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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 20:01:10 UTC

Update Date

2022-03-07 02:54:21 UTC

HMDB ID

HMDB0035075

Secondary Accession Numbers

HMDB35075

Metabolite Identification

Common Name

Tanacetol B

Description

Tanacetol B 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 B.

Structure

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

HMDB0035075
     RDKit          3D
Tanacetol B
 49 49  0  0  0  0  0  0  0  0999 V2000
   -0.5827    3.6187   -0.0962 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1296    2.4749   -0.6005 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1361    1.6281   -1.2882 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0471    1.0855   -0.2146 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3643   -0.3443   -0.3070 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7611   -0.6439   -0.1479 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1919   -0.8866    1.1407 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6399   -1.2003    1.3320 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4305   -0.8552    2.1415 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5974   -1.3733   -0.5065 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2982   -2.7391   -0.5415 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1486   -1.4610   -0.7122 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7087   -0.7291    0.2802 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9814   -0.2653   -0.3864 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1942   -0.3893    0.4887 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3874    0.1110   -0.3057 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4209   -1.8601    0.7659 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1588    0.2637    1.6806 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8528    1.0227   -1.1228 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2916    2.1739   -0.4253 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5161    2.1765    0.9719 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6236    3.9328   -0.1724 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1169    4.2815    0.4214 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7494    0.9052   -1.9933 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6956    2.3684   -1.9536 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0136    1.6992   -0.3028 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7296    1.4086    0.8269 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9860   -0.8230    2.3078 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8002   -2.3112    1.3297 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2689   -0.7618    0.5573 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3331   -2.6243   -0.8901 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2791   -3.1237    0.4995 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7908   -3.4072   -1.2594 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2113   -2.5402   -0.6449 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2049   -1.1801   -1.7305 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0441   -1.4268    1.1051 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1429    0.0433    0.7625 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1656   -1.0431   -1.1982 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2917   -0.3036    0.2027 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3407   -0.1740   -1.3702 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4851    1.2149   -0.2241 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9500   -2.5100    0.0011 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0081   -2.0948    1.7634 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5171   -2.0188    0.8366 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0692    0.3977    2.0102 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8950    1.2588   -1.5005 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2842    0.8361   -2.0830 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8464    3.1044   -0.7634 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5121    3.0840    1.3155 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  1  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
 20 48  1  0
 21 49  1  0
M  END


  Mrv0541 05061308132D          

 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  1  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>
HMDB0035075

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C17H28O4/c1-11-7-9-16(21-13(3)18)12(2)6-8-14(10-15(11)19)17(4,5)20/h14-15,19-20H,1,6-10H2,2-5H3/b16-12+

> <INCHI_KEY>
QZYCUDRAMHSVOE-FOWTUZBSSA-N

> <FORMULA>
C17H28O4

> <MOLECULAR_WEIGHT>
296.4018

> <EXACT_MASS>
296.198759384

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
33.43323160489566

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
2.26

> <JCHEM_LOGP>
1.7452063230000001

> <ALOGPS_LOGS>
-2.89

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.202726510561977

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.485531060658925

> <JCHEM_PKA_STRONGEST_BASIC>
-2.7711071316799556

> <JCHEM_POLAR_SURFACE_AREA>
66.76

> <JCHEM_REFRACTIVITY>
83.9053

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.83e-01 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0035075
     RDKit          3D
Tanacetol B
 49 49  0  0  0  0  0  0  0  0999 V2000
   -0.5827    3.6187   -0.0962 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1296    2.4749   -0.6005 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1361    1.6281   -1.2882 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0471    1.0855   -0.2146 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3643   -0.3443   -0.3070 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7611   -0.6439   -0.1479 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1919   -0.8866    1.1407 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6399   -1.2003    1.3320 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4305   -0.8552    2.1415 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5974   -1.3733   -0.5065 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2982   -2.7391   -0.5415 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1486   -1.4610   -0.7122 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7087   -0.7291    0.2802 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9814   -0.2653   -0.3864 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1942   -0.3893    0.4887 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3874    0.1110   -0.3057 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4209   -1.8601    0.7659 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1588    0.2637    1.6806 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8528    1.0227   -1.1228 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2916    2.1739   -0.4253 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5161    2.1765    0.9719 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6236    3.9328   -0.1724 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1169    4.2815    0.4214 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7494    0.9052   -1.9933 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6956    2.3684   -1.9536 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0136    1.6992   -0.3028 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7296    1.4086    0.8269 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9860   -0.8230    2.3078 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8002   -2.3112    1.3297 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2689   -0.7618    0.5573 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3331   -2.6243   -0.8901 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2791   -3.1237    0.4995 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7908   -3.4072   -1.2594 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2113   -2.5402   -0.6449 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2049   -1.1801   -1.7305 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0441   -1.4268    1.1051 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1429    0.0433    0.7625 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1656   -1.0431   -1.1982 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2917   -0.3036    0.2027 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3407   -0.1740   -1.3702 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4851    1.2149   -0.2241 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9500   -2.5100    0.0011 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0081   -2.0948    1.7634 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5171   -2.0188    0.8366 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0692    0.3977    2.0102 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8950    1.2588   -1.5005 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2842    0.8361   -2.0830 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8464    3.1044   -0.7634 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5121    3.0840    1.3155 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  1  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
 20 48  1  0
 21 49  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    HMDB0035075
HETATM    1  C1  UNL     1      -0.583   3.619  -0.096  1.00  0.00           C  
HETATM    2  C2  UNL     1      -0.130   2.475  -0.601  1.00  0.00           C  
HETATM    3  C3  UNL     1      -1.136   1.628  -1.288  1.00  0.00           C  
HETATM    4  C4  UNL     1      -2.047   1.085  -0.215  1.00  0.00           C  
HETATM    5  C5  UNL     1      -2.364  -0.344  -0.307  1.00  0.00           C  
HETATM    6  O1  UNL     1      -3.761  -0.644  -0.148  1.00  0.00           O  
HETATM    7  C6  UNL     1      -4.192  -0.887   1.141  1.00  0.00           C  
HETATM    8  C7  UNL     1      -5.640  -1.200   1.332  1.00  0.00           C  
HETATM    9  O2  UNL     1      -3.431  -0.855   2.142  1.00  0.00           O  
HETATM   10  C8  UNL     1      -1.597  -1.373  -0.507  1.00  0.00           C  
HETATM   11  C9  UNL     1      -2.298  -2.739  -0.541  1.00  0.00           C  
HETATM   12  C10 UNL     1      -0.149  -1.461  -0.712  1.00  0.00           C  
HETATM   13  C11 UNL     1       0.709  -0.729   0.280  1.00  0.00           C  
HETATM   14  C12 UNL     1       1.981  -0.265  -0.386  1.00  0.00           C  
HETATM   15  C13 UNL     1       3.194  -0.389   0.489  1.00  0.00           C  
HETATM   16  C14 UNL     1       4.387   0.111  -0.306  1.00  0.00           C  
HETATM   17  C15 UNL     1       3.421  -1.860   0.766  1.00  0.00           C  
HETATM   18  O3  UNL     1       3.159   0.264   1.681  1.00  0.00           O  
HETATM   19  C16 UNL     1       1.853   1.023  -1.123  1.00  0.00           C  
HETATM   20  C17 UNL     1       1.292   2.174  -0.425  1.00  0.00           C  
HETATM   21  O4  UNL     1       1.516   2.176   0.972  1.00  0.00           O  
HETATM   22  H1  UNL     1      -1.624   3.933  -0.172  1.00  0.00           H  
HETATM   23  H2  UNL     1       0.117   4.281   0.421  1.00  0.00           H  
HETATM   24  H3  UNL     1      -0.749   0.905  -1.993  1.00  0.00           H  
HETATM   25  H4  UNL     1      -1.696   2.368  -1.954  1.00  0.00           H  
HETATM   26  H5  UNL     1      -3.014   1.699  -0.303  1.00  0.00           H  
HETATM   27  H6  UNL     1      -1.730   1.409   0.827  1.00  0.00           H  
HETATM   28  H7  UNL     1      -5.986  -0.823   2.308  1.00  0.00           H  
HETATM   29  H8  UNL     1      -5.800  -2.311   1.330  1.00  0.00           H  
HETATM   30  H9  UNL     1      -6.269  -0.762   0.557  1.00  0.00           H  
HETATM   31  H10 UNL     1      -3.333  -2.624  -0.890  1.00  0.00           H  
HETATM   32  H11 UNL     1      -2.279  -3.124   0.500  1.00  0.00           H  
HETATM   33  H12 UNL     1      -1.791  -3.407  -1.259  1.00  0.00           H  
HETATM   34  H13 UNL     1       0.211  -2.540  -0.645  1.00  0.00           H  
HETATM   35  H14 UNL     1       0.205  -1.180  -1.730  1.00  0.00           H  
HETATM   36  H15 UNL     1       1.044  -1.427   1.105  1.00  0.00           H  
HETATM   37  H16 UNL     1       0.143   0.043   0.763  1.00  0.00           H  
HETATM   38  H17 UNL     1       2.166  -1.043  -1.198  1.00  0.00           H  
HETATM   39  H18 UNL     1       5.292  -0.304   0.203  1.00  0.00           H  
HETATM   40  H19 UNL     1       4.341  -0.174  -1.370  1.00  0.00           H  
HETATM   41  H20 UNL     1       4.485   1.215  -0.224  1.00  0.00           H  
HETATM   42  H21 UNL     1       2.950  -2.510   0.001  1.00  0.00           H  
HETATM   43  H22 UNL     1       3.008  -2.095   1.763  1.00  0.00           H  
HETATM   44  H23 UNL     1       4.517  -2.019   0.837  1.00  0.00           H  
HETATM   45  H24 UNL     1       4.069   0.398   2.010  1.00  0.00           H  
HETATM   46  H25 UNL     1       2.895   1.259  -1.501  1.00  0.00           H  
HETATM   47  H26 UNL     1       1.284   0.836  -2.083  1.00  0.00           H  
HETATM   48  H27 UNL     1       1.846   3.104  -0.763  1.00  0.00           H  
HETATM   49  H28 UNL     1       1.512   3.084   1.316  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   48
CONECT   21   49
END

HMDB0035075
     RDKit          3D
Tanacetol B
 49 49  0  0  0  0  0  0  0  0999 V2000
   -0.5827    3.6187   -0.0962 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1296    2.4749   -0.6005 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1361    1.6281   -1.2882 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0471    1.0855   -0.2146 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3643   -0.3443   -0.3070 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7611   -0.6439   -0.1479 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1919   -0.8866    1.1407 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6399   -1.2003    1.3320 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4305   -0.8552    2.1415 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5974   -1.3733   -0.5065 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2982   -2.7391   -0.5415 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1486   -1.4610   -0.7122 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7087   -0.7291    0.2802 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9814   -0.2653   -0.3864 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1942   -0.3893    0.4887 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3874    0.1110   -0.3057 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4209   -1.8601    0.7659 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1588    0.2637    1.6806 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8528    1.0227   -1.1228 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2916    2.1739   -0.4253 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5161    2.1765    0.9719 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6236    3.9328   -0.1724 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1169    4.2815    0.4214 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7494    0.9052   -1.9933 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6956    2.3684   -1.9536 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0136    1.6992   -0.3028 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7296    1.4086    0.8269 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9860   -0.8230    2.3078 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8002   -2.3112    1.3297 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2689   -0.7618    0.5573 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3331   -2.6243   -0.8901 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2791   -3.1237    0.4995 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7908   -3.4072   -1.2594 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2113   -2.5402   -0.6449 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2049   -1.1801   -1.7305 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0441   -1.4268    1.1051 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1429    0.0433    0.7625 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1656   -1.0431   -1.1982 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2917   -0.3036    0.2027 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3407   -0.1740   -1.3702 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4851    1.2149   -0.2241 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9500   -2.5100    0.0011 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0081   -2.0948    1.7634 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5171   -2.0188    0.8366 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0692    0.3977    2.0102 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8950    1.2588   -1.5005 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2842    0.8361   -2.0830 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8464    3.1044   -0.7634 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5121    3.0840    1.3155 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  1  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
 20 48  1  0
 21 49  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Tanacetol	HMDB
Tanecetol b	HMDB
(1E)-7-Hydroxy-5-(2-hydroxypropan-2-yl)-2-methyl-8-methylidenecyclodec-1-en-1-yl acetic acid	Generator

Chemical Formula

C₁₇H₂₈O₄

Average Molecular Weight

296.4018

Monoisotopic Molecular Weight

296.198759384

IUPAC Name

(1E)-7-hydroxy-5-(2-hydroxypropan-2-yl)-2-methyl-8-methylidenecyclodec-1-en-1-yl acetate

Traditional Name

(1E)-7-hydroxy-5-(2-hydroxypropan-2-yl)-2-methyl-8-methylidenecyclodec-1-en-1-yl acetate

CAS Registry Number

86787-28-2

SMILES

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

InChI Identifier

InChI=1S/C17H28O4/c1-11-7-9-16(21-13(3)18)12(2)6-8-14(10-15(11)19)17(4,5)20/h14-15,19-20H,1,6-10H2,2-5H3/b16-12+

InChI Key

QZYCUDRAMHSVOE-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
Secondary alcohol
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

Not Available

Urine (PMID: 20971021)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	163 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	4.55 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	0.38 g/L	ALOGPS
logP	2.26	ALOGPS
logP	1.75	ChemAxon
logS	-2.9	ALOGPS
pKa (Strongest Acidic)	14.49	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	66.76 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	83.91 m³·mol⁻¹	ChemAxon
Polarizability	33.43 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]+	171.024	31661259
DarkChem	[M-H]-	165.744	31661259
DeepCCS	[M+H]+	173.275	30932474
DeepCCS	[M-H]-	170.917	30932474
DeepCCS	[M-2H]-	204.765	30932474
DeepCCS	[M+Na]+	179.992	30932474
AllCCS	[M+H]+	173.9	32859911
AllCCS	[M+H-H2O]+	170.7	32859911
AllCCS	[M+NH4]+	176.8	32859911
AllCCS	[M+Na]+	177.7	32859911
AllCCS	[M-H]-	175.8	32859911
AllCCS	[M+Na-2H]-	176.6	32859911
AllCCS	[M+HCOO]-	177.5	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Tanacetol B	CC(=O)O\C1=C(C)\CCC(CC(O)C(=C)CC1)C(C)(C)O	3019.6	Standard polar	33892256
Tanacetol B	CC(=O)O\C1=C(C)\CCC(CC(O)C(=C)CC1)C(C)(C)O	2068.6	Standard non polar	33892256
Tanacetol B	CC(=O)O\C1=C(C)\CCC(CC(O)C(=C)CC1)C(C)(C)O	2129.5	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Tanacetol B,1TMS,isomer #1	C=C1CC/C(OC(C)=O)=C(/C)CCC(C(C)(C)O)CC1O[Si](C)(C)C	2203.2	Semi standard non polar	33892256
Tanacetol B,1TMS,isomer #2	C=C1CC/C(OC(C)=O)=C(/C)CCC(C(C)(C)O[Si](C)(C)C)CC1O	2219.2	Semi standard non polar	33892256
Tanacetol B,2TMS,isomer #1	C=C1CC/C(OC(C)=O)=C(/C)CCC(C(C)(C)O[Si](C)(C)C)CC1O[Si](C)(C)C	2273.5	Semi standard non polar	33892256
Tanacetol B,1TBDMS,isomer #1	C=C1CC/C(OC(C)=O)=C(/C)CCC(C(C)(C)O)CC1O[Si](C)(C)C(C)(C)C	2406.4	Semi standard non polar	33892256
Tanacetol B,1TBDMS,isomer #2	C=C1CC/C(OC(C)=O)=C(/C)CCC(C(C)(C)O[Si](C)(C)C(C)(C)C)CC1O	2450.6	Semi standard non polar	33892256
Tanacetol B,2TBDMS,isomer #1	C=C1CC/C(OC(C)=O)=C(/C)CCC(C(C)(C)O[Si](C)(C)C(C)(C)C)CC1O[Si](C)(C)C(C)(C)C	2683.7	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 - Tanacetol B GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4i-9070000000-551c77fd6c2905ba32ff	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Tanacetol B GC-MS (2 TMS) - 70eV, Positive	splash10-003r-9716300000-7c16fbfed5ae335b28e0	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Tanacetol B 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 B 10V, Positive-QTOF	splash10-004j-0090000000-aeede0fc5bcc716f9c31	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tanacetol B 20V, Positive-QTOF	splash10-00n0-0190000000-5411c8eb71528d22146e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tanacetol B 40V, Positive-QTOF	splash10-0zg0-9570000000-f21b9a12ea458675a6d0	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tanacetol B 10V, Negative-QTOF	splash10-0002-0090000000-1b8241d961fb6136c98d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tanacetol B 20V, Negative-QTOF	splash10-0f7a-2090000000-1a47e5b8ab34edc68e25	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tanacetol B 40V, Negative-QTOF	splash10-052o-9370000000-2b6e7a2b21714d0bcbce	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tanacetol B 10V, Negative-QTOF	splash10-0f72-1090000000-662ec1520ff787460b9d	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tanacetol B 20V, Negative-QTOF	splash10-0udi-3090000000-9f6f019b8d9efaee9667	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tanacetol B 40V, Negative-QTOF	splash10-0a4i-9000000000-4b2497b52c1b296bbd34	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tanacetol B 10V, Positive-QTOF	splash10-004j-0090000000-95cee505acf6e48a081e	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tanacetol B 20V, Positive-QTOF	splash10-052r-1090000000-7b9f9db31f372e08943f	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tanacetol B 40V, Positive-QTOF	splash10-00kr-3190000000-bedc3eb081b4624a4593	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

FDB013699

KNApSAcK ID

C00011703

Chemspider ID

35013838

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

131751660

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1847531

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 B (HMDB0035075)

MOL for HMDB0035075 (Tanacetol B)

3D MOL for HMDB0035075 (Tanacetol B)

3D SDF for HMDB0035075 (Tanacetol B)

3D-SDF for HMDB0035075 (Tanacetol B)

PDB for HMDB0035075 (Tanacetol B)

3D PDB for HMDB0035075 (Tanacetol B)

SMILES for HMDB0035075 (Tanacetol B)

INCHI for HMDB0035075 (Tanacetol B)

Structure for HMDB0035075 (Tanacetol B)

3D Structure for HMDB0035075 (Tanacetol B)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra