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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 18:39:04 UTC

Update Date

2022-03-07 02:53:53 UTC

HMDB ID

HMDB0033878

Secondary Accession Numbers

HMDB33878

Metabolite Identification

Common Name

(S)-Curzeone

Description

(S)-Curzeone belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. Based on a literature review a small amount of articles have been published on (S)-Curzeone.

Structure

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

HMDB0033878
     RDKit          3D
(S)-Curzeone
 33 35  0  0  0  0  0  0  0  0999 V2000
    3.5688    0.3699    0.8076 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2029    0.7746    0.4375 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7756    2.1020    0.5457 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4870    2.4484    0.1919 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1856    3.5586    0.1837 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4031    3.3900   -0.2373 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5967    2.0370   -0.5515 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8772    1.4688   -1.0065 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3908    1.4471   -0.2804 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0395    0.1564   -0.3843 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3507   -0.1842   -0.0191 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6417   -1.6319   -0.1720 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5054   -2.3501    0.5344 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7497   -2.2235   -0.2620 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0038   -2.3954    0.5696 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8075   -0.9059   -0.9425 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4972   -0.6265   -1.9342 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1630    0.0068   -0.0724 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0996    1.2676    1.1900 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5840   -0.3719    1.6421 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4405    2.8738    0.9049 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1937    4.1219   -0.3538 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0165    1.4455   -2.0882 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7225    2.1949   -0.6601 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2030    0.5512   -0.4642 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5948   -1.9217   -1.2435 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6272   -1.9166    0.2037 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7456   -3.4438    0.6756 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3873   -1.9626    1.5789 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7352   -2.9954   -1.0561 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2738   -1.4044    0.9706 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7992   -2.7760   -0.0931 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7582   -3.1048    1.3849 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  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  1  0
 16 17  2  0
 11  2  1  0
  9  4  2  0
 16 10  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  3 21  1  0
  6 22  1  0
  8 23  1  0
  8 24  1  0
  8 25  1  0
 12 26  1  0
 12 27  1  0
 13 28  1  0
 13 29  1  0
 14 30  1  0
 15 31  1  0
 15 32  1  0
 15 33  1  0
M  END


  Mrv0541 05061307252D          

 17 19  0  0  0  0            999 V2000
    1.2742   -0.9900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6226    2.5420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1286   -1.0703    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3188    0.4383    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7534    1.1395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8372    1.7892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0890    0.0428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7088   -0.2887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0126    1.8150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3252   -0.2691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5780    1.1137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2272    1.0622    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7926    0.3610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9680    0.3867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5334   -0.3145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9234   -1.0415    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0284    0.8656    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  4  1  0  0  0  0
  8  1  1  0  0  0  0
  8  4  1  0  0  0  0
  9  2  1  0  0  0  0
  9  6  2  0  0  0  0
 10  3  1  0  0  0  0
 10  7  2  0  0  0  0
 11  5  1  0  0  0  0
 11  9  1  0  0  0  0
 12  6  1  0  0  0  0
 13 10  1  0  0  0  0
 13 12  2  0  0  0  0
 14 11  2  0  0  0  0
 14 13  1  0  0  0  0
 15  8  1  0  0  0  0
 15 14  1  0  0  0  0
 16 15  2  0  0  0  0
 17  7  1  0  0  0  0
 17 12  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0033878

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1CCC2=C(C3=C(OC=C3C)C=C2C)C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C15H16O2/c1-8-4-5-11-9(2)6-12-13(10(3)7-17-12)14(11)15(8)16/h6-8H,4-5H2,1-3H3

> <INCHI_KEY>
YBJIFGYQRRWWFW-UHFFFAOYSA-N

> <FORMULA>
C15H16O2

> <MOLECULAR_WEIGHT>
228.2863

> <EXACT_MASS>
228.115029756

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
25.86135639083648

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1,5,8-trimethyl-6H,7H,8H,9H-naphtho[2,1-b]furan-9-one

> <ALOGPS_LOGP>
3.81

> <JCHEM_LOGP>
4.010077126

> <ALOGPS_LOGS>
-3.96

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
16.82229960371077

> <JCHEM_PKA_STRONGEST_BASIC>
-2.781147526644492

> <JCHEM_POLAR_SURFACE_AREA>
30.21

> <JCHEM_REFRACTIVITY>
67.82469999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.53e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1,5,8-trimethyl-6H,7H,8H-naphtho[2,1-b]furan-9-one

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0033878
     RDKit          3D
(S)-Curzeone
 33 35  0  0  0  0  0  0  0  0999 V2000
    3.5688    0.3699    0.8076 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2029    0.7746    0.4375 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7756    2.1020    0.5457 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4870    2.4484    0.1919 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1856    3.5586    0.1837 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4031    3.3900   -0.2373 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5967    2.0370   -0.5515 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8772    1.4688   -1.0065 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3908    1.4471   -0.2804 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0395    0.1564   -0.3843 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3507   -0.1842   -0.0191 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6417   -1.6319   -0.1720 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5054   -2.3501    0.5344 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7497   -2.2235   -0.2620 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0038   -2.3954    0.5696 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8075   -0.9059   -0.9425 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4972   -0.6265   -1.9342 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1630    0.0068   -0.0724 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0996    1.2676    1.1900 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5840   -0.3719    1.6421 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4405    2.8738    0.9049 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1937    4.1219   -0.3538 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0165    1.4455   -2.0882 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7225    2.1949   -0.6601 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2030    0.5512   -0.4642 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5948   -1.9217   -1.2435 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6272   -1.9166    0.2037 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7456   -3.4438    0.6756 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3873   -1.9626    1.5789 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7352   -2.9954   -1.0561 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2738   -1.4044    0.9706 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7992   -2.7760   -0.0931 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7582   -3.1048    1.3849 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  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  1  0
 16 17  2  0
 11  2  1  0
  9  4  2  0
 16 10  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  3 21  1  0
  6 22  1  0
  8 23  1  0
  8 24  1  0
  8 25  1  0
 12 26  1  0
 12 27  1  0
 13 28  1  0
 13 29  1  0
 14 30  1  0
 15 31  1  0
 15 32  1  0
 15 33  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       2.379  -1.848   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.896   4.745   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.707  -1.998   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.462   0.818   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.273   2.127   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.163   3.340   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.499   0.080   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.190  -0.539   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.624   3.388   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.074  -0.502   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.812   2.079   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.891   1.983   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.080   0.674   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.540   0.722   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.729  -0.587   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       5.457  -1.944   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       9.386   1.616   0.000  0.00  0.00           O+0
CONECT    1    8                                                            
CONECT    2    9                                                            
CONECT    3   10                                                            
CONECT    4    5    8                                                       
CONECT    5    4   11                                                       
CONECT    6    9   12                                                       
CONECT    7   10   17                                                       
CONECT    8    1    4   15                                                  
CONECT    9    2    6   11                                                  
CONECT   10    3    7   13                                                  
CONECT   11    5    9   14                                                  
CONECT   12    6   13   17                                                  
CONECT   13   10   12   14                                                  
CONECT   14   11   13   15                                                  
CONECT   15    8   14   16                                                  
CONECT   16   15                                                            
CONECT   17    7   12                                                       
MASTER        0    0    0    0    0    0    0    0   17    0   38    0
END

COMPND    HMDB0033878
HETATM    1  C1  UNL     1       3.569   0.370   0.808  1.00  0.00           C  
HETATM    2  C2  UNL     1       2.203   0.775   0.438  1.00  0.00           C  
HETATM    3  C3  UNL     1       1.776   2.102   0.546  1.00  0.00           C  
HETATM    4  C4  UNL     1       0.487   2.448   0.192  1.00  0.00           C  
HETATM    5  O1  UNL     1      -0.186   3.559   0.184  1.00  0.00           O  
HETATM    6  C5  UNL     1      -1.403   3.390  -0.237  1.00  0.00           C  
HETATM    7  C6  UNL     1      -1.597   2.037  -0.552  1.00  0.00           C  
HETATM    8  C7  UNL     1      -2.877   1.469  -1.006  1.00  0.00           C  
HETATM    9  C8  UNL     1      -0.391   1.447  -0.280  1.00  0.00           C  
HETATM   10  C9  UNL     1       0.039   0.156  -0.384  1.00  0.00           C  
HETATM   11  C10 UNL     1       1.351  -0.184  -0.019  1.00  0.00           C  
HETATM   12  C11 UNL     1       1.642  -1.632  -0.172  1.00  0.00           C  
HETATM   13  C12 UNL     1       0.505  -2.350   0.534  1.00  0.00           C  
HETATM   14  C13 UNL     1      -0.750  -2.223  -0.262  1.00  0.00           C  
HETATM   15  C14 UNL     1      -2.004  -2.395   0.570  1.00  0.00           C  
HETATM   16  C15 UNL     1      -0.807  -0.906  -0.942  1.00  0.00           C  
HETATM   17  O2  UNL     1      -1.497  -0.627  -1.934  1.00  0.00           O  
HETATM   18  H1  UNL     1       4.163   0.007  -0.072  1.00  0.00           H  
HETATM   19  H2  UNL     1       4.100   1.268   1.190  1.00  0.00           H  
HETATM   20  H3  UNL     1       3.584  -0.372   1.642  1.00  0.00           H  
HETATM   21  H4  UNL     1       2.441   2.874   0.905  1.00  0.00           H  
HETATM   22  H5  UNL     1      -2.194   4.122  -0.354  1.00  0.00           H  
HETATM   23  H6  UNL     1      -3.017   1.445  -2.088  1.00  0.00           H  
HETATM   24  H7  UNL     1      -3.722   2.195  -0.660  1.00  0.00           H  
HETATM   25  H8  UNL     1      -3.203   0.551  -0.464  1.00  0.00           H  
HETATM   26  H9  UNL     1       1.595  -1.922  -1.244  1.00  0.00           H  
HETATM   27  H10 UNL     1       2.627  -1.917   0.204  1.00  0.00           H  
HETATM   28  H11 UNL     1       0.746  -3.444   0.676  1.00  0.00           H  
HETATM   29  H12 UNL     1       0.387  -1.963   1.579  1.00  0.00           H  
HETATM   30  H13 UNL     1      -0.735  -2.995  -1.056  1.00  0.00           H  
HETATM   31  H14 UNL     1      -2.274  -1.404   0.971  1.00  0.00           H  
HETATM   32  H15 UNL     1      -2.799  -2.776  -0.093  1.00  0.00           H  
HETATM   33  H16 UNL     1      -1.758  -3.105   1.385  1.00  0.00           H  
CONECT    1    2   18   19   20
CONECT    2    3    3   11
CONECT    3    4   21
CONECT    4    5    9    9
CONECT    5    6
CONECT    6    7    7   22
CONECT    7    8    9
CONECT    8   23   24   25
CONECT    9   10
CONECT   10   11   11   16
CONECT   11   12
CONECT   12   13   26   27
CONECT   13   14   28   29
CONECT   14   15   16   30
CONECT   15   31   32   33
CONECT   16   17   17
END

HMDB0033878
     RDKit          3D
(S)-Curzeone
 33 35  0  0  0  0  0  0  0  0999 V2000
    3.5688    0.3699    0.8076 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2029    0.7746    0.4375 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7756    2.1020    0.5457 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4870    2.4484    0.1919 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1856    3.5586    0.1837 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4031    3.3900   -0.2373 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5967    2.0370   -0.5515 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8772    1.4688   -1.0065 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3908    1.4471   -0.2804 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0395    0.1564   -0.3843 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3507   -0.1842   -0.0191 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6417   -1.6319   -0.1720 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5054   -2.3501    0.5344 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7497   -2.2235   -0.2620 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0038   -2.3954    0.5696 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8075   -0.9059   -0.9425 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4972   -0.6265   -1.9342 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1630    0.0068   -0.0724 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0996    1.2676    1.1900 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5840   -0.3719    1.6421 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4405    2.8738    0.9049 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1937    4.1219   -0.3538 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0165    1.4455   -2.0882 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7225    2.1949   -0.6601 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2030    0.5512   -0.4642 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5948   -1.9217   -1.2435 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6272   -1.9166    0.2037 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7456   -3.4438    0.6756 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3873   -1.9626    1.5789 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7352   -2.9954   -1.0561 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2738   -1.4044    0.9706 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7992   -2.7760   -0.0931 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7582   -3.1048    1.3849 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  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  1  0
 16 17  2  0
 11  2  1  0
  9  4  2  0
 16 10  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  3 21  1  0
  6 22  1  0
  8 23  1  0
  8 24  1  0
  8 25  1  0
 12 26  1  0
 12 27  1  0
 13 28  1  0
 13 29  1  0
 14 30  1  0
 15 31  1  0
 15 32  1  0
 15 33  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₁₅H₁₆O₂

Average Molecular Weight

228.2863

Monoisotopic Molecular Weight

228.115029756

IUPAC Name

1,5,8-trimethyl-6H,7H,8H,9H-naphtho[2,1-b]furan-9-one

Traditional Name

1,5,8-trimethyl-6H,7H,8H-naphtho[2,1-b]furan-9-one

CAS Registry Number

Not Available

SMILES

CC1CCC2=C(C3=C(OC=C3C)C=C2C)C1=O

InChI Identifier

InChI=1S/C15H16O2/c1-8-4-5-11-9(2)6-12-13(10(3)7-17-12)14(11)15(8)16/h6-8H,4-5H2,1-3H3

InChI Key

YBJIFGYQRRWWFW-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Sesquiterpenoids

Alternative Parents

Substituents

Cadinane sesquiterpenoid
Sesquiterpenoid
Naphthofuran
Tetralin
Benzofuran
Aryl ketone
Aryl alkyl ketone
Benzenoid
Heteroaromatic compound
Furan
Ketone
Oxacycle
Organoheterocyclic compound
Hydrocarbon derivative
Organooxygen compound
Organic oxide
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0033878)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0033878)

Source

Endogenous

Endogenous (HMDB: HMDB0033878)

Animal

Animal (HMDB: HMDB0033878)

Exogenous

Food

Food (HMDB: HMDB0033878)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid peroxidation (HMDB: HMDB0033878)

Biochemical process

Fatty acid metabolism (HMDB: HMDB0033878)

Cellular process

Cell signaling (HMDB: HMDB0033878)

Biochemical pathway

Lipid metabolism pathway (HMDB: HMDB0033878)

Role

Biological role

Membrane stabilizer (HMDB: HMDB0033878)

Nutrient

Nutrient (HMDB: HMDB0033878)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	72 - 74 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.025 g/L	ALOGPS
logP	3.81	ALOGPS
logP	4.01	ChemAxon
logS	-4	ALOGPS
pKa (Strongest Acidic)	16.82	ChemAxon
pKa (Strongest Basic)	-2.8	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	0	ChemAxon
Refractivity	67.82 m³·mol⁻¹	ChemAxon
Polarizability	25.86 Å³	ChemAxon
Number of Rings	3	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]+	154.185	31661259
DarkChem	[M-H]-	153.986	31661259
DeepCCS	[M+H]+	158.705	30932474
DeepCCS	[M-H]-	156.347	30932474
DeepCCS	[M-2H]-	189.265	30932474
DeepCCS	[M+Na]+	164.799	30932474
AllCCS	[M+H]+	149.7	32859911
AllCCS	[M+H-H2O]+	145.7	32859911
AllCCS	[M+NH4]+	153.4	32859911
AllCCS	[M+Na]+	154.5	32859911
AllCCS	[M-H]-	157.5	32859911
AllCCS	[M+Na-2H]-	157.1	32859911
AllCCS	[M+HCOO]-	156.8	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
(S)-Curzeone	CC1CCC2=C(C3=C(OC=C3C)C=C2C)C1=O	2849.6	Standard polar	33892256
(S)-Curzeone	CC1CCC2=C(C3=C(OC=C3C)C=C2C)C1=O	2017.8	Standard non polar	33892256
(S)-Curzeone	CC1CCC2=C(C3=C(OC=C3C)C=C2C)C1=O	2022.0	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 - (S)-Curzeone GC-MS (Non-derivatized) - 70eV, Positive	splash10-114s-0940000000-aed5c27f4d299a4a9c63	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (S)-Curzeone GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (S)-Curzeone 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 - (S)-Curzeone 10V, Positive-QTOF	splash10-004i-0090000000-a51b0f24d58e660aded2	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (S)-Curzeone 20V, Positive-QTOF	splash10-05di-3970000000-05936871a3b553d3b9ac	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (S)-Curzeone 40V, Positive-QTOF	splash10-0596-4910000000-a85a82af6c087b1e5fd0	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (S)-Curzeone 10V, Negative-QTOF	splash10-004i-0090000000-74e940b951f2ff31af31	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (S)-Curzeone 20V, Negative-QTOF	splash10-004i-0090000000-2284b13fc1b40598cbd8	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (S)-Curzeone 40V, Negative-QTOF	splash10-06s2-3920000000-4188ce547ce82386517b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (S)-Curzeone 10V, Positive-QTOF	splash10-004i-0090000000-f29187c8de7487e22fe6	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (S)-Curzeone 20V, Positive-QTOF	splash10-004i-0190000000-958cdfbfcd649cc43fcd	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (S)-Curzeone 40V, Positive-QTOF	splash10-052b-0910000000-f554ca7e64e96cf85cc9	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (S)-Curzeone 10V, Negative-QTOF	splash10-004i-0090000000-90bbee923915d81ba797	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (S)-Curzeone 20V, Negative-QTOF	splash10-004i-0090000000-c7b0b6b1cec6889533ce	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (S)-Curzeone 40V, Negative-QTOF	splash10-004i-0590000000-a74b48ae07961131bd43	2021-09-25	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

FDB012071

KNApSAcK ID

Not Available

Chemspider ID

35013669

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

131751498

PDB ID

Not Available

ChEBI ID

174174

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

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 (S)-Curzeone (HMDB0033878)

MOL for HMDB0033878 ((S)-Curzeone)

3D MOL for HMDB0033878 ((S)-Curzeone)

3D SDF for HMDB0033878 ((S)-Curzeone)

3D-SDF for HMDB0033878 ((S)-Curzeone)

PDB for HMDB0033878 ((S)-Curzeone)

3D PDB for HMDB0033878 ((S)-Curzeone)

SMILES for HMDB0033878 ((S)-Curzeone)

INCHI for HMDB0033878 ((S)-Curzeone)

Structure for HMDB0033878 ((S)-Curzeone)

3D Structure for HMDB0033878 ((S)-Curzeone)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra