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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 20:44:12 UTC

Update Date

2022-03-07 02:54:36 UTC

HMDB ID

HMDB0035722

Secondary Accession Numbers

HMDB35722

Metabolite Identification

Common Name

Tanacetol A

Description

Tanacetol A belongs to the class of organic compounds known as germacrane sesquiterpenoids. These are sesquiterpenoids having the germacrane skeleton, with a structure characterized by a cyclodecane ring substituted with an isopropyl and two methyl groups. Based on a literature review a small amount of articles have been published on Tanacetol A.

Structure

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

HMDB0035722
     RDKit          3D
Tanacetol A
 47 47  0  0  0  0  0  0  0  0999 V2000
    0.8678   -3.9938   -0.3252 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2564   -2.8191   -0.3809 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1196   -1.6736   -0.8163 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7134   -1.0224    0.3829 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0219    0.3962    0.3145 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3762    0.7653    0.5896 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2881    0.8246   -0.4558 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7035    1.1924   -0.2851 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8776    0.5485   -1.6073 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2703    1.4298    0.0402 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8745    2.8368    0.0412 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1721    1.4290   -0.2972 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0502    0.7588    0.7187 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8853   -0.2970    0.0126 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3618    0.1296   -0.0027 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4421    1.4635   -0.7526 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8996    0.3521    1.3686 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1190   -0.7709   -0.7331 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7584   -1.5816    0.7362 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1495   -2.6791   -0.0374 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9125   -3.5958   -0.4490 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9150   -4.1307   -0.5733 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020   -4.8521   -0.0236 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9318   -2.1476   -1.4551 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6150   -1.0247   -1.5321 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6856   -1.5964    0.5761 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1256   -1.3389    1.2990 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0284    1.1552    0.7707 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9277    2.2088   -0.6589 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3235    0.4909   -0.8933 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1841    3.4139    0.7126 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8974    3.2441   -0.9741 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8506    2.8544    0.5067 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3944    1.0546   -1.3241 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5641    2.4964   -0.3804 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4597    0.3560    1.5626 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7175    1.5205    1.2105 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6298   -0.3581   -1.0782 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8054    1.3769   -1.6734 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4724    1.6774   -1.0762 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0823    2.2883   -0.1316 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0011    0.1832    1.3459 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4986   -0.3190    2.1401 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7825    1.4360    1.6536 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0120   -0.3861   -0.8455 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7716   -1.9010    1.0760 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2141   -1.3955    1.7042 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  2  0
  5 10  2  0
 10 11  1  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 15 17  1  0
 15 18  1  0
 14 19  1  0
 19 20  1  0
 20 21  2  0
 20  2  1  0
  1 22  1  0
  1 23  1  0
  3 24  1  0
  3 25  1  0
  4 26  1  0
  4 27  1  0
  8 28  1  0
  8 29  1  0
  8 30  1  0
 11 31  1  0
 11 32  1  0
 11 33  1  0
 12 34  1  0
 12 35  1  0
 13 36  1  0
 13 37  1  0
 14 38  1  0
 16 39  1  0
 16 40  1  0
 16 41  1  0
 17 42  1  0
 17 43  1  0
 17 44  1  0
 18 45  1  0
 19 46  1  0
 19 47  1  0
M  END


  Mrv0541 05061308402D          

 21 21  0  0  0  0            999 V2000
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6039    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2539    1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  8  6  1  0  0  0  0
  9  7  1  0  0  0  0
 11  1  2  0  0  0  0
 11  7  1  0  0  0  0
 12  2  1  0  0  0  0
 12  6  1  0  0  0  0
 13  3  1  0  0  0  0
 14  8  1  0  0  0  0
 14 10  1  0  0  0  0
 15 10  1  0  0  0  0
 15 11  1  0  0  0  0
 16  9  1  0  0  0  0
 16 12  2  0  0  0  0
 17  4  1  0  0  0  0
 17  5  1  0  0  0  0
 17 14  1  0  0  0  0
 18 13  2  0  0  0  0
 19 15  2  0  0  0  0
 20 17  1  0  0  0  0
 21 13  1  0  0  0  0
 21 16  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0035722

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(=O)O\C1=C(C)\CCC(CC(=O)C(=C)CC1)C(C)(C)O

> <INCHI_IDENTIFIER>
InChI=1S/C17H26O4/c1-11-7-9-16(21-13(3)18)12(2)6-8-14(10-15(11)19)17(4,5)20/h14,20H,1,6-10H2,2-5H3/b16-12+

> <INCHI_KEY>
IULUGGNZUILXOI-FOWTUZBSSA-N

> <FORMULA>
C17H26O4

> <MOLECULAR_WEIGHT>
294.3859

> <EXACT_MASS>
294.18310932

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
32.67987463902044

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1E)-5-(2-hydroxypropan-2-yl)-2-methyl-8-methylidene-7-oxocyclodec-1-en-1-yl acetate

> <ALOGPS_LOGP>
2.29

> <JCHEM_LOGP>
2.3087340286666667

> <ALOGPS_LOGS>
-3.34

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
19.090350316395533

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.051321477103631

> <JCHEM_PKA_STRONGEST_BASIC>
-2.7762633096974954

> <JCHEM_POLAR_SURFACE_AREA>
63.60000000000001

> <JCHEM_REFRACTIVITY>
83.08299999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.36e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1E)-5-(2-hydroxypropan-2-yl)-2-methyl-8-methylidene-7-oxocyclodec-1-en-1-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0035722
     RDKit          3D
Tanacetol A
 47 47  0  0  0  0  0  0  0  0999 V2000
    0.8678   -3.9938   -0.3252 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2564   -2.8191   -0.3809 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1196   -1.6736   -0.8163 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7134   -1.0224    0.3829 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0219    0.3962    0.3145 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3762    0.7653    0.5896 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2881    0.8246   -0.4558 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7035    1.1924   -0.2851 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8776    0.5485   -1.6073 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2703    1.4298    0.0402 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8745    2.8368    0.0412 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1721    1.4290   -0.2972 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0502    0.7588    0.7187 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8853   -0.2970    0.0126 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3618    0.1296   -0.0027 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4421    1.4635   -0.7526 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8996    0.3521    1.3686 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1190   -0.7709   -0.7331 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7584   -1.5816    0.7362 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1495   -2.6791   -0.0374 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9125   -3.5958   -0.4490 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9150   -4.1307   -0.5733 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020   -4.8521   -0.0236 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9318   -2.1476   -1.4551 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6150   -1.0247   -1.5321 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6856   -1.5964    0.5761 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1256   -1.3389    1.2990 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0284    1.1552    0.7707 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9277    2.2088   -0.6589 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3235    0.4909   -0.8933 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1841    3.4139    0.7126 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8974    3.2441   -0.9741 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8506    2.8544    0.5067 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3944    1.0546   -1.3241 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5641    2.4964   -0.3804 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4597    0.3560    1.5626 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7175    1.5205    1.2105 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6298   -0.3581   -1.0782 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8054    1.3769   -1.6734 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4724    1.6774   -1.0762 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0823    2.2883   -0.1316 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0011    0.1832    1.3459 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4986   -0.3190    2.1401 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7825    1.4360    1.6536 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0120   -0.3861   -0.8455 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7716   -1.9010    1.0760 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2141   -1.3955    1.7042 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  2  0
  5 10  2  0
 10 11  1  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 15 17  1  0
 15 18  1  0
 14 19  1  0
 19 20  1  0
 20 21  2  0
 20  2  1  0
  1 22  1  0
  1 23  1  0
  3 24  1  0
  3 25  1  0
  4 26  1  0
  4 27  1  0
  8 28  1  0
  8 29  1  0
  8 30  1  0
 11 31  1  0
 11 32  1  0
 11 33  1  0
 12 34  1  0
 12 35  1  0
 13 36  1  0
 13 37  1  0
 14 38  1  0
 16 39  1  0
 16 40  1  0
 16 41  1  0
 17 42  1  0
 17 43  1  0
 17 44  1  0
 18 45  1  0
 19 46  1  0
 19 47  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      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.127   3.080   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.667   3.080   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      -1.334   2.310   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       4.207   3.080   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       4.001  -2.310   0.000  0.00  0.00           O+0
CONECT    1   11                                                            
CONECT    2   12                                                            
CONECT    3   13                                                            
CONECT    4   17                                                            
CONECT    5   17                                                            
CONECT    6    8   12                                                       
CONECT    7    9   11                                                       
CONECT    8    6   14                                                       
CONECT    9    7   16                                                       
CONECT   10   14   15                                                       
CONECT   11    1    7   15                                                  
CONECT   12    2    6   16                                                  
CONECT   13    3   18   21                                                  
CONECT   14    8   10   17                                                  
CONECT   15   10   11   19                                                  
CONECT   16    9   12   21                                                  
CONECT   17    4    5   14   20                                             
CONECT   18   13                                                            
CONECT   19   15                                                            
CONECT   20   17                                                            
CONECT   21   13   16                                                       
MASTER        0    0    0    0    0    0    0    0   21    0   42    0
END

