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Showing metabocard for xi-1,8,8-Trimethyl-2-oxabicyclo[3.2.1]octan-3-one (HMDB0037821)

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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 23:04:45 UTC
Update Date2022-03-07 02:55:31 UTC
HMDB IDHMDB0037821
Secondary Accession Numbers
  • HMDB37821
Metabolite Identification
Common Namexi-1,8,8-Trimethyl-2-oxabicyclo[3.2.1]octan-3-one
Descriptionxi-1,8,8-Trimethyl-2-oxabicyclo[3.2.1]octan-3-one belongs to the class of organic compounds known as lactones. These are cyclic esters of hydroxy carboxylic acids, containing a 1-oxacycloalkan-2-one structure, or analogues having unsaturation or heteroatoms replacing one or more carbon atoms of the ring. Thus, XI-1,8,8-trimethyl-2-oxabicyclo[3.2.1]octan-3-one is considered to be an isoprenoid. xi-1,8,8-Trimethyl-2-oxabicyclo[3.2.1]octan-3-one has been detected, but not quantified in, common sages (Salvia officinalis). This could make XI-1,8,8-trimethyl-2-oxabicyclo[3.2.1]octan-3-one a potential biomarker for the consumption of these foods. xi-1,8,8-Trimethyl-2-oxabicyclo[3.2.1]octan-3-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 very few articles have been published on xi-1,8,8-Trimethyl-2-oxabicyclo[3.2.1]octan-3-one.
Structure
Data?1563863093
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0037821 (xi-1,8,8-Trimethyl-2-oxabicyclo[3.2.1]octan-3-one)

  Mrv0541 05061310022D          

 12 13  0  0  0  0            999 V2000
    0.8111    0.6467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3203   -0.0281    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0569   -0.3464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7400   -1.2658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1197   -1.6427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9893   -0.5417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0605   -0.5572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1275   -1.3591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4999   -0.1173    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6396   -0.9304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5393   -2.0740    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6113   -0.9304    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  4  1  0  0  0  0
  7  4  1  0  0  0  0
  7  6  1  0  0  0  0
  8  6  1  0  0  0  0
  9  1  1  0  0  0  0
  9  2  1  0  0  0  0
  9  7  1  0  0  0  0
 10  3  1  0  0  0  0
 10  5  1  0  0  0  0
 10  9  1  0  0  0  0
 11  8  2  0  0  0  0
 12  8  1  0  0  0  0
 12 10  1  0  0  0  0
M  END
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3D MOL for HMDB0037821 (xi-1,8,8-Trimethyl-2-oxabicyclo[3.2.1]octan-3-one)

HMDB0037821
     RDKit          3D
xi-1,8,8-Trimethyl-2-oxabicyclo[3.2.1]octan-3-one
 28 29  0  0  0  0  0  0  0  0999 V2000
    0.1955    1.5450    1.7682 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4580    0.5503    0.7038 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1004    1.2117   -0.4953 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7905    0.3040   -1.6395 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1402   -0.7814   -1.1086 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7321   -1.9367   -0.6939 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6888   -1.4888    0.3537 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8133   -2.0478    0.4532 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2935   -0.4619    1.1843 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7585   -0.0788    0.0984 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7298    0.9224   -0.4655 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4887   -1.0103    0.9995 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1495    1.7015    2.3375 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0410    2.5582    1.3396 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5516    1.2375    2.5185 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1986    1.2704   -0.2661 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7507    2.2493   -0.6422 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7536   -0.1469   -1.9795 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2549    0.8025   -2.4626 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8855   -1.0812   -1.8480 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3502   -2.2063   -1.5909 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1738   -2.8355   -0.4012 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2094    0.4914   -1.3918 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5349    1.0840    0.2487 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2584    1.8583   -0.7842 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3437   -2.0587    0.7192 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6046   -0.8389    0.9918 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1569   -0.8134    2.0529 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  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  5 10  1  0
 10 11  1  0
 10 12  1  0
  9  2  1  0
 10  2  1  0
  1 13  1  0
  1 14  1  0
  1 15  1  0
  3 16  1  0
  3 17  1  0
  4 18  1  0
  4 19  1  0
  5 20  1  0
  6 21  1  0
  6 22  1  0
 11 23  1  0
 11 24  1  0
 11 25  1  0
 12 26  1  0
 12 27  1  0
 12 28  1  0
M  END
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3D SDF for HMDB0037821 (xi-1,8,8-Trimethyl-2-oxabicyclo[3.2.1]octan-3-one)

  Mrv0541 05061310022D          

 12 13  0  0  0  0            999 V2000
    0.8111    0.6467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3203   -0.0281    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0569   -0.3464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7400   -1.2658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1197   -1.6427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9893   -0.5417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0605   -0.5572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1275   -1.3591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4999   -0.1173    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6396   -0.9304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5393   -2.0740    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6113   -0.9304    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  4  1  0  0  0  0
  7  4  1  0  0  0  0
  7  6  1  0  0  0  0
  8  6  1  0  0  0  0
  9  1  1  0  0  0  0
  9  2  1  0  0  0  0
  9  7  1  0  0  0  0
 10  3  1  0  0  0  0
 10  5  1  0  0  0  0
 10  9  1  0  0  0  0
 11  8  2  0  0  0  0
 12  8  1  0  0  0  0
 12 10  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0037821

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1(C)C2CCC1(C)OC(=O)C2

> <INCHI_IDENTIFIER>
InChI=1S/C10H16O2/c1-9(2)7-4-5-10(9,3)12-8(11)6-7/h7H,4-6H2,1-3H3

> <INCHI_KEY>
AXRMSBLBSHJLGO-UHFFFAOYSA-N

> <FORMULA>
C10H16O2

> <MOLECULAR_WEIGHT>
168.2328

> <EXACT_MASS>
168.115029756

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
18.516679734534378

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1,8,8-trimethyl-2-oxabicyclo[3.2.1]octan-3-one

> <ALOGPS_LOGP>
2.70

> <JCHEM_LOGP>
1.9354922636666658

> <ALOGPS_LOGS>
-2.21

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-7.054193113258896

> <JCHEM_POLAR_SURFACE_AREA>
26.3

> <JCHEM_REFRACTIVITY>
45.5052

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.04e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1,2-campholide

> <JCHEM_VEBER_RULE>
1

$$$$
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3D-SDF for HMDB0037821 (xi-1,8,8-Trimethyl-2-oxabicyclo[3.2.1]octan-3-one)

HMDB0037821
     RDKit          3D
xi-1,8,8-Trimethyl-2-oxabicyclo[3.2.1]octan-3-one
 28 29  0  0  0  0  0  0  0  0999 V2000
    0.1955    1.5450    1.7682 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4580    0.5503    0.7038 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1004    1.2117   -0.4953 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7905    0.3040   -1.6395 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1402   -0.7814   -1.1086 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7321   -1.9367   -0.6939 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6888   -1.4888    0.3537 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8133   -2.0478    0.4532 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2935   -0.4619    1.1843 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7585   -0.0788    0.0984 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7298    0.9224   -0.4655 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4887   -1.0103    0.9995 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1495    1.7015    2.3375 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0410    2.5582    1.3396 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5516    1.2375    2.5185 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1986    1.2704   -0.2661 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7507    2.2493   -0.6422 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7536   -0.1469   -1.9795 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2549    0.8025   -2.4626 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8855   -1.0812   -1.8480 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3502   -2.2063   -1.5909 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1738   -2.8355   -0.4012 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2094    0.4914   -1.3918 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5349    1.0840    0.2487 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2584    1.8583   -0.7842 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3437   -2.0587    0.7192 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6046   -0.8389    0.9918 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1569   -0.8134    2.0529 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  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  5 10  1  0
 10 11  1  0
 10 12  1  0
  9  2  1  0
 10  2  1  0
  1 13  1  0
  1 14  1  0
  1 15  1  0
  3 16  1  0
  3 17  1  0
  4 18  1  0
  4 19  1  0
  5 20  1  0
  6 21  1  0
  6 22  1  0
 11 23  1  0
 11 24  1  0
 11 25  1  0
 12 26  1  0
 12 27  1  0
 12 28  1  0
M  END
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PDB for HMDB0037821 (xi-1,8,8-Trimethyl-2-oxabicyclo[3.2.1]octan-3-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       1.514   1.207   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.598  -0.052   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.106  -0.647   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.381  -2.363   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.223  -3.066   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.713  -1.011   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.980  -1.040   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.971  -2.537   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.933  -0.219   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.194  -1.737   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       4.740  -3.871   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       3.008  -1.737   0.000  0.00  0.00           O+0
CONECT    1    9                                                            
CONECT    2    9                                                            
CONECT    3   10                                                            
CONECT    4    5    7                                                       
CONECT    5    4   10                                                       
CONECT    6    7    8                                                       
CONECT    7    4    6    9                                                  
CONECT    8    6   11   12                                                  
CONECT    9    1    2    7   10                                             
CONECT   10    3    5    9   12                                             
CONECT   11    8                                                            
CONECT   12    8   10                                                       
MASTER        0    0    0    0    0    0    0    0   12    0   26    0
END
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3D PDB for HMDB0037821 (xi-1,8,8-Trimethyl-2-oxabicyclo[3.2.1]octan-3-one)

COMPND    HMDB0037821
HETATM    1  C1  UNL     1       0.195   1.545   1.768  1.00  0.00           C  
HETATM    2  C2  UNL     1       0.458   0.550   0.704  1.00  0.00           C  
HETATM    3  C3  UNL     1       1.100   1.212  -0.495  1.00  0.00           C  
HETATM    4  C4  UNL     1       0.790   0.304  -1.640  1.00  0.00           C  
HETATM    5  C5  UNL     1      -0.140  -0.781  -1.109  1.00  0.00           C  
HETATM    6  C6  UNL     1       0.732  -1.937  -0.694  1.00  0.00           C  
HETATM    7  C7  UNL     1       1.689  -1.489   0.354  1.00  0.00           C  
HETATM    8  O1  UNL     1       2.813  -2.048   0.453  1.00  0.00           O  
HETATM    9  O2  UNL     1       1.294  -0.462   1.184  1.00  0.00           O  
HETATM   10  C8  UNL     1      -0.758  -0.079   0.098  1.00  0.00           C  
HETATM   11  C9  UNL     1      -1.730   0.922  -0.466  1.00  0.00           C  
HETATM   12  C10 UNL     1      -1.489  -1.010   0.999  1.00  0.00           C  
HETATM   13  H1  UNL     1       1.149   1.702   2.337  1.00  0.00           H  
HETATM   14  H2  UNL     1      -0.041   2.558   1.340  1.00  0.00           H  
HETATM   15  H3  UNL     1      -0.552   1.237   2.519  1.00  0.00           H  
HETATM   16  H4  UNL     1       2.199   1.270  -0.266  1.00  0.00           H  
HETATM   17  H5  UNL     1       0.751   2.249  -0.642  1.00  0.00           H  
HETATM   18  H6  UNL     1       1.754  -0.147  -1.980  1.00  0.00           H  
HETATM   19  H7  UNL     1       0.255   0.803  -2.463  1.00  0.00           H  
HETATM   20  H8  UNL     1      -0.885  -1.081  -1.848  1.00  0.00           H  
HETATM   21  H9  UNL     1       1.350  -2.206  -1.591  1.00  0.00           H  
HETATM   22  H10 UNL     1       0.174  -2.835  -0.401  1.00  0.00           H  
HETATM   23  H11 UNL     1      -2.209   0.491  -1.392  1.00  0.00           H  
HETATM   24  H12 UNL     1      -2.535   1.084   0.249  1.00  0.00           H  
HETATM   25  H13 UNL     1      -1.258   1.858  -0.784  1.00  0.00           H  
HETATM   26  H14 UNL     1      -1.344  -2.059   0.719  1.00  0.00           H  
HETATM   27  H15 UNL     1      -2.605  -0.839   0.992  1.00  0.00           H  
HETATM   28  H16 UNL     1      -1.157  -0.813   2.053  1.00  0.00           H  
CONECT    1    2   13   14   15
CONECT    2    3    9   10
CONECT    3    4   16   17
CONECT    4    5   18   19
CONECT    5    6   10   20
CONECT    6    7   21   22
CONECT    7    8    8    9
CONECT   10   11   12
CONECT   11   23   24   25
CONECT   12   26   27   28
END
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SMILES for HMDB0037821 (xi-1,8,8-Trimethyl-2-oxabicyclo[3.2.1]octan-3-one)

CC1(C)C2CCC1(C)OC(=O)C2
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INCHI for HMDB0037821 (xi-1,8,8-Trimethyl-2-oxabicyclo[3.2.1]octan-3-one)

InChI=1S/C10H16O2/c1-9(2)7-4-5-10(9,3)12-8(11)6-7/h7H,4-6H2,1-3H3
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SynonymsNot Available
Chemical FormulaC10H16O2
Average Molecular Weight168.2328
Monoisotopic Molecular Weight168.115029756
IUPAC Name1,8,8-trimethyl-2-oxabicyclo[3.2.1]octan-3-one
Traditional Name1,2-campholide
CAS Registry NumberNot Available
SMILES
CC1(C)C2CCC1(C)OC(=O)C2
InChI Identifier
InChI=1S/C10H16O2/c1-9(2)7-4-5-10(9,3)12-8(11)6-7/h7H,4-6H2,1-3H3
InChI KeyAXRMSBLBSHJLGO-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as lactones. These are cyclic esters of hydroxy carboxylic acids, containing a 1-oxacycloalkan-2-one structure, or analogues having unsaturation or heteroatoms replacing one or more carbon atoms of the ring.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassLactones
Sub ClassNot Available
Direct ParentLactones
Alternative Parents
Substituents
  • Caprolactone
  • Delta valerolactone
  • Delta_valerolactone
  • Oxepane
  • Oxane
  • Carboxylic acid ester
  • Lactone
  • Carboxylic acid derivative
  • Oxacycle
  • Monocarboxylic acid or derivatives
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Biological locationSource
ProcessNot Available
RoleNot Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot 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
  • Membrane
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 IDFDB000811
KNApSAcK IDC00000834
Chemspider ID241485
KEGG Compound IDC02108
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound274476
PDB IDNot Available
ChEBI ID488
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.. .