NP-MRD: Showing NP-Card for (3r,6e,10s)-3-isopropyl-6,10-dimethylcyclodec-6-ene-1,4-dione (NP0281837)

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Record Information

Version

2.0

Created at

2022-09-09 08:25:30 UTC

Updated at

2022-09-09 08:25:30 UTC

NP-MRD ID

NP0281837

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(3r,6e,10s)-3-isopropyl-6,10-dimethylcyclodec-6-ene-1,4-dione

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. (3r,6e,10s)-3-isopropyl-6,10-dimethylcyclodec-6-ene-1,4-dione is found in Curcuma aromatica. (3r,6e,10s)-3-isopropyl-6,10-dimethylcyclodec-6-ene-1,4-dione was first documented in 2021 (PMID: 34858986). Based on a literature review a small amount of articles have been published on Curdione (PMID: 35718518) (PMID: 35534245) (PMID: 35318816) (PMID: 35178908).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 41 41  0  0  0  0  0  0  0  0999 V2000
   -1.0791    3.5490   -0.5852 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1494    2.2097    0.1116 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3017    1.5751    0.2594 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4328    0.2608    0.9330 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7345   -0.8412   -0.0461 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5017   -1.6128   -0.4596 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.0246   -2.8900   -1.1315 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6298   -1.9675    0.6729 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0504   -2.8418    1.4404 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6952   -1.3601    0.9532 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2499   -0.5983   -0.1967 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7711   -0.5195   -0.0657 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3434    0.2556   -1.2342 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2015    0.0575    1.2440 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6665    0.7230   -0.4185 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6165    1.1569   -1.5739 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1138    1.6201    0.6287 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9346    3.6637   -1.2954 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1639    4.3746    0.1398 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1356    3.6356   -1.1613 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2067    2.0353   -0.1314 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3463    0.3593    1.5928 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6190   -0.0020    1.6056 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1645   -0.3952   -0.9674 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4709   -1.5186    0.3827 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9470   -1.0745   -1.2248 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2209   -3.5622   -1.4247 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6911   -3.3986   -0.3964 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6755   -2.5672   -1.9683 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6247   -0.7990    1.8899 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4119   -2.2079    1.1630 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0830   -1.2266   -1.1213 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1520   -1.5564   -0.1467 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9906    1.2912   -1.2726 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4457    0.2636   -1.1120 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1403   -0.3097   -2.1717 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8177    0.9616    1.0410 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3552    0.2812    1.8934 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8871   -0.6413    1.7968 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8838    2.4422    0.7413 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0306    1.1744    1.6159 H   0  0  0  0  0  0  0  0  0  0  0  0
 13 12  1  0
 12 14  1  0
 12 11  1  0
 11 10  1  0
 10  8  1  0
  8  9  2  0
  8  6  1  0
  6  7  1  0
  6  5  1  0
  5  4  1  0
  4  3  1  0
  3  2  2  0
  2  1  1  0
  2 17  1  0
 17 15  1  0
 15 16  2  0
 15 11  1  0
 13 34  1  0
 13 35  1  0
 13 36  1  0
 12 33  1  0
 14 37  1  0
 14 38  1  0
 14 39  1  0
 11 32  1  6
 10 30  1  0
 10 31  1  0
  6 26  1  6
  7 27  1  0
  7 28  1  0
  7 29  1  0
  5 24  1  0
  5 25  1  0
  4 22  1  0
  4 23  1  0
  3 21  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
 17 40  1  0
 17 41  1  0
M  END


  Mrv1652309092210252D          

 17 17  0  0  1  0            999 V2000
    0.9440    0.1576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    0.0000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  6  0  0  0
  6  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  6  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
 11 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
  2 17  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0281837

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)[C@H]1CC(=O)[C@@H](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+/t12-,13+/m0/s1

> <INCHI_KEY>
KDPFMRXIVDLQKX-OAIDTJHVSA-N

> <FORMULA>
C15H24O2

> <MOLECULAR_WEIGHT>
236.355

> <EXACT_MASS>
236.177630013

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
41

> <JCHEM_AVERAGE_POLARIZABILITY>
27.35105547354344

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <JCHEM_LOGP>
3.786251132333333

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
16.650149575724075

> <JCHEM_PKA_STRONGEST_BASIC>
-7.159488985737964

> <JCHEM_POLAR_SURFACE_AREA>
34.14

> <JCHEM_REFRACTIVITY>
70.99

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

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

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 09-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   09-SEP-22         0                                  
HETATM    1  C   UNK     0       1.762   0.294   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.335  -0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       2.667  -1.540   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.000   0.000   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -2.667   0.000   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.000   1.540   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -1.334   2.310   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   17                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10   12   15                                                  
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12                                                            
CONECT   15   11   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15    2                                                       
MASTER        0    0    0    0    0    0    0    0   17    0   34    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₅H₂₄O₂

Average Mass

236.3550 Da

Monoisotopic Mass

236.17763 Da

IUPAC Name

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

Traditional Name

(3R,6E,10S)-3-isopropyl-6,10-dimethylcyclodec-6-ene-1,4-dione

CAS Registry Number

Not Available

SMILES

CC(C)[C@H]1CC(=O)[C@@H](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+/t12-,13+/m0/s1

InChI Key

KDPFMRXIVDLQKX-OAIDTJHVSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Curcuma aromatica	LOTUS Database	35616633

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

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	3.79	ChemAxon
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	27.35 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

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00011731

Chemspider ID

8642062

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Curdione

METLIN ID

Not Available

PubChem Compound

10466651

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Wang M, Yu MT, Peng MM, Yin ZZ, Mao CQ, Su LL, Ji D, Lu TL: [Quality evaluation of Curcumae Radix from different origins based on UPLC characteristic chromatogram, multicomponent content, and chemometrics]. Zhongguo Zhong Yao Za Zhi. 2022 Jun;47(11):2964-2974. doi: 10.19540/j.cnki.cjcmm.20210823.301. [PubMed:35718518 ]
Li ZY, Hao EW, DU ZC, Cao R, Chen F, Mo LY, Wu DY, Hou XT, Deng JG: [Research progress of Curcuma kwangsiensis root tubers and analysis of liver protection and anti-tumor mechanisms based on Q-markers]. Zhongguo Zhong Yao Za Zhi. 2022 Apr;47(7):1739-1753. doi: 10.19540/j.cnki.cjcmm.20211220.203. [PubMed:35534245 ]
Yang Z, Wang Z, Li J, Long J, Peng C, Yan D: Network pharmacology-based dissection of the underlying mechanisms of dyspnoea induced by zedoary turmeric oil. Basic Clin Pharmacol Toxicol. 2022 May;130(5):606-617. doi: 10.1111/bcpt.13722. Epub 2022 Mar 29. [PubMed:35318816 ]
Qin YW, Fei CH, Zhang W, Li Y, Xu Z, Su LL, Ji D, Mao CQ, Lu TL: [Efficacy-related substances of blood-activating and stasis-resolving medicinals derived from Curcuma plants: a review]. Zhongguo Zhong Yao Za Zhi. 2022 Jan;47(1):24-35. doi: 10.19540/j.cnki.cjcmm.20210817.603. [PubMed:35178908 ]
Dai W, Qin Q, Li Z, Lin L, Li R, Fang Z, Han Y, Mu W, Ren L, Liu T, Zhan X, Xiao X, Bai Z: Curdione and Schisandrin C Synergistically Reverse Hepatic Fibrosis via Modulating the TGF-beta Pathway and Inhibiting Oxidative Stress. Front Cell Dev Biol. 2021 Nov 10;9:763864. doi: 10.3389/fcell.2021.763864. eCollection 2021. [PubMed:34858986 ]
LOTUS database [Link]

Showing NP-Card for (3r,6e,10s)-3-isopropyl-6,10-dimethylcyclodec-6-ene-1,4-dione (NP0281837)

MOL for NP0281837 ((3r,6e,10s)-3-isopropyl-6,10-dimethylcyclodec-6-ene-1,4-dione)

3D MOL for NP0281837 ((3r,6e,10s)-3-isopropyl-6,10-dimethylcyclodec-6-ene-1,4-dione)

3D SDF for NP0281837 ((3r,6e,10s)-3-isopropyl-6,10-dimethylcyclodec-6-ene-1,4-dione)

3D-SDF for NP0281837 ((3r,6e,10s)-3-isopropyl-6,10-dimethylcyclodec-6-ene-1,4-dione)

PDB for NP0281837 ((3r,6e,10s)-3-isopropyl-6,10-dimethylcyclodec-6-ene-1,4-dione)

3D PDB for NP0281837 ((3r,6e,10s)-3-isopropyl-6,10-dimethylcyclodec-6-ene-1,4-dione)

SMILES for NP0281837 ((3r,6e,10s)-3-isopropyl-6,10-dimethylcyclodec-6-ene-1,4-dione)

INCHI for NP0281837 ((3r,6e,10s)-3-isopropyl-6,10-dimethylcyclodec-6-ene-1,4-dione)

Structure for NP0281837 ((3r,6e,10s)-3-isopropyl-6,10-dimethylcyclodec-6-ene-1,4-dione)

3D Structure for NP0281837 ((3r,6e,10s)-3-isopropyl-6,10-dimethylcyclodec-6-ene-1,4-dione)