NP-MRD: Showing NP-Card for (4as,6r,8ar)-6-hydroxy-4,8a-dimethyl-6-(prop-1-en-2-yl)-4a,5,7,8-tetrahydro-1h-naphthalen-2-one (NP0157377)

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Record Information

Version

2.0

Created at

2022-09-02 14:45:01 UTC

Updated at

2022-09-02 14:45:01 UTC

NP-MRD ID

NP0157377

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(4as,6r,8ar)-6-hydroxy-4,8a-dimethyl-6-(prop-1-en-2-yl)-4a,5,7,8-tetrahydro-1h-naphthalen-2-one

Description

TEUCRENONE belongs to the class of organic compounds known as eudesmane, isoeudesmane or cycloeudesmane sesquiterpenoids. These are sesquiterpenoids with a structure based on the eudesmane skeleton. (4as,6r,8ar)-6-hydroxy-4,8a-dimethyl-6-(prop-1-en-2-yl)-4a,5,7,8-tetrahydro-1h-naphthalen-2-one is found in Alpinia oxyphylla, Dictyophora indusiata and Teucrium heterophyllum. (4as,6r,8ar)-6-hydroxy-4,8a-dimethyl-6-(prop-1-en-2-yl)-4a,5,7,8-tetrahydro-1h-naphthalen-2-one was first documented in 2021 (PMID: 33334283). Based on a literature review very few articles have been published on TEUCRENONE.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 39 40  0  0  0  0  0  0  0  0999 V2000
    3.8663    0.7692   -0.8676 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8702    0.4141   -0.0629 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0613    0.5142    1.4202 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5828   -0.0761   -0.6264 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7033   -0.1268   -2.0130 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2851   -1.4795   -0.1567 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0088   -1.8981   -0.8239 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0950   -1.0267   -0.2197 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.2040   -1.3472    1.2301 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4356   -1.3948   -0.8670 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4626   -0.6167   -0.1342 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6115   -1.0558    0.0700 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1119    0.7126    0.3653 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9021    1.2181    0.1945 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6216    2.5639    0.7251 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8757    0.4305   -0.5160 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5149    0.9060   -0.2387 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8082    1.1273   -0.4910 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7341    0.6993   -1.9286 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1200    0.6716    1.6415 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7645   -0.4793    1.8607 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4687    1.3487    1.8447 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4346    0.7280   -2.4453 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1219   -2.1232   -0.4947 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2176   -1.5606    0.9355 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2402   -2.9474   -0.6153 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0691   -1.6857   -1.9123 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9582   -2.4385    1.3497 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2148   -1.2196    1.6577 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5013   -0.7764    1.8699 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3915   -1.0449   -1.9043 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6203   -2.4866   -0.7771 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8853    1.2633    0.8801 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3510    2.7960    1.5559 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6180    2.7046    1.1303 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8195    3.3531   -0.0510 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0713    0.5649   -1.6151 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6690    1.1583    0.8352 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7086    1.8404   -0.8054 H   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  1  0
  2  1  2  3
  2  4  1  0
  4  5  1  6
  4  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  1
  8 10  1  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  2  0
 14 15  1  0
 14 16  1  0
 16 17  1  0
 17  4  1  0
 16  8  1  0
  3 20  1  0
  3 21  1  0
  3 22  1  0
  1 18  1  0
  1 19  1  0
  5 23  1  0
  6 24  1  0
  6 25  1  0
  7 26  1  0
  7 27  1  0
  9 28  1  0
  9 29  1  0
  9 30  1  0
 10 31  1  0
 10 32  1  0
 13 33  1  0
 15 34  1  0
 15 35  1  0
 15 36  1  0
 16 37  1  6
 17 38  1  0
 17 39  1  0
M  END

  Mrv1652309022216452D          

 17 18  0  0  1  0            999 V2000
   -0.3802   -0.3190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0980   -1.0942    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6283   -1.7262    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4323   -2.0127    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1434    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    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
  4  2  1  1  0  0  0
  4  5  1  6  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  1  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 16 14  1  1  0  0  0
  8 16  1  0  0  0  0
 16 17  1  0  0  0  0
  4 17  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0157377

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C15H22O2/c1-10(2)15(17)6-5-14(4)8-12(16)7-11(3)13(14)9-15/h7,13,17H,1,5-6,8-9H2,2-4H3/t13-,14-,15-/m1/s1

> <INCHI_KEY>
SAJFRLDIWQUNCQ-RBSFLKMASA-N

> <FORMULA>
C15H22O2

> <MOLECULAR_WEIGHT>
234.339

> <EXACT_MASS>
234.161979948

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
39

> <JCHEM_AVERAGE_POLARIZABILITY>
26.953517331237215

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(4aS,6R,8aR)-6-hydroxy-4,8a-dimethyl-6-(prop-1-en-2-yl)-1,2,4a,5,6,7,8,8a-octahydronaphthalen-2-one

> <ALOGPS_LOGP>
2.32

> <JCHEM_LOGP>
2.540537047666667

> <ALOGPS_LOGS>
-2.98

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
19.577692472749764

> <JCHEM_PKA_STRONGEST_ACIDIC>
18.806408216182625

> <JCHEM_PKA_STRONGEST_BASIC>
-0.796458525917625

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
69.59859999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.44e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(4aS,6R,8aR)-6-hydroxy-4,8a-dimethyl-6-(prop-1-en-2-yl)-4a,5,7,8-tetrahydro-1H-naphthalen-2-one

> <JCHEM_VEBER_RULE>
1

$$$$

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      -0.710  -0.595   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.183  -2.043   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.173  -3.222   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       0.807  -3.757   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.001   0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       8.002  -0.000   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5    6   17                                             
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   10   16                                             
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14    8   17                                                  
CONECT   17   16    4                                                       
MASTER        0    0    0    0    0    0    0    0   17    0   36    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₅H₂₂O₂

Average Mass

234.3390 Da

Monoisotopic Mass

234.16198 Da

IUPAC Name

(4aS,6R,8aR)-6-hydroxy-4,8a-dimethyl-6-(prop-1-en-2-yl)-1,2,4a,5,6,7,8,8a-octahydronaphthalen-2-one

Traditional Name

(4aS,6R,8aR)-6-hydroxy-4,8a-dimethyl-6-(prop-1-en-2-yl)-4a,5,7,8-tetrahydro-1H-naphthalen-2-one

CAS Registry Number

Not Available

SMILES

CC(=C)[C@@]1(O)CC[C@]2(C)CC(=O)C=C(C)[C@H]2C1

InChI Identifier

InChI=1S/C15H22O2/c1-10(2)15(17)6-5-14(4)8-12(16)7-11(3)13(14)9-15/h7,13,17H,1,5-6,8-9H2,2-4H3/t13-,14-,15-/m1/s1

InChI Key

SAJFRLDIWQUNCQ-RBSFLKMASA-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
Alpinia oxyphylla	LOTUS Database	35616633
Dictyophora indusiata	LOTUS Database	35616633
Teucrium heterophyllum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as eudesmane, isoeudesmane or cycloeudesmane sesquiterpenoids. These are sesquiterpenoids with a structure based on the eudesmane skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Eudesmane, isoeudesmane or cycloeudesmane sesquiterpenoids

Alternative Parents

Substituents

Eudesmane, isoeudesmane or cycloeudesmane sesquiterpenoid
Cyclohexenone
Tertiary alcohol
Cyclic alcohol
Cyclic ketone
Ketone
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic 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	2.32	ALOGPS
logP	2.54	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	18.81	ChemAxon
pKa (Strongest Basic)	-0.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	37.3 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	69.6 m³·mol⁻¹	ChemAxon
Polarizability	26.95 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	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

8280970

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10105443

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Zuo L, Li J, Xue L, Jia Q, Li Z, Zhang M, Zhao M, Wang M, Kang J, Du S, Sun Z: Integrated UPLC-MS/MS and UHPLC-Q-orbitrap HRMS Analysis to Reveal Pharmacokinetics and Metabolism of Five Terpenoids from Alpiniae oxyphyllae Fructus in Rats. Curr Drug Metab. 2021;22(1):70-82. doi: 10.2174/1389200221666201217154219. [PubMed:33334283 ]
LOTUS database [Link]

Showing NP-Card for (4as,6r,8ar)-6-hydroxy-4,8a-dimethyl-6-(prop-1-en-2-yl)-4a,5,7,8-tetrahydro-1h-naphthalen-2-one (NP0157377)

MOL for NP0157377 ((4as,6r,8ar)-6-hydroxy-4,8a-dimethyl-6-(prop-1-en-2-yl)-4a,5,7,8-tetrahydro-1h-naphthalen-2-one)

3D MOL for NP0157377 ((4as,6r,8ar)-6-hydroxy-4,8a-dimethyl-6-(prop-1-en-2-yl)-4a,5,7,8-tetrahydro-1h-naphthalen-2-one)

3D SDF for NP0157377 ((4as,6r,8ar)-6-hydroxy-4,8a-dimethyl-6-(prop-1-en-2-yl)-4a,5,7,8-tetrahydro-1h-naphthalen-2-one)

3D-SDF for NP0157377 ((4as,6r,8ar)-6-hydroxy-4,8a-dimethyl-6-(prop-1-en-2-yl)-4a,5,7,8-tetrahydro-1h-naphthalen-2-one)

PDB for NP0157377 ((4as,6r,8ar)-6-hydroxy-4,8a-dimethyl-6-(prop-1-en-2-yl)-4a,5,7,8-tetrahydro-1h-naphthalen-2-one)

3D PDB for NP0157377 ((4as,6r,8ar)-6-hydroxy-4,8a-dimethyl-6-(prop-1-en-2-yl)-4a,5,7,8-tetrahydro-1h-naphthalen-2-one)

SMILES for NP0157377 ((4as,6r,8ar)-6-hydroxy-4,8a-dimethyl-6-(prop-1-en-2-yl)-4a,5,7,8-tetrahydro-1h-naphthalen-2-one)

INCHI for NP0157377 ((4as,6r,8ar)-6-hydroxy-4,8a-dimethyl-6-(prop-1-en-2-yl)-4a,5,7,8-tetrahydro-1h-naphthalen-2-one)

Structure for NP0157377 ((4as,6r,8ar)-6-hydroxy-4,8a-dimethyl-6-(prop-1-en-2-yl)-4a,5,7,8-tetrahydro-1h-naphthalen-2-one)

3D Structure for NP0157377 ((4as,6r,8ar)-6-hydroxy-4,8a-dimethyl-6-(prop-1-en-2-yl)-4a,5,7,8-tetrahydro-1h-naphthalen-2-one)