NP-MRD: Showing NP-Card for (4r,6s,6ar,9s)-3,6,9-trimethyl-4-(2-methylprop-1-en-1-yl)-2-{[(2r,3s,4r,5s)-3,4,5-trihydroxyoxan-2-yl]oxy}-5,6,6a,7,8,9-hexahydro-4h-phenalen-1-yl acetate (NP0158218)

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Record Information

Version

2.0

Created at

2022-09-02 15:46:15 UTC

Updated at

2022-09-02 15:46:15 UTC

NP-MRD ID

NP0158218

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(4r,6s,6ar,9s)-3,6,9-trimethyl-4-(2-methylprop-1-en-1-yl)-2-{[(2r,3s,4r,5s)-3,4,5-trihydroxyoxan-2-yl]oxy}-5,6,6a,7,8,9-hexahydro-4h-phenalen-1-yl acetate

Description

(3S,7R,9S,9aR)-3,6,9-trimethyl-7-(2-methylprop-1-en-1-yl)-5-{[(2R,3S,4R,5S)-3,4,5-trihydroxyoxan-2-yl]oxy}-2,3,7,8,9,9a-hexahydro-1H-phenalen-4-yl acetate belongs to the class of organic compounds known as amphilectane, neoamphilectane, cycloamphilectane, and adociane diterpenoids. These are diterpenoids with a structure based on the amphilectane or a seco-,neo-, or cyclo- derivative thereof. Amphilectane is a tricyclic structure made up of three cyclohexane fused together, with a methyl group at the C11-, C7-, and C3- positions. Additionally, it carries a 2-methylpropyl group at the C1-position. Amphilectanes are presumably derived from serrulatanes. Cycloamphilectanes represent a further cyclisation. (4r,6s,6ar,9s)-3,6,9-trimethyl-4-(2-methylprop-1-en-1-yl)-2-{[(2r,3s,4r,5s)-3,4,5-trihydroxyoxan-2-yl]oxy}-5,6,6a,7,8,9-hexahydro-4h-phenalen-1-yl acetate is found in Antillogorgia elisabethae. Based on a literature review very few articles have been published on (3S,7R,9S,9aR)-3,6,9-trimethyl-7-(2-methylprop-1-en-1-yl)-5-{[(2R,3S,4R,5S)-3,4,5-trihydroxyoxan-2-yl]oxy}-2,3,7,8,9,9a-hexahydro-1H-phenalen-4-yl acetate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309022217462D          

 34 37  0  0  1  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652309022217462D          

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  8  7  1  1  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  6  0  0  0
 11 13  1  0  0  0  0
 13 14  1  1  0  0  0
 13 15  1  0  0  0  0
  8 15  1  0  0  0  0
 15 16  1  6  0  0  0
  6 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
  5 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  1  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
 26 25  1  6  0  0  0
 20 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  1  0  0  0
 27 29  1  0  0  0  0
 29 30  1  0  0  0  0
 19 30  1  0  0  0  0
 30 31  1  6  0  0  0
 31 32  2  0  0  0  0
 32 33  1  0  0  0  0
 32 34  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0158218

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@H]1C[C@H](C=C(C)C)C2=C(C)C(O[C@H]3OC[C@H](O)[C@@H](O)[C@@H]3O)=C(OC(C)=O)C3=C2[C@@H]1CC[C@@H]3C

> <INCHI_IDENTIFIER>
InChI=1S/C27H38O7/c1-12(2)9-17-10-14(4)18-8-7-13(3)20-22(18)21(17)15(5)25(26(20)33-16(6)28)34-27-24(31)23(30)19(29)11-32-27/h9,13-14,17-19,23-24,27,29-31H,7-8,10-11H2,1-6H3/t13-,14-,17-,18+,19-,23+,24-,27+/m0/s1

> <INCHI_KEY>
CFEIHTABPZLNQZ-AHVPAXKDSA-N

> <FORMULA>
C27H38O7

> <MOLECULAR_WEIGHT>
474.594

> <EXACT_MASS>
474.261753564

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
72

> <JCHEM_AVERAGE_POLARIZABILITY>
51.851485198112925

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(3S,7R,9S,9aR)-3,6,9-trimethyl-7-(2-methylprop-1-en-1-yl)-5-{[(2R,3S,4R,5S)-3,4,5-trihydroxyoxan-2-yl]oxy}-2,3,7,8,9,9a-hexahydro-1H-phenalen-4-yl acetate

> <ALOGPS_LOGP>
3.31

> <JCHEM_LOGP>
4.0178013946666695

> <ALOGPS_LOGS>
-4.35

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.399709261975563

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.234869098485062

> <JCHEM_PKA_STRONGEST_BASIC>
-3.526598526061237

> <JCHEM_POLAR_SURFACE_AREA>
105.45000000000002

> <JCHEM_REFRACTIVITY>
128.51159999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.12e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(4R,6S,6aR,9S)-3,6,9-trimethyl-4-(2-methylprop-1-en-1-yl)-2-{[(2R,3S,4R,5S)-3,4,5-trihydroxyoxan-2-yl]oxy}-5,6,6a,7,8,9-hexahydro-4H-phenalen-1-yl acetate

> <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      -5.335   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -4.001  -2.310   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      -2.667   0.000   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -2.667  -3.080   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -1.334  -5.390   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      -1.334  -6.930   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -2.667  -7.700   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -2.667  -9.240   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      -4.001  -6.930   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      -5.335  -7.700   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      -4.001  -5.390   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -5.335  -4.620   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6   21                                                  
CONECT    6    5    7   17                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   15                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13    8   16                                                  
CONECT   16   15                                                            
CONECT   17    6   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20   30                                                  
CONECT   20   19   21   26                                                  
CONECT   21   20    5   22                                                  
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   20   27                                                  
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30                                                       
CONECT   30   29   19   31                                                  
CONECT   31   30   32                                                       
CONECT   32   31   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   74    0
END

View in JSmol

Synonyms

Value	Source
(3S,7R,9S,9AR)-3,6,9-trimethyl-7-(2-methylprop-1-en-1-yl)-5-{[(2R,3S,4R,5S)-3,4,5-trihydroxyoxan-2-yl]oxy}-2,3,7,8,9,9a-hexahydro-1H-phenalen-4-yl acetic acid	Generator

Chemical Formula

C₂₇H₃₈O₇

Average Mass

474.5940 Da

Monoisotopic Mass

474.26175 Da

IUPAC Name

(3S,7R,9S,9aR)-3,6,9-trimethyl-7-(2-methylprop-1-en-1-yl)-5-{[(2R,3S,4R,5S)-3,4,5-trihydroxyoxan-2-yl]oxy}-2,3,7,8,9,9a-hexahydro-1H-phenalen-4-yl acetate

Traditional Name

(4R,6S,6aR,9S)-3,6,9-trimethyl-4-(2-methylprop-1-en-1-yl)-2-{[(2R,3S,4R,5S)-3,4,5-trihydroxyoxan-2-yl]oxy}-5,6,6a,7,8,9-hexahydro-4H-phenalen-1-yl acetate

CAS Registry Number

Not Available

SMILES

C[C@H]1C[C@H](C=C(C)C)C2=C(C)C(O[C@H]3OC[C@H](O)[C@@H](O)[C@@H]3O)=C(OC(C)=O)C3=C2[C@@H]1CC[C@@H]3C

InChI Identifier

InChI=1S/C27H38O7/c1-12(2)9-17-10-14(4)18-8-7-13(3)20-22(18)21(17)15(5)25(26(20)33-16(6)28)34-27-24(31)23(30)19(29)11-32-27/h9,13-14,17-19,23-24,27,29-31H,7-8,10-11H2,1-6H3/t13-,14-,17-,18+,19-,23+,24-,27+/m0/s1

InChI Key

CFEIHTABPZLNQZ-AHVPAXKDSA-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
Antillogorgia elisabethae	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as amphilectane, neoamphilectane, cycloamphilectane, and adociane diterpenoids. These are diterpenoids with a structure based on the amphilectane or a seco-,neo-, or cyclo- derivative thereof. Amphilectane is a tricyclic structure made up of three cyclohexane fused together, with a methyl group at the C11-, C7-, and C3- positions. Additionally, it carries a 2-methylpropyl group at the C1-position. Amphilectanes are presumably derived from serrulatanes. Cycloamphilectanes represent a further cyclisation.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Amphilectane, neoamphilectane, cycloamphilectane, and adociane diterpenoids

Alternative Parents

Substituents

Amphilectane, neoamphilectane, cycloamphilectane, or adociane diterpenoid
Phenolic glycoside
Glycosyl compound
O-glycosyl compound
Tetralin
Monosaccharide
Oxane
Benzenoid
Secondary alcohol
Carboxylic acid ester
Polyol
Acetal
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Oxacycle
Organoheterocyclic compound
Hydrocarbon derivative
Alcohol
Organooxygen compound
Organic oxide
Organic oxygen compound
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
logP	3.31	ALOGPS
logP	4.02	ChemAxon
logS	-4.4	ALOGPS
pKa (Strongest Acidic)	12.23	ChemAxon
pKa (Strongest Basic)	-3.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	105.45 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	128.51 m³·mol⁻¹	ChemAxon
Polarizability	51.85 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	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

9469437

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11294452

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (4r,6s,6ar,9s)-3,6,9-trimethyl-4-(2-methylprop-1-en-1-yl)-2-{[(2r,3s,4r,5s)-3,4,5-trihydroxyoxan-2-yl]oxy}-5,6,6a,7,8,9-hexahydro-4h-phenalen-1-yl acetate (NP0158218)

MOL for NP0158218 ((4r,6s,6ar,9s)-3,6,9-trimethyl-4-(2-methylprop-1-en-1-yl)-2-{[(2r,3s,4r,5s)-3,4,5-trihydroxyoxan-2-yl]oxy}-5,6,6a,7,8,9-hexahydro-4h-phenalen-1-yl acetate)

3D MOL for NP0158218 ((4r,6s,6ar,9s)-3,6,9-trimethyl-4-(2-methylprop-1-en-1-yl)-2-{[(2r,3s,4r,5s)-3,4,5-trihydroxyoxan-2-yl]oxy}-5,6,6a,7,8,9-hexahydro-4h-phenalen-1-yl acetate)

3D SDF for NP0158218 ((4r,6s,6ar,9s)-3,6,9-trimethyl-4-(2-methylprop-1-en-1-yl)-2-{[(2r,3s,4r,5s)-3,4,5-trihydroxyoxan-2-yl]oxy}-5,6,6a,7,8,9-hexahydro-4h-phenalen-1-yl acetate)

3D-SDF for NP0158218 ((4r,6s,6ar,9s)-3,6,9-trimethyl-4-(2-methylprop-1-en-1-yl)-2-{[(2r,3s,4r,5s)-3,4,5-trihydroxyoxan-2-yl]oxy}-5,6,6a,7,8,9-hexahydro-4h-phenalen-1-yl acetate)

PDB for NP0158218 ((4r,6s,6ar,9s)-3,6,9-trimethyl-4-(2-methylprop-1-en-1-yl)-2-{[(2r,3s,4r,5s)-3,4,5-trihydroxyoxan-2-yl]oxy}-5,6,6a,7,8,9-hexahydro-4h-phenalen-1-yl acetate)

3D PDB for NP0158218 ((4r,6s,6ar,9s)-3,6,9-trimethyl-4-(2-methylprop-1-en-1-yl)-2-{[(2r,3s,4r,5s)-3,4,5-trihydroxyoxan-2-yl]oxy}-5,6,6a,7,8,9-hexahydro-4h-phenalen-1-yl acetate)

SMILES for NP0158218 ((4r,6s,6ar,9s)-3,6,9-trimethyl-4-(2-methylprop-1-en-1-yl)-2-{[(2r,3s,4r,5s)-3,4,5-trihydroxyoxan-2-yl]oxy}-5,6,6a,7,8,9-hexahydro-4h-phenalen-1-yl acetate)

INCHI for NP0158218 ((4r,6s,6ar,9s)-3,6,9-trimethyl-4-(2-methylprop-1-en-1-yl)-2-{[(2r,3s,4r,5s)-3,4,5-trihydroxyoxan-2-yl]oxy}-5,6,6a,7,8,9-hexahydro-4h-phenalen-1-yl acetate)

Structure for NP0158218 ((4r,6s,6ar,9s)-3,6,9-trimethyl-4-(2-methylprop-1-en-1-yl)-2-{[(2r,3s,4r,5s)-3,4,5-trihydroxyoxan-2-yl]oxy}-5,6,6a,7,8,9-hexahydro-4h-phenalen-1-yl acetate)

3D Structure for NP0158218 ((4r,6s,6ar,9s)-3,6,9-trimethyl-4-(2-methylprop-1-en-1-yl)-2-{[(2r,3s,4r,5s)-3,4,5-trihydroxyoxan-2-yl]oxy}-5,6,6a,7,8,9-hexahydro-4h-phenalen-1-yl acetate)