NP-MRD: Showing NP-Card for 10,14-dihydroxy-6,6,16,20,20-pentamethyl-15-(3-methylbut-2-en-1-yl)-7,21,23-trioxahexacyclo[11.8.1.1¹,¹⁹.0²,¹¹.0³,⁸.0¹⁷,²²]tricosa-2,4,8,10,13,15,17(22)-heptaen-12-one (NP0322017)

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Record Information

Version

2.0

Created at

2022-09-12 00:32:28 UTC

Updated at

2022-09-12 00:32:28 UTC

NP-MRD ID

NP0322017

Secondary Accession Numbers

None

Natural Product Identification

Common Name

10,14-dihydroxy-6,6,16,20,20-pentamethyl-15-(3-methylbut-2-en-1-yl)-7,21,23-trioxahexacyclo[11.8.1.1¹,¹⁹.0²,¹¹.0³,⁸.0¹⁷,²²]tricosa-2,4,8,10,13,15,17(22)-heptaen-12-one

Description

10,14-Dihydroxy-6,6,16,20,20-pentamethyl-15-(3-methylbut-2-en-1-yl)-7,21,23-trioxahexacyclo[11.8.1.1¹,¹⁹.0²,¹¹.0³,⁸.0¹⁷,²²]Tricosa-2(11),3(8),4,9,13,15,17(22)-heptaen-12-one belongs to the class of organic compounds known as naphthopyrans. Naphthopyrans are compounds containing a pyran ring fused to a naphthalene moiety. Furan is a 6 membered-ring non-aromatic ring with five carbon and one oxygen atoms. Naphthalene is a polycyclic aromatic hydrocarbon made up of two fused benzene rings. 10,14-dihydroxy-6,6,16,20,20-pentamethyl-15-(3-methylbut-2-en-1-yl)-7,21,23-trioxahexacyclo[11.8.1.1¹,¹⁹.0²,¹¹.0³,⁸.0¹⁷,²²]tricosa-2,4,8,10,13,15,17(22)-heptaen-12-one is found in Harungana madagascariensis. 10,14-Dihydroxy-6,6,16,20,20-pentamethyl-15-(3-methylbut-2-en-1-yl)-7,21,23-trioxahexacyclo[11.8.1.1¹,¹⁹.0²,¹¹.0³,⁸.0¹⁷,²²]Tricosa-2(11),3(8),4,9,13,15,17(22)-heptaen-12-one is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004231520142D          

 36 41  0  0  0  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1533004231520142D          

 36 41  0  0  0  0            999 V2000
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  6  7  1  0  0  0  0
  6  8  1  0  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  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 10 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
 12 17  1  0  0  0  0
  8 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 22 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 27 29  1  0  0  0  0
 27 30  1  0  0  0  0
 30 31  2  0  0  0  0
 31 32  1  0  0  0  0
 25 32  1  0  0  0  0
 32 33  2  0  0  0  0
 12 33  1  0  0  0  0
 21 33  1  0  0  0  0
 18 34  2  0  0  0  0
  5 34  1  0  0  0  0
 34 35  1  0  0  0  0
  2 36  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0322017

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)=CCC1=C(C)C2=C3C(=C1O)C(=O)C1=C(O)C=C4OC(C)(C)C=CC4=C1C31OC(C2)C(C)(C)O1

> <INCHI_IDENTIFIER>
InChI=1S/C30H32O6/c1-14(2)8-9-16-15(3)18-12-21-29(6,7)36-30(35-21)24-17-10-11-28(4,5)34-20(17)13-19(31)22(24)27(33)23(25(18)30)26(16)32/h8,10-11,13,21,31-32H,9,12H2,1-7H3

> <INCHI_KEY>
IKVXOPKGYVAIGC-UHFFFAOYSA