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Showing metabocard for (-)-trans-3,4-Dihydro-4,8-dihydroxy-3-methyl-1H-2-benzopyran-1-one (HMDB0030765)

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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:38:54 UTC
Update Date2022-03-07 02:52:41 UTC
HMDB IDHMDB0030765
Secondary Accession Numbers
  • HMDB30765
Metabolite Identification
Common Name(-)-trans-3,4-Dihydro-4,8-dihydroxy-3-methyl-1H-2-benzopyran-1-one
Description(-)-trans-3,4-Dihydro-4,8-dihydroxy-3-methyl-1H-2-benzopyran-1-one, also known as 3-methyl-4,8-dihydroxy-3,4-dihydroisocoumarin or 4,8-dihydroxy-3-methylbenzopyran-1-one, belongs to the class of organic compounds known as 2-benzopyrans. These are organic aromatic compounds that 1-benzopyran, a bicyclic compound made up of a benzene ring fused to a pyran, so that the oxygen atom is at the 2-position (-)-trans-3,4-Dihydro-4,8-dihydroxy-3-methyl-1H-2-benzopyran-1-one is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Based on a literature review a significant number of articles have been published on (-)-trans-3,4-Dihydro-4,8-dihydroxy-3-methyl-1H-2-benzopyran-1-one.
Structure
Data?1563862034
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0030765 ((-)-trans-3,4-Dihydro-4,8-dihydroxy-3-methyl-1H-2-benzopyran-1-one)

  Mrv0541 05061305292D          

 14 15  0  0  0  0            999 V2000
    5.0013    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  2  0  0  0  0
  4  2  1  0  0  0  0
  5  1  1  0  0  0  0
  6  3  1  0  0  0  0
  7  4  2  0  0  0  0
  8  6  2  0  0  0  0
  8  7  1  0  0  0  0
  9  5  1  0  0  0  0
  9  6  1  0  0  0  0
 10  8  1  0  0  0  0
 11  7  1  0  0  0  0
 12  9  1  0  0  0  0
 13 10  2  0  0  0  0
 14  5  1  0  0  0  0
 14 10  1  0  0  0  0
M  END
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3D MOL for HMDB0030765 ((-)-trans-3,4-Dihydro-4,8-dihydroxy-3-methyl-1H-2-benzopyran-1-one)

HMDB0030765
     RDKit          3D
(-)-trans-3,4-Dihydro-4,8-dihydroxy-3-methyl-1H-2-benzopyran-1-one
 24 25  0  0  0  0  0  0  0  0999 V2000
   -2.6724   -0.7972    0.1869 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8298    0.0706    1.0700 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0243   -0.7629    1.8878 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2196   -1.2085    1.4555 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7540   -2.2109    1.9581 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8890   -0.4728    0.3949 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1415   -0.8733   -0.0907 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7977   -1.9520    0.3961 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7404   -0.1247   -1.1249 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0917    0.9692   -1.6295 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8675    1.3701   -1.1627 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2814    0.6402   -0.1528 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0314    1.0881    0.3422 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7628    1.5547   -0.7681 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6730   -1.0239    0.6399 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8905   -0.3357   -0.7944 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1567   -1.7602   -0.0230 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5233    0.6083    1.7678 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6325   -2.6007    1.0589 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6946   -0.4752   -1.4562 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5657    1.5316   -2.4225 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3707    2.2572   -1.5913 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8330    1.9988    0.9772 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6490    2.5092   -0.9191 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  2  0
  7  8  1  0
  7  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 13  2  1  0
 12  6  1  0
  1 15  1  0
  1 16  1  0
  1 17  1  0
  2 18  1  0
  8 19  1  0
  9 20  1  0
 10 21  1  0
 11 22  1  0
 13 23  1  0
 14 24  1  0
M  END
Download

3D SDF for HMDB0030765 ((-)-trans-3,4-Dihydro-4,8-dihydroxy-3-methyl-1H-2-benzopyran-1-one)

  Mrv0541 05061305292D          

 14 15  0  0  0  0            999 V2000
    5.0013    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  2  0  0  0  0
  4  2  1  0  0  0  0
  5  1  1  0  0  0  0
  6  3  1  0  0  0  0
  7  4  2  0  0  0  0
  8  6  2  0  0  0  0
  8  7  1  0  0  0  0
  9  5  1  0  0  0  0
  9  6  1  0  0  0  0
 10  8  1  0  0  0  0
 11  7  1  0  0  0  0
 12  9  1  0  0  0  0
 13 10  2  0  0  0  0
 14  5  1  0  0  0  0
 14 10  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0030765

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1OC(=O)C2=C(C=CC=C2O)C1O

> <INCHI_IDENTIFIER>
InChI=1S/C10H10O4/c1-5-9(12)6-3-2-4-7(11)8(6)10(13)14-5/h2-5,9,11-12H,1H3

> <INCHI_KEY>
STSOHAOGZMLWFR-UHFFFAOYSA-N

> <FORMULA>
C10H10O4

> <MOLECULAR_WEIGHT>
194.184

> <EXACT_MASS>
194.057908808

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
18.53012692437463

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4,8-dihydroxy-3-methyl-3,4-dihydro-1H-2-benzopyran-1-one

> <ALOGPS_LOGP>
0.92

> <JCHEM_LOGP>
1.6606248423333332

> <ALOGPS_LOGS>
-0.71

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.313602969278904

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.567712452623942

> <JCHEM_PKA_STRONGEST_BASIC>
-3.605892516568062

> <JCHEM_POLAR_SURFACE_AREA>
66.76

> <JCHEM_REFRACTIVITY>
49.0001

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.82e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4,8-dihydroxy-3-methyl-3,4-dihydro-2-benzopyran-1-one

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for HMDB0030765 ((-)-trans-3,4-Dihydro-4,8-dihydroxy-3-methyl-1H-2-benzopyran-1-one)

HMDB0030765
     RDKit          3D
(-)-trans-3,4-Dihydro-4,8-dihydroxy-3-methyl-1H-2-benzopyran-1-one
 24 25  0  0  0  0  0  0  0  0999 V2000
   -2.6724   -0.7972    0.1869 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8298    0.0706    1.0700 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0243   -0.7629    1.8878 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2196   -1.2085    1.4555 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7540   -2.2109    1.9581 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8890   -0.4728    0.3949 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1415   -0.8733   -0.0907 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7977   -1.9520    0.3961 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7404   -0.1247   -1.1249 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0917    0.9692   -1.6295 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8675    1.3701   -1.1627 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2814    0.6402   -0.1528 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0314    1.0881    0.3422 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7628    1.5547   -0.7681 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6730   -1.0239    0.6399 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8905   -0.3357   -0.7944 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1567   -1.7602   -0.0230 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5233    0.6083    1.7678 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6325   -2.6007    1.0589 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6946   -0.4752   -1.4562 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5657    1.5316   -2.4225 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3707    2.2572   -1.5913 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8330    1.9988    0.9772 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6490    2.5092   -0.9191 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  2  0
  7  8  1  0
  7  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 13  2  1  0
 12  6  1  0
  1 15  1  0
  1 16  1  0
  1 17  1  0
  2 18  1  0
  8 19  1  0
  9 20  1  0
 10 21  1  0
 11 22  1  0
 13 23  1  0
 14 24  1  0
M  END
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PDB for HMDB0030765 ((-)-trans-3,4-Dihydro-4,8-dihydroxy-3-methyl-1H-2-benzopyran-1-one)

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       9.336   2.310   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       4.001  -2.310   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       6.668   3.850   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0       6.668  -2.310   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0       8.002   0.000   0.000  0.00  0.00           O+0
CONECT    1    5                                                            
CONECT    2    3    4                                                       
CONECT    3    2    6                                                       
CONECT    4    2    7                                                       
CONECT    5    1    9   14                                                  
CONECT    6    3    8    9                                                  
CONECT    7    4    8   11                                                  
CONECT    8    6    7   10                                                  
CONECT    9    5    6   12                                                  
CONECT   10    8   13   14                                                  
CONECT   11    7                                                            
CONECT   12    9                                                            
CONECT   13   10                                                            
CONECT   14    5   10                                                       
MASTER        0    0    0    0    0    0    0    0   14    0   30    0
END
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3D PDB for HMDB0030765 ((-)-trans-3,4-Dihydro-4,8-dihydroxy-3-methyl-1H-2-benzopyran-1-one)

COMPND    HMDB0030765
HETATM    1  C1  UNL     1      -2.672  -0.797   0.187  1.00  0.00           C  
HETATM    2  C2  UNL     1      -1.830   0.071   1.070  1.00  0.00           C  
HETATM    3  O1  UNL     1      -1.024  -0.763   1.888  1.00  0.00           O  
HETATM    4  C3  UNL     1       0.220  -1.209   1.456  1.00  0.00           C  
HETATM    5  O2  UNL     1       0.754  -2.211   1.958  1.00  0.00           O  
HETATM    6  C4  UNL     1       0.889  -0.473   0.395  1.00  0.00           C  
HETATM    7  C5  UNL     1       2.142  -0.873  -0.091  1.00  0.00           C  
HETATM    8  O3  UNL     1       2.798  -1.952   0.396  1.00  0.00           O  
HETATM    9  C6  UNL     1       2.740  -0.125  -1.125  1.00  0.00           C  
HETATM   10  C7  UNL     1       2.092   0.969  -1.630  1.00  0.00           C  
HETATM   11  C8  UNL     1       0.867   1.370  -1.163  1.00  0.00           C  
HETATM   12  C9  UNL     1       0.281   0.640  -0.153  1.00  0.00           C  
HETATM   13  C10 UNL     1      -1.031   1.088   0.342  1.00  0.00           C  
HETATM   14  O4  UNL     1      -1.763   1.555  -0.768  1.00  0.00           O  
HETATM   15  H1  UNL     1      -3.673  -1.024   0.640  1.00  0.00           H  
HETATM   16  H2  UNL     1      -2.891  -0.336  -0.794  1.00  0.00           H  
HETATM   17  H3  UNL     1      -2.157  -1.760  -0.023  1.00  0.00           H  
HETATM   18  H4  UNL     1      -2.523   0.608   1.768  1.00  0.00           H  
HETATM   19  H5  UNL     1       2.633  -2.601   1.059  1.00  0.00           H  
HETATM   20  H6  UNL     1       3.695  -0.475  -1.456  1.00  0.00           H  
HETATM   21  H7  UNL     1       2.566   1.532  -2.422  1.00  0.00           H  
HETATM   22  H8  UNL     1       0.371   2.257  -1.591  1.00  0.00           H  
HETATM   23  H9  UNL     1      -0.833   1.999   0.977  1.00  0.00           H  
HETATM   24  H10 UNL     1      -1.649   2.509  -0.919  1.00  0.00           H  
CONECT    1    2   15   16   17
CONECT    2    3   13   18
CONECT    3    4
CONECT    4    5    5    6
CONECT    6    7    7   12
CONECT    7    8    9
CONECT    8   19
CONECT    9   10   10   20
CONECT   10   11   21
CONECT   11   12   12   22
CONECT   12   13
CONECT   13   14   23
CONECT   14   24
END
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SMILES for HMDB0030765 ((-)-trans-3,4-Dihydro-4,8-dihydroxy-3-methyl-1H-2-benzopyran-1-one)

CC1OC(=O)C2=C(C=CC=C2O)C1O
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INCHI for HMDB0030765 ((-)-trans-3,4-Dihydro-4,8-dihydroxy-3-methyl-1H-2-benzopyran-1-one)

InChI=1S/C10H10O4/c1-5-9(12)6-3-2-4-7(11)8(6)10(13)14-5/h2-5,9,11-12H,1H3
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View in JSmolView NMR AssignmentsView Stereo Labels
Synonyms
ValueSource
3-Methyl-4,8-dihydroxy-3,4-dihydroisocoumarinChEBI
4,8-Dihydroxy-3-methylbenzopyran-1-oneChEBI
trans-4-HydroxymelleinHMDB
Chemical FormulaC10H10O4
Average Molecular Weight194.184
Monoisotopic Molecular Weight194.057908808
IUPAC Name4,8-dihydroxy-3-methyl-3,4-dihydro-1H-2-benzopyran-1-one
Traditional Name4,8-dihydroxy-3-methyl-3,4-dihydro-2-benzopyran-1-one
CAS Registry Number70287-70-6
SMILES
CC1OC(=O)C2=C(C=CC=C2O)C1O
InChI Identifier
InChI=1S/C10H10O4/c1-5-9(12)6-3-2-4-7(11)8(6)10(13)14-5/h2-5,9,11-12H,1H3
InChI KeySTSOHAOGZMLWFR-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as 2-benzopyrans. These are organic aromatic compounds that 1-benzopyran, a bicyclic compound made up of a benzene ring fused to a pyran, so that the oxygen atom is at the 2-position.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassBenzopyrans
Sub Class2-benzopyrans
Direct Parent2-benzopyrans
Alternative Parents
Substituents
  • 2-benzopyran
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Benzenoid
  • Vinylogous acid
  • Carboxylic acid ester
  • Lactone
  • Secondary alcohol
  • Carboxylic acid derivative
  • Monocarboxylic acid or derivatives
  • Oxacycle
  • Organic oxygen compound
  • Organooxygen compound
  • Alcohol
  • Organic oxide
  • Hydrocarbon derivative
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
Biological locationRoute of exposureSource
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point131 - 132 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB002698
KNApSAcK IDC00000119
Chemspider ID148269
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound169539
PDB IDNot Available
ChEBI ID141335
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .