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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 20:12:01 UTC

Update Date

2022-03-07 02:54:26 UTC

HMDB ID

HMDB0035249

Secondary Accession Numbers

HMDB35249

Metabolite Identification

Common Name

Taraxinic acid glucosyl ester

Description

Taraxinic acid glucosyl ester belongs to the class of organic compounds known as germacranolides and derivatives. These are sesquiterpene lactones with a structure based on the germacranolide skeleton, characterized by a gamma lactone fused to a 1,7-dimethylcyclodec-1-ene moiety. Based on a literature review a small amount of articles have been published on Taraxinic acid glucosyl ester.

Structure

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

  Mrv0541 05061308192D          

 30 32  0  0  0  0            999 V2000
    5.0298    3.2521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8558   -0.0022    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6124    1.7084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7983    1.8420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9037    0.9365    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5668    0.4320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2755    1.2038    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6929    2.7476    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0233   -3.4273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5070    2.6139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8173    0.8219    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3809    0.2983    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4614    1.3375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1701    2.1093    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5461   -2.7891    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3602   -2.9228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8830   -2.2845    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5917   -1.5127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1279    1.2751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6722   -0.4735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7776   -1.3790    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3146   -4.1992    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6515   -3.6946    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.6971   -2.4182    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1145   -0.8745    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3561    0.9838    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1494   -1.1117    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3460    2.0708    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2548   -2.0172    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4863   -0.6072    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  1  0  0  0  0
  5  3  1  0  0  0  0
  7  6  1  0  0  0  0
 10  1  1  0  0  0  0
 10  4  1  0  0  0  0
 10  8  2  0  0  0  0
 11  2  2  0  0  0  0
 12  5  2  0  0  0  0
 12  6  1  0  0  0  0
 13  7  1  0  0  0  0
 13 11  1  0  0  0  0
 14  8  1  0  0  0  0
 14 13  1  0  0  0  0
 15  9  1  0  0  0  0
 16 15  1  0  0  0  0
 17 16  1  0  0  0  0
 18 17  1  0  0  0  0
 19 11  1  0  0  0  0
 20 12  1  0  0  0  0
 21 18  1  0  0  0  0
 22  9  1  0  0  0  0
 23 16  1  0  0  0  0
 24 17  1  0  0  0  0
 25 18  1  0  0  0  0
 26 19  2  0  0  0  0
 27 20  2  0  0  0  0
 28 14  1  0  0  0  0
 28 19  1  0  0  0  0
 29 15  1  0  0  0  0
 29 21  1  0  0  0  0
 30 20  1  0  0  0  0
 30 21  1  0  0  0  0
M  END

HMDB0035249
     RDKit          3D
Taraxinic acid glucosyl ester
 58 60  0  0  0  0  0  0  0  0999 V2000
   -2.5694    3.6451    3.6931 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9735    2.5266    3.1198 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7014    1.4307    3.7518 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7208    1.1510    4.9754 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3864    0.7290    2.7554 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6569    0.8759    1.5239 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6366    1.1729    0.4903 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6446    0.7133   -0.7275 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7192    1.1043   -1.6908 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5965   -0.1993   -1.1762 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5552    0.5291   -2.0415 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1945    0.1961   -1.6536 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5001    0.8503   -0.7422 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8876    0.4240   -0.4219 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5031    1.0705    0.4390 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4810   -0.6416   -1.0438 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8070   -1.0010   -0.6963 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8305   -2.3014   -0.1631 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0896   -2.4691    0.4066 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0954   -3.7477    1.2375 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1274   -3.6174    2.2249 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1849   -2.5150   -0.6120 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2673   -1.7810   -0.1311 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8007   -1.9338   -1.9392 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8922   -1.2587   -2.5298 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6448   -1.0071   -1.9256 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0724    0.3206   -2.1476 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1093    1.9869   -0.0558 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3697    1.6819    1.4257 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7893    2.1185    1.7130 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7423    3.8757    4.7326 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0399    4.3763    3.1133 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0749   -0.0313    1.4423 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4604    1.8602    0.7618 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2638    1.9728   -1.2675 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2366    1.4394   -2.6360 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4446    0.2827   -1.8515 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1170   -0.8209   -0.4193 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1075   -0.9467   -1.8601 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8378    1.5805   -2.0633 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6767    0.2037   -3.1254 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7082   -0.6643   -2.1540 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2475   -0.3503    0.0757 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2624   -1.6345    1.0993 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9236   -4.6404    0.6017 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0915   -3.8097    1.7170 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4040   -2.8240    2.7843 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5380   -3.5699   -0.6893 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3911   -1.8375    0.8344 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5831   -2.7806   -2.6267 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5624   -1.9463   -2.7952 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9658   -1.2215   -2.7985 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5127    0.4088   -3.0345 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9514    2.4742   -0.5256 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3055    2.7887   -0.0269 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7044    2.2178    2.1017 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2432    0.5878    1.6429 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1285    2.9560    1.0746 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 19 22  1  0
 22 23  1  0
 22 24  1  0
 24 25  1  0
 24 26  1  0
 26 27  1  0
 13 28  1  0
 28 29  1  0
 29 30  1  0
 30  2  1  0
 30  6  1  0
 26 17  1  0
  1 31  1  0
  1 32  1  0
  6 33  1  0
  7 34  1  0
  9 35  1  0
  9 36  1  0
  9 37  1  0
 10 38  1  0
 10 39  1  0
 11 40  1  0
 11 41  1  0
 12 42  1  0
 17 43  1  0
 19 44  1  0
 20 45  1  0
 20 46  1  0
 21 47  1  0
 22 48  1  0
 23 49  1  0
 24 50  1  0
 25 51  1  0
 26 52  1  0
 27 53  1  0
 28 54  1  0
 28 55  1  0
 29 56  1  0
 29 57  1  0
 30 58  1  0
M  END

  Mrv0541 05061308192D          

 30 32  0  0  0  0            999 V2000
    5.0298    3.2521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8558   -0.0022    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6124    1.7084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7983    1.8420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9037    0.9365    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5668    0.4320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2755    1.2038    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6929    2.7476    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0233   -3.4273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5070    2.6139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8173    0.8219    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3809    0.2983    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4614    1.3375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1701    2.1093    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5461   -2.7891    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3602   -2.9228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8830   -2.2845    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5917   -1.5127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1279    1.2751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6722   -0.4735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7776   -1.3790    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3146   -4.1992    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6515   -3.6946    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.6971   -2.4182    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1145   -0.8745    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3561    0.9838    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1494   -1.1117    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3460    2.0708    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2548   -2.0172    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4863   -0.6072    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  1  0  0  0  0
  5  3  1  0  0  0  0
  7  6  1  0  0  0  0
 10  1  1  0  0  0  0
 10  4  1  0  0  0  0
 10  8  2  0  0  0  0
 11  2  2  0  0  0  0
 12  5  2  0  0  0  0
 12  6  1  0  0  0  0
 13  7  1  0  0  0  0
 13 11  1  0  0  0  0
 14  8  1  0  0  0  0
 14 13  1  0  0  0  0
 15  9  1  0  0  0  0
 16 15  1  0  0  0  0
 17 16  1  0  0  0  0
 18 17  1  0  0  0  0
 19 11  1  0  0  0  0
 20 12  1  0  0  0  0
 21 18  1  0  0  0  0
 22  9  1  0  0  0  0
 23 16  1  0  0  0  0
 24 17  1  0  0  0  0
 25 18  1  0  0  0  0
 26 19  2  0  0  0  0
 27 20  2  0  0  0  0
 28 14  1  0  0  0  0
 28 19  1  0  0  0  0
 29 15  1  0  0  0  0
 29 21  1  0  0  0  0
 30 20  1  0  0  0  0
 30 21  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0035249

> <DATABASE_NAME>
hmdb

> <SMILES>
C\C1=C\C2OC(=O)C(=C)C2CC\C(=C/CC1)C(=O)OC1OC(CO)C(O)C(O)C1O

> <INCHI_IDENTIFIER>
InChI=1S/C21H28O9/c1-10-4-3-5-12(6-7-13-11(2)19(26)28-14(13)8-10)20(27)30-21-18(25)17(24)16(23)15(9-22)29-21/h5,8,13-18,21-25H,2-4,6-7,9H2,1H3/b10-8-,12-5+

> <INCHI_KEY>
SIOXYUXOHTZOOM-INAGUISBSA-N

> <FORMULA>
C21H28O9

> <MOLECULAR_WEIGHT>
424.4416

> <EXACT_MASS>
424.173332494

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_AVERAGE_POLARIZABILITY>
43.24060069671402

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl 10-methyl-3-methylidene-2-oxo-2H,3H,3aH,4H,5H,8H,9H,11aH-cyclodeca[b]furan-6-carboxylate

> <ALOGPS_LOGP>
-0.02

> <JCHEM_LOGP>
0.9731244856666676

> <ALOGPS_LOGS>
-2.36

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.194438902169743

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.195723010853209

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9810938228982016

> <JCHEM_POLAR_SURFACE_AREA>
142.75

> <JCHEM_REFRACTIVITY>
104.09479999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.84e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl 10-methyl-3-methylidene-2-oxo-3aH,4H,5H,8H,9H,11aH-cyclodeca[b]furan-6-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0035249
     RDKit          3D
Taraxinic acid glucosyl ester
 58 60  0  0  0  0  0  0  0  0999 V2000
   -2.5694    3.6451    3.6931 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9735    2.5266    3.1198 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7014    1.4307    3.7518 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7208    1.1510    4.9754 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3864    0.7290    2.7554 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6569    0.8759    1.5239 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6366    1.1729    0.4903 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6446    0.7133   -0.7275 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7192    1.1043   -1.6908 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5965   -0.1993   -1.1762 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5552    0.5291   -2.0415 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1945    0.1961   -1.6536 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5001    0.8503   -0.7422 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8876    0.4240   -0.4219 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5031    1.0705    0.4390 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4810   -0.6416   -1.0438 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8070   -1.0010   -0.6963 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8305   -2.3014   -0.1631 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0896   -2.4691    0.4066 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0954   -3.7477    1.2375 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1274   -3.6174    2.2249 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1849   -2.5150   -0.6120 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2673   -1.7810   -0.1311 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8007   -1.9338   -1.9392 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8922   -1.2587   -2.5298 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6448   -1.0071   -1.9256 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0724    0.3206   -2.1476 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1093    1.9869   -0.0558 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3697    1.6819    1.4257 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7893    2.1185    1.7130 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7423    3.8757    4.7326 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0399    4.3763    3.1133 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0749   -0.0313    1.4423 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4604    1.8602    0.7618 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2638    1.9728   -1.2675 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2366    1.4394   -2.6360 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4446    0.2827   -1.8515 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1170   -0.8209   -0.4193 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1075   -0.9467   -1.8601 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8378    1.5805   -2.0633 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6767    0.2037   -3.1254 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7082   -0.6643   -2.1540 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2475   -0.3503    0.0757 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2624   -1.6345    1.0993 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9236   -4.6404    0.6017 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0915   -3.8097    1.7170 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4040   -2.8240    2.7843 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5380   -3.5699   -0.6893 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3911   -1.8375    0.8344 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5831   -2.7806   -2.6267 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5624   -1.9463   -2.7952 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9658   -1.2215   -2.7985 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5127    0.4088   -3.0345 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9514    2.4742   -0.5256 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3055    2.7887   -0.0269 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7044    2.2178    2.1017 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2432    0.5878    1.6429 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1285    2.9560    1.0746 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 19 22  1  0
 22 23  1  0
 22 24  1  0
 24 25  1  0
 24 26  1  0
 26 27  1  0
 13 28  1  0
 28 29  1  0
 29 30  1  0
 30  2  1  0
 30  6  1  0
 26 17  1  0
  1 31  1  0
  1 32  1  0
  6 33  1  0
  7 34  1  0
  9 35  1  0
  9 36  1  0
  9 37  1  0
 10 38  1  0
 10 39  1  0
 11 40  1  0
 11 41  1  0
 12 42  1  0
 17 43  1  0
 19 44  1  0
 20 45  1  0
 20 46  1  0
 21 47  1  0
 22 48  1  0
 23 49  1  0
 24 50  1  0
 25 51  1  0
 26 52  1  0
 27 53  1  0
 28 54  1  0
 28 55  1  0
 29 56  1  0
 29 57  1  0
 30 58  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       9.389   6.071   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.331  -0.004   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      10.476   3.189   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.957   3.438   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      11.020   1.748   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.525   0.806   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.981   2.247   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.893   5.129   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      11.243  -6.398   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.413   4.879   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.259   1.534   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      10.044   0.557   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.461   2.497   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.918   3.937   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      12.219  -5.206   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      13.739  -5.456   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      14.715  -4.264   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      14.171  -2.824   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.972   2.380   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      10.588  -0.884   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      12.652  -2.574   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      11.787  -7.839   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      14.283  -6.897   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0      16.235  -4.514   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0      15.147  -1.632   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0       2.531   1.836   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0       9.612  -2.075   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0       4.379   3.865   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0      11.676  -3.765   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0      12.108  -1.133   0.000  0.00  0.00           O+0
CONECT    1   10                                                            
CONECT    2   11                                                            
CONECT    3    4    5                                                       
CONECT    4    3   10                                                       
CONECT    5    3   12                                                       
CONECT    6    7   12                                                       
CONECT    7    6   13                                                       
CONECT    8   10   14                                                       
CONECT    9   15   22                                                       
CONECT   10    1    4    8                                                  
CONECT   11    2   13   19                                                  
CONECT   12    5    6   20                                                  
CONECT   13    7   11   14                                                  
CONECT   14    8   13   28                                                  
CONECT   15    9   16   29                                                  
CONECT   16   15   17   23                                                  
CONECT   17   16   18   24                                                  
CONECT   18   17   21   25                                                  
CONECT   19   11   26   28                                                  
CONECT   20   12   27   30                                                  
CONECT   21   18   29   30                                                  
CONECT   22    9                                                            
CONECT   23   16                                                            
CONECT   24   17                                                            
CONECT   25   18                                                            
CONECT   26   19                                                            
CONECT   27   20                                                            
CONECT   28   14   19                                                       
CONECT   29   15   21                                                       
CONECT   30   20   21                                                       
MASTER        0    0    0    0    0    0    0    0   30    0   64    0
END

COMPND    HMDB0035249
HETATM    1  C1  UNL     1      -2.569   3.645   3.693  1.00  0.00           C  
HETATM    2  C2  UNL     1      -2.974   2.527   3.120  1.00  0.00           C  
HETATM    3  C3  UNL     1      -3.701   1.431   3.752  1.00  0.00           C  
HETATM    4  O1  UNL     1      -3.721   1.151   4.975  1.00  0.00           O  
HETATM    5  O2  UNL     1      -4.386   0.729   2.755  1.00  0.00           O  
HETATM    6  C4  UNL     1      -3.657   0.876   1.524  1.00  0.00           C  
HETATM    7  C5  UNL     1      -4.637   1.173   0.490  1.00  0.00           C  
HETATM    8  C6  UNL     1      -4.645   0.713  -0.728  1.00  0.00           C  
HETATM    9  C7  UNL     1      -5.719   1.104  -1.691  1.00  0.00           C  
HETATM   10  C8  UNL     1      -3.597  -0.199  -1.176  1.00  0.00           C  
HETATM   11  C9  UNL     1      -2.555   0.529  -2.041  1.00  0.00           C  
HETATM   12  C10 UNL     1      -1.194   0.196  -1.654  1.00  0.00           C  
HETATM   13  C11 UNL     1      -0.500   0.850  -0.742  1.00  0.00           C  
HETATM   14  C12 UNL     1       0.888   0.424  -0.422  1.00  0.00           C  
HETATM   15  O3  UNL     1       1.503   1.071   0.439  1.00  0.00           O  
HETATM   16  O4  UNL     1       1.481  -0.642  -1.044  1.00  0.00           O  
HETATM   17  C13 UNL     1       2.807  -1.001  -0.696  1.00  0.00           C  
HETATM   18  O5  UNL     1       2.831  -2.301  -0.163  1.00  0.00           O  
HETATM   19  C14 UNL     1       4.090  -2.469   0.407  1.00  0.00           C  
HETATM   20  C15 UNL     1       4.095  -3.748   1.238  1.00  0.00           C  
HETATM   21  O6  UNL     1       3.127  -3.617   2.225  1.00  0.00           O  
HETATM   22  C16 UNL     1       5.185  -2.515  -0.612  1.00  0.00           C  
HETATM   23  O7  UNL     1       6.267  -1.781  -0.131  1.00  0.00           O  
HETATM   24  C17 UNL     1       4.801  -1.934  -1.939  1.00  0.00           C  
HETATM   25  O8  UNL     1       5.892  -1.259  -2.530  1.00  0.00           O  
HETATM   26  C18 UNL     1       3.645  -1.007  -1.926  1.00  0.00           C  
HETATM   27  O9  UNL     1       4.072   0.321  -2.148  1.00  0.00           O  
HETATM   28  C19 UNL     1      -1.109   1.987  -0.056  1.00  0.00           C  
HETATM   29  C20 UNL     1      -1.370   1.682   1.426  1.00  0.00           C  
HETATM   30  C21 UNL     1      -2.789   2.119   1.713  1.00  0.00           C  
HETATM   31  H1  UNL     1      -2.742   3.876   4.733  1.00  0.00           H  
HETATM   32  H2  UNL     1      -2.040   4.376   3.113  1.00  0.00           H  
HETATM   33  H3  UNL     1      -3.075  -0.031   1.442  1.00  0.00           H  
HETATM   34  H4  UNL     1      -5.460   1.860   0.762  1.00  0.00           H  
HETATM   35  H5  UNL     1      -6.264   1.973  -1.267  1.00  0.00           H  
HETATM   36  H6  UNL     1      -5.237   1.439  -2.636  1.00  0.00           H  
HETATM   37  H7  UNL     1      -6.445   0.283  -1.852  1.00  0.00           H  
HETATM   38  H8  UNL     1      -3.117  -0.821  -0.419  1.00  0.00           H  
HETATM   39  H9  UNL     1      -4.107  -0.947  -1.860  1.00  0.00           H  
HETATM   40  H10 UNL     1      -2.838   1.580  -2.063  1.00  0.00           H  
HETATM   41  H11 UNL     1      -2.677   0.204  -3.125  1.00  0.00           H  
HETATM   42  H12 UNL     1      -0.708  -0.664  -2.154  1.00  0.00           H  
HETATM   43  H13 UNL     1       3.248  -0.350   0.076  1.00  0.00           H  
HETATM   44  H14 UNL     1       4.262  -1.634   1.099  1.00  0.00           H  
HETATM   45  H15 UNL     1       3.924  -4.640   0.602  1.00  0.00           H  
HETATM   46  H16 UNL     1       5.092  -3.810   1.717  1.00  0.00           H  
HETATM   47  H17 UNL     1       3.404  -2.824   2.784  1.00  0.00           H  
HETATM   48  H18 UNL     1       5.538  -3.570  -0.689  1.00  0.00           H  
HETATM   49  H19 UNL     1       6.391  -1.838   0.834  1.00  0.00           H  
HETATM   50  H20 UNL     1       4.583  -2.781  -2.627  1.00  0.00           H  
HETATM   51  H21 UNL     1       6.562  -1.946  -2.795  1.00  0.00           H  
HETATM   52  H22 UNL     1       2.966  -1.221  -2.798  1.00  0.00           H  
HETATM   53  H23 UNL     1       4.513   0.409  -3.034  1.00  0.00           H  
HETATM   54  H24 UNL     1      -1.951   2.474  -0.526  1.00  0.00           H  
HETATM   55  H25 UNL     1      -0.305   2.789  -0.027  1.00  0.00           H  
HETATM   56  H26 UNL     1      -0.704   2.218   2.102  1.00  0.00           H  
HETATM   57  H27 UNL     1      -1.243   0.588   1.643  1.00  0.00           H  
HETATM   58  H28 UNL     1      -3.128   2.956   1.075  1.00  0.00           H  
CONECT    1    2    2   31   32
CONECT    2    3   30
CONECT    3    4    4    5
CONECT    5    6
CONECT    6    7   30   33
CONECT    7    8    8   34
CONECT    8    9   10
CONECT    9   35   36   37
CONECT   10   11   38   39
CONECT   11   12   40   41
CONECT   12   13   13   42
CONECT   13   14   28
CONECT   14   15   15   16
CONECT   16   17
CONECT   17   18   26   43
CONECT   18   19
CONECT   19   20   22   44
CONECT   20   21   45   46
CONECT   21   47
CONECT   22   23   24   48
CONECT   23   49
CONECT   24   25   26   50
CONECT   25   51
CONECT   26   27   52
CONECT   27   53
CONECT   28   29   54   55
CONECT   29   30   56   57
CONECT   30   58
END

HMDB0035249
     RDKit          3D
Taraxinic acid glucosyl ester
 58 60  0  0  0  0  0  0  0  0999 V2000
   -2.5694    3.6451    3.6931 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9735    2.5266    3.1198 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7014    1.4307    3.7518 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7208    1.1510    4.9754 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3864    0.7290    2.7554 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6569    0.8759    1.5239 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6366    1.1729    0.4903 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6446    0.7133   -0.7275 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7192    1.1043   -1.6908 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5965   -0.1993   -1.1762 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5552    0.5291   -2.0415 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1945    0.1961   -1.6536 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5001    0.8503   -0.7422 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8876    0.4240   -0.4219 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5031    1.0705    0.4390 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4810   -0.6416   -1.0438 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8070   -1.0010   -0.6963 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8305   -2.3014   -0.1631 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0896   -2.4691    0.4066 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0954   -3.7477    1.2375 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1274   -3.6174    2.2249 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1849   -2.5150   -0.6120 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2673   -1.7810   -0.1311 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8007   -1.9338   -1.9392 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8922   -1.2587   -2.5298 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6448   -1.0071   -1.9256 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0724    0.3206   -2.1476 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1093    1.9869   -0.0558 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3697    1.6819    1.4257 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7893    2.1185    1.7130 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7423    3.8757    4.7326 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0399    4.3763    3.1133 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0749   -0.0313    1.4423 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4604    1.8602    0.7618 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2638    1.9728   -1.2675 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2366    1.4394   -2.6360 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4446    0.2827   -1.8515 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1170   -0.8209   -0.4193 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1075   -0.9467   -1.8601 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8378    1.5805   -2.0633 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6767    0.2037   -3.1254 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7082   -0.6643   -2.1540 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2475   -0.3503    0.0757 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2624   -1.6345    1.0993 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9236   -4.6404    0.6017 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0915   -3.8097    1.7170 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4040   -2.8240    2.7843 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5380   -3.5699   -0.6893 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3911   -1.8375    0.8344 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5831   -2.7806   -2.6267 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5624   -1.9463   -2.7952 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9658   -1.2215   -2.7985 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5127    0.4088   -3.0345 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9514    2.4742   -0.5256 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3055    2.7887   -0.0269 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7044    2.2178    2.1017 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2432    0.5878    1.6429 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1285    2.9560    1.0746 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 19 22  1  0
 22 23  1  0
 22 24  1  0
 24 25  1  0
 24 26  1  0
 26 27  1  0
 13 28  1  0
 28 29  1  0
 29 30  1  0
 30  2  1  0
 30  6  1  0
 26 17  1  0
  1 31  1  0
  1 32  1  0
  6 33  1  0
  7 34  1  0
  9 35  1  0
  9 36  1  0
  9 37  1  0
 10 38  1  0
 10 39  1  0
 11 40  1  0
 11 41  1  0
 12 42  1  0
 17 43  1  0
 19 44  1  0
 20 45  1  0
 20 46  1  0
 21 47  1  0
 22 48  1  0
 23 49  1  0
 24 50  1  0
 25 51  1  0
 26 52  1  0
 27 53  1  0
 28 54  1  0
 28 55  1  0
 29 56  1  0
 29 57  1  0
 30 58  1  0
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
Taraxinate glucosyl ester	Generator
(-)-Taraxinic acid beta-glucopyranosyl ester	HMDB
Taraxinic acid beta-glucopyranosyl ester	HMDB
3,4,5-Trihydroxy-6-(hydroxymethyl)oxan-2-yl 10-methyl-3-methylidene-2-oxo-2H,3H,3ah,4H,5H,8H,9H,11ah-cyclodeca[b]furan-6-carboxylic acid	Generator

Chemical Formula

C₂₁H₂₈O₉

Average Molecular Weight

424.4416

Monoisotopic Molecular Weight

424.173332494

IUPAC Name

3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl 10-methyl-3-methylidene-2-oxo-2H,3H,3aH,4H,5H,8H,9H,11aH-cyclodeca[b]furan-6-carboxylate

Traditional Name

3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl 10-methyl-3-methylidene-2-oxo-3aH,4H,5H,8H,9H,11aH-cyclodeca[b]furan-6-carboxylate

CAS Registry Number

75911-14-7

SMILES

C\C1=C\C2OC(=O)C(=C)C2CC\C(=C/CC1)C(=O)OC1OC(CO)C(O)C(O)C1O

InChI Identifier

InChI=1S/C21H28O9/c1-10-4-3-5-12(6-7-13-11(2)19(26)28-14(13)8-10)20(27)30-21-18(25)17(24)16(23)15(9-22)29-21/h5,8,13-18,21-25H,2-4,6-7,9H2,1H3/b10-8-,12-5+

InChI Key

SIOXYUXOHTZOOM-INAGUISBSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as germacranolides and derivatives. These are sesquiterpene lactones with a structure based on the germacranolide skeleton, characterized by a gamma lactone fused to a 1,7-dimethylcyclodec-1-ene moiety.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Germacranolides and derivatives

Alternative Parents

Substituents

Germacranolide
Terpene glycoside
Germacrane sesquiterpenoid
Sesquiterpenoid
Hexose monosaccharide
Dicarboxylic acid or derivatives
Gamma butyrolactone
Monosaccharide
Oxane
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Tetrahydrofuran
Secondary alcohol
Lactone
Carboxylic acid ester
Oxacycle
Polyol
Organoheterocyclic compound
Carboxylic acid derivative
Acetal
Primary alcohol
Alcohol
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen 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: HMDB0035249)

Source

Endogenous

Endogenous (HMDB: HMDB0035249)

Plant

Plant (HMDB: HMDB0035249)
Coffea (HMDB: HMDB0035249)

Animal

Animal (HMDB: HMDB0035249)

Exogenous

Food

Food (HMDB: HMDB0035249)

Herb and spice

Herb

Dandelion (FooDB: FOOD00181)

Tea

Coffee and coffee product

Coffee

Arabica coffee (FooDB: FOOD00059)
Robusta coffee (FooDB: FOOD00060)

Coffee and coffee products (FooDB: FOOD00861)

Beverage

Alcoholic beverage

Alcoholic beverages (FooDB: FOOD00854)

Beverages (FooDB: FOOD00870)

Exogenous (HMDB: HMDB0035249)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0035249)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0035249)

Lipid metabolism pathway (HMDB: HMDB0035249)

Cellular process

Cell signaling (HMDB: HMDB0035249)

Biochemical process

Lipid transport (HMDB: HMDB0035249)

Role

Biological role

Energy source (HMDB: HMDB0035249)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0035249)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	84 - 86 °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	1.84 g/L	ALOGPS
logP	-0.02	ALOGPS
logP	0.97	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Acidic)	12.2	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	142.75 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	104.09 m³·mol⁻¹	ChemAxon
Polarizability	43.24 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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]+	197.362	31661259
DarkChem	[M-H]-	193.337	31661259
DeepCCS	[M+H]+	200.157	30932474
DeepCCS	[M-H]-	197.799	30932474
DeepCCS	[M-2H]-	231.232	30932474
DeepCCS	[M+Na]+	206.446	30932474
AllCCS	[M+H]+	202.2	32859911
AllCCS	[M+H-H2O]+	199.8	32859911
AllCCS	[M+NH4]+	204.3	32859911
AllCCS	[M+Na]+	204.9	32859911
AllCCS	[M-H]-	195.4	32859911
AllCCS	[M+Na-2H]-	196.1	32859911
AllCCS	[M+HCOO]-	197.0	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Taraxinic acid glucosyl ester	C\C1=C\C2OC(=O)C(=C)C2CC\C(=C/CC1)C(=O)OC1OC(CO)C(O)C(O)C1O	3864.1	Standard polar	33892256
Taraxinic acid glucosyl ester	C\C1=C\C2OC(=O)C(=C)C2CC\C(=C/CC1)C(=O)OC1OC(CO)C(O)C(O)C1O	3186.4	Standard non polar	33892256
Taraxinic acid glucosyl ester	C\C1=C\C2OC(=O)C(=C)C2CC\C(=C/CC1)C(=O)OC1OC(CO)C(O)C(O)C1O	3463.2	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Taraxinic acid glucosyl ester,1TMS,isomer #1	C=C1C(=O)OC2/C=C(/C)CC/C=C(/C(=O)OC3OC(CO[Si](C)(C)C)C(O)C(O)C3O)CCC12	3483.9	Semi standard non polar	33892256
Taraxinic acid glucosyl ester,1TMS,isomer #2	C=C1C(=O)OC2/C=C(/C)CC/C=C(/C(=O)OC3OC(CO)C(O[Si](C)(C)C)C(O)C3O)CCC12	3489.2	Semi standard non polar	33892256
Taraxinic acid glucosyl ester,1TMS,isomer #3	C=C1C(=O)OC2/C=C(/C)CC/C=C(/C(=O)OC3OC(CO)C(O)C(O[Si](C)(C)C)C3O)CCC12	3507.4	Semi standard non polar	33892256
Taraxinic acid glucosyl ester,1TMS,isomer #4	C=C1C(=O)OC2/C=C(/C)CC/C=C(/C(=O)OC3OC(CO)C(O)C(O)C3O[Si](C)(C)C)CCC12	3492.0	Semi standard non polar	33892256
Taraxinic acid glucosyl ester,2TMS,isomer #1	C=C1C(=O)OC2/C=C(/C)CC/C=C(/C(=O)OC3OC(CO[Si](C)(C)C)C(O[Si](C)(C)C)C(O)C3O)CCC12	3456.9	Semi standard non polar	33892256
Taraxinic acid glucosyl ester,2TMS,isomer #2	C=C1C(=O)OC2/C=C(/C)CC/C=C(/C(=O)OC3OC(CO[Si](C)(C)C)C(O)C(O[Si](C)(C)C)C3O)CCC12	3472.2	Semi standard non polar	33892256
Taraxinic acid glucosyl ester,2TMS,isomer #3	C=C1C(=O)OC2/C=C(/C)CC/C=C(/C(=O)OC3OC(CO[Si](C)(C)C)C(O)C(O)C3O[Si](C)(C)C)CCC12	3453.5	Semi standard non polar	33892256
Taraxinic acid glucosyl ester,2TMS,isomer #4	C=C1C(=O)OC2/C=C(/C)CC/C=C(/C(=O)OC3OC(CO)C(O[Si](C)(C)C)C(O[Si](C)(C)C)C3O)CCC12	3456.8	Semi standard non polar	33892256
Taraxinic acid glucosyl ester,2TMS,isomer #5	C=C1C(=O)OC2/C=C(/C)CC/C=C(/C(=O)OC3OC(CO)C(O[Si](C)(C)C)C(O)C3O[Si](C)(C)C)CCC12	3457.9	Semi standard non polar	33892256
Taraxinic acid glucosyl ester,2TMS,isomer #6	C=C1C(=O)OC2/C=C(/C)CC/C=C(/C(=O)OC3OC(CO)C(O)C(O[Si](C)(C)C)C3O[Si](C)(C)C)CCC12	3472.5	Semi standard non polar	33892256
Taraxinic acid glucosyl ester,3TMS,isomer #1	C=C1C(=O)OC2/C=C(/C)CC/C=C(/C(=O)OC3OC(CO[Si](C)(C)C)C(O[Si](C)(C)C)C(O[Si](C)(C)C)C3O)CCC12	3467.7	Semi standard non polar	33892256
Taraxinic acid glucosyl ester,3TMS,isomer #2	C=C1C(=O)OC2/C=C(/C)CC/C=C(/C(=O)OC3OC(CO[Si](C)(C)C)C(O[Si](C)(C)C)C(O)C3O[Si](C)(C)C)CCC12	3465.8	Semi standard non polar	33892256
Taraxinic acid glucosyl ester,3TMS,isomer #3	C=C1C(=O)OC2/C=C(/C)CC/C=C(/C(=O)OC3OC(CO[Si](C)(C)C)C(O)C(O[Si](C)(C)C)C3O[Si](C)(C)C)CCC12	3464.4	Semi standard non polar	33892256
Taraxinic acid glucosyl ester,3TMS,isomer #4	C=C1C(=O)OC2/C=C(/C)CC/C=C(/C(=O)OC3OC(CO)C(O[Si](C)(C)C)C(O[Si](C)(C)C)C3O[Si](C)(C)C)CCC12	3470.7	Semi standard non polar	33892256
Taraxinic acid glucosyl ester,4TMS,isomer #1	C=C1C(=O)OC2/C=C(/C)CC/C=C(/C(=O)OC3OC(CO[Si](C)(C)C)C(O[Si](C)(C)C)C(O[Si](C)(C)C)C3O[Si](C)(C)C)CCC12	3475.6	Semi standard non polar	33892256
Taraxinic acid glucosyl ester,1TBDMS,isomer #1	C=C1C(=O)OC2/C=C(/C)CC/C=C(/C(=O)OC3OC(CO[Si](C)(C)C(C)(C)C)C(O)C(O)C3O)CCC12	3675.0	Semi standard non polar	33892256
Taraxinic acid glucosyl ester,1TBDMS,isomer #2	C=C1C(=O)OC2/C=C(/C)CC/C=C(/C(=O)OC3OC(CO)C(O[Si](C)(C)C(C)(C)C)C(O)C3O)CCC12	3703.6	Semi standard non polar	33892256
Taraxinic acid glucosyl ester,1TBDMS,isomer #3	C=C1C(=O)OC2/C=C(/C)CC/C=C(/C(=O)OC3OC(CO)C(O)C(O[Si](C)(C)C(C)(C)C)C3O)CCC12	3715.1	Semi standard non polar	33892256
Taraxinic acid glucosyl ester,1TBDMS,isomer #4	C=C1C(=O)OC2/C=C(/C)CC/C=C(/C(=O)OC3OC(CO)C(O)C(O)C3O[Si](C)(C)C(C)(C)C)CCC12	3707.0	Semi standard non polar	33892256
Taraxinic acid glucosyl ester,2TBDMS,isomer #1	C=C1C(=O)OC2/C=C(/C)CC/C=C(/C(=O)OC3OC(CO[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C(O)C3O)CCC12	3870.8	Semi standard non polar	33892256
Taraxinic acid glucosyl ester,2TBDMS,isomer #2	C=C1C(=O)OC2/C=C(/C)CC/C=C(/C(=O)OC3OC(CO[Si](C)(C)C(C)(C)C)C(O)C(O[Si](C)(C)C(C)(C)C)C3O)CCC12	3879.8	Semi standard non polar	33892256
Taraxinic acid glucosyl ester,2TBDMS,isomer #3	C=C1C(=O)OC2/C=C(/C)CC/C=C(/C(=O)OC3OC(CO[Si](C)(C)C(C)(C)C)C(O)C(O)C3O[Si](C)(C)C(C)(C)C)CCC12	3874.5	Semi standard non polar	33892256
Taraxinic acid glucosyl ester,2TBDMS,isomer #4	C=C1C(=O)OC2/C=C(/C)CC/C=C(/C(=O)OC3OC(CO)C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C3O)CCC12	3880.3	Semi standard non polar	33892256
Taraxinic acid glucosyl ester,2TBDMS,isomer #5	C=C1C(=O)OC2/C=C(/C)CC/C=C(/C(=O)OC3OC(CO)C(O[Si](C)(C)C(C)(C)C)C(O)C3O[Si](C)(C)C(C)(C)C)CCC12	3890.7	Semi standard non polar	33892256
Taraxinic acid glucosyl ester,2TBDMS,isomer #6	C=C1C(=O)OC2/C=C(/C)CC/C=C(/C(=O)OC3OC(CO)C(O)C(O[Si](C)(C)C(C)(C)C)C3O[Si](C)(C)C(C)(C)C)CCC12	3891.4	Semi standard non polar	33892256
Taraxinic acid glucosyl ester,3TBDMS,isomer #1	C=C1C(=O)OC2/C=C(/C)CC/C=C(/C(=O)OC3OC(CO[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C3O)CCC12	4072.8	Semi standard non polar	33892256
Taraxinic acid glucosyl ester,3TBDMS,isomer #2	C=C1C(=O)OC2/C=C(/C)CC/C=C(/C(=O)OC3OC(CO[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C(O)C3O[Si](C)(C)C(C)(C)C)CCC12	4077.9	Semi standard non polar	33892256
Taraxinic acid glucosyl ester,3TBDMS,isomer #3	C=C1C(=O)OC2/C=C(/C)CC/C=C(/C(=O)OC3OC(CO[Si](C)(C)C(C)(C)C)C(O)C(O[Si](C)(C)C(C)(C)C)C3O[Si](C)(C)C(C)(C)C)CCC12	4067.6	Semi standard non polar	33892256
Taraxinic acid glucosyl ester,3TBDMS,isomer #4	C=C1C(=O)OC2/C=C(/C)CC/C=C(/C(=O)OC3OC(CO)C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C3O[Si](C)(C)C(C)(C)C)CCC12	4073.1	Semi standard non polar	33892256
Taraxinic acid glucosyl ester,4TBDMS,isomer #1	C=C1C(=O)OC2/C=C(/C)CC/C=C(/C(=O)OC3OC(CO[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C3O[Si](C)(C)C(C)(C)C)CCC12	4236.9	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 - Taraxinic acid glucosyl ester GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4i-9314200000-f036712834a8ce29cc0b	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Taraxinic acid glucosyl ester GC-MS (3 TMS) - 70eV, Positive	splash10-004i-3394038000-ac22015b2e50b547b4cc	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Taraxinic acid glucosyl ester GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Taraxinic acid glucosyl ester 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 - Taraxinic acid glucosyl ester 10V, Positive-QTOF	splash10-03dj-0490300000-afa79b42ed7e008d26b7	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Taraxinic acid glucosyl ester 20V, Positive-QTOF	splash10-01ot-0790000000-9ddd12e7cf4e5e3f8737	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Taraxinic acid glucosyl ester 40V, Positive-QTOF	splash10-0005-3950000000-a98741cd15ab763157b7	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Taraxinic acid glucosyl ester 10V, Negative-QTOF	splash10-03k9-1291400000-bdf07daabf1f44a5c1e9	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Taraxinic acid glucosyl ester 20V, Negative-QTOF	splash10-03xr-2390100000-428eb5620eceb76a57e2	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Taraxinic acid glucosyl ester 40V, Negative-QTOF	splash10-0903-7390000000-f4d6cac15200159ff2b8	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Taraxinic acid glucosyl ester 10V, Positive-QTOF	splash10-004j-0151900000-858a5a4e7e9b4083f7ef	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Taraxinic acid glucosyl ester 20V, Positive-QTOF	splash10-0f6t-2291100000-b7aea0c2729f6b680d43	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Taraxinic acid glucosyl ester 40V, Positive-QTOF	splash10-016s-6491000000-85578ec0da06d4e88912	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Taraxinic acid glucosyl ester 10V, Negative-QTOF	splash10-00di-0422900000-23318915ba361ee2f6d8	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Taraxinic acid glucosyl ester 20V, Negative-QTOF	splash10-0w90-6339200000-f60b6b9b3d77a48d7e82	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Taraxinic acid glucosyl ester 40V, Negative-QTOF	splash10-066u-6490100000-a9d6135474914c39dc79	2021-09-25	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

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

FDB013909

KNApSAcK ID

C00037887

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

131751687

PDB ID

Not Available

ChEBI ID

172666

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 Taraxinic acid glucosyl ester (HMDB0035249)

MOL for HMDB0035249 (Taraxinic acid glucosyl ester)

3D MOL for HMDB0035249 (Taraxinic acid glucosyl ester)

3D SDF for HMDB0035249 (Taraxinic acid glucosyl ester)

3D-SDF for HMDB0035249 (Taraxinic acid glucosyl ester)

PDB for HMDB0035249 (Taraxinic acid glucosyl ester)

3D PDB for HMDB0035249 (Taraxinic acid glucosyl ester)

SMILES for HMDB0035249 (Taraxinic acid glucosyl ester)

INCHI for HMDB0035249 (Taraxinic acid glucosyl ester)

Structure for HMDB0035249 (Taraxinic acid glucosyl ester)

3D Structure for HMDB0035249 (Taraxinic acid glucosyl ester)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra