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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-12 02:38:08 UTC

Update Date

2022-03-07 02:56:50 UTC

HMDB ID

HMDB0041003

Secondary Accession Numbers

HMDB41003

Metabolite Identification

Common Name

Vulgarolide

Description

Vulgarolide, also known as secobryononate, belongs to the class of organic compounds known as oxanes. Oxanes are compounds containing an oxane (tetrahydropyran) ring, which is a six-member saturated aliphatic heterocycle with one oxygen atom and five carbon atoms. Vulgarolide has been detected, but not quantified in, herbs and spices. This could make vulgarolide a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Vulgarolide.

Structure

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

HMDB0041003
     RDKit          3D
Vulgarolide
 40 42  0  0  0  0  0  0  0  0999 V2000
    3.0905   -1.5968    0.9250 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2902   -1.4275   -0.0926 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4248   -2.4264   -0.7117 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1377   -3.5884   -0.3330 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9245   -1.8391   -1.8897 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7322   -0.4602   -1.4996 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0589   -0.2059   -0.8779 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2851    1.0798   -0.2378 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6997    1.3600    1.0913 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2719    1.7356    0.9846 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2264    1.8496    2.0825 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6739    2.0001   -0.1125 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2984    0.7675   -0.6669 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6555    0.9435   -2.1507 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5892    0.5075    0.0493 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4918   -0.2827    1.3029 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3539   -1.2561    1.2885 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0859   -1.7721    2.5493 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1843   -0.7542    0.7205 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4478   -0.4717   -0.5954 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7018   -0.8065    1.3267 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1480   -2.5799    1.3948 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5461    0.1578   -2.4063 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8130   -0.2838   -1.7340 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9423    1.8908   -0.9309 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3995    1.2537   -0.1577 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2070    2.3082    1.4644 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8813    0.5970    1.8736 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4801    2.7045    0.1884 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1709    2.5214   -0.9815 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6673    1.3772   -2.2079 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8823    1.6543   -2.5492 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5523   -0.0007   -2.7049 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0379    1.5232    0.2583 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3407    0.0372   -0.6488 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5131    0.3405    2.2257 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4305   -0.9094    1.3888 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6699   -2.1083    0.6175 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6501   -2.5473    2.6998 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1521   -1.2927   -0.9428 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  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
  7  2  1  0
 20 13  1  0
 20  6  1  0
  1 21  1  0
  1 22  1  0
  6 23  1  0
  7 24  1  0
  8 25  1  0
  8 26  1  0
  9 27  1  0
  9 28  1  0
 12 29  1  0
 12 30  1  0
 14 31  1  0
 14 32  1  0
 14 33  1  0
 15 34  1  0
 15 35  1  0
 16 36  1  0
 16 37  1  0
 17 38  1  0
 18 39  1  0
 20 40  1  0
M  END


  Mrv0541 05061312192D          

 20 22  0  0  0  0            999 V2000
    5.9127    0.9903    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8229    0.3043    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9242   -0.5085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4809    0.1003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3996    1.7995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6486    1.0130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4912    0.0112    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1615    1.3316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1001   -0.5455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4440    0.9245    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9563    2.4084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8351    1.4812    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0109    1.4443    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9961    2.1398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4542    0.8354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8188   -1.3210    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7073    3.1950    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5528    2.7487    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7619    2.2308    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1763    2.2323    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  1  0  0  0  0
  6  5  1  0  0  0  0
  8  1  2  0  0  0  0
  9  3  1  0  0  0  0
  9  7  1  0  0  0  0
 10  4  1  0  0  0  0
 10  8  1  0  0  0  0
 11  5  1  0  0  0  0
 12 10  1  0  0  0  0
 13 12  1  0  0  0  0
 14  8  1  0  0  0  0
 15  2  1  0  0  0  0
 15  6  1  0  0  0  0
 15  7  1  0  0  0  0
 15 13  1  0  0  0  0
 16  9  2  0  0  0  0
 17 11  1  0  0  0  0
 18 14  2  0  0  0  0
 19 11  1  0  0  0  0
 19 13  1  0  0  0  0
 20 12  1  0  0  0  0
 20 14  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0041003

> <DATABASE_NAME>
hmdb

> <SMILES>
CC12CCC(O)OC1C1OC(=O)C(=C)C1CCC(=O)C2

> <INCHI_IDENTIFIER>
InChI=1S/C15H20O5/c1-8-10-4-3-9(16)7-15(2)6-5-11(17)19-13(15)12(10)20-14(8)18/h10-13,17H,1,3-7H2,2H3

> <INCHI_KEY>
LBKCMFUBEOROEX-UHFFFAOYSA-N

> <FORMULA>
C15H20O5

> <MOLECULAR_WEIGHT>
280.3163

> <EXACT_MASS>
280.13107375

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
28.95410024878195

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
14-hydroxy-11-methyl-5-methylidene-3,15-dioxatricyclo[9.4.0.0²,⁶]pentadecane-4,9-dione

> <ALOGPS_LOGP>
0.23

> <JCHEM_LOGP>
1.5183318486666666

> <ALOGPS_LOGS>
-1.52

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
19.018537461733427

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.464487503718328

> <JCHEM_PKA_STRONGEST_BASIC>
-3.9078331018505184

> <JCHEM_POLAR_SURFACE_AREA>
72.83

> <JCHEM_REFRACTIVITY>
69.7347

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.44e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
14-hydroxy-11-methyl-5-methylidene-3,15-dioxatricyclo[9.4.0.0²,⁶]pentadecane-4,9-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0041003
     RDKit          3D
Vulgarolide
 40 42  0  0  0  0  0  0  0  0999 V2000
    3.0905   -1.5968    0.9250 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2902   -1.4275   -0.0926 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4248   -2.4264   -0.7117 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1377   -3.5884   -0.3330 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9245   -1.8391   -1.8897 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7322   -0.4602   -1.4996 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0589   -0.2059   -0.8779 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2851    1.0798   -0.2378 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6997    1.3600    1.0913 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2719    1.7356    0.9846 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2264    1.8496    2.0825 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6739    2.0001   -0.1125 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2984    0.7675   -0.6669 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6555    0.9435   -2.1507 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5892    0.5075    0.0493 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4918   -0.2827    1.3029 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3539   -1.2561    1.2885 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0859   -1.7721    2.5493 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1843   -0.7542    0.7205 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4478   -0.4717   -0.5954 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7018   -0.8065    1.3267 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1480   -2.5799    1.3948 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5461    0.1578   -2.4063 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8130   -0.2838   -1.7340 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9423    1.8908   -0.9309 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3995    1.2537   -0.1577 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2070    2.3082    1.4644 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8813    0.5970    1.8736 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4801    2.7045    0.1884 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1709    2.5214   -0.9815 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6673    1.3772   -2.2079 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8823    1.6543   -2.5492 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5523   -0.0007   -2.7049 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0379    1.5232    0.2583 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3407    0.0372   -0.6488 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5131    0.3405    2.2257 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4305   -0.9094    1.3888 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6699   -2.1083    0.6175 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6501   -2.5473    2.6998 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1521   -1.2927   -0.9428 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  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
  7  2  1  0
 20 13  1  0
 20  6  1  0
  1 21  1  0
  1 22  1  0
  6 23  1  0
  7 24  1  0
  8 25  1  0
  8 26  1  0
  9 27  1  0
  9 28  1  0
 12 29  1  0
 12 30  1  0
 14 31  1  0
 14 32  1  0
 14 33  1  0
 15 34  1  0
 15 35  1  0
 16 36  1  0
 16 37  1  0
 17 38  1  0
 18 39  1  0
 20 40  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      11.037   1.849   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.403   0.568   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.325  -0.949   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.364   0.187   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.613   3.359   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.077   1.891   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.650   0.021   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.635   2.486   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.787  -1.018   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.295   1.726   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.652   4.496   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.159   2.765   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.620   2.696   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.326   3.994   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.581   1.559   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       5.262  -2.466   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       3.187   5.964   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      10.365   5.131   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       5.156   4.164   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       7.796   4.167   0.000  0.00  0.00           O+0
CONECT    1    8                                                            
CONECT    2   15                                                            
CONECT    3    4    9                                                       
CONECT    4    3   10                                                       
CONECT    5    6   11                                                       
CONECT    6    5   15                                                       
CONECT    7    9   15                                                       
CONECT    8    1   10   14                                                  
CONECT    9    3    7   16                                                  
CONECT   10    4    8   12                                                  
CONECT   11    5   17   19                                                  
CONECT   12   10   13   20                                                  
CONECT   13   12   15   19                                                  
CONECT   14    8   18   20                                                  
CONECT   15    2    6    7   13                                             
CONECT   16    9                                                            
CONECT   17   11                                                            
CONECT   18   14                                                            
CONECT   19   11   13                                                       
CONECT   20   12   14                                                       
MASTER        0    0    0    0    0    0    0    0   20    0   44    0
END

COMPND    HMDB0041003
HETATM    1  C1  UNL     1       3.090  -1.597   0.925  1.00  0.00           C  
HETATM    2  C2  UNL     1       2.290  -1.428  -0.093  1.00  0.00           C  
HETATM    3  C3  UNL     1       1.425  -2.426  -0.712  1.00  0.00           C  
HETATM    4  O1  UNL     1       1.138  -3.588  -0.333  1.00  0.00           O  
HETATM    5  O2  UNL     1       0.925  -1.839  -1.890  1.00  0.00           O  
HETATM    6  C4  UNL     1       0.732  -0.460  -1.500  1.00  0.00           C  
HETATM    7  C5  UNL     1       2.059  -0.206  -0.878  1.00  0.00           C  
HETATM    8  C6  UNL     1       2.285   1.080  -0.238  1.00  0.00           C  
HETATM    9  C7  UNL     1       1.700   1.360   1.091  1.00  0.00           C  
HETATM   10  C8  UNL     1       0.272   1.736   0.985  1.00  0.00           C  
HETATM   11  O3  UNL     1      -0.226   1.850   2.082  1.00  0.00           O  
HETATM   12  C9  UNL     1      -0.674   2.000  -0.112  1.00  0.00           C  
HETATM   13  C10 UNL     1      -1.298   0.767  -0.667  1.00  0.00           C  
HETATM   14  C11 UNL     1      -1.656   0.944  -2.151  1.00  0.00           C  
HETATM   15  C12 UNL     1      -2.589   0.508   0.049  1.00  0.00           C  
HETATM   16  C13 UNL     1      -2.492  -0.283   1.303  1.00  0.00           C  
HETATM   17  C14 UNL     1      -1.354  -1.256   1.289  1.00  0.00           C  
HETATM   18  O4  UNL     1      -1.086  -1.772   2.549  1.00  0.00           O  
HETATM   19  O5  UNL     1      -0.184  -0.754   0.720  1.00  0.00           O  
HETATM   20  C15 UNL     1      -0.448  -0.472  -0.595  1.00  0.00           C  
HETATM   21  H1  UNL     1       3.702  -0.806   1.327  1.00  0.00           H  
HETATM   22  H2  UNL     1       3.148  -2.580   1.395  1.00  0.00           H  
HETATM   23  H3  UNL     1       0.546   0.158  -2.406  1.00  0.00           H  
HETATM   24  H4  UNL     1       2.813  -0.284  -1.734  1.00  0.00           H  
HETATM   25  H5  UNL     1       1.942   1.891  -0.931  1.00  0.00           H  
HETATM   26  H6  UNL     1       3.399   1.254  -0.158  1.00  0.00           H  
HETATM   27  H7  UNL     1       2.207   2.308   1.464  1.00  0.00           H  
HETATM   28  H8  UNL     1       1.881   0.597   1.874  1.00  0.00           H  
HETATM   29  H9  UNL     1      -1.480   2.705   0.188  1.00  0.00           H  
HETATM   30  H10 UNL     1      -0.171   2.521  -0.982  1.00  0.00           H  
HETATM   31  H11 UNL     1      -2.667   1.377  -2.208  1.00  0.00           H  
HETATM   32  H12 UNL     1      -0.882   1.654  -2.549  1.00  0.00           H  
HETATM   33  H13 UNL     1      -1.552  -0.001  -2.705  1.00  0.00           H  
HETATM   34  H14 UNL     1      -3.038   1.523   0.258  1.00  0.00           H  
HETATM   35  H15 UNL     1      -3.341   0.037  -0.649  1.00  0.00           H  
HETATM   36  H16 UNL     1      -2.513   0.340   2.226  1.00  0.00           H  
HETATM   37  H17 UNL     1      -3.431  -0.909   1.389  1.00  0.00           H  
HETATM   38  H18 UNL     1      -1.670  -2.108   0.617  1.00  0.00           H  
HETATM   39  H19 UNL     1      -1.650  -2.547   2.700  1.00  0.00           H  
HETATM   40  H20 UNL     1      -1.152  -1.293  -0.943  1.00  0.00           H  
CONECT    1    2    2   21   22
CONECT    2    3    7
CONECT    3    4    4    5
CONECT    5    6
CONECT    6    7   20   23
CONECT    7    8   24
CONECT    8    9   25   26
CONECT    9   10   27   28
CONECT   10   11   11   12
CONECT   12   13   29   30
CONECT   13   14   15   20
CONECT   14   31   32   33
CONECT   15   16   34   35
CONECT   16   17   36   37
CONECT   17   18   19   38
CONECT   18   39
CONECT   19   20
CONECT   20   40
END

HMDB0041003
     RDKit          3D
Vulgarolide
 40 42  0  0  0  0  0  0  0  0999 V2000
    3.0905   -1.5968    0.9250 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2902   -1.4275   -0.0926 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4248   -2.4264   -0.7117 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1377   -3.5884   -0.3330 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9245   -1.8391   -1.8897 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7322   -0.4602   -1.4996 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0589   -0.2059   -0.8779 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2851    1.0798   -0.2378 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6997    1.3600    1.0913 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2719    1.7356    0.9846 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2264    1.8496    2.0825 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6739    2.0001   -0.1125 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2984    0.7675   -0.6669 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6555    0.9435   -2.1507 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5892    0.5075    0.0493 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4918   -0.2827    1.3029 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3539   -1.2561    1.2885 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0859   -1.7721    2.5493 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1843   -0.7542    0.7205 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4478   -0.4717   -0.5954 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7018   -0.8065    1.3267 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1480   -2.5799    1.3948 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5461    0.1578   -2.4063 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8130   -0.2838   -1.7340 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9423    1.8908   -0.9309 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3995    1.2537   -0.1577 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2070    2.3082    1.4644 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8813    0.5970    1.8736 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4801    2.7045    0.1884 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1709    2.5214   -0.9815 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6673    1.3772   -2.2079 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8823    1.6543   -2.5492 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5523   -0.0007   -2.7049 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0379    1.5232    0.2583 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3407    0.0372   -0.6488 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5131    0.3405    2.2257 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4305   -0.9094    1.3888 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6699   -2.1083    0.6175 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6501   -2.5473    2.6998 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1521   -1.2927   -0.9428 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  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
  7  2  1  0
 20 13  1  0
 20  6  1  0
  1 21  1  0
  1 22  1  0
  6 23  1  0
  7 24  1  0
  8 25  1  0
  8 26  1  0
  9 27  1  0
  9 28  1  0
 12 29  1  0
 12 30  1  0
 14 31  1  0
 14 32  1  0
 14 33  1  0
 15 34  1  0
 15 35  1  0
 16 36  1  0
 16 37  1  0
 17 38  1  0
 18 39  1  0
 20 40  1  0
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
Secobryononate	HMDB

Chemical Formula

C₁₅H₂₀O₅

Average Molecular Weight

280.3163

Monoisotopic Molecular Weight

280.13107375

IUPAC Name

14-hydroxy-11-methyl-5-methylidene-3,15-dioxatricyclo[9.4.0.0²,⁶]pentadecane-4,9-dione

Traditional Name

14-hydroxy-11-methyl-5-methylidene-3,15-dioxatricyclo[9.4.0.0²,⁶]pentadecane-4,9-dione

CAS Registry Number

120674-40-0

SMILES

CC12CCC(O)OC1C1OC(=O)C(=C)C1CCC(=O)C2

InChI Identifier

InChI=1S/C15H20O5/c1-8-10-4-3-9(16)7-15(2)6-5-11(17)19-13(15)12(10)20-14(8)18/h10-13,17H,1,3-7H2,2H3

InChI Key

LBKCMFUBEOROEX-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as oxanes. Oxanes are compounds containing an oxane (tetrahydropyran) ring, which is a six-member saturated aliphatic heterocycle with one oxygen atom and five carbon atoms.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Oxanes

Sub Class

Not Available

Direct Parent

Oxanes

Alternative Parents

Substituents

Gamma butyrolactone
Oxane
Tetrahydrofuran
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Cyclic ketone
Lactone
Ketone
Hemiacetal
Carboxylic acid ester
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Oxacycle
Carbonyl group
Organic oxide
Organooxygen compound
Organic oxygen compound
Hydrocarbon derivative
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0041003)
Cytoplasm (HMDB: HMDB0041003)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0041003)

Source

Exogenous

Food

Food (HMDB: HMDB0041003)

Herb and spice

Herbs and Spices (FooDB: FOOD00866)

Endogenous

Plant

Plant (HMDB: HMDB0041003)

Not Available

Nutrient (HMDB: HMDB0041003)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0041003)

Emulsifier (HMDB: HMDB0041003)

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
Water Solubility	8.44 g/L	ALOGPS
logP	0.23	ALOGPS
logP	1.52	ChemAxon
logS	-1.5	ALOGPS
pKa (Strongest Acidic)	12.46	ChemAxon
pKa (Strongest Basic)	-3.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	72.83 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	69.73 m³·mol⁻¹	ChemAxon
Polarizability	28.95 Å³	ChemAxon
Number of Rings	3	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]+	166.904	31661259
DarkChem	[M-H]-	160.265	31661259
DeepCCS	[M-2H]-	196.671	30932474
DeepCCS	[M+Na]+	172.236	30932474
AllCCS	[M+H]+	166.1	32859911
AllCCS	[M+H-H2O]+	162.6	32859911
AllCCS	[M+NH4]+	169.4	32859911
AllCCS	[M+Na]+	170.3	32859911
AllCCS	[M-H]-	169.4	32859911
AllCCS	[M+Na-2H]-	169.3	32859911
AllCCS	[M+HCOO]-	169.3	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Vulgarolide	CC12CCC(O)OC1C1OC(=O)C(=C)C1CCC(=O)C2	3206.2	Standard polar	33892256
Vulgarolide	CC12CCC(O)OC1C1OC(=O)C(=C)C1CCC(=O)C2	2233.7	Standard non polar	33892256
Vulgarolide	CC12CCC(O)OC1C1OC(=O)C(=C)C1CCC(=O)C2	2488.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Vulgarolide,1TMS,isomer #1	C=C1C(=O)OC2C1CCC(=O)CC1(C)CCC(O[Si](C)(C)C)OC21	2457.3	Semi standard non polar	33892256
Vulgarolide,1TMS,isomer #2	C=C1C(=O)OC2C1CCC(O[Si](C)(C)C)=CC1(C)CCC(O)OC21	2472.0	Semi standard non polar	33892256
Vulgarolide,1TMS,isomer #3	C=C1C(=O)OC2C1CC=C(O[Si](C)(C)C)CC1(C)CCC(O)OC21	2484.6	Semi standard non polar	33892256
Vulgarolide,2TMS,isomer #1	C=C1C(=O)OC2C1CCC(O[Si](C)(C)C)=CC1(C)CCC(O[Si](C)(C)C)OC21	2464.3	Semi standard non polar	33892256
Vulgarolide,2TMS,isomer #1	C=C1C(=O)OC2C1CCC(O[Si](C)(C)C)=CC1(C)CCC(O[Si](C)(C)C)OC21	2250.5	Standard non polar	33892256
Vulgarolide,2TMS,isomer #2	C=C1C(=O)OC2C1CC=C(O[Si](C)(C)C)CC1(C)CCC(O[Si](C)(C)C)OC21	2493.4	Semi standard non polar	33892256
Vulgarolide,2TMS,isomer #2	C=C1C(=O)OC2C1CC=C(O[Si](C)(C)C)CC1(C)CCC(O[Si](C)(C)C)OC21	2266.0	Standard non polar	33892256
Vulgarolide,1TBDMS,isomer #1	C=C1C(=O)OC2C1CCC(=O)CC1(C)CCC(O[Si](C)(C)C(C)(C)C)OC21	2717.5	Semi standard non polar	33892256
Vulgarolide,1TBDMS,isomer #2	C=C1C(=O)OC2C1CCC(O[Si](C)(C)C(C)(C)C)=CC1(C)CCC(O)OC21	2693.8	Semi standard non polar	33892256
Vulgarolide,1TBDMS,isomer #3	C=C1C(=O)OC2C1CC=C(O[Si](C)(C)C(C)(C)C)CC1(C)CCC(O)OC21	2712.5	Semi standard non polar	33892256
Vulgarolide,2TBDMS,isomer #1	C=C1C(=O)OC2C1CCC(O[Si](C)(C)C(C)(C)C)=CC1(C)CCC(O[Si](C)(C)C(C)(C)C)OC21	2893.8	Semi standard non polar	33892256
Vulgarolide,2TBDMS,isomer #1	C=C1C(=O)OC2C1CCC(O[Si](C)(C)C(C)(C)C)=CC1(C)CCC(O[Si](C)(C)C(C)(C)C)OC21	2646.2	Standard non polar	33892256
Vulgarolide,2TBDMS,isomer #2	C=C1C(=O)OC2C1CC=C(O[Si](C)(C)C(C)(C)C)CC1(C)CCC(O[Si](C)(C)C(C)(C)C)OC21	2927.9	Semi standard non polar	33892256
Vulgarolide,2TBDMS,isomer #2	C=C1C(=O)OC2C1CC=C(O[Si](C)(C)C(C)(C)C)CC1(C)CCC(O[Si](C)(C)C(C)(C)C)OC21	2658.8	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Vulgarolide GC-MS (Non-derivatized) - 70eV, Positive	splash10-01tj-4890000000-486b8ecf5f1a1d341410	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Vulgarolide GC-MS (1 TMS) - 70eV, Positive	splash10-000i-6934000000-19b53cde736b29e14f42	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Vulgarolide 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 - Vulgarolide 10V, Positive-QTOF	splash10-001i-0090000000-ee21344813df562df557	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vulgarolide 20V, Positive-QTOF	splash10-0bti-0290000000-c50fc4e30e8e2b986eec	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vulgarolide 40V, Positive-QTOF	splash10-0c2c-9750000000-ca5d491b6c96b6fc5c34	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vulgarolide 10V, Negative-QTOF	splash10-004i-0090000000-6bec0423ab621222a625	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vulgarolide 20V, Negative-QTOF	splash10-01s9-0090000000-304d8253d4f1f45d92eb	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vulgarolide 40V, Negative-QTOF	splash10-06wc-5920000000-2cece621b1ad36af1b76	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vulgarolide 10V, Negative-QTOF	splash10-004i-0090000000-48f5e9ec9dacb4aa8b83	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vulgarolide 20V, Negative-QTOF	splash10-004i-1490000000-8721ab6ca44cf70c7eb1	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vulgarolide 40V, Negative-QTOF	splash10-024i-3490000000-c3f070e3dea934d571ef	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vulgarolide 10V, Positive-QTOF	splash10-01q9-0090000000-f546b0aaa8534c0a38e1	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vulgarolide 20V, Positive-QTOF	splash10-01q9-0090000000-1096478587eaf3b4991c	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vulgarolide 40V, Positive-QTOF	splash10-08fr-1590000000-61b75f7ec335b7c6e474	2021-09-24	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

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

FDB020863

KNApSAcK ID

C00057823

Chemspider ID

35015075

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

78101312

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

(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for Vulgarolide (HMDB0041003)

MOL for HMDB0041003 (Vulgarolide)

3D MOL for HMDB0041003 (Vulgarolide)

3D SDF for HMDB0041003 (Vulgarolide)

3D-SDF for HMDB0041003 (Vulgarolide)

PDB for HMDB0041003 (Vulgarolide)

3D PDB for HMDB0041003 (Vulgarolide)

SMILES for HMDB0041003 (Vulgarolide)

INCHI for HMDB0041003 (Vulgarolide)

Structure for HMDB0041003 (Vulgarolide)

3D Structure for HMDB0041003 (Vulgarolide)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra