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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2021-09-24 02:51:41 UTC

Update Date

2021-09-24 02:51:41 UTC

HMDB ID

HMDB0303566

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Tulipinolide

Description

Tulipinolide belongs to germacranolides and derivatives class of compounds. Those 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. Tulipinolide is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Tulipinolide can be found in sweet bay, which makes tulipinolide a potential biomarker for the consumption of this food product.

Structure

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

HMDB0303566
     RDKit          3D
Tulipinolide
 43 44  0  0  0  0  0  0  0  0999 V2000
   -2.5558   -0.3150   -2.4071 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7808   -1.0892   -1.6942 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4111   -2.4773   -2.0586 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1557   -3.2206   -2.7607 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1920   -2.7162   -1.5001 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2393   -1.5520   -0.7110 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9939   -2.0958    0.4133 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0913   -1.7314    1.0133 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5774   -2.5919    2.1935 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9843   -0.5777    0.7701 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0695   -0.0055   -0.5690 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2885    1.2106   -0.8893 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1568    1.6577   -0.4481 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6993    2.9930   -1.0657 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2135    1.1215    0.5492 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0711    0.5379   -0.0246 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0709    0.6595    1.0225 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1246    1.5438    0.9310 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1570    1.6541    2.0206 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2621    2.2821   -0.0525 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0645   -0.8737   -0.3855 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9699   -0.6854   -3.3292 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8251    0.6878   -2.1546 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7419   -0.9800   -1.4695 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5372   -3.0295    0.8701 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6526   -2.7407    2.1386 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3208   -1.9969    3.0913 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0373   -3.5376    2.2171 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0342   -1.0025    0.9997 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9214    0.2220    1.5416 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0452   -0.7841   -1.3749 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1702    0.3408   -0.6724 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8236    1.8211   -1.6808 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2024    3.6006   -0.2772 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5519    3.5637   -1.4231 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0596    2.7496   -1.8357 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6268    0.5546    1.3869 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1981    2.0339    1.1427 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4087    1.2199   -0.8243 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7186    2.3237    2.7890 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3262    0.6447    2.4674 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0765    2.1104    1.6605 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5510   -1.5302    0.3900 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 18 20  2  0
 16 21  1  0
 21  2  1  0
 21  6  1  0
  1 22  1  0
  1 23  1  0
  6 24  1  0
  7 25  1  0
  9 26  1  0
  9 27  1  0
  9 28  1  0
 10 29  1  0
 10 30  1  0
 11 31  1  0
 11 32  1  0
 12 33  1  0
 14 34  1  0
 14 35  1  0
 14 36  1  0
 15 37  1  0
 15 38  1  0
 16 39  1  0
 19 40  1  0
 19 41  1  0
 19 42  1  0
 21 43  1  0
M  END


  Mrv0541 02241216422D          

 21 22  0  0  0  0            999 V2000
   -2.4994    1.2173    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4994    0.3915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7851   -0.0213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0721    0.3915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0721    1.2173    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7851    1.6288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3578   -0.0213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3550    0.3915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3550    1.2173    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3578    1.6288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1872   -0.8264    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6302   -0.9131    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9633   -0.1630    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4886    0.6338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7851   -0.8471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0707    1.6288    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0432   -1.6288    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7712    0.0061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7850    1.2160    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4994    1.6288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7850    0.3901    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  6  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3 15  1  0  0  0  0
  4  7  1  0  0  0  0
  5  6  2  0  0  0  0
  5 10  1  0  0  0  0
  5 14  1  0  0  0  0
  7  8  1  0  0  0  0
  7 11  1  0  0  0  0
  8  9  1  0  0  0  0
  8 13  1  0  0  0  0
  9 10  1  0  0  0  0
  9 16  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 17  2  0  0  0  0
 13 18  2  0  0  0  0
 16 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0303566

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(=O)OC1C\C(C)=C\CC\C(C)=C\C2OC(=O)C(=C)C12

> <INCHI_IDENTIFIER>
InChI=1S/C17H22O4/c1-10-6-5-7-11(2)9-15-16(12(3)17(19)21-15)14(8-10)20-13(4)18/h6,9,14-16H,3,5,7-8H2,1-2,4H3/b10-6+,11-9+

> <INCHI_KEY>
UPNVKIZABMRHNR-BBYAVRKXSA-N

> <FORMULA>
C17H22O4

> <MOLECULAR_WEIGHT>
290.3542

> <EXACT_MASS>
290.151809192

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
30.854303366874877

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
6,10-dimethyl-3-methylidene-2-oxo-2H,3H,3aH,4H,5H,8H,9H,11aH-cyclodeca[b]furan-4-yl acetate

> <ALOGPS_LOGP>
3.29

> <JCHEM_LOGP>
2.9121302570000003

> <ALOGPS_LOGS>
-3.54

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.197895542854455

> <JCHEM_PKA_STRONGEST_BASIC>
-6.637506960668167

> <JCHEM_POLAR_SURFACE_AREA>
52.6

> <JCHEM_REFRACTIVITY>
80.6686

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.47e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
6,10-dimethyl-3-methylidene-2-oxo-3aH,4H,5H,8H,9H,11aH-cyclodeca[b]furan-4-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0303566
     RDKit          3D
Tulipinolide
 43 44  0  0  0  0  0  0  0  0999 V2000
   -2.5558   -0.3150   -2.4071 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7808   -1.0892   -1.6942 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4111   -2.4773   -2.0586 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1557   -3.2206   -2.7607 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1920   -2.7162   -1.5001 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2393   -1.5520   -0.7110 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9939   -2.0958    0.4133 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0913   -1.7314    1.0133 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5774   -2.5919    2.1935 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9843   -0.5777    0.7701 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0695   -0.0055   -0.5690 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2885    1.2106   -0.8893 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1568    1.6577   -0.4481 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6993    2.9930   -1.0657 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2135    1.1215    0.5492 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0711    0.5379   -0.0246 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0709    0.6595    1.0225 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1246    1.5438    0.9310 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1570    1.6541    2.0206 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2621    2.2821   -0.0525 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0645   -0.8737   -0.3855 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9699   -0.6854   -3.3292 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8251    0.6878   -2.1546 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7419   -0.9800   -1.4695 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5372   -3.0295    0.8701 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6526   -2.7407    2.1386 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3208   -1.9969    3.0913 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0373   -3.5376    2.2171 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0342   -1.0025    0.9997 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9214    0.2220    1.5416 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0452   -0.7841   -1.3749 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1702    0.3408   -0.6724 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8236    1.8211   -1.6808 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2024    3.6006   -0.2772 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5519    3.5637   -1.4231 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0596    2.7496   -1.8357 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6268    0.5546    1.3869 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1981    2.0339    1.1427 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4087    1.2199   -0.8243 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7186    2.3237    2.7890 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3262    0.6447    2.4674 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0765    2.1104    1.6605 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5510   -1.5302    0.3900 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 18 20  2  0
 16 21  1  0
 21  2  1  0
 21  6  1  0
  1 22  1  0
  1 23  1  0
  6 24  1  0
  7 25  1  0
  9 26  1  0
  9 27  1  0
  9 28  1  0
 10 29  1  0
 10 30  1  0
 11 31  1  0
 11 32  1  0
 12 33  1  0
 14 34  1  0
 14 35  1  0
 14 36  1  0
 15 37  1  0
 15 38  1  0
 16 39  1  0
 19 40  1  0
 19 41  1  0
 19 42  1  0
 21 43  1  0
M  END

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      -4.666   2.272   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -4.666   0.731   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -3.332  -0.040   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.001   0.731   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.001   2.272   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -3.332   3.040   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.668  -0.040   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.663   0.731   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.663   2.272   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.668   3.040   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -0.349  -1.543   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       1.176  -1.704   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.798  -0.304   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.912   1.183   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -3.332  -1.581   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       1.999   3.040   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       1.947  -3.040   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       3.306   0.011   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.332   2.270   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.666   3.040   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       3.332   0.728   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4   15                                                  
CONECT    4    3    7                                                       
CONECT    5    6   10   14                                                  
CONECT    6    1    5                                                       
CONECT    7    4    8   11                                                  
CONECT    8    7    9   13                                                  
CONECT    9    8   10   16                                                  
CONECT   10    5    9                                                       
CONECT   11    7   12                                                       
CONECT   12   11   13   17                                                  
CONECT   13    8   12   18                                                  
CONECT   14    5                                                            
CONECT   15    3                                                            
CONECT   16    9   19                                                       
CONECT   17   12                                                            
CONECT   18   13                                                            
CONECT   19   16   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   44    0
END

COMPND    HMDB0303566
HETATM    1  C1  UNL     1      -2.556  -0.315  -2.407  1.00  0.00           C  
HETATM    2  C2  UNL     1      -1.781  -1.089  -1.694  1.00  0.00           C  
HETATM    3  C3  UNL     1      -1.411  -2.477  -2.059  1.00  0.00           C  
HETATM    4  O1  UNL     1      -2.156  -3.221  -2.761  1.00  0.00           O  
HETATM    5  O2  UNL     1      -0.192  -2.716  -1.500  1.00  0.00           O  
HETATM    6  C4  UNL     1       0.239  -1.552  -0.711  1.00  0.00           C  
HETATM    7  C5  UNL     1       0.994  -2.096   0.413  1.00  0.00           C  
HETATM    8  C6  UNL     1       2.091  -1.731   1.013  1.00  0.00           C  
HETATM    9  C7  UNL     1       2.577  -2.592   2.193  1.00  0.00           C  
HETATM   10  C8  UNL     1       2.984  -0.578   0.770  1.00  0.00           C  
HETATM   11  C9  UNL     1       3.069  -0.005  -0.569  1.00  0.00           C  
HETATM   12  C10 UNL     1       2.289   1.211  -0.889  1.00  0.00           C  
HETATM   13  C11 UNL     1       1.157   1.658  -0.448  1.00  0.00           C  
HETATM   14  C12 UNL     1       0.699   2.993  -1.066  1.00  0.00           C  
HETATM   15  C13 UNL     1       0.214   1.122   0.549  1.00  0.00           C  
HETATM   16  C14 UNL     1      -1.071   0.538  -0.025  1.00  0.00           C  
HETATM   17  O3  UNL     1      -2.071   0.660   1.022  1.00  0.00           O  
HETATM   18  C15 UNL     1      -3.125   1.544   0.931  1.00  0.00           C  
HETATM   19  C16 UNL     1      -4.157   1.654   2.021  1.00  0.00           C  
HETATM   20  O4  UNL     1      -3.262   2.282  -0.053  1.00  0.00           O  
HETATM   21  C17 UNL     1      -1.064  -0.874  -0.386  1.00  0.00           C  
HETATM   22  H1  UNL     1      -2.970  -0.685  -3.329  1.00  0.00           H  
HETATM   23  H2  UNL     1      -2.825   0.688  -2.155  1.00  0.00           H  
HETATM   24  H3  UNL     1       0.742  -0.980  -1.469  1.00  0.00           H  
HETATM   25  H4  UNL     1       0.537  -3.029   0.870  1.00  0.00           H  
HETATM   26  H5  UNL     1       3.653  -2.741   2.139  1.00  0.00           H  
HETATM   27  H6  UNL     1       2.321  -1.997   3.091  1.00  0.00           H  
HETATM   28  H7  UNL     1       2.037  -3.538   2.217  1.00  0.00           H  
HETATM   29  H8  UNL     1       4.034  -1.003   1.000  1.00  0.00           H  
HETATM   30  H9  UNL     1       2.921   0.222   1.542  1.00  0.00           H  
HETATM   31  H10 UNL     1       3.045  -0.784  -1.375  1.00  0.00           H  
HETATM   32  H11 UNL     1       4.170   0.341  -0.672  1.00  0.00           H  
HETATM   33  H12 UNL     1       2.824   1.821  -1.681  1.00  0.00           H  
HETATM   34  H13 UNL     1       0.202   3.601  -0.277  1.00  0.00           H  
HETATM   35  H14 UNL     1       1.552   3.564  -1.423  1.00  0.00           H  
HETATM   36  H15 UNL     1      -0.060   2.750  -1.836  1.00  0.00           H  
HETATM   37  H16 UNL     1       0.627   0.555   1.387  1.00  0.00           H  
HETATM   38  H17 UNL     1      -0.198   2.034   1.143  1.00  0.00           H  
HETATM   39  H18 UNL     1      -1.409   1.220  -0.824  1.00  0.00           H  
HETATM   40  H19 UNL     1      -3.719   2.324   2.789  1.00  0.00           H  
HETATM   41  H20 UNL     1      -4.326   0.645   2.467  1.00  0.00           H  
HETATM   42  H21 UNL     1      -5.076   2.110   1.661  1.00  0.00           H  
HETATM   43  H22 UNL     1      -1.551  -1.530   0.390  1.00  0.00           H  
CONECT    1    2    2   22   23
CONECT    2    3   21
CONECT    3    4    4    5
CONECT    5    6
CONECT    6    7   21   24
CONECT    7    8    8   25
CONECT    8    9   10
CONECT    9   26   27   28
CONECT   10   11   29   30
CONECT   11   12   31   32
CONECT   12   13   13   33
CONECT   13   14   15
CONECT   14   34   35   36
CONECT   15   16   37   38
CONECT   16   17   21   39
CONECT   17   18
CONECT   18   19   20   20
CONECT   19   40   41   42
CONECT   21   43
END

HMDB0303566
     RDKit          3D
Tulipinolide
 43 44  0  0  0  0  0  0  0  0999 V2000
   -2.5558   -0.3150   -2.4071 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7808   -1.0892   -1.6942 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4111   -2.4773   -2.0586 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1557   -3.2206   -2.7607 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1920   -2.7162   -1.5001 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2393   -1.5520   -0.7110 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9939   -2.0958    0.4133 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0913   -1.7314    1.0133 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5774   -2.5919    2.1935 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9843   -0.5777    0.7701 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0695   -0.0055   -0.5690 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2885    1.2106   -0.8893 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1568    1.6577   -0.4481 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6993    2.9930   -1.0657 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2135    1.1215    0.5492 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0711    0.5379   -0.0246 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0709    0.6595    1.0225 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1246    1.5438    0.9310 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1570    1.6541    2.0206 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2621    2.2821   -0.0525 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0645   -0.8737   -0.3855 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9699   -0.6854   -3.3292 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8251    0.6878   -2.1546 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7419   -0.9800   -1.4695 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5372   -3.0295    0.8701 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6526   -2.7407    2.1386 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3208   -1.9969    3.0913 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0373   -3.5376    2.2171 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0342   -1.0025    0.9997 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9214    0.2220    1.5416 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0452   -0.7841   -1.3749 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1702    0.3408   -0.6724 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8236    1.8211   -1.6808 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2024    3.6006   -0.2772 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5519    3.5637   -1.4231 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0596    2.7496   -1.8357 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6268    0.5546    1.3869 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1981    2.0339    1.1427 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4087    1.2199   -0.8243 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7186    2.3237    2.7890 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3262    0.6447    2.4674 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0765    2.1104    1.6605 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5510   -1.5302    0.3900 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 18 20  2  0
 16 21  1  0
 21  2  1  0
 21  6  1  0
  1 22  1  0
  1 23  1  0
  6 24  1  0
  7 25  1  0
  9 26  1  0
  9 27  1  0
  9 28  1  0
 10 29  1  0
 10 30  1  0
 11 31  1  0
 11 32  1  0
 12 33  1  0
 14 34  1  0
 14 35  1  0
 14 36  1  0
 15 37  1  0
 15 38  1  0
 16 39  1  0
 19 40  1  0
 19 41  1  0
 19 42  1  0
 21 43  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
6,10-Dimethyl-3-methylidene-2-oxo-2H,3H,3ah,4H,5H,8H,9H,11ah-cyclodeca[b]furan-4-yl acetic acid	Generator

Chemical Formula

C₁₇H₂₂O₄

Average Molecular Weight

290.3542

Monoisotopic Molecular Weight

290.151809192

IUPAC Name

6,10-dimethyl-3-methylidene-2-oxo-2H,3H,3aH,4H,5H,8H,9H,11aH-cyclodeca[b]furan-4-yl acetate

Traditional Name

6,10-dimethyl-3-methylidene-2-oxo-3aH,4H,5H,8H,9H,11aH-cyclodeca[b]furan-4-yl acetate

CAS Registry Number

Not Available

SMILES

CC(=O)OC1C\C(C)=C\CC\C(C)=C\C2OC(=O)C(=C)C12

InChI Identifier

InChI=1S/C17H22O4/c1-10-6-5-7-11(2)9-15-16(12(3)17(19)21-15)14(8-10)20-13(4)18/h6,9,14-16H,3,5,7-8H2,1-2,4H3/b10-6+,11-9+

InChI Key

UPNVKIZABMRHNR-BBYAVRKXSA-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
Dicarboxylic acid or derivatives
Gamma butyrolactone
Tetrahydrofuran
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Lactone
Carboxylic acid ester
Organoheterocyclic compound
Oxacycle
Carboxylic acid derivative
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Carbonyl group
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Sweet bay (FooDB: FOOD00097)

Process

Not Available

Role

Biological role

antitumor (HMDB: HMDB0303566)
cytotoxic (HMDB: HMDB0303566)

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	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
logP	3.29	ALOGPS
logP	2.91	ChemAxon
logS	-3.5	ALOGPS
pKa (Strongest Acidic)	6.2	ChemAxon
pKa (Strongest Basic)	-6.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	52.6 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	80.67 m³·mol⁻¹	ChemAxon
Polarizability	30.85 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
AllCCS	[M+H]+	169.879	32859911
AllCCS	[M+H-H2O]+	166.434	32859911
AllCCS	[M+Na]+	173.994	32859911
AllCCS	[M+NH4]+	173.075	32859911
AllCCS	[M-H]-	173.721	32859911
AllCCS	[M+Na-2H]-	173.821	32859911
AllCCS	[M+HCOO]-	174.056	32859911
DeepCCS	[M-2H]-	203.019	30932474
DeepCCS	[M+Na]+	178.246	30932474

Predicted Kovats Retention Indices

Not Available

Spectra

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tulipinolide 10V, Positive-QTOF	splash10-0006-0090000000-54c034628b4c72a618d1	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tulipinolide 20V, Positive-QTOF	splash10-003r-1590000000-f2f8ba743d2adf07db87	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tulipinolide 40V, Positive-QTOF	splash10-067i-8930000000-aff3faeb0b7d4e6e9c01	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tulipinolide 10V, Negative-QTOF	splash10-000j-0090000000-f6517849308075c0902a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tulipinolide 20V, Negative-QTOF	splash10-000b-2090000000-e2cb4d4d58b170fb9d5d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tulipinolide 40V, Negative-QTOF	splash10-059f-9730000000-667f74e35a5673a01df4	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tulipinolide 10V, Positive-QTOF	splash10-000t-0090000000-50e71a036f2205e62edc	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tulipinolide 20V, Positive-QTOF	splash10-001i-0290000000-36acec79491d6a3126f9	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tulipinolide 40V, Positive-QTOF	splash10-0ae9-1590000000-98ce2e8a788e952c73c4	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tulipinolide 10V, Negative-QTOF	splash10-0a4i-9030000000-fbea22a3cc95a5df97e1	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tulipinolide 20V, Negative-QTOF	splash10-0a4i-9050000000-6e0edae293cab189749e	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tulipinolide 40V, Negative-QTOF	splash10-0a4i-9010000000-f6230ad3cc97ec27ad71	2021-10-21	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

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

FDB015625

KNApSAcK ID

Not Available

Chemspider ID

4479737

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5322173

PDB ID

Not Available

ChEBI ID

Not Available

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

Not Available

Showing metabocard for Tulipinolide (HMDB0303566)

MOL for HMDB0303566 (Tulipinolide)

3D MOL for HMDB0303566 (Tulipinolide)

3D SDF for HMDB0303566 (Tulipinolide)

3D-SDF for HMDB0303566 (Tulipinolide)

PDB for HMDB0303566 (Tulipinolide)

3D PDB for HMDB0303566 (Tulipinolide)

SMILES for HMDB0303566 (Tulipinolide)

INCHI for HMDB0303566 (Tulipinolide)

Structure for HMDB0303566 (Tulipinolide)

3D Structure for HMDB0303566 (Tulipinolide)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

MS/MS Spectra