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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 19:37:02 UTC

Update Date

2022-03-07 02:54:13 UTC

HMDB ID

HMDB0034714

Secondary Accession Numbers

HMDB34714

Metabolite Identification

Common Name

Curdione

Description

Curdione belongs to the class of organic compounds known as germacrane sesquiterpenoids. These are sesquiterpenoids having the germacrane skeleton, with a structure characterized by a cyclodecane ring substituted with an isopropyl and two methyl groups. Based on a literature review a significant number of articles have been published on Curdione.

Structure

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

HMDB0034714
     RDKit          3D
Curdione
 41 41  0  0  0  0  0  0  0  0999 V2000
   -1.9952    3.6310   -0.2060 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6585    2.1171   -0.1240 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5187    1.3540    0.5035 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3953   -0.0454    0.6896 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2114   -1.0613   -0.3605 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4171   -2.3216    0.0883 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7884   -3.4835   -0.7607 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0862   -2.0566   -0.0373 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7681   -2.9252   -0.4776 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4917   -0.7655    0.4016 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5377    0.1417   -0.1475 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8060    0.1795    0.6278 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7650    1.1344   -0.0429 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4153   -1.1827    0.6456 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8182    1.4934   -0.0337 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3137    2.3433    0.6144 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4740    1.6798   -0.7435 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6359    4.0843    0.7383 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0837    3.7445   -0.3321 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5065    4.0574   -1.0911 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4129    1.9319    0.9072 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8305   -0.3500    1.6502 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4273   -0.3426    1.1420 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2109   -1.5666   -0.6326 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8997   -0.7555   -1.3590 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5995   -2.4381    1.1672 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2454   -3.2059   -1.7316 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8948   -4.0930   -0.9905 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4675   -4.1470   -0.1648 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4568   -0.5731    1.4868 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3240   -0.2293   -0.1881 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7163    0.0120   -1.2232 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6200    0.5167    1.6675 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3447    1.6592    0.7711 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4618    0.5476   -0.6835 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2036    1.8520   -0.6705 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5139   -1.0688    0.7809 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2864   -1.7207   -0.3308 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0535   -1.7972    1.4987 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1152    2.6043   -1.3783 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5465    1.0454   -1.6709 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  1  0
  6  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  1  0
 11 15  1  0
 15 16  2  0
 15 17  1  0
 17  2  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  3 21  1  0
  4 22  1  0
  4 23  1  0
  5 24  1  0
  5 25  1  0
  6 26  1  0
  7 27  1  0
  7 28  1  0
  7 29  1  0
 10 30  1  0
 10 31  1  0
 11 32  1  0
 12 33  1  0
 13 34  1  0
 13 35  1  0
 13 36  1  0
 14 37  1  0
 14 38  1  0
 14 39  1  0
 17 40  1  0
 17 41  1  0
M  END


  Mrv0541 05061308022D          

 17 17  0  0  0  0            999 V2000
   -0.3545    0.6413    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0418   -0.7316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6271    2.7006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8161   -1.4180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8253    0.5269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0234    1.3278    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4197   -0.0451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6363    1.6710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8345   -0.5028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2400    0.0693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    1.8998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2216   -0.8460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0326    0.2981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.0748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4381    0.8701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2308   -1.8756    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3376    1.1509    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  6  5  1  0  0  0  0
  7  5  1  0  0  0  0
 10  1  1  0  0  0  0
 10  2  1  0  0  0  0
 11  3  1  0  0  0  0
 11  6  2  0  0  0  0
 11  8  1  0  0  0  0
 12  4  1  0  0  0  0
 12  7  1  0  0  0  0
 13  9  1  0  0  0  0
 13 10  1  0  0  0  0
 14  9  1  0  0  0  0
 14 12  1  0  0  0  0
 15  8  1  0  0  0  0
 15 13  1  0  0  0  0
 16 14  2  0  0  0  0
 17 15  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0034714

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(C)C1CC(=O)C(C)CC\C=C(C)/CC1=O

> <INCHI_IDENTIFIER>
InChI=1S/C15H24O2/c1-10(2)13-9-14(16)12(4)7-5-6-11(3)8-15(13)17/h6,10,12-13H,5,7-9H2,1-4H3/b11-6-

> <INCHI_KEY>
KDPFMRXIVDLQKX-WDZFZDKYSA-N

> <FORMULA>
C15H24O2

> <MOLECULAR_WEIGHT>
236.3499

> <EXACT_MASS>
236.177630012

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
27.615136747685433

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(6Z)-6,10-dimethyl-3-(propan-2-yl)cyclodec-6-ene-1,4-dione

> <ALOGPS_LOGP>
3.25

> <JCHEM_LOGP>
3.786251132333333

> <ALOGPS_LOGS>
-3.09

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
16.650149575724075

> <JCHEM_PKA_STRONGEST_BASIC>
-7.1594889857379655

> <JCHEM_POLAR_SURFACE_AREA>
34.14

> <JCHEM_REFRACTIVITY>
70.98999999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.90e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(6Z)-3-isopropyl-6,10-dimethylcyclodec-6-ene-1,4-dione

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0034714
     RDKit          3D
Curdione
 41 41  0  0  0  0  0  0  0  0999 V2000
   -1.9952    3.6310   -0.2060 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6585    2.1171   -0.1240 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5187    1.3540    0.5035 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3953   -0.0454    0.6896 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2114   -1.0613   -0.3605 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4171   -2.3216    0.0883 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7884   -3.4835   -0.7607 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0862   -2.0566   -0.0373 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7681   -2.9252   -0.4776 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4917   -0.7655    0.4016 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5377    0.1417   -0.1475 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8060    0.1795    0.6278 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7650    1.1344   -0.0429 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4153   -1.1827    0.6456 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8182    1.4934   -0.0337 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3137    2.3433    0.6144 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4740    1.6798   -0.7435 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6359    4.0843    0.7383 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0837    3.7445   -0.3321 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5065    4.0574   -1.0911 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4129    1.9319    0.9072 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8305   -0.3500    1.6502 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4273   -0.3426    1.1420 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2109   -1.5666   -0.6326 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8997   -0.7555   -1.3590 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5995   -2.4381    1.1672 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2454   -3.2059   -1.7316 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8948   -4.0930   -0.9905 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4675   -4.1470   -0.1648 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4568   -0.5731    1.4868 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3240   -0.2293   -0.1881 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7163    0.0120   -1.2232 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6200    0.5167    1.6675 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3447    1.6592    0.7711 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4618    0.5476   -0.6835 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2036    1.8520   -0.6705 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5139   -1.0688    0.7809 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2864   -1.7207   -0.3308 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0535   -1.7972    1.4987 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1152    2.6043   -1.3783 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5465    1.0454   -1.6709 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  1  0
  6  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  1  0
 11 15  1  0
 15 16  2  0
 15 17  1  0
 17  2  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  3 21  1  0
  4 22  1  0
  4 23  1  0
  5 24  1  0
  5 25  1  0
  6 26  1  0
  7 27  1  0
  7 28  1  0
  7 29  1  0
 10 30  1  0
 10 31  1  0
 11 32  1  0
 12 33  1  0
 13 34  1  0
 13 35  1  0
 13 36  1  0
 14 37  1  0
 14 38  1  0
 14 39  1  0
 17 40  1  0
 17 41  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      -0.662   1.197   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.078  -1.366   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.037   5.041   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.257  -2.647   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.407   0.984   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.777   2.479   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.517  -0.084   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.188   3.119   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.558  -0.939   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.448   0.129   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.667   3.546   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.147  -1.579   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.928   0.556   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.667  -2.006   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.818   1.624   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       2.297  -3.501   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0      -0.630   2.148   0.000  0.00  0.00           O+0
CONECT    1   10                                                            
CONECT    2   10                                                            
CONECT    3   11                                                            
CONECT    4   12                                                            
CONECT    5    6    7                                                       
CONECT    6    5   11                                                       
CONECT    7    5   12                                                       
CONECT    8   11   15                                                       
CONECT    9   13   14                                                       
CONECT   10    1    2   13                                                  
CONECT   11    3    6    8                                                  
CONECT   12    4    7   14                                                  
CONECT   13    9   10   15                                                  
CONECT   14    9   12   16                                                  
CONECT   15    8   13   17                                                  
CONECT   16   14                                                            
CONECT   17   15                                                            
MASTER        0    0    0    0    0    0    0    0   17    0   34    0
END

COMPND    HMDB0034714
HETATM    1  C1  UNL     1      -1.995   3.631  -0.206  1.00  0.00           C  
HETATM    2  C2  UNL     1      -1.659   2.117  -0.124  1.00  0.00           C  
HETATM    3  C3  UNL     1      -2.519   1.354   0.504  1.00  0.00           C  
HETATM    4  C4  UNL     1      -2.395  -0.045   0.690  1.00  0.00           C  
HETATM    5  C5  UNL     1      -2.211  -1.061  -0.361  1.00  0.00           C  
HETATM    6  C6  UNL     1      -1.417  -2.322   0.088  1.00  0.00           C  
HETATM    7  C7  UNL     1      -1.788  -3.483  -0.761  1.00  0.00           C  
HETATM    8  C8  UNL     1       0.086  -2.057  -0.037  1.00  0.00           C  
HETATM    9  O1  UNL     1       0.768  -2.925  -0.478  1.00  0.00           O  
HETATM   10  C9  UNL     1       0.492  -0.765   0.402  1.00  0.00           C  
HETATM   11  C10 UNL     1       1.538   0.142  -0.147  1.00  0.00           C  
HETATM   12  C11 UNL     1       2.806   0.180   0.628  1.00  0.00           C  
HETATM   13  C12 UNL     1       3.765   1.134  -0.043  1.00  0.00           C  
HETATM   14  C13 UNL     1       3.415  -1.183   0.646  1.00  0.00           C  
HETATM   15  C14 UNL     1       0.818   1.493  -0.034  1.00  0.00           C  
HETATM   16  O2  UNL     1       1.314   2.343   0.614  1.00  0.00           O  
HETATM   17  C15 UNL     1      -0.474   1.680  -0.744  1.00  0.00           C  
HETATM   18  H1  UNL     1      -1.636   4.084   0.738  1.00  0.00           H  
HETATM   19  H2  UNL     1      -3.084   3.744  -0.332  1.00  0.00           H  
HETATM   20  H3  UNL     1      -1.506   4.057  -1.091  1.00  0.00           H  
HETATM   21  H4  UNL     1      -3.413   1.932   0.907  1.00  0.00           H  
HETATM   22  H5  UNL     1      -1.831  -0.350   1.650  1.00  0.00           H  
HETATM   23  H6  UNL     1      -3.427  -0.343   1.142  1.00  0.00           H  
HETATM   24  H7  UNL     1      -3.211  -1.567  -0.633  1.00  0.00           H  
HETATM   25  H8  UNL     1      -1.900  -0.756  -1.359  1.00  0.00           H  
HETATM   26  H9  UNL     1      -1.600  -2.438   1.167  1.00  0.00           H  
HETATM   27  H10 UNL     1      -2.245  -3.206  -1.732  1.00  0.00           H  
HETATM   28  H11 UNL     1      -0.895  -4.093  -0.991  1.00  0.00           H  
HETATM   29  H12 UNL     1      -2.467  -4.147  -0.165  1.00  0.00           H  
HETATM   30  H13 UNL     1       0.457  -0.573   1.487  1.00  0.00           H  
HETATM   31  H14 UNL     1      -0.324  -0.229  -0.188  1.00  0.00           H  
HETATM   32  H15 UNL     1       1.716   0.012  -1.223  1.00  0.00           H  
HETATM   33  H16 UNL     1       2.620   0.517   1.668  1.00  0.00           H  
HETATM   34  H17 UNL     1       4.345   1.659   0.771  1.00  0.00           H  
HETATM   35  H18 UNL     1       4.462   0.548  -0.683  1.00  0.00           H  
HETATM   36  H19 UNL     1       3.204   1.852  -0.671  1.00  0.00           H  
HETATM   37  H20 UNL     1       4.514  -1.069   0.781  1.00  0.00           H  
HETATM   38  H21 UNL     1       3.286  -1.721  -0.331  1.00  0.00           H  
HETATM   39  H22 UNL     1       3.054  -1.797   1.499  1.00  0.00           H  
HETATM   40  H23 UNL     1      -0.115   2.604  -1.378  1.00  0.00           H  
HETATM   41  H24 UNL     1      -0.547   1.045  -1.671  1.00  0.00           H  
CONECT    1    2   18   19   20
CONECT    2    3    3   17
CONECT    3    4   21
CONECT    4    5   22   23
CONECT    5    6   24   25
CONECT    6    7    8   26
CONECT    7   27   28   29
CONECT    8    9    9   10
CONECT   10   11   30   31
CONECT   11   12   15   32
CONECT   12   13   14   33
CONECT   13   34   35   36
CONECT   14   37   38   39
CONECT   15   16   16   17
CONECT   17   40   41
END

HMDB0034714
     RDKit          3D
Curdione
 41 41  0  0  0  0  0  0  0  0999 V2000
   -1.9952    3.6310   -0.2060 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6585    2.1171   -0.1240 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5187    1.3540    0.5035 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3953   -0.0454    0.6896 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2114   -1.0613   -0.3605 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4171   -2.3216    0.0883 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7884   -3.4835   -0.7607 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0862   -2.0566   -0.0373 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7681   -2.9252   -0.4776 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4917   -0.7655    0.4016 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5377    0.1417   -0.1475 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8060    0.1795    0.6278 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7650    1.1344   -0.0429 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4153   -1.1827    0.6456 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8182    1.4934   -0.0337 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3137    2.3433    0.6144 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4740    1.6798   -0.7435 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6359    4.0843    0.7383 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0837    3.7445   -0.3321 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5065    4.0574   -1.0911 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4129    1.9319    0.9072 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8305   -0.3500    1.6502 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4273   -0.3426    1.1420 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2109   -1.5666   -0.6326 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8997   -0.7555   -1.3590 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5995   -2.4381    1.1672 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2454   -3.2059   -1.7316 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8948   -4.0930   -0.9905 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4675   -4.1470   -0.1648 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4568   -0.5731    1.4868 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3240   -0.2293   -0.1881 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7163    0.0120   -1.2232 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6200    0.5167    1.6675 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3447    1.6592    0.7711 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4618    0.5476   -0.6835 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2036    1.8520   -0.6705 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5139   -1.0688    0.7809 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2864   -1.7207   -0.3308 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0535   -1.7972    1.4987 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1152    2.6043   -1.3783 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5465    1.0454   -1.6709 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  1  0
  6  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  1  0
 11 15  1  0
 15 16  2  0
 15 17  1  0
 17  2  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  3 21  1  0
  4 22  1  0
  4 23  1  0
  5 24  1  0
  5 25  1  0
  6 26  1  0
  7 27  1  0
  7 28  1  0
  7 29  1  0
 10 30  1  0
 10 31  1  0
 11 32  1  0
 12 33  1  0
 13 34  1  0
 13 35  1  0
 13 36  1  0
 14 37  1  0
 14 38  1  0
 14 39  1  0
 17 40  1  0
 17 41  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(+)-Curdione	HMDB
(+)-Germacr-1(10)-ene-5,8-dione	HMDB
Germacr-1(10)-ene-5,8-dione	HMDB
Curdione	MeSH

Chemical Formula

C₁₅H₂₄O₂

Average Molecular Weight

236.3499

Monoisotopic Molecular Weight

236.177630012

IUPAC Name

(6Z)-6,10-dimethyl-3-(propan-2-yl)cyclodec-6-ene-1,4-dione

Traditional Name

(6Z)-3-isopropyl-6,10-dimethylcyclodec-6-ene-1,4-dione

CAS Registry Number

13657-68-6

SMILES

CC(C)C1CC(=O)C(C)CC\C=C(C)/CC1=O

InChI Identifier

InChI=1S/C15H24O2/c1-10(2)13-9-14(16)12(4)7-5-6-11(3)8-15(13)17/h6,10,12-13H,5,7-9H2,1-4H3/b11-6-

InChI Key

KDPFMRXIVDLQKX-WDZFZDKYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as germacrane sesquiterpenoids. These are sesquiterpenoids having the germacrane skeleton, with a structure characterized by a cyclodecane ring substituted with an isopropyl and two methyl groups.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Germacrane sesquiterpenoids

Alternative Parents

Substituents

Germacrane sesquiterpenoid
Cyclic ketone
Ketone
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cytoplasm (HMDB: HMDB0034714)
Cell membrane (HMDB: HMDB0034714)

Cellular substructure

Extracellular (HMDB: HMDB0034714)
Membrane (HMDB: HMDB0034714)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0034714)

Source

Endogenous

Endogenous (HMDB: HMDB0034714)

Plant

Plant (HMDB: HMDB0034714)

Animal

Animal (HMDB: HMDB0034714)

Exogenous

Food

Food (HMDB: HMDB0034714)

Herb and spice

Spice

Turmeric (FooDB: FOOD00068)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid peroxidation (HMDB: HMDB0034714)

Biochemical process

Fatty acid metabolism (HMDB: HMDB0034714)

Cellular process

Cell signaling (HMDB: HMDB0034714)

Biochemical pathway

Lipid metabolism pathway (HMDB: HMDB0034714)

Role

Biological role

Nutrient

Nutrient (HMDB: HMDB0034714)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0034714)

Emulsifier (HMDB: HMDB0034714)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	61 - 62 °C	Not Available
Boiling Point	347.60 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	61.25 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	3.120 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.19 g/L	ALOGPS
logP	3.25	ALOGPS
logP	3.79	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Acidic)	16.65	ChemAxon
pKa (Strongest Basic)	-7.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	34.14 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	70.99 m³·mol⁻¹	ChemAxon
Polarizability	27.62 Å³	ChemAxon
Number of Rings	1	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]+	158.381	31661259
DarkChem	[M-H]-	152.758	31661259
DeepCCS	[M+H]+	160.203	30932474
DeepCCS	[M-H]-	157.845	30932474
DeepCCS	[M-2H]-	191.451	30932474
DeepCCS	[M+Na]+	166.6	30932474
AllCCS	[M+H]+	155.5	32859911
AllCCS	[M+H-H2O]+	151.7	32859911
AllCCS	[M+NH4]+	159.0	32859911
AllCCS	[M+Na]+	160.0	32859911
AllCCS	[M-H]-	162.6	32859911
AllCCS	[M+Na-2H]-	163.3	32859911
AllCCS	[M+HCOO]-	164.2	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Curdione	CC(C)C1CC(=O)C(C)CC\C=C(C)/CC1=O	2280.1	Standard polar	33892256
Curdione	CC(C)C1CC(=O)C(C)CC\C=C(C)/CC1=O	1694.8	Standard non polar	33892256
Curdione	CC(C)C1CC(=O)C(C)CC\C=C(C)/CC1=O	1729.2	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Curdione,1TMS,isomer #1	CC1=C(O[Si](C)(C)C)CC(C(C)C)C(=O)C/C(C)=C\CC1	1917.1	Semi standard non polar	33892256
Curdione,1TMS,isomer #1	CC1=C(O[Si](C)(C)C)CC(C(C)C)C(=O)C/C(C)=C\CC1	1904.7	Standard non polar	33892256
Curdione,1TMS,isomer #2	C/C1=C/CCC(C)C(=O)CC(C(C)C)=C(O[Si](C)(C)C)C1	1914.3	Semi standard non polar	33892256
Curdione,1TMS,isomer #2	C/C1=C/CCC(C)C(=O)CC(C(C)C)=C(O[Si](C)(C)C)C1	1902.7	Standard non polar	33892256
Curdione,1TMS,isomer #3	C/C1=C/CCC(C)C(O[Si](C)(C)C)=CC(C(C)C)C(=O)C1	1893.7	Semi standard non polar	33892256
Curdione,1TMS,isomer #3	C/C1=C/CCC(C)C(O[Si](C)(C)C)=CC(C(C)C)C(=O)C1	1886.2	Standard non polar	33892256
Curdione,1TMS,isomer #4	C/C1=C/CCC(C)C(=O)CC(C(C)C)C(O[Si](C)(C)C)=C1	1970.5	Semi standard non polar	33892256
Curdione,1TMS,isomer #4	C/C1=C/CCC(C)C(=O)CC(C(C)C)C(O[Si](C)(C)C)=C1	1930.3	Standard non polar	33892256
Curdione,2TMS,isomer #1	CC1=C(O[Si](C)(C)C)CC(C(C)C)=C(O[Si](C)(C)C)C/C(C)=C\CC1	2004.9	Semi standard non polar	33892256
Curdione,2TMS,isomer #1	CC1=C(O[Si](C)(C)C)CC(C(C)C)=C(O[Si](C)(C)C)C/C(C)=C\CC1	2130.7	Standard non polar	33892256
Curdione,2TMS,isomer #2	CC1=C(O[Si](C)(C)C)CC(C(C)C)C(O[Si](C)(C)C)=C/C(C)=C\CC1	2066.8	Semi standard non polar	33892256
Curdione,2TMS,isomer #2	CC1=C(O[Si](C)(C)C)CC(C(C)C)C(O[Si](C)(C)C)=C/C(C)=C\CC1	2112.7	Standard non polar	33892256
Curdione,2TMS,isomer #3	C/C1=C/CCC(C)C(O[Si](C)(C)C)=CC(C(C)C)=C(O[Si](C)(C)C)C1	1951.8	Semi standard non polar	33892256
Curdione,2TMS,isomer #3	C/C1=C/CCC(C)C(O[Si](C)(C)C)=CC(C(C)C)=C(O[Si](C)(C)C)C1	2013.8	Standard non polar	33892256
Curdione,2TMS,isomer #4	C/C1=C/CCC(C)C(O[Si](C)(C)C)=CC(C(C)C)C(O[Si](C)(C)C)=C1	2001.3	Semi standard non polar	33892256
Curdione,2TMS,isomer #4	C/C1=C/CCC(C)C(O[Si](C)(C)C)=CC(C(C)C)C(O[Si](C)(C)C)=C1	2035.3	Standard non polar	33892256
Curdione,1TBDMS,isomer #1	CC1=C(O[Si](C)(C)C(C)(C)C)CC(C(C)C)C(=O)C/C(C)=C\CC1	2136.6	Semi standard non polar	33892256
Curdione,1TBDMS,isomer #1	CC1=C(O[Si](C)(C)C(C)(C)C)CC(C(C)C)C(=O)C/C(C)=C\CC1	2110.3	Standard non polar	33892256
Curdione,1TBDMS,isomer #2	C/C1=C/CCC(C)C(=O)CC(C(C)C)=C(O[Si](C)(C)C(C)(C)C)C1	2140.4	Semi standard non polar	33892256
Curdione,1TBDMS,isomer #2	C/C1=C/CCC(C)C(=O)CC(C(C)C)=C(O[Si](C)(C)C(C)(C)C)C1	2106.0	Standard non polar	33892256
Curdione,1TBDMS,isomer #3	C/C1=C/CCC(C)C(O[Si](C)(C)C(C)(C)C)=CC(C(C)C)C(=O)C1	2109.8	Semi standard non polar	33892256
Curdione,1TBDMS,isomer #3	C/C1=C/CCC(C)C(O[Si](C)(C)C(C)(C)C)=CC(C(C)C)C(=O)C1	2056.3	Standard non polar	33892256
Curdione,1TBDMS,isomer #4	C/C1=C/CCC(C)C(=O)CC(C(C)C)C(O[Si](C)(C)C(C)(C)C)=C1	2169.8	Semi standard non polar	33892256
Curdione,1TBDMS,isomer #4	C/C1=C/CCC(C)C(=O)CC(C(C)C)C(O[Si](C)(C)C(C)(C)C)=C1	2111.1	Standard non polar	33892256
Curdione,2TBDMS,isomer #1	CC1=C(O[Si](C)(C)C(C)(C)C)CC(C(C)C)=C(O[Si](C)(C)C(C)(C)C)C/C(C)=C\CC1	2452.3	Semi standard non polar	33892256
Curdione,2TBDMS,isomer #1	CC1=C(O[Si](C)(C)C(C)(C)C)CC(C(C)C)=C(O[Si](C)(C)C(C)(C)C)C/C(C)=C\CC1	2449.1	Standard non polar	33892256
Curdione,2TBDMS,isomer #2	CC1=C(O[Si](C)(C)C(C)(C)C)CC(C(C)C)C(O[Si](C)(C)C(C)(C)C)=C/C(C)=C\CC1	2489.4	Semi standard non polar	33892256
Curdione,2TBDMS,isomer #2	CC1=C(O[Si](C)(C)C(C)(C)C)CC(C(C)C)C(O[Si](C)(C)C(C)(C)C)=C/C(C)=C\CC1	2401.7	Standard non polar	33892256
Curdione,2TBDMS,isomer #3	C/C1=C/CCC(C)C(O[Si](C)(C)C(C)(C)C)=CC(C(C)C)=C(O[Si](C)(C)C(C)(C)C)C1	2397.0	Semi standard non polar	33892256
Curdione,2TBDMS,isomer #3	C/C1=C/CCC(C)C(O[Si](C)(C)C(C)(C)C)=CC(C(C)C)=C(O[Si](C)(C)C(C)(C)C)C1	2280.3	Standard non polar	33892256
Curdione,2TBDMS,isomer #4	C/C1=C/CCC(C)C(O[Si](C)(C)C(C)(C)C)=CC(C(C)C)C(O[Si](C)(C)C(C)(C)C)=C1	2426.3	Semi standard non polar	33892256
Curdione,2TBDMS,isomer #4	C/C1=C/CCC(C)C(O[Si](C)(C)C(C)(C)C)=CC(C(C)C)C(O[Si](C)(C)C(C)(C)C)=C1	2318.4	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Curdione GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-8490000000-7f0efd10a66464843191	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Curdione 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 - Curdione 10V, Positive-QTOF	splash10-000i-0290000000-7ca15e95e2b79ed79778	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Curdione 20V, Positive-QTOF	splash10-000j-8940000000-ee5080c5e15bcb7643eb	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Curdione 40V, Positive-QTOF	splash10-0aor-9200000000-c08dd6046f708e8c88cf	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Curdione 10V, Negative-QTOF	splash10-000i-0090000000-25fb99deae438bf84ae5	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Curdione 20V, Negative-QTOF	splash10-000i-0390000000-f8335d7dc177758d09c8	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Curdione 40V, Negative-QTOF	splash10-066u-9110000000-e2e9935192864fc90d36	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Curdione 10V, Negative-QTOF	splash10-000i-0090000000-c0031dc201eac6b6350a	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Curdione 20V, Negative-QTOF	splash10-000i-0090000000-ce35d6a35907d30e577f	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Curdione 40V, Negative-QTOF	splash10-004l-0910000000-17b31dd0bf560277454d	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Curdione 10V, Positive-QTOF	splash10-014i-0090000000-c25f9a0216e0fde29eb4	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Curdione 20V, Positive-QTOF	splash10-014i-0090000000-22b2b4d2dc96405a097d	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Curdione 40V, Positive-QTOF	splash10-0fbc-5950000000-2a23375d7108cfc0c1f3	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
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

Curdione

METLIN ID

Not Available

PubChem Compound

5362828

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1529501

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 Curdione (HMDB0034714)

MOL for HMDB0034714 (Curdione)

3D MOL for HMDB0034714 (Curdione)

3D SDF for HMDB0034714 (Curdione)

3D-SDF for HMDB0034714 (Curdione)

PDB for HMDB0034714 (Curdione)

3D PDB for HMDB0034714 (Curdione)

SMILES for HMDB0034714 (Curdione)

INCHI for HMDB0034714 (Curdione)

Structure for HMDB0034714 (Curdione)

3D Structure for HMDB0034714 (Curdione)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra