MiMeDB: Showing metabocard for Glycyrrhyzin (MMDBc0033646)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-19 04:57:17 UTC

Update Date

2022-08-31 22:37:23 UTC

Metabolite ID

MMDBc0033646

Metabolite Identification

Common Name

Glycyrrhyzin

Description

Glycyrrhizic acid, also known as glycyrrhizin, belongs to the class of organic compounds known as triterpene saponins. These are glycosylated derivatives of triterpene sapogenins. The sapogenin moiety backbone is usually based on the oleanane, ursane, taraxastane, bauerane, lanostane, lupeol, lupane, dammarane, cycloartane, friedelane, hopane, 9b,19-cyclo-lanostane, cycloartane, or cycloartanol skeleton. Glycyrrhizic acid is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI

ChEBI
  Mrv1572001071617152D          

 61 67  0  0  1  0            999 V2000
    9.5939  -14.6336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8793  -15.0459    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8793  -15.8704    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    9.5939  -16.2826    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   10.3085  -15.8704    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   11.0689  -16.2826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7834  -15.8704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7834  -15.0459    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   11.0689  -14.6336    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.3085  -15.0459    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   11.0689  -13.8091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7834  -13.3969    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5438  -13.8091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5438  -14.6336    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   13.2584  -15.0459    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9730  -14.6336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9730  -13.8091    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   13.2584  -13.3969    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   13.2584  -12.5724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9730  -12.1601    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   14.7333  -12.5724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7333  -13.3969    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0717  -16.9698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0520  -16.9606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3085  -14.2214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7918  -14.2672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5522  -15.4948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9821  -12.9846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4874  -11.4913    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4585  -11.5005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3085  -16.5392    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.0689  -15.3024    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.2584  -14.0657    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   14.0731  -10.7044    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.1829  -11.4128    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.3581  -13.4356    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1464  -16.2848    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4306  -16.6981    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.7149  -16.2849    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.4306  -17.5245    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9992  -16.6982    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.7149  -17.9378    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.9992  -17.5245    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.7149  -15.4584    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2835  -16.2849    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2835  -17.9378    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7149  -18.7642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9992  -19.1774    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7149  -14.6320    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.9991  -14.2188    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.4306  -14.2187    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9991  -13.3923    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.4305  -13.3923    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.7148  -12.9791    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.2834  -14.6320    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2834  -12.9791    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7148  -12.1527    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1462  -12.9791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1462  -12.1526    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4344  -19.0214    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.7301  -13.4712    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1 10  1  0  0  0  0
  9 10  1  0  0  0  0
  5 10  1  0  0  0  0
 10 25  1  1  0  0  0
  4  5  1  0  0  0  0
  6  5  1  0  0  0  0
  5 31  1  6  0  0  0
  2  1  1  0  0  0  0
  3  4  1  0  0  0  0
  4 23  1  6  0  0  0
  4 24  1  1  0  0  0
  3  2  1  0  0  0  0
 11  9  1  0  0  0  0
  8  9  1  0  0  0  0
  9 32  1  6  0  0  0
  7  8  1  0  0  0  0
 14  8  1  0  0  0  0
  8 26  1  1  0  0  0
  7  6  1  0  0  0  0
 12 11  1  0  0  0  0
 13 12  2  0  0  0  0
 15 14  1  0  0  0  0
 13 14  1  0  0  0  0
 14 27  1  6  0  0  0
 18 13  1  0  0  0  0
 16 15  1  0  0  0  0
 17 16  1  0  0  0  0
 19 18  1  0  0  0  0
 17 18  1  0  0  0  0
 18 33  1  1  0  0  0
 22 17  1  0  0  0  0
 17 28  1  1  0  0  0
 20 19  1  0  0  0  0
 21 20  1  0  0  0  0
 20 30  1  1  0  0  0
 20 29  1  6  0  0  0
 21 22  1  0  0  0  0
 34 30  2  0  0  0  0
 35 30  1  0  0  0  0
 36 11  2  0  0  0  0
  3 37  1  1  0  0  0
 38 39  1  0  0  0  0
 38 40  1  0  0  0  0
 39 41  1  0  0  0  0
 40 42  1  0  0  0  0
 41 43  1  0  0  0  0
 42 43  1  0  0  0  0
 38 37  1  1  0  0  0
 39 44  1  1  0  0  0
 41 45  1  6  0  0  0
 43 46  1  1  0  0  0
 42 47  1  6  0  0  0
 48 47  1  0  0  0  0
 49 50  1  0  0  0  0
 49 51  1  0  0  0  0
 50 52  1  0  0  0  0
 51 53  1  0  0  0  0
 52 54  1  0  0  0  0
 53 54  1  0  0  0  0
 49 44  1  1  0  0  0
 50 55  1  6  0  0  0
 52 56  1  1  0  0  0
 54 57  1  6  0  0  0
 53 58  1  1  0  0  0
 59 58  1  0  0  0  0
 60 47  2  0  0  0  0
 61 58  2  0  0  0  0
M  END

ChEBI
  Mrv1572001071617152D          

 61 67  0  0  1  0            999 V2000
    9.5939  -14.6336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8793  -15.0459    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8793  -15.8704    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    9.5939  -16.2826    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   10.3085  -15.8704    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   11.0689  -16.2826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7834  -15.8704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7834  -15.0459    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   11.0689  -14.6336    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.3085  -15.0459    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   11.0689  -13.8091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7834  -13.3969    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5438  -13.8091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5438  -14.6336    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   13.2584  -15.0459    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9730  -14.6336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9730  -13.8091    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   13.2584  -13.3969    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   13.2584  -12.5724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9730  -12.1601    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   14.7333  -12.5724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7333  -13.3969    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0717  -16.9698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0520  -16.9606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3085  -14.2214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7918  -14.2672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5522  -15.4948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9821  -12.9846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4874  -11.4913    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4585  -11.5005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3085  -16.5392    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.0689  -15.3024    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.2584  -14.0657    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   14.0731  -10.7044    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.1829  -11.4128    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.3581  -13.4356    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1464  -16.2848    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4306  -16.6981    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.7149  -16.2849    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.4306  -17.5245    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9992  -16.6982    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.7149  -17.9378    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.9992  -17.5245    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.7149  -15.4584    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2835  -16.2849    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2835  -17.9378    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7149  -18.7642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9992  -19.1774    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7149  -14.6320    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.9991  -14.2188    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.4306  -14.2187    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9991  -13.3923    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.4305  -13.3923    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.7148  -12.9791    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.2834  -14.6320    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2834  -12.9791    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7148  -12.1527    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1462  -12.9791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1462  -12.1526    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4344  -19.0214    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.7301  -13.4712    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1 10  1  0  0  0  0
  9 10  1  0  0  0  0
  5 10  1  0  0  0  0
 10 25  1  1  0  0  0
  4  5  1  0  0  0  0
  6  5  1  0  0  0  0
  5 31  1  6  0  0  0
  2  1  1  0  0  0  0
  3  4  1  0  0  0  0
  4 23  1  6  0  0  0
  4 24  1  1  0  0  0
  3  2  1  0  0  0  0
 11  9  1  0  0  0  0
  8  9  1  0  0  0  0
  9 32  1  6  0  0  0
  7  8  1  0  0  0  0
 14  8  1  0  0  0  0
  8 26  1  1  0  0  0
  7  6  1  0  0  0  0
 12 11  1  0  0  0  0
 13 12  2  0  0  0  0
 15 14  1  0  0  0  0
 13 14  1  0  0  0  0
 14 27  1  6  0  0  0
 18 13  1  0  0  0  0
 16 15  1  0  0  0  0
 17 16  1  0  0  0  0
 19 18  1  0  0  0  0
 17 18  1  0  0  0  0
 18 33  1  1  0  0  0
 22 17  1  0  0  0  0
 17 28  1  1  0  0  0
 20 19  1  0  0  0  0
 21 20  1  0  0  0  0
 20 30  1  1  0  0  0
 20 29  1  6  0  0  0
 21 22  1  0  0  0  0
 34 30  2  0  0  0  0
 35 30  1  0  0  0  0
 36 11  2  0  0  0  0
  3 37  1  1  0  0  0
 38 39  1  0  0  0  0
 38 40  1  0  0  0  0
 39 41  1  0  0  0  0
 40 42  1  0  0  0  0
 41 43  1  0  0  0  0
 42 43  1  0  0  0  0
 38 37  1  1  0  0  0
 39 44  1  1  0  0  0
 41 45  1  6  0  0  0
 43 46  1  1  0  0  0
 42 47  1  6  0  0  0
 48 47  1  0  0  0  0
 49 50  1  0  0  0  0
 49 51  1  0  0  0  0
 50 52  1  0  0  0  0
 51 53  1  0  0  0  0
 52 54  1  0  0  0  0
 53 54  1  0  0  0  0
 49 44  1  1  0  0  0
 50 55  1  6  0  0  0
 52 56  1  1  0  0  0
 54 57  1  6  0  0  0
 53 58  1  1  0  0  0
 59 58  1  0  0  0  0
 60 47  2  0  0  0  0
 61 58  2  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0033646

> <DATABASE_NAME>
MIME

> <SMILES>
[H][C@@]12C[C@](C)(CC[C@]1(C)CC[C@]1(C)C2=CC(=O)[C@]2([H])[C@@]3(C)CC[C@H](O[C@H]4O[C@@H]([C@@H](O)[C@H](O)[C@H]4O[C@@H]4O[C@@H]([C@@H](O)[C@H](O)[C@H]4O)C(O)=O)C(O)=O)C(C)(C)[C@]3([H])CC[C@@]12C)C(O)=O

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

> <INCHI_KEY>
LPLVUJXQOOQHMX-QWBHMCJMSA-N

> <FORMULA>
C42H62O16

> <MOLECULAR_WEIGHT>
822.942

> <EXACT_MASS>
822.403785916

> <JCHEM_ACCEPTOR_COUNT>
16

> <JCHEM_ATOM_COUNT>
120

> <JCHEM_AVERAGE_POLARIZABILITY>
86.35048797222835

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
8

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
2.78

> <JCHEM_LOGP>
3.1302058209999997

> <ALOGPS_LOGS>
-4.18

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-3

> <JCHEM_PKA>
3.5738490011649704

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.961005004154196

> <JCHEM_PKA_STRONGEST_BASIC>
-3.731980846359378

> <JCHEM_POLAR_SURFACE_AREA>
267.03999999999996

> <JCHEM_REFRACTIVITY>
198.82990000000012

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
5.45e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
glycyrrhizin

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 07-JAN-16   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: ChEBI                                             
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-JAN-16         0                                  
HETATM    1  C   UNK     0      17.909 -27.316   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      16.575 -28.086   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      16.575 -29.625   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      17.909 -30.394   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      19.242 -29.625   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      20.662 -30.394   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      21.996 -29.625   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      21.996 -28.086   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      20.662 -27.316   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      19.242 -28.086   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      20.662 -25.777   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      21.996 -25.007   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      23.415 -25.777   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      23.415 -27.316   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      24.749 -28.086   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      26.083 -27.316   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      26.083 -25.777   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      24.749 -25.007   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      24.749 -23.468   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      26.083 -22.699   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      27.502 -23.468   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      27.502 -25.007   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      16.934 -31.677   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      18.764 -31.660   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      19.242 -26.547   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      22.011 -26.632   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      23.431 -28.924   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      26.100 -24.238   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      25.176 -21.450   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      26.989 -21.468   0.000  0.00  0.00           C+0
HETATM   31  H   UNK     0      19.242 -30.873   0.000  0.00  0.00           H+0
HETATM   32  H   UNK     0      20.662 -28.565   0.000  0.00  0.00           H+0
HETATM   33  H   UNK     0      24.749 -26.256   0.000  0.00  0.00           H+0
HETATM   34  O   UNK     0      26.270 -19.982   0.000  0.00  0.00           O+0
HETATM   35  O   UNK     0      28.341 -21.304   0.000  0.00  0.00           O+0
HETATM   36  O   UNK     0      19.335 -25.080   0.000  0.00  0.00           O+0
HETATM   37  O   UNK     0      15.207 -30.398   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0      13.871 -31.170   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      12.535 -30.398   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0      13.871 -32.712   0.000  0.00  0.00           O+0
HETATM   41  C   UNK     0      11.198 -31.170   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0      12.535 -33.484   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0      11.199 -32.712   0.000  0.00  0.00           C+0
HETATM   44  O   UNK     0      12.534 -28.856   0.000  0.00  0.00           O+0
HETATM   45  O   UNK     0       9.862 -30.399   0.000  0.00  0.00           O+0
HETATM   46  O   UNK     0       9.863 -33.484   0.000  0.00  0.00           O+0
HETATM   47  C   UNK     0      12.535 -35.027   0.000  0.00  0.00           C+0
HETATM   48  O   UNK     0      11.199 -35.798   0.000  0.00  0.00           O+0
HETATM   49  C   UNK     0      12.534 -27.313   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0      11.198 -26.542   0.000  0.00  0.00           C+0
HETATM   51  O   UNK     0      13.870 -26.542   0.000  0.00  0.00           O+0
HETATM   52  C   UNK     0      11.198 -24.999   0.000  0.00  0.00           C+0
HETATM   53  C   UNK     0      13.870 -24.999   0.000  0.00  0.00           C+0
HETATM   54  C   UNK     0      12.534 -24.228   0.000  0.00  0.00           C+0
HETATM   55  O   UNK     0       9.862 -27.313   0.000  0.00  0.00           O+0
HETATM   56  O   UNK     0       9.862 -24.228   0.000  0.00  0.00           O+0
HETATM   57  O   UNK     0      12.534 -22.685   0.000  0.00  0.00           O+0
HETATM   58  C   UNK     0      15.206 -24.228   0.000  0.00  0.00           C+0
HETATM   59  O   UNK     0      15.206 -22.685   0.000  0.00  0.00           O+0
HETATM   60  O   UNK     0      13.878 -35.507   0.000  0.00  0.00           O+0
HETATM   61  O   UNK     0      16.296 -25.146   0.000  0.00  0.00           O+0
CONECT    1   10    2                                                       
CONECT    2    1    3                                                       
CONECT    3    4    2   37                                                  
CONECT    4    5    3   23   24                                             
CONECT    5   10    4    6   31                                             
CONECT    6    5    7                                                       
CONECT    7    8    6                                                       
CONECT    8    9    7   14   26                                             
CONECT    9   10   11    8   32                                             
CONECT   10    1    9    5   25                                             
CONECT   11    9   12   36                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   18                                                  
CONECT   14    8   15   13   27                                             
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   22   28                                             
CONECT   18   13   19   17   33                                             
CONECT   19   18   20                                                       
CONECT   20   19   21   30   29                                             
CONECT   21   20   22                                                       
CONECT   22   17   21                                                       
CONECT   23    4                                                            
CONECT   24    4                                                            
CONECT   25   10                                                            
CONECT   26    8                                                            
CONECT   27   14                                                            
CONECT   28   17                                                            
CONECT   29   20                                                            
CONECT   30   20   34   35                                                  
CONECT   31    5                                                            
CONECT   32    9                                                            
CONECT   33   18                                                            
CONECT   34   30                                                            
CONECT   35   30                                                            
CONECT   36   11                                                            
CONECT   37    3   38                                                       
CONECT   38   39   40   37                                                  
CONECT   39   38   41   44                                                  
CONECT   40   38   42                                                       
CONECT   41   39   43   45                                                  
CONECT   42   40   43   47                                                  
CONECT   43   41   42   46                                                  
CONECT   44   39   49                                                       
CONECT   45   41                                                            
CONECT   46   43                                                            
CONECT   47   42   48   60                                                  
CONECT   48   47                                                            
CONECT   49   50   51   44                                                  
CONECT   50   49   52   55                                                  
CONECT   51   49   53                                                       
CONECT   52   50   54   56                                                  
CONECT   53   51   54   58                                                  
CONECT   54   52   53   57                                                  
CONECT   55   50                                                            
CONECT   56   52                                                            
CONECT   57   54                                                            
CONECT   58   53   59   61                                                  
CONECT   59   58                                                            
CONECT   60   47                                                            
CONECT   61   58                                                            
MASTER        0    0    0    0    0    0    0    0   61    0  134    0
END

Synonyms

Value	Source
(3beta,20beta)-20-Carboxy-11-oxo-30-norolean-12-en-3-yl-2-O-beta-D-glucopyranuronosyl-alpha-D-glucopyranosiduronic acid	ChEBI
Glycyrrhizin	ChEBI
(3b,20b)-20-Carboxy-11-oxo-30-norolean-12-en-3-yl-2-O-b-D-glucopyranuronosyl-a-D-glucopyranosiduronate	Generator
(3b,20b)-20-Carboxy-11-oxo-30-norolean-12-en-3-yl-2-O-b-D-glucopyranuronosyl-a-D-glucopyranosiduronic acid	Generator
(3beta,20beta)-20-Carboxy-11-oxo-30-norolean-12-en-3-yl-2-O-beta-D-glucopyranuronosyl-alpha-D-glucopyranosiduronate	Generator
(3Β,20β)-20-carboxy-11-oxo-30-norolean-12-en-3-yl-2-O-β-D-glucopyranuronosyl-α-D-glucopyranosiduronate	Generator
(3Β,20β)-20-carboxy-11-oxo-30-norolean-12-en-3-yl-2-O-β-D-glucopyranuronosyl-α-D-glucopyranosiduronic acid	Generator
Glycyrrhizate	Generator
Glycyrrhizic acid	ChEBI
Diammonium glycyrrhizinate	MeSH
Zinc glycyrrhizate	MeSH
Acid, glycyrrhizic	MeSH
Glycyrrhizinic acid	MeSH
Acid, glycyrrhizinic	MeSH
Dipotassium glycyrrhizinate	MeSH
Glycyrrhizate, zinc	MeSH
Glycyrrhizinate, diammonium	MeSH
Glycyrrhizinate, dipotassium	MeSH

Molecular Formula

C₄₂H₆₂O₁₆

Average Mass

822.942

Monoisotopic Mass

822.403785916

IUPAC Name

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

Traditional Name

glycyrrhizin

CAS Registry Number

Not Available

SMILES

[H][C@@]12C[C@](C)(CC[C@]1(C)CC[C@]1(C)C2=CC(=O)[C@]2([H])[C@@]3(C)CC[C@H](O[C@H]4O[C@@H]([C@@H](O)[C@H](O)[C@H]4O[C@@H]4O[C@@H]([C@@H](O)[C@H](O)[C@H]4O)C(O)=O)C(O)=O)C(C)(C)[C@]3([H])CC[C@@]12C)C(O)=O

InChI Identifier

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

InChI Key

LPLVUJXQOOQHMX-QWBHMCJMSA-N

Chemical Taxonomy

Description

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

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene glycosides

Direct Parent

Triterpene saponins

Alternative Parents

Substituents

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

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

enone (CHEBI:15939 )
tricarboxylic acid (CHEBI:15939 )
glucosiduronic acid (CHEBI:15939 )
triterpenoid saponin (CHEBI:15939 )
pentacyclic triterpenoid (CHEBI:15939 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	0.054 g/L	ALOGPS
logP	2.78	ALOGPS
logP	3.13	ChemAxon
logS	-4.2	ALOGPS
pKa (Strongest Acidic)	2.96	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	-3	ChemAxon
Hydrogen Acceptor Count	16	ChemAxon
Hydrogen Donor Count	8	ChemAxon
Polar Surface Area	267.04 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	198.83 m³·mol⁻¹	ChemAxon
Polarizability	86.35 Å³	ChemAxon
Number of Rings	7	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_4) - 70eV, Positive	Not Available	2022-08-08	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-00di-0000000090-4ce2b1a1894e31a4b583	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-00di-0000000090-05cf6f9c95233e0b6093	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-00di-0000000090-b7273d4a3c7ac5053507	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-00di-0000000090-380d12d32657ccb592bc	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-00di-0102000090-bed09978385e89f7fa03	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-00di-0101000090-e2103026d03012f4386b	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-00di-0002000090-301b760e1a43241eb03d	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-00di-0202000090-f5911cc6b21dd8fa08fa	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-00di-0002000090-8620dc60deae22ab4b96	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-TOF , negative	splash10-00di-0000000090-f5c5cfd754bfd69139d6	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-TOF , negative	splash10-00di-0000000090-ec1596ab8cbd06c136c1	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-TOF , negative	splash10-0w29-0709000000-3a40dbcd4a9e24a4e64a	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-TOF , negative	splash10-00di-0000000090-00d5155c760746cee29c	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-TOF , negative	splash10-00di-0001000090-5fd4d3fb6b71940d3e21	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-TOF , negative	splash10-0fk9-0104000090-35df1ca6b0cc93c2681b	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-TOF , negative	splash10-0uk9-0309000050-ce67083e8ed48da875b9	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-006x-0000000090-8cd630bf15ce35555075	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-0fk9-0000702090-b0ba25c87ff68dd3b767	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-0udi-0000901000-57104f23e3197f427a1d	2017-09-14	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0kor-0100906240-38e22c4d3b2d92e7e509	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0fk9-0100903000-e9c85f0d5255892714b1	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00fr-0302901000-45e1b08ddcbdc4c5de1e	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0g29-1600827960-582446907b46f4d6cbf7	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-016s-1700924300-bf530faa06e887dd67f6	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00kb-3800911000-853ddaa12db092f48627	2016-08-03	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Not Available

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Eukaryota/Fungi	Ascomycota	1	Human feces; Human saliva	Unknown

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference

External Links

HMDB ID

Not Available

DrugBank ID

DB13751

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

GLYCYRRHIZINATE

BiGG ID

Not Available

Wikipedia Link

Glycyrrhizin

METLIN ID

Not Available

PubChem Compound

14982

PDB ID

Not Available

ChEBI ID

15939

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Ramirez-Gaona M, Marcu A, Pon A, Guo AC, Sajed T, Wishart NA, Karu N, Djoumbou Feunang Y, Arndt D, Wishart DS: YMDB 2.0: a significantly expanded version of the yeast metabolome database. Nucleic Acids Res. 2017 Jan 4;45(D1):D440-D445. doi: 10.1093/nar/gkw1058. Epub 2016 Nov 28. [PubMed:27899612 ]

Showing metabocard for Glycyrrhyzin (MMDBc0033646)

MOL for #<Metabolite:0x00005634c2aafaa8>

3D MOL for #<Metabolite:0x00005634c2aafaa8>

3D SDF for #<Metabolite:0x00005634c2aafaa8>

3D-SDF for #<Metabolite:0x00005634c2aafaa8>

PDB for #<Metabolite:0x00005634c2aafaa8>

3D PDB for #<Metabolite:0x00005634c2aafaa8>

SMILES for #<Metabolite:0x00005634c2aafaa8>

INCHI for #<Metabolite:0x00005634c2aafaa8>

Structure for #<Metabolite:0x00005634c2aafaa8>

3D Structure for #<Metabolite:0x00005634c2aafaa8>