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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-12 02:03:11 UTC

Update Date

2022-03-07 02:56:37 UTC

HMDB ID

HMDB0040499

Secondary Accession Numbers

HMDB40499

Metabolite Identification

Common Name

18alpha-Hydroxyglycyrrhetic acid

Description

18alpha-Hydroxyglycyrrhetic acid, also known as 18α-hydroxyglycyrrhetate, belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units. Based on a literature review a small amount of articles have been published on 18alpha-Hydroxyglycyrrhetic acid.

Structure

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


  Mrv0541 05061311532D          

 35 39  0  0  0  0            999 V2000
    3.7903    3.1769    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7088    2.6466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6982    0.1231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    3.0789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2836    0.9355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5452    3.3146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3975    3.3912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6961    3.0789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9336    0.9355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1086    0.9355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8711    3.0789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2539    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.6336    0.9355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.6961    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6336    2.3645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4586    2.3645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6039    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8711    0.2211    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1711    1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7599   -0.1591    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2487    1.1837    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1914    0.9355    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 10  9  1  0  0  0  0
 11  8  1  0  0  0  0
 13 12  1  0  0  0  0
 15 14  1  0  0  0  0
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 29 11  1  0  0  0  0
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 29 28  1  0  0  0  0
 30 17  1  0  0  0  0
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 30 26  1  0  0  0  0
 31 18  2  0  0  0  0
 32 21  1  0  0  0  0
 33 23  2  0  0  0  0
 34 23  1  0  0  0  0
 35 30  1  0  0  0  0
M  END

HMDB0040499
     RDKit          3D
18alpha-Hydroxyglycyrrhetic acid
 81 85  0  0  0  0  0  0  0  0999 V2000
    5.0391    2.8097   -0.3648 C   0  0  0  0  0  0  0  0  0  0  0  0
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 34 79  1  0
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 35 81  1  0
M  END


  Mrv0541 05061311532D          

 35 39  0  0  0  0            999 V2000
    3.7903    3.1769    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7088    2.6466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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 22 18  1  0  0  0  0
 24  1  1  0  0  0  0
 24  2  1  0  0  0  0
 24 19  1  0  0  0  0
 24 21  1  0  0  0  0
 25  3  1  0  0  0  0
 25 12  1  0  0  0  0
 25 17  1  0  0  0  0
 25 23  1  0  0  0  0
 26  4  1  0  0  0  0
 26 13  1  0  0  0  0
 26 14  1  0  0  0  0
 27  5  1  0  0  0  0
 27 10  1  0  0  0  0
 27 19  1  0  0  0  0
 27 22  1  0  0  0  0
 28  6  1  0  0  0  0
 28 15  1  0  0  0  0
 28 20  1  0  0  0  0
 29  7  1  0  0  0  0
 29 11  1  0  0  0  0
 29 22  1  0  0  0  0
 29 28  1  0  0  0  0
 30 17  1  0  0  0  0
 30 20  1  0  0  0  0
 30 26  1  0  0  0  0
 31 18  2  0  0  0  0
 32 21  1  0  0  0  0
 33 23  2  0  0  0  0
 34 23  1  0  0  0  0
 35 30  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0040499

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1(C)C(O)CCC2(C)C1CCC1(C)C2C(=O)C=C2C1(C)CCC1(C)CCC(C)(CC21O)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C30H46O5/c1-24(2)19-8-11-29(7)22(27(19,5)10-9-21(24)32)18(31)16-20-28(29,6)15-14-26(4)13-12-25(3,23(33)34)17-30(20,26)35/h16,19,21-22,32,35H,8-15,17H2,1-7H3,(H,33,34)

> <INCHI_KEY>
FCVHQYZUEPQNJU-UHFFFAOYSA-N

> <FORMULA>
C30H46O5

> <MOLECULAR_WEIGHT>
486.6832

> <EXACT_MASS>
486.334524582

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
56.18642825049958

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
10,14b-dihydroxy-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>
4.54

