NP-MRD: Showing NP-Card for 3-ethenyl-1-hydroxy-3,4a,7,7,10a-pentamethyl-10-[(2-methylbut-2-enoyl)oxy]-5-oxo-octahydronaphtho[2,1-b]pyran-8-yl 2,3-dimethyloxirane-2-carboxylate (NP0145544)

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Record Information

Version

2.0

Created at

2022-09-02 00:46:09 UTC

Updated at

2022-09-02 00:46:09 UTC

NP-MRD ID

NP0145544

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3-ethenyl-1-hydroxy-3,4a,7,7,10a-pentamethyl-10-[(2-methylbut-2-enoyl)oxy]-5-oxo-octahydronaphtho[2,1-b]pyran-8-yl 2,3-dimethyloxirane-2-carboxylate

Description

3-Ethenyl-1-hydroxy-3,4a,7,7,10a-pentamethyl-10-[(2-methylbut-2-enoyl)oxy]-5-oxo-dodecahydro-1H-naphtho[2,1-b]pyran-8-yl 2,3-dimethyloxirane-2-carboxylate belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units. Based on a literature review very few articles have been published on 3-ethenyl-1-hydroxy-3,4a,7,7,10a-pentamethyl-10-[(2-methylbut-2-enoyl)oxy]-5-oxo-dodecahydro-1H-naphtho[2,1-b]pyran-8-yl 2,3-dimethyloxirane-2-carboxylate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309022202462D          

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M  END

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M  END


  Mrv1652309022202462D          

 38 41  0  0  0  0            999 V2000
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   -2.3163    0.3145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9483    0.8448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7607    0.9881    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395    1.8414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020    2.5559    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395    3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270    3.9849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395    4.6993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9520    1.1270    0.0000 C   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  1  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
  3 11  1  0  0  0  0
  9 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
 16 18  1  0  0  0  0
 16 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
 23 25  1  0  0  0  0
 25 26  1  0  0  0  0
 23 26  1  0  0  0  0
 26 27  1  0  0  0  0
 19 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  2  0  0  0  0
 31 33  1  0  0  0  0
 33 34  1  0  0  0  0
 33 35  2  0  0  0  0
 35 36  1  4  0  0  0
 29 37  1  0  0  0  0
  8 37  1  0  0  0  0
 15 37  1  0  0  0  0
 37 38  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0145544

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC=C(C)C(=O)OC1CC(OC(=O)C2(C)OC2C)C(C)(C)C2CC(=O)C3(C)OC(C)(CC(O)C3C12C)C=C

> <INCHI_IDENTIFIER>
InChI=1S/C30H44O8/c1-11-16(3)24(33)35-22-14-21(36-25(34)29(9)17(4)37-29)26(5,6)19-13-20(32)30(10)23(28(19,22)8)18(31)15-27(7,12-2)38-30/h11-12,17-19,21-23,31H,2,13-15H2,1,3-10H3

> <INCHI_KEY>
MAMRCICAQFISBT-UHFFFAOYSA-N

> <FORMULA>
C30H44O8

> <MOLECULAR_WEIGHT>
532.674

> <EXACT_MASS>
532.303618377

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
82

> <JCHEM_AVERAGE_POLARIZABILITY>
57.81419858511161

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-ethenyl-1-hydroxy-3,4a,7,7,10a-pentamethyl-10-[(2-methylbut-2-enoyl)oxy]-5-oxo-dodecahydro-1H-naphtho[2,1-b]pyran-8-yl 2,3-dimethyloxirane-2-carboxylate

> <ALOGPS_LOGP>
4.26

> <JCHEM_LOGP>
4.404527271666668

> <ALOGPS_LOGS>
-5.23

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
17.439421684918404

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.715880295324446

> <JCHEM_PKA_STRONGEST_BASIC>
-2.922640710717398

> <JCHEM_POLAR_SURFACE_AREA>
111.66000000000003

> <JCHEM_REFRACTIVITY>
140.8696

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.14e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-ethenyl-1-hydroxy-3,4a,7,7,10a-pentamethyl-10-[(2-methylbut-2-enoyl)oxy]-5-oxo-octahydronaphtho[2,1-b]pyran-8-yl 2,3-dimethyloxirane-2-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 02-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-SEP-22         0                                  
HETATM    1  C   UNK     0      10.121   1.233   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.673   1.760   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.494   0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.673  -0.220   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.724   2.104   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.184   2.104   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       4.414   3.437   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       4.414   0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.184  -0.564   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.954  -1.897   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       6.724  -0.564   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       4.414  -1.897   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       5.184  -3.231   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       2.874  -1.897   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.104  -0.564   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.564  -0.564   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.831  -2.080   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -0.883  -1.090   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -0.206   0.770   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      -1.746   0.770   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      -2.516   2.104   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      -1.746   3.437   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      -4.056   2.104   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -4.324   3.620   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      -4.324   0.587   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      -5.503   1.577   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -7.020   1.844   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       0.564   2.104   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       2.104   2.104   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       2.874   3.437   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       2.104   4.771   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       0.564   4.771   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       2.874   6.105   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       4.414   6.105   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       2.104   7.438   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       2.874   8.772   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       2.874   0.770   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       3.644   2.104   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5   11                                             
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   37                                                  
CONECT    9    8   10   11   12                                             
CONECT   10    9                                                            
CONECT   11    9    3                                                       
CONECT   12    9   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14   16   37                                                  
CONECT   16   15   17   18   19                                             
CONECT   17   16                                                            
CONECT   18   16                                                            
CONECT   19   16   20   28                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24   25   26                                             
CONECT   24   23                                                            
CONECT   25   23   26                                                       
CONECT   26   25   23   27                                                  
CONECT   27   26                                                            
CONECT   28   19   29                                                       
CONECT   29   28   30   37                                                  
CONECT   30   29   31                                                       
CONECT   31   30   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33   36                                                       
CONECT   36   35                                                            
CONECT   37   29    8   15   38                                             
CONECT   38   37                                                            
MASTER        0    0    0    0    0    0    0    0   38    0   82    0
END

View in JSmol

Synonyms

Value	Source
3-Ethenyl-1-hydroxy-3,4a,7,7,10a-pentamethyl-10-[(2-methylbut-2-enoyl)oxy]-5-oxo-dodecahydro-1H-naphtho[2,1-b]pyran-8-yl 2,3-dimethyloxirane-2-carboxylic acid	Generator

Chemical Formula

C₃₀H₄₄O₈

Average Mass

532.6740 Da

Monoisotopic Mass

532.30362 Da

IUPAC Name

3-ethenyl-1-hydroxy-3,4a,7,7,10a-pentamethyl-10-[(2-methylbut-2-enoyl)oxy]-5-oxo-dodecahydro-1H-naphtho[2,1-b]pyran-8-yl 2,3-dimethyloxirane-2-carboxylate

Traditional Name

3-ethenyl-1-hydroxy-3,4a,7,7,10a-pentamethyl-10-[(2-methylbut-2-enoyl)oxy]-5-oxo-octahydronaphtho[2,1-b]pyran-8-yl 2,3-dimethyloxirane-2-carboxylate

CAS Registry Number

Not Available

SMILES

CC=C(C)C(=O)OC1CC(OC(=O)C2(C)OC2C)C(C)(C)C2CC(=O)C3(C)OC(C)(CC(O)C3C12C)C=C

InChI Identifier

InChI=1S/C30H44O8/c1-11-16(3)24(33)35-22-14-21(36-25(34)29(9)17(4)37-29)26(5,6)19-13-20(32)30(10)23(28(19,22)8)18(31)15-27(7,12-2)38-30/h11-12,17-19,21-23,31H,2,13-15H2,1,3-10H3

InChI Key

MAMRCICAQFISBT-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

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Triterpenoids

Direct Parent

Triterpenoids

Alternative Parents

Substituents

Triterpenoid
Naphthopyran
Naphthalene
Fatty acid ester
Dicarboxylic acid or derivatives
Fatty acyl
Oxane
Oxirane carboxylic acid
Oxirane carboxylic acid or derivatives
Pyran
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Ketone
Carboxylic acid ester
Secondary alcohol
Organoheterocyclic compound
Oxacycle
Ether
Oxirane
Dialkyl ether
Carboxylic acid derivative
Alcohol
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Carbonyl group
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic 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
logP	4.26	ALOGPS
logP	4.4	ChemAxon
logS	-5.2	ALOGPS
pKa (Strongest Acidic)	14.72	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	111.66 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	140.87 m³·mol⁻¹	ChemAxon
Polarizability	57.81 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	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

162887560

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 3-ethenyl-1-hydroxy-3,4a,7,7,10a-pentamethyl-10-[(2-methylbut-2-enoyl)oxy]-5-oxo-octahydronaphtho[2,1-b]pyran-8-yl 2,3-dimethyloxirane-2-carboxylate (NP0145544)

MOL for NP0145544 (3-ethenyl-1-hydroxy-3,4a,7,7,10a-pentamethyl-10-[(2-methylbut-2-enoyl)oxy]-5-oxo-octahydronaphtho[2,1-b]pyran-8-yl 2,3-dimethyloxirane-2-carboxylate)

3D MOL for NP0145544 (3-ethenyl-1-hydroxy-3,4a,7,7,10a-pentamethyl-10-[(2-methylbut-2-enoyl)oxy]-5-oxo-octahydronaphtho[2,1-b]pyran-8-yl 2,3-dimethyloxirane-2-carboxylate)

3D SDF for NP0145544 (3-ethenyl-1-hydroxy-3,4a,7,7,10a-pentamethyl-10-[(2-methylbut-2-enoyl)oxy]-5-oxo-octahydronaphtho[2,1-b]pyran-8-yl 2,3-dimethyloxirane-2-carboxylate)

3D-SDF for NP0145544 (3-ethenyl-1-hydroxy-3,4a,7,7,10a-pentamethyl-10-[(2-methylbut-2-enoyl)oxy]-5-oxo-octahydronaphtho[2,1-b]pyran-8-yl 2,3-dimethyloxirane-2-carboxylate)

PDB for NP0145544 (3-ethenyl-1-hydroxy-3,4a,7,7,10a-pentamethyl-10-[(2-methylbut-2-enoyl)oxy]-5-oxo-octahydronaphtho[2,1-b]pyran-8-yl 2,3-dimethyloxirane-2-carboxylate)

3D PDB for NP0145544 (3-ethenyl-1-hydroxy-3,4a,7,7,10a-pentamethyl-10-[(2-methylbut-2-enoyl)oxy]-5-oxo-octahydronaphtho[2,1-b]pyran-8-yl 2,3-dimethyloxirane-2-carboxylate)

SMILES for NP0145544 (3-ethenyl-1-hydroxy-3,4a,7,7,10a-pentamethyl-10-[(2-methylbut-2-enoyl)oxy]-5-oxo-octahydronaphtho[2,1-b]pyran-8-yl 2,3-dimethyloxirane-2-carboxylate)

INCHI for NP0145544 (3-ethenyl-1-hydroxy-3,4a,7,7,10a-pentamethyl-10-[(2-methylbut-2-enoyl)oxy]-5-oxo-octahydronaphtho[2,1-b]pyran-8-yl 2,3-dimethyloxirane-2-carboxylate)

Structure for NP0145544 (3-ethenyl-1-hydroxy-3,4a,7,7,10a-pentamethyl-10-[(2-methylbut-2-enoyl)oxy]-5-oxo-octahydronaphtho[2,1-b]pyran-8-yl 2,3-dimethyloxirane-2-carboxylate)

3D Structure for NP0145544 (3-ethenyl-1-hydroxy-3,4a,7,7,10a-pentamethyl-10-[(2-methylbut-2-enoyl)oxy]-5-oxo-octahydronaphtho[2,1-b]pyran-8-yl 2,3-dimethyloxirane-2-carboxylate)