Showing metabocard for Cyclotene (MMDBc0033616)

Plant
Xenobiotic
Record Information
Version2.0
StatusDetected and Quantified
Creation Date2021-11-19 04:56:01 UTC
Update Date2025-10-07 16:08:01 UTC
Metabolite IDMMDBc0033616
Metabolite Identification
Common NameCyclotene
DescriptionCyclotene is a cyclopentenone, a class of organic compounds characterized by a five-membered ring containing a carbonyl group. Its chemical structure features a cyclopentene ring with a ketone functional group, specifically 2-hydroxy-3-methyl-2-cyclopenten-1-one. Cyclotene is involved in various biochemical pathways, including the fermentation process of soy sauce, where lactic acid bacteria influence its production alongside other compounds like furfural and methional (PMID:27939139 ). Additionally, it is released during the thermal processing of raw flaxen samples, contributing to the sweet and caramel volatile profile (PMID:33508608 ). Cyclotene's concentration can also vary with the toasting intensity of wood chips used in flavoring, where it is extracted along with other aroma compounds like maltol and guaiacol (PMID:37664949 ). Furthermore, in model systems containing soy hydrolyzed vegetable proteins, cyclotene is identified as a sugar-degraded compound, indicating its relevance in food chemistry (PMID:36778086 ). Overall, cyclotene plays a significant role in the aroma and flavor profile of various food products, highlighting its importance in both chemistry and culinary applications.
Structure
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for #<Metabolite:0x00007f9ac612f058>


  Mrv1652304272018552D          

  8  8  0  0  0  0            999 V2000
    0.4718   -1.4521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7018    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2169    0.6674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2169   -0.6674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5678    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5678   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2352    0.8974    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2352   -0.8974    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  4  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  3  5  1  0  0  0  0
  4  6  2  0  0  0  0
  5  6  1  0  0  0  0
  5  7  2  0  0  0  0
  6  8  1  0  0  0  0
M  END
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3D MOL for #<Metabolite:0x00007f9ac612f058>

HMDB0303163
     RDKit          3D
2-Hydroxy-3-methyl-2-cyclopenten-1-one
 16 16  0  0  0  0  0  0  0  0999 V2000
   -2.0098   -0.2421   -0.0603 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5043   -0.1009   -0.0719 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0875    0.9886    0.3870 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5233    2.1139    0.9213 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5227    0.7895    0.2278 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4341    1.6452    0.2052 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7581   -0.6743    0.0874 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4675   -1.0988   -0.5733 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2691   -1.0721   -0.7644 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3462   -0.4846    0.9672 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4007    0.7177   -0.4318 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3223    2.5711    0.4856 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7673   -1.1580    1.1006 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6527   -0.9079   -0.5021 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5176   -0.9618   -1.6824 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1683   -2.1255   -0.2956 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
  3  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  0
  8  2  1  0
  1  9  1  0
  1 10  1  0
  1 11  1  0
  4 12  1  0
  7 13  1  0
  7 14  1  0
  8 15  1  0
  8 16  1  0
M  END
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3D SDF for #<Metabolite:0x00007f9ac612f058>


  Mrv1652304272018552D          

  8  8  0  0  0  0            999 V2000
    0.4718   -1.4521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7018    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2169    0.6674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2169   -0.6674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5678    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5678   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2352    0.8974    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2352   -0.8974    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  4  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  3  5  1  0  0  0  0
  4  6  2  0  0  0  0
  5  6  1  0  0  0  0
  5  7  2  0  0  0  0
  6  8  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0033616

> <DATABASE_NAME>
MIME

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

> <INCHI_IDENTIFIER>
InChI=1S/C6H8O2/c1-4-2-3-5(7)6(4)8/h8H,2-3H2,1H3

> <INCHI_KEY>
CFAKWWQIUFSQFU-UHFFFAOYSA-N

> <FORMULA>
C6H8O2

> <MOLECULAR_WEIGHT>
112.1265

> <EXACT_MASS>
112.0524295

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
16

> <JCHEM_AVERAGE_POLARIZABILITY>
11.50257635004693

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-hydroxy-3-methylcyclopent-2-en-1-one

> <ALOGPS_LOGP>
-0.19

> <JCHEM_LOGP>
0.7661526796666664

> <ALOGPS_LOGS>
0.25

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.341905061635345

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6421107259681227

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
30.9891

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.98e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
cyclotene

> <JCHEM_VEBER_RULE>
1

$$$$
Download

3D-SDF for #<Metabolite:0x00007f9ac612f058>

HMDB0303163
     RDKit          3D
2-Hydroxy-3-methyl-2-cyclopenten-1-one
 16 16  0  0  0  0  0  0  0  0999 V2000
   -2.0098   -0.2421   -0.0603 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5043   -0.1009   -0.0719 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0875    0.9886    0.3870 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5233    2.1139    0.9213 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5227    0.7895    0.2278 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4341    1.6452    0.2052 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7581   -0.6743    0.0874 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4675   -1.0988   -0.5733 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2691   -1.0721   -0.7644 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3462   -0.4846    0.9672 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4007    0.7177   -0.4318 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3223    2.5711    0.4856 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7673   -1.1580    1.1006 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6527   -0.9079   -0.5021 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5176   -0.9618   -1.6824 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1683   -2.1255   -0.2956 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
  3  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  0
  8  2  1  0
  1  9  1  0
  1 10  1  0
  1 11  1  0
  4 12  1  0
  7 13  1  0
  7 14  1  0
  8 15  1  0
  8 16  1  0
M  END
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PDB for #<Metabolite:0x00007f9ac612f058>

HEADER    PROTEIN                                 27-APR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-APR-20         0                                  
HETATM    1  C   UNK     0       0.881  -2.711   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.310   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.405   1.246   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.405  -1.246   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.060   0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.060  -0.770   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -2.306   1.675   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0      -2.306  -1.675   0.000  0.00  0.00           O+0
CONECT    1    4                                                            
CONECT    2    3    4                                                       
CONECT    3    2    5                                                       
CONECT    4    1    2    6                                                  
CONECT    5    3    6    7                                                  
CONECT    6    4    5    8                                                  
CONECT    7    5                                                            
CONECT    8    6                                                            
MASTER        0    0    0    0    0    0    0    0    8    0   16    0
END
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3D PDB for #<Metabolite:0x00007f9ac612f058>

COMPND    HMDB0303163
HETATM    1  C1  UNL     1      -2.010  -0.242  -0.060  1.00  0.00           C  
HETATM    2  C2  UNL     1      -0.504  -0.101  -0.072  1.00  0.00           C  
HETATM    3  C3  UNL     1       0.087   0.989   0.387  1.00  0.00           C  
HETATM    4  O1  UNL     1      -0.523   2.114   0.921  1.00  0.00           O  
HETATM    5  C4  UNL     1       1.523   0.790   0.228  1.00  0.00           C  
HETATM    6  O2  UNL     1       2.434   1.645   0.205  1.00  0.00           O  
HETATM    7  C5  UNL     1       1.758  -0.674   0.087  1.00  0.00           C  
HETATM    8  C6  UNL     1       0.468  -1.099  -0.573  1.00  0.00           C  
HETATM    9  H1  UNL     1      -2.269  -1.072  -0.764  1.00  0.00           H  
HETATM   10  H2  UNL     1      -2.346  -0.485   0.967  1.00  0.00           H  
HETATM   11  H3  UNL     1      -2.401   0.718  -0.432  1.00  0.00           H  
HETATM   12  H4  UNL     1      -1.322   2.571   0.486  1.00  0.00           H  
HETATM   13  H5  UNL     1       1.767  -1.158   1.101  1.00  0.00           H  
HETATM   14  H6  UNL     1       2.653  -0.908  -0.502  1.00  0.00           H  
HETATM   15  H7  UNL     1       0.518  -0.962  -1.682  1.00  0.00           H  
HETATM   16  H8  UNL     1       0.168  -2.126  -0.296  1.00  0.00           H  
CONECT    1    2    9   10   11
CONECT    2    3    3    8
CONECT    3    4    5
CONECT    4   12
CONECT    5    6    6    7
CONECT    7    8   13   14
CONECT    8   15   16
END
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SMILES for #<Metabolite:0x00007f9ac612f058>

CC1=C(O)C(=O)CC1
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INCHI for #<Metabolite:0x00007f9ac612f058>

InChI=1S/C6H8O2/c1-4-2-3-5(7)6(4)8/h8H,2-3H2,1H3
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Synonyms
ValueSource
2-Hydroxy-1-methylcyclopenten-3-oneMeSH
CycloteneMeSH
Molecular FormulaC6H8O2
Average Mass112.1265
Monoisotopic Mass112.0524295
IUPAC Name2-hydroxy-3-methylcyclopent-2-en-1-one
Traditional Namecyclotene
CAS Registry Number80-71-7
SMILES
CC1=C(O)C(=O)CC1
InChI Identifier
InChI=1S/C6H8O2/c1-4-2-3-5(7)6(4)8/h8H,2-3H2,1H3
InChI KeyCFAKWWQIUFSQFU-UHFFFAOYSA-N