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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2021-09-24 02:17:54 UTC

Update Date

2021-09-24 02:17:54 UTC

HMDB ID

HMDB0303491

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Grosheimin

Description

Grosheimin belongs to guaianolides and derivatives class of compounds. Those are diterpene lactones with a structure characterized by the presence of a gamma-lactone fused to a guaiane, forming 3,6,9-trimethyl-azuleno[4,5-b]furan-2-one or a derivative. Grosheimin is slightly soluble (in water) and a very weakly acidic compound (based on its pKa). Grosheimin is a bitter tasting compound found in globe artichoke, which makes grosheimin a potential biomarker for the consumption of this food product.

Structure

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

HMDB0303491
     RDKit          3D
Grosheimin
 37 39  0  0  0  0  0  0  0  0999 V2000
   -0.8399   -3.2054   -0.4181 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3407   -1.9941   -0.2669 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9885   -1.9323    0.3501 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8764   -0.8485   -0.1803 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1940   -1.1972    0.1192 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5904    0.5069    0.4129 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5467    1.4297   -0.2466 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7213    1.7677    0.2075 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8719    1.8384   -1.4657 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3912    2.5318   -2.3876 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5556    1.3271   -1.4290 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3073    1.1041   -0.0625 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9109    0.2991    0.2180 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1078    1.1976   -0.0138 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3406    2.1494    1.1312 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2076    0.2088   -0.1325 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3853    0.4128    0.0840 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6359   -1.0959   -0.5657 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1528   -0.8287   -0.7249 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8044   -3.3799   -0.8571 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2643   -4.0520   -0.0917 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9427   -1.8416    1.4676 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5022   -2.8982    0.1605 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8068   -0.7435   -1.2781 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2740   -2.1446    0.4258 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7065    0.5191    1.5151 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3742    2.4551   -0.3339 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0665    1.3613    1.1449 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1925    2.0922    0.4182 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8489   -0.0616    1.2658 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9768    1.6946   -0.9788 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2361    3.2034    0.8566 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6246    1.9095    1.9243 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3772    2.0131    1.5513 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1044   -1.4158   -1.5131 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8356   -1.8225    0.2452 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9153   -0.5598   -1.7615 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  1  0
  4  5  1  0
  4  6  1  0
  6  7  1  0
  7  8  2  3
  7  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  1  0
 16 17  2  0
 16 18  1  0
 18 19  1  0
 19  2  1  0
 12  6  1  0
 19 13  1  0
  1 20  1  0
  1 21  1  0
  3 22  1  0
  3 23  1  0
  4 24  1  0
  5 25  1  0
  6 26  1  0
  8 27  1  0
  8 28  1  0
 12 29  1  0
 13 30  1  0
 14 31  1  0
 15 32  1  0
 15 33  1  0
 15 34  1  0
 18 35  1  0
 18 36  1  0
 19 37  1  0
M  END


  Mrv0541 02241217472D          

 19 21  0  0  0  0            999 V2000
   -1.0906    1.7537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5340    1.1462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2562    1.3826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9352    0.9112    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6498    1.3236    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7221   -1.2162    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5413   -1.1241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0979   -1.7330    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8253   -1.7537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9902   -0.9454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7420   -0.6018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6486    0.2144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8432    0.3794    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4309   -0.3353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3799   -0.4658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9901    0.0935    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7048   -0.3187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4566    0.0248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4566   -1.0142    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  2 13  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4 16  1  0  0  0  0
  6  7  1  0  0  0  0
  6 15  1  0  0  0  0
  7  8  2  0  0  0  0
  7 17  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 14  1  0  0  0  0
 11 12  1  0  0  0  0
 11 19  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0303491

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1C2C3OC(=O)C(=C)C3C(O)CC(=C)C2CC1=O

> <INCHI_IDENTIFIER>
InChI=1S/C15H18O4/c1-6-4-11(17)13-8(3)15(18)19-14(13)12-7(2)10(16)5-9(6)12/h7,9,11-14,17H,1,3-5H2,2H3

> <INCHI_KEY>
YGMIBVIKXJJQQJ-UHFFFAOYSA-N

> <FORMULA>
C15H18O4

> <MOLECULAR_WEIGHT>
262.301

> <EXACT_MASS>
262.120509064

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
27.117443377330737

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-hydroxy-9-methyl-3,6-dimethylidene-dodecahydroazuleno[4,5-b]furan-2,8-dione

> <ALOGPS_LOGP>
0.18

> <JCHEM_LOGP>
1.154488685

> <ALOGPS_LOGS>
-1.74

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
18.477140277542325

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.713471484654601

> <JCHEM_PKA_STRONGEST_BASIC>
-2.924091549163374

> <JCHEM_POLAR_SURFACE_AREA>
63.6

> <JCHEM_REFRACTIVITY>
68.4319

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.77e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-hydroxy-9-methyl-3,6-dimethylidene-octahydroazuleno[4,5-b]furan-2,8-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0303491
     RDKit          3D
Grosheimin
 37 39  0  0  0  0  0  0  0  0999 V2000
   -0.8399   -3.2054   -0.4181 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3407   -1.9941   -0.2669 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9885   -1.9323    0.3501 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8764   -0.8485   -0.1803 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1940   -1.1972    0.1192 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5904    0.5069    0.4129 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5467    1.4297   -0.2466 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7213    1.7677    0.2075 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8719    1.8384   -1.4657 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3912    2.5318   -2.3876 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5556    1.3271   -1.4290 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3073    1.1041   -0.0625 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9109    0.2991    0.2180 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1078    1.1976   -0.0138 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3406    2.1494    1.1312 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2076    0.2088   -0.1325 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3853    0.4128    0.0840 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6359   -1.0959   -0.5657 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1528   -0.8287   -0.7249 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8044   -3.3799   -0.8571 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2643   -4.0520   -0.0917 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9427   -1.8416    1.4676 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5022   -2.8982    0.1605 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8068   -0.7435   -1.2781 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2740   -2.1446    0.4258 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7065    0.5191    1.5151 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3742    2.4551   -0.3339 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0665    1.3613    1.1449 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1925    2.0922    0.4182 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8489   -0.0616    1.2658 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9768    1.6946   -0.9788 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2361    3.2034    0.8566 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6246    1.9095    1.9243 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3772    2.0131    1.5513 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1044   -1.4158   -1.5131 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8356   -1.8225    0.2452 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9153   -0.5598   -1.7615 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  1  0
  4  5  1  0
  4  6  1  0
  6  7  1  0
  7  8  2  3
  7  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  1  0
 16 17  2  0
 16 18  1  0
 18 19  1  0
 19  2  1  0
 12  6  1  0
 19 13  1  0
  1 20  1  0
  1 21  1  0
  3 22  1  0
  3 23  1  0
  4 24  1  0
  5 25  1  0
  6 26  1  0
  8 27  1  0
  8 28  1  0
 12 29  1  0
 13 30  1  0
 14 31  1  0
 15 32  1  0
 15 33  1  0
 15 34  1  0
 18 35  1  0
 18 36  1  0
 19 37  1  0
M  END

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      -2.036   3.274   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.997   2.140   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.478   2.581   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.746   1.701   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       3.080   2.471   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0       1.348  -2.270   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       2.877  -2.098   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       3.916  -3.235   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      -1.541  -3.274   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.848  -1.765   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -3.252  -1.123   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -3.077   0.400   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.574   0.708   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.804  -0.626   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.709  -0.869   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.848   0.175   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.182  -0.595   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.586   0.046   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -4.586  -1.893   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   13                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   16                                                  
CONECT    5    4                                                            
CONECT    6    7   15                                                       
CONECT    7    6    8   17                                                  
CONECT    8    7                                                            
CONECT    9   10                                                            
CONECT   10    9   11   14                                                  
CONECT   11   10   12   19                                                  
CONECT   12   11   13                                                       
CONECT   13    2   12   14                                                  
CONECT   14   10   13   15                                                  
CONECT   15    6   14   16                                                  
CONECT   16    4   15   17                                                  
CONECT   17    7   16   18                                                  
CONECT   18   17                                                            
CONECT   19   11                                                            
MASTER        0    0    0    0    0    0    0    0   19    0   42    0
END

COMPND    HMDB0303491
HETATM    1  C1  UNL     1      -0.840  -3.205  -0.418  1.00  0.00           C  
HETATM    2  C2  UNL     1      -0.341  -1.994  -0.267  1.00  0.00           C  
HETATM    3  C3  UNL     1       0.988  -1.932   0.350  1.00  0.00           C  
HETATM    4  C4  UNL     1       1.876  -0.848  -0.180  1.00  0.00           C  
HETATM    5  O1  UNL     1       3.194  -1.197   0.119  1.00  0.00           O  
HETATM    6  C5  UNL     1       1.590   0.507   0.413  1.00  0.00           C  
HETATM    7  C6  UNL     1       2.547   1.430  -0.247  1.00  0.00           C  
HETATM    8  C7  UNL     1       3.721   1.768   0.208  1.00  0.00           C  
HETATM    9  C8  UNL     1       1.872   1.838  -1.466  1.00  0.00           C  
HETATM   10  O2  UNL     1       2.391   2.532  -2.388  1.00  0.00           O  
HETATM   11  O3  UNL     1       0.556   1.327  -1.429  1.00  0.00           O  
HETATM   12  C9  UNL     1       0.307   1.104  -0.062  1.00  0.00           C  
HETATM   13  C10 UNL     1      -0.911   0.299   0.218  1.00  0.00           C  
HETATM   14  C11 UNL     1      -2.108   1.198  -0.014  1.00  0.00           C  
HETATM   15  C12 UNL     1      -2.341   2.149   1.131  1.00  0.00           C  
HETATM   16  C13 UNL     1      -3.208   0.209  -0.133  1.00  0.00           C  
HETATM   17  O4  UNL     1      -4.385   0.413   0.084  1.00  0.00           O  
HETATM   18  C14 UNL     1      -2.636  -1.096  -0.566  1.00  0.00           C  
HETATM   19  C15 UNL     1      -1.153  -0.829  -0.725  1.00  0.00           C  
HETATM   20  H1  UNL     1      -1.804  -3.380  -0.857  1.00  0.00           H  
HETATM   21  H2  UNL     1      -0.264  -4.052  -0.092  1.00  0.00           H  
HETATM   22  H3  UNL     1       0.943  -1.842   1.468  1.00  0.00           H  
HETATM   23  H4  UNL     1       1.502  -2.898   0.160  1.00  0.00           H  
HETATM   24  H5  UNL     1       1.807  -0.744  -1.278  1.00  0.00           H  
HETATM   25  H6  UNL     1       3.274  -2.145   0.426  1.00  0.00           H  
HETATM   26  H7  UNL     1       1.706   0.519   1.515  1.00  0.00           H  
HETATM   27  H8  UNL     1       4.374   2.455  -0.334  1.00  0.00           H  
HETATM   28  H9  UNL     1       4.067   1.361   1.145  1.00  0.00           H  
HETATM   29  H10 UNL     1       0.193   2.092   0.418  1.00  0.00           H  
HETATM   30  H11 UNL     1      -0.849  -0.062   1.266  1.00  0.00           H  
HETATM   31  H12 UNL     1      -1.977   1.695  -0.979  1.00  0.00           H  
HETATM   32  H13 UNL     1      -2.236   3.203   0.857  1.00  0.00           H  
HETATM   33  H14 UNL     1      -1.625   1.909   1.924  1.00  0.00           H  
HETATM   34  H15 UNL     1      -3.377   2.013   1.551  1.00  0.00           H  
HETATM   35  H16 UNL     1      -3.104  -1.416  -1.513  1.00  0.00           H  
HETATM   36  H17 UNL     1      -2.836  -1.822   0.245  1.00  0.00           H  
HETATM   37  H18 UNL     1      -0.915  -0.560  -1.761  1.00  0.00           H  
CONECT    1    2    2   20   21
CONECT    2    3   19
CONECT    3    4   22   23
CONECT    4    5    6   24
CONECT    5   25
CONECT    6    7   12   26
CONECT    7    8    8    9
CONECT    8   27   28
CONECT    9   10   10   11
CONECT   11   12
CONECT   12   13   29
CONECT   13   14   19   30
CONECT   14   15   16   31
CONECT   15   32   33   34
CONECT   16   17   17   18
CONECT   18   19   35   36
CONECT   19   37
END

HMDB0303491
     RDKit          3D
Grosheimin
 37 39  0  0  0  0  0  0  0  0999 V2000
   -0.8399   -3.2054   -0.4181 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3407   -1.9941   -0.2669 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9885   -1.9323    0.3501 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8764   -0.8485   -0.1803 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1940   -1.1972    0.1192 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5904    0.5069    0.4129 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5467    1.4297   -0.2466 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7213    1.7677    0.2075 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8719    1.8384   -1.4657 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3912    2.5318   -2.3876 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5556    1.3271   -1.4290 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3073    1.1041   -0.0625 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9109    0.2991    0.2180 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1078    1.1976   -0.0138 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3406    2.1494    1.1312 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2076    0.2088   -0.1325 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3853    0.4128    0.0840 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6359   -1.0959   -0.5657 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1528   -0.8287   -0.7249 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8044   -3.3799   -0.8571 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2643   -4.0520   -0.0917 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9427   -1.8416    1.4676 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5022   -2.8982    0.1605 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8068   -0.7435   -1.2781 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2740   -2.1446    0.4258 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7065    0.5191    1.5151 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3742    2.4551   -0.3339 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0665    1.3613    1.1449 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1925    2.0922    0.4182 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8489   -0.0616    1.2658 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9768    1.6946   -0.9788 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2361    3.2034    0.8566 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6246    1.9095    1.9243 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3772    2.0131    1.5513 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1044   -1.4158   -1.5131 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8356   -1.8225    0.2452 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9153   -0.5598   -1.7615 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  1  0
  4  5  1  0
  4  6  1  0
  6  7  1  0
  7  8  2  3
  7  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  1  0
 16 17  2  0
 16 18  1  0
 18 19  1  0
 19  2  1  0
 12  6  1  0
 19 13  1  0
  1 20  1  0
  1 21  1  0
  3 22  1  0
  3 23  1  0
  4 24  1  0
  5 25  1  0
  6 26  1  0
  8 27  1  0
  8 28  1  0
 12 29  1  0
 13 30  1  0
 14 31  1  0
 15 32  1  0
 15 33  1  0
 15 34  1  0
 18 35  1  0
 18 36  1  0
 19 37  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₁₅H₁₈O₄

Average Molecular Weight

262.301

Monoisotopic Molecular Weight

262.120509064

IUPAC Name

4-hydroxy-9-methyl-3,6-dimethylidene-dodecahydroazuleno[4,5-b]furan-2,8-dione

Traditional Name

4-hydroxy-9-methyl-3,6-dimethylidene-octahydroazuleno[4,5-b]furan-2,8-dione

CAS Registry Number

Not Available

SMILES

CC1C2C3OC(=O)C(=C)C3C(O)CC(=C)C2CC1=O

InChI Identifier

InChI=1S/C15H18O4/c1-6-4-11(17)13-8(3)15(18)19-14(13)12-7(2)10(16)5-9(6)12/h7,9,11-14,17H,1,3-5H2,2H3

InChI Key

YGMIBVIKXJJQQJ-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as guaianolides and derivatives. These are diterpene lactones with a structure characterized by the presence of a gamma-lactone fused to a guaiane, forming 3,6,9-trimethyl-azuleno[4,5-b]furan-2-one or a derivative.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Guaianolides and derivatives

Alternative Parents

Substituents

Guaianolide-skeleton
Guaiane sesquiterpenoid
Sesquiterpenoid
Gamma butyrolactone
Cyclic alcohol
Tetrahydrofuran
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Secondary alcohol
Lactone
Ketone
Carboxylic acid ester
Cyclic ketone
Oxacycle
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organoheterocyclic compound
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Alcohol
Carbonyl group
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Organoleptic effect

Odor

bitter

Globe artichoke (FooDB: FOOD00071)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	0.18	ALOGPS
logP	1.15	ChemAxon
logS	-1.7	ALOGPS
pKa (Strongest Acidic)	14.71	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	63.6 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	68.43 m³·mol⁻¹	ChemAxon
Polarizability	27.12 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
AllCCS	[M+H]+	160.815	32859911
AllCCS	[M+H-H2O]+	157.235	32859911
AllCCS	[M+Na]+	165.094	32859911
AllCCS	[M+NH4]+	164.138	32859911
AllCCS	[M-H]-	163.949	32859911
AllCCS	[M+Na-2H]-	163.755	32859911
AllCCS	[M+HCOO]-	163.657	32859911
DeepCCS	[M+H]+	162.689	30932474
DeepCCS	[M-H]-	160.331	30932474
DeepCCS	[M-2H]-	193.217	30932474
DeepCCS	[M+Na]+	168.782	30932474

Predicted Kovats Retention Indices

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Grosheimin,2TMS,isomer #1	C=C1CC(O[Si](C)(C)C)C2C(=C)C(=O)OC2C2C(C)=C(O[Si](C)(C)C)CC12	2343.5	Semi standard non polar	33892256
Grosheimin,2TMS,isomer #1	C=C1CC(O[Si](C)(C)C)C2C(=C)C(=O)OC2C2C(C)=C(O[Si](C)(C)C)CC12	2175.7	Standard non polar	33892256
Grosheimin,2TMS,isomer #1	C=C1CC(O[Si](C)(C)C)C2C(=C)C(=O)OC2C2C(C)=C(O[Si](C)(C)C)CC12	2598.2	Standard polar	33892256
Grosheimin,2TMS,isomer #2	C=C1CC(O[Si](C)(C)C)C2C(=C)C(=O)OC2C2C(C)C(O[Si](C)(C)C)=CC12	2271.1	Semi standard non polar	33892256
Grosheimin,2TMS,isomer #2	C=C1CC(O[Si](C)(C)C)C2C(=C)C(=O)OC2C2C(C)C(O[Si](C)(C)C)=CC12	2131.3	Standard non polar	33892256
Grosheimin,2TMS,isomer #2	C=C1CC(O[Si](C)(C)C)C2C(=C)C(=O)OC2C2C(C)C(O[Si](C)(C)C)=CC12	2582.1	Standard polar	33892256
Grosheimin,2TBDMS,isomer #1	C=C1CC(O[Si](C)(C)C(C)(C)C)C2C(=C)C(=O)OC2C2C(C)=C(O[Si](C)(C)C(C)(C)C)CC12	2770.2	Semi standard non polar	33892256
Grosheimin,2TBDMS,isomer #1	C=C1CC(O[Si](C)(C)C(C)(C)C)C2C(=C)C(=O)OC2C2C(C)=C(O[Si](C)(C)C(C)(C)C)CC12	2611.1	Standard non polar	33892256
Grosheimin,2TBDMS,isomer #1	C=C1CC(O[Si](C)(C)C(C)(C)C)C2C(=C)C(=O)OC2C2C(C)=C(O[Si](C)(C)C(C)(C)C)CC12	2824.7	Standard polar	33892256
Grosheimin,2TBDMS,isomer #2	C=C1CC(O[Si](C)(C)C(C)(C)C)C2C(=C)C(=O)OC2C2C(C)C(O[Si](C)(C)C(C)(C)C)=CC12	2723.1	Semi standard non polar	33892256
Grosheimin,2TBDMS,isomer #2	C=C1CC(O[Si](C)(C)C(C)(C)C)C2C(=C)C(=O)OC2C2C(C)C(O[Si](C)(C)C(C)(C)C)=CC12	2493.2	Standard non polar	33892256
Grosheimin,2TBDMS,isomer #2	C=C1CC(O[Si](C)(C)C(C)(C)C)C2C(=C)C(=O)OC2C2C(C)C(O[Si](C)(C)C(C)(C)C)=CC12	2805.4	Standard polar	33892256

Spectra

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Grosheimin 10V, Positive-QTOF	splash10-01ot-0190000000-0540d20474782bf3fb62	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Grosheimin 20V, Positive-QTOF	splash10-01vt-0690000000-b9b30483196b9ab2e09b	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Grosheimin 40V, Positive-QTOF	splash10-0uxu-9820000000-a17e83da187ce5911fba	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Grosheimin 10V, Negative-QTOF	splash10-03di-0090000000-160857df66d82a2df5ec	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Grosheimin 20V, Negative-QTOF	splash10-03xu-0090000000-8c3cc5a92665e415c59e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Grosheimin 40V, Negative-QTOF	splash10-0uel-9620000000-140666a741e54aec42b3	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Grosheimin 10V, Positive-QTOF	splash10-0002-0090000000-da9d0d5c94a2c230a2b3	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Grosheimin 20V, Positive-QTOF	splash10-004i-0490000000-8e106798a130462c302d	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Grosheimin 40V, Positive-QTOF	splash10-00rj-1970000000-d72fc2dd8211965429eb	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Grosheimin 10V, Negative-QTOF	splash10-03di-0090000000-9e603373aa78758870d8	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Grosheimin 20V, Negative-QTOF	splash10-0006-0290000000-d81b674584777c7372ab	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Grosheimin 40V, Negative-QTOF	splash10-0096-1950000000-a38d73758241fb91bfe3	2021-10-21	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB014671

KNApSAcK ID

Not Available

Chemspider ID

90324

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

99967

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Showing metabocard for Grosheimin (HMDB0303491)

MOL for HMDB0303491 (Grosheimin)

3D MOL for HMDB0303491 (Grosheimin)

3D SDF for HMDB0303491 (Grosheimin)

3D-SDF for HMDB0303491 (Grosheimin)

PDB for HMDB0303491 (Grosheimin)

3D PDB for HMDB0303491 (Grosheimin)

SMILES for HMDB0303491 (Grosheimin)

INCHI for HMDB0303491 (Grosheimin)

Structure for HMDB0303491 (Grosheimin)

3D Structure for HMDB0303491 (Grosheimin)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Derivatized

MS/MS Spectra