NP-MRD: Showing NP-Card for (1r,2s,3r,4s,4as,8ar)-1-(acetyloxy)-4-[(1s)-1-(acetyloxy)-2-(5-oxo-2h-furan-3-yl)ethyl]-3-hydroxy-3,4,8,8a-tetramethyl-2,4a,5,6-tetrahydro-1h-naphthalen-2-yl 2-methylpropanoate (NP0203455)

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Record Information

Version

2.0

Created at

2022-09-04 22:55:02 UTC

Updated at

2022-09-04 22:55:02 UTC

NP-MRD ID

NP0203455

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r,2s,3r,4s,4as,8ar)-1-(acetyloxy)-4-[(1s)-1-(acetyloxy)-2-(5-oxo-2h-furan-3-yl)ethyl]-3-hydroxy-3,4,8,8a-tetramethyl-2,4a,5,6-tetrahydro-1h-naphthalen-2-yl 2-methylpropanoate

Description

Scutolide G belongs to the class of organic compounds known as diterpene lactones. These are diterpenoids containing a lactone moiety. (1r,2s,3r,4s,4as,8ar)-1-(acetyloxy)-4-[(1s)-1-(acetyloxy)-2-(5-oxo-2h-furan-3-yl)ethyl]-3-hydroxy-3,4,8,8a-tetramethyl-2,4a,5,6-tetrahydro-1h-naphthalen-2-yl 2-methylpropanoate is found in Scutellaria barbata. Based on a literature review very few articles have been published on Scutolide G.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309052200552D          

 37 39  0  0  1  0            999 V2000
   -1.3428   -2.9637    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv1652309052200552D          

 37 39  0  0  1  0            999 V2000
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   -0.5122   -6.6967    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8550   -6.2080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1960   -3.7390    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8461   -4.2469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9806   -3.4840    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
  5  4  1  1  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
  7 12  1  0  0  0  0
 13  5  1  6  0  0  0
 13 14  1  1  0  0  0
 13 15  1  0  0  0  0
 15 16  1  1  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 19 21  1  0  0  0  0
 15 21  1  0  0  0  0
 21 22  1  1  0  0  0
 21 23  1  0  0  0  0
 23 24  1  1  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  2  0  0  0  0
 23 28  1  0  0  0  0
 28 29  1  6  0  0  0
 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
 30 32  1  0  0  0  0
 32 33  1  0  0  0  0
 32 34  1  0  0  0  0
 28 35  1  0  0  0  0
 13 35  1  0  0  0  0
 35 36  1  1  0  0  0
 35 37  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0203455

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)C(=O)O[C@H]1[C@H](OC(C)=O)[C@]2(C)[C@H](CCC=C2C)[C@@](C)([C@H](CC2=CC(=O)OC2)OC(C)=O)[C@@]1(C)O

> <INCHI_IDENTIFIER>
InChI=1S/C28H40O9/c1-15(2)25(32)37-24-23(36-18(5)30)26(6)16(3)10-9-11-20(26)27(7,28(24,8)33)21(35-17(4)29)12-19-13-22(31)34-14-19/h10,13,15,20-21,23-24,33H,9,11-12,14H2,1-8H3/t20-,21-,23-,24-,26-,27-,28-/m0/s1

> <INCHI_KEY>
CXZGGRDSOZLEIU-YVSUXUCMSA-N

> <FORMULA>
C28H40O9

> <MOLECULAR_WEIGHT>
520.619

> <EXACT_MASS>
520.267232868

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
77

> <JCHEM_AVERAGE_POLARIZABILITY>
54.71446863086557

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,2S,3R,4S,4aS,8aR)-1-(acetyloxy)-4-[(1S)-1-(acetyloxy)-2-(5-oxo-2,5-dihydrofuran-3-yl)ethyl]-3-hydroxy-3,4,8,8a-tetramethyl-1,2,3,4,4a,5,6,8a-octahydronaphthalen-2-yl 2-methylpropanoate

> <JCHEM_LOGP>
3.143618655666666

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.457081708740649

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.105220427412076

> <JCHEM_PKA_STRONGEST_BASIC>
-3.4737230422108087

> <JCHEM_POLAR_SURFACE_AREA>
125.43000000000002

> <JCHEM_REFRACTIVITY>
133.6217

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2S,3R,4S,4aS,8aR)-1-(acetyloxy)-4-[(1S)-1-(acetyloxy)-2-(5-oxo-2H-furan-3-yl)ethyl]-3-hydroxy-3,4,8,8a-tetramethyl-2,4a,5,6-tetrahydro-1H-naphthalen-2-yl 2-methylpropanoate

> <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  C   UNK     0      -2.506  -5.532   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.506  -3.992   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -3.840  -3.222   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      -1.173  -3.222   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       0.161  -3.992   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.495  -3.222   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.495  -1.682   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.249  -0.777   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.725   0.688   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      -0.181   1.933   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       2.265   0.688   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       2.740  -0.777   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.161  -5.532   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.356  -5.265   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.677  -5.265   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.204  -3.818   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.721  -3.550   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.711  -4.730   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.184  -6.177   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.174  -7.357   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.667  -6.445   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       3.657  -7.624   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       2.141  -7.892   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       3.131  -9.071   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       2.604 -10.519   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       3.594 -11.698   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       1.087 -10.786   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       0.624  -8.159   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       0.097  -9.606   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      -1.419  -9.874   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      -2.409  -8.694   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      -1.946 -11.321   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -0.956 -12.501   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      -3.463 -11.588   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      -0.366  -6.979   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      -1.579  -7.928   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0      -1.830  -6.504   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   13                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   12                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11    7                                                       
CONECT   13    5   14   15   35                                             
CONECT   14   13                                                            
CONECT   15   13   16   21                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   15   22   23                                             
CONECT   22   21                                                            
CONECT   23   21   24   28                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25                                                            
CONECT   28   23   29   35                                                  
CONECT   29   28   30                                                       
CONECT   30   29   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32                                                            
CONECT   35   28   13   36   37                                             
CONECT   36   35                                                            
CONECT   37   35                                                            
MASTER        0    0    0    0    0    0    0    0   37    0   78    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₈H₄₀O₉

Average Mass

520.6190 Da

Monoisotopic Mass

520.26723 Da

IUPAC Name

(1R,2S,3R,4S,4aS,8aR)-1-(acetyloxy)-4-[(1S)-1-(acetyloxy)-2-(5-oxo-2,5-dihydrofuran-3-yl)ethyl]-3-hydroxy-3,4,8,8a-tetramethyl-1,2,3,4,4a,5,6,8a-octahydronaphthalen-2-yl 2-methylpropanoate

Traditional Name

(1R,2S,3R,4S,4aS,8aR)-1-(acetyloxy)-4-[(1S)-1-(acetyloxy)-2-(5-oxo-2H-furan-3-yl)ethyl]-3-hydroxy-3,4,8,8a-tetramethyl-2,4a,5,6-tetrahydro-1H-naphthalen-2-yl 2-methylpropanoate

CAS Registry Number

Not Available

SMILES

CC(C)C(=O)O[C@H]1[C@H](OC(C)=O)[C@]2(C)[C@H](CCC=C2C)[C@@](C)([C@H](CC2=CC(=O)OC2)OC(C)=O)[C@@]1(C)O

InChI Identifier

InChI=1S/C28H40O9/c1-15(2)25(32)37-24-23(36-18(5)30)26(6)16(3)10-9-11-20(26)27(7,28(24,8)33)21(35-17(4)29)12-19-13-22(31)34-14-19/h10,13,15,20-21,23-24,33H,9,11-12,14H2,1-8H3/t20-,21-,23-,24-,26-,27-,28-/m0/s1

InChI Key

CXZGGRDSOZLEIU-YVSUXUCMSA-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
Scutellaria barbata	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as diterpene lactones. These are diterpenoids containing a lactone moiety.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Diterpene lactones

Alternative Parents

Substituents

Diterpene lactone
Clerodane diterpenoid
Diterpenoid
Tetracarboxylic acid or derivatives
Cyclitol or derivatives
2-furanone
Cyclic alcohol
Dihydrofuran
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Tertiary alcohol
Carboxylic acid ester
Lactone
Organoheterocyclic compound
Oxacycle
Carboxylic acid derivative
Hydrocarbon derivative
Alcohol
Carbonyl group
Organic oxide
Organic oxygen compound
Organooxygen compound
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	3.14	ChemAxon
pKa (Strongest Acidic)	7.11	ChemAxon
pKa (Strongest Basic)	-3.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	125.43 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	133.62 m³·mol⁻¹	ChemAxon
Polarizability	54.71 Å³	ChemAxon
Number of Rings	3	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

59004737

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

122177459

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1r,2s,3r,4s,4as,8ar)-1-(acetyloxy)-4-[(1s)-1-(acetyloxy)-2-(5-oxo-2h-furan-3-yl)ethyl]-3-hydroxy-3,4,8,8a-tetramethyl-2,4a,5,6-tetrahydro-1h-naphthalen-2-yl 2-methylpropanoate (NP0203455)

MOL for NP0203455 ((1r,2s,3r,4s,4as,8ar)-1-(acetyloxy)-4-[(1s)-1-(acetyloxy)-2-(5-oxo-2h-furan-3-yl)ethyl]-3-hydroxy-3,4,8,8a-tetramethyl-2,4a,5,6-tetrahydro-1h-naphthalen-2-yl 2-methylpropanoate)

3D MOL for NP0203455 ((1r,2s,3r,4s,4as,8ar)-1-(acetyloxy)-4-[(1s)-1-(acetyloxy)-2-(5-oxo-2h-furan-3-yl)ethyl]-3-hydroxy-3,4,8,8a-tetramethyl-2,4a,5,6-tetrahydro-1h-naphthalen-2-yl 2-methylpropanoate)

3D SDF for NP0203455 ((1r,2s,3r,4s,4as,8ar)-1-(acetyloxy)-4-[(1s)-1-(acetyloxy)-2-(5-oxo-2h-furan-3-yl)ethyl]-3-hydroxy-3,4,8,8a-tetramethyl-2,4a,5,6-tetrahydro-1h-naphthalen-2-yl 2-methylpropanoate)

3D-SDF for NP0203455 ((1r,2s,3r,4s,4as,8ar)-1-(acetyloxy)-4-[(1s)-1-(acetyloxy)-2-(5-oxo-2h-furan-3-yl)ethyl]-3-hydroxy-3,4,8,8a-tetramethyl-2,4a,5,6-tetrahydro-1h-naphthalen-2-yl 2-methylpropanoate)

PDB for NP0203455 ((1r,2s,3r,4s,4as,8ar)-1-(acetyloxy)-4-[(1s)-1-(acetyloxy)-2-(5-oxo-2h-furan-3-yl)ethyl]-3-hydroxy-3,4,8,8a-tetramethyl-2,4a,5,6-tetrahydro-1h-naphthalen-2-yl 2-methylpropanoate)

3D PDB for NP0203455 ((1r,2s,3r,4s,4as,8ar)-1-(acetyloxy)-4-[(1s)-1-(acetyloxy)-2-(5-oxo-2h-furan-3-yl)ethyl]-3-hydroxy-3,4,8,8a-tetramethyl-2,4a,5,6-tetrahydro-1h-naphthalen-2-yl 2-methylpropanoate)

SMILES for NP0203455 ((1r,2s,3r,4s,4as,8ar)-1-(acetyloxy)-4-[(1s)-1-(acetyloxy)-2-(5-oxo-2h-furan-3-yl)ethyl]-3-hydroxy-3,4,8,8a-tetramethyl-2,4a,5,6-tetrahydro-1h-naphthalen-2-yl 2-methylpropanoate)

INCHI for NP0203455 ((1r,2s,3r,4s,4as,8ar)-1-(acetyloxy)-4-[(1s)-1-(acetyloxy)-2-(5-oxo-2h-furan-3-yl)ethyl]-3-hydroxy-3,4,8,8a-tetramethyl-2,4a,5,6-tetrahydro-1h-naphthalen-2-yl 2-methylpropanoate)

Structure for NP0203455 ((1r,2s,3r,4s,4as,8ar)-1-(acetyloxy)-4-[(1s)-1-(acetyloxy)-2-(5-oxo-2h-furan-3-yl)ethyl]-3-hydroxy-3,4,8,8a-tetramethyl-2,4a,5,6-tetrahydro-1h-naphthalen-2-yl 2-methylpropanoate)

3D Structure for NP0203455 ((1r,2s,3r,4s,4as,8ar)-1-(acetyloxy)-4-[(1s)-1-(acetyloxy)-2-(5-oxo-2h-furan-3-yl)ethyl]-3-hydroxy-3,4,8,8a-tetramethyl-2,4a,5,6-tetrahydro-1h-naphthalen-2-yl 2-methylpropanoate)