NP-MRD: Showing NP-Card for (6r)-6-[(2r,4r,5e)-2,4-dihydroxy-6-phenylhex-5-en-1-yl]-5,6-dihydropyran-2-one (NP0216132)

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Record Information

Version

2.0

Created at

2022-09-05 15:58:35 UTC

Updated at

2022-09-05 15:58:35 UTC

NP-MRD ID

NP0216132

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(6r)-6-[(2r,4r,5e)-2,4-dihydroxy-6-phenylhex-5-en-1-yl]-5,6-dihydropyran-2-one

Description

J3.495.849A belongs to the class of organic compounds known as cinnamyl alcohols. These are aromatic alcohols containing a 3-phenylprop-2-en-1-ol moiety. (6r)-6-[(2r,4r,5e)-2,4-dihydroxy-6-phenylhex-5-en-1-yl]-5,6-dihydropyran-2-one is found in Cryptocarya moschata. Based on a literature review very few articles have been published on J3.495.849A.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 41 42  0  0  0  0  0  0  0  0999 V2000
   -6.1899    2.7214   -0.3395 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6413    1.6207   -0.0913 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3647    0.4310    0.3590 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7622   -0.7163    0.6143 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2949   -0.8341    0.4475 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8414    0.1485   -0.5778 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3290    0.1457   -0.7551 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6343    0.4978    0.5412 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.0503    1.7739    0.9694 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1580    0.6342    0.2790 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5331   -0.5887   -0.1809 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1198   -1.1517   -1.3537 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9837   -0.2299   -0.3697 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9166   -0.7362    0.3910 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3354   -0.4349    0.2658 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2078   -1.0538    1.1511 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5639   -0.8239    1.1008 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0426    0.0444    0.1413 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1867    0.6645   -0.7428 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8118    0.4171   -0.6748 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2535    1.4618   -0.2364 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4457    0.5267    0.4798 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3958   -1.5318    0.9415 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0497   -1.8711    0.1428 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8505   -0.6405    1.4538 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2713   -0.1457   -1.5553 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0828   -0.8690   -1.0821 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0707    0.9224   -1.4972 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8112   -0.2196    1.3401 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6973    2.4749    0.3763 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3240    0.9243    1.2637 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0339    1.4850   -0.4193 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4370   -1.3578    0.6310 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0042   -2.1159   -1.3532 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2237    0.4530   -1.1471 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5604   -1.4326    1.1653 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7984   -1.7393    1.9035 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2392   -1.3170    1.8029 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1152    0.2117    0.1189 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5825    1.3334   -1.4776 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1750    0.9175   -1.3793 H   0  0  0  0  0  0  0  0  0  0  0  0
  9  8  1  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
  8  7  1  0
  7  6  1  0
  6  5  1  0
  5  4  1  0
  4  3  2  0
  3  2  1  0
  2  1  2  0
  2 21  1  0
 20 15  1  0
 21  6  1  0
  9 30  1  0
  8 29  1  1
 10 31  1  0
 10 32  1  0
 11 33  1  1
 12 34  1  0
 13 35  1  0
 14 36  1  0
 16 37  1  0
 17 38  1  0
 18 39  1  0
 19 40  1  0
 20 41  1  0
  7 27  1  0
  7 28  1  0
  6 26  1  6
  5 24  1  0
  5 25  1  0
  4 23  1  0
  3 22  1  0
M  END


  Mrv1652309052217582D          

 21 22  0  0  1  0            999 V2000
   -1.4289   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -3.7125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4289   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -3.7125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5724   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  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
  7  8  1  0  0  0  0
  8  9  1  6  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  1  0  0  0
 11 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 15 20  1  0  0  0  0
  6 21  1  0  0  0  0
  2 21  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0216132

> <DATABASE_NAME>
NP-MRD

> <SMILES>
O[C@H](C[C@@H](O)\C=C\C1=CC=CC=C1)C[C@H]1CC=CC(=O)O1

> <INCHI_IDENTIFIER>
InChI=1S/C17H20O4/c18-14(10-9-13-5-2-1-3-6-13)11-15(19)12-16-7-4-8-17(20)21-16/h1-6,8-10,14-16,18-19H,7,11-12H2/b10-9+/t14-,15+,16+/m0/s1

> <INCHI_KEY>
GOQOIZFMLWZVMB-GLBZDCTLSA-N

> <FORMULA>
C17H20O4

> <MOLECULAR_WEIGHT>
288.343

> <EXACT_MASS>
288.136159124

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
41

> <JCHEM_AVERAGE_POLARIZABILITY>
31.730521541372312

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(6R)-6-[(2R,4R,5E)-2,4-dihydroxy-6-phenylhex-5-en-1-yl]-5,6-dihydro-2H-pyran-2-one

> <JCHEM_LOGP>
2.078682248333333

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.357237438713103

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.61338082388152

> <JCHEM_PKA_STRONGEST_BASIC>
-2.7633652985815758

> <JCHEM_POLAR_SURFACE_AREA>
66.76

> <JCHEM_REFRACTIVITY>
82.25960000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(6R)-6-[(2R,4R,5E)-2,4-dihydroxy-6-phenylhex-5-en-1-yl]-5,6-dihydropyran-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 05-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-SEP-22         0                                  
HETATM    1  O   UNK     0      -2.667  -7.700   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      -1.334  -6.930   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.667  -7.700   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       4.001  -5.390   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       5.335  -7.700   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.668  -6.930   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       6.668  -5.390   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       8.002  -7.700   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.336  -6.930   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      10.669  -7.700   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      12.003  -6.930   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      13.337  -7.700   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      13.337  -9.240   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      12.003 -10.010   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      10.669  -9.240   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       0.000  -7.700   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   21                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   21                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   20                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   15                                                       
CONECT   21    6    2                                                       
MASTER        0    0    0    0    0    0    0    0   21    0   44    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₇H₂₀O₄

Average Mass

288.3430 Da

Monoisotopic Mass

288.13616 Da

IUPAC Name

(6R)-6-[(2R,4R,5E)-2,4-dihydroxy-6-phenylhex-5-en-1-yl]-5,6-dihydro-2H-pyran-2-one

Traditional Name

(6R)-6-[(2R,4R,5E)-2,4-dihydroxy-6-phenylhex-5-en-1-yl]-5,6-dihydropyran-2-one

CAS Registry Number

Not Available

SMILES

O[C@H](C[C@@H](O)\C=C\C1=CC=CC=C1)C[C@H]1CC=CC(=O)O1

InChI Identifier

InChI=1S/C17H20O4/c18-14(10-9-13-5-2-1-3-6-13)11-15(19)12-16-7-4-8-17(20)21-16/h1-6,8-10,14-16,18-19H,7,11-12H2/b10-9+/t14-,15+,16+/m0/s1

InChI Key

GOQOIZFMLWZVMB-GLBZDCTLSA-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
Cryptocarya moschata	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cinnamyl alcohols. These are aromatic alcohols containing a 3-phenylprop-2-en-1-ol moiety.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Cinnamyl alcohols

Sub Class

Not Available

Direct Parent

Cinnamyl alcohols

Alternative Parents

Substituents

Cinnamyl alcohol
Fatty alcohol
Styrene
Dihydropyranone
Monocyclic benzene moiety
Pyran
Benzenoid
Fatty acyl
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Secondary alcohol
Lactone
Carboxylic acid ester
Oxacycle
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organoheterocyclic compound
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Alcohol
Carbonyl group
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic 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	2.08	ChemAxon
pKa (Strongest Acidic)	14.61	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	66.76 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	82.26 m³·mol⁻¹	ChemAxon
Polarizability	31.73 Å³	ChemAxon
Number of Rings	2	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

32055519

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

60143302

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (6r)-6-[(2r,4r,5e)-2,4-dihydroxy-6-phenylhex-5-en-1-yl]-5,6-dihydropyran-2-one (NP0216132)

MOL for NP0216132 ((6r)-6-[(2r,4r,5e)-2,4-dihydroxy-6-phenylhex-5-en-1-yl]-5,6-dihydropyran-2-one)

3D MOL for NP0216132 ((6r)-6-[(2r,4r,5e)-2,4-dihydroxy-6-phenylhex-5-en-1-yl]-5,6-dihydropyran-2-one)

3D SDF for NP0216132 ((6r)-6-[(2r,4r,5e)-2,4-dihydroxy-6-phenylhex-5-en-1-yl]-5,6-dihydropyran-2-one)

3D-SDF for NP0216132 ((6r)-6-[(2r,4r,5e)-2,4-dihydroxy-6-phenylhex-5-en-1-yl]-5,6-dihydropyran-2-one)

PDB for NP0216132 ((6r)-6-[(2r,4r,5e)-2,4-dihydroxy-6-phenylhex-5-en-1-yl]-5,6-dihydropyran-2-one)

3D PDB for NP0216132 ((6r)-6-[(2r,4r,5e)-2,4-dihydroxy-6-phenylhex-5-en-1-yl]-5,6-dihydropyran-2-one)

SMILES for NP0216132 ((6r)-6-[(2r,4r,5e)-2,4-dihydroxy-6-phenylhex-5-en-1-yl]-5,6-dihydropyran-2-one)

INCHI for NP0216132 ((6r)-6-[(2r,4r,5e)-2,4-dihydroxy-6-phenylhex-5-en-1-yl]-5,6-dihydropyran-2-one)

Structure for NP0216132 ((6r)-6-[(2r,4r,5e)-2,4-dihydroxy-6-phenylhex-5-en-1-yl]-5,6-dihydropyran-2-one)

3D Structure for NP0216132 ((6r)-6-[(2r,4r,5e)-2,4-dihydroxy-6-phenylhex-5-en-1-yl]-5,6-dihydropyran-2-one)