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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:31:00 UTC

Update Date

2022-03-07 02:52:12 UTC

HMDB ID

HMDB0029535

Secondary Accession Numbers

HMDB29535

Metabolite Identification

Common Name

Grevilline A

Description

Grevilline A belongs to the class of organic compounds known as dihydropyranones. Dihydropyranones are compounds containing a hydrogenated pyran ring which bears a ketone, and contains one double bond. Based on a literature review a significant number of articles have been published on Grevilline A.

Structure

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

HMDB0029535
     RDKit          3D
Grevilline A
 36 38  0  0  0  0  0  0  0  0999 V2000
   -1.7109   -4.6807    0.5761 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1185   -3.5676    0.4173 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2644   -3.4831    0.3481 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8823   -2.2425    0.1741 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1993   -2.1200    0.0991 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8886   -0.8596   -0.0657 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6065   -0.6073   -1.1916 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3264    0.5633   -1.3679 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3212    1.5016   -0.3775 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0288    2.7159   -0.4852 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5962    1.2472    0.7644 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8782    0.0834    0.9412 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0178   -1.0763    0.0705 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4880    0.0715   -0.0909 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4462   -1.1913    0.1469 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2455    0.0198    0.0469 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2407    0.3317    0.9523 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0112    1.4694    0.8166 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8236    2.3578   -0.2411 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6060    3.4970   -0.3681 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8260    2.0390   -1.1421 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0533    0.8891   -0.9958 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9762   -2.3928    0.3136 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3716   -2.4478    0.3799 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7488   -3.0723    0.1773 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6572   -1.3197   -2.0333 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8694    0.7201   -2.2610 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9889    3.3573    0.2640 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6084    2.0123    1.5455 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3385   -0.0471    1.8769 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3979   -0.3434    1.7757 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8020    1.7364    1.5164 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3723    4.3783    0.0199 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6625    2.7185   -1.9736 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2712    0.6809   -1.7408 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7733   -2.9389    1.1579 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
  9 11  1  0
 11 12  2  0
  4 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 19 21  1  0
 21 22  2  0
 15 23  2  0
 23 24  1  0
 23  2  1  0
 12  6  1  0
 22 16  1  0
  5 25  1  0
  7 26  1  0
  8 27  1  0
 10 28  1  0
 11 29  1  0
 12 30  1  0
 17 31  1  0
 18 32  1  0
 20 33  1  0
 21 34  1  0
 22 35  1  0
 24 36  1  0
M  END

  Mrv0541 05061304482D          

 24 26  0  0  0  0            999 V2000
    0.0000   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7158   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -5.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  1  1  0  0  0  0
  6  2  2  0  0  0  0
  7  3  1  0  0  0  0
  8  4  2  0  0  0  0
 10  1  2  0  0  0  0
 10  2  1  0  0  0  0
 10  9  1  0  0  0  0
 11  3  2  0  0  0  0
 11  4  1  0  0  0  0
 12  5  2  0  0  0  0
 12  6  1  0  0  0  0
 13  7  2  0  0  0  0
 13  8  1  0  0  0  0
 14  9  2  0  0  0  0
 15 11  1  0  0  0  0
 16 14  1  0  0  0  0
 16 15  1  0  0  0  0
 17 15  2  0  0  0  0
 18 17  1  0  0  0  0
 19 12  1  0  0  0  0
 20 13  1  0  0  0  0
 21 16  2  0  0  0  0
 22 17  1  0  0  0  0
 23 18  2  0  0  0  0
 24 14  1  0  0  0  0
 24 18  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0029535

> <DATABASE_NAME>
hmdb

> <SMILES>
OC1=CC=C(\C=C2\OC(=O)C(O)=C(C2=O)C2=CC=C(O)C=C2)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C18H12O6/c19-12-5-1-10(2-6-12)9-14-16(21)15(17(22)18(23)24-14)11-3-7-13(20)8-4-11/h1-9,19-20,22H/b14-9+

> <INCHI_KEY>
PZEIKFYZAURRNF-NTEUORMPSA-N

> <FORMULA>
C18H12O6

> <MOLECULAR_WEIGHT>
324.2843

> <EXACT_MASS>
324.063388116

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
31.702840148113182

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(6E)-3-hydroxy-4-(4-hydroxyphenyl)-6-[(4-hydroxyphenyl)methylidene]-5,6-dihydro-2H-pyran-2,5-dione

> <ALOGPS_LOGP>
2.66

> <JCHEM_LOGP>
3.0392902986666663

> <ALOGPS_LOGS>
-3.59

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.792801261151785

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.911367673666399

> <JCHEM_PKA_STRONGEST_BASIC>
-3.593485873080395

> <JCHEM_POLAR_SURFACE_AREA>
104.06000000000002

> <JCHEM_REFRACTIVITY>
87.43079999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.33e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(6E)-3-hydroxy-4-(4-hydroxyphenyl)-6-[(4-hydroxyphenyl)methylidene]pyran-2,5-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0029535
     RDKit          3D
Grevilline A
 36 38  0  0  0  0  0  0  0  0999 V2000
   -1.7109   -4.6807    0.5761 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1185   -3.5676    0.4173 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2644   -3.4831    0.3481 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8823   -2.2425    0.1741 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1993   -2.1200    0.0991 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8886   -0.8596   -0.0657 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6065   -0.6073   -1.1916 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3264    0.5633   -1.3679 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3212    1.5016   -0.3775 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0288    2.7159   -0.4852 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5962    1.2472    0.7644 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8782    0.0834    0.9412 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0178   -1.0763    0.0705 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4880    0.0715   -0.0909 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4462   -1.1913    0.1469 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2455    0.0198    0.0469 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2407    0.3317    0.9523 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0112    1.4694    0.8166 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8236    2.3578   -0.2411 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6060    3.4970   -0.3681 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8260    2.0390   -1.1421 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0533    0.8891   -0.9958 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9762   -2.3928    0.3136 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3716   -2.4478    0.3799 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7488   -3.0723    0.1773 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6572   -1.3197   -2.0333 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8694    0.7201   -2.2610 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9889    3.3573    0.2640 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6084    2.0123    1.5455 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3385   -0.0471    1.8769 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3979   -0.3434    1.7757 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8020    1.7364    1.5164 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3723    4.3783    0.0199 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6625    2.7185   -1.9736 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2712    0.6809   -1.7408 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7733   -2.9389    1.1579 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
  9 11  1  0
 11 12  2  0
  4 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 19 21  1  0
 21 22  2  0
 15 23  2  0
 23 24  1  0
 23  2  1  0
 12  6  1  0
 22 16  1  0
  5 25  1  0
  7 26  1  0
  8 27  1  0
 10 28  1  0
 11 29  1  0
 12 30  1  0
 17 31  1  0
 18 32  1  0
 20 33  1  0
 21 34  1  0
 22 35  1  0
 24 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       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -6.668  -5.390   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -8.002  -7.700   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -8.002  -4.620   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -9.336  -6.930   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.334  -6.930   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -6.668  -6.930   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -9.336  -5.390   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -2.667  -7.700   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -5.335  -7.700   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -4.001  -6.930   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -5.335  -9.240   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -4.001 -10.010   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -1.334  -0.770   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0     -10.669  -4.620   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      -4.001  -5.390   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      -6.668 -10.010   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      -4.001 -11.550   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0      -2.667  -9.240   0.000  0.00  0.00           O+0
CONECT    1    5   10                                                       
CONECT    2    6   10                                                       
CONECT    3    7   11                                                       
CONECT    4    8   11                                                       
CONECT    5    1   12                                                       
CONECT    6    2   12                                                       
CONECT    7    3   13                                                       
CONECT    8    4   13                                                       
CONECT    9   10   14                                                       
CONECT   10    1    2    9                                                  
CONECT   11    3    4   15                                                  
CONECT   12    5    6   19                                                  
CONECT   13    7    8   20                                                  
CONECT   14    9   16   24                                                  
CONECT   15   11   16   17                                                  
CONECT   16   14   15   21                                                  
CONECT   17   15   18   22                                                  
CONECT   18   17   23   24                                                  
CONECT   19   12                                                            
CONECT   20   13                                                            
CONECT   21   16                                                            
CONECT   22   17                                                            
CONECT   23   18                                                            
CONECT   24   14   18                                                       
MASTER        0    0    0    0    0    0    0    0   24    0   52    0
END

COMPND    HMDB0029535
HETATM    1  O1  UNL     1      -1.711  -4.681   0.576  1.00  0.00           O  
HETATM    2  C1  UNL     1      -1.118  -3.568   0.417  1.00  0.00           C  
HETATM    3  O2  UNL     1       0.264  -3.483   0.348  1.00  0.00           O  
HETATM    4  C2  UNL     1       0.882  -2.243   0.174  1.00  0.00           C  
HETATM    5  C3  UNL     1       2.199  -2.120   0.099  1.00  0.00           C  
HETATM    6  C4  UNL     1       2.889  -0.860  -0.066  1.00  0.00           C  
HETATM    7  C5  UNL     1       3.606  -0.607  -1.192  1.00  0.00           C  
HETATM    8  C6  UNL     1       4.326   0.563  -1.368  1.00  0.00           C  
HETATM    9  C7  UNL     1       4.321   1.502  -0.377  1.00  0.00           C  
HETATM   10  O3  UNL     1       5.029   2.716  -0.485  1.00  0.00           O  
HETATM   11  C8  UNL     1       3.596   1.247   0.764  1.00  0.00           C  
HETATM   12  C9  UNL     1       2.878   0.083   0.941  1.00  0.00           C  
HETATM   13  C10 UNL     1       0.018  -1.076   0.070  1.00  0.00           C  
HETATM   14  O4  UNL     1       0.488   0.072  -0.091  1.00  0.00           O  
HETATM   15  C11 UNL     1      -1.446  -1.191   0.147  1.00  0.00           C  
HETATM   16  C12 UNL     1      -2.246   0.020   0.047  1.00  0.00           C  
HETATM   17  C13 UNL     1      -3.241   0.332   0.952  1.00  0.00           C  
HETATM   18  C14 UNL     1      -4.011   1.469   0.817  1.00  0.00           C  
HETATM   19  C15 UNL     1      -3.824   2.358  -0.241  1.00  0.00           C  
HETATM   20  O5  UNL     1      -4.606   3.497  -0.368  1.00  0.00           O  
HETATM   21  C16 UNL     1      -2.826   2.039  -1.142  1.00  0.00           C  
HETATM   22  C17 UNL     1      -2.053   0.889  -0.996  1.00  0.00           C  
HETATM   23  C18 UNL     1      -1.976  -2.393   0.314  1.00  0.00           C  
HETATM   24  O6  UNL     1      -3.372  -2.448   0.380  1.00  0.00           O  
HETATM   25  H1  UNL     1       2.749  -3.072   0.177  1.00  0.00           H  
HETATM   26  H2  UNL     1       3.657  -1.320  -2.033  1.00  0.00           H  
HETATM   27  H3  UNL     1       4.869   0.720  -2.261  1.00  0.00           H  
HETATM   28  H4  UNL     1       4.989   3.357   0.264  1.00  0.00           H  
HETATM   29  H5  UNL     1       3.608   2.012   1.545  1.00  0.00           H  
HETATM   30  H6  UNL     1       2.339  -0.047   1.877  1.00  0.00           H  
HETATM   31  H7  UNL     1      -3.398  -0.343   1.776  1.00  0.00           H  
HETATM   32  H8  UNL     1      -4.802   1.736   1.516  1.00  0.00           H  
HETATM   33  H9  UNL     1      -4.372   4.378   0.020  1.00  0.00           H  
HETATM   34  H10 UNL     1      -2.663   2.718  -1.974  1.00  0.00           H  
HETATM   35  H11 UNL     1      -1.271   0.681  -1.741  1.00  0.00           H  
HETATM   36  H12 UNL     1      -3.773  -2.939   1.158  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3   23
CONECT    3    4
CONECT    4    5    5   13
CONECT    5    6   25
CONECT    6    7    7   12
CONECT    7    8   26
CONECT    8    9    9   27
CONECT    9   10   11
CONECT   10   28
CONECT   11   12   12   29
CONECT   12   30
CONECT   13   14   14   15
CONECT   15   16   23   23
CONECT   16   17   17   22
CONECT   17   18   31
CONECT   18   19   19   32
CONECT   19   20   21
CONECT   20   33
CONECT   21   22   22   34
CONECT   22   35
CONECT   23   24
CONECT   24   36
END

HMDB0029535
     RDKit          3D
Grevilline A
 36 38  0  0  0  0  0  0  0  0999 V2000
   -1.7109   -4.6807    0.5761 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1185   -3.5676    0.4173 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2644   -3.4831    0.3481 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8823   -2.2425    0.1741 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1993   -2.1200    0.0991 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8886   -0.8596   -0.0657 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6065   -0.6073   -1.1916 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3264    0.5633   -1.3679 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3212    1.5016   -0.3775 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0288    2.7159   -0.4852 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5962    1.2472    0.7644 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8782    0.0834    0.9412 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0178   -1.0763    0.0705 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4880    0.0715   -0.0909 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4462   -1.1913    0.1469 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2455    0.0198    0.0469 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2407    0.3317    0.9523 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0112    1.4694    0.8166 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8236    2.3578   -0.2411 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6060    3.4970   -0.3681 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8260    2.0390   -1.1421 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0533    0.8891   -0.9958 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9762   -2.3928    0.3136 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3716   -2.4478    0.3799 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7488   -3.0723    0.1773 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6572   -1.3197   -2.0333 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8694    0.7201   -2.2610 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9889    3.3573    0.2640 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6084    2.0123    1.5455 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3385   -0.0471    1.8769 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3979   -0.3434    1.7757 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8020    1.7364    1.5164 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3723    4.3783    0.0199 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6625    2.7185   -1.9736 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2712    0.6809   -1.7408 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7733   -2.9389    1.1579 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
  9 11  1  0
 11 12  2  0
  4 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 19 21  1  0
 21 22  2  0
 15 23  2  0
 23 24  1  0
 23  2  1  0
 12  6  1  0
 22 16  1  0
  5 25  1  0
  7 26  1  0
  8 27  1  0
 10 28  1  0
 11 29  1  0
 12 30  1  0
 17 31  1  0
 18 32  1  0
 20 33  1  0
 21 34  1  0
 22 35  1  0
 24 36  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
3-Hydroxy-4-(4-hydroxyphenyl)-6-[(4-hydroxyphenylmethylene)]-2H-pyran-2,5(6H)-dione, 9ci	HMDB

Chemical Formula

C₁₈H₁₂O₆

Average Molecular Weight

324.2843

Monoisotopic Molecular Weight

324.063388116

IUPAC Name

(6E)-3-hydroxy-4-(4-hydroxyphenyl)-6-[(4-hydroxyphenyl)methylidene]-5,6-dihydro-2H-pyran-2,5-dione

Traditional Name

(6E)-3-hydroxy-4-(4-hydroxyphenyl)-6-[(4-hydroxyphenyl)methylidene]pyran-2,5-dione

CAS Registry Number

41744-32-5

SMILES

OC1=CC=C(\C=C2\OC(=O)C(O)=C(C2=O)C2=CC=C(O)C=C2)C=C1

InChI Identifier

InChI=1S/C18H12O6/c19-12-5-1-10(2-6-12)9-14-16(21)15(17(22)18(23)24-14)11-3-7-13(20)8-4-11/h1-9,19-20,22H/b14-9+

InChI Key

PZEIKFYZAURRNF-NTEUORMPSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as dihydropyranones. Dihydropyranones are compounds containing a hydrogenated pyran ring which bears a ketone, and contains one double bond.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Pyrans

Sub Class

Pyranones and derivatives

Direct Parent

Dihydropyranones

Alternative Parents

Substituents

1-hydroxy-2-unsubstituted benzenoid
Dihydropyranone
Phenol
Monocyclic benzene moiety
Benzenoid
Vinylogous acid
Enol ester
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Carboxylic acid ester
Ketone
Lactone
Cyclic ketone
Oxacycle
Enol
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Carbonyl group
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Organic oxide
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0029535)
Cell membrane (HMDB: HMDB0029535)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0029535)

Source

Endogenous

Endogenous (HMDB: HMDB0029535)

Plant

Plant (HMDB: HMDB0029535)

Exogenous

Food

Food (HMDB: HMDB0029535)

Vegetable

Mushroom

Exogenous (HMDB: HMDB0029535)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	197 - 199 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	167.7 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	0.083 g/L	ALOGPS
logP	2.66	ALOGPS
logP	3.04	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Acidic)	7.91	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	104.06 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	87.43 m³·mol⁻¹	ChemAxon
Polarizability	31.7 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
DeepCCS	[M+H]+	177.315	30932474
DeepCCS	[M-H]-	174.957	30932474
DeepCCS	[M-2H]-	208.716	30932474
DeepCCS	[M+Na]+	183.944	30932474
AllCCS	[M+H]+	176.8	32859911
AllCCS	[M+H-H2O]+	173.3	32859911
AllCCS	[M+NH4]+	180.0	32859911
AllCCS	[M+Na]+	181.0	32859911
AllCCS	[M-H]-	175.2	32859911
AllCCS	[M+Na-2H]-	174.7	32859911
AllCCS	[M+HCOO]-	174.2	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Grevilline A	OC1=CC=C(\C=C2\OC(=O)C(O)=C(C2=O)C2=CC=C(O)C=C2)C=C1	5089.7	Standard polar	33892256
Grevilline A	OC1=CC=C(\C=C2\OC(=O)C(O)=C(C2=O)C2=CC=C(O)C=C2)C=C1	2839.3	Standard non polar	33892256
Grevilline A	OC1=CC=C(\C=C2\OC(=O)C(O)=C(C2=O)C2=CC=C(O)C=C2)C=C1	3527.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Grevilline A,1TMS,isomer #1	C[Si](C)(C)OC1=CC=C(/C=C2/OC(=O)C(O)=C(C3=CC=C(O)C=C3)C2=O)C=C1	3373.3	Semi standard non polar	33892256
Grevilline A,1TMS,isomer #2	C[Si](C)(C)OC1=C(C2=CC=C(O)C=C2)C(=O)/C(=C\C2=CC=C(O)C=C2)OC1=O	3262.6	Semi standard non polar	33892256
Grevilline A,1TMS,isomer #3	C[Si](C)(C)OC1=CC=C(C2=C(O)C(=O)O/C(=C/C3=CC=C(O)C=C3)C2=O)C=C1	3354.9	Semi standard non polar	33892256
Grevilline A,2TMS,isomer #1	C[Si](C)(C)OC1=C(C2=CC=C(O)C=C2)C(=O)/C(=C\C2=CC=C(O[Si](C)(C)C)C=C2)OC1=O	3270.3	Semi standard non polar	33892256
Grevilline A,2TMS,isomer #2	C[Si](C)(C)OC1=CC=C(/C=C2/OC(=O)C(O)=C(C3=CC=C(O[Si](C)(C)C)C=C3)C2=O)C=C1	3397.3	Semi standard non polar	33892256
Grevilline A,2TMS,isomer #3	C[Si](C)(C)OC1=C(C2=CC=C(O[Si](C)(C)C)C=C2)C(=O)/C(=C\C2=CC=C(O)C=C2)OC1=O	3249.7	Semi standard non polar	33892256
Grevilline A,3TMS,isomer #1	C[Si](C)(C)OC1=C(C2=CC=C(O[Si](C)(C)C)C=C2)C(=O)/C(=C\C2=CC=C(O[Si](C)(C)C)C=C2)OC1=O	3306.6	Semi standard non polar	33892256
Grevilline A,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=C(/C=C2/OC(=O)C(O)=C(C3=CC=C(O)C=C3)C2=O)C=C1	3642.4	Semi standard non polar	33892256
Grevilline A,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=C(C2=CC=C(O)C=C2)C(=O)/C(=C\C2=CC=C(O)C=C2)OC1=O	3566.0	Semi standard non polar	33892256
Grevilline A,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC1=CC=C(C2=C(O)C(=O)O/C(=C/C3=CC=C(O)C=C3)C2=O)C=C1	3621.6	Semi standard non polar	33892256
Grevilline A,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=C(C2=CC=C(O)C=C2)C(=O)/C(=C\C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C2)OC1=O	3867.4	Semi standard non polar	33892256
Grevilline A,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC=C(/C=C2/OC(=O)C(O)=C(C3=CC=C(O[Si](C)(C)C(C)(C)C)C=C3)C2=O)C=C1	3952.4	Semi standard non polar	33892256
Grevilline A,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC1=C(C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C2)C(=O)/C(=C\C2=CC=C(O)C=C2)OC1=O	3852.6	Semi standard non polar	33892256
Grevilline A,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=C(C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C2)C(=O)/C(=C\C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C2)OC1=O	4133.1	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Grevilline A GC-MS (Non-derivatized) - 70eV, Positive	splash10-001j-0961000000-6711da0f447ed2372c89	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Grevilline A GC-MS (3 TMS) - 70eV, Positive	splash10-046r-4191740000-d5462a1b41da8c8ca361	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Grevilline A 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 - Grevilline A 10V, Positive-QTOF	splash10-004i-0119000000-8b5a3bf350e8155399fa	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Grevilline A 20V, Positive-QTOF	splash10-0a6r-0898000000-a20f647078756bb1824e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Grevilline A 40V, Positive-QTOF	splash10-07wj-3910000000-3d0abc570c9cca19c496	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Grevilline A 10V, Negative-QTOF	splash10-00fr-0389000000-2032691f1d92d20e4de1	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Grevilline A 20V, Negative-QTOF	splash10-0101-0896000000-567bc4492a825cfd2169	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Grevilline A 40V, Negative-QTOF	splash10-07cs-0910000000-5c072932be6138411bdf	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Grevilline A 10V, Positive-QTOF	splash10-004i-0009000000-3ccf9c8a3e8c981e7a46	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Grevilline A 20V, Positive-QTOF	splash10-004i-0619000000-404cd9908796b6998988	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Grevilline A 40V, Positive-QTOF	splash10-0a4i-0930000000-25bc7fa4ec9dfc7a706d	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Grevilline A 10V, Negative-QTOF	splash10-00di-0009000000-1e58a8f96c64172c0c0f	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Grevilline A 20V, Negative-QTOF	splash10-00di-0319000000-4225b84cc3927785012a	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Grevilline A 40V, Negative-QTOF	splash10-00lr-0950000000-a6abdf6e40a33c496b6c	2021-09-22	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB000676

KNApSAcK ID

Not Available

Chemspider ID

29743092

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1810281

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 Grevilline A (HMDB0029535)

MOL for HMDB0029535 (Grevilline A)

3D MOL for HMDB0029535 (Grevilline A)

3D SDF for HMDB0029535 (Grevilline A)

3D-SDF for HMDB0029535 (Grevilline A)

PDB for HMDB0029535 (Grevilline A)

3D PDB for HMDB0029535 (Grevilline A)

SMILES for HMDB0029535 (Grevilline A)

INCHI for HMDB0029535 (Grevilline A)

Structure for HMDB0029535 (Grevilline A)

3D Structure for HMDB0029535 (Grevilline A)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra