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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 18:39:25 UTC

Update Date

2022-03-07 02:53:53 UTC

HMDB ID

HMDB0033884

Secondary Accession Numbers

HMDB33884

Metabolite Identification

Common Name

Gravolenic acid

Description

Gravolenic acid, also known as gravolenate, belongs to the class of organic compounds known as coumaric acids and derivatives. These are aromatic compounds containing Aromatic compounds containing a cinnamic acid moiety (or a derivative thereof) hydroxylated at the C2 (ortho-), C3 (meta-), or C4 (para-) carbon atom of the benzene ring. Gravolenic acid has been detected, but not quantified in, herbs and spices. This could make gravolenic acid a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Gravolenic acid.

Structure

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

HMDB0033884
     RDKit          3D
Gravolenic acid
 36 37  0  0  0  0  0  0  0  0999 V2000
   -3.4524    0.6423   -0.9407 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0824    0.1348    0.4209 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3117    1.1943    1.4775 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8996   -0.9527    0.7298 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6540   -0.3524    0.4908 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3834   -1.3581   -0.6017 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1010   -1.1654   -0.8055 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0602   -1.9955   -1.3746 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6690   -3.2369   -1.8566 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3592   -1.5610   -1.4408 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3276   -2.3932   -2.0127 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7236   -0.3063   -0.9474 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7821    0.5029   -0.3873 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0113    1.7538    0.2613 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0156    2.1165    0.9535 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1708    1.3894    1.2925 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4498    0.2330    1.0420 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1710    2.0754    2.0316 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4287    0.0655   -0.3132 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7218    0.6722    0.1937 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8208   -0.2303   -1.5284 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3262    1.3251   -0.8203 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6271    1.1381   -1.4705 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0213    2.2028    1.0995 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7374    0.9787    2.4055 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3985    1.2641    1.7288 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4768   -1.3936    1.5337 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4462   -0.7309    1.4918 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9212   -1.0476   -1.5107 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5899   -2.3982   -0.3014 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2827   -3.5136   -1.7892 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0643   -3.2946   -2.3668 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7524   -0.0214   -1.1169 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1992    2.5518    0.1525 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9701    3.1954    1.3608 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8977    2.5158    2.9185 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  2  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 10 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
 13 19  2  0
 19 20  1  0
 20  5  1  0
 19  7  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  3 24  1  0
  3 25  1  0
  3 26  1  0
  4 27  1  0
  5 28  1  0
  6 29  1  0
  6 30  1  0
  9 31  1  0
 11 32  1  0
 12 33  1  0
 14 34  1  0
 15 35  1  0
 18 36  1  0
M  END


  Mrv0541 05061307252D          

 20 21  0  0  0  0            999 V2000
   -0.3551    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4699   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7798   -0.2549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2949    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7079    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4699    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7079   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7079    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4223    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4699    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7798    1.0799    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  2  0  0  0  0
  7  3  1  0  0  0  0
  7  5  1  0  0  0  0
  8  6  1  0  0  0  0
  9  5  2  0  0  0  0
 10  6  1  0  0  0  0
 11  4  1  0  0  0  0
 12  8  2  0  0  0  0
 12  9  1  0  0  0  0
 13  7  2  0  0  0  0
 13  8  1  0  0  0  0
 14  1  1  0  0  0  0
 14  2  1  0  0  0  0
 14 10  1  0  0  0  0
 15  9  1  0  0  0  0
 16 11  2  0  0  0  0
 17 11  1  0  0  0  0
 18 12  1  0  0  0  0
 19 14  1  0  0  0  0
 20 10  1  0  0  0  0
 20 13  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0033884

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(C)(O)C1CC2=C(O)C(O)=CC(\C=C/C(O)=O)=C2O1

> <INCHI_IDENTIFIER>
InChI=1S/C14H16O6/c1-14(2,19)10-6-8-12(18)9(15)5-7(13(8)20-10)3-4-11(16)17/h3-5,10,15,18-19H,6H2,1-2H3,(H,16,17)/b4-3-

> <INCHI_KEY>
DABSIZUNYJTFDJ-ARJAWSKDSA-N

> <FORMULA>
C14H16O6

> <MOLECULAR_WEIGHT>
280.2732

> <EXACT_MASS>
280.094688244

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
28.08162274229064

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2Z)-3-[4,5-dihydroxy-2-(2-hydroxypropan-2-yl)-2,3-dihydro-1-benzofuran-7-yl]prop-2-enoic acid

> <ALOGPS_LOGP>
1.40

> <JCHEM_LOGP>
1.477989608333333

> <ALOGPS_LOGS>
-2.78

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
9.666455629325172

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.7118754021700973

> <JCHEM_PKA_STRONGEST_BASIC>
-3.10645466047717

> <JCHEM_POLAR_SURFACE_AREA>
107.22000000000001

> <JCHEM_REFRACTIVITY>
71.81400000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.68e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2Z)-3-[4,5-dihydroxy-2-(2-hydroxypropan-2-yl)-2,3-dihydro-1-benzofuran-7-yl]prop-2-enoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0033884
     RDKit          3D
Gravolenic acid
 36 37  0  0  0  0  0  0  0  0999 V2000
   -3.4524    0.6423   -0.9407 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0824    0.1348    0.4209 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3117    1.1943    1.4775 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8996   -0.9527    0.7298 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6540   -0.3524    0.4908 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3834   -1.3581   -0.6017 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1010   -1.1654   -0.8055 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0602   -1.9955   -1.3746 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6690   -3.2369   -1.8566 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3592   -1.5610   -1.4408 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3276   -2.3932   -2.0127 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7236   -0.3063   -0.9474 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7821    0.5029   -0.3873 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0113    1.7538    0.2613 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0156    2.1165    0.9535 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1708    1.3894    1.2925 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4498    0.2330    1.0420 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1710    2.0754    2.0316 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4287    0.0655   -0.3132 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7218    0.6722    0.1937 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8208   -0.2303   -1.5284 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3262    1.3251   -0.8203 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6271    1.1381   -1.4705 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0213    2.2028    1.0995 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7374    0.9787    2.4055 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3985    1.2641    1.7288 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4768   -1.3936    1.5337 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4462   -0.7309    1.4918 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9212   -1.0476   -1.5107 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5899   -2.3982   -0.3014 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2827   -3.5136   -1.7892 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0643   -3.2946   -2.3668 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7524   -0.0214   -1.1169 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1992    2.5518    0.1525 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9701    3.1954    1.3608 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8977    2.5158    2.9185 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  2  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 10 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
 13 19  2  0
 19 20  1  0
 20  5  1  0
 19  7  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  3 24  1  0
  3 25  1  0
  3 26  1  0
  4 27  1  0
  5 28  1  0
  6 29  1  0
  6 30  1  0
  9 31  1  0
 11 32  1  0
 12 33  1  0
 14 34  1  0
 15 35  1  0
 18 36  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      -0.663   0.770   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.877  -0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.121   3.850   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.454   4.620   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.454   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.322  -0.476   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.121   2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.787   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.454   0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.417   0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.788   3.850   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.121  -0.770   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.787   1.540   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.877   0.770   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       8.788  -0.770   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       8.788   2.310   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0      10.122   4.620   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       6.121  -2.310   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       0.877   2.310   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       3.322   2.016   0.000  0.00  0.00           O+0
CONECT    1   14                                                            
CONECT    2   14                                                            
CONECT    3    4    7                                                       
CONECT    4    3   11                                                       
CONECT    5    7    9                                                       
CONECT    6    8   10                                                       
CONECT    7    3    5   13                                                  
CONECT    8    6   12   13                                                  
CONECT    9    5   12   15                                                  
CONECT   10    6   14   20                                                  
CONECT   11    4   16   17                                                  
CONECT   12    8    9   18                                                  
CONECT   13    7    8   20                                                  
CONECT   14    1    2   10   19                                             
CONECT   15    9                                                            
CONECT   16   11                                                            
CONECT   17   11                                                            
CONECT   18   12                                                            
CONECT   19   14                                                            
CONECT   20   10   13                                                       
MASTER        0    0    0    0    0    0    0    0   20    0   42    0
END

COMPND    HMDB0033884
HETATM    1  C1  UNL     1      -3.452   0.642  -0.941  1.00  0.00           C  
HETATM    2  C2  UNL     1      -3.082   0.135   0.421  1.00  0.00           C  
HETATM    3  C3  UNL     1      -3.312   1.194   1.477  1.00  0.00           C  
HETATM    4  O1  UNL     1      -3.900  -0.953   0.730  1.00  0.00           O  
HETATM    5  C4  UNL     1      -1.654  -0.352   0.491  1.00  0.00           C  
HETATM    6  C5  UNL     1      -1.383  -1.358  -0.602  1.00  0.00           C  
HETATM    7  C6  UNL     1       0.101  -1.165  -0.806  1.00  0.00           C  
HETATM    8  C7  UNL     1       1.060  -1.995  -1.375  1.00  0.00           C  
HETATM    9  O2  UNL     1       0.669  -3.237  -1.857  1.00  0.00           O  
HETATM   10  C8  UNL     1       2.359  -1.561  -1.441  1.00  0.00           C  
HETATM   11  O3  UNL     1       3.328  -2.393  -2.013  1.00  0.00           O  
HETATM   12  C9  UNL     1       2.724  -0.306  -0.947  1.00  0.00           C  
HETATM   13  C10 UNL     1       1.782   0.503  -0.387  1.00  0.00           C  
HETATM   14  C11 UNL     1       2.011   1.754   0.261  1.00  0.00           C  
HETATM   15  C12 UNL     1       3.016   2.116   0.953  1.00  0.00           C  
HETATM   16  C13 UNL     1       4.171   1.389   1.293  1.00  0.00           C  
HETATM   17  O4  UNL     1       4.450   0.233   1.042  1.00  0.00           O  
HETATM   18  O5  UNL     1       5.171   2.075   2.032  1.00  0.00           O  
HETATM   19  C14 UNL     1       0.429   0.065  -0.313  1.00  0.00           C  
HETATM   20  O6  UNL     1      -0.722   0.672   0.194  1.00  0.00           O  
HETATM   21  H1  UNL     1      -3.821  -0.230  -1.528  1.00  0.00           H  
HETATM   22  H2  UNL     1      -4.326   1.325  -0.820  1.00  0.00           H  
HETATM   23  H3  UNL     1      -2.627   1.138  -1.471  1.00  0.00           H  
HETATM   24  H4  UNL     1      -3.021   2.203   1.100  1.00  0.00           H  
HETATM   25  H5  UNL     1      -2.737   0.979   2.405  1.00  0.00           H  
HETATM   26  H6  UNL     1      -4.398   1.264   1.729  1.00  0.00           H  
HETATM   27  H7  UNL     1      -3.477  -1.394   1.534  1.00  0.00           H  
HETATM   28  H8  UNL     1      -1.446  -0.731   1.492  1.00  0.00           H  
HETATM   29  H9  UNL     1      -1.921  -1.048  -1.511  1.00  0.00           H  
HETATM   30  H10 UNL     1      -1.590  -2.398  -0.301  1.00  0.00           H  
HETATM   31  H11 UNL     1      -0.283  -3.514  -1.789  1.00  0.00           H  
HETATM   32  H12 UNL     1       3.064  -3.295  -2.367  1.00  0.00           H  
HETATM   33  H13 UNL     1       3.752  -0.021  -1.117  1.00  0.00           H  
HETATM   34  H14 UNL     1       1.199   2.552   0.152  1.00  0.00           H  
HETATM   35  H15 UNL     1       2.970   3.195   1.361  1.00  0.00           H  
HETATM   36  H16 UNL     1       4.898   2.516   2.918  1.00  0.00           H  
CONECT    1    2   21   22   23
CONECT    2    3    4    5
CONECT    3   24   25   26
CONECT    4   27
CONECT    5    6   20   28
CONECT    6    7   29   30
CONECT    7    8    8   19
CONECT    8    9   10
CONECT    9   31
CONECT   10   11   12   12
CONECT   11   32
CONECT   12   13   33
CONECT   13   14   19   19
CONECT   14   15   15   34
CONECT   15   16   35
CONECT   16   17   17   18
CONECT   18   36
CONECT   19   20
END

HMDB0033884
     RDKit          3D
Gravolenic acid
 36 37  0  0  0  0  0  0  0  0999 V2000
   -3.4524    0.6423   -0.9407 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0824    0.1348    0.4209 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3117    1.1943    1.4775 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8996   -0.9527    0.7298 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6540   -0.3524    0.4908 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3834   -1.3581   -0.6017 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1010   -1.1654   -0.8055 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0602   -1.9955   -1.3746 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6690   -3.2369   -1.8566 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3592   -1.5610   -1.4408 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3276   -2.3932   -2.0127 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7236   -0.3063   -0.9474 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7821    0.5029   -0.3873 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0113    1.7538    0.2613 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0156    2.1165    0.9535 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1708    1.3894    1.2925 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4498    0.2330    1.0420 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1710    2.0754    2.0316 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4287    0.0655   -0.3132 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7218    0.6722    0.1937 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8208   -0.2303   -1.5284 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3262    1.3251   -0.8203 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6271    1.1381   -1.4705 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0213    2.2028    1.0995 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7374    0.9787    2.4055 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3985    1.2641    1.7288 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4768   -1.3936    1.5337 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4462   -0.7309    1.4918 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9212   -1.0476   -1.5107 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5899   -2.3982   -0.3014 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2827   -3.5136   -1.7892 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0643   -3.2946   -2.3668 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7524   -0.0214   -1.1169 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1992    2.5518    0.1525 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9701    3.1954    1.3608 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8977    2.5158    2.9185 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  2  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 10 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
 13 19  2  0
 19 20  1  0
 20  5  1  0
 19  7  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  3 24  1  0
  3 25  1  0
  3 26  1  0
  4 27  1  0
  5 28  1  0
  6 29  1  0
  6 30  1  0
  9 31  1  0
 11 32  1  0
 12 33  1  0
 14 34  1  0
 15 35  1  0
 18 36  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Gravolenate	Generator
(2Z)-3-[4,5-Dihydroxy-2-(2-hydroxypropan-2-yl)-2,3-dihydro-1-benzofuran-7-yl]prop-2-enoate	HMDB

Chemical Formula

C₁₄H₁₆O₆

Average Molecular Weight

280.2732

Monoisotopic Molecular Weight

280.094688244

IUPAC Name

(2Z)-3-[4,5-dihydroxy-2-(2-hydroxypropan-2-yl)-2,3-dihydro-1-benzofuran-7-yl]prop-2-enoic acid

Traditional Name

(2Z)-3-[4,5-dihydroxy-2-(2-hydroxypropan-2-yl)-2,3-dihydro-1-benzofuran-7-yl]prop-2-enoic acid

CAS Registry Number

13781-46-9

SMILES

CC(C)(O)C1CC2=C(O)C(O)=CC(\C=C/C(O)=O)=C2O1

InChI Identifier

InChI=1S/C14H16O6/c1-14(2,19)10-6-8-12(18)9(15)5-7(13(8)20-10)3-4-11(16)17/h3-5,10,15,18-19H,6H2,1-2H3,(H,16,17)/b4-3-

InChI Key

DABSIZUNYJTFDJ-ARJAWSKDSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as coumaric acids and derivatives. These are aromatic compounds containing Aromatic compounds containing a cinnamic acid moiety (or a derivative thereof) hydroxylated at the C2 (ortho-), C3 (meta-), or C4 (para-) carbon atom of the benzene ring.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Cinnamic acids and derivatives

Sub Class

Hydroxycinnamic acids and derivatives

Direct Parent

Coumaric acids and derivatives

Alternative Parents

Substituents

Coumaric acid or derivatives
Coumaran
Styrene
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Benzenoid
Tertiary alcohol
Carboxylic acid derivative
Carboxylic acid
Ether
Monocarboxylic acid or derivatives
Oxacycle
Organoheterocyclic compound
Organic oxide
Carbonyl group
Organooxygen compound
Hydrocarbon derivative
Alcohol
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0033884)
Cytoplasm (HMDB: HMDB0033884)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0033884)

Source

Exogenous

Food

Food (HMDB: HMDB0033884)

Herb and spice

Herbs and Spices (FooDB: FOOD00866)

Endogenous

Plant

Plant (HMDB: HMDB0033884)

Not Available

Nutrient (HMDB: HMDB0033884)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	194 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	28170 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	0.47 g/L	ALOGPS
logP	1.4	ALOGPS
logP	1.48	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Acidic)	3.71	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	107.22 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	71.81 m³·mol⁻¹	ChemAxon
Polarizability	28.08 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
DeepCCS	[M+H]+	163.281	30932474
DeepCCS	[M-H]-	160.923	30932474
DeepCCS	[M-2H]-	193.81	30932474
DeepCCS	[M+Na]+	169.375	30932474
AllCCS	[M+H]+	163.8	32859911
AllCCS	[M+H-H2O]+	160.3	32859911
AllCCS	[M+NH4]+	167.1	32859911
AllCCS	[M+Na]+	168.0	32859911
AllCCS	[M-H]-	165.3	32859911
AllCCS	[M+Na-2H]-	165.2	32859911
AllCCS	[M+HCOO]-	165.3	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Gravolenic acid	CC(C)(O)C1CC2=C(O)C(O)=CC(\C=C/C(O)=O)=C2O1	4404.0	Standard polar	33892256
Gravolenic acid	CC(C)(O)C1CC2=C(O)C(O)=CC(\C=C/C(O)=O)=C2O1	2508.1	Standard non polar	33892256
Gravolenic acid	CC(C)(O)C1CC2=C(O)C(O)=CC(\C=C/C(O)=O)=C2O1	2634.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Gravolenic acid,1TMS,isomer #1	CC(C)(O[Si](C)(C)C)C1CC2=C(O)C(O)=CC(/C=C\C(=O)O)=C2O1	2669.8	Semi standard non polar	33892256
Gravolenic acid,1TMS,isomer #2	CC(C)(O)C1CC2=C(O[Si](C)(C)C)C(O)=CC(/C=C\C(=O)O)=C2O1	2592.0	Semi standard non polar	33892256
Gravolenic acid,1TMS,isomer #3	CC(C)(O)C1CC2=C(O)C(O[Si](C)(C)C)=CC(/C=C\C(=O)O)=C2O1	2561.3	Semi standard non polar	33892256
Gravolenic acid,1TMS,isomer #4	CC(C)(O)C1CC2=C(O)C(O)=CC(/C=C\C(=O)O[Si](C)(C)C)=C2O1	2637.1	Semi standard non polar	33892256
Gravolenic acid,2TMS,isomer #1	CC(C)(O[Si](C)(C)C)C1CC2=C(O[Si](C)(C)C)C(O)=CC(/C=C\C(=O)O)=C2O1	2614.5	Semi standard non polar	33892256
Gravolenic acid,2TMS,isomer #2	CC(C)(O[Si](C)(C)C)C1CC2=C(O)C(O[Si](C)(C)C)=CC(/C=C\C(=O)O)=C2O1	2581.7	Semi standard non polar	33892256
Gravolenic acid,2TMS,isomer #3	CC(C)(O[Si](C)(C)C)C1CC2=C(O)C(O)=CC(/C=C\C(=O)O[Si](C)(C)C)=C2O1	2641.7	Semi standard non polar	33892256
Gravolenic acid,2TMS,isomer #4	CC(C)(O)C1CC2=C(O1)C(/C=C\C(=O)O)=CC(O[Si](C)(C)C)=C2O[Si](C)(C)C	2549.7	Semi standard non polar	33892256
Gravolenic acid,2TMS,isomer #5	CC(C)(O)C1CC2=C(O[Si](C)(C)C)C(O)=CC(/C=C\C(=O)O[Si](C)(C)C)=C2O1	2555.9	Semi standard non polar	33892256
Gravolenic acid,2TMS,isomer #6	CC(C)(O)C1CC2=C(O)C(O[Si](C)(C)C)=CC(/C=C\C(=O)O[Si](C)(C)C)=C2O1	2541.9	Semi standard non polar	33892256
Gravolenic acid,3TMS,isomer #1	CC(C)(O[Si](C)(C)C)C1CC2=C(O1)C(/C=C\C(=O)O)=CC(O[Si](C)(C)C)=C2O[Si](C)(C)C	2578.2	Semi standard non polar	33892256
Gravolenic acid,3TMS,isomer #2	CC(C)(O[Si](C)(C)C)C1CC2=C(O[Si](C)(C)C)C(O)=CC(/C=C\C(=O)O[Si](C)(C)C)=C2O1	2593.8	Semi standard non polar	33892256
Gravolenic acid,3TMS,isomer #3	CC(C)(O[Si](C)(C)C)C1CC2=C(O)C(O[Si](C)(C)C)=CC(/C=C\C(=O)O[Si](C)(C)C)=C2O1	2576.1	Semi standard non polar	33892256
Gravolenic acid,3TMS,isomer #4	CC(C)(O)C1CC2=C(O1)C(/C=C\C(=O)O[Si](C)(C)C)=CC(O[Si](C)(C)C)=C2O[Si](C)(C)C	2554.5	Semi standard non polar	33892256
Gravolenic acid,4TMS,isomer #1	CC(C)(O[Si](C)(C)C)C1CC2=C(O1)C(/C=C\C(=O)O[Si](C)(C)C)=CC(O[Si](C)(C)C)=C2O[Si](C)(C)C	2597.9	Semi standard non polar	33892256
Gravolenic acid,1TBDMS,isomer #1	CC(C)(O[Si](C)(C)C(C)(C)C)C1CC2=C(O)C(O)=CC(/C=C\C(=O)O)=C2O1	2930.4	Semi standard non polar	33892256
Gravolenic acid,1TBDMS,isomer #2	CC(C)(O)C1CC2=C(O[Si](C)(C)C(C)(C)C)C(O)=CC(/C=C\C(=O)O)=C2O1	2850.6	Semi standard non polar	33892256
Gravolenic acid,1TBDMS,isomer #3	CC(C)(O)C1CC2=C(O)C(O[Si](C)(C)C(C)(C)C)=CC(/C=C\C(=O)O)=C2O1	2816.6	Semi standard non polar	33892256
Gravolenic acid,1TBDMS,isomer #4	CC(C)(O)C1CC2=C(O)C(O)=CC(/C=C\C(=O)O[Si](C)(C)C(C)(C)C)=C2O1	2909.1	Semi standard non polar	33892256
Gravolenic acid,2TBDMS,isomer #1	CC(C)(O[Si](C)(C)C(C)(C)C)C1CC2=C(O[Si](C)(C)C(C)(C)C)C(O)=CC(/C=C\C(=O)O)=C2O1	3127.2	Semi standard non polar	33892256
Gravolenic acid,2TBDMS,isomer #2	CC(C)(O[Si](C)(C)C(C)(C)C)C1CC2=C(O)C(O[Si](C)(C)C(C)(C)C)=CC(/C=C\C(=O)O)=C2O1	3079.6	Semi standard non polar	33892256
Gravolenic acid,2TBDMS,isomer #3	CC(C)(O[Si](C)(C)C(C)(C)C)C1CC2=C(O)C(O)=CC(/C=C\C(=O)O[Si](C)(C)C(C)(C)C)=C2O1	3150.7	Semi standard non polar	33892256
Gravolenic acid,2TBDMS,isomer #4	CC(C)(O)C1CC2=C(O1)C(/C=C\C(=O)O)=CC(O[Si](C)(C)C(C)(C)C)=C2O[Si](C)(C)C(C)(C)C	3046.5	Semi standard non polar	33892256
Gravolenic acid,2TBDMS,isomer #5	CC(C)(O)C1CC2=C(O[Si](C)(C)C(C)(C)C)C(O)=CC(/C=C\C(=O)O[Si](C)(C)C(C)(C)C)=C2O1	3074.9	Semi standard non polar	33892256
Gravolenic acid,2TBDMS,isomer #6	CC(C)(O)C1CC2=C(O)C(O[Si](C)(C)C(C)(C)C)=CC(/C=C\C(=O)O[Si](C)(C)C(C)(C)C)=C2O1	3048.3	Semi standard non polar	33892256
Gravolenic acid,3TBDMS,isomer #1	CC(C)(O[Si](C)(C)C(C)(C)C)C1CC2=C(O1)C(/C=C\C(=O)O)=CC(O[Si](C)(C)C(C)(C)C)=C2O[Si](C)(C)C(C)(C)C	3305.5	Semi standard non polar	33892256
Gravolenic acid,3TBDMS,isomer #2	CC(C)(O[Si](C)(C)C(C)(C)C)C1CC2=C(O[Si](C)(C)C(C)(C)C)C(O)=CC(/C=C\C(=O)O[Si](C)(C)C(C)(C)C)=C2O1	3312.1	Semi standard non polar	33892256
Gravolenic acid,3TBDMS,isomer #3	CC(C)(O[Si](C)(C)C(C)(C)C)C1CC2=C(O)C(O[Si](C)(C)C(C)(C)C)=CC(/C=C\C(=O)O[Si](C)(C)C(C)(C)C)=C2O1	3298.4	Semi standard non polar	33892256
Gravolenic acid,3TBDMS,isomer #4	CC(C)(O)C1CC2=C(O1)C(/C=C\C(=O)O[Si](C)(C)C(C)(C)C)=CC(O[Si](C)(C)C(C)(C)C)=C2O[Si](C)(C)C(C)(C)C	3260.8	Semi standard non polar	33892256
Gravolenic acid,4TBDMS,isomer #1	CC(C)(O[Si](C)(C)C(C)(C)C)C1CC2=C(O1)C(/C=C\C(=O)O[Si](C)(C)C(C)(C)C)=CC(O[Si](C)(C)C(C)(C)C)=C2O[Si](C)(C)C(C)(C)C	3475.7	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Gravolenic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-0bt9-7190000000-73c954728f9772071d7a	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Gravolenic acid GC-MS (4 TMS) - 70eV, Positive	splash10-0ll0-7590540000-6a00bc06d5a6a29f9804	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Gravolenic acid 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 - Gravolenic acid 10V, Positive-QTOF	splash10-03e9-0090000000-3bc89561c66281086000	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Gravolenic acid 20V, Positive-QTOF	splash10-0jca-1090000000-eff4b3e0910441ef70c4	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Gravolenic acid 40V, Positive-QTOF	splash10-03di-2920000000-e42346980ae05e797f8f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Gravolenic acid 10V, Negative-QTOF	splash10-004i-0090000000-c469059fe0dfb8bba15c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Gravolenic acid 20V, Negative-QTOF	splash10-01t9-1090000000-e8d0adb8eaea8699e3eb	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Gravolenic acid 40V, Negative-QTOF	splash10-004i-2920000000-d6157fc2a55627231cb2	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Gravolenic acid 10V, Negative-QTOF	splash10-014i-0090000000-6d8947d011a9805db7bc	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Gravolenic acid 20V, Negative-QTOF	splash10-00pi-0490000000-496d84f9f5dcb2a8ba45	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Gravolenic acid 40V, Negative-QTOF	splash10-0002-3930000000-fe0eb7b214e909d26dde	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Gravolenic acid 10V, Positive-QTOF	splash10-01q9-0090000000-53104a6b3bda8649e49d	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Gravolenic acid 20V, Positive-QTOF	splash10-02ai-0090000000-a4703ad462942de65373	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Gravolenic acid 40V, Positive-QTOF	splash10-052b-1940000000-a08ec4840b2eb4185262	2021-09-23	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

FDB012077

KNApSAcK ID

Not Available

Chemspider ID

35013671

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

131751501

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1839081

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 Gravolenic acid (HMDB0033884)

MOL for HMDB0033884 (Gravolenic acid)

3D MOL for HMDB0033884 (Gravolenic acid)

3D SDF for HMDB0033884 (Gravolenic acid)

3D-SDF for HMDB0033884 (Gravolenic acid)

PDB for HMDB0033884 (Gravolenic acid)

3D PDB for HMDB0033884 (Gravolenic acid)

SMILES for HMDB0033884 (Gravolenic acid)

INCHI for HMDB0033884 (Gravolenic acid)

Structure for HMDB0033884 (Gravolenic acid)

3D Structure for HMDB0033884 (Gravolenic acid)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra