NP-MRD: Showing NP-Card for 3-[2-hydroxy-7,7-dimethyl-4a,6-bis(3-methylbut-2-en-1-yl)-3-(2-methylbutanoyl)-4-oxo-5,6-dihydrochromen-8-yl]hexanoic acid (NP0185808)

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Record Information

Version

2.0

Created at

2022-09-04 01:22:54 UTC

Updated at

2022-09-04 01:22:54 UTC

NP-MRD ID

NP0185808

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3-[2-hydroxy-7,7-dimethyl-4a,6-bis(3-methylbut-2-en-1-yl)-3-(2-methylbutanoyl)-4-oxo-5,6-dihydrochromen-8-yl]hexanoic acid

Description

3-[2-Hydroxy-7,7-dimethyl-4a,6-bis(3-methylbut-2-en-1-yl)-3-(2-methylbutanoyl)-4-oxo-4a,5,6,7-tetrahydro-4H-chromen-8-yl]hexanoic acid belongs to the class of organic compounds known as bicyclic monoterpenoids. These are monoterpenoids containing exactly 2 rings, which are fused to each other. 3-[2-hydroxy-7,7-dimethyl-4a,6-bis(3-methylbut-2-en-1-yl)-3-(2-methylbutanoyl)-4-oxo-5,6-dihydrochromen-8-yl]hexanoic acid is found in Mahurea palustris. 3-[2-Hydroxy-7,7-dimethyl-4a,6-bis(3-methylbut-2-en-1-yl)-3-(2-methylbutanoyl)-4-oxo-4a,5,6,7-tetrahydro-4H-chromen-8-yl]hexanoic acid is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004261511272D          

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M  END

     RDKit          3D

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M  END


  Mrv1533004261511272D          

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    1.4289   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -7.4250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -7.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -8.2500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -8.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -8.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5390   -5.3337    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1517   -4.6629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  4  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 13 20  1  0  0  0  0
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
 10 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 25 27  1  0  0  0  0
 22 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
 32 33  1  0  0  0  0
 32 34  1  0  0  0  0
 29 35  1  0  0  0  0
  9 35  1  0  0  0  0
 35 36  1  0  0  0  0
 35 37  1  0  0  0  0
 12 38  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0185808

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCC(CC(O)=O)C1=C2OC(O)=C(C(=O)C(C)CC)C(=O)C2(CC=C(C)C)CC(CC=C(C)C)C1(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C32H48O6/c1-10-12-22(17-24(33)34)26-29-32(16-15-20(5)6,18-23(31(26,8)9)14-13-19(3)4)28(36)25(30(37)38-29)27(35)21(7)11-2/h13,15,21-23,37H,10-12,14,16-18H2,1-9H3,(H,33,34)

> <INCHI_KEY>
YCKXZLNJJBVOJD-UHFFFAOYSA-N

> <FORMULA>
C32H48O6

> <MOLECULAR_WEIGHT>
528.73

> <EXACT_MASS>
528.345089266

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
86

> <JCHEM_AVERAGE_POLARIZABILITY>
60.19907781026999

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-[2-hydroxy-7,7-dimethyl-4a,6-bis(3-methylbut-2-en-1-yl)-3-(2-methylbutanoyl)-4-oxo-4a,5,6,7-tetrahydro-4H-chromen-8-yl]hexanoic acid

> <ALOGPS_LOGP>
5.68

> <JCHEM_LOGP>
8.185844416333335

> <ALOGPS_LOGS>
-5.51

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
4.265151162418401

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.3930728921504723

> <JCHEM_PKA_STRONGEST_BASIC>
-5.479436918854639

> <JCHEM_POLAR_SURFACE_AREA>
100.9

> <JCHEM_REFRACTIVITY>
163.604

> <JCHEM_ROTATABLE_BOND_COUNT>
12

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.63e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-[2-hydroxy-7,7-dimethyl-4a,6-bis(3-methylbut-2-en-1-yl)-3-(2-methylbutanoyl)-4-oxo-5,6-dihydrochromen-8-yl]hexanoic 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      -2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.334  -6.930   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000  -7.700   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       0.000  -4.620   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       0.000  -9.240   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.334 -10.010   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       2.667  -9.240   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       4.001 -10.010   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.001 -11.550   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.335 -12.320   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       5.335 -13.860   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       6.668 -11.550   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.668 -10.010   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.002 -12.320   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       9.336 -11.550   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.667 -12.320   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       2.667 -13.860   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       1.334 -11.550   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       1.334 -13.090   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       0.000 -13.860   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       0.000 -15.400   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -1.334 -16.170   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       1.334 -16.170   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       0.000 -12.320   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -1.334 -11.550   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -2.667 -12.320   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -4.001 -11.550   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -5.335 -12.320   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -6.668 -11.550   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      -5.335 -13.860   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      -1.334 -10.010   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      -2.873  -9.956   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      -2.150  -8.704   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0       5.335  -9.240   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5    9                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6                                                            
CONECT    9    4   10   35                                                  
CONECT   10    9   11   22                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   38                                                  
CONECT   13   12   14   20                                                  
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19                                                       
CONECT   19   18                                                            
CONECT   20   13   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   10   23   28                                             
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25                                                            
CONECT   28   22   29                                                       
CONECT   29   28   30   35                                                  
CONECT   30   29   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32                                                            
CONECT   35   29    9   36   37                                             
CONECT   36   35                                                            
CONECT   37   35                                                            
CONECT   38   12                                                            
MASTER        0    0    0    0    0    0    0    0   38    0   78    0
END

View in JSmol

Synonyms

Value	Source
3-[2-Hydroxy-7,7-dimethyl-4a,6-bis(3-methylbut-2-en-1-yl)-3-(2-methylbutanoyl)-4-oxo-4a,5,6,7-tetrahydro-4H-chromen-8-yl]hexanoate	Generator

Chemical Formula

C₃₂H₄₈O₆

Average Mass

528.7300 Da

Monoisotopic Mass

528.34509 Da

IUPAC Name

3-[2-hydroxy-7,7-dimethyl-4a,6-bis(3-methylbut-2-en-1-yl)-3-(2-methylbutanoyl)-4-oxo-4a,5,6,7-tetrahydro-4H-chromen-8-yl]hexanoic acid

Traditional Name

3-[2-hydroxy-7,7-dimethyl-4a,6-bis(3-methylbut-2-en-1-yl)-3-(2-methylbutanoyl)-4-oxo-5,6-dihydrochromen-8-yl]hexanoic acid

CAS Registry Number

Not Available

SMILES

CCCC(CC(O)=O)C1=C2OC(O)=C(C(=O)C(C)CC)C(=O)C2(CC=C(C)C)CC(CC=C(C)C)C1(C)C

InChI Identifier

InChI=1S/C32H48O6/c1-10-12-22(17-24(33)34)26-29-32(16-15-20(5)6,18-23(31(26,8)9)14-13-19(3)4)28(36)25(30(37)38-29)27(35)21(7)11-2/h13,15,21-23,37H,10-12,14,16-18H2,1-9H3,(H,33,34)

InChI Key

YCKXZLNJJBVOJD-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
Mahurea palustris	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as bicyclic monoterpenoids. These are monoterpenoids containing exactly 2 rings, which are fused to each other.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Monoterpenoids

Direct Parent

Bicyclic monoterpenoids

Alternative Parents

Substituents

Bicyclic monoterpenoid
Medium-chain fatty acid
Branched fatty acid
Dihydropyranone
Heterocyclic fatty acid
Hydroxy fatty acid
Fatty acyl
Vinylogous ester
Vinylogous acid
Ketene acetal or derivatives
Ketone
Carboxylic acid derivative
Carboxylic acid
Oxacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Organic oxygen compound
Hydrocarbon derivative
Organic oxide
Carbonyl group
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	5.68	ALOGPS
logP	8.19	ChemAxon
logS	-5.5	ALOGPS
pKa (Strongest Acidic)	2.39	ChemAxon
pKa (Strongest Basic)	-5.5	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	100.9 Å²	ChemAxon
Rotatable Bond Count	12	ChemAxon
Refractivity	163.6 m³·mol⁻¹	ChemAxon
Polarizability	60.2 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

11375975

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 3-[2-hydroxy-7,7-dimethyl-4a,6-bis(3-methylbut-2-en-1-yl)-3-(2-methylbutanoyl)-4-oxo-5,6-dihydrochromen-8-yl]hexanoic acid (NP0185808)

MOL for NP0185808 (3-[2-hydroxy-7,7-dimethyl-4a,6-bis(3-methylbut-2-en-1-yl)-3-(2-methylbutanoyl)-4-oxo-5,6-dihydrochromen-8-yl]hexanoic acid)

3D MOL for NP0185808 (3-[2-hydroxy-7,7-dimethyl-4a,6-bis(3-methylbut-2-en-1-yl)-3-(2-methylbutanoyl)-4-oxo-5,6-dihydrochromen-8-yl]hexanoic acid)

3D SDF for NP0185808 (3-[2-hydroxy-7,7-dimethyl-4a,6-bis(3-methylbut-2-en-1-yl)-3-(2-methylbutanoyl)-4-oxo-5,6-dihydrochromen-8-yl]hexanoic acid)

3D-SDF for NP0185808 (3-[2-hydroxy-7,7-dimethyl-4a,6-bis(3-methylbut-2-en-1-yl)-3-(2-methylbutanoyl)-4-oxo-5,6-dihydrochromen-8-yl]hexanoic acid)

PDB for NP0185808 (3-[2-hydroxy-7,7-dimethyl-4a,6-bis(3-methylbut-2-en-1-yl)-3-(2-methylbutanoyl)-4-oxo-5,6-dihydrochromen-8-yl]hexanoic acid)

3D PDB for NP0185808 (3-[2-hydroxy-7,7-dimethyl-4a,6-bis(3-methylbut-2-en-1-yl)-3-(2-methylbutanoyl)-4-oxo-5,6-dihydrochromen-8-yl]hexanoic acid)

SMILES for NP0185808 (3-[2-hydroxy-7,7-dimethyl-4a,6-bis(3-methylbut-2-en-1-yl)-3-(2-methylbutanoyl)-4-oxo-5,6-dihydrochromen-8-yl]hexanoic acid)

INCHI for NP0185808 (3-[2-hydroxy-7,7-dimethyl-4a,6-bis(3-methylbut-2-en-1-yl)-3-(2-methylbutanoyl)-4-oxo-5,6-dihydrochromen-8-yl]hexanoic acid)

Structure for NP0185808 (3-[2-hydroxy-7,7-dimethyl-4a,6-bis(3-methylbut-2-en-1-yl)-3-(2-methylbutanoyl)-4-oxo-5,6-dihydrochromen-8-yl]hexanoic acid)

3D Structure for NP0185808 (3-[2-hydroxy-7,7-dimethyl-4a,6-bis(3-methylbut-2-en-1-yl)-3-(2-methylbutanoyl)-4-oxo-5,6-dihydrochromen-8-yl]hexanoic acid)