> <JCHEM_LOGP>
5.027935731333335

> <ALOGPS_LOGS>
-5.32

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
13.773924426473357

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.353529605968222

> <JCHEM_PKA_STRONGEST_BASIC>
-0.8351286992301529

> <JCHEM_POLAR_SURFACE_AREA>
94.83

> <JCHEM_REFRACTIVITY>
135.64259999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.31e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
10,14b-dihydroxy-2,4a,6a,6b,9,9,12a-heptamethyl-13-oxo-1,3,4,5,6,7,8,8a,10,11,12,12b-dodecahydropicene-2-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0040499
     RDKit          3D
18alpha-Hydroxyglycyrrhetic acid
 81 85  0  0  0  0  0  0  0  0999 V2000
    5.0391    2.8097   -0.3648 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9497    1.2717   -0.3255 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9462    0.8439   -1.3671 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9073    0.1573   -1.0055 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7543    1.2308   -2.6823 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2948    0.8464    1.0406 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6908   -0.3661    1.6120 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4938   -0.9062    0.8045 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0960   -1.7989   -0.2242 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6786   -1.7443    1.7363 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2079   -1.5810    1.6723 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6774   -1.0937    0.3305 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9768   -2.0584   -0.7972 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3540    0.1616    0.0790 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6587    1.2034   -0.3442 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7965    1.1013   -0.5610 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4428    2.1600   -0.5394 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3134   -0.2794   -0.7793 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8014   -0.2792   -1.0347 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0942   -1.5976   -1.7917 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1304    0.8027   -2.0194 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0938    1.8443   -1.6621 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6394    1.8267   -0.2637 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9046    2.4679   -0.2291 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8347    0.4582    0.2645 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8478   -0.2933   -0.5904 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4045    0.5335    1.6471 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4967   -0.2846    0.2518 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7487    0.1552    1.4617 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3261   -0.2136    1.6056 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8386   -1.0374    0.4112 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2617   -2.4259    0.6489 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7978    0.3181    0.3086 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8884    1.2658    1.3746 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5613    0.9288   -0.8093 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9773    3.0868   -1.4360 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0137    3.1393    0.0360 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2442    3.2641    0.2537 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4023    1.8733   -3.0900 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1641    1.7052    1.7672 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4188    0.6949    1.0607 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4235   -1.2193    1.7137 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3271   -0.1854    2.6444 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8245   -2.8858   -0.0477 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2271   -1.8424   -0.1935 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8366   -1.6131   -1.2619 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9771   -1.5743    2.8146 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8981   -2.8447    1.5933 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9001   -0.7651    2.3933 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7226   -2.4819    2.0433 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4979   -1.5518   -1.6438 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0377   -2.4463   -1.2997 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4767   -2.9845   -0.4513 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1089    2.1758   -0.5496 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8140   -0.6446   -1.7003 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6332   -1.3708   -2.7720 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8513   -2.2072   -1.2733 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1916   -2.0971   -2.1319 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5445    0.3535   -2.9931 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2100    1.2684   -2.4615 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7169    2.8877   -1.8391 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0243    1.8460   -2.3188 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0041    2.4421    0.3909 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3175    2.3177   -1.1209 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9088   -1.3482   -0.3202 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8329    0.1771   -0.3740 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6466   -0.1111   -1.6627 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8252    1.1505    2.3409 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5671   -0.5031    2.0055 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4130    0.9900    1.5642 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8375   -1.3460    0.4657 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2949   -0.2682    2.3618 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8281    1.2674    1.6531 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6448    0.6700    1.7651 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1298   -0.8694    2.4931 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4278   -3.1969    0.5341 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0614   -2.8622    0.0791 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5393   -2.6196    1.7391 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1710    1.9284    1.3026 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6235    0.3244   -1.7372 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9946    1.8487   -1.1446 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  2  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
 18 19  1  0
 19 20  1  0
 19 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 23 25  1  0
 25 26  1  0
 25 27  1  0
 25 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  1  0
 31 32  1  0
 14 33  1  0
 33 34  1  0
 33 35  1  0
 35  2  1  0
 33  8  1  0
 31 12  1  0
 31 18  1  0
 28 19  1  0
  1 36  1  0
  1 37  1  0
  1 38  1  0
  5 39  1  0
  6 40  1  0
  6 41  1  0
  7 42  1  0
  7 43  1  0
  9 44  1  0
  9 45  1  0
  9 46  1  0
 10 47  1  0
 10 48  1  0
 11 49  1  0
 11 50  1  0
 13 51  1  0
 13 52  1  0
 13 53  1  0
 15 54  1  0
 18 55  1  0
 20 56  1  0
 20 57  1  0
 20 58  1  0
 21 59  1  0
 21 60  1  0
 22 61  1  0
 22 62  1  0
 23 63  1  0
 24 64  1  0
 26 65  1  0
 26 66  1  0
 26 67  1  0
 27 68  1  0
 27 69  1  0
 27 70  1  0
 28 71  1  0
 29 72  1  0
 29 73  1  0
 30 74  1  0
 30 75  1  0
 32 76  1  0
 32 77  1  0
 32 78  1  0
 34 79  1  0
 35 80  1  0
 35 81  1  0
M  END

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       7.075   5.930   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.790   4.940   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -3.170   0.230   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.667   5.747   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.263   1.746   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.018   6.187   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.609   6.330   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.033   5.747   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.343   1.746   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.803   1.746   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.493   5.747   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -4.207   3.080   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -3.437   4.414   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.127   5.747   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.413   5.747   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.183   1.746   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -1.897   1.746   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.723   1.746   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.803   4.414   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.413   3.080   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       8.113   3.080   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       3.493   3.080   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -4.885   1.220   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       7.343   4.414   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -3.437   1.746   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -1.897   4.414   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       5.033   3.080   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       1.183   4.414   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       2.723   4.414   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -1.127   3.080   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       3.493   0.413   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0       9.653   3.080   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0      -5.152  -0.297   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0      -6.064   2.210   0.000  0.00  0.00           O+0
HETATM   35  O   UNK     0      -0.357   1.746   0.000  0.00  0.00           O+0
CONECT    1   24                                                            
CONECT    2   24                                                            
CONECT    3   25                                                            
CONECT    4   26                                                            
CONECT    5   27                                                            
CONECT    6   28                                                            
CONECT    7   29                                                            
CONECT    8   11   19                                                       
CONECT    9   10   21                                                       
CONECT   10    9   27                                                       
CONECT   11    8   29                                                       
CONECT   12   13   25                                                       
CONECT   13   12   26                                                       
CONECT   14   15   26                                                       
CONECT   15   14   28                                                       
CONECT   16   18   20                                                       
CONECT   17   25   30                                                       
CONECT   18   16   22   31                                                  
CONECT   19    8   24   27                                                  
CONECT   20   16   28   30                                                  
CONECT   21    9   24   32                                                  
CONECT   22   18   27   29                                                  
CONECT   23   25   33   34                                                  
CONECT   24    1    2   19   21                                             
CONECT   25    3   12   17   23                                             
CONECT   26    4   13   14   30                                             
CONECT   27    5   10   19   22                                             
CONECT   28    6   15   20   29                                             
CONECT   29    7   11   22   28                                             
CONECT   30   17   20   26   35                                             
CONECT   31   18                                                            
CONECT   32   21                                                            
CONECT   33   23                                                            
CONECT   34   23                                                            
CONECT   35   30                                                            
MASTER        0    0    0    0    0    0    0    0   35    0   78    0
END

COMPND    HMDB0040499
HETATM    1  C1  UNL     1       5.039   2.810  -0.365  1.00  0.00           C  
HETATM    2  C2  UNL     1       4.950   1.272  -0.326  1.00  0.00           C  
HETATM    3  C3  UNL     1       5.946   0.844  -1.367  1.00  0.00           C  
HETATM    4  O1  UNL     1       6.907   0.157  -1.005  1.00  0.00           O  
HETATM    5  O2  UNL     1       5.754   1.231  -2.682  1.00  0.00           O  
HETATM    6  C4  UNL     1       5.295   0.846   1.041  1.00  0.00           C  
HETATM    7  C5  UNL     1       4.691  -0.366   1.612  1.00  0.00           C  
HETATM    8  C6  UNL     1       3.494  -0.906   0.804  1.00  0.00           C  
HETATM    9  C7  UNL     1       4.096  -1.799  -0.224  1.00  0.00           C  
HETATM   10  C8  UNL     1       2.679  -1.744   1.736  1.00  0.00           C  
HETATM   11  C9  UNL     1       1.208  -1.581   1.672  1.00  0.00           C  
HETATM   12  C10 UNL     1       0.677  -1.094   0.331  1.00  0.00           C  
HETATM   13  C11 UNL     1       0.977  -2.058  -0.797  1.00  0.00           C  
HETATM   14  C12 UNL     1       1.354   0.162   0.079  1.00  0.00           C  
HETATM   15  C13 UNL     1       0.659   1.203  -0.344  1.00  0.00           C  
HETATM   16  C14 UNL     1      -0.796   1.101  -0.561  1.00  0.00           C  
HETATM   17  O3  UNL     1      -1.443   2.160  -0.539  1.00  0.00           O  
HETATM   18  C15 UNL     1      -1.313  -0.279  -0.779  1.00  0.00           C  
HETATM   19  C16 UNL     1      -2.801  -0.279  -1.035  1.00  0.00           C  
HETATM   20  C17 UNL     1      -3.094  -1.598  -1.792  1.00  0.00           C  
HETATM   21  C18 UNL     1      -3.130   0.803  -2.019  1.00  0.00           C  
HETATM   22  C19 UNL     1      -4.094   1.844  -1.662  1.00  0.00           C  
HETATM   23  C20 UNL     1      -4.639   1.827  -0.264  1.00  0.00           C  
HETATM   24  O4  UNL     1      -5.905   2.468  -0.229  1.00  0.00           O  
HETATM   25  C21 UNL     1      -4.835   0.458   0.264  1.00  0.00           C  
HETATM   26  C22 UNL     1      -5.848  -0.293  -0.590  1.00  0.00           C  
HETATM   27  C23 UNL     1      -5.405   0.534   1.647  1.00  0.00           C  
HETATM   28  C24 UNL     1      -3.497  -0.285   0.252  1.00  0.00           C  
HETATM   29  C25 UNL     1      -2.749   0.155   1.462  1.00  0.00           C  
HETATM   30  C26 UNL     1      -1.326  -0.214   1.606  1.00  0.00           C  
HETATM   31  C27 UNL     1      -0.839  -1.037   0.411  1.00  0.00           C  
HETATM   32  C28 UNL     1      -1.262  -2.426   0.649  1.00  0.00           C  
HETATM   33  C29 UNL     1       2.798   0.318   0.309  1.00  0.00           C  
HETATM   34  O5  UNL     1       2.888   1.266   1.375  1.00  0.00           O  
HETATM   35  C30 UNL     1       3.561   0.929  -0.809  1.00  0.00           C  
HETATM   36  H1  UNL     1       4.977   3.087  -1.436  1.00  0.00           H  
HETATM   37  H2  UNL     1       6.014   3.139   0.036  1.00  0.00           H  
HETATM   38  H3  UNL     1       4.244   3.264   0.254  1.00  0.00           H  
HETATM   39  H4  UNL     1       6.402   1.873  -3.090  1.00  0.00           H  
HETATM   40  H5  UNL     1       5.164   1.705   1.767  1.00  0.00           H  
HETATM   41  H6  UNL     1       6.419   0.695   1.061  1.00  0.00           H  
HETATM   42  H7  UNL     1       5.424  -1.219   1.714  1.00  0.00           H  
HETATM   43  H8  UNL     1       4.327  -0.185   2.644  1.00  0.00           H  
HETATM   44  H9  UNL     1       3.825  -2.886  -0.048  1.00  0.00           H  
HETATM   45  H10 UNL     1       5.227  -1.842  -0.193  1.00  0.00           H  
HETATM   46  H11 UNL     1       3.837  -1.613  -1.262  1.00  0.00           H  
HETATM   47  H12 UNL     1       2.977  -1.574   2.815  1.00  0.00           H  
HETATM   48  H13 UNL     1       2.898  -2.845   1.593  1.00  0.00           H  
HETATM   49  H14 UNL     1       0.900  -0.765   2.393  1.00  0.00           H  
HETATM   50  H15 UNL     1       0.723  -2.482   2.043  1.00  0.00           H  
HETATM   51  H16 UNL     1       1.498  -1.552  -1.644  1.00  0.00           H  
HETATM   52  H17 UNL     1       0.038  -2.446  -1.300  1.00  0.00           H  
HETATM   53  H18 UNL     1       1.477  -2.984  -0.451  1.00  0.00           H  
HETATM   54  H19 UNL     1       1.109   2.176  -0.550  1.00  0.00           H  
HETATM   55  H20 UNL     1      -0.814  -0.645  -1.700  1.00  0.00           H  
HETATM   56  H21 UNL     1      -3.633  -1.371  -2.772  1.00  0.00           H  
HETATM   57  H22 UNL     1      -3.851  -2.207  -1.273  1.00  0.00           H  
HETATM   58  H23 UNL     1      -2.192  -2.097  -2.132  1.00  0.00           H  
HETATM   59  H24 UNL     1      -3.545   0.353  -2.993  1.00  0.00           H  
HETATM   60  H25 UNL     1      -2.210   1.268  -2.462  1.00  0.00           H  
HETATM   61  H26 UNL     1      -3.717   2.888  -1.839  1.00  0.00           H  
HETATM   62  H27 UNL     1      -5.024   1.846  -2.319  1.00  0.00           H  
HETATM   63  H28 UNL     1      -4.004   2.442   0.391  1.00  0.00           H  
HETATM   64  H29 UNL     1      -6.318   2.318  -1.121  1.00  0.00           H  
HETATM   65  H30 UNL     1      -5.909  -1.348  -0.320  1.00  0.00           H  
HETATM   66  H31 UNL     1      -6.833   0.177  -0.374  1.00  0.00           H  
HETATM   67  H32 UNL     1      -5.647  -0.111  -1.663  1.00  0.00           H  
HETATM   68  H33 UNL     1      -4.825   1.150   2.341  1.00  0.00           H  
HETATM   69  H34 UNL     1      -5.567  -0.503   2.005  1.00  0.00           H  
HETATM   70  H35 UNL     1      -6.413   0.990   1.564  1.00  0.00           H  
HETATM   71  H36 UNL     1      -3.838  -1.346   0.466  1.00  0.00           H  
HETATM   72  H37 UNL     1      -3.295  -0.268   2.362  1.00  0.00           H  
HETATM   73  H38 UNL     1      -2.828   1.267   1.653  1.00  0.00           H  
HETATM   74  H39 UNL     1      -0.645   0.670   1.765  1.00  0.00           H  
HETATM   75  H40 UNL     1      -1.130  -0.869   2.493  1.00  0.00           H  
HETATM   76  H41 UNL     1      -0.428  -3.197   0.534  1.00  0.00           H  
HETATM   77  H42 UNL     1      -2.061  -2.862   0.079  1.00  0.00           H  
HETATM   78  H43 UNL     1      -1.539  -2.620   1.739  1.00  0.00           H  
HETATM   79  H44 UNL     1       2.171   1.928   1.303  1.00  0.00           H  
HETATM   80  H45 UNL     1       3.623   0.324  -1.737  1.00  0.00           H  
HETATM   81  H46 UNL     1       2.995   1.849  -1.145  1.00  0.00           H  
CONECT    1    2   36   37   38
CONECT    2    3    6   35
CONECT    3    4    4    5
CONECT    5   39
CONECT    6    7   40   41
CONECT    7    8   42   43
CONECT    8    9   10   33
CONECT    9   44   45   46
CONECT   10   11   47   48
CONECT   11   12   49   50
CONECT   12   13   14   31
CONECT   13   51   52   53
CONECT   14   15   15   33
CONECT   15   16   54
CONECT   16   17   17   18
CONECT   18   19   31   55
CONECT   19   20   21   28
CONECT   20   56   57   58
CONECT   21   22   59   60
CONECT   22   23   61   62
CONECT   23   24   25   63
CONECT   24   64
CONECT   25   26   27   28
CONECT   26   65   66   67
CONECT   27   68   69   70
CONECT   28   29   71
CONECT   29   30   72   73
CONECT   30   31   74   75
CONECT   31   32
CONECT   32   76   77   78
CONECT   33   34   35
CONECT   34   79
CONECT   35   80   81
END

HMDB0040499
     RDKit          3D
18alpha-Hydroxyglycyrrhetic acid
 81 85  0  0  0  0  0  0  0  0999 V2000
    5.0391    2.8097   -0.3648 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9497    1.2717   -0.3255 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9462    0.8439   -1.3671 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9073    0.1573   -1.0055 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7543    1.2308   -2.6823 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2948    0.8464    1.0406 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6908   -0.3661    1.6120 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4938   -0.9062    0.8045 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0960   -1.7989   -0.2242 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6786   -1.7443    1.7363 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2079   -1.5810    1.6723 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6774   -1.0937    0.3305 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9768   -2.0584   -0.7972 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3540    0.1616    0.0790 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6587    1.2034   -0.3442 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7965    1.1013   -0.5610 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4428    2.1600   -0.5394 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3134   -0.2794   -0.7793 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8014   -0.2792   -1.0347 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0942   -1.5976   -1.7917 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1304    0.8027   -2.0194 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0938    1.8443   -1.6621 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6394    1.8267   -0.2637 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9046    2.4679   -0.2291 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8347    0.4582    0.2645 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8478   -0.2933   -0.5904 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4045    0.5335    1.6471 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4967   -0.2846    0.2518 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7487    0.1552    1.4617 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3261   -0.2136    1.6056 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8386   -1.0374    0.4112 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2617   -2.4259    0.6489 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7978    0.3181    0.3086 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8884    1.2658    1.3746 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5613    0.9288   -0.8093 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9773    3.0868   -1.4360 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0137    3.1393    0.0360 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2442    3.2641    0.2537 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4023    1.8733   -3.0900 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1641    1.7052    1.7672 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4188    0.6949    1.0607 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4235   -1.2193    1.7137 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3271   -0.1854    2.6444 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8245   -2.8858   -0.0477 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2271   -1.8424   -0.1935 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8366   -1.6131   -1.2619 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9771   -1.5743    2.8146 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8981   -2.8447    1.5933 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9001   -0.7651    2.3933 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7226   -2.4819    2.0433 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4979   -1.5518   -1.6438 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0377   -2.4463   -1.2997 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4767   -2.9845   -0.4513 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1089    2.1758   -0.5496 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8140   -0.6446   -1.7003 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6332   -1.3708   -2.7720 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8513   -2.2072   -1.2733 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1916   -2.0971   -2.1319 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5445    0.3535   -2.9931 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2100    1.2684   -2.4615 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7169    2.8877   -1.8391 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0243    1.8460   -2.3188 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0041    2.4421    0.3909 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3175    2.3177   -1.1209 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9088   -1.3482   -0.3202 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8329    0.1771   -0.3740 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6466   -0.1111   -1.6627 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8252    1.1505    2.3409 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5671   -0.5031    2.0055 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4130    0.9900    1.5642 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8375   -1.3460    0.4657 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2949   -0.2682    2.3618 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8281    1.2674    1.6531 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6448    0.6700    1.7651 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1298   -0.8694    2.4931 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4278   -3.1969    0.5341 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0614   -2.8622    0.0791 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5393   -2.6196    1.7391 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1710    1.9284    1.3026 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6235    0.3244   -1.7372 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9946    1.8487   -1.1446 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  2  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
 18 19  1  0
 19 20  1  0
 19 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 23 25  1  0
 25 26  1  0
 25 27  1  0
 25 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  1  0
 31 32  1  0
 14 33  1  0
 33 34  1  0
 33 35  1  0
 35  2  1  0
 33  8  1  0
 31 12  1  0
 31 18  1  0
 28 19  1  0
  1 36  1  0
  1 37  1  0
  1 38  1  0
  5 39  1  0
  6 40  1  0
  6 41  1  0
  7 42  1  0
  7 43  1  0
  9 44  1  0
  9 45  1  0
  9 46  1  0
 10 47  1  0
 10 48  1  0
 11 49  1  0
 11 50  1  0
 13 51  1  0
 13 52  1  0
 13 53  1  0
 15 54  1  0
 18 55  1  0
 20 56  1  0
 20 57  1  0
 20 58  1  0
 21 59  1  0
 21 60  1  0
 22 61  1  0
 22 62  1  0
 23 63  1  0
 24 64  1  0
 26 65  1  0
 26 66  1  0
 26 67  1  0
 27 68  1  0
 27 69  1  0
 27 70  1  0
 28 71  1  0
 29 72  1  0
 29 73  1  0
 30 74  1  0
 30 75  1  0
 32 76  1  0
 32 77  1  0
 32 78  1  0
 34 79  1  0
 35 80  1  0
 35 81  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
18a-Hydroxyglycyrrhetate	Generator
18a-Hydroxyglycyrrhetic acid	Generator
18alpha-Hydroxyglycyrrhetate	Generator
18Α-hydroxyglycyrrhetate	Generator
18Α-hydroxyglycyrrhetic acid	Generator
10,14b-Dihydroxy-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	Generator

Chemical Formula

C₃₀H₄₆O₅

Average Molecular Weight

486.6832

Monoisotopic Molecular Weight

486.334524582

IUPAC Name

10,14b-dihydroxy-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

10,14b-dihydroxy-2,4a,6a,6b,9,9,12a-heptamethyl-13-oxo-1,3,4,5,6,7,8,8a,10,11,12,12b-dodecahydropicene-2-carboxylic acid

CAS Registry Number

17991-67-2

SMILES

CC1(C)C(O)CCC2(C)C1CCC1(C)C2C(=O)C=C2C1(C)CCC1(C)CCC(C)(CC21O)C(O)=O

InChI Identifier

InChI=1S/C30H46O5/c1-24(2)19-8-11-29(7)22(27(19,5)10-9-21(24)32)18(31)16-20-28(29,6)15-14-26(4)13-12-25(3,23(33)34)17-30(20,26)35/h16,19,21-22,32,35H,8-15,17H2,1-7H3,(H,33,34)

InChI Key

FCVHQYZUEPQNJU-UHFFFAOYSA-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
Tertiary alcohol
Secondary alcohol
Ketone
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Alcohol
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Carbonyl group
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Route of exposure

Enteral

Ingestion (HMDB: HMDB0040499)

Source

Endogenous

Endogenous (HMDB: HMDB0040499)

Plant

Plant (HMDB: HMDB0040499)

Animal

Animal (HMDB: HMDB0040499)

Exogenous

Food

Food (HMDB: HMDB0040499)

Herb and spice

Herbs and Spices (FooDB: FOOD00866)

Exogenous (HMDB: HMDB0040499)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0040499)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0040499)

Lipid metabolism pathway (HMDB: HMDB0040499)

Cellular process

Cell signaling (HMDB: HMDB0040499)

Biochemical process

Lipid transport (HMDB: HMDB0040499)

Role

Biological role

Energy source (HMDB: HMDB0040499)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0040499)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	252 - 255 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.024 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.0023 g/L	ALOGPS
logP	4.54	ALOGPS
logP	5.03	ChemAxon
logS	-5.3	ALOGPS
pKa (Strongest Acidic)	4.35	ChemAxon
pKa (Strongest Basic)	-0.84	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	94.83 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	135.64 m³·mol⁻¹	ChemAxon
Polarizability	56.19 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]+	211.952	31661259
DarkChem	[M-H]-	202.595	31661259
DeepCCS	[M-2H]-	243.447	30932474
DeepCCS	[M+Na]+	218.889	30932474
AllCCS	[M+H]+	218.4	32859911
AllCCS	[M+H-H2O]+	216.9	32859911
AllCCS	[M+NH4]+	219.8	32859911
AllCCS	[M+Na]+	220.2	32859911
AllCCS	[M-H]-	215.0	32859911
AllCCS	[M+Na-2H]-	217.3	32859911
AllCCS	[M+HCOO]-	219.8	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.	8.81 minutes	32390414
Predicted by Siyang on May 30, 2022	17.389 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.59 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	3185.6 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	212.8 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	237.1 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	165.1 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	390.5 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	845.2 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	860.3 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	94.7 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1371.5 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	613.7 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	1858.7 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	539.7 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	528.1 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	188.5 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	381.0 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
18alpha-Hydroxyglycyrrhetic acid	CC1(C)C(O)CCC2(C)C1CCC1(C)C2C(=O)C=C2C1(C)CCC1(C)CCC(C)(CC21O)C(O)=O	3880.8	Standard polar	33892256
18alpha-Hydroxyglycyrrhetic acid	CC1(C)C(O)CCC2(C)C1CCC1(C)C2C(=O)C=C2C1(C)CCC1(C)CCC(C)(CC21O)C(O)=O	3522.9	Standard non polar	33892256
18alpha-Hydroxyglycyrrhetic acid	CC1(C)C(O)CCC2(C)C1CCC1(C)C2C(=O)C=C2C1(C)CCC1(C)CCC(C)(CC21O)C(O)=O	4092.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
18alpha-Hydroxyglycyrrhetic acid,1TMS,isomer #1	CC1(C(=O)O)CCC2(C)CCC3(C)C(=CC(=O)C4C5(C)CCC(O[Si](C)(C)C)C(C)(C)C5CCC43C)C2(O)C1	4168.9	Semi standard non polar	33892256
18alpha-Hydroxyglycyrrhetic acid,1TMS,isomer #2	CC1(C(=O)O)CCC2(C)CCC3(C)C(=CC(=O)C4C5(C)CCC(O)C(C)(C)C5CCC43C)C2(O[Si](C)(C)C)C1	4146.3	Semi standard non polar	33892256
18alpha-Hydroxyglycyrrhetic acid,1TMS,isomer #3	CC1(C(=O)O[Si](C)(C)C)CCC2(C)CCC3(C)C(=CC(=O)C4C5(C)CCC(O)C(C)(C)C5CCC43C)C2(O)C1	4089.6	Semi standard non polar	33892256
18alpha-Hydroxyglycyrrhetic acid,1TMS,isomer #4	CC1(C(=O)O)CCC2(C)CCC3(C)C(=CC(O[Si](C)(C)C)=C4C5(C)CCC(O)C(C)(C)C5CCC43C)C2(O)C1	4062.2	Semi standard non polar	33892256
18alpha-Hydroxyglycyrrhetic acid,2TMS,isomer #1	CC1(C(=O)O[Si](C)(C)C)CCC2(C)CCC3(C)C(=CC(=O)C4C5(C)CCC(O[Si](C)(C)C)C(C)(C)C5CCC43C)C2(O)C1	4093.1	Semi standard non polar	33892256
18alpha-Hydroxyglycyrrhetic acid,2TMS,isomer #2	CC1(C(=O)O)CCC2(C)CCC3(C)C(=CC(=O)C4C5(C)CCC(O[Si](C)(C)C)C(C)(C)C5CCC43C)C2(O[Si](C)(C)C)C1	4119.2	Semi standard non polar	33892256
18alpha-Hydroxyglycyrrhetic acid,2TMS,isomer #3	CC1(C(=O)O)CCC2(C)CCC3(C)C(=CC(O[Si](C)(C)C)=C4C5(C)CCC(O[Si](C)(C)C)C(C)(C)C5CCC43C)C2(O)C1	4044.7	Semi standard non polar	33892256
18alpha-Hydroxyglycyrrhetic acid,2TMS,isomer #4	CC1(C(=O)O[Si](C)(C)C)CCC2(C)CCC3(C)C(=CC(=O)C4C5(C)CCC(O)C(C)(C)C5CCC43C)C2(O[Si](C)(C)C)C1	4052.3	Semi standard non polar	33892256
18alpha-Hydroxyglycyrrhetic acid,2TMS,isomer #5	CC1(C(=O)O)CCC2(C)CCC3(C)C(=CC(O[Si](C)(C)C)=C4C5(C)CCC(O)C(C)(C)C5CCC43C)C2(O[Si](C)(C)C)C1	3988.9	Semi standard non polar	33892256
18alpha-Hydroxyglycyrrhetic acid,2TMS,isomer #6	CC1(C(=O)O[Si](C)(C)C)CCC2(C)CCC3(C)C(=CC(O[Si](C)(C)C)=C4C5(C)CCC(O)C(C)(C)C5CCC43C)C2(O)C1	4003.6	Semi standard non polar	33892256
18alpha-Hydroxyglycyrrhetic acid,3TMS,isomer #1	CC1(C(=O)O[Si](C)(C)C)CCC2(C)CCC3(C)C(=CC(=O)C4C5(C)CCC(O[Si](C)(C)C)C(C)(C)C5CCC43C)C2(O[Si](C)(C)C)C1	3975.4	Semi standard non polar	33892256
18alpha-Hydroxyglycyrrhetic acid,3TMS,isomer #2	CC1(C(=O)O[Si](C)(C)C)CCC2(C)CCC3(C)C(=CC(O[Si](C)(C)C)=C4C5(C)CCC(O[Si](C)(C)C)C(C)(C)C5CCC43C)C2(O)C1	3937.3	Semi standard non polar	33892256
18alpha-Hydroxyglycyrrhetic acid,3TMS,isomer #3	CC1(C(=O)O)CCC2(C)CCC3(C)C(=CC(O[Si](C)(C)C)=C4C5(C)CCC(O[Si](C)(C)C)C(C)(C)C5CCC43C)C2(O[Si](C)(C)C)C1	3909.4	Semi standard non polar	33892256
18alpha-Hydroxyglycyrrhetic acid,3TMS,isomer #4	CC1(C(=O)O[Si](C)(C)C)CCC2(C)CCC3(C)C(=CC(O[Si](C)(C)C)=C4C5(C)CCC(O)C(C)(C)C5CCC43C)C2(O[Si](C)(C)C)C1	3877.1	Semi standard non polar	33892256
18alpha-Hydroxyglycyrrhetic acid,4TMS,isomer #1	CC1(C(=O)O[Si](C)(C)C)CCC2(C)CCC3(C)C(=CC(O[Si](C)(C)C)=C4C5(C)CCC(O[Si](C)(C)C)C(C)(C)C5CCC43C)C2(O[Si](C)(C)C)C1	3805.6	Semi standard non polar	33892256
18alpha-Hydroxyglycyrrhetic acid,4TMS,isomer #1	CC1(C(=O)O[Si](C)(C)C)CCC2(C)CCC3(C)C(=CC(O[Si](C)(C)C)=C4C5(C)CCC(O[Si](C)(C)C)C(C)(C)C5CCC43C)C2(O[Si](C)(C)C)C1	3735.5	Standard non polar	33892256
18alpha-Hydroxyglycyrrhetic acid,1TBDMS,isomer #1	CC1(C(=O)O)CCC2(C)CCC3(C)C(=CC(=O)C4C5(C)CCC(O[Si](C)(C)C(C)(C)C)C(C)(C)C5CCC43C)C2(O)C1	4376.4	Semi standard non polar	33892256
18alpha-Hydroxyglycyrrhetic acid,1TBDMS,isomer #2	CC1(C(=O)O)CCC2(C)CCC3(C)C(=CC(=O)C4C5(C)CCC(O)C(C)(C)C5CCC43C)C2(O[Si](C)(C)C(C)(C)C)C1	4345.3	Semi standard non polar	33892256
18alpha-Hydroxyglycyrrhetic acid,1TBDMS,isomer #3	CC1(C(=O)O[Si](C)(C)C(C)(C)C)CCC2(C)CCC3(C)C(=CC(=O)C4C5(C)CCC(O)C(C)(C)C5CCC43C)C2(O)C1	4321.5	Semi standard non polar	33892256
18alpha-Hydroxyglycyrrhetic acid,1TBDMS,isomer #4	CC1(C(=O)O)CCC2(C)CCC3(C)C(=CC(O[Si](C)(C)C(C)(C)C)=C4C5(C)CCC(O)C(C)(C)C5CCC43C)C2(O)C1	4300.9	Semi standard non polar	33892256
18alpha-Hydroxyglycyrrhetic acid,2TBDMS,isomer #1	CC1(C(=O)O[Si](C)(C)C(C)(C)C)CCC2(C)CCC3(C)C(=CC(=O)C4C5(C)CCC(O[Si](C)(C)C(C)(C)C)C(C)(C)C5CCC43C)C2(O)C1	4524.8	Semi standard non polar	33892256
18alpha-Hydroxyglycyrrhetic acid,2TBDMS,isomer #2	CC1(C(=O)O)CCC2(C)CCC3(C)C(=CC(=O)C4C5(C)CCC(O[Si](C)(C)C(C)(C)C)C(C)(C)C5CCC43C)C2(O[Si](C)(C)C(C)(C)C)C1	4539.4	Semi standard non polar	33892256
18alpha-Hydroxyglycyrrhetic acid,2TBDMS,isomer #3	CC1(C(=O)O)CCC2(C)CCC3(C)C(=CC(O[Si](C)(C)C(C)(C)C)=C4C5(C)CCC(O[Si](C)(C)C(C)(C)C)C(C)(C)C5CCC43C)C2(O)C1	4476.7	Semi standard non polar	33892256
18alpha-Hydroxyglycyrrhetic acid,2TBDMS,isomer #4	CC1(C(=O)O[Si](C)(C)C(C)(C)C)CCC2(C)CCC3(C)C(=CC(=O)C4C5(C)CCC(O)C(C)(C)C5CCC43C)C2(O[Si](C)(C)C(C)(C)C)C1	4486.0	Semi standard non polar	33892256
18alpha-Hydroxyglycyrrhetic acid,2TBDMS,isomer #5	CC1(C(=O)O)CCC2(C)CCC3(C)C(=CC(O[Si](C)(C)C(C)(C)C)=C4C5(C)CCC(O)C(C)(C)C5CCC43C)C2(O[Si](C)(C)C(C)(C)C)C1	4425.4	Semi standard non polar	33892256
18alpha-Hydroxyglycyrrhetic acid,2TBDMS,isomer #6	CC1(C(=O)O[Si](C)(C)C(C)(C)C)CCC2(C)CCC3(C)C(=CC(O[Si](C)(C)C(C)(C)C)=C4C5(C)CCC(O)C(C)(C)C5CCC43C)C2(O)C1	4427.4	Semi standard non polar	33892256
18alpha-Hydroxyglycyrrhetic acid,3TBDMS,isomer #1	CC1(C(=O)O[Si](C)(C)C(C)(C)C)CCC2(C)CCC3(C)C(=CC(=O)C4C5(C)CCC(O[Si](C)(C)C(C)(C)C)C(C)(C)C5CCC43C)C2(O[Si](C)(C)C(C)(C)C)C1	4596.5	Semi standard non polar	33892256
18alpha-Hydroxyglycyrrhetic acid,3TBDMS,isomer #2	CC1(C(=O)O[Si](C)(C)C(C)(C)C)CCC2(C)CCC3(C)C(=CC(O[Si](C)(C)C(C)(C)C)=C4C5(C)CCC(O[Si](C)(C)C(C)(C)C)C(C)(C)C5CCC43C)C2(O)C1	4565.3	Semi standard non polar	33892256
18alpha-Hydroxyglycyrrhetic acid,3TBDMS,isomer #3	CC1(C(=O)O)CCC2(C)CCC3(C)C(=CC(O[Si](C)(C)C(C)(C)C)=C4C5(C)CCC(O[Si](C)(C)C(C)(C)C)C(C)(C)C5CCC43C)C2(O[Si](C)(C)C(C)(C)C)C1	4535.7	Semi standard non polar	33892256
18alpha-Hydroxyglycyrrhetic acid,3TBDMS,isomer #4	CC1(C(=O)O[Si](C)(C)C(C)(C)C)CCC2(C)CCC3(C)C(=CC(O[Si](C)(C)C(C)(C)C)=C4C5(C)CCC(O)C(C)(C)C5CCC43C)C2(O[Si](C)(C)C(C)(C)C)C1	4470.9	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 18alpha-Hydroxyglycyrrhetic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-00xr-0309800000-2bb054ebd2e623a3f47b	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 18alpha-Hydroxyglycyrrhetic acid GC-MS (2 TMS) - 70eV, Positive	splash10-014i-1040619000-dc37f95bb9980848f737	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 18alpha-Hydroxyglycyrrhetic 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
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 18alpha-Hydroxyglycyrrhetic acid 10V, Positive-QTOF	splash10-0gb9-0000900000-b759df6a4c6f6b9a2e95	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 18alpha-Hydroxyglycyrrhetic acid 20V, Positive-QTOF	splash10-0v4i-0010900000-ffaba9d09198c51ea2dd	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 18alpha-Hydroxyglycyrrhetic acid 40V, Positive-QTOF	splash10-00xr-5352900000-ae971104cf608ea3ce10	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 18alpha-Hydroxyglycyrrhetic acid 10V, Negative-QTOF	splash10-000i-0000900000-20d08b5715a8fe73cbfc	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 18alpha-Hydroxyglycyrrhetic acid 20V, Negative-QTOF	splash10-00y3-0000900000-4fa2009950b40dd6e1f0	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 18alpha-Hydroxyglycyrrhetic acid 40V, Negative-QTOF	splash10-00ou-2001900000-ccc7d3c0f909b4769f19	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 18alpha-Hydroxyglycyrrhetic acid 10V, Positive-QTOF	splash10-000i-0000900000-54af6e1e651b319692d3	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 18alpha-Hydroxyglycyrrhetic acid 20V, Positive-QTOF	splash10-01dr-0100900000-ba817cdf63a77b3dee2d	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 18alpha-Hydroxyglycyrrhetic acid 40V, Positive-QTOF	splash10-014r-5985200000-4e784a68cfa44acdee75	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 18alpha-Hydroxyglycyrrhetic acid 10V, Negative-QTOF	splash10-000i-0000900000-6a75a140e72d68a6c193	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 18alpha-Hydroxyglycyrrhetic acid 20V, Negative-QTOF	splash10-000i-0000900000-bb75148d629eb4e4973a	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 18alpha-Hydroxyglycyrrhetic acid 40V, Negative-QTOF	splash10-000i-0000900000-8c9b45ee368045fc119b	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

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

FDB020262

KNApSAcK ID

Not Available

Chemspider ID

35014951

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

14189465

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1883871

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

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 ]
Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Showing metabocard for 18alpha-Hydroxyglycyrrhetic acid (HMDB0040499)

MOL for HMDB0040499 (18alpha-Hydroxyglycyrrhetic acid)

3D MOL for HMDB0040499 (18alpha-Hydroxyglycyrrhetic acid)

3D SDF for HMDB0040499 (18alpha-Hydroxyglycyrrhetic acid)

3D-SDF for HMDB0040499 (18alpha-Hydroxyglycyrrhetic acid)

PDB for HMDB0040499 (18alpha-Hydroxyglycyrrhetic acid)

3D PDB for HMDB0040499 (18alpha-Hydroxyglycyrrhetic acid)

SMILES for HMDB0040499 (18alpha-Hydroxyglycyrrhetic acid)

INCHI for HMDB0040499 (18alpha-Hydroxyglycyrrhetic acid)

Structure for HMDB0040499 (18alpha-Hydroxyglycyrrhetic acid)

3D Structure for HMDB0040499 (18alpha-Hydroxyglycyrrhetic acid)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra