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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 19:21:51 UTC

Update Date

2022-03-07 02:54:08 UTC

HMDB ID

HMDB0034512

Secondary Accession Numbers

HMDB34512

Metabolite Identification

Common Name

Liquoric acid

Description

Liquoric acid, also known as liquate, 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 Liquoric acid.

Structure

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


  Mrv0541 02241216332D          

 36 41  0  0  0  0            999 V2000
   -4.3018   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0163   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0163   -3.3000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.3018   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5873   -3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5873   -2.4750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.8729   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8729   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1584   -3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1584   -2.4750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1584   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8729   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.5873   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.8046   -1.5086    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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  3 23  1  1  0  0  0
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  6 26  1  1  0  0  0
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 15 34  1  1  0  0  0
 18 35  1  1  0  0  0
 22 36  1  6  0  0  0
 17 36  1  6  0  0  0
M  END

HMDB0034512
     RDKit          3D
Liquoric acid
 79 84  0  0  0  0  0  0  0  0999 V2000
   -5.2008   -1.8700   -0.6633 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5894   -0.5716   -1.0789 C   0  0  0  0  0  0  0  0  0  0  0  0
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 32 75  1  0
 33 76  1  0
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 34 78  1  6
 35 79  1  0
M  END


  Mrv0541 02241216332D          

 36 41  0  0  0  0            999 V2000
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  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  1  6  1  0  0  0  0
  7  6  1  0  0  0  0
  6  5  1  0  0  0  0
  5  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 13  1  0  0  0  0
  7 10  1  0  0  0  0
 12  7  1  0  0  0  0
 11 12  1  0  0  0  0
 11 14  2  0  0  0  0
 15 14  1  0  0  0  0
 14 13  1  0  0  0  0
 13 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 20 15  1  0  0  0  0
 15 18  1  0  0  0  0
 18 21  1  0  0  0  0
 19 20  1  0  0  0  0
 21 22  1  0  0  0  0
 19 22  1  0  0  0  0
  3 23  1  1  0  0  0
  4 24  1  0  0  0  0
  4 25  1  0  0  0  0
  6 26  1  1  0  0  0
 10 27  1  1  0  0  0
 12 28  2  0  0  0  0
 13 29  1  6  0  0  0
 19 30  1  1  0  0  0
 19 31  1  6  0  0  0
 30 32  2  0  0  0  0
 30 33  1  0  0  0  0
 15 34  1  1  0  0  0
 18 35  1  1  0  0  0
 22 36  1  6  0  0  0
 17 36  1  6  0  0  0
M  END
> <DATABASE_ID>
HMDB0034512

> <DATABASE_NAME>
hmdb

> <SMILES>
[H][C@@]12C[C@](C)([C@H]3C[C@]1(C)[C@@H](C[C@]1(C)C2=CC(=O)C2[C@@]4(C)CC[C@H](O)C(C)(C)C4CC[C@@]12C)O3)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C30H44O5/c1-25(2)19-8-11-29(6)23(26(19,3)10-9-20(25)32)18(31)12-16-17-13-28(5,24(33)34)21-14-27(17,4)22(35-21)15-30(16,29)7/h12,17,19-23,32H,8-11,13-15H2,1-7H3,(H,33,34)/t17-,19?,20-,21+,22+,23?,26-,27-,28+,29+,30+/m0/s1

> <INCHI_KEY>
NGWKGSCSHDHHAJ-YPFQVHCOSA-N

> <FORMULA>
C30H44O5

> <MOLECULAR_WEIGHT>
484.6674

> <EXACT_MASS>
484.318874518

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
55.37410793448764

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,3S,4R,9S,12S,17S,19R,20R,22S)-9-hydroxy-3,4,8,8,12,19,22-heptamethyl-14-oxo-23-oxahexacyclo[18.2.1.0³,¹⁶.0⁴,¹³.0⁷,¹².0¹⁷,²²]tricos-15-ene-19-carboxylic acid

> <ALOGPS_LOGP>
4.24

> <JCHEM_LOGP>
4.731409474666665

> <ALOGPS_LOGS>
-5.26

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
17.92663953902153

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.239294571523967

> <JCHEM_PKA_STRONGEST_BASIC>
-0.8349132512870444

> <JCHEM_POLAR_SURFACE_AREA>
83.83

> <JCHEM_REFRACTIVITY>
133.78939999999994

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.67e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,3S,4R,9S,12S,17S,19R,20R,22S)-9-hydroxy-3,4,8,8,12,19,22-heptamethyl-14-oxo-23-oxahexacyclo[18.2.1.0³,¹⁶.0⁴,¹³.0⁷,¹².0¹⁷,²²]tricos-15-ene-19-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0034512
     RDKit          3D
Liquoric acid
 79 84  0  0  0  0  0  0  0  0999 V2000
   -5.2008   -1.8700   -0.6633 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5894   -0.5716   -1.0789 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6783   -0.5198   -2.6181 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1359   -0.3991   -0.7549 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3849   -1.6123   -1.1434 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8933   -1.2479   -1.1342 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4639   -0.7292    0.2504 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6465   -1.9939    1.1194 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3590    0.3738    0.6943 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9227    1.5345   -0.1278 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6004    2.2692   -0.8514 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5381    1.8599   -0.0737 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4393    0.9148    0.0985 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8577    1.3972    0.1369 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.7172    1.1460   -1.0031 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0490    0.4669   -0.7501 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.2282   -0.6348   -1.7710 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2071    1.3627   -0.8947 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0917    1.5608   -0.0310 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3518    2.0637   -2.0980 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0998   -0.1841    0.6163 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.8609    0.9564    1.6075 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3495    0.9350    1.5062 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.7613    1.7203    2.6310 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1067   -0.5494    1.6282 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7043   -0.9631    1.4937 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9960   -0.4582    0.2238 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5683   -1.3920   -0.8401 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0702   -1.0888    0.8481 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8247    0.1774    0.5718 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.3757   -0.6512    1.7526 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6052    1.4942    0.6715 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5430    1.7698   -0.4330 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4574    0.5770   -0.6018 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.1439    0.2088    0.5212 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5158   -2.7043   -0.5383 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8963   -1.7444    0.2187 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9187   -2.2100   -1.4752 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7002   -0.2274   -2.9294 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9193    0.1889   -3.0162 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4649   -1.5131   -3.0353 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7726    0.3903   -1.4978 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5942   -1.7669   -2.2494 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5332   -2.5220   -0.5797 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4044   -2.2143   -1.3598 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6597   -0.5540   -1.9343 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6807   -2.3508    1.1531 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1670   -2.8471    0.6001 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3098   -1.8432    2.1543 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1442    0.5438    1.7763 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7737    2.9092   -0.1864 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8473    2.5268    0.3012 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1399    0.6796   -1.8447 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0309    2.1166   -1.5212 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9913   -1.6301   -1.3199 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2938   -0.6554   -2.0687 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6403   -0.4521   -2.6924 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5536    1.6375   -2.9705 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1058   -0.6237    0.7275 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1349    0.6201    2.6245 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2905    1.9063    1.3141 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4846    2.7286    2.2219 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8962    1.2204    3.0901 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5091    1.9033    3.4417 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4013   -0.7856    2.6990 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1612   -0.5486    2.3988 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6156   -2.0482    1.5451 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3728   -2.4144   -0.4604 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2416   -1.1737   -1.8531 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6577   -1.4062   -0.8865 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8794   -1.5569    1.4562 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1650   -0.0754    2.3220 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6006   -0.7411    2.5567 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9579    2.3404    0.9825 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3010    1.4699    1.5817 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2178    2.5975   -0.0845 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1463    2.0336   -1.4207 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2545    0.8066   -1.3794 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1106    0.0671    0.4014 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
 25 29  1  0
  9 30  1  0
 30 31  1  1
 30 32  1  0
 32 33  1  0
 33 34  1  0
 34 35  1  0
 34  2  1  0
 30  4  1  0
 27  7  1  0
 27 13  1  0
 23 14  1  0
 29 21  1  0
  1 36  1  0
  1 37  1  0
  1 38  1  0
  3 39  1  0
  3 40  1  0
  3 41  1  0
  4 42  1  0
  5 43  1  0
  5 44  1  0
  6 45  1  0
  6 46  1  0
  8 47  1  0
  8 48  1  0
  8 49  1  0
  9 50  1  0
 12 51  1  0
 14 52  1  1
 15 53  1  0
 15 54  1  0
 17 55  1  0
 17 56  1  0
 17 57  1  0
 20 58  1  0
 21 59  1  1
 22 60  1  0
 22 61  1  0
 24 62  1  0
 24 63  1  0
 24 64  1  0
 25 65  1  1
 26 66  1  0
 26 67  1  0
 28 68  1  0
 28 69  1  0
 28 70  1  0
 31 71  1  0
 31 72  1  0
 31 73  1  0
 32 74  1  0
 32 75  1  0
 33 76  1  0
 33 77  1  0
 34 78  1  6
 35 79  1  0
M  END

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      -8.030  -3.850   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -9.364  -4.620   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -9.364  -6.160   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -8.030  -6.930   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -6.696  -6.160   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -6.696  -4.620   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -5.363  -3.850   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -5.363  -6.930   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -4.029  -6.160   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -4.029  -4.620   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -4.029  -1.540   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -5.363  -2.310   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -2.695  -3.850   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -2.695  -2.310   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -1.362  -1.540   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -1.362  -4.620   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -0.028  -3.850   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -0.028  -2.310   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -0.028   0.770   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -1.362   0.000   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       1.306  -1.540   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       1.306   0.000   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0     -10.697  -6.930   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      -9.119  -8.019   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -7.260  -8.264   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -6.696  -3.080   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -4.029  -3.080   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      -6.696  -1.540   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      -2.695  -5.390   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       1.306   1.540   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -1.117   1.859   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       1.306   3.080   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0       2.639   0.770   0.000  0.00  0.00           O+0
HETATM   34  H   UNK     0      -2.695  -0.770   0.000  0.00  0.00           H+0
HETATM   35  C   UNK     0       1.306  -3.080   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0      -1.502  -2.816   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4   23                                                  
CONECT    4    3    5   24   25                                             
CONECT    5    4    6    8                                                  
CONECT    6    1    7    5   26                                             
CONECT    7    6   10   12                                                  
CONECT    8    5    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   13    7   27                                             
CONECT   11   12   14                                                       
CONECT   12    7   11   28                                                  
CONECT   13   10   14   16   29                                             
CONECT   14   11   15   13                                                  
CONECT   15   14   20   18   34                                             
CONECT   16   13   17                                                       
CONECT   17   16   18   36                                                  
CONECT   18   17   15   21   35                                             
CONECT   19   20   22   30   31                                             
CONECT   20   15   19                                                       
CONECT   21   18   22                                                       
CONECT   22   21   19   36                                                  
CONECT   23    3                                                            
CONECT   24    4                                                            
CONECT   25    4                                                            
CONECT   26    6                                                            
CONECT   27   10                                                            
CONECT   28   12                                                            
CONECT   29   13                                                            
CONECT   30   19   32   33                                                  
CONECT   31   19                                                            
CONECT   32   30                                                            
CONECT   33   30                                                            
CONECT   34   15                                                            
CONECT   35   18                                                            
CONECT   36   22   17                                                       
MASTER        0    0    0    0    0    0    0    0   36    0   82    0
END

COMPND    HMDB0034512
HETATM    1  C1  UNL     1      -5.201  -1.870  -0.663  1.00  0.00           C  
HETATM    2  C2  UNL     1      -4.589  -0.572  -1.079  1.00  0.00           C  
HETATM    3  C3  UNL     1      -4.678  -0.520  -2.618  1.00  0.00           C  
HETATM    4  C4  UNL     1      -3.136  -0.399  -0.755  1.00  0.00           C  
HETATM    5  C5  UNL     1      -2.385  -1.612  -1.143  1.00  0.00           C  
HETATM    6  C6  UNL     1      -0.893  -1.248  -1.134  1.00  0.00           C  
HETATM    7  C7  UNL     1      -0.464  -0.729   0.250  1.00  0.00           C  
HETATM    8  C8  UNL     1      -0.646  -1.994   1.119  1.00  0.00           C  
HETATM    9  C9  UNL     1      -1.359   0.374   0.694  1.00  0.00           C  
HETATM   10  C10 UNL     1      -0.923   1.534  -0.128  1.00  0.00           C  
HETATM   11  O1  UNL     1      -1.600   2.269  -0.851  1.00  0.00           O  
HETATM   12  C11 UNL     1       0.538   1.860  -0.074  1.00  0.00           C  
HETATM   13  C12 UNL     1       1.439   0.915   0.099  1.00  0.00           C  
HETATM   14  C13 UNL     1       2.858   1.397   0.137  1.00  0.00           C  
HETATM   15  C14 UNL     1       3.717   1.146  -1.003  1.00  0.00           C  
HETATM   16  C15 UNL     1       5.049   0.467  -0.750  1.00  0.00           C  
HETATM   17  C16 UNL     1       5.228  -0.635  -1.771  1.00  0.00           C  
HETATM   18  C17 UNL     1       6.207   1.363  -0.895  1.00  0.00           C  
HETATM   19  O2  UNL     1       7.092   1.561  -0.031  1.00  0.00           O  
HETATM   20  O3  UNL     1       6.352   2.064  -2.098  1.00  0.00           O  
HETATM   21  C18 UNL     1       5.100  -0.184   0.616  1.00  0.00           C  
HETATM   22  C19 UNL     1       4.861   0.956   1.608  1.00  0.00           C  
HETATM   23  C20 UNL     1       3.350   0.935   1.506  1.00  0.00           C  
HETATM   24  C21 UNL     1       2.761   1.720   2.631  1.00  0.00           C  
HETATM   25  C22 UNL     1       3.107  -0.549   1.628  1.00  0.00           C  
HETATM   26  C23 UNL     1       1.704  -0.963   1.494  1.00  0.00           C  
HETATM   27  C24 UNL     1       0.996  -0.458   0.224  1.00  0.00           C  
HETATM   28  C25 UNL     1       1.568  -1.392  -0.840  1.00  0.00           C  
HETATM   29  O4  UNL     1       4.070  -1.089   0.848  1.00  0.00           O  
HETATM   30  C26 UNL     1      -2.825   0.177   0.572  1.00  0.00           C  
HETATM   31  C27 UNL     1      -3.376  -0.651   1.753  1.00  0.00           C  
HETATM   32  C28 UNL     1      -3.605   1.494   0.672  1.00  0.00           C  
HETATM   33  C29 UNL     1      -4.543   1.770  -0.433  1.00  0.00           C  
HETATM   34  C30 UNL     1      -5.457   0.577  -0.602  1.00  0.00           C  
HETATM   35  O5  UNL     1      -6.144   0.209   0.521  1.00  0.00           O  
HETATM   36  H1  UNL     1      -4.516  -2.704  -0.538  1.00  0.00           H  
HETATM   37  H2  UNL     1      -5.896  -1.744   0.219  1.00  0.00           H  
HETATM   38  H3  UNL     1      -5.919  -2.210  -1.475  1.00  0.00           H  
HETATM   39  H4  UNL     1      -5.700  -0.227  -2.929  1.00  0.00           H  
HETATM   40  H5  UNL     1      -3.919   0.189  -3.016  1.00  0.00           H  
HETATM   41  H6  UNL     1      -4.465  -1.513  -3.035  1.00  0.00           H  
HETATM   42  H7  UNL     1      -2.773   0.390  -1.498  1.00  0.00           H  
HETATM   43  H8  UNL     1      -2.594  -1.767  -2.249  1.00  0.00           H  
HETATM   44  H9  UNL     1      -2.533  -2.522  -0.580  1.00  0.00           H  
HETATM   45  H10 UNL     1      -0.404  -2.214  -1.360  1.00  0.00           H  
HETATM   46  H11 UNL     1      -0.660  -0.554  -1.934  1.00  0.00           H  
HETATM   47  H12 UNL     1      -1.681  -2.351   1.153  1.00  0.00           H  
HETATM   48  H13 UNL     1      -0.167  -2.847   0.600  1.00  0.00           H  
HETATM   49  H14 UNL     1      -0.310  -1.843   2.154  1.00  0.00           H  
HETATM   50  H15 UNL     1      -1.144   0.544   1.776  1.00  0.00           H  
HETATM   51  H16 UNL     1       0.774   2.909  -0.186  1.00  0.00           H  
HETATM   52  H17 UNL     1       2.847   2.527   0.301  1.00  0.00           H  
HETATM   53  H18 UNL     1       3.140   0.680  -1.845  1.00  0.00           H  
HETATM   54  H19 UNL     1       4.031   2.117  -1.521  1.00  0.00           H  
HETATM   55  H20 UNL     1       4.991  -1.630  -1.320  1.00  0.00           H  
HETATM   56  H21 UNL     1       6.294  -0.655  -2.069  1.00  0.00           H  
HETATM   57  H22 UNL     1       4.640  -0.452  -2.692  1.00  0.00           H  
HETATM   58  H23 UNL     1       6.554   1.637  -2.971  1.00  0.00           H  
HETATM   59  H24 UNL     1       6.106  -0.624   0.728  1.00  0.00           H  
HETATM   60  H25 UNL     1       5.135   0.620   2.624  1.00  0.00           H  
HETATM   61  H26 UNL     1       5.290   1.906   1.314  1.00  0.00           H  
HETATM   62  H27 UNL     1       2.485   2.729   2.222  1.00  0.00           H  
HETATM   63  H28 UNL     1       1.896   1.220   3.090  1.00  0.00           H  
HETATM   64  H29 UNL     1       3.509   1.903   3.442  1.00  0.00           H  
HETATM   65  H30 UNL     1       3.401  -0.786   2.699  1.00  0.00           H  
HETATM   66  H31 UNL     1       1.161  -0.549   2.399  1.00  0.00           H  
HETATM   67  H32 UNL     1       1.616  -2.048   1.545  1.00  0.00           H  
HETATM   68  H33 UNL     1       1.373  -2.414  -0.460  1.00  0.00           H  
HETATM   69  H34 UNL     1       1.242  -1.174  -1.853  1.00  0.00           H  
HETATM   70  H35 UNL     1       2.658  -1.406  -0.886  1.00  0.00           H  
HETATM   71  H36 UNL     1      -3.879  -1.557   1.456  1.00  0.00           H  
HETATM   72  H37 UNL     1      -4.165  -0.075   2.322  1.00  0.00           H  
HETATM   73  H38 UNL     1      -2.601  -0.741   2.557  1.00  0.00           H  
HETATM   74  H39 UNL     1      -2.958   2.340   0.982  1.00  0.00           H  
HETATM   75  H40 UNL     1      -4.301   1.470   1.582  1.00  0.00           H  
HETATM   76  H41 UNL     1      -5.218   2.598  -0.084  1.00  0.00           H  
HETATM   77  H42 UNL     1      -4.146   2.034  -1.421  1.00  0.00           H  
HETATM   78  H43 UNL     1      -6.255   0.807  -1.379  1.00  0.00           H  
HETATM   79  H44 UNL     1      -7.111   0.067   0.401  1.00  0.00           H  
CONECT    1    2   36   37   38
CONECT    2    3    4   34
CONECT    3   39   40   41
CONECT    4    5   30   42
CONECT    5    6   43   44
CONECT    6    7   45   46
CONECT    7    8    9   27
CONECT    8   47   48   49
CONECT    9   10   30   50
CONECT   10   11   11   12
CONECT   12   13   13   51
CONECT   13   14   27
CONECT   14   15   23   52
CONECT   15   16   53   54
CONECT   16   17   18   21
CONECT   17   55   56   57
CONECT   18   19   19   20
CONECT   20   58
CONECT   21   22   29   59
CONECT   22   23   60   61
CONECT   23   24   25
CONECT   24   62   63   64
CONECT   25   26   29   65
CONECT   26   27   66   67
CONECT   27   28
CONECT   28   68   69   70
CONECT   30   31   32
CONECT   31   71   72   73
CONECT   32   33   74   75
CONECT   33   34   76   77
CONECT   34   35   78
CONECT   35   79
END

HMDB0034512
     RDKit          3D
Liquoric acid
 79 84  0  0  0  0  0  0  0  0999 V2000
   -5.2008   -1.8700   -0.6633 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5894   -0.5716   -1.0789 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6783   -0.5198   -2.6181 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1359   -0.3991   -0.7549 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3849   -1.6123   -1.1434 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8933   -1.2479   -1.1342 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4639   -0.7292    0.2504 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6465   -1.9939    1.1194 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3590    0.3738    0.6943 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9227    1.5345   -0.1278 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6004    2.2692   -0.8514 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5381    1.8599   -0.0737 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4393    0.9148    0.0985 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8577    1.3972    0.1369 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.7172    1.1460   -1.0031 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0490    0.4669   -0.7501 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.2282   -0.6348   -1.7710 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2071    1.3627   -0.8947 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0917    1.5608   -0.0310 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3518    2.0637   -2.0980 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0998   -0.1841    0.6163 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.8609    0.9564    1.6075 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3495    0.9350    1.5062 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.7613    1.7203    2.6310 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1067   -0.5494    1.6282 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7043   -0.9631    1.4937 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9960   -0.4582    0.2238 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5683   -1.3920   -0.8401 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0702   -1.0888    0.8481 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8247    0.1774    0.5718 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.3757   -0.6512    1.7526 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6052    1.4942    0.6715 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5430    1.7698   -0.4330 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4574    0.5770   -0.6018 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.1439    0.2088    0.5212 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5158   -2.7043   -0.5383 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8963   -1.7444    0.2187 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9187   -2.2100   -1.4752 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7002   -0.2274   -2.9294 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9193    0.1889   -3.0162 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4649   -1.5131   -3.0353 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7726    0.3903   -1.4978 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5942   -1.7669   -2.2494 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5332   -2.5220   -0.5797 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4044   -2.2143   -1.3598 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6597   -0.5540   -1.9343 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6807   -2.3508    1.1531 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1670   -2.8471    0.6001 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3098   -1.8432    2.1543 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1442    0.5438    1.7763 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7737    2.9092   -0.1864 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8473    2.5268    0.3012 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1399    0.6796   -1.8447 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0309    2.1166   -1.5212 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9913   -1.6301   -1.3199 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2938   -0.6554   -2.0687 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6403   -0.4521   -2.6924 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5536    1.6375   -2.9705 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1058   -0.6237    0.7275 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1349    0.6201    2.6245 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2905    1.9063    1.3141 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4846    2.7286    2.2219 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8962    1.2204    3.0901 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5091    1.9033    3.4417 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4013   -0.7856    2.6990 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1612   -0.5486    2.3988 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6156   -2.0482    1.5451 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3728   -2.4144   -0.4604 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2416   -1.1737   -1.8531 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6577   -1.4062   -0.8865 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8794   -1.5569    1.4562 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1650   -0.0754    2.3220 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6006   -0.7411    2.5567 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9579    2.3404    0.9825 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3010    1.4699    1.5817 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2178    2.5975   -0.0845 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1463    2.0336   -1.4207 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2545    0.8066   -1.3794 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1106    0.0671    0.4014 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
 25 29  1  0
  9 30  1  0
 30 31  1  1
 30 32  1  0
 32 33  1  0
 33 34  1  0
 34 35  1  0
 34  2  1  0
 30  4  1  0
 27  7  1  0
 27 13  1  0
 23 14  1  0
 29 21  1  0
  1 36  1  0
  1 37  1  0
  1 38  1  0
  3 39  1  0
  3 40  1  0
  3 41  1  0
  4 42  1  0
  5 43  1  0
  5 44  1  0
  6 45  1  0
  6 46  1  0
  8 47  1  0
  8 48  1  0
  8 49  1  0
  9 50  1  0
 12 51  1  0
 14 52  1  1
 15 53  1  0
 15 54  1  0
 17 55  1  0
 17 56  1  0
 17 57  1  0
 20 58  1  0
 21 59  1  1
 22 60  1  0
 22 61  1  0
 24 62  1  0
 24 63  1  0
 24 64  1  0
 25 65  1  1
 26 66  1  0
 26 67  1  0
 28 68  1  0
 28 69  1  0
 28 70  1  0
 31 71  1  0
 31 72  1  0
 31 73  1  0
 32 74  1  0
 32 75  1  0
 33 76  1  0
 33 77  1  0
 34 78  1  6
 35 79  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Liquate	Generator
Liquic acid	Generator
16,21-Epoxy-3-hydroxy-11-oxo-12-oleanen-30-Oic acid	HMDB
Licoric acid	HMDB
(1R,3S,4R,9S,12S,17S,19R,20R,22S)-9-Hydroxy-3,4,8,8,12,19,22-heptamethyl-14-oxo-23-oxahexacyclo[18.2.1.0³,¹⁶.0⁴,¹³.0⁷,¹².0¹⁷,²²]tricos-15-ene-19-carboxylate	Generator

Chemical Formula

C₃₀H₄₄O₅

Average Molecular Weight

484.6674

Monoisotopic Molecular Weight

484.318874518

IUPAC Name

(1R,3S,4R,9S,12S,17S,19R,20R,22S)-9-hydroxy-3,4,8,8,12,19,22-heptamethyl-14-oxo-23-oxahexacyclo[18.2.1.0³,¹⁶.0⁴,¹³.0⁷,¹².0¹⁷,²²]tricos-15-ene-19-carboxylic acid

Traditional Name

(1R,3S,4R,9S,12S,17S,19R,20R,22S)-9-hydroxy-3,4,8,8,12,19,22-heptamethyl-14-oxo-23-oxahexacyclo[18.2.1.0³,¹⁶.0⁴,¹³.0⁷,¹².0¹⁷,²²]tricos-15-ene-19-carboxylic acid

CAS Registry Number

Not Available

SMILES

[H][C@@]12C[C@](C)([C@H]3C[C@]1(C)[C@@H](C[C@]1(C)C2=CC(=O)C2[C@@]4(C)CC[C@H](O)C(C)(C)C4CC[C@@]12C)O3)C(O)=O

InChI Identifier

InChI=1S/C30H44O5/c1-25(2)19-8-11-29(6)23(26(19,3)10-9-20(25)32)18(31)12-16-17-13-28(5,24(33)34)21-14-27(17,4)22(35-21)15-30(16,29)7/h12,17,19-23,32H,8-11,13-15H2,1-7H3,(H,33,34)/t17-,19?,20-,21+,22+,23?,26-,27-,28+,29+,30+/m0/s1

InChI Key

NGWKGSCSHDHHAJ-YPFQVHCOSA-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
Naphthofuran
Cyclohexenone
Oxepane
Cyclic alcohol
Tetrahydrofuran
Ketone
Secondary alcohol
Carboxylic acid derivative
Carboxylic acid
Dialkyl ether
Ether
Monocarboxylic acid or derivatives
Oxacycle
Organoheterocyclic compound
Alcohol
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organic oxygen compound
Carbonyl group
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Route of exposure

Enteral

Ingestion (HMDB: HMDB0034512)

Source

Endogenous

Endogenous (HMDB: HMDB0034512)

Plant

Plant (HMDB: HMDB0034512)

Animal

Animal (HMDB: HMDB0034512)

Exogenous

Food

Food (HMDB: HMDB0034512)

Tea

Herb and spice

Herbs and Spices (FooDB: FOOD00866)

Exogenous (HMDB: HMDB0034512)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0034512)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0034512)

Lipid metabolism pathway (HMDB: HMDB0034512)

Cellular process

Cell signaling (HMDB: HMDB0034512)

Biochemical process

Lipid transport (HMDB: HMDB0034512)

Role

Biological role

Energy source (HMDB: HMDB0034512)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0034512)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	260 - 263 °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	0.0027 g/L	ALOGPS
logP	4.24	ALOGPS
logP	4.73	ChemAxon
logS	-5.3	ALOGPS
pKa (Strongest Acidic)	4.24	ChemAxon
pKa (Strongest Basic)	-0.83	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	83.83 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	133.79 m³·mol⁻¹	ChemAxon
Polarizability	55.37 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	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
DeepCCS	[M-2H]-	249.96	30932474
DeepCCS	[M+Na]+	223.978	30932474
AllCCS	[M+H]+	217.7	32859911
AllCCS	[M+H-H2O]+	216.2	32859911
AllCCS	[M+NH4]+	219.1	32859911
AllCCS	[M+Na]+	219.5	32859911
AllCCS	[M-H]-	215.1	32859911
AllCCS	[M+Na-2H]-	217.0	32859911
AllCCS	[M+HCOO]-	219.3	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.	8.75 minutes	32390414
Predicted by Siyang on May 30, 2022	19.1006 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.73 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	3390.1 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	304.0 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	253.1 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	172.0 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	418.5 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	883.4 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	914.2 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	89.9 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1467.1 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	639.0 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	1947.1 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	555.9 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	512.3 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	224.6 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	449.4 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	8.5 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Liquoric acid	[H][C@@]12C[C@](C)([C@H]3C[C@]1(C)[C@@H](C[C@]1(C)C2=CC(=O)C2[C@@]4(C)CC[C@H](O)C(C)(C)C4CC[C@@]12C)O3)C(O)=O	4210.0	Standard polar	33892256
Liquoric acid	[H][C@@]12C[C@](C)([C@H]3C[C@]1(C)[C@@H](C[C@]1(C)C2=CC(=O)C2[C@@]4(C)CC[C@H](O)C(C)(C)C4CC[C@@]12C)O3)C(O)=O	3493.7	Standard non polar	33892256
Liquoric acid	[H][C@@]12C[C@](C)([C@H]3C[C@]1(C)[C@@H](C[C@]1(C)C2=CC(=O)C2[C@@]4(C)CC[C@H](O)C(C)(C)C4CC[C@@]12C)O3)C(O)=O	4081.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Liquoric acid,1TMS,isomer #1	CC1(C)C2CC[C@]3(C)C(C(=O)C=C4[C@@H]5C[C@@](C)(C(=O)O)[C@H]6C[C@]5(C)[C@@H](C[C@]43C)O6)[C@@]2(C)CC[C@@H]1O[Si](C)(C)C	3928.9	Semi standard non polar	33892256
Liquoric acid,1TMS,isomer #2	CC1(C)C2CC[C@]3(C)C(C(=O)C=C4[C@@H]5C[C@@](C)(C(=O)O[Si](C)(C)C)[C@H]6C[C@]5(C)[C@@H](C[C@]43C)O6)[C@@]2(C)CC[C@@H]1O	3882.9	Semi standard non polar	33892256
Liquoric acid,1TMS,isomer #3	CC1(C)C2CC[C@]3(C)C(=C(O[Si](C)(C)C)C=C4[C@@H]5C[C@@](C)(C(=O)O)[C@H]6C[C@]5(C)[C@@H](C[C@]43C)O6)[C@@]2(C)CC[C@@H]1O	3822.8	Semi standard non polar	33892256
Liquoric acid,2TMS,isomer #1	CC1(C)C2CC[C@]3(C)C(C(=O)C=C4[C@@H]5C[C@@](C)(C(=O)O[Si](C)(C)C)[C@H]6C[C@]5(C)[C@@H](C[C@]43C)O6)[C@@]2(C)CC[C@@H]1O[Si](C)(C)C	3820.1	Semi standard non polar	33892256
Liquoric acid,2TMS,isomer #2	CC1(C)C2CC[C@]3(C)C(=C(O[Si](C)(C)C)C=C4[C@@H]5C[C@@](C)(C(=O)O)[C@H]6C[C@]5(C)[C@@H](C[C@]43C)O6)[C@@]2(C)CC[C@@H]1O[Si](C)(C)C	3752.5	Semi standard non polar	33892256
Liquoric acid,2TMS,isomer #3	CC1(C)C2CC[C@]3(C)C(=C(O[Si](C)(C)C)C=C4[C@@H]5C[C@@](C)(C(=O)O[Si](C)(C)C)[C@H]6C[C@]5(C)[C@@H](C[C@]43C)O6)[C@@]2(C)CC[C@@H]1O	3741.8	Semi standard non polar	33892256
Liquoric acid,3TMS,isomer #1	CC1(C)C2CC[C@]3(C)C(=C(O[Si](C)(C)C)C=C4[C@@H]5C[C@@](C)(C(=O)O[Si](C)(C)C)[C@H]6C[C@]5(C)[C@@H](C[C@]43C)O6)[C@@]2(C)CC[C@@H]1O[Si](C)(C)C	3664.9	Semi standard non polar	33892256
Liquoric acid,3TMS,isomer #1	CC1(C)C2CC[C@]3(C)C(=C(O[Si](C)(C)C)C=C4[C@@H]5C[C@@](C)(C(=O)O[Si](C)(C)C)[C@H]6C[C@]5(C)[C@@H](C[C@]43C)O6)[C@@]2(C)CC[C@@H]1O[Si](C)(C)C	3697.2	Standard non polar	33892256
Liquoric acid,1TBDMS,isomer #1	CC1(C)C2CC[C@]3(C)C(C(=O)C=C4[C@@H]5C[C@@](C)(C(=O)O)[C@H]6C[C@]5(C)[C@@H](C[C@]43C)O6)[C@@]2(C)CC[C@@H]1O[Si](C)(C)C(C)(C)C	4151.5	Semi standard non polar	33892256
Liquoric acid,1TBDMS,isomer #2	CC1(C)C2CC[C@]3(C)C(C(=O)C=C4[C@@H]5C[C@@](C)(C(=O)O[Si](C)(C)C(C)(C)C)[C@H]6C[C@]5(C)[C@@H](C[C@]43C)O6)[C@@]2(C)CC[C@@H]1O	4123.1	Semi standard non polar	33892256
Liquoric acid,1TBDMS,isomer #3	CC1(C)C2CC[C@]3(C)C(=C(O[Si](C)(C)C(C)(C)C)C=C4[C@@H]5C[C@@](C)(C(=O)O)[C@H]6C[C@]5(C)[C@@H](C[C@]43C)O6)[C@@]2(C)CC[C@@H]1O	4064.5	Semi standard non polar	33892256
Liquoric acid,2TBDMS,isomer #1	CC1(C)C2CC[C@]3(C)C(C(=O)C=C4[C@@H]5C[C@@](C)(C(=O)O[Si](C)(C)C(C)(C)C)[C@H]6C[C@]5(C)[C@@H](C[C@]43C)O6)[C@@]2(C)CC[C@@H]1O[Si](C)(C)C(C)(C)C	4275.3	Semi standard non polar	33892256
Liquoric acid,2TBDMS,isomer #2	CC1(C)C2CC[C@]3(C)C(=C(O[Si](C)(C)C(C)(C)C)C=C4[C@@H]5C[C@@](C)(C(=O)O)[C@H]6C[C@]5(C)[C@@H](C[C@]43C)O6)[C@@]2(C)CC[C@@H]1O[Si](C)(C)C(C)(C)C	4176.6	Semi standard non polar	33892256
Liquoric acid,2TBDMS,isomer #3	CC1(C)C2CC[C@]3(C)C(=C(O[Si](C)(C)C(C)(C)C)C=C4[C@@H]5C[C@@](C)(C(=O)O[Si](C)(C)C(C)(C)C)[C@H]6C[C@]5(C)[C@@H](C[C@]43C)O6)[C@@]2(C)CC[C@@H]1O	4184.5	Semi standard non polar	33892256
Liquoric acid,3TBDMS,isomer #1	CC1(C)C2CC[C@]3(C)C(=C(O[Si](C)(C)C(C)(C)C)C=C4[C@@H]5C[C@@](C)(C(=O)O[Si](C)(C)C(C)(C)C)[C@H]6C[C@]5(C)[C@@H](C[C@]43C)O6)[C@@]2(C)CC[C@@H]1O[Si](C)(C)C(C)(C)C	4290.0	Semi standard non polar	33892256
Liquoric acid,3TBDMS,isomer #1	CC1(C)C2CC[C@]3(C)C(=C(O[Si](C)(C)C(C)(C)C)C=C4[C@@H]5C[C@@](C)(C(=O)O[Si](C)(C)C(C)(C)C)[C@H]6C[C@]5(C)[C@@H](C[C@]43C)O6)[C@@]2(C)CC[C@@H]1O[Si](C)(C)C(C)(C)C	4388.5	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Liquoric acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-014j-0326900000-48d437fc747bc9d921f2	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Liquoric acid GC-MS (2 TMS) - 70eV, Positive	splash10-03di-2042429000-27682d63c2bc6a27d445	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Liquoric 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 - Liquoric acid 10V, Positive-QTOF	splash10-014r-0000900000-dd448cd448ce7d0f4004	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Liquoric acid 20V, Positive-QTOF	splash10-01bj-0010900000-eb785e7b2bf0a7f01521	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Liquoric acid 40V, Positive-QTOF	splash10-00kr-3666900000-f6056144c9dac067fb89	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Liquoric acid 10V, Negative-QTOF	splash10-001i-0000900000-128f39741dfad7baae41	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Liquoric acid 20V, Negative-QTOF	splash10-0080-0000900000-c02d82ea232e457b67ba	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Liquoric acid 40V, Negative-QTOF	splash10-00di-0001900000-b6be20c58a77bc078449	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Liquoric acid 10V, Negative-QTOF	splash10-001i-0000900000-424bba629934fef50ccd	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Liquoric acid 20V, Negative-QTOF	splash10-001i-0000900000-34775030bf8ee283f0a9	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Liquoric acid 40V, Negative-QTOF	splash10-0016-4000900000-e05ddebed334712f8cda	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Liquoric acid 10V, Positive-QTOF	splash10-000i-0000900000-b935d139a68c7b2c6e60	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Liquoric acid 20V, Positive-QTOF	splash10-000i-0001900000-a214846e7e9419a8cf19	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Liquoric acid 40V, Positive-QTOF	splash10-000j-2459700000-c1898abd2b7789971c2e	2021-09-25	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

FDB013012

KNApSAcK ID

Not Available

Chemspider ID

35013730

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

131751571

PDB ID

Not Available

ChEBI ID

168151

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)

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 Liquoric acid (HMDB0034512)

MOL for HMDB0034512 (Liquoric acid)

3D MOL for HMDB0034512 (Liquoric acid)

3D SDF for HMDB0034512 (Liquoric acid)

3D-SDF for HMDB0034512 (Liquoric acid)

PDB for HMDB0034512 (Liquoric acid)

3D PDB for HMDB0034512 (Liquoric acid)

SMILES for HMDB0034512 (Liquoric acid)

INCHI for HMDB0034512 (Liquoric acid)

Structure for HMDB0034512 (Liquoric acid)

3D Structure for HMDB0034512 (Liquoric acid)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra