NP-MRD: Showing NP-Card for [2R-(2alpha,4aalpha,8beta,8abeta)]-Decahydro-8-[2-hydroxy-4-(2-propenyl)-6-[4-(2-propenyl)phenoxy]phenoxy]-alpha,alpha,4a,8-tetramethyl-2-naphthalenemethanol (NP0059293)

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Record Information

Version

2.0

Created at

2022-04-28 04:33:40 UTC

Updated at

2022-04-28 04:33:40 UTC

NP-MRD ID

NP0059293

Secondary Accession Numbers

None

Natural Product Identification

Common Name

[2R-(2alpha,4aalpha,8beta,8abeta)]-Decahydro-8-[2-hydroxy-4-(2-propenyl)-6-[4-(2-propenyl)phenoxy]phenoxy]-alpha,alpha,4a,8-tetramethyl-2-naphthalenemethanol

Description

Eudesobovatol B 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. [2R-(2alpha,4aalpha,8beta,8abeta)]-Decahydro-8-[2-hydroxy-4-(2-propenyl)-6-[4-(2-propenyl)phenoxy]phenoxy]-alpha,alpha,4a,8-tetramethyl-2-naphthalenemethanol is found in Magnolia obovata . [2R-(2alpha,4aalpha,8beta,8abeta)]-Decahydro-8-[2-hydroxy-4-(2-propenyl)-6-[4-(2-propenyl)phenoxy]phenoxy]-alpha,alpha,4a,8-tetramethyl-2-naphthalenemethanol was first documented in 2016 (PMID: 26609630). Based on a literature review very few articles have been published on Eudesobovatol B.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282206332D          

 37 40  0  0  1  0            999 V2000
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  2 37  1  6  0  0  0
M  END

     RDKit          3D

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M  END


  Mrv1652304282206332D          

 37 40  0  0  1  0            999 V2000
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   -2.6231    4.1978    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3873    0.7284    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  1  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
    1.4289   -1.6500    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 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2704   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4454    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.0625    0.0000 C   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
  1  6  1  0  0  0  0
  4  7  1  1  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 11 16  1  0  0  0  0
 14 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
  9 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
  8 23  1  0  0  0  0
 23 24  1  0  0  0  0
 21 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
  4 28  1  6  0  0  0
  3 29  1  6  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
  2 32  1  0  0  0  0
 30 33  1  6  0  0  0
 33 34  1  0  0  0  0
 33 35  1  0  0  0  0
 33 36  1  0  0  0  0
  2 37  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0059293

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)(O)[C@@H]1CC[C@@]2(C)CCC[C@@](C)(OC3=C(OC4=CC=C(CC=C)C=C4)C=C(CC=C)C=C3O)[C@@H]2C1

> <INCHI_IDENTIFIER>
InChI=1S/C33H44O4/c1-7-10-23-12-14-26(15-13-23)36-28-21-24(11-8-2)20-27(34)30(28)37-33(6)18-9-17-32(5)19-16-25(22-29(32)33)31(3,4)35/h7-8,12-15,20-21,25,29,34-35H,1-2,9-11,16-19,22H2,3-6H3/t25-,29-,32-,33-/m1/s1

> <INCHI_KEY>
AGBYBGPUAJZWDY-CLRSYFRZSA-N

> <FORMULA>
C33H44O4

> <MOLECULAR_WEIGHT>
504.711

> <EXACT_MASS>
504.323959897

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
81

> <JCHEM_AVERAGE_POLARIZABILITY>
58.90534905042739

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-{[(1R,4aR,7R,8aR)-7-(2-hydroxypropan-2-yl)-1,4a-dimethyl-decahydronaphthalen-1-yl]oxy}-5-(prop-2-en-1-yl)-3-[4-(prop-2-en-1-yl)phenoxy]phenol

> <ALOGPS_LOGP>
8.15

> <JCHEM_LOGP>
8.292181450333334

> <ALOGPS_LOGS>
-6.75

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
19.24783916817395

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.494794628842119

> <JCHEM_PKA_STRONGEST_BASIC>
-0.9400681856780592

> <JCHEM_POLAR_SURFACE_AREA>
58.92

> <JCHEM_REFRACTIVITY>
151.32230000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
8.98e-05 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-{[(1R,4aR,7R,8aR)-7-(2-hydroxypropan-2-yl)-1,4a-dimethyl-octahydronaphthalen-1-yl]oxy}-5-(prop-2-en-1-yl)-3-[4-(prop-2-en-1-yl)phenoxy]phenol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0      -0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+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       0.723   1.360   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -0.093   2.666   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.632   2.612   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      -2.355   1.252   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      -3.894   1.199   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -4.617  -0.161   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -6.156  -0.215   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -6.972   1.091   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -6.249   2.451   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -4.710   2.504   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -8.511   1.037   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -9.327   2.343   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0     -10.867   2.290   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -2.448   3.918   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -1.725   5.278   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -0.186   5.331   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       0.630   4.025   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       2.169   4.079   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      -2.541   6.584   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -4.080   6.530   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -4.896   7.836   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -0.723   1.360   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       5.335  -0.000   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       6.668   0.770   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0       6.105  -1.334   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       4.565   1.334   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       1.334  -3.850   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3   32   37                                             
CONECT    3    2    4   29                                                  
CONECT    4    3    5    7   28                                             
CONECT    5    4    6                                                       
CONECT    6    5    1                                                       
CONECT    7    4    8                                                       
CONECT    8    7    9   23                                                  
CONECT    9    8   10   20                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   16                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   17                                                  
CONECT   15   14   16                                                       
CONECT   16   15   11                                                       
CONECT   17   14   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18                                                            
CONECT   20    9   21                                                       
CONECT   21   20   22   25                                                  
CONECT   22   21   23                                                       
CONECT   23   22    8   24                                                  
CONECT   24   23                                                            
CONECT   25   21   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26                                                            
CONECT   28    4                                                            
CONECT   29    3   30                                                       
CONECT   30   29   31   33                                                  
CONECT   31   30   32                                                       
CONECT   32   31    2                                                       
CONECT   33   30   34   35   36                                             
CONECT   34   33                                                            
CONECT   35   33                                                            
CONECT   36   33                                                            
CONECT   37    2                                                            
MASTER        0    0    0    0    0    0    0    0   37    0   80    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₃H₄₄O₄

Average Mass

504.7110 Da

Monoisotopic Mass

504.32396 Da

IUPAC Name

2-{[(1R,4aR,7R,8aR)-7-(2-hydroxypropan-2-yl)-1,4a-dimethyl-decahydronaphthalen-1-yl]oxy}-5-(prop-2-en-1-yl)-3-[4-(prop-2-en-1-yl)phenoxy]phenol

Traditional Name

2-{[(1R,4aR,7R,8aR)-7-(2-hydroxypropan-2-yl)-1,4a-dimethyl-octahydronaphthalen-1-yl]oxy}-5-(prop-2-en-1-yl)-3-[4-(prop-2-en-1-yl)phenoxy]phenol

CAS Registry Number

Not Available

SMILES

CC(C)(O)[C@@H]1CC[C@@]2(C)CCC[C@@](C)(OC3=C(OC4=CC=C(CC=C)C=C4)C=C(CC=C)C=C3O)[C@@H]2C1

InChI Identifier

InChI=1S/C33H44O4/c1-7-10-23-12-14-26(15-13-23)36-28-21-24(11-8-2)20-27(34)30(28)37-33(6)18-9-17-32(5)19-16-25(22-29(32)33)31(3,4)35/h7-8,12-15,20-21,25,29,34-35H,1-2,9-11,16-19,22H2,3-6H3/t25-,29-,32-,33-/m1/s1

InChI Key

AGBYBGPUAJZWDY-CLRSYFRZSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Magnolia obovata	Plant	KNApSAcK

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
Diphenylether
Diaryl ether
Phenol ether
Phenoxy compound
1-hydroxy-4-unsubstituted benzenoid
Phenol
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
Benzenoid
Monocyclic benzene moiety
Tertiary alcohol
Ether
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Alcohol
Aromatic homopolycyclic compound

Molecular Framework

Aromatic 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	8.15	ALOGPS
logP	8.29	ChemAxon
logS	-6.8	ALOGPS
pKa (Strongest Acidic)	9.49	ChemAxon
pKa (Strongest Basic)	-0.94	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	58.92 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	151.32 m³·mol⁻¹	ChemAxon
Polarizability	58.91 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	No	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

C00012820

Chemspider ID

8521489

KEGG Compound ID

C17677

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10346031

PDB ID

Not Available

ChEBI ID

182022

Good Scents ID

Not Available

References

General References

Hu X, Sui X, Wang Y, Wang W, Wu H, Zhang F, Tan Y, Zhang F: Sesquiterpene-neolignans from Manglietia hookeri. Nat Prod Res. 2016 Jul;30(13):1477-83. doi: 10.1080/14786419.2015.1110703. Epub 2015 Nov 26. [PubMed:26609630 ]

Showing NP-Card for [2R-(2alpha,4aalpha,8beta,8abeta)]-Decahydro-8-[2-hydroxy-4-(2-propenyl)-6-[4-(2-propenyl)phenoxy]phenoxy]-alpha,alpha,4a,8-tetramethyl-2-naphthalenemethanol (NP0059293)

MOL for NP0059293 ([2R-(2alpha,4aalpha,8beta,8abeta)]-Decahydro-8-[2-hydroxy-4-(2-propenyl)-6-[4-(2-propenyl)phenoxy]phenoxy]-alpha,alpha,4a,8-tetramethyl-2-naphthalenemethanol)

3D MOL for NP0059293 ([2R-(2alpha,4aalpha,8beta,8abeta)]-Decahydro-8-[2-hydroxy-4-(2-propenyl)-6-[4-(2-propenyl)phenoxy]phenoxy]-alpha,alpha,4a,8-tetramethyl-2-naphthalenemethanol)

3D SDF for NP0059293 ([2R-(2alpha,4aalpha,8beta,8abeta)]-Decahydro-8-[2-hydroxy-4-(2-propenyl)-6-[4-(2-propenyl)phenoxy]phenoxy]-alpha,alpha,4a,8-tetramethyl-2-naphthalenemethanol)

3D-SDF for NP0059293 ([2R-(2alpha,4aalpha,8beta,8abeta)]-Decahydro-8-[2-hydroxy-4-(2-propenyl)-6-[4-(2-propenyl)phenoxy]phenoxy]-alpha,alpha,4a,8-tetramethyl-2-naphthalenemethanol)

PDB for NP0059293 ([2R-(2alpha,4aalpha,8beta,8abeta)]-Decahydro-8-[2-hydroxy-4-(2-propenyl)-6-[4-(2-propenyl)phenoxy]phenoxy]-alpha,alpha,4a,8-tetramethyl-2-naphthalenemethanol)

3D PDB for NP0059293 ([2R-(2alpha,4aalpha,8beta,8abeta)]-Decahydro-8-[2-hydroxy-4-(2-propenyl)-6-[4-(2-propenyl)phenoxy]phenoxy]-alpha,alpha,4a,8-tetramethyl-2-naphthalenemethanol)

SMILES for NP0059293 ([2R-(2alpha,4aalpha,8beta,8abeta)]-Decahydro-8-[2-hydroxy-4-(2-propenyl)-6-[4-(2-propenyl)phenoxy]phenoxy]-alpha,alpha,4a,8-tetramethyl-2-naphthalenemethanol)

INCHI for NP0059293 ([2R-(2alpha,4aalpha,8beta,8abeta)]-Decahydro-8-[2-hydroxy-4-(2-propenyl)-6-[4-(2-propenyl)phenoxy]phenoxy]-alpha,alpha,4a,8-tetramethyl-2-naphthalenemethanol)

Structure for NP0059293 ([2R-(2alpha,4aalpha,8beta,8abeta)]-Decahydro-8-[2-hydroxy-4-(2-propenyl)-6-[4-(2-propenyl)phenoxy]phenoxy]-alpha,alpha,4a,8-tetramethyl-2-naphthalenemethanol)

3D Structure for NP0059293 ([2R-(2alpha,4aalpha,8beta,8abeta)]-Decahydro-8-[2-hydroxy-4-(2-propenyl)-6-[4-(2-propenyl)phenoxy]phenoxy]-alpha,alpha,4a,8-tetramethyl-2-naphthalenemethanol)