COMPND    HMDB0035722
HETATM    1  C1  UNL     1       0.868  -3.994  -0.325  1.00  0.00           C  
HETATM    2  C2  UNL     1       0.256  -2.819  -0.381  1.00  0.00           C  
HETATM    3  C3  UNL     1       1.120  -1.674  -0.816  1.00  0.00           C  
HETATM    4  C4  UNL     1       1.713  -1.022   0.383  1.00  0.00           C  
HETATM    5  C5  UNL     1       2.022   0.396   0.314  1.00  0.00           C  
HETATM    6  O1  UNL     1       3.376   0.765   0.590  1.00  0.00           O  
HETATM    7  C6  UNL     1       4.288   0.825  -0.456  1.00  0.00           C  
HETATM    8  C7  UNL     1       5.703   1.192  -0.285  1.00  0.00           C  
HETATM    9  O2  UNL     1       3.878   0.548  -1.607  1.00  0.00           O  
HETATM   10  C8  UNL     1       1.270   1.430   0.040  1.00  0.00           C  
HETATM   11  C9  UNL     1       1.874   2.837   0.041  1.00  0.00           C  
HETATM   12  C10 UNL     1      -0.172   1.429  -0.297  1.00  0.00           C  
HETATM   13  C11 UNL     1      -1.050   0.759   0.719  1.00  0.00           C  
HETATM   14  C12 UNL     1      -1.885  -0.297   0.013  1.00  0.00           C  
HETATM   15  C13 UNL     1      -3.362   0.130  -0.003  1.00  0.00           C  
HETATM   16  C14 UNL     1      -3.442   1.464  -0.753  1.00  0.00           C  
HETATM   17  C15 UNL     1      -3.900   0.352   1.369  1.00  0.00           C  
HETATM   18  O3  UNL     1      -4.119  -0.771  -0.733  1.00  0.00           O  
HETATM   19  C16 UNL     1      -1.758  -1.582   0.736  1.00  0.00           C  
HETATM   20  C17 UNL     1      -1.150  -2.679  -0.037  1.00  0.00           C  
HETATM   21  O4  UNL     1      -1.912  -3.596  -0.449  1.00  0.00           O  
HETATM   22  H1  UNL     1       1.915  -4.131  -0.573  1.00  0.00           H  
HETATM   23  H2  UNL     1       0.302  -4.852  -0.024  1.00  0.00           H  
HETATM   24  H3  UNL     1       1.932  -2.148  -1.455  1.00  0.00           H  
HETATM   25  H4  UNL     1       0.615  -1.025  -1.532  1.00  0.00           H  
HETATM   26  H5  UNL     1       2.686  -1.596   0.576  1.00  0.00           H  
HETATM   27  H6  UNL     1       1.126  -1.339   1.299  1.00  0.00           H  
HETATM   28  H7  UNL     1       6.028   1.155   0.771  1.00  0.00           H  
HETATM   29  H8  UNL     1       5.928   2.209  -0.659  1.00  0.00           H  
HETATM   30  H9  UNL     1       6.324   0.491  -0.893  1.00  0.00           H  
HETATM   31  H10 UNL     1       1.184   3.414   0.713  1.00  0.00           H  
HETATM   32  H11 UNL     1       1.897   3.244  -0.974  1.00  0.00           H  
HETATM   33  H12 UNL     1       2.851   2.854   0.507  1.00  0.00           H  
HETATM   34  H13 UNL     1      -0.394   1.055  -1.324  1.00  0.00           H  
HETATM   35  H14 UNL     1      -0.564   2.496  -0.380  1.00  0.00           H  
HETATM   36  H15 UNL     1      -0.460   0.356   1.563  1.00  0.00           H  
HETATM   37  H16 UNL     1      -1.717   1.520   1.210  1.00  0.00           H  
HETATM   38  H17 UNL     1      -1.630  -0.358  -1.078  1.00  0.00           H  
HETATM   39  H18 UNL     1      -2.805   1.377  -1.673  1.00  0.00           H  
HETATM   40  H19 UNL     1      -4.472   1.677  -1.076  1.00  0.00           H  
HETATM   41  H20 UNL     1      -3.082   2.288  -0.132  1.00  0.00           H  
HETATM   42  H21 UNL     1      -5.001   0.183   1.346  1.00  0.00           H  
HETATM   43  H22 UNL     1      -3.499  -0.319   2.140  1.00  0.00           H  
HETATM   44  H23 UNL     1      -3.783   1.436   1.654  1.00  0.00           H  
HETATM   45  H24 UNL     1      -5.012  -0.386  -0.845  1.00  0.00           H  
HETATM   46  H25 UNL     1      -2.772  -1.901   1.076  1.00  0.00           H  
HETATM   47  H26 UNL     1      -1.214  -1.396   1.704  1.00  0.00           H  
CONECT    1    2    2   22   23
CONECT    2    3   20
CONECT    3    4   24   25
CONECT    4    5   26   27
CONECT    5    6   10   10
CONECT    6    7
CONECT    7    8    9    9
CONECT    8   28   29   30
CONECT   10   11   12
CONECT   11   31   32   33
CONECT   12   13   34   35
CONECT   13   14   36   37
CONECT   14   15   19   38
CONECT   15   16   17   18
CONECT   16   39   40   41
CONECT   17   42   43   44
CONECT   18   45
CONECT   19   20   46   47
CONECT   20   21   21
END

HMDB0035722
     RDKit          3D
Tanacetol A
 47 47  0  0  0  0  0  0  0  0999 V2000
    0.8678   -3.9938   -0.3252 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2564   -2.8191   -0.3809 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1196   -1.6736   -0.8163 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7134   -1.0224    0.3829 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0219    0.3962    0.3145 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3762    0.7653    0.5896 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2881    0.8246   -0.4558 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7035    1.1924   -0.2851 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8776    0.5485   -1.6073 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2703    1.4298    0.0402 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8745    2.8368    0.0412 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1721    1.4290   -0.2972 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0502    0.7588    0.7187 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8853   -0.2970    0.0126 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3618    0.1296   -0.0027 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4421    1.4635   -0.7526 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8996    0.3521    1.3686 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1190   -0.7709   -0.7331 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7584   -1.5816    0.7362 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1495   -2.6791   -0.0374 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9125   -3.5958   -0.4490 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9150   -4.1307   -0.5733 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020   -4.8521   -0.0236 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9318   -2.1476   -1.4551 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6150   -1.0247   -1.5321 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6856   -1.5964    0.5761 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1256   -1.3389    1.2990 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0284    1.1552    0.7707 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9277    2.2088   -0.6589 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3235    0.4909   -0.8933 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1841    3.4139    0.7126 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8974    3.2441   -0.9741 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8506    2.8544    0.5067 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3944    1.0546   -1.3241 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5641    2.4964   -0.3804 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4597    0.3560    1.5626 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7175    1.5205    1.2105 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6298   -0.3581   -1.0782 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8054    1.3769   -1.6734 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4724    1.6774   -1.0762 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0823    2.2883   -0.1316 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0011    0.1832    1.3459 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4986   -0.3190    2.1401 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7825    1.4360    1.6536 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0120   -0.3861   -0.8455 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7716   -1.9010    1.0760 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2141   -1.3955    1.7042 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  2  0
  5 10  2  0
 10 11  1  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 15 17  1  0
 15 18  1  0
 14 19  1  0
 19 20  1  0
 20 21  2  0
 20  2  1  0
  1 22  1  0
  1 23  1  0
  3 24  1  0
  3 25  1  0
  4 26  1  0
  4 27  1  0
  8 28  1  0
  8 29  1  0
  8 30  1  0
 11 31  1  0
 11 32  1  0
 11 33  1  0
 12 34  1  0
 12 35  1  0
 13 36  1  0
 13 37  1  0
 14 38  1  0
 16 39  1  0
 16 40  1  0
 16 41  1  0
 17 42  1  0
 17 43  1  0
 17 44  1  0
 18 45  1  0
 19 46  1  0
 19 47  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(-)-Tanacetol a	HMDB
2-Acetoxy-11-hydroxy-1(10),4(15)-germacradien-5-one	HMDB
(1E)-5-(2-Hydroxypropan-2-yl)-2-methyl-8-methylidene-7-oxocyclodec-1-en-1-yl acetic acid	Generator

Chemical Formula

C₁₇H₂₆O₄

Average Molecular Weight

294.3859

Monoisotopic Molecular Weight

294.18310932

IUPAC Name

(1E)-5-(2-hydroxypropan-2-yl)-2-methyl-8-methylidene-7-oxocyclodec-1-en-1-yl acetate

Traditional Name

(1E)-5-(2-hydroxypropan-2-yl)-2-methyl-8-methylidene-7-oxocyclodec-1-en-1-yl acetate

CAS Registry Number

86778-06-5

SMILES

CC(=O)O\C1=C(C)\CCC(CC(=O)C(=C)CC1)C(C)(C)O

InChI Identifier

InChI=1S/C17H26O4/c1-11-7-9-16(21-13(3)18)12(2)6-8-14(10-15(11)19)17(4,5)20/h14,20H,1,6-10H2,2-5H3/b16-12+

InChI Key

IULUGGNZUILXOI-FOWTUZBSSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as germacrane sesquiterpenoids. These are sesquiterpenoids having the germacrane skeleton, with a structure characterized by a cyclodecane ring substituted with an isopropyl and two methyl groups.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Germacrane sesquiterpenoids

Alternative Parents

Substituents

Germacrane sesquiterpenoid
Tertiary alcohol
Enol ester
Cyclic ketone
Ketone
Carboxylic acid ester
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cell membrane (HMDB: HMDB0035722)

Cellular substructure

Route of exposure

Enteral

Ingestion (HMDB: HMDB0035722)

Source

Endogenous

Endogenous (HMDB: HMDB0035722)

Plant

Plant (HMDB: HMDB0035722)

Animal

Animal (HMDB: HMDB0035722)

Exogenous

Food

Food (HMDB: HMDB0035722)

Herb and spice

Herbs and Spices (FooDB: FOOD00866)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid peroxidation (HMDB: HMDB0035722)

Biochemical process

Fatty acid metabolism (HMDB: HMDB0035722)

Cellular process

Cell signaling (HMDB: HMDB0035722)

Biochemical pathway

Lipid metabolism pathway (HMDB: HMDB0035722)

Role

Biological role

Membrane stabilizer (HMDB: HMDB0035722)

Nutrient

Nutrient (HMDB: HMDB0035722)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0035722)

Emulsifier (HMDB: HMDB0035722)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	98 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	52.11 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.14 g/L	ALOGPS
logP	2.29	ALOGPS
logP	2.31	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Acidic)	15.05	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	63.6 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	83.08 m³·mol⁻¹	ChemAxon
Polarizability	32.68 Å³	ChemAxon
Number of Rings	1	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]+	170.978	31661259
DarkChem	[M-H]-	165.647	31661259
DeepCCS	[M+H]+	172.565	30932474
DeepCCS	[M-H]-	170.207	30932474
DeepCCS	[M-2H]-	204.04	30932474
DeepCCS	[M+Na]+	179.267	30932474
AllCCS	[M+H]+	171.8	32859911
AllCCS	[M+H-H2O]+	168.5	32859911
AllCCS	[M+NH4]+	174.8	32859911
AllCCS	[M+Na]+	175.6	32859911
AllCCS	[M-H]-	175.2	32859911
AllCCS	[M+Na-2H]-	175.9	32859911
AllCCS	[M+HCOO]-	176.7	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Tanacetol A	CC(=O)O\C1=C(C)\CCC(CC(=O)C(=C)CC1)C(C)(C)O	2877.3	Standard polar	33892256
Tanacetol A	CC(=O)O\C1=C(C)\CCC(CC(=O)C(=C)CC1)C(C)(C)O	2055.4	Standard non polar	33892256
Tanacetol A	CC(=O)O\C1=C(C)\CCC(CC(=O)C(=C)CC1)C(C)(C)O	2092.5	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Tanacetol A,1TMS,isomer #1	C=C1CC/C(OC(C)=O)=C(/C)CCC(C(C)(C)O[Si](C)(C)C)CC1=O	2235.2	Semi standard non polar	33892256
Tanacetol A,1TMS,isomer #2	C=C1CC/C(OC(C)=O)=C(/C)CCC(C(C)(C)O)C=C1O[Si](C)(C)C	2237.8	Semi standard non polar	33892256
Tanacetol A,2TMS,isomer #1	C=C1CC/C(OC(C)=O)=C(/C)CCC(C(C)(C)O[Si](C)(C)C)C=C1O[Si](C)(C)C	2304.5	Semi standard non polar	33892256
Tanacetol A,2TMS,isomer #1	C=C1CC/C(OC(C)=O)=C(/C)CCC(C(C)(C)O[Si](C)(C)C)C=C1O[Si](C)(C)C	2300.0	Standard non polar	33892256
Tanacetol A,1TBDMS,isomer #1	C=C1CC/C(OC(C)=O)=C(/C)CCC(C(C)(C)O[Si](C)(C)C(C)(C)C)CC1=O	2463.2	Semi standard non polar	33892256
Tanacetol A,1TBDMS,isomer #2	C=C1CC/C(OC(C)=O)=C(/C)CCC(C(C)(C)O)C=C1O[Si](C)(C)C(C)(C)C	2461.4	Semi standard non polar	33892256
Tanacetol A,2TBDMS,isomer #1	C=C1CC/C(OC(C)=O)=C(/C)CCC(C(C)(C)O[Si](C)(C)C(C)(C)C)C=C1O[Si](C)(C)C(C)(C)C	2742.3	Semi standard non polar	33892256
Tanacetol A,2TBDMS,isomer #1	C=C1CC/C(OC(C)=O)=C(/C)CCC(C(C)(C)O[Si](C)(C)C(C)(C)C)C=C1O[Si](C)(C)C(C)(C)C	2531.1	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Tanacetol A GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4i-9050000000-ac7d0e2596c264172cb7	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Tanacetol A GC-MS (1 TMS) - 70eV, Positive	splash10-001l-9723000000-f30ac82dcf41b0cfdaf7	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Tanacetol A 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 - Tanacetol A 10V, Positive-QTOF	splash10-004s-0090000000-13e07b6cf8fc60374282	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tanacetol A 20V, Positive-QTOF	splash10-002r-0390000000-529a18ab069891017586	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tanacetol A 40V, Positive-QTOF	splash10-0zir-9530000000-5d01b716c56c2337e8af	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tanacetol A 10V, Negative-QTOF	splash10-0006-0090000000-0a77607050ca2946b92c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tanacetol A 20V, Negative-QTOF	splash10-0f7o-2190000000-42d7fb2bf88d367d9fd0	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tanacetol A 40V, Negative-QTOF	splash10-0k96-9420000000-9a298adfedb6ad0f90ed	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tanacetol A 10V, Positive-QTOF	splash10-002k-0090000000-8f2355c19aac6bac7c6f	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tanacetol A 20V, Positive-QTOF	splash10-0udi-2090000000-9fed552930de1ffa18bd	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tanacetol A 40V, Positive-QTOF	splash10-00l7-5390000000-971f3b3526f45326246e	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tanacetol A 10V, Negative-QTOF	splash10-0f8c-1090000000-4ec7f483422129e1125b	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tanacetol A 20V, Negative-QTOF	splash10-0zfr-4090000000-35682b90455fca501407	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tanacetol A 40V, Negative-QTOF	splash10-0a4i-9010000000-6a63b8af29ccdc506a73	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
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

FDB014446

KNApSAcK ID

C00011704

Chemspider ID

35014006

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

131751854

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1851161

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 Tanacetol A (HMDB0035722)

MOL for HMDB0035722 (Tanacetol A)

3D MOL for HMDB0035722 (Tanacetol A)

3D SDF for HMDB0035722 (Tanacetol A)

3D-SDF for HMDB0035722 (Tanacetol A)

PDB for HMDB0035722 (Tanacetol A)

3D PDB for HMDB0035722 (Tanacetol A)

SMILES for HMDB0035722 (Tanacetol A)

INCHI for HMDB0035722 (Tanacetol A)

Structure for HMDB0035722 (Tanacetol A)

3D Structure for HMDB0035722 (Tanacetol A)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra