NP-MRD: Showing NP-Card for 1-[2-(hydroxymethyl)pyrrolidin-1-yl]-2-methyldec-6-ene-1,3-dione (NP0216984)

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Record Information

Version

2.0

Created at

2022-09-05 17:10:01 UTC

Updated at

2022-09-05 17:10:01 UTC

NP-MRD ID

NP0216984

Secondary Accession Numbers

None

Natural Product Identification

Common Name

1-[2-(hydroxymethyl)pyrrolidin-1-yl]-2-methyldec-6-ene-1,3-dione

Description

1-[2-(Hydroxymethyl)pyrrolidin-1-yl]-2-methyldec-6-ene-1,3-dione belongs to the class of organic compounds known as n-acylpyrrolidines. These are n-Acylated Pyrrolidine derivatives. Pyrrolidine is a five-membered saturated aliphatic heterocycle with one nitrogen atom and four carbon atoms. 1-[2-(hydroxymethyl)pyrrolidin-1-yl]-2-methyldec-6-ene-1,3-dione is found in Penicillium citrinum. 1-[2-(Hydroxymethyl)pyrrolidin-1-yl]-2-methyldec-6-ene-1,3-dione is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 47 47  0  0  0  0  0  0  0  0999 V2000
    5.8768   -1.0857    1.6919 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3603   -1.4542    0.3333 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9672   -0.2131   -0.4640 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9201    0.5522    0.2085 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7516    0.8030   -0.2890 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2615    0.3688   -1.6131 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0424   -0.5097   -1.4311 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0312    0.2163   -0.7494 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0242    0.3363    0.4806 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1964    0.8249   -1.4354 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7601    1.8699   -2.4535 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1317    1.3766   -0.4511 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0853    2.6616   -0.3449 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0401    0.6916    0.3657 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8785    1.4273    1.3439 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0709    0.5918    1.6340 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9793   -0.5058    0.5985 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4479   -0.6640    0.5311 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.0536   -1.6356   -0.5175 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5852   -2.9061   -0.1642 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9258   -1.4292    1.7743 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3291   -1.5772    2.5240 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8902    0.0099    1.8638 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1459   -1.9566   -0.2495 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4512   -2.0815    0.4543 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8730    0.4504   -0.5542 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6859   -0.4628   -1.4880 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1054    0.9666    1.2291 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0368    1.4036    0.3085 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9974   -0.0973   -2.2639 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8536    1.3174   -2.0928 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7119   -0.9103   -2.4261 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3594   -1.4030   -0.8176 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6623    0.0119   -2.0497 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6813    2.2899   -2.9251 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1203    2.6515   -2.0250 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2063    1.3935   -3.2859 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2452    1.6129    2.2599 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2126    2.3812    0.8796 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0272    1.1565    1.5592 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9695    0.1156    2.6546 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3381   -0.0661   -0.3601 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4807   -1.4302    0.8761 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1197   -1.0088    1.5418 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9682   -1.8006   -0.5154 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5001   -1.4113   -1.4958 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7779   -2.8719    0.7884 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 10 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 18 14  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  2 24  1  0
  2 25  1  0
  3 26  1  0
  3 27  1  0
  4 28  1  0
  5 29  1  0
  6 30  1  0
  6 31  1  0
  7 32  1  0
  7 33  1  0
 10 34  1  6
 11 35  1  0
 11 36  1  0
 11 37  1  0
 15 38  1  0
 15 39  1  0
 16 40  1  0
 16 41  1  0
 17 42  1  0
 17 43  1  0
 18 44  1  1
 19 45  1  0
 19 46  1  0
 20 47  1  0
M  END


  Mrv1533004191519562D          

 20 20  0  0  0  0            999 V2000
   -1.6980   -0.9475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9836   -1.3600    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9836   -2.1850    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2691   -2.5975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2691   -3.4225    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4454   -3.8350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1598   -3.4225    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8743   -3.8350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8743   -4.6600    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5888   -3.4225    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5888   -2.5975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3033   -3.8350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3033   -4.6600    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0177   -3.4225    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1040   -2.6020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9109   -2.4305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3234   -3.1450    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7714   -3.7581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9429   -4.5650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7276   -4.8200    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  4  3  1  4  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  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
 10 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 14 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0216984

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCC=CCCC(=O)C(C)C(=O)N1CCCC1CO

> <INCHI_IDENTIFIER>
InChI=1S/C16H27NO3/c1-3-4-5-6-7-10-15(19)13(2)16(20)17-11-8-9-14(17)12-18/h5-6,13-14,18H,3-4,7-12H2,1-2H3

> <INCHI_KEY>
HFWMLSNVDWMIEV-UHFFFAOYSA-N

> <FORMULA>
C16H27NO3

> <MOLECULAR_WEIGHT>
281.396

> <EXACT_MASS>
281.199093733

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
47

> <JCHEM_AVERAGE_POLARIZABILITY>
32.443484357979074

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1-[2-(hydroxymethyl)pyrrolidin-1-yl]-2-methyldec-6-ene-1,3-dione

> <ALOGPS_LOGP>
2.57

> <JCHEM_LOGP>
2.5188240903333345

> <ALOGPS_LOGS>
-2.44

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.098514581697614

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.940713037192243

> <JCHEM_PKA_STRONGEST_BASIC>
-2.757486975635402

> <JCHEM_POLAR_SURFACE_AREA>
57.61

> <JCHEM_REFRACTIVITY>
80.98100000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.01e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1-[2-(hydroxymethyl)pyrrolidin-1-yl]-2-methyldec-6-ene-1,3-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 19-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-APR-15         0                                  
HETATM    1  C   UNK     0      -3.170  -1.769   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.836  -2.539   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.836  -4.079   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.502  -4.849   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.502  -6.389   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.831  -7.159   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.165  -6.389   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.499  -7.159   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       3.499  -8.699   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       4.832  -6.389   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.832  -4.849   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.166  -7.159   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       6.166  -8.699   0.000  0.00  0.00           O+0
HETATM   14  N   UNK     0       7.500  -6.389   0.000  0.00  0.00           N+0
HETATM   15  C   UNK     0       7.661  -4.857   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       9.167  -4.537   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       9.937  -5.871   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.907  -7.015   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       9.227  -8.521   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      10.691  -8.997   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15   18                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   14   19                                                  
CONECT   19   18   20                                                       
CONECT   20   19                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   40    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₆H₂₇NO₃

Average Mass

281.3960 Da

Monoisotopic Mass

281.19909 Da

IUPAC Name

1-[2-(hydroxymethyl)pyrrolidin-1-yl]-2-methyldec-6-ene-1,3-dione

Traditional Name

1-[2-(hydroxymethyl)pyrrolidin-1-yl]-2-methyldec-6-ene-1,3-dione

CAS Registry Number

Not Available

SMILES

CCCC=CCCC(=O)C(C)C(=O)N1CCCC1CO

InChI Identifier

InChI=1S/C16H27NO3/c1-3-4-5-6-7-10-15(19)13(2)16(20)17-11-8-9-14(17)12-18/h5-6,13-14,18H,3-4,7-12H2,1-2H3

InChI Key

HFWMLSNVDWMIEV-UHFFFAOYSA-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
Penicillium citrinum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as n-acylpyrrolidines. These are n-Acylated Pyrrolidine derivatives. Pyrrolidine is a five-membered saturated aliphatic heterocycle with one nitrogen atom and four carbon atoms.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Pyrrolidines

Sub Class

N-acylpyrrolidines

Direct Parent

N-acylpyrrolidines

Alternative Parents

Substituents

N-acylpyrrolidine
1,3-dicarbonyl compound
Tertiary carboxylic acid amide
Carboxamide group
Ketone
Carboxylic acid derivative
Azacycle
Primary alcohol
Organooxygen compound
Organonitrogen compound
Organic oxide
Organic oxygen compound
Alcohol
Organic nitrogen compound
Carbonyl group
Hydrocarbon derivative
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic 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	2.57	ALOGPS
logP	2.52	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Acidic)	11.94	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	57.61 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	80.98 m³·mol⁻¹	ChemAxon
Polarizability	32.44 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	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

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

72756347

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 1-[2-(hydroxymethyl)pyrrolidin-1-yl]-2-methyldec-6-ene-1,3-dione (NP0216984)

MOL for NP0216984 (1-[2-(hydroxymethyl)pyrrolidin-1-yl]-2-methyldec-6-ene-1,3-dione)

3D MOL for NP0216984 (1-[2-(hydroxymethyl)pyrrolidin-1-yl]-2-methyldec-6-ene-1,3-dione)

3D SDF for NP0216984 (1-[2-(hydroxymethyl)pyrrolidin-1-yl]-2-methyldec-6-ene-1,3-dione)

3D-SDF for NP0216984 (1-[2-(hydroxymethyl)pyrrolidin-1-yl]-2-methyldec-6-ene-1,3-dione)

PDB for NP0216984 (1-[2-(hydroxymethyl)pyrrolidin-1-yl]-2-methyldec-6-ene-1,3-dione)

3D PDB for NP0216984 (1-[2-(hydroxymethyl)pyrrolidin-1-yl]-2-methyldec-6-ene-1,3-dione)

SMILES for NP0216984 (1-[2-(hydroxymethyl)pyrrolidin-1-yl]-2-methyldec-6-ene-1,3-dione)

INCHI for NP0216984 (1-[2-(hydroxymethyl)pyrrolidin-1-yl]-2-methyldec-6-ene-1,3-dione)

Structure for NP0216984 (1-[2-(hydroxymethyl)pyrrolidin-1-yl]-2-methyldec-6-ene-1,3-dione)

3D Structure for NP0216984 (1-[2-(hydroxymethyl)pyrrolidin-1-yl]-2-methyldec-6-ene-1,3-dione)