NP-MRD: Showing NP-Card for 5-[7-({2-hydroxy-2-methyl-3-[(2-methylbut-2-enoyl)oxy]butanoyl}oxy)-2,5,5,8a-tetramethyl-1,4,4a,6,7,8-hexahydronaphthalen-1-yl]-3-methylpentanoic acid (NP0165858)

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Record Information

Version

2.0

Created at

2022-09-03 01:06:09 UTC

Updated at

2022-09-03 01:06:10 UTC

NP-MRD ID

NP0165858

Secondary Accession Numbers

None

Natural Product Identification

Common Name

5-[7-({2-hydroxy-2-methyl-3-[(2-methylbut-2-enoyl)oxy]butanoyl}oxy)-2,5,5,8a-tetramethyl-1,4,4a,6,7,8-hexahydronaphthalen-1-yl]-3-methylpentanoic acid

Description

5-[7-({2-Hydroxy-2-methyl-3-[(2-methylbut-2-enoyl)oxy]butanoyl}oxy)-2,5,5,8a-tetramethyl-1,4,4a,5,6,7,8,8a-octahydronaphthalen-1-yl]-3-methylpentanoic acid belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units. 5-[7-({2-hydroxy-2-methyl-3-[(2-methylbut-2-enoyl)oxy]butanoyl}oxy)-2,5,5,8a-tetramethyl-1,4,4a,6,7,8-hexahydronaphthalen-1-yl]-3-methylpentanoic acid is found in Brickellia laciniata. 5-[7-({2-Hydroxy-2-methyl-3-[(2-methylbut-2-enoyl)oxy]butanoyl}oxy)-2,5,5,8a-tetramethyl-1,4,4a,5,6,7,8,8a-octahydronaphthalen-1-yl]-3-methylpentanoic acid is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004261504022D          

 37 38  0  0  0  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1533004261504022D          

 37 38  0  0  0  0            999 V2000
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    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
    1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.8875    0.0000 C   0  0  0  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
    2.1434    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
    3.5724    1.2375    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    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   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
  2  1  1  4  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
 10 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
 18 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 24 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 29 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  2  0  0  0  0
 32 34  1  0  0  0  0
 26 35  1  0  0  0  0
 21 35  1  0  0  0  0
 35 36  1  0  0  0  0
 35 37  1  0  0  0  0
 16 37  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0165858

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC=C(C)C(=O)OC(C)C(C)(O)C(=O)OC1CC(C)(C)C2CC=C(C)C(CCC(C)CC(O)=O)C2(C)C1

> <INCHI_IDENTIFIER>
InChI=1S/C30H48O7/c1-10-19(3)26(33)36-21(5)30(9,35)27(34)37-22-16-28(6,7)24-14-12-20(4)23(29(24,8)17-22)13-11-18(2)15-25(31)32/h10,12,18,21-24,35H,11,13-17H2,1-9H3,(H,31,32)

> <INCHI_KEY>
IEWPUDRMTVALDE-UHFFFAOYSA-N

> <FORMULA>
C30H48O7

> <MOLECULAR_WEIGHT>
520.707

> <EXACT_MASS>
520.340003886

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
85

> <JCHEM_AVERAGE_POLARIZABILITY>
58.98344386965374

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
5-[7-({2-hydroxy-2-methyl-3-[(2-methylbut-2-enoyl)oxy]butanoyl}oxy)-2,5,5,8a-tetramethyl-1,4,4a,5,6,7,8,8a-octahydronaphthalen-1-yl]-3-methylpentanoic acid

> <ALOGPS_LOGP>
5.92

> <JCHEM_LOGP>
6.288776907333333

> <ALOGPS_LOGS>
-5.71

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
11.640298006990594

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.543629339894526

> <JCHEM_PKA_STRONGEST_BASIC>
-4.268333666947595

> <JCHEM_POLAR_SURFACE_AREA>
110.13000000000001

> <JCHEM_REFRACTIVITY>
143.6897

> <JCHEM_ROTATABLE_BOND_COUNT>
12

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.02e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5-[7-({2-hydroxy-2-methyl-3-[(2-methylbut-2-enoyl)oxy]butanoyl}oxy)-2,5,5,8a-tetramethyl-1,4,4a,6,7,8-hexahydronaphthalen-1-yl]-3-methylpentanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 26-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-APR-15         0                                  
HETATM    1  C   UNK     0      -6.668  -8.470   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -5.335  -7.700   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -4.001  -8.470   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -4.001 -10.010   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.667  -7.700   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      -1.334  -8.470   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0      -2.667  -6.160   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000  -6.160   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.334  -3.850   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.206  -3.850   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -2.874  -3.850   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      -2.667  -1.540   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0       0.000  -1.540   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -1.334   0.770   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -2.850   2.043   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -1.860   3.757   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -0.000   3.080   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       1.334   5.390   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       4.001   5.390   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       2.667   3.080   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       5.335   3.080   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       6.668   0.770   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       8.002   3.080   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       9.336   2.310   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      10.669   3.080   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0       9.336   0.770   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       1.334   0.770   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   12   13                                             
CONECT   11   10                                                            
CONECT   12   10                                                            
CONECT   13   10   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15   17   37                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   20   21                                             
CONECT   19   18                                                            
CONECT   20   18                                                            
CONECT   21   18   22   35                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   27   35                                                  
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   32                                                       
CONECT   32   31   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32                                                            
CONECT   35   26   21   36   37                                             
CONECT   36   35                                                            
CONECT   37   35   16                                                       
MASTER        0    0    0    0    0    0    0    0   37    0   76    0
END

View in JSmol

Synonyms

Value	Source
5-[7-({2-hydroxy-2-methyl-3-[(2-methylbut-2-enoyl)oxy]butanoyl}oxy)-2,5,5,8a-tetramethyl-1,4,4a,5,6,7,8,8a-octahydronaphthalen-1-yl]-3-methylpentanoate	Generator

Chemical Formula

C₃₀H₄₈O₇

Average Mass

520.7070 Da

Monoisotopic Mass

520.34000 Da

IUPAC Name

5-[7-({2-hydroxy-2-methyl-3-[(2-methylbut-2-enoyl)oxy]butanoyl}oxy)-2,5,5,8a-tetramethyl-1,4,4a,5,6,7,8,8a-octahydronaphthalen-1-yl]-3-methylpentanoic acid

Traditional Name

5-[7-({2-hydroxy-2-methyl-3-[(2-methylbut-2-enoyl)oxy]butanoyl}oxy)-2,5,5,8a-tetramethyl-1,4,4a,6,7,8-hexahydronaphthalen-1-yl]-3-methylpentanoic acid

CAS Registry Number

Not Available

SMILES

CC=C(C)C(=O)OC(C)C(C)(O)C(=O)OC1CC(C)(C)C2CC=C(C)C(CCC(C)CC(O)=O)C2(C)C1

InChI Identifier

InChI=1S/C30H48O7/c1-10-19(3)26(33)36-21(5)30(9,35)27(34)37-22-16-28(6,7)24-14-12-20(4)23(29(24,8)17-22)13-11-18(2)15-25(31)32/h10,12,18,21-24,35H,11,13-17H2,1-9H3,(H,31,32)

InChI Key

IEWPUDRMTVALDE-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

Species Name	Source	Reference
Brickellia laciniata	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Diterpenoids

Alternative Parents

Substituents

Labdane diterpenoid
Diterpenoid
Tricarboxylic acid or derivatives
Fatty acid ester
Fatty acyl
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Tertiary alcohol
Carboxylic acid ester
Carboxylic acid
Carboxylic acid derivative
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Alcohol
Carbonyl group
Organooxygen compound
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	5.92	ALOGPS
logP	6.29	ChemAxon
logS	-5.7	ALOGPS
pKa (Strongest Acidic)	4.54	ChemAxon
pKa (Strongest Basic)	-4.3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	110.13 Å²	ChemAxon
Rotatable Bond Count	12	ChemAxon
Refractivity	143.69 m³·mol⁻¹	ChemAxon
Polarizability	58.98 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	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

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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 5-[7-({2-hydroxy-2-methyl-3-[(2-methylbut-2-enoyl)oxy]butanoyl}oxy)-2,5,5,8a-tetramethyl-1,4,4a,6,7,8-hexahydronaphthalen-1-yl]-3-methylpentanoic acid (NP0165858)

MOL for NP0165858 (5-[7-({2-hydroxy-2-methyl-3-[(2-methylbut-2-enoyl)oxy]butanoyl}oxy)-2,5,5,8a-tetramethyl-1,4,4a,6,7,8-hexahydronaphthalen-1-yl]-3-methylpentanoic acid)

3D MOL for NP0165858 (5-[7-({2-hydroxy-2-methyl-3-[(2-methylbut-2-enoyl)oxy]butanoyl}oxy)-2,5,5,8a-tetramethyl-1,4,4a,6,7,8-hexahydronaphthalen-1-yl]-3-methylpentanoic acid)

3D SDF for NP0165858 (5-[7-({2-hydroxy-2-methyl-3-[(2-methylbut-2-enoyl)oxy]butanoyl}oxy)-2,5,5,8a-tetramethyl-1,4,4a,6,7,8-hexahydronaphthalen-1-yl]-3-methylpentanoic acid)

3D-SDF for NP0165858 (5-[7-({2-hydroxy-2-methyl-3-[(2-methylbut-2-enoyl)oxy]butanoyl}oxy)-2,5,5,8a-tetramethyl-1,4,4a,6,7,8-hexahydronaphthalen-1-yl]-3-methylpentanoic acid)

PDB for NP0165858 (5-[7-({2-hydroxy-2-methyl-3-[(2-methylbut-2-enoyl)oxy]butanoyl}oxy)-2,5,5,8a-tetramethyl-1,4,4a,6,7,8-hexahydronaphthalen-1-yl]-3-methylpentanoic acid)

3D PDB for NP0165858 (5-[7-({2-hydroxy-2-methyl-3-[(2-methylbut-2-enoyl)oxy]butanoyl}oxy)-2,5,5,8a-tetramethyl-1,4,4a,6,7,8-hexahydronaphthalen-1-yl]-3-methylpentanoic acid)

SMILES for NP0165858 (5-[7-({2-hydroxy-2-methyl-3-[(2-methylbut-2-enoyl)oxy]butanoyl}oxy)-2,5,5,8a-tetramethyl-1,4,4a,6,7,8-hexahydronaphthalen-1-yl]-3-methylpentanoic acid)

INCHI for NP0165858 (5-[7-({2-hydroxy-2-methyl-3-[(2-methylbut-2-enoyl)oxy]butanoyl}oxy)-2,5,5,8a-tetramethyl-1,4,4a,6,7,8-hexahydronaphthalen-1-yl]-3-methylpentanoic acid)

Structure for NP0165858 (5-[7-({2-hydroxy-2-methyl-3-[(2-methylbut-2-enoyl)oxy]butanoyl}oxy)-2,5,5,8a-tetramethyl-1,4,4a,6,7,8-hexahydronaphthalen-1-yl]-3-methylpentanoic acid)

3D Structure for NP0165858 (5-[7-({2-hydroxy-2-methyl-3-[(2-methylbut-2-enoyl)oxy]butanoyl}oxy)-2,5,5,8a-tetramethyl-1,4,4a,6,7,8-hexahydronaphthalen-1-yl]-3-methylpentanoic acid)