NP-MRD: Showing NP-Card for (1s,2s,5s,6s,7r,8s,9r,12r)-5,12-bis(acetyloxy)-6-[(acetyloxy)methyl]-2,8-dihydroxy-2,10,10-trimethyl-11-oxatricyclo[7.2.1.0¹,⁶]dodecan-7-yl (2e)-3-phenylprop-2-enoate (NP0284292)

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Record Information

Version

2.0

Created at

2022-09-09 11:55:52 UTC

Updated at

2022-09-09 11:55:52 UTC

NP-MRD ID

NP0284292

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,2s,5s,6s,7r,8s,9r,12r)-5,12-bis(acetyloxy)-6-[(acetyloxy)methyl]-2,8-dihydroxy-2,10,10-trimethyl-11-oxatricyclo[7.2.1.0¹,⁶]dodecan-7-yl (2e)-3-phenylprop-2-enoate

Description

CHEMBL3394870 belongs to the class of organic compounds known as agarofurans. These are organic compounds containing an agarofuran moiety( a three-ring system, with core fragment oxatricyclo[7.2.1.0^{1,6}]Dodec-2-ene). (1s,2s,5s,6s,7r,8s,9r,12r)-5,12-bis(acetyloxy)-6-[(acetyloxy)methyl]-2,8-dihydroxy-2,10,10-trimethyl-11-oxatricyclo[7.2.1.0¹,⁶]dodecan-7-yl (2e)-3-phenylprop-2-enoate is found in Denhamia celastroides. Based on a literature review very few articles have been published on CHEMBL3394870.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309092213552D          

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M  END

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M  END


  Mrv1652309092213552D          

 41 44  0  0  1  0            999 V2000
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    0.5304    2.2931    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6408    3.3396    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5130    4.3314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2120    4.8069    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8974    5.1367    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7256    5.9803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3433    6.5271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1786    7.3355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7964    7.8823    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5788    7.6207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7435    6.8123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1257    6.2655    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0175    1.1439    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1799    1.9390    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2111    2.8170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8691    3.3685    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5177    3.6251    0.0000 O   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
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  6  5  1  1  0  0  0
  6  7  1  0  0  0  0
  7  8  1  1  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  2  0  0  0  0
  7 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  1  0  0  0
 14 16  1  6  0  0  0
 14 17  1  0  0  0  0
  6 17  1  0  0  0  0
 17 18  1  6  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  1  0  0  0  0
 22 19  1  6  0  0  0
 22 23  1  0  0  0  0
 23 24  1  6  0  0  0
 23 25  1  0  0  0  0
  6 25  1  0  0  0  0
 25 26  1  6  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 27 29  1  0  0  0  0
 29 30  2  0  0  0  0
 30 31  1  0  0  0  0
 31 32  2  0  0  0  0
 32 33  1  0  0  0  0
 33 34  2  0  0  0  0
 34 35  1  0  0  0  0
 35 36  2  0  0  0  0
 31 36  1  0  0  0  0
 22 37  1  0  0  0  0
 17 37  1  0  0  0  0
 37 38  1  1  0  0  0
 38 39  1  0  0  0  0
 39 40  1  0  0  0  0
 39 41  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0284292

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)OC[C@@]12[C@H](CC[C@](C)(O)[C@]11OC(C)(C)[C@@H]([C@H]1OC(C)=O)[C@H](O)[C@@H]2OC(=O)\C=C\C1=CC=CC=C1)OC(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C30H38O11/c1-17(31)37-16-29-21(38-18(2)32)14-15-28(6,36)30(29)25(39-19(3)33)23(27(4,5)41-30)24(35)26(29)40-22(34)13-12-20-10-8-7-9-11-20/h7-13,21,23-26,35-36H,14-16H2,1-6H3/b13-12+/t21-,23+,24-,25+,26-,28-,29-,30-/m0/s1

> <INCHI_KEY>
PVKRLWLUFLRCHV-PVXREPHISA-N

> <FORMULA>
C30H38O11

> <MOLECULAR_WEIGHT>
574.623

> <EXACT_MASS>
574.241412044

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
79

> <JCHEM_AVERAGE_POLARIZABILITY>
59.25020001955626

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,2S,5S,6S,7R,8S,9R,12R)-5,12-bis(acetyloxy)-6-[(acetyloxy)methyl]-2,8-dihydroxy-2,10,10-trimethyl-11-oxatricyclo[7.2.1.0^{1,6}]dodecan-7-yl (2E)-3-phenylprop-2-enoate

> <JCHEM_LOGP>
1.5681338236666669

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.039144889134079

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.43601317805048

> <JCHEM_PKA_STRONGEST_BASIC>
-3.3435834130318476

> <JCHEM_POLAR_SURFACE_AREA>
154.89

> <JCHEM_REFRACTIVITY>
142.14440000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2S,5S,6S,7R,8S,9R,12R)-5,12-bis(acetyloxy)-6-[(acetyloxy)methyl]-2,8-dihydroxy-2,10,10-trimethyl-11-oxatricyclo[7.2.1.0^{1,6}]dodecan-7-yl (2E)-3-phenylprop-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

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       6.423   1.974   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.419   3.788   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       8.102   3.858   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       4.856   4.573   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       3.222   4.149   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.844   2.878   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.416   2.926   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       5.212   3.496   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       6.222   5.140   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.985   6.786   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       7.662   6.061   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       4.254   1.619   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.558   0.233   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.018   0.139   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.692  -1.377   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       1.149  -1.261   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       1.084   1.407   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -0.188   0.322   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      -1.607   1.111   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -3.165   1.617   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -2.739  -0.073   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -1.298   2.693   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -0.611   4.154   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      -2.293   4.608   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       0.990   4.280   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       1.196   6.234   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       0.958   8.085   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      -0.396   8.973   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       1.675   9.589   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       1.354  11.163   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       2.508  12.184   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       2.200  13.693   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       3.353  14.714   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       4.814  14.225   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       5.121  12.716   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       3.968  11.696   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      -0.033   2.135   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0       0.336   3.620   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0      -0.394   5.258   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      -1.622   6.288   0.000  0.00  0.00           C+0
HETATM   41  O   UNK     0      -0.966   6.767   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   17   25                                             
CONECT    7    6    8   12                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9                                                            
CONECT   12    7   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   16   17                                             
CONECT   15   14                                                            
CONECT   16   14                                                            
CONECT   17   14    6   18   37                                             
CONECT   18   17   19                                                       
CONECT   19   18   20   21   22                                             
CONECT   20   19                                                            
CONECT   21   19                                                            
CONECT   22   19   23   37                                                  
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23    6   26                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   32   36                                                  
CONECT   32   31   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33   35                                                       
CONECT   35   34   36                                                       
CONECT   36   35   31                                                       
CONECT   37   22   17   38                                                  
CONECT   38   37   39                                                       
CONECT   39   38   40   41                                                  
CONECT   40   39                                                            
CONECT   41   39                                                            
MASTER        0    0    0    0    0    0    0    0   41    0   88    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₀H₃₈O₁₁

Average Mass

574.6230 Da

Monoisotopic Mass

574.24141 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

CC(=O)OC[C@@]12[C@H](CC[C@](C)(O)[C@]11OC(C)(C)[C@@H]([C@H]1OC(C)=O)[C@H](O)[C@@H]2OC(=O)\C=C\C1=CC=CC=C1)OC(C)=O

InChI Identifier

InChI=1S/C30H38O11/c1-17(31)37-16-29-21(38-18(2)32)14-15-28(6,36)30(29)25(39-19(3)33)23(27(4,5)41-30)24(35)26(29)40-22(34)13-12-20-10-8-7-9-11-20/h7-13,21,23-26,35-36H,14-16H2,1-6H3/b13-12+/t21-,23+,24-,25+,26-,28-,29-,30-/m0/s1

InChI Key

PVKRLWLUFLRCHV-PVXREPHISA-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
Denhamia celastroides	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as agarofurans. These are organic compounds containing an agarofuran moiety( a three-ring system, with core fragment oxatricyclo[7.2.1.0^{1,6}]Dodec-2-ene).

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Agarofurans

Alternative Parents

Substituents

Agarofuran
Tetracarboxylic acid or derivatives
Cinnamic acid or derivatives
Cinnamic acid ester
Styrene
Fatty acid ester
Oxepane
Monocyclic benzene moiety
Fatty acyl
Benzenoid
Cyclic alcohol
Alpha,beta-unsaturated carboxylic ester
Tertiary alcohol
Enoate ester
Tetrahydrofuran
Carboxylic acid ester
Secondary alcohol
Organoheterocyclic compound
Oxacycle
Ether
Dialkyl ether
Carboxylic acid derivative
Organooxygen compound
Organic oxygen compound
Hydrocarbon derivative
Alcohol
Organic oxide
Carbonyl group
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic 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

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

58989256

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

118726317

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1s,2s,5s,6s,7r,8s,9r,12r)-5,12-bis(acetyloxy)-6-[(acetyloxy)methyl]-2,8-dihydroxy-2,10,10-trimethyl-11-oxatricyclo[7.2.1.0¹,⁶]dodecan-7-yl (2e)-3-phenylprop-2-enoate (NP0284292)

MOL for NP0284292 ((1s,2s,5s,6s,7r,8s,9r,12r)-5,12-bis(acetyloxy)-6-[(acetyloxy)methyl]-2,8-dihydroxy-2,10,10-trimethyl-11-oxatricyclo[7.2.1.0¹,⁶]dodecan-7-yl (2e)-3-phenylprop-2-enoate)

3D MOL for NP0284292 ((1s,2s,5s,6s,7r,8s,9r,12r)-5,12-bis(acetyloxy)-6-[(acetyloxy)methyl]-2,8-dihydroxy-2,10,10-trimethyl-11-oxatricyclo[7.2.1.0¹,⁶]dodecan-7-yl (2e)-3-phenylprop-2-enoate)

3D SDF for NP0284292 ((1s,2s,5s,6s,7r,8s,9r,12r)-5,12-bis(acetyloxy)-6-[(acetyloxy)methyl]-2,8-dihydroxy-2,10,10-trimethyl-11-oxatricyclo[7.2.1.0¹,⁶]dodecan-7-yl (2e)-3-phenylprop-2-enoate)

3D-SDF for NP0284292 ((1s,2s,5s,6s,7r,8s,9r,12r)-5,12-bis(acetyloxy)-6-[(acetyloxy)methyl]-2,8-dihydroxy-2,10,10-trimethyl-11-oxatricyclo[7.2.1.0¹,⁶]dodecan-7-yl (2e)-3-phenylprop-2-enoate)

PDB for NP0284292 ((1s,2s,5s,6s,7r,8s,9r,12r)-5,12-bis(acetyloxy)-6-[(acetyloxy)methyl]-2,8-dihydroxy-2,10,10-trimethyl-11-oxatricyclo[7.2.1.0¹,⁶]dodecan-7-yl (2e)-3-phenylprop-2-enoate)

3D PDB for NP0284292 ((1s,2s,5s,6s,7r,8s,9r,12r)-5,12-bis(acetyloxy)-6-[(acetyloxy)methyl]-2,8-dihydroxy-2,10,10-trimethyl-11-oxatricyclo[7.2.1.0¹,⁶]dodecan-7-yl (2e)-3-phenylprop-2-enoate)

SMILES for NP0284292 ((1s,2s,5s,6s,7r,8s,9r,12r)-5,12-bis(acetyloxy)-6-[(acetyloxy)methyl]-2,8-dihydroxy-2,10,10-trimethyl-11-oxatricyclo[7.2.1.0¹,⁶]dodecan-7-yl (2e)-3-phenylprop-2-enoate)

INCHI for NP0284292 ((1s,2s,5s,6s,7r,8s,9r,12r)-5,12-bis(acetyloxy)-6-[(acetyloxy)methyl]-2,8-dihydroxy-2,10,10-trimethyl-11-oxatricyclo[7.2.1.0¹,⁶]dodecan-7-yl (2e)-3-phenylprop-2-enoate)

Structure for NP0284292 ((1s,2s,5s,6s,7r,8s,9r,12r)-5,12-bis(acetyloxy)-6-[(acetyloxy)methyl]-2,8-dihydroxy-2,10,10-trimethyl-11-oxatricyclo[7.2.1.0¹,⁶]dodecan-7-yl (2e)-3-phenylprop-2-enoate)

3D Structure for NP0284292 ((1s,2s,5s,6s,7r,8s,9r,12r)-5,12-bis(acetyloxy)-6-[(acetyloxy)methyl]-2,8-dihydroxy-2,10,10-trimethyl-11-oxatricyclo[7.2.1.0¹,⁶]dodecan-7-yl (2e)-3-phenylprop-2-enoate)