18526330

PDB ID

Not Available

ChEBI ID

30853

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
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Enzymes

Enzyme Details

1. Corticosteroid 11-beta-dehydrogenase isozyme 2

General function:: Involved in oxidoreductase activity
Specific function:: Catalyzes the conversion of cortisol to the inactive metabolite cortisone. Modulates intracellular glucocorticoid levels, thus protecting the nonselective mineralocorticoid receptor from occupation by glucocorticoids.
Gene Name:: HSD11B2
Uniprot ID:: P80365
Molecular weight:: 44126.06

Showing metabocard for Glycyrrhetinic acid (HMDB0011628)

MOL for HMDB0011628 (Glycyrrhetinic acid)

3D MOL for HMDB0011628 (Glycyrrhetinic acid)

3D SDF for HMDB0011628 (Glycyrrhetinic acid)

3D-SDF for HMDB0011628 (Glycyrrhetinic acid)

PDB for HMDB0011628 (Glycyrrhetinic acid)

3D PDB for HMDB0011628 (Glycyrrhetinic acid)

SMILES for HMDB0011628 (Glycyrrhetinic acid)

INCHI for HMDB0011628 (Glycyrrhetinic acid)

Structure for HMDB0011628 (Glycyrrhetinic acid)

3D Structure for HMDB0011628 (Glycyrrhetinic acid)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

Enzymes