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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 21:56:52 UTC

Update Date

2022-03-07 02:55:03 UTC

HMDB ID

HMDB0036773

Secondary Accession Numbers

HMDB36773

Metabolite Identification

Common Name

Tavulin

Description

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

Structure

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

HMDB0036773
     RDKit          3D
Tavulin
 39 40  0  0  0  0  0  0  0  0999 V2000
    4.0201   -1.0779    0.5292 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1714   -0.0999    0.3330 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1764    1.1728    1.0466 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9885    1.5219    1.9704 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1383    1.9726    0.5601 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1664    1.0200    0.0921 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1849    1.6845   -0.8009 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1136    1.7803   -0.5593 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9761    2.4901   -1.5724 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8066    1.2447    0.6325 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7481    2.1982    1.0572 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5718   -0.0199    0.2822 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6517   -0.9313   -0.5495 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7598   -1.6692    0.3807 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4462   -2.2701    1.5785 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5497   -1.8130    0.2076 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3736   -1.3007   -0.8887 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7285   -1.2261   -2.1182 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0248    0.0194   -0.6022 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9507   -1.9992   -0.0449 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8257   -1.0476    1.2496 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7404    0.5642    0.9832 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6195    2.1144   -1.7209 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4467    3.3895   -1.9711 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9049    2.8452   -1.1201 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1116    1.7820   -2.4112 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1735    1.0246    1.4896 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7094    2.3531    2.0238 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4613    0.2564   -0.3135 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8157   -0.5244    1.2333 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3472   -1.6358   -1.0587 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1571   -0.2993   -1.2777 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9170   -3.1732    1.9362 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4399   -2.6093    1.2365 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5584   -1.5867    2.4132 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1115   -2.3884    0.9819 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1960   -2.0679   -1.0767 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7293   -2.1258   -2.5754 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4208    0.4317   -1.5558 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  2  0
 16 17  1  0
 17 18  1  0
 17 19  1  0
 19  2  1  0
 19  6  1  0
  1 20  1  0
  1 21  1  0
  6 22  1  0
  7 23  1  0
  9 24  1  0
  9 25  1  0
  9 26  1  0
 10 27  1  0
 11 28  1  0
 12 29  1  0
 12 30  1  0
 13 31  1  0
 13 32  1  0
 15 33  1  0
 15 34  1  0
 15 35  1  0
 16 36  1  0
 17 37  1  0
 18 38  1  0
 19 39  1  0
M  END

  Mrv0541 05061309192D          

 19 20  0  0  0  0            999 V2000
    1.2890    1.4129    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3328    3.2521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8808    0.3310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9012    1.3375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1925    2.1093    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7958    0.4320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5643    1.8420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0871    1.2038    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8556    2.6139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3652    0.9751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6697    2.7476    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9817    0.2983    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7502    1.7084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4589    0.9365    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5832    1.7707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9610    3.5194    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6904   -0.4735    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3551    2.0620    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1061    2.2240    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  4  1  0  0  0  0
  8  1  1  0  0  0  0
  8  4  1  0  0  0  0
  8  6  2  0  0  0  0
  9  2  1  0  0  0  0
  9  7  2  0  0  0  0
 10  3  2  0  0  0  0
 11  5  1  0  0  0  0
 11  9  1  0  0  0  0
 12  6  1  0  0  0  0
 13  7  1  0  0  0  0
 14 10  1  0  0  0  0
 14 12  1  0  0  0  0
 14 13  1  0  0  0  0
 15 10  1  0  0  0  0
 16 11  1  0  0  0  0
 17 12  1  0  0  0  0
 18 15  2  0  0  0  0
 19 13  1  0  0  0  0
 19 15  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0036773

> <DATABASE_NAME>
hmdb

> <SMILES>
C\C1=C/C(O)C2C(OC(=O)C2=C)\C=C(C)\C(O)CC1

> <INCHI_IDENTIFIER>
InChI=1S/C15H20O4/c1-8-4-5-11(16)9(2)7-13-14(12(17)6-8)10(3)15(18)19-13/h6-7,11-14,16-17H,3-5H2,1-2H3/b8-6+,9-7+

> <INCHI_KEY>
YMNZWKHEJQGPIA-CDJQDVQCSA-N

> <FORMULA>
C15H20O4

> <MOLECULAR_WEIGHT>
264.3169

> <EXACT_MASS>
264.136159128

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
27.6651825772664

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4,9-dihydroxy-6,10-dimethyl-3-methylidene-2H,3H,3aH,4H,7H,8H,9H,11aH-cyclodeca[b]furan-2-one

> <ALOGPS_LOGP>
0.98

> <JCHEM_LOGP>
1.3961012396666665

> <ALOGPS_LOGS>
-1.85

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.594135220632694

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.070206921271711

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9722475352027846

> <JCHEM_POLAR_SURFACE_AREA>
66.76

> <JCHEM_REFRACTIVITY>
72.87859999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.70e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4,9-dihydroxy-6,10-dimethyl-3-methylidene-3aH,4H,7H,8H,9H,11aH-cyclodeca[b]furan-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0036773
     RDKit          3D
Tavulin
 39 40  0  0  0  0  0  0  0  0999 V2000
    4.0201   -1.0779    0.5292 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1714   -0.0999    0.3330 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1764    1.1728    1.0466 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9885    1.5219    1.9704 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1383    1.9726    0.5601 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1664    1.0200    0.0921 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1849    1.6845   -0.8009 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1136    1.7803   -0.5593 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9761    2.4901   -1.5724 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8066    1.2447    0.6325 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7481    2.1982    1.0572 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5718   -0.0199    0.2822 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6517   -0.9313   -0.5495 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7598   -1.6692    0.3807 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4462   -2.2701    1.5785 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5497   -1.8130    0.2076 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3736   -1.3007   -0.8887 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7285   -1.2261   -2.1182 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0248    0.0194   -0.6022 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9507   -1.9992   -0.0449 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8257   -1.0476    1.2496 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7404    0.5642    0.9832 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6195    2.1144   -1.7209 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4467    3.3895   -1.9711 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9049    2.8452   -1.1201 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1116    1.7820   -2.4112 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1735    1.0246    1.4896 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7094    2.3531    2.0238 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4613    0.2564   -0.3135 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8157   -0.5244    1.2333 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3472   -1.6358   -1.0587 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1571   -0.2993   -1.2777 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9170   -3.1732    1.9362 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4399   -2.6093    1.2365 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5584   -1.5867    2.4132 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1115   -2.3884    0.9819 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1960   -2.0679   -1.0767 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7293   -2.1258   -2.5754 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4208    0.4317   -1.5558 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  2  0
 16 17  1  0
 17 18  1  0
 17 19  1  0
 19  2  1  0
 19  6  1  0
  1 20  1  0
  1 21  1  0
  6 22  1  0
  7 23  1  0
  9 24  1  0
  9 25  1  0
  9 26  1  0
 10 27  1  0
 11 28  1  0
 12 29  1  0
 12 30  1  0
 13 31  1  0
 13 32  1  0
 15 33  1  0
 15 34  1  0
 15 35  1  0
 16 36  1  0
 17 37  1  0
 18 38  1  0
 19 39  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       2.406   2.637   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.488   6.071   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.644   0.618   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.416   2.497   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.959   3.937   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.352   0.806   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.920   3.438   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.896   2.247   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.464   4.879   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.682   1.820   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.983   5.129   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.833   0.557   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.400   3.189   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.857   1.748   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -1.089   3.305   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       5.527   6.570   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       1.289  -0.884   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      -2.530   3.849   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       0.198   4.151   0.000  0.00  0.00           O+0
CONECT    1    8                                                            
CONECT    2    9                                                            
CONECT    3   10                                                            
CONECT    4    5    8                                                       
CONECT    5    4   11                                                       
CONECT    6    8   12                                                       
CONECT    7    9   13                                                       
CONECT    8    1    4    6                                                  
CONECT    9    2    7   11                                                  
CONECT   10    3   14   15                                                  
CONECT   11    5    9   16                                                  
CONECT   12    6   14   17                                                  
CONECT   13    7   14   19                                                  
CONECT   14   10   12   13                                                  
CONECT   15   10   18   19                                                  
CONECT   16   11                                                            
CONECT   17   12                                                            
CONECT   18   15                                                            
CONECT   19   13   15                                                       
MASTER        0    0    0    0    0    0    0    0   19    0   40    0
END

COMPND    HMDB0036773
HETATM    1  C1  UNL     1       4.020  -1.078   0.529  1.00  0.00           C  
HETATM    2  C2  UNL     1       3.171  -0.100   0.333  1.00  0.00           C  
HETATM    3  C3  UNL     1       3.176   1.173   1.047  1.00  0.00           C  
HETATM    4  O1  UNL     1       3.989   1.522   1.970  1.00  0.00           O  
HETATM    5  O2  UNL     1       2.138   1.973   0.560  1.00  0.00           O  
HETATM    6  C4  UNL     1       1.166   1.020   0.092  1.00  0.00           C  
HETATM    7  C5  UNL     1       0.185   1.684  -0.801  1.00  0.00           C  
HETATM    8  C6  UNL     1      -1.114   1.780  -0.559  1.00  0.00           C  
HETATM    9  C7  UNL     1      -1.976   2.490  -1.572  1.00  0.00           C  
HETATM   10  C8  UNL     1      -1.807   1.245   0.633  1.00  0.00           C  
HETATM   11  O3  UNL     1      -2.748   2.198   1.057  1.00  0.00           O  
HETATM   12  C9  UNL     1      -2.572  -0.020   0.282  1.00  0.00           C  
HETATM   13  C10 UNL     1      -1.652  -0.931  -0.549  1.00  0.00           C  
HETATM   14  C11 UNL     1      -0.760  -1.669   0.381  1.00  0.00           C  
HETATM   15  C12 UNL     1      -1.446  -2.270   1.578  1.00  0.00           C  
HETATM   16  C13 UNL     1       0.550  -1.813   0.208  1.00  0.00           C  
HETATM   17  C14 UNL     1       1.374  -1.301  -0.889  1.00  0.00           C  
HETATM   18  O4  UNL     1       0.729  -1.226  -2.118  1.00  0.00           O  
HETATM   19  C15 UNL     1       2.025   0.019  -0.602  1.00  0.00           C  
HETATM   20  H1  UNL     1       3.951  -1.999  -0.045  1.00  0.00           H  
HETATM   21  H2  UNL     1       4.826  -1.048   1.250  1.00  0.00           H  
HETATM   22  H3  UNL     1       0.740   0.564   0.983  1.00  0.00           H  
HETATM   23  H4  UNL     1       0.619   2.114  -1.721  1.00  0.00           H  
HETATM   24  H5  UNL     1      -1.447   3.390  -1.971  1.00  0.00           H  
HETATM   25  H6  UNL     1      -2.905   2.845  -1.120  1.00  0.00           H  
HETATM   26  H7  UNL     1      -2.112   1.782  -2.411  1.00  0.00           H  
HETATM   27  H8  UNL     1      -1.174   1.025   1.490  1.00  0.00           H  
HETATM   28  H9  UNL     1      -2.709   2.353   2.024  1.00  0.00           H  
HETATM   29  H10 UNL     1      -3.461   0.256  -0.314  1.00  0.00           H  
HETATM   30  H11 UNL     1      -2.816  -0.524   1.233  1.00  0.00           H  
HETATM   31  H12 UNL     1      -2.347  -1.636  -1.059  1.00  0.00           H  
HETATM   32  H13 UNL     1      -1.157  -0.299  -1.278  1.00  0.00           H  
HETATM   33  H14 UNL     1      -0.917  -3.173   1.936  1.00  0.00           H  
HETATM   34  H15 UNL     1      -2.440  -2.609   1.236  1.00  0.00           H  
HETATM   35  H16 UNL     1      -1.558  -1.587   2.413  1.00  0.00           H  
HETATM   36  H17 UNL     1       1.112  -2.388   0.982  1.00  0.00           H  
HETATM   37  H18 UNL     1       2.196  -2.068  -1.077  1.00  0.00           H  
HETATM   38  H19 UNL     1       0.729  -2.126  -2.575  1.00  0.00           H  
HETATM   39  H20 UNL     1       2.421   0.432  -1.556  1.00  0.00           H  
CONECT    1    2    2   20   21
CONECT    2    3   19
CONECT    3    4    4    5
CONECT    5    6
CONECT    6    7   19   22
CONECT    7    8    8   23
CONECT    8    9   10
CONECT    9   24   25   26
CONECT   10   11   12   27
CONECT   11   28
CONECT   12   13   29   30
CONECT   13   14   31   32
CONECT   14   15   16   16
CONECT   15   33   34   35
CONECT   16   17   36
CONECT   17   18   19   37
CONECT   18   38
CONECT   19   39
END

HMDB0036773
     RDKit          3D
Tavulin
 39 40  0  0  0  0  0  0  0  0999 V2000
    4.0201   -1.0779    0.5292 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1714   -0.0999    0.3330 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1764    1.1728    1.0466 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9885    1.5219    1.9704 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1383    1.9726    0.5601 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1664    1.0200    0.0921 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1849    1.6845   -0.8009 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1136    1.7803   -0.5593 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9761    2.4901   -1.5724 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8066    1.2447    0.6325 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7481    2.1982    1.0572 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5718   -0.0199    0.2822 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6517   -0.9313   -0.5495 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7598   -1.6692    0.3807 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4462   -2.2701    1.5785 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5497   -1.8130    0.2076 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3736   -1.3007   -0.8887 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7285   -1.2261   -2.1182 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0248    0.0194   -0.6022 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9507   -1.9992   -0.0449 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8257   -1.0476    1.2496 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7404    0.5642    0.9832 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6195    2.1144   -1.7209 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4467    3.3895   -1.9711 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9049    2.8452   -1.1201 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1116    1.7820   -2.4112 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1735    1.0246    1.4896 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7094    2.3531    2.0238 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4613    0.2564   -0.3135 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8157   -0.5244    1.2333 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3472   -1.6358   -1.0587 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1571   -0.2993   -1.2777 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9170   -3.1732    1.9362 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4399   -2.6093    1.2365 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5584   -1.5867    2.4132 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1115   -2.3884    0.9819 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1960   -2.0679   -1.0767 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7293   -2.1258   -2.5754 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4208    0.4317   -1.5558 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  2  0
 16 17  1  0
 17 18  1  0
 17 19  1  0
 19  2  1  0
 19  6  1  0
  1 20  1  0
  1 21  1  0
  6 22  1  0
  7 23  1  0
  9 24  1  0
  9 25  1  0
  9 26  1  0
 10 27  1  0
 11 28  1  0
 12 29  1  0
 12 30  1  0
 13 31  1  0
 13 32  1  0
 15 33  1  0
 15 34  1  0
 15 35  1  0
 16 36  1  0
 17 37  1  0
 18 38  1  0
 19 39  1  0
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
Tabulin	HMDB
Tatridin a	HMDB

Chemical Formula

C₁₅H₂₀O₄

Average Molecular Weight

264.3169

Monoisotopic Molecular Weight

264.136159128

IUPAC Name

4,9-dihydroxy-6,10-dimethyl-3-methylidene-2H,3H,3aH,4H,7H,8H,9H,11aH-cyclodeca[b]furan-2-one

Traditional Name

4,9-dihydroxy-6,10-dimethyl-3-methylidene-3aH,4H,7H,8H,9H,11aH-cyclodeca[b]furan-2-one

CAS Registry Number

71030-09-6

SMILES

C\C1=C/C(O)C2C(OC(=O)C2=C)\C=C(C)\C(O)CC1

InChI Identifier

InChI=1S/C15H20O4/c1-8-4-5-11(16)9(2)7-13-14(12(17)6-8)10(3)15(18)19-13/h6-7,11-14,16-17H,3-5H2,1-2H3/b8-6+,9-7+

InChI Key

YMNZWKHEJQGPIA-CDJQDVQCSA-N

Chemical Taxonomy

Description

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

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Germacranolides and derivatives

Alternative Parents

Substituents

Germacranolide
Germacrane sesquiterpenoid
Sesquiterpenoid
Gamma butyrolactone
Tetrahydrofuran
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Secondary alcohol
Lactone
Carboxylic acid ester
Oxacycle
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organoheterocyclic compound
Alcohol
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Carbonyl group
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Route of exposure

Enteral

Ingestion (HMDB: HMDB0036773)

Source

Endogenous

Endogenous (HMDB: HMDB0036773)

Plant

Plant (HMDB: HMDB0036773)

Animal

Animal (HMDB: HMDB0036773)

Exogenous

Food

Food (HMDB: HMDB0036773)

Herb and spice

Herbs and Spices (FooDB: FOOD00866)

Exogenous (HMDB: HMDB0036773)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0036773)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0036773)

Lipid metabolism pathway (HMDB: HMDB0036773)

Cellular process

Cell signaling (HMDB: HMDB0036773)

Biochemical process

Lipid transport (HMDB: HMDB0036773)

Role

Biological role

Energy source (HMDB: HMDB0036773)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0036773)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	160 - 161 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	3.7 g/L	ALOGPS
logP	0.98	ALOGPS
logP	1.4	ChemAxon
logS	-1.8	ALOGPS
pKa (Strongest Acidic)	6.07	ChemAxon
pKa (Strongest Basic)	-3	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	0	ChemAxon
Refractivity	72.88 m³·mol⁻¹	ChemAxon
Polarizability	27.67 Å³	ChemAxon
Number of Rings	2	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]+	164.807	31661259
DarkChem	[M-H]-	156.58	31661259
DeepCCS	[M+H]+	172.176	30932474
DeepCCS	[M-H]-	169.818	30932474
DeepCCS	[M-2H]-	202.704	30932474
DeepCCS	[M+Na]+	178.269	30932474
AllCCS	[M+H]+	163.3	32859911
AllCCS	[M+H-H2O]+	159.6	32859911
AllCCS	[M+NH4]+	166.8	32859911
AllCCS	[M+Na]+	167.7	32859911
AllCCS	[M-H]-	164.9	32859911
AllCCS	[M+Na-2H]-	165.0	32859911
AllCCS	[M+HCOO]-	165.3	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Tavulin	C\C1=C/C(O)C2C(OC(=O)C2=C)\C=C(C)\C(O)CC1	3250.0	Standard polar	33892256
Tavulin	C\C1=C/C(O)C2C(OC(=O)C2=C)\C=C(C)\C(O)CC1	2230.5	Standard non polar	33892256
Tavulin	C\C1=C/C(O)C2C(OC(=O)C2=C)\C=C(C)\C(O)CC1	2389.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Tavulin,1TMS,isomer #1	C=C1C(=O)OC2/C=C(\C)C(O)CC/C(C)=C/C(O[Si](C)(C)C)C12	2315.8	Semi standard non polar	33892256
Tavulin,1TMS,isomer #2	C=C1C(=O)OC2/C=C(\C)C(O[Si](C)(C)C)CC/C(C)=C/C(O)C12	2311.9	Semi standard non polar	33892256
Tavulin,2TMS,isomer #1	C=C1C(=O)OC2/C=C(\C)C(O[Si](C)(C)C)CC/C(C)=C/C(O[Si](C)(C)C)C12	2328.3	Semi standard non polar	33892256
Tavulin,1TBDMS,isomer #1	C=C1C(=O)OC2/C=C(\C)C(O)CC/C(C)=C/C(O[Si](C)(C)C(C)(C)C)C12	2536.5	Semi standard non polar	33892256
Tavulin,1TBDMS,isomer #2	C=C1C(=O)OC2/C=C(\C)C(O[Si](C)(C)C(C)(C)C)CC/C(C)=C/C(O)C12	2523.5	Semi standard non polar	33892256
Tavulin,2TBDMS,isomer #1	C=C1C(=O)OC2/C=C(\C)C(O[Si](C)(C)C(C)(C)C)CC/C(C)=C/C(O[Si](C)(C)C(C)(C)C)C12	2754.1	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 - Tavulin GC-MS (Non-derivatized) - 70eV, Positive	splash10-0fb9-9380000000-448647b9dbb892e9f2e6	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Tavulin GC-MS (2 TMS) - 70eV, Positive	splash10-00bc-8009000000-a7ea6e8c1f4d6814ca95	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Tavulin GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Tavulin 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 - Tavulin 10V, Positive-QTOF	splash10-00kb-0190000000-7b5074e123efc5f507f6	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tavulin 20V, Positive-QTOF	splash10-004j-0590000000-9da50f35ad323dcfee9b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tavulin 40V, Positive-QTOF	splash10-0fvl-9730000000-385cfb57b0f85dcc2fd1	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tavulin 10V, Negative-QTOF	splash10-03di-0090000000-0dee158665e3b69633e4	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tavulin 20V, Negative-QTOF	splash10-0292-0090000000-939f3116c3dfcff2e1ab	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tavulin 40V, Negative-QTOF	splash10-014r-9420000000-1867dead4c303d96174a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tavulin 10V, Positive-QTOF	splash10-00kb-0090000000-2b27f926600170cc11ef	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tavulin 20V, Positive-QTOF	splash10-004j-0090000000-e3da8bf4aa425f6cccf5	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tavulin 40V, Positive-QTOF	splash10-004i-0290000000-75c3dd05035115c932ce	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tavulin 10V, Negative-QTOF	splash10-03di-0090000000-7dcdfe4b0d677baa733e	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tavulin 20V, Negative-QTOF	splash10-01ot-0090000000-b5ed35e47169ab559389	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tavulin 40V, Negative-QTOF	splash10-004l-0490000000-cfe622fab0199b9153d1	2021-09-22	Wishart Lab	View Spectrum

NMR Spectra

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

FDB015715

KNApSAcK ID

C00011801

Chemspider ID

35014243

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

14466150

PDB ID

Not Available

ChEBI ID

174480

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
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Showing metabocard for Tavulin (HMDB0036773)

MOL for HMDB0036773 (Tavulin)

3D MOL for HMDB0036773 (Tavulin)

3D SDF for HMDB0036773 (Tavulin)

3D-SDF for HMDB0036773 (Tavulin)

PDB for HMDB0036773 (Tavulin)

3D PDB for HMDB0036773 (Tavulin)

SMILES for HMDB0036773 (Tavulin)

INCHI for HMDB0036773 (Tavulin)

Structure for HMDB0036773 (Tavulin)

3D Structure for HMDB0036773 (Tavulin)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra