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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 21:13:06 UTC

Update Date

2022-03-07 02:54:48 UTC

HMDB ID

HMDB0036155

Secondary Accession Numbers

HMDB36155

Metabolite Identification

Common Name

Curzerenone

Description

Curzerenone belongs to the class of organic compounds known as aromatic monoterpenoids. These are monoterpenoids containing at least one aromatic ring. Based on a literature review a significant number of articles have been published on Curzerenone.

Structure

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

HMDB0036155
     RDKit          3D
Curzerenone
 35 36  0  0  0  0  0  0  0  0999 V2000
   -1.9803   -1.3461    1.9956 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0057   -0.6645    1.3651 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9725   -0.6964   -0.1235 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4169   -0.8289   -0.5898 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2073   -1.8380   -0.6441 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2582   -1.6767   -0.6096 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2752   -2.4799   -0.7983 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4192   -1.8636   -0.6570 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1806   -0.5456   -0.3501 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1025    0.5582   -0.0932 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7822   -0.4382   -0.3226 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9288    0.7255   -0.0482 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4373    1.6487    0.5949 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4362    0.6516   -0.5746 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2981    1.7733   -0.2631 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7735    2.5271   -1.2369 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7022    2.1569    1.1368 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7276   -1.9073    1.4519 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0558   -1.3603    3.0724 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2959   -0.1298    1.9555 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4677   -0.3772   -1.6006 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6207   -1.9117   -0.6825 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1353   -0.4203    0.1174 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5032   -2.1376   -1.6761 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4466   -2.7415   -0.0111 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3747   -2.3512   -0.7721 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7355    1.2436    0.6931 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1108    0.2221    0.2491 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1857    1.1637   -1.0246 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3384    0.5562   -1.6795 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5099    2.2928   -2.2555 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4156    3.3696   -1.0630 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1574    3.1689    1.1655 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8314    2.2008    1.8173 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4925    1.4556    1.4615 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
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
  9 11  1  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  1  0
 15 16  2  3
 15 17  1  0
 14  3  1  0
 11  6  2  0
  1 18  1  0
  1 19  1  0
  2 20  1  0
  4 21  1  0
  4 22  1  0
  4 23  1  0
  5 24  1  0
  5 25  1  0
  8 26  1  0
 10 27  1  0
 10 28  1  0
 10 29  1  0
 14 30  1  0
 16 31  1  0
 16 32  1  0
 17 33  1  0
 17 34  1  0
 17 35  1  0
M  END

  Mrv0541 05061308542D          

 17 18  0  0  0  0            999 V2000
    4.6951    0.2033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668   -2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8838   -2.1500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6345    0.4898    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1648   -0.4287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538   -0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387   -1.3654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -2.3479    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387   -0.0305    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  6  1  2  0  0  0  0
  9  2  2  0  0  0  0
  9  3  1  0  0  0  0
 10  4  1  0  0  0  0
 10  8  2  0  0  0  0
 11  7  1  0  0  0  0
 12 10  1  0  0  0  0
 12 11  2  0  0  0  0
 13  9  1  0  0  0  0
 14 12  1  0  0  0  0
 14 13  1  0  0  0  0
 15  5  1  0  0  0  0
 15  6  1  0  0  0  0
 15  7  1  0  0  0  0
 15 13  1  0  0  0  0
 16 14  2  0  0  0  0
 17  8  1  0  0  0  0
 17 11  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0036155

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(=C)C1C(=O)C2=C(CC1(C)C=C)OC=C2C

> <INCHI_IDENTIFIER>
InChI=1S/C15H18O2/c1-6-15(5)7-11-12(10(4)8-17-11)14(16)13(15)9(2)3/h6,8,13H,1-2,7H2,3-5H3

> <INCHI_KEY>
ZVMJXSJCBLRAPD-UHFFFAOYSA-N

> <FORMULA>
C15H18O2

> <MOLECULAR_WEIGHT>
230.3022

> <EXACT_MASS>
230.13067982

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
25.990784828530842

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
6-ethenyl-3,6-dimethyl-5-(prop-1-en-2-yl)-4,5,6,7-tetrahydro-1-benzofuran-4-one

> <ALOGPS_LOGP>
3.60

> <JCHEM_LOGP>
3.3534603653333335

> <ALOGPS_LOGS>
-3.75

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
18.612283172663727

> <JCHEM_PKA_STRONGEST_BASIC>
-3.516580417203723

> <JCHEM_POLAR_SURFACE_AREA>
30.21

> <JCHEM_REFRACTIVITY>
69.0832

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.07e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
6-ethenyl-3,6-dimethyl-5-(prop-1-en-2-yl)-5,7-dihydro-1-benzofuran-4-one

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0036155
     RDKit          3D
Curzerenone
 35 36  0  0  0  0  0  0  0  0999 V2000
   -1.9803   -1.3461    1.9956 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0057   -0.6645    1.3651 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9725   -0.6964   -0.1235 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4169   -0.8289   -0.5898 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2073   -1.8380   -0.6441 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2582   -1.6767   -0.6096 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2752   -2.4799   -0.7983 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4192   -1.8636   -0.6570 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1806   -0.5456   -0.3501 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1025    0.5582   -0.0932 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7822   -0.4382   -0.3226 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9288    0.7255   -0.0482 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4373    1.6487    0.5949 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4362    0.6516   -0.5746 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2981    1.7733   -0.2631 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7735    2.5271   -1.2369 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7022    2.1569    1.1368 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7276   -1.9073    1.4519 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0558   -1.3603    3.0724 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2959   -0.1298    1.9555 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4677   -0.3772   -1.6006 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6207   -1.9117   -0.6825 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1353   -0.4203    0.1174 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5032   -2.1376   -1.6761 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4466   -2.7415   -0.0111 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3747   -2.3512   -0.7721 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7355    1.2436    0.6931 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1108    0.2221    0.2491 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1857    1.1637   -1.0246 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3384    0.5562   -1.6795 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5099    2.2928   -2.2555 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4156    3.3696   -1.0630 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1574    3.1689    1.1655 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8314    2.2008    1.8173 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4925    1.4556    1.4615 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
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
  9 11  1  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  1  0
 15 16  2  3
 15 17  1  0
 14  3  1  0
 11  6  2  0
  1 18  1  0
  1 19  1  0
  2 20  1  0
  4 21  1  0
  4 22  1  0
  4 23  1  0
  5 24  1  0
  5 25  1  0
  8 26  1  0
 10 27  1  0
 10 28  1  0
 10 29  1  0
 14 30  1  0
 16 31  1  0
 16 32  1  0
 17 33  1  0
 17 34  1  0
 17 35  1  0
M  END

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       8.764   0.379   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.925  -2.073   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.591  -4.383   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.650  -4.013   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.784   0.914   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.774  -0.800   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.924   0.237   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.220  -1.303   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.591  -2.843   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.126  -2.549   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.590  -0.533   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.590  -2.073   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.258  -2.073   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.924  -2.843   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.258  -0.533   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       4.924  -4.383   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       2.126  -0.057   0.000  0.00  0.00           O+0
CONECT    1    6                                                            
CONECT    2    9                                                            
CONECT    3    9                                                            
CONECT    4   10                                                            
CONECT    5   15                                                            
CONECT    6    1   15                                                       
CONECT    7   11   15                                                       
CONECT    8   10   17                                                       
CONECT    9    2    3   13                                                  
CONECT   10    4    8   12                                                  
CONECT   11    7   12   17                                                  
CONECT   12   10   11   14                                                  
CONECT   13    9   14   15                                                  
CONECT   14   12   13   16                                                  
CONECT   15    5    6    7   13                                             
CONECT   16   14                                                            
CONECT   17    8   11                                                       
MASTER        0    0    0    0    0    0    0    0   17    0   36    0
END

COMPND    HMDB0036155
HETATM    1  C1  UNL     1      -1.980  -1.346   1.996  1.00  0.00           C  
HETATM    2  C2  UNL     1      -1.006  -0.665   1.365  1.00  0.00           C  
HETATM    3  C3  UNL     1      -0.973  -0.696  -0.124  1.00  0.00           C  
HETATM    4  C4  UNL     1      -2.417  -0.829  -0.590  1.00  0.00           C  
HETATM    5  C5  UNL     1      -0.207  -1.838  -0.644  1.00  0.00           C  
HETATM    6  C6  UNL     1       1.258  -1.677  -0.610  1.00  0.00           C  
HETATM    7  O1  UNL     1       2.275  -2.480  -0.798  1.00  0.00           O  
HETATM    8  C7  UNL     1       3.419  -1.864  -0.657  1.00  0.00           C  
HETATM    9  C8  UNL     1       3.181  -0.546  -0.350  1.00  0.00           C  
HETATM   10  C9  UNL     1       4.103   0.558  -0.093  1.00  0.00           C  
HETATM   11  C10 UNL     1       1.782  -0.438  -0.323  1.00  0.00           C  
HETATM   12  C11 UNL     1       0.929   0.725  -0.048  1.00  0.00           C  
HETATM   13  O2  UNL     1       1.437   1.649   0.595  1.00  0.00           O  
HETATM   14  C12 UNL     1      -0.436   0.652  -0.575  1.00  0.00           C  
HETATM   15  C13 UNL     1      -1.298   1.773  -0.263  1.00  0.00           C  
HETATM   16  C14 UNL     1      -1.774   2.527  -1.237  1.00  0.00           C  
HETATM   17  C15 UNL     1      -1.702   2.157   1.137  1.00  0.00           C  
HETATM   18  H1  UNL     1      -2.728  -1.907   1.452  1.00  0.00           H  
HETATM   19  H2  UNL     1      -2.056  -1.360   3.072  1.00  0.00           H  
HETATM   20  H3  UNL     1      -0.296  -0.130   1.955  1.00  0.00           H  
HETATM   21  H4  UNL     1      -2.468  -0.377  -1.601  1.00  0.00           H  
HETATM   22  H5  UNL     1      -2.621  -1.912  -0.683  1.00  0.00           H  
HETATM   23  H6  UNL     1      -3.135  -0.420   0.117  1.00  0.00           H  
HETATM   24  H7  UNL     1      -0.503  -2.138  -1.676  1.00  0.00           H  
HETATM   25  H8  UNL     1      -0.447  -2.741  -0.011  1.00  0.00           H  
HETATM   26  H9  UNL     1       4.375  -2.351  -0.772  1.00  0.00           H  
HETATM   27  H10 UNL     1       3.736   1.244   0.693  1.00  0.00           H  
HETATM   28  H11 UNL     1       5.111   0.222   0.249  1.00  0.00           H  
HETATM   29  H12 UNL     1       4.186   1.164  -1.025  1.00  0.00           H  
HETATM   30  H13 UNL     1      -0.338   0.556  -1.679  1.00  0.00           H  
HETATM   31  H14 UNL     1      -1.510   2.293  -2.255  1.00  0.00           H  
HETATM   32  H15 UNL     1      -2.416   3.370  -1.063  1.00  0.00           H  
HETATM   33  H16 UNL     1      -2.157   3.169   1.166  1.00  0.00           H  
HETATM   34  H17 UNL     1      -0.831   2.201   1.817  1.00  0.00           H  
HETATM   35  H18 UNL     1      -2.493   1.456   1.462  1.00  0.00           H  
CONECT    1    2    2   18   19
CONECT    2    3   20
CONECT    3    4    5   14
CONECT    4   21   22   23
CONECT    5    6   24   25
CONECT    6    7   11   11
CONECT    7    8
CONECT    8    9    9   26
CONECT    9   10   11
CONECT   10   27   28   29
CONECT   11   12
CONECT   12   13   13   14
CONECT   14   15   30
CONECT   15   16   16   17
CONECT   16   31   32
CONECT   17   33   34   35
END

HMDB0036155
     RDKit          3D
Curzerenone
 35 36  0  0  0  0  0  0  0  0999 V2000
   -1.9803   -1.3461    1.9956 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0057   -0.6645    1.3651 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9725   -0.6964   -0.1235 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4169   -0.8289   -0.5898 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2073   -1.8380   -0.6441 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2582   -1.6767   -0.6096 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2752   -2.4799   -0.7983 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4192   -1.8636   -0.6570 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1806   -0.5456   -0.3501 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1025    0.5582   -0.0932 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7822   -0.4382   -0.3226 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9288    0.7255   -0.0482 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4373    1.6487    0.5949 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4362    0.6516   -0.5746 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2981    1.7733   -0.2631 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7735    2.5271   -1.2369 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7022    2.1569    1.1368 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7276   -1.9073    1.4519 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0558   -1.3603    3.0724 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2959   -0.1298    1.9555 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4677   -0.3772   -1.6006 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6207   -1.9117   -0.6825 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1353   -0.4203    0.1174 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5032   -2.1376   -1.6761 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4466   -2.7415   -0.0111 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3747   -2.3512   -0.7721 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7355    1.2436    0.6931 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1108    0.2221    0.2491 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1857    1.1637   -1.0246 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3384    0.5562   -1.6795 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5099    2.2928   -2.2555 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4156    3.3696   -1.0630 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1574    3.1689    1.1655 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8314    2.2008    1.8173 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4925    1.4556    1.4615 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
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
  9 11  1  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  1  0
 15 16  2  3
 15 17  1  0
 14  3  1  0
 11  6  2  0
  1 18  1  0
  1 19  1  0
  2 20  1  0
  4 21  1  0
  4 22  1  0
  4 23  1  0
  5 24  1  0
  5 25  1  0
  8 26  1  0
 10 27  1  0
 10 28  1  0
 10 29  1  0
 14 30  1  0
 16 31  1  0
 16 32  1  0
 17 33  1  0
 17 34  1  0
 17 35  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Zedoarone	HMDB

Chemical Formula

C₁₅H₁₈O₂

Average Molecular Weight

230.3022

Monoisotopic Molecular Weight

230.13067982

IUPAC Name

6-ethenyl-3,6-dimethyl-5-(prop-1-en-2-yl)-4,5,6,7-tetrahydro-1-benzofuran-4-one

Traditional Name

6-ethenyl-3,6-dimethyl-5-(prop-1-en-2-yl)-5,7-dihydro-1-benzofuran-4-one

CAS Registry Number

20493-56-5

SMILES

CC(=C)C1C(=O)C2=C(CC1(C)C=C)OC=C2C

InChI Identifier

InChI=1S/C15H18O2/c1-6-15(5)7-11-12(10(4)8-17-11)14(16)13(15)9(2)3/h6,8,13H,1-2,7H2,3-5H3

InChI Key

ZVMJXSJCBLRAPD-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as aromatic monoterpenoids. These are monoterpenoids containing at least one aromatic ring.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Monoterpenoids

Direct Parent

Aromatic monoterpenoids

Alternative Parents

Substituents

Menthofuran monoterpenoid
Aromatic monoterpenoid
Bicyclic monoterpenoid
Benzofuran
Aryl ketone
Aryl alkyl ketone
Furan
Heteroaromatic compound
Ketone
Oxacycle
Organoheterocyclic compound
Organic oxygen compound
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Route of exposure

Enteral

Ingestion (HMDB: HMDB0036155)

Source

Exogenous

Exogenous (HMDB: HMDB0036155)

Food

Food (HMDB: HMDB0036155)

Herb and spice

Spice

Turmeric (FooDB: FOOD00068)

Endogenous

Endogenous (HMDB: HMDB0036155)

Animal

Animal (HMDB: HMDB0036155)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0036155)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0036155)

Lipid metabolism pathway (HMDB: HMDB0036155)

Cellular process

Cell signaling (HMDB: HMDB0036155)

Biochemical process

Lipid transport (HMDB: HMDB0036155)

Role

Biological role

Energy source (HMDB: HMDB0036155)

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	320.00 to 321.00 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Water Solubility	1.44 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	0.315 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.041 g/L	ALOGPS
logP	3.6	ALOGPS
logP	3.35	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Acidic)	18.61	ChemAxon
pKa (Strongest Basic)	-3.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	30.21 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	69.08 m³·mol⁻¹	ChemAxon
Polarizability	25.99 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	152.443	31661259
DarkChem	[M-H]-	149.81	31661259
DeepCCS	[M+H]+	155.316	30932474
DeepCCS	[M-H]-	152.958	30932474
DeepCCS	[M-2H]-	186.192	30932474
DeepCCS	[M+Na]+	161.409	30932474
AllCCS	[M+H]+	150.4	32859911
AllCCS	[M+H-H2O]+	146.5	32859911
AllCCS	[M+NH4]+	154.1	32859911
AllCCS	[M+Na]+	155.1	32859911
AllCCS	[M-H]-	157.7	32859911
AllCCS	[M+Na-2H]-	157.6	32859911
AllCCS	[M+HCOO]-	157.7	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Curzerenone	CC(=C)C1C(=O)C2=C(CC1(C)C=C)OC=C2C	2232.7	Standard polar	33892256
Curzerenone	CC(=C)C1C(=O)C2=C(CC1(C)C=C)OC=C2C	1673.3	Standard non polar	33892256
Curzerenone	CC(=C)C1C(=O)C2=C(CC1(C)C=C)OC=C2C	1612.6	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Curzerenone GC-MS (Non-derivatized) - 70eV, Positive	splash10-004i-9530000000-5ce127ab411f7b319d4f	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Curzerenone GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Curzerenone GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Curzerenone 10V, Positive-QTOF	splash10-001i-0190000000-ac2e3fde2c9d43ceb56e	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Curzerenone 20V, Positive-QTOF	splash10-0fsm-6960000000-18f3d545eb8ff6645f89	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Curzerenone 40V, Positive-QTOF	splash10-0uxr-9200000000-4000e91bc6bbbfebfe8b	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Curzerenone 10V, Negative-QTOF	splash10-004i-0090000000-98523e97b271e04856d4	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Curzerenone 20V, Negative-QTOF	splash10-004i-0290000000-203d2685f68ba5b1b43e	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Curzerenone 40V, Negative-QTOF	splash10-007t-4910000000-c484fc471fbe855a0e55	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Curzerenone 10V, Positive-QTOF	splash10-001i-0090000000-c656b3b03b821390fc7a	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Curzerenone 20V, Positive-QTOF	splash10-001i-7950000000-21dcf4dda75619d25359	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Curzerenone 40V, Positive-QTOF	splash10-000m-9200000000-e653b399f864f5e7132b	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Curzerenone 10V, Negative-QTOF	splash10-004i-0090000000-fb2ff0c6ce4213f1f376	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Curzerenone 20V, Negative-QTOF	splash10-004i-0290000000-b7fbbb4e9bc022dabbcc	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Curzerenone 40V, Negative-QTOF	splash10-01p9-3930000000-591264b61acf25ee00fd	2021-09-23	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane

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

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Curzerenone

METLIN ID

Not Available

PubChem Compound

5315433

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1389501

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Showing metabocard for Curzerenone (HMDB0036155)

MOL for HMDB0036155 (Curzerenone)

3D MOL for HMDB0036155 (Curzerenone)

3D SDF for HMDB0036155 (Curzerenone)

3D-SDF for HMDB0036155 (Curzerenone)

PDB for HMDB0036155 (Curzerenone)

3D PDB for HMDB0036155 (Curzerenone)

SMILES for HMDB0036155 (Curzerenone)

INCHI for HMDB0036155 (Curzerenone)

Structure for HMDB0036155 (Curzerenone)

3D Structure for HMDB0036155 (Curzerenone)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra