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Showing metabocard for beta-Cyclocitral (HMDB0041011)

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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2012-09-12 02:38:34 UTC
Update Date2023-02-21 17:28:32 UTC
HMDB IDHMDB0041011
Secondary Accession Numbers
  • HMDB41011
Metabolite Identification
Common Namebeta-Cyclocitral
Descriptionbeta-Cyclocitral, also known as β-cyclocitral, belongs to the class of organic compounds known as organic oxides. These are organic compounds containing an oxide group. beta-Cyclocitral is a sweet, clean, and damascone tasting compound. beta-Cyclocitral is found, on average, in the highest concentration within orange mints (Mentha aquatica) and safflowers (Carthamus tinctorius). beta-Cyclocitral has also been detected, but not quantified in, several different foods, such as garden tomatoes (Solanum lycopersicum), garden tomato (var.), teas (Camellia sinensis), black tea, and cauliflowers (Brassica oleracea var. botrytis). This could make beta-cyclocitral a potential biomarker for the consumption of these foods. beta-Cyclocitral 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 small amount of articles have been published on beta-Cyclocitral.
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0041011 (beta-Cyclocitral)

  Mrv1652303202019002D          

 11 11  0  0  0  0            999 V2000
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1842    1.8695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2448    1.8695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    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
    1.4289    0.8250    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
    2.1434    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  4  1  0  0  0  0
  6  4  1  0  0  0  0
  8  1  1  0  0  0  0
  8  5  1  0  0  0  0
  9  7  1  0  0  0  0
  9  8  2  0  0  0  0
 10  2  1  0  0  0  0
 10  3  1  0  0  0  0
 10  6  1  0  0  0  0
 10  9  1  0  0  0  0
 11  7  2  0  0  0  0
M  END
Download

3D MOL for HMDB0041011 (beta-Cyclocitral)

HMDB0041011
     RDKit          3D
beta-Cyclocitral
 27 27  0  0  0  0  0  0  0  0999 V2000
    2.6620    0.8375    0.5329 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4353    0.0585    0.2443 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2715    0.6901    0.2478 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2538    2.1412    0.5397 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8379    2.7314    0.5426 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0297    0.0350   -0.0242 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0643    0.4662    0.9949 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5796    0.4496   -1.3918 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9527   -1.4738   -0.0166 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3209   -1.8819   -0.7232 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5458   -1.3851   -0.0348 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5527    0.1894    0.6575 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8390    1.5521   -0.2930 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5797    1.4243    1.4734 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1514    2.6856    0.7457 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7563   -0.3999    1.1878 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6294    0.7429    1.9575 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6872    1.3046    0.6416 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7494    0.5502   -2.1342 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1794    1.3887   -1.3078 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2402   -0.3566   -1.7868 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7840   -1.9312   -0.5910 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9862   -1.8816    1.0155 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2815   -1.4143   -1.7332 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3714   -2.9735   -0.8795 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8017   -1.9746    0.8737 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4096   -1.5745   -0.7387 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  3  6  1  0
  6  7  1  0
  6  8  1  0
  6  9  1  0
  9 10  1  0
 10 11  1  0
 11  2  1  0
  1 12  1  0
  1 13  1  0
  1 14  1  0
  4 15  1  0
  7 16  1  0
  7 17  1  0
  7 18  1  0
  8 19  1  0
  8 20  1  0
  8 21  1  0
  9 22  1  0
  9 23  1  0
 10 24  1  0
 10 25  1  0
 11 26  1  0
 11 27  1  0
M  END
Download

3D SDF for HMDB0041011 (beta-Cyclocitral)

  Mrv1652303202019002D          

 11 11  0  0  0  0            999 V2000
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1842    1.8695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2448    1.8695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    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
    1.4289    0.8250    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
    2.1434    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  4  1  0  0  0  0
  6  4  1  0  0  0  0
  8  1  1  0  0  0  0
  8  5  1  0  0  0  0
  9  7  1  0  0  0  0
  9  8  2  0  0  0  0
 10  2  1  0  0  0  0
 10  3  1  0  0  0  0
 10  6  1  0  0  0  0
 10  9  1  0  0  0  0
 11  7  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0041011

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1=C(C=O)C(C)(C)CCC1

> <INCHI_IDENTIFIER>
InChI=1S/C10H16O/c1-8-5-4-6-10(2,3)9(8)7-11/h7H,4-6H2,1-3H3

> <INCHI_KEY>
MOQGCGNUWBPGTQ-UHFFFAOYSA-N

> <FORMULA>
C10H16O

> <MOLECULAR_WEIGHT>
152.2334

> <EXACT_MASS>
152.120115134

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
27

> <JCHEM_AVERAGE_POLARIZABILITY>
18.032878736164943

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2,6,6-trimethylcyclohex-1-ene-1-carbaldehyde

> <ALOGPS_LOGP>
2.96

> <JCHEM_LOGP>
2.4123554396666664

> <ALOGPS_LOGS>
-2.08

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.3004482772850166

> <JCHEM_POLAR_SURFACE_AREA>
17.07

> <JCHEM_REFRACTIVITY>
47.1021

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.26e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
β-cyclocitral

> <JCHEM_VEBER_RULE>
1

$$$$
Download

3D-SDF for HMDB0041011 (beta-Cyclocitral)

HMDB0041011
     RDKit          3D
beta-Cyclocitral
 27 27  0  0  0  0  0  0  0  0999 V2000
    2.6620    0.8375    0.5329 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4353    0.0585    0.2443 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2715    0.6901    0.2478 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2538    2.1412    0.5397 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8379    2.7314    0.5426 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0297    0.0350   -0.0242 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0643    0.4662    0.9949 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5796    0.4496   -1.3918 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9527   -1.4738   -0.0166 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3209   -1.8819   -0.7232 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5458   -1.3851   -0.0348 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5527    0.1894    0.6575 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8390    1.5521   -0.2930 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5797    1.4243    1.4734 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1514    2.6856    0.7457 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7563   -0.3999    1.1878 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6294    0.7429    1.9575 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6872    1.3046    0.6416 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7494    0.5502   -2.1342 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1794    1.3887   -1.3078 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2402   -0.3566   -1.7868 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7840   -1.9312   -0.5910 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9862   -1.8816    1.0155 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2815   -1.4143   -1.7332 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3714   -2.9735   -0.8795 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8017   -1.9746    0.8737 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4096   -1.5745   -0.7387 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  3  6  1  0
  6  7  1  0
  6  8  1  0
  6  9  1  0
  9 10  1  0
 10 11  1  0
 11  2  1  0
  1 12  1  0
  1 13  1  0
  1 14  1  0
  4 15  1  0
  7 16  1  0
  7 17  1  0
  7 18  1  0
  8 19  1  0
  8 20  1  0
  8 21  1  0
  9 22  1  0
  9 23  1  0
 10 24  1  0
 10 25  1  0
 11 26  1  0
 11 27  1  0
M  END
Download

PDB for HMDB0041011 (beta-Cyclocitral)

HEADER    PROTEIN                                 20-MAR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-MAR-20         0                                  
HETATM    1  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.344   3.490   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.324   3.490   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       4.001   3.850   0.000  0.00  0.00           O+0
CONECT    1    8                                                            
CONECT    2   10                                                            
CONECT    3   10                                                            
CONECT    4    5    6                                                       
CONECT    5    4    8                                                       
CONECT    6    4   10                                                       
CONECT    7    9   11                                                       
CONECT    8    1    5    9                                                  
CONECT    9    7    8   10                                                  
CONECT   10    2    3    6    9                                             
CONECT   11    7                                                            
MASTER        0    0    0    0    0    0    0    0   11    0   22    0
END
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3D PDB for HMDB0041011 (beta-Cyclocitral)

COMPND    HMDB0041011
HETATM    1  C1  UNL     1       2.662   0.837   0.533  1.00  0.00           C  
HETATM    2  C2  UNL     1       1.435   0.058   0.244  1.00  0.00           C  
HETATM    3  C3  UNL     1       0.272   0.690   0.248  1.00  0.00           C  
HETATM    4  C4  UNL     1       0.254   2.141   0.540  1.00  0.00           C  
HETATM    5  O1  UNL     1      -0.838   2.731   0.543  1.00  0.00           O  
HETATM    6  C5  UNL     1      -1.030   0.035  -0.024  1.00  0.00           C  
HETATM    7  C6  UNL     1      -2.064   0.466   0.995  1.00  0.00           C  
HETATM    8  C7  UNL     1      -1.580   0.450  -1.392  1.00  0.00           C  
HETATM    9  C8  UNL     1      -0.953  -1.474  -0.017  1.00  0.00           C  
HETATM   10  C9  UNL     1       0.321  -1.882  -0.723  1.00  0.00           C  
HETATM   11  C10 UNL     1       1.546  -1.385  -0.035  1.00  0.00           C  
HETATM   12  H1  UNL     1       3.553   0.189   0.657  1.00  0.00           H  
HETATM   13  H2  UNL     1       2.839   1.552  -0.293  1.00  0.00           H  
HETATM   14  H3  UNL     1       2.580   1.424   1.473  1.00  0.00           H  
HETATM   15  H4  UNL     1       1.151   2.686   0.746  1.00  0.00           H  
HETATM   16  H5  UNL     1      -2.756  -0.400   1.188  1.00  0.00           H  
HETATM   17  H6  UNL     1      -1.629   0.743   1.957  1.00  0.00           H  
HETATM   18  H7  UNL     1      -2.687   1.305   0.642  1.00  0.00           H  
HETATM   19  H8  UNL     1      -0.749   0.550  -2.134  1.00  0.00           H  
HETATM   20  H9  UNL     1      -2.179   1.389  -1.308  1.00  0.00           H  
HETATM   21  H10 UNL     1      -2.240  -0.357  -1.787  1.00  0.00           H  
HETATM   22  H11 UNL     1      -1.784  -1.931  -0.591  1.00  0.00           H  
HETATM   23  H12 UNL     1      -0.986  -1.882   1.016  1.00  0.00           H  
HETATM   24  H13 UNL     1       0.281  -1.414  -1.733  1.00  0.00           H  
HETATM   25  H14 UNL     1       0.371  -2.973  -0.880  1.00  0.00           H  
HETATM   26  H15 UNL     1       1.802  -1.975   0.874  1.00  0.00           H  
HETATM   27  H16 UNL     1       2.410  -1.575  -0.739  1.00  0.00           H  
CONECT    1    2   12   13   14
CONECT    2    3    3   11
CONECT    3    4    6
CONECT    4    5    5   15
CONECT    6    7    8    9
CONECT    7   16   17   18
CONECT    8   19   20   21
CONECT    9   10   22   23
CONECT   10   11   24   25
CONECT   11   26   27
END
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SMILES for HMDB0041011 (beta-Cyclocitral)

CC1=C(C=O)C(C)(C)CCC1
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INCHI for HMDB0041011 (beta-Cyclocitral)

InChI=1S/C10H16O/c1-8-5-4-6-10(2,3)9(8)7-11/h7H,4-6H2,1-3H3
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View in JSmolView Stereo Labels
Synonyms
ValueSource
2,6,6-Trimethyl-1-cyclohexene-1-carboxaldehydeChEBI
2,6,6-Trimethyl-1-cyclohexene-1-carbaldehydeKegg
b-CyclocitralGenerator
Β-cyclocitralGenerator
1-Formyl-2,6,6-trimethyl-1-cyclohexeneHMDB
2,6,6-Trimethyl-1-cyclohexen-1-carboxaldehydeHMDB
2,6,6-Trimethyl-cyclohexene-1-carboxaldehydeHMDB
2,6,6-Trimethyl-cyclohexenecarboxaldehydeHMDB
2,6,6-Trimethylcyclohex-1-ene-1-carbaldehydeHMDB
2,6,6-Trimethylcyclohexene-1-carbaldehydeHMDB
2,6,6-TrimethylcyclohexenecarbaldehydeHMDB
alpha(beta)-CyclocitralHMDB
beta -CyclocitralHMDB
beta-CyclocitrolHMDB
Chemical FormulaC10H16O
Average Molecular Weight152.2334
Monoisotopic Molecular Weight152.120115134
IUPAC Name2,6,6-trimethylcyclohex-1-ene-1-carbaldehyde
Traditional Nameβ-cyclocitral
CAS Registry Number432-25-7
SMILES
CC1=C(C=O)C(C)(C)CCC1
InChI Identifier
InChI=1S/C10H16O/c1-8-5-4-6-10(2,3)9(8)7-11/h7H,4-6H2,1-3H3
InChI KeyMOQGCGNUWBPGTQ-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as organic oxides. These are organic compounds containing an oxide group.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganic oxides
Sub ClassNot Available
Direct ParentOrganic oxides
Alternative Parents
Substituents
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aldehyde
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External Descriptors
Ontology
Physiological effect
Organoleptic effect
Disposition
Biological locationRoute of exposureSource
ProcessNot Available
Role
Industrial applicationBiological role
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling Point62.00 to 63.00 °C. @ 3.00 mm HgThe Good Scents Company Information System
Water Solubility86.14 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP3.100 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular Locations
  • Membrane
Biospecimen Locations
  • Feces
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Nonalcoholic fatty liver disease (NAFLD)		 details
Associated Disorders and Diseases
Disease References
Nonalcoholic fatty liver disease
  1. Raman M, Ahmed I, Gillevet PM, Probert CS, Ratcliffe NM, Smith S, Greenwood R, Sikaroodi M, Lam V, Crotty P, Bailey J, Myers RP, Rioux KP: Fecal microbiome and volatile organic compound metabolome in obese humans with nonalcoholic fatty liver disease. Clin Gastroenterol Hepatol. 2013 Jul;11(7):868-75.e1-3. doi: 10.1016/j.cgh.2013.02.015. Epub 2013 Feb 27. [PubMed:23454028 ]
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB020874
KNApSAcK IDC00042278
Chemspider ID9511
KEGG Compound IDC20425
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound9895
PDB IDNot Available
ChEBI ID53177
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1037211
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.. .