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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 19:50:55 UTC

Update Date

2022-03-07 02:54:16 UTC

HMDB ID

HMDB0034920

Secondary Accession Numbers

HMDB34920

Metabolite Identification

Common Name

Taraxerol

Description

Taraxerol, also known as alnulin, is a naturally-occurring pentacyclic oleanane-type triterpenoid. It can be found in plants such as Taraxacum officinale (Asteraceae; dandelion), Alnus glutinosa (Betulaceae), Litsea dealbata (Lauraceae), Skimmia spp. (Rutaceae), Dorstenia spp. (Moraceae), Maytenus spp. (Celastraceae), and Alchornea latifolia (Euphobiaceae). Taraxerol is an oleanan-3-ol with an alpha-methyl substituent at position 13, a missing methyl group at position 14, and a double bond between 14 and 15. A large number of medicinal plants are known to have this compound in their leaves, roots or seed oil (PMID: 26009688 ). Taraxerol has shown the anti-inflammatory effects in vitro, it can disrupt the activation of the enzymes MAP3K7 (TAK1), protein kinase B (PKB or Akt), and NF-κB. By doing so, it may inhibit the expression of proinflammatory mediators in microphages (PMID: 23333629). Taraxerol also exhibits anti-carcinogenic activity. In vivo two-stage carcinogenesis tests of mouse skin tumor showed that taraxerol can inhibit the induction of Epstein-Barr virus early antigen (EBV-EA) by the tumor initiator 7,12-dimethylbenz(a)anthracene (DMBA) and the tumor promoter 12-O-tetradecanoylphorbol-13-acetate (TPA) (PMID: 10408235 ) (Wikipedia ). Taraxerol is found in alcoholic beverages.

Structure

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


  Mrv0541 02241215532D          

 31 35  0  0  0  0            999 V2000
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   -0.3575   -2.0630    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.0710    1.2367    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0710    0.4118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
M  END

HMDB0034920
     RDKit          3D
Taraxerol
 81 85  0  0  0  0  0  0  0  0999 V2000
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 31 81  1  0
M  END


  Mrv0541 02241215532D          

 31 35  0  0  0  0            999 V2000
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  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 16  1  0  0  0  0
  9 10  1  0  0  0  0
  9 22  1  0  0  0  0
 11 12  1  0  0  0  0
 11 20  1  0  0  0  0
 12 30  1  0  0  0  0
 13 14  1  0  0  0  0
 13 20  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 18 19  1  0  0  0  0
 18 30  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 24 27  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0034920

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1(C)CCC2(C)CC=C3C4(C)CCC5C(C)(C)C(O)CCC5(C)C4CCC3(C)C2C1

> <INCHI_IDENTIFIER>
InChI=1S/C30H50O/c1-25(2)17-18-27(5)13-9-21-29(7)14-10-20-26(3,4)24(31)12-16-28(20,6)22(29)11-15-30(21,8)23(27)19-25/h9,20,22-24,31H,10-19H2,1-8H3

> <INCHI_KEY>
GGGUGZHBAOMSFJ-UHFFFAOYSA-N

> <FORMULA>
C30H50O

> <MOLECULAR_WEIGHT>
426.7174

> <EXACT_MASS>
426.386166222

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
54.38613536581463

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
4,4,6a,8a,11,11,12b,14b-octamethyl-1,2,3,4,4a,5,6,6a,8,8a,9,10,11,12,12a,12b,13,14,14a,14b-icosahydropicen-3-ol

> <ALOGPS_LOGP>
7.20

> <JCHEM_LOGP>
7.403140834333334

> <ALOGPS_LOGS>
-6.79

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
19.48943324166892

> <JCHEM_PKA_STRONGEST_BASIC>
-0.8351219000940143

> <JCHEM_POLAR_SURFACE_AREA>
20.23

> <JCHEM_REFRACTIVITY>
131.9073

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
6.90e-05 g/l

> <JCHEM_TRADITIONAL_IUPAC>
taraxerol

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0034920
     RDKit          3D
Taraxerol
 81 85  0  0  0  0  0  0  0  0999 V2000
   -6.1825   -0.4164    1.4559 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7766    0.1812    1.2412 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4170    0.7245    2.6410 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9699    1.3614    0.3834 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8469    1.7285   -0.5302 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4587    0.4807   -1.2650 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7937    0.0416   -1.9193 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5863    0.8533   -2.3868 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1458    0.5601   -2.1616 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6487   -0.1816   -1.1971 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5153   -0.8299   -0.1926 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3267   -2.3342   -0.0636 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0265   -0.2358    1.1159 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3018    0.3227    1.2108 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1578    0.6727    0.0331 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8364   -0.2808   -1.1026 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3877    0.1003   -2.4510 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4476   -1.5677   -0.7630 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9402   -1.4367   -0.6904 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5284   -0.1442   -0.2727 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8457   -0.3882    0.3902 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9778    0.4791   -0.2041 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3623   -1.8215    0.1667 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9488   -0.1983    1.8538 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4206    1.0474    2.2614 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5531   -0.3279    2.4459 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8605    0.9074    1.8951 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5933    0.8125    0.4076 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9857    2.2353   -0.0843 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9977   -0.6402   -0.4214 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8076   -0.8638    0.8146 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0900   -1.5392    1.5234 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6918    0.0136    2.3153 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7473   -0.2113    0.5288 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3672    1.1414    3.0485 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6237    1.4976    2.5838 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1367   -0.1607    3.2427 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2069    2.2789    0.9867 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8857    1.2451   -0.2692 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2598    2.4364   -1.2883 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0155    2.2560   -0.0496 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3687    0.9267   -2.2108 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5074   -0.4900   -2.8642 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3008   -0.6915   -1.2920 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8670    0.3598   -3.3647 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6524    1.9493   -2.6117 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5285    1.0708   -2.9259 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9758   -2.6326    0.9685 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3399   -2.8705   -0.0608 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8363   -2.8214   -0.8867 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1684   -1.0128    1.9000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8410    0.5046    1.3690 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9403   -0.3900    1.8170 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1909    1.2941    1.7943 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6972    1.6393   -0.3605 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3316   -0.4693   -2.7240 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7284   -0.3266   -3.2812 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4689    1.1582   -2.6544 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1014   -1.9299    0.1919 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2763   -2.2696   -1.6349 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4103   -1.7718   -1.6490 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2906   -2.2506    0.0198 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8501    0.3818   -1.2301 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8539    0.4062    0.4421 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2704   -0.0241   -1.1731 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6374    1.4731   -0.4740 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1997   -2.2076   -0.8226 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0343   -2.4927    1.0136 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4871   -1.8112    0.3105 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5666   -0.9438    2.3944 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6866    1.6495    1.5532 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0829   -1.2723    2.2154 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6128   -0.1579    3.5528 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5913    1.7448    2.1475 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0363    1.1265    2.5451 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7789    2.6683    0.5209 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3023    2.2156   -1.1244 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0881    2.9068    0.0464 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2320   -1.5544   -1.0760 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1196   -1.0495    1.6622 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4002   -1.8343    0.7839 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
  6  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 21 23  1  0
 21 24  1  0
 24 25  1  0
 24 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
 11 30  1  0
 30 31  1  0
 31  2  1  0
 30  6  1  0
 16 10  1  0
 28 20  1  0
 28 15  1  0
  1 32  1  0
  1 33  1  0
  1 34  1  0
  3 35  1  0
  3 36  1  0
  3 37  1  0
  4 38  1  0
  4 39  1  0
  5 40  1  0
  5 41  1  0
  7 42  1  0
  7 43  1  0
  7 44  1  0
  8 45  1  0
  8 46  1  0
  9 47  1  0
 12 48  1  0
 12 49  1  0
 12 50  1  0
 13 51  1  0
 13 52  1  0
 14 53  1  0
 14 54  1  0
 15 55  1  0
 17 56  1  0
 17 57  1  0
 17 58  1  0
 18 59  1  0
 18 60  1  0
 19 61  1  0
 19 62  1  0
 20 63  1  0
 22 64  1  0
 22 65  1  0
 22 66  1  0
 23 67  1  0
 23 68  1  0
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 24 70  1  0
 25 71  1  0
 26 72  1  0
 26 73  1  0
 27 74  1  0
 27 75  1  0
 29 76  1  0
 29 77  1  0
 29 78  1  0
 30 79  1  0
 31 80  1  0
 31 81  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      -2.002  -3.081   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.667  -3.851   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.667  -3.081   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.999   2.309   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.999   0.769   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.667   1.539   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.667   0.769   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.667  -0.771   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.002  -1.541   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -2.002  -0.001   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.334   1.539   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.334   3.079   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.666  -0.771   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.334  -1.541   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.999  -0.771   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.667  -1.541   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.999  -2.311   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.000   3.079   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.000   1.539   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.666   0.769   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       6.000  -0.001   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -3.334  -0.771   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -4.669  -1.541   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -4.669  -3.081   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      -6.000  -3.851   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      -4.325  -5.029   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -3.334  -3.851   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -2.346  -5.029   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       3.678   5.029   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       4.666   3.848   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       5.657   5.029   0.000  0.00  0.00           C+0
CONECT    1    2    9   27                                                  
CONECT    2    1    3                                                       
CONECT    3    2   16                                                       
CONECT    4    5                                                            
CONECT    5    4    6   11   15                                             
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   16                                                  
CONECT    9    1    8   10   22                                             
CONECT   10    9                                                            
CONECT   11    5   12   20                                                  
CONECT   12   11   30                                                       
CONECT   13   14   20                                                       
CONECT   14   13   15                                                       
CONECT   15    5   14   16                                                  
CONECT   16    3    8   15   17                                             
CONECT   17   16                                                            
CONECT   18   19   30                                                       
CONECT   19   18   20                                                       
CONECT   20   11   13   19   21                                             
CONECT   21   20                                                            
CONECT   22    9   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25   27                                                  
CONECT   25   24                                                            
CONECT   26   27                                                            
CONECT   27    1   24   26   28                                             
CONECT   28   27                                                            
CONECT   29   30                                                            
CONECT   30   12   18   29   31                                             
CONECT   31   30                                                            
MASTER        0    0    0    0    0    0    0    0   31    0   70    0
END

COMPND    HMDB0034920
HETATM    1  C1  UNL     1      -6.182  -0.416   1.456  1.00  0.00           C  
HETATM    2  C2  UNL     1      -4.777   0.181   1.241  1.00  0.00           C  
HETATM    3  C3  UNL     1      -4.417   0.725   2.641  1.00  0.00           C  
HETATM    4  C4  UNL     1      -4.970   1.361   0.383  1.00  0.00           C  
HETATM    5  C5  UNL     1      -3.847   1.728  -0.530  1.00  0.00           C  
HETATM    6  C6  UNL     1      -3.459   0.481  -1.265  1.00  0.00           C  
HETATM    7  C7  UNL     1      -4.794   0.042  -1.919  1.00  0.00           C  
HETATM    8  C8  UNL     1      -2.586   0.853  -2.387  1.00  0.00           C  
HETATM    9  C9  UNL     1      -1.146   0.560  -2.162  1.00  0.00           C  
HETATM   10  C10 UNL     1      -0.649  -0.182  -1.197  1.00  0.00           C  
HETATM   11  C11 UNL     1      -1.515  -0.830  -0.193  1.00  0.00           C  
HETATM   12  C12 UNL     1      -1.327  -2.334  -0.064  1.00  0.00           C  
HETATM   13  C13 UNL     1      -1.027  -0.236   1.116  1.00  0.00           C  
HETATM   14  C14 UNL     1       0.302   0.323   1.211  1.00  0.00           C  
HETATM   15  C15 UNL     1       1.158   0.673   0.033  1.00  0.00           C  
HETATM   16  C16 UNL     1       0.836  -0.281  -1.103  1.00  0.00           C  
HETATM   17  C17 UNL     1       1.388   0.100  -2.451  1.00  0.00           C  
HETATM   18  C18 UNL     1       1.448  -1.568  -0.763  1.00  0.00           C  
HETATM   19  C19 UNL     1       2.940  -1.437  -0.690  1.00  0.00           C  
HETATM   20  C20 UNL     1       3.528  -0.144  -0.273  1.00  0.00           C  
HETATM   21  C21 UNL     1       4.846  -0.388   0.390  1.00  0.00           C  
HETATM   22  C22 UNL     1       5.978   0.479  -0.204  1.00  0.00           C  
HETATM   23  C23 UNL     1       5.362  -1.822   0.167  1.00  0.00           C  
HETATM   24  C24 UNL     1       4.949  -0.198   1.854  1.00  0.00           C  
HETATM   25  O1  UNL     1       5.421   1.047   2.261  1.00  0.00           O  
HETATM   26  C25 UNL     1       3.553  -0.328   2.446  1.00  0.00           C  
HETATM   27  C26 UNL     1       2.861   0.907   1.895  1.00  0.00           C  
HETATM   28  C27 UNL     1       2.593   0.812   0.408  1.00  0.00           C  
HETATM   29  C28 UNL     1       2.986   2.235  -0.084  1.00  0.00           C  
HETATM   30  C29 UNL     1      -2.998  -0.640  -0.421  1.00  0.00           C  
HETATM   31  C30 UNL     1      -3.808  -0.864   0.815  1.00  0.00           C  
HETATM   32  H1  UNL     1      -6.090  -1.539   1.523  1.00  0.00           H  
HETATM   33  H2  UNL     1      -6.692   0.014   2.315  1.00  0.00           H  
HETATM   34  H3  UNL     1      -6.747  -0.211   0.529  1.00  0.00           H  
HETATM   35  H4  UNL     1      -5.367   1.141   3.048  1.00  0.00           H  
HETATM   36  H5  UNL     1      -3.624   1.498   2.584  1.00  0.00           H  
HETATM   37  H6  UNL     1      -4.137  -0.161   3.243  1.00  0.00           H  
HETATM   38  H7  UNL     1      -5.207   2.279   0.987  1.00  0.00           H  
HETATM   39  H8  UNL     1      -5.886   1.245  -0.269  1.00  0.00           H  
HETATM   40  H9  UNL     1      -4.260   2.436  -1.288  1.00  0.00           H  
HETATM   41  H10 UNL     1      -3.016   2.256  -0.050  1.00  0.00           H  
HETATM   42  H11 UNL     1      -5.369   0.927  -2.211  1.00  0.00           H  
HETATM   43  H12 UNL     1      -4.507  -0.490  -2.864  1.00  0.00           H  
HETATM   44  H13 UNL     1      -5.301  -0.691  -1.292  1.00  0.00           H  
HETATM   45  H14 UNL     1      -2.867   0.360  -3.365  1.00  0.00           H  
HETATM   46  H15 UNL     1      -2.652   1.949  -2.612  1.00  0.00           H  
HETATM   47  H16 UNL     1      -0.529   1.071  -2.926  1.00  0.00           H  
HETATM   48  H17 UNL     1      -0.976  -2.633   0.969  1.00  0.00           H  
HETATM   49  H18 UNL     1      -2.340  -2.871  -0.061  1.00  0.00           H  
HETATM   50  H19 UNL     1      -0.836  -2.821  -0.887  1.00  0.00           H  
HETATM   51  H20 UNL     1      -1.168  -1.013   1.900  1.00  0.00           H  
HETATM   52  H21 UNL     1      -1.841   0.505   1.369  1.00  0.00           H  
HETATM   53  H22 UNL     1       0.940  -0.390   1.817  1.00  0.00           H  
HETATM   54  H23 UNL     1       0.191   1.294   1.794  1.00  0.00           H  
HETATM   55  H24 UNL     1       0.697   1.639  -0.361  1.00  0.00           H  
HETATM   56  H25 UNL     1       2.332  -0.469  -2.724  1.00  0.00           H  
HETATM   57  H26 UNL     1       0.728  -0.327  -3.281  1.00  0.00           H  
HETATM   58  H27 UNL     1       1.469   1.158  -2.654  1.00  0.00           H  
HETATM   59  H28 UNL     1       1.101  -1.930   0.192  1.00  0.00           H  
HETATM   60  H29 UNL     1       1.276  -2.270  -1.635  1.00  0.00           H  
HETATM   61  H30 UNL     1       3.410  -1.772  -1.649  1.00  0.00           H  
HETATM   62  H31 UNL     1       3.291  -2.251   0.020  1.00  0.00           H  
HETATM   63  H32 UNL     1       3.850   0.382  -1.230  1.00  0.00           H  
HETATM   64  H33 UNL     1       6.854   0.406   0.442  1.00  0.00           H  
HETATM   65  H34 UNL     1       6.270  -0.024  -1.173  1.00  0.00           H  
HETATM   66  H35 UNL     1       5.637   1.473  -0.474  1.00  0.00           H  
HETATM   67  H36 UNL     1       5.200  -2.208  -0.823  1.00  0.00           H  
HETATM   68  H37 UNL     1       5.034  -2.493   1.014  1.00  0.00           H  
HETATM   69  H38 UNL     1       6.487  -1.811   0.310  1.00  0.00           H  
HETATM   70  H39 UNL     1       5.567  -0.944   2.394  1.00  0.00           H  
HETATM   71  H40 UNL     1       5.687   1.649   1.553  1.00  0.00           H  
HETATM   72  H41 UNL     1       3.083  -1.272   2.215  1.00  0.00           H  
HETATM   73  H42 UNL     1       3.613  -0.158   3.553  1.00  0.00           H  
HETATM   74  H43 UNL     1       3.591   1.745   2.148  1.00  0.00           H  
HETATM   75  H44 UNL     1       2.036   1.127   2.545  1.00  0.00           H  
HETATM   76  H45 UNL     1       3.779   2.668   0.521  1.00  0.00           H  
HETATM   77  H46 UNL     1       3.302   2.216  -1.124  1.00  0.00           H  
HETATM   78  H47 UNL     1       2.088   2.907   0.046  1.00  0.00           H  
HETATM   79  H48 UNL     1      -3.232  -1.554  -1.076  1.00  0.00           H  
HETATM   80  H49 UNL     1      -3.120  -1.049   1.662  1.00  0.00           H  
HETATM   81  H50 UNL     1      -4.400  -1.834   0.784  1.00  0.00           H  
CONECT    1    2   32   33   34
CONECT    2    3    4   31
CONECT    3   35   36   37
CONECT    4    5   38   39
CONECT    5    6   40   41
CONECT    6    7    8   30
CONECT    7   42   43   44
CONECT    8    9   45   46
CONECT    9   10   10   47
CONECT   10   11   16
CONECT   11   12   13   30
CONECT   12   48   49   50
CONECT   13   14   51   52
CONECT   14   15   53   54
CONECT   15   16   28   55
CONECT   16   17   18
CONECT   17   56   57   58
CONECT   18   19   59   60
CONECT   19   20   61   62
CONECT   20   21   28   63
CONECT   21   22   23   24
CONECT   22   64   65   66
CONECT   23   67   68   69
CONECT   24   25   26   70
CONECT   25   71
CONECT   26   27   72   73
CONECT   27   28   74   75
CONECT   28   29
CONECT   29   76   77   78
CONECT   30   31   79
CONECT   31   80   81
END

HMDB0034920
     RDKit          3D
Taraxerol
 81 85  0  0  0  0  0  0  0  0999 V2000
   -6.1825   -0.4164    1.4559 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7766    0.1812    1.2412 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4170    0.7245    2.6410 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9699    1.3614    0.3834 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8469    1.7285   -0.5302 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4587    0.4807   -1.2650 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7937    0.0416   -1.9193 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5863    0.8533   -2.3868 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1458    0.5601   -2.1616 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6487   -0.1816   -1.1971 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5153   -0.8299   -0.1926 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3267   -2.3342   -0.0636 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0265   -0.2358    1.1159 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3018    0.3227    1.2108 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1578    0.6727    0.0331 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8364   -0.2808   -1.1026 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3877    0.1003   -2.4510 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4476   -1.5677   -0.7630 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9402   -1.4367   -0.6904 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5284   -0.1442   -0.2727 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8457   -0.3882    0.3902 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9778    0.4791   -0.2041 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3623   -1.8215    0.1667 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9488   -0.1983    1.8538 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4206    1.0474    2.2614 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5531   -0.3279    2.4459 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8605    0.9074    1.8951 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5933    0.8125    0.4076 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9857    2.2353   -0.0843 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9977   -0.6402   -0.4214 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8076   -0.8638    0.8146 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0900   -1.5392    1.5234 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6918    0.0136    2.3153 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7473   -0.2113    0.5288 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3672    1.1414    3.0485 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6237    1.4976    2.5838 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1367   -0.1607    3.2427 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2069    2.2789    0.9867 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8857    1.2451   -0.2692 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2598    2.4364   -1.2883 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0155    2.2560   -0.0496 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3687    0.9267   -2.2108 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5074   -0.4900   -2.8642 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3008   -0.6915   -1.2920 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8670    0.3598   -3.3647 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6524    1.9493   -2.6117 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5285    1.0708   -2.9259 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9758   -2.6326    0.9685 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3399   -2.8705   -0.0608 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8363   -2.8214   -0.8867 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1684   -1.0128    1.9000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8410    0.5046    1.3690 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9403   -0.3900    1.8170 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1909    1.2941    1.7943 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6972    1.6393   -0.3605 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3316   -0.4693   -2.7240 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7284   -0.3266   -3.2812 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4689    1.1582   -2.6544 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1014   -1.9299    0.1919 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2763   -2.2696   -1.6349 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4103   -1.7718   -1.6490 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2906   -2.2506    0.0198 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8501    0.3818   -1.2301 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8539    0.4062    0.4421 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2704   -0.0241   -1.1731 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6374    1.4731   -0.4740 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1997   -2.2076   -0.8226 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0343   -2.4927    1.0136 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4871   -1.8112    0.3105 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5666   -0.9438    2.3944 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6866    1.6495    1.5532 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0829   -1.2723    2.2154 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6128   -0.1579    3.5528 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5913    1.7448    2.1475 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0363    1.1265    2.5451 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7789    2.6683    0.5209 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3023    2.2156   -1.1244 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0881    2.9068    0.0464 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2320   -1.5544   -1.0760 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1196   -1.0495    1.6622 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4002   -1.8343    0.7839 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
  6  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 21 23  1  0
 21 24  1  0
 24 25  1  0
 24 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
 11 30  1  0
 30 31  1  0
 31  2  1  0
 30  6  1  0
 16 10  1  0
 28 20  1  0
 28 15  1  0
  1 32  1  0
  1 33  1  0
  1 34  1  0
  3 35  1  0
  3 36  1  0
  3 37  1  0
  4 38  1  0
  4 39  1  0
  5 40  1  0
  5 41  1  0
  7 42  1  0
  7 43  1  0
  7 44  1  0
  8 45  1  0
  8 46  1  0
  9 47  1  0
 12 48  1  0
 12 49  1  0
 12 50  1  0
 13 51  1  0
 13 52  1  0
 14 53  1  0
 14 54  1  0
 15 55  1  0
 17 56  1  0
 17 57  1  0
 17 58  1  0
 18 59  1  0
 18 60  1  0
 19 61  1  0
 19 62  1  0
 20 63  1  0
 22 64  1  0
 22 65  1  0
 22 66  1  0
 23 67  1  0
 23 68  1  0
 23 69  1  0
 24 70  1  0
 25 71  1  0
 26 72  1  0
 26 73  1  0
 27 74  1  0
 27 75  1  0
 29 76  1  0
 29 77  1  0
 29 78  1  0
 30 79  1  0
 31 80  1  0
 31 81  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(3beta)-D-Friedoolean-14-en-3-ol	HMDB
Alnulin	HMDB
D-Friedoolean-14-en-3beta-ol	HMDB
Skimmiol?	HMDB
3beta-Taraxerol	MeSH
D-Friedoolean-14-en-3 beta-ol	MeSH

Chemical Formula

C₃₀H₅₀O

Average Molecular Weight

426.7174

Monoisotopic Molecular Weight

426.386166222

IUPAC Name

4,4,6a,8a,11,11,12b,14b-octamethyl-1,2,3,4,4a,5,6,6a,8,8a,9,10,11,12,12a,12b,13,14,14a,14b-icosahydropicen-3-ol

Traditional Name

taraxerol

CAS Registry Number

127-22-0

SMILES

CC1(C)CCC2(C)CC=C3C4(C)CCC5C(C)(C)C(O)CCC5(C)C4CCC3(C)C2C1

InChI Identifier

InChI=1S/C30H50O/c1-25(2)17-18-27(5)13-9-21-29(7)14-10-20-26(3,4)24(31)12-16-28(20,6)22(29)11-15-30(21,8)23(27)19-25/h9,20,22-24,31H,10-19H2,1-8H3

InChI Key

GGGUGZHBAOMSFJ-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as scalarane sesterterpenoids. These are sesterterpenoids with a structure based on the scalarane backbone. Scalarane is a tetracyclic compound, which is similar the homoandrostane with five methyl groups at the 4-, 4-, 8-, 17-, 17a-positions.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesterterpenoids

Direct Parent

Scalarane sesterterpenoids

Alternative Parents

Substituents

Scalarane sesterterpenoid
Cyclic alcohol
Secondary alcohol
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Alcohol
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

a triterpenoid (CPD-10667 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cytoplasm (HMDB: HMDB0034920)
Cell membrane (HMDB: HMDB0034920)

Cellular substructure

Extracellular (HMDB: HMDB0034920)
Membrane (HMDB: HMDB0034920)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0034920)

Animal (HMDB: HMDB0034920)

Endogenous (HMDB: HMDB0034920)

Exogenous

Food

Food (HMDB: HMDB0034920)

Herbs and Spices (FooDB: FOOD00866)

Nut

Almond (FooDB: FOOD00148)
Brazil nut (FooDB: FOOD00024)
Cashew nut (FooDB: FOOD00011)
Chestnut (FooDB: FOOD00045)
Hazelnut (FooDB: FOOD00376)
Peanut (FooDB: FOOD00016)
Pecan nut (FooDB: FOOD00044)
Pine nut (FooDB: FOOD00138)
Pistachio (FooDB: FOOD00140)
Walnut (FooDB: FOOD00608)
Acorn (FooDB: FOOD00282)
Beech nut (FooDB: FOOD00299)
Butternut (FooDB: FOOD00316)
Chinese chestnut (FooDB: FOOD00331)
European chestnut (FooDB: FOOD00363)
Hickory nut (FooDB: FOOD00377)
Macadamia nut (FooDB: FOOD00525)
Mixed nuts (FooDB: FOOD00771)
Pili nut (FooDB: FOOD00432)
Colorado pinyon (FooDB: FOOD00433)
Black walnut (FooDB: FOOD00093)
Common walnut (FooDB: FOOD00094)
Japanese chestnut (FooDB: FOOD00385)
Common hazelnut (FooDB: FOOD00062)
Macadamia nut (M. tetraphylla) (FooDB: FOOD00225)
Japanese walnut (FooDB: FOOD00240)
Nuts (FooDB: FOOD00869)

Fruit

Pome

Drupe

Apricot (FooDB: FOOD00144)
Prunus (Cherry, Plum) (FooDB: FOOD00143)
Nectarine (FooDB: FOOD00229)
Peach (FooDB: FOOD00149)
European plum (FooDB: FOOD00147)
Sour cherry (FooDB: FOOD00146)
Sweet cherry (FooDB: FOOD00145)
Common chokecherry (FooDB: FOOD00562)
Peach (var.) (FooDB: FOOD00230)

Tropical fruit

Berry

Bilberry (FooDB: FOOD00193)
Rubus (Blackberry, Raspberry) (FooDB: FOOD00160)
Vaccinium (Blueberry, Cranberry, Huckleberry) (FooDB: FOOD00188)
Blackcurrant (FooDB: FOOD00155)
Redcurrant (FooDB: FOOD00156)
Elderberry (FooDB: FOOD00358)
Gooseberry (FooDB: FOOD00157)
Grape (FooDB: FOOD00369)
Lingonberry (FooDB: FOOD00194)
Loganberry (FooDB: FOOD00400)
Strawberry (FooDB: FOOD00083)
Boysenberry (FooDB: FOOD00542)
American cranberry (FooDB: FOOD00192)
Common grape (FooDB: FOOD00204)
Strawberry guava (FooDB: FOOD00482)
Black mulberry (FooDB: FOOD00117)
Red raspberry (FooDB: FOOD00162)
Muscadine grape (FooDB: FOOD00203)
Salmonberry (FooDB: FOOD00456)
Alaska blueberry (FooDB: FOOD00380)
Sea-buckthornberry (FooDB: FOOD00087)
Black elderberry (FooDB: FOOD00166)
Black crowberry (FooDB: FOOD00075)
Black huckleberry (FooDB: FOOD00084)
Mulberry (FooDB: FOOD00116)
Black chokeberry (FooDB: FOOD00136)
Cloudberry (FooDB: FOOD00161)
Black raspberry (FooDB: FOOD00163)
Rowanberry (FooDB: FOOD00176)
Lowbush blueberry (FooDB: FOOD00189)
Sparkleberry (FooDB: FOOD00190)
Highbush blueberry (FooDB: FOOD00191)
Arctic blackberry (FooDB: FOOD00207)
Bayberry (FooDB: FOOD00209)
Elliott's blueberry (FooDB: FOOD00210)
Canada blueberry (FooDB: FOOD00211)
Bog bilberry (FooDB: FOOD00212)
Buffalo currant (FooDB: FOOD00213)
European cranberry (FooDB: FOOD00217)
Deerberry (FooDB: FOOD00218)
Cascade huckleberry (FooDB: FOOD00220)
Oval-leaf huckleberry (FooDB: FOOD00221)
Evergreen huckleberry (FooDB: FOOD00222)
Red huckleberry (FooDB: FOOD00223)
Summer grape (FooDB: FOOD00227)
Fox grape (FooDB: FOOD00228)
Half-highbush blueberry (FooDB: FOOD00248)
Jostaberry (FooDB: FOOD00257)
Sweet rowanberry (FooDB: FOOD00265)
Skunk currant (FooDB: FOOD00267)
Squashberry (FooDB: FOOD00344)
Ohelo berry (FooDB: FOOD00419)
Chinese bayberry (FooDB: FOOD00852)
Saskatoon berry (FooDB: FOOD00884)
Nanking cherry (FooDB: FOOD00885)

Other fruit

Date (FooDB: FOOD00135)
Fig (FooDB: FOOD00081)
Jujube (FooDB: FOOD00388)

Citrus

Grapefruit (FooDB: FOOD00256)
Lemon (FooDB: FOOD00054)
Lime (FooDB: FOOD00053)
Sweet orange (FooDB: FOOD00057)
Mandarin orange (Clementine, Tangerine) (FooDB: FOOD00056)
Persian lime (FooDB: FOOD00543)
Pummelo (FooDB: FOOD00055)
Grapefruit/Pummelo hybrid (FooDB: FOOD00255)
Citrus (FooDB: FOOD00859)

Fruits (FooDB: FOOD00871)

Vegetable

Shoot vegetable

Fruit vegetable

Eggplant (FooDB: FOOD00174)
Avocado (FooDB: FOOD00130)
Groundcherry (FooDB: FOOD00371)
Olive (FooDB: FOOD00121)
Pepper (FooDB: FOOD00040)
Garden tomato (FooDB: FOOD00171)
Mexican groundcherry (FooDB: FOOD00491)
Green bell pepper (FooDB: FOOD00877)
Yellow bell pepper (FooDB: FOOD00878)
Red bell pepper (FooDB: FOOD00880)
Italian sweet red pepper (FooDB: FOOD00881)
Garden tomato (var.) (FooDB: FOOD00173)
Cherry tomato (FooDB: FOOD00172)
Pepper (C. baccatum) (FooDB: FOOD00231)
Pepper (C. chinense) (FooDB: FOOD00232)
Pepper (Capsicum) (FooDB: FOOD00233)
Pepper (C. frutescens) (FooDB: FOOD00428)
Pepper (C. pubescens) (FooDB: FOOD00849)
Orange bell pepper (FooDB: FOOD00879)

Root vegetable

Cabbage

Leaf vegetable

Lettuce (FooDB: FOOD00095)
Swiss chard (FooDB: FOOD00237)
Garden cress (FooDB: FOOD00099)
Endive (FooDB: FOOD00048)
Spinach (FooDB: FOOD00178)
Common beet (FooDB: FOOD00025)
Garland chrysanthemum (FooDB: FOOD00333)
Jute (FooDB: FOOD00389)
Lambsquarters (FooDB: FOOD00394)
New Zealand spinach (FooDB: FOOD00415)
Swamp cabbage (FooDB: FOOD00091)
Rocket salad (ssp.) (FooDB: FOOD00077)
Yautia (FooDB: FOOD00510)
Romaine lettuce (FooDB: FOOD00888)
Rocket salad (FooDB: FOOD00244)
Chicory leaves (FooDB: FOOD00250)
Corn salad (FooDB: FOOD00340)
Malabar spinach (FooDB: FOOD00404)
Ostrich fern (FooDB: FOOD00556)
Green vegetables (FooDB: FOOD00872)

Mushroom

Tuber

Onion-family vegetable

Leek (FooDB: FOOD00007)
Allium (FooDB: FOOD00005)
Wild leek (FooDB: FOOD00396)
Shallot (FooDB: FOOD00243)
Garden onion (FooDB: FOOD00006)
Garden onion (var.) (FooDB: FOOD00226)
Onion-family vegetables (FooDB: FOOD00855)
Green onion (FooDB: FOOD00963)
Red onion (FooDB: FOOD00962)

Other vegetable

Okra (FooDB: FOOD00420)
Horseradish tree (FooDB: FOOD00379)
Sacred lotus (FooDB: FOOD00402)
Tree fern (FooDB: FOOD00797)
Chinese water chestnut (FooDB: FOOD00332)
Nopal (FooDB: FOOD00416)
Carob (FooDB: FOOD00321)
Agave (FooDB: FOOD00563)
Narrowleaf cattail (FooDB: FOOD00564)
Giant butterbur (FooDB: FOOD00314)
Sesbania flower (FooDB: FOOD00469)

Stalk vegetable

Brassica

Brassicas (FooDB: FOOD00857)

Cereal and cereal product

Other bread

Other bread (FooDB: FOOD00269)

Cereal

Cereal product

Dough

Sourdough (FooDB: FOOD00275)

Cereals and cereal products (FooDB: FOOD00858)

Pulse

Bean

Lentil

Lentils (FooDB: FOOD00098)

Pea

Other pulse

White lupine (FooDB: FOOD00403)
Lupine (FooDB: FOOD00104)

Pulses (FooDB: FOOD00867)

Soy

Soy bean (FooDB: FOOD00085)

Soy product

Other soy product (FooDB: FOOD00271)

Abalone (FooDB: FOOD00279)
Conch (FooDB: FOOD00611)

Gourd

Chayote (FooDB: FOOD00325)
Cucumber (FooDB: FOOD00065)
Muskmelon (FooDB: FOOD00064)
Cucurbita (FooDB: FOOD00066)
Watermelon (FooDB: FOOD00052)
Bitter gourd (FooDB: FOOD00115)
Calabash (FooDB: FOOD00318)
Towel gourd (FooDB: FOOD00492)
Winter squash (FooDB: FOOD00283)
Butternut squash (FooDB: FOOD00317)
Wax gourd (FooDB: FOOD00499)
Green zucchini (FooDB: FOOD00875)
Yellow zucchini (FooDB: FOOD00876)
Japanese pumpkin (FooDB: FOOD00886)
Sunburst squash (pattypan squash) (FooDB: FOOD00874)
Tinda (FooDB: FOOD00559)
Horned melon (FooDB: FOOD00761)

Tea

Herbal tea

Greenthread tea (FooDB: FOOD00820)

Coffee and coffee product

Coffee

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

Coffee and coffee products (FooDB: FOOD00861)

Cocoa and cocoa product

Cocoa

Cocoa bean (FooDB: FOOD00182)

Beverage

Alcoholic beverage

Alcoholic beverages (FooDB: FOOD00854)

Beverages (FooDB: FOOD00870)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid peroxidation (HMDB: HMDB0034920)

Biochemical process

Fatty acid metabolism (HMDB: HMDB0034920)

Cellular process

Cell signaling (HMDB: HMDB0034920)

Biochemical pathway

Lipid metabolism pathway (HMDB: HMDB0034920)

Role

Biological role

Nutrient

Nutrient (HMDB: HMDB0034920)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0034920)

Emulsifier (HMDB: HMDB0034920)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	282 - 283 °C	Not Available
Boiling Point	409.00 to 410.00 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Water Solubility	0	The Good Scents Company Information System
LogP	3.195 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	6.9e-05 g/L	ALOGPS
logP	7.2	ALOGPS
logP	7.4	ChemAxon
logS	-6.8	ALOGPS
pKa (Strongest Acidic)	19.49	ChemAxon
pKa (Strongest Basic)	-0.84	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	20.23 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	131.91 m³·mol⁻¹	ChemAxon
Polarizability	54.39 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	199.461	31661259
DarkChem	[M-H]-	194.187	31661259
DeepCCS	[M+H]+	213.294	30932474
DeepCCS	[M-H]-	210.936	30932474
DeepCCS	[M-2H]-	244.888	30932474
DeepCCS	[M+Na]+	220.116	30932474
AllCCS	[M+H]+	217.8	32859911
AllCCS	[M+H-H2O]+	216.0	32859911
AllCCS	[M+NH4]+	219.4	32859911
AllCCS	[M+Na]+	219.9	32859911
AllCCS	[M-H]-	213.3	32859911
AllCCS	[M+Na-2H]-	215.0	32859911
AllCCS	[M+HCOO]-	217.1	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Taraxerol	CC1(C)CCC2(C)CC=C3C4(C)CCC5C(C)(C)C(O)CCC5(C)C4CCC3(C)C2C1	2663.6	Standard polar	33892256
Taraxerol	CC1(C)CCC2(C)CC=C3C4(C)CCC5C(C)(C)C(O)CCC5(C)C4CCC3(C)C2C1	3392.6	Standard non polar	33892256
Taraxerol	CC1(C)CCC2(C)CC=C3C4(C)CCC5C(C)(C)C(O)CCC5(C)C4CCC3(C)C2C1	3393.0	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Taraxerol,1TMS,isomer #1	CC1(C)CCC2(C)CC=C3C(C)(CCC4C3(C)CCC3C(C)(C)C(O[Si](C)(C)C)CCC43C)C2C1	3354.9	Semi standard non polar	33892256
Taraxerol,1TBDMS,isomer #1	CC1(C)CCC2(C)CC=C3C(C)(CCC4C3(C)CCC3C(C)(C)C(O[Si](C)(C)C(C)(C)C)CCC43C)C2C1	3597.6	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 - Taraxerol GC-MS (Non-derivatized) - 70eV, Positive	splash10-03dj-0219500000-793fa49b829c7c970964	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Taraxerol GC-MS (1 TMS) - 70eV, Positive	splash10-001i-1011900000-186d7d36edca5fd91622	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Taraxerol 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 - Taraxerol 10V, Positive-QTOF	splash10-0a6r-0001900000-55a012724749e9910efc	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Taraxerol 20V, Positive-QTOF	splash10-0a6r-1668900000-a815b8aa5a8e77b3948e	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Taraxerol 40V, Positive-QTOF	splash10-0hh0-1569100000-12304aa318eaca43c7bd	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Taraxerol 10V, Negative-QTOF	splash10-004i-0000900000-a5f272b047d0bed70dd5	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Taraxerol 20V, Negative-QTOF	splash10-004i-0000900000-b12658710e0349eca4fb	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Taraxerol 40V, Negative-QTOF	splash10-052f-1019500000-0c45941ca686fb4d77cf	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Taraxerol 10V, Positive-QTOF	splash10-004i-0002900000-17e13fb85ee36d97d468	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Taraxerol 20V, Positive-QTOF	splash10-0a4i-2219300000-a65a5f1cae40e7e77a37	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Taraxerol 40V, Positive-QTOF	splash10-000f-2920000000-392cc5c23c3270d14a28	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Taraxerol 10V, Negative-QTOF	splash10-004i-0000900000-590c9e4adfdd12b64d93	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Taraxerol 20V, Negative-QTOF	splash10-004i-0000900000-590c9e4adfdd12b64d93	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Taraxerol 40V, Negative-QTOF	splash10-004i-0000900000-590c9e4adfdd12b64d93	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

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Taraxerol

METLIN ID

Not Available

PubChem Compound

344467

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1594101

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 ]
Sharma K, Zafar R: Occurrence of taraxerol and taraxasterol in medicinal plants. Pharmacogn Rev. 2015 Jan-Jun;9(17):19-23. doi: 10.4103/0973-7847.156317. [PubMed:26009688 ]
Takasaki M, Konoshima T, Tokuda H, Masuda K, Arai Y, Shiojima K, Ageta H: Anti-carcinogenic activity of Taraxacum plant. II. Biol Pharm Bull. 1999 Jun;22(6):606-10. doi: 10.1248/bpb.22.606. [PubMed:10408235 ]
(). 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 Taraxerol (HMDB0034920)

MOL for HMDB0034920 (Taraxerol)

3D MOL for HMDB0034920 (Taraxerol)

3D SDF for HMDB0034920 (Taraxerol)

3D-SDF for HMDB0034920 (Taraxerol)

PDB for HMDB0034920 (Taraxerol)

3D PDB for HMDB0034920 (Taraxerol)

SMILES for HMDB0034920 (Taraxerol)

INCHI for HMDB0034920 (Taraxerol)

Structure for HMDB0034920 (Taraxerol)

3D Structure for HMDB0034920 (Taraxerol)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra