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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 23:26:21 UTC

Update Date

2022-03-07 02:55:39 UTC

HMDB ID

HMDB0038156

Secondary Accession Numbers

HMDB38156

Metabolite Identification

Common Name

Umbellifolide

Description

Umbellifolide belongs to the class of organic compounds known as benzofurans. These are organic compounds containing a benzene ring fused to a furan. Furan is a five-membered aromatic ring with four carbon atoms and one oxygen atom. Umbellifolide has been detected, but not quantified in, several different foods, such as red tea, green tea, black tea, herbal tea, and herbs and spices. This could make umbellifolide a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Umbellifolide.

Structure

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

HMDB0038156
     RDKit          3D
Umbellifolide
 39 40  0  0  0  0  0  0  0  0999 V2000
    5.1069    0.7073    0.6302 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0559    0.0530    0.2029 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9338   -0.7554   -0.9952 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8817   -1.0768   -1.7699 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5682   -1.0987   -1.1109 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0611   -1.1359    0.2092 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5847   -1.1865    0.2841 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1019    0.1616    0.0824 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1164    0.4134   -1.3878 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4871    0.0116    0.6679 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2859   -1.0471    0.0017 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6420   -1.1617    0.6194 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5053    0.0130    0.5364 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2797    1.2207   -0.2785 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5596    0.0385    1.2115 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6240    1.1888    0.8638 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1140    1.9144    1.6964 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0695    1.3353    0.6059 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7395    0.0049    0.8798 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0954    1.2822    1.5385 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0616    0.7119    0.0954 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4528   -2.0752    0.6553 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2896   -1.5134    1.3053 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1821   -1.8519   -0.4916 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9123    0.7122   -1.6832 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8041    1.1973   -1.7309 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3005   -0.5582   -1.9111 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3843   -0.3122    1.7495 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0541    0.9476    0.7231 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4455   -0.8698   -1.0841 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8021   -2.0547    0.0560 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2172   -2.0309    0.1723 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5846   -1.4533    1.7113 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5505    1.1114   -1.0921 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2439    1.4932   -0.8171 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0461    2.1356    0.3059 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5406    2.0717    1.2856 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2729    1.6221   -0.4467 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8642   -0.1661    1.9763 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
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  2  0
  8 16  1  0
 16 17  2  0
 16 18  1  0
 18 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
  7 24  1  0
  9 25  1  0
  9 26  1  0
  9 27  1  0
 10 28  1  0
 10 29  1  0
 11 30  1  0
 11 31  1  0
 12 32  1  0
 12 33  1  0
 14 34  1  0
 14 35  1  0
 14 36  1  0
 18 37  1  0
 18 38  1  0
 19 39  1  0
M  END

  Mrv0541 05061310162D          

 19 20  0  0  0  0            999 V2000
   -1.4929    3.2767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0368    2.7814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5492    4.3212    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6505    3.6892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0640    3.2767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3650    3.2767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1741    2.7707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6098    4.3212    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7784    3.6892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5289    3.4315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7044    3.4027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4222    4.1779    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3616    2.9140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7563    4.2245    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0795    3.6892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7784    4.5142    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8313    2.2820    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5315    4.5067    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0723    4.6859    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  4  1  0  0  0  0
  6  4  1  0  0  0  0
  9  1  1  0  0  0  0
  9  5  1  0  0  0  0
 10  2  2  0  0  0  0
 11  7  1  0  0  0  0
 11 10  1  0  0  0  0
 12  8  1  0  0  0  0
 12 11  1  0  0  0  0
 13  7  1  0  0  0  0
 14 10  1  0  0  0  0
 15  3  1  0  0  0  0
 15  6  1  0  0  0  0
 15  8  1  0  0  0  0
 15 13  1  0  0  0  0
 16  9  2  0  0  0  0
 17 13  2  0  0  0  0
 18 14  2  0  0  0  0
 19 12  1  0  0  0  0
 19 14  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0038156

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(=O)CCCC1(C)CC2OC(=O)C(=C)C2CC1=O

> <INCHI_IDENTIFIER>
InChI=1S/C15H20O4/c1-9(16)5-4-6-15(3)8-12-11(7-13(15)17)10(2)14(18)19-12/h11-12H,2,4-8H2,1,3H3

> <INCHI_KEY>
MIRSLSRVCIOISZ-UHFFFAOYSA-N

> <FORMULA>
C15H20O4

> <MOLECULAR_WEIGHT>
264.3169

> <EXACT_MASS>
264.136159128

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
28.089192224975612

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
6-methyl-3-methylidene-6-(4-oxopentyl)-octahydro-1-benzofuran-2,5-dione

> <ALOGPS_LOGP>
1.38

> <JCHEM_LOGP>
2.381977904333333

> <ALOGPS_LOGS>
-2.89

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
19.645149613474977

> <JCHEM_PKA_STRONGEST_ACIDIC>
17.324156149594263

> <JCHEM_PKA_STRONGEST_BASIC>
-6.652524174820898

> <JCHEM_POLAR_SURFACE_AREA>
60.44

> <JCHEM_REFRACTIVITY>
69.6356

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.40e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
6-methyl-3-methylidene-6-(4-oxopentyl)-tetrahydro-1-benzofuran-2,5-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0038156
     RDKit          3D
Umbellifolide
 39 40  0  0  0  0  0  0  0  0999 V2000
    5.1069    0.7073    0.6302 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0559    0.0530    0.2029 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9338   -0.7554   -0.9952 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8817   -1.0768   -1.7699 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5682   -1.0987   -1.1109 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0611   -1.1359    0.2092 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5847   -1.1865    0.2841 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1019    0.1616    0.0824 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1164    0.4134   -1.3878 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4871    0.0116    0.6679 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2859   -1.0471    0.0017 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6420   -1.1617    0.6194 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5053    0.0130    0.5364 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2797    1.2207   -0.2785 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5596    0.0385    1.2115 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6240    1.1888    0.8638 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1140    1.9144    1.6964 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0695    1.3353    0.6059 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7395    0.0049    0.8798 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0954    1.2822    1.5385 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0616    0.7119    0.0954 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4528   -2.0752    0.6553 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2896   -1.5134    1.3053 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1821   -1.8519   -0.4916 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9123    0.7122   -1.6832 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8041    1.1973   -1.7309 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3005   -0.5582   -1.9111 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3843   -0.3122    1.7495 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0541    0.9476    0.7231 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4455   -0.8698   -1.0841 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8021   -2.0547    0.0560 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2172   -2.0309    0.1723 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5846   -1.4533    1.7113 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5505    1.1114   -1.0921 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2439    1.4932   -0.8171 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0461    2.1356    0.3059 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5406    2.0717    1.2856 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2729    1.6221   -0.4467 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8642   -0.1661    1.9763 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
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  2  0
  8 16  1  0
 16 17  2  0
 16 18  1  0
 18 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
  7 24  1  0
  9 25  1  0
  9 26  1  0
  9 27  1  0
 10 28  1  0
 10 29  1  0
 11 30  1  0
 11 31  1  0
 12 32  1  0
 12 33  1  0
 14 34  1  0
 14 35  1  0
 14 36  1  0
 18 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      -2.787   6.117   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.402   5.192   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.892   8.066   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.214   6.887   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.119   6.117   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.548   6.117   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.925   5.172   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.872   8.066   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.453   6.887   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.454   6.405   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.915   6.352   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.388   7.799   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.408   5.439   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.878   7.886   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.882   6.887   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -1.453   8.427   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       3.418   4.260   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      10.325   8.413   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       7.602   8.747   0.000  0.00  0.00           O+0
CONECT    1    9                                                            
CONECT    2   10                                                            
CONECT    3   15                                                            
CONECT    4    5    6                                                       
CONECT    5    4    9                                                       
CONECT    6    4   15                                                       
CONECT    7   11   13                                                       
CONECT    8   12   15                                                       
CONECT    9    1    5   16                                                  
CONECT   10    2   11   14                                                  
CONECT   11    7   10   12                                                  
CONECT   12    8   11   19                                                  
CONECT   13    7   15   17                                                  
CONECT   14   10   18   19                                                  
CONECT   15    3    6    8   13                                             
CONECT   16    9                                                            
CONECT   17   13                                                            
CONECT   18   14                                                            
CONECT   19   12   14                                                       
MASTER        0    0    0    0    0    0    0    0   19    0   40    0
END

COMPND    HMDB0038156
HETATM    1  C1  UNL     1       5.107   0.707   0.630  1.00  0.00           C  
HETATM    2  C2  UNL     1       4.056   0.053   0.203  1.00  0.00           C  
HETATM    3  C3  UNL     1       3.934  -0.755  -0.995  1.00  0.00           C  
HETATM    4  O1  UNL     1       4.882  -1.077  -1.770  1.00  0.00           O  
HETATM    5  O2  UNL     1       2.568  -1.099  -1.111  1.00  0.00           O  
HETATM    6  C4  UNL     1       2.061  -1.136   0.209  1.00  0.00           C  
HETATM    7  C5  UNL     1       0.585  -1.187   0.284  1.00  0.00           C  
HETATM    8  C6  UNL     1      -0.102   0.162   0.082  1.00  0.00           C  
HETATM    9  C7  UNL     1      -0.116   0.413  -1.388  1.00  0.00           C  
HETATM   10  C8  UNL     1      -1.487   0.012   0.668  1.00  0.00           C  
HETATM   11  C9  UNL     1      -2.286  -1.047   0.002  1.00  0.00           C  
HETATM   12  C10 UNL     1      -3.642  -1.162   0.619  1.00  0.00           C  
HETATM   13  C11 UNL     1      -4.505   0.013   0.536  1.00  0.00           C  
HETATM   14  C12 UNL     1      -4.280   1.221  -0.279  1.00  0.00           C  
HETATM   15  O3  UNL     1      -5.560   0.039   1.212  1.00  0.00           O  
HETATM   16  C13 UNL     1       0.624   1.189   0.864  1.00  0.00           C  
HETATM   17  O4  UNL     1       0.114   1.914   1.696  1.00  0.00           O  
HETATM   18  C14 UNL     1       2.070   1.335   0.606  1.00  0.00           C  
HETATM   19  C15 UNL     1       2.739   0.005   0.880  1.00  0.00           C  
HETATM   20  H1  UNL     1       5.095   1.282   1.538  1.00  0.00           H  
HETATM   21  H2  UNL     1       6.062   0.712   0.095  1.00  0.00           H  
HETATM   22  H3  UNL     1       2.453  -2.075   0.655  1.00  0.00           H  
HETATM   23  H4  UNL     1       0.290  -1.513   1.305  1.00  0.00           H  
HETATM   24  H5  UNL     1       0.182  -1.852  -0.492  1.00  0.00           H  
HETATM   25  H6  UNL     1       0.912   0.712  -1.683  1.00  0.00           H  
HETATM   26  H7  UNL     1      -0.804   1.197  -1.731  1.00  0.00           H  
HETATM   27  H8  UNL     1      -0.301  -0.558  -1.911  1.00  0.00           H  
HETATM   28  H9  UNL     1      -1.384  -0.312   1.750  1.00  0.00           H  
HETATM   29  H10 UNL     1      -2.054   0.948   0.723  1.00  0.00           H  
HETATM   30  H11 UNL     1      -2.445  -0.870  -1.084  1.00  0.00           H  
HETATM   31  H12 UNL     1      -1.802  -2.055   0.056  1.00  0.00           H  
HETATM   32  H13 UNL     1      -4.217  -2.031   0.172  1.00  0.00           H  
HETATM   33  H14 UNL     1      -3.585  -1.453   1.711  1.00  0.00           H  
HETATM   34  H15 UNL     1      -3.551   1.111  -1.092  1.00  0.00           H  
HETATM   35  H16 UNL     1      -5.244   1.493  -0.817  1.00  0.00           H  
HETATM   36  H17 UNL     1      -4.046   2.136   0.306  1.00  0.00           H  
HETATM   37  H18 UNL     1       2.541   2.072   1.286  1.00  0.00           H  
HETATM   38  H19 UNL     1       2.273   1.622  -0.447  1.00  0.00           H  
HETATM   39  H20 UNL     1       2.864  -0.166   1.976  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   23   24
CONECT    8    9   10   16
CONECT    9   25   26   27
CONECT   10   11   28   29
CONECT   11   12   30   31
CONECT   12   13   32   33
CONECT   13   14   15   15
CONECT   14   34   35   36
CONECT   16   17   17   18
CONECT   18   19   37   38
CONECT   19   39
END

HMDB0038156
     RDKit          3D
Umbellifolide
 39 40  0  0  0  0  0  0  0  0999 V2000
    5.1069    0.7073    0.6302 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0559    0.0530    0.2029 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9338   -0.7554   -0.9952 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8817   -1.0768   -1.7699 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5682   -1.0987   -1.1109 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0611   -1.1359    0.2092 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5847   -1.1865    0.2841 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1019    0.1616    0.0824 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1164    0.4134   -1.3878 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4871    0.0116    0.6679 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2859   -1.0471    0.0017 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6420   -1.1617    0.6194 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5053    0.0130    0.5364 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2797    1.2207   -0.2785 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5596    0.0385    1.2115 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6240    1.1888    0.8638 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1140    1.9144    1.6964 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0695    1.3353    0.6059 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7395    0.0049    0.8798 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0954    1.2822    1.5385 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0616    0.7119    0.0954 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4528   -2.0752    0.6553 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2896   -1.5134    1.3053 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1821   -1.8519   -0.4916 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9123    0.7122   -1.6832 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8041    1.1973   -1.7309 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3005   -0.5582   -1.9111 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3843   -0.3122    1.7495 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0541    0.9476    0.7231 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4455   -0.8698   -1.0841 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8021   -2.0547    0.0560 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2172   -2.0309    0.1723 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5846   -1.4533    1.7113 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5505    1.1114   -1.0921 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2439    1.4932   -0.8171 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0461    2.1356    0.3059 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5406    2.0717    1.2856 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2729    1.6221   -0.4467 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8642   -0.1661    1.9763 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
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  2  0
  8 16  1  0
 16 17  2  0
 16 18  1  0
 18 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
  7 24  1  0
  9 25  1  0
  9 26  1  0
  9 27  1  0
 10 28  1  0
 10 29  1  0
 11 30  1  0
 11 31  1  0
 12 32  1  0
 12 33  1  0
 14 34  1  0
 14 35  1  0
 14 36  1  0
 18 37  1  0
 18 38  1  0
 19 39  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(+)-Umbellifolide	HMDB
4,5-dioxo-4,5-seco-11(13)-Eudesmen-12,8b-olide	HMDB
tetrahydro-6-Methyl-3-methylene-6-(4-oxopentyl)-2,5-(3H,4H)-benzofurandione, 9ci	HMDB
[3AR-(3aalpha,6alpha,7aalpha)]-tetrahydro-6-methyl-3-methylene-6-(4-oxopentyl)-2,5(3H,4H)-benzofurandione	HMDB

Chemical Formula

C₁₅H₂₀O₄

Average Molecular Weight

264.3169

Monoisotopic Molecular Weight

264.136159128

IUPAC Name

6-methyl-3-methylidene-6-(4-oxopentyl)-octahydro-1-benzofuran-2,5-dione

Traditional Name

6-methyl-3-methylidene-6-(4-oxopentyl)-tetrahydro-1-benzofuran-2,5-dione

CAS Registry Number

89026-40-4

SMILES

CC(=O)CCCC1(C)CC2OC(=O)C(=C)C2CC1=O

InChI Identifier

InChI=1S/C15H20O4/c1-9(16)5-4-6-15(3)8-12-11(7-13(15)17)10(2)14(18)19-12/h11-12H,2,4-8H2,1,3H3

InChI Key

MIRSLSRVCIOISZ-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as benzofurans. These are organic compounds containing a benzene ring fused to a furan. Furan is a five-membered aromatic ring with four carbon atoms and one oxygen atom.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzofurans

Sub Class

Not Available

Direct Parent

Benzofurans

Alternative Parents

Substituents

Benzofuran
Gamma butyrolactone
Tetrahydrofuran
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Carboxylic acid ester
Ketone
Lactone
Cyclic ketone
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Oxacycle
Carbonyl group
Organic oxygen compound
Organic oxide
Organooxygen 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: HMDB0038156)
Cytoplasm (HMDB: HMDB0038156)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0038156)

Source

Exogenous

Exogenous (HMDB: HMDB0038156)

Food

Food (HMDB: HMDB0038156)

Tea

Herb and spice

Herbs and Spices (FooDB: FOOD00866)

Endogenous

Plant

Plant (HMDB: HMDB0038156)

Process

Not Available

Role

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Emulsifier (HMDB: HMDB0038156)

Biological role

Nutrient (HMDB: HMDB0038156)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	113 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	13170 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.34 g/L	ALOGPS
logP	1.38	ALOGPS
logP	2.38	ChemAxon
logS	-2.9	ALOGPS
pKa (Strongest Acidic)	17.32	ChemAxon
pKa (Strongest Basic)	-6.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	60.44 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	69.64 m³·mol⁻¹	ChemAxon
Polarizability	28.09 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]+	162.552	31661259
DarkChem	[M-H]-	160.432	31661259
DeepCCS	[M+H]+	163.504	30932474
DeepCCS	[M-H]-	161.146	30932474
DeepCCS	[M-2H]-	194.083	30932474
DeepCCS	[M+Na]+	169.598	30932474
AllCCS	[M+H]+	163.5	32859911
AllCCS	[M+H-H2O]+	160.0	32859911
AllCCS	[M+NH4]+	166.8	32859911
AllCCS	[M+Na]+	167.7	32859911
AllCCS	[M-H]-	168.2	32859911
AllCCS	[M+Na-2H]-	168.4	32859911
AllCCS	[M+HCOO]-	168.9	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Umbellifolide	CC(=O)CCCC1(C)CC2OC(=O)C(=C)C2CC1=O	2877.6	Standard polar	33892256
Umbellifolide	CC(=O)CCCC1(C)CC2OC(=O)C(=C)C2CC1=O	2049.1	Standard non polar	33892256
Umbellifolide	CC(=O)CCCC1(C)CC2OC(=O)C(=C)C2CC1=O	2226.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Umbellifolide,1TMS,isomer #1	C=C1C(=O)OC2CC(C)(CCC=C(C)O[Si](C)(C)C)C(=O)CC12	2312.5	Semi standard non polar	33892256
Umbellifolide,1TMS,isomer #1	C=C1C(=O)OC2CC(C)(CCC=C(C)O[Si](C)(C)C)C(=O)CC12	2102.4	Standard non polar	33892256
Umbellifolide,1TMS,isomer #2	C=C1C(=O)OC2CC(C)(CCCC(C)=O)C(O[Si](C)(C)C)=CC12	2168.0	Semi standard non polar	33892256
Umbellifolide,1TMS,isomer #2	C=C1C(=O)OC2CC(C)(CCCC(C)=O)C(O[Si](C)(C)C)=CC12	1975.6	Standard non polar	33892256
Umbellifolide,1TMS,isomer #3	C=C(CCCC1(C)CC2OC(=O)C(=C)C2CC1=O)O[Si](C)(C)C	2241.1	Semi standard non polar	33892256
Umbellifolide,1TMS,isomer #3	C=C(CCCC1(C)CC2OC(=O)C(=C)C2CC1=O)O[Si](C)(C)C	2099.0	Standard non polar	33892256
Umbellifolide,2TMS,isomer #1	C=C1C(=O)OC2CC(C)(CCC=C(C)O[Si](C)(C)C)C(O[Si](C)(C)C)=CC12	2304.4	Semi standard non polar	33892256
Umbellifolide,2TMS,isomer #1	C=C1C(=O)OC2CC(C)(CCC=C(C)O[Si](C)(C)C)C(O[Si](C)(C)C)=CC12	2106.4	Standard non polar	33892256
Umbellifolide,2TMS,isomer #2	C=C(CCCC1(C)CC2OC(=O)C(=C)C2C=C1O[Si](C)(C)C)O[Si](C)(C)C	2235.9	Semi standard non polar	33892256
Umbellifolide,2TMS,isomer #2	C=C(CCCC1(C)CC2OC(=O)C(=C)C2C=C1O[Si](C)(C)C)O[Si](C)(C)C	2131.7	Standard non polar	33892256
Umbellifolide,1TBDMS,isomer #1	C=C1C(=O)OC2CC(C)(CCC=C(C)O[Si](C)(C)C(C)(C)C)C(=O)CC12	2546.2	Semi standard non polar	33892256
Umbellifolide,1TBDMS,isomer #1	C=C1C(=O)OC2CC(C)(CCC=C(C)O[Si](C)(C)C(C)(C)C)C(=O)CC12	2352.6	Standard non polar	33892256
Umbellifolide,1TBDMS,isomer #2	C=C1C(=O)OC2CC(C)(CCCC(C)=O)C(O[Si](C)(C)C(C)(C)C)=CC12	2419.7	Semi standard non polar	33892256
Umbellifolide,1TBDMS,isomer #2	C=C1C(=O)OC2CC(C)(CCCC(C)=O)C(O[Si](C)(C)C(C)(C)C)=CC12	2168.2	Standard non polar	33892256
Umbellifolide,1TBDMS,isomer #3	C=C(CCCC1(C)CC2OC(=O)C(=C)C2CC1=O)O[Si](C)(C)C(C)(C)C	2468.0	Semi standard non polar	33892256
Umbellifolide,1TBDMS,isomer #3	C=C(CCCC1(C)CC2OC(=O)C(=C)C2CC1=O)O[Si](C)(C)C(C)(C)C	2337.6	Standard non polar	33892256
Umbellifolide,2TBDMS,isomer #1	C=C1C(=O)OC2CC(C)(CCC=C(C)O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=CC12	2793.6	Semi standard non polar	33892256
Umbellifolide,2TBDMS,isomer #1	C=C1C(=O)OC2CC(C)(CCC=C(C)O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=CC12	2486.7	Standard non polar	33892256
Umbellifolide,2TBDMS,isomer #2	C=C(CCCC1(C)CC2OC(=O)C(=C)C2C=C1O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	2719.8	Semi standard non polar	33892256
Umbellifolide,2TBDMS,isomer #2	C=C(CCCC1(C)CC2OC(=O)C(=C)C2C=C1O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	2484.5	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Umbellifolide GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-8890000000-11e581a4b66c2cd183d2	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Umbellifolide GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Umbellifolide 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 - Umbellifolide 10V, Positive-QTOF	splash10-014j-0290000000-5ba86cd75f89102831e9	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Umbellifolide 20V, Positive-QTOF	splash10-029b-3960000000-2e488f1690fc64692976	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Umbellifolide 40V, Positive-QTOF	splash10-0f6x-9400000000-cb45b2b42aa6c30eb923	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Umbellifolide 10V, Negative-QTOF	splash10-03di-0090000000-dd296c1b09fee60a3098	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Umbellifolide 20V, Negative-QTOF	splash10-03xr-2190000000-1d41a805f9b883be9093	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Umbellifolide 40V, Negative-QTOF	splash10-0pbi-9640000000-fb5f6e88c3d0b772ba62	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Umbellifolide 10V, Positive-QTOF	splash10-0ftb-0190000000-9538652d3676249872a5	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Umbellifolide 20V, Positive-QTOF	splash10-004i-1940000000-c5a8596fe39f5a9451af	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Umbellifolide 40V, Positive-QTOF	splash10-0adl-1900000000-b1cd67a17248899a128e	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Umbellifolide 10V, Negative-QTOF	splash10-03di-0090000000-16d43704d08f3756e03a	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Umbellifolide 20V, Negative-QTOF	splash10-03di-1290000000-feef4a1ab5e8dedc625b	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Umbellifolide 40V, Negative-QTOF	splash10-00or-6920000000-91c5e3a41e06f1c9161e	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

FDB017385

KNApSAcK ID

C00013211

Chemspider ID

35014521

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

13889981

PDB ID

Not Available

ChEBI ID

174483

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1866071

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 Umbellifolide (HMDB0038156)

MOL for HMDB0038156 (Umbellifolide)

3D MOL for HMDB0038156 (Umbellifolide)

3D SDF for HMDB0038156 (Umbellifolide)

3D-SDF for HMDB0038156 (Umbellifolide)

PDB for HMDB0038156 (Umbellifolide)

3D PDB for HMDB0038156 (Umbellifolide)

SMILES for HMDB0038156 (Umbellifolide)

INCHI for HMDB0038156 (Umbellifolide)

Structure for HMDB0038156 (Umbellifolide)

3D Structure for HMDB0038156 (Umbellifolide)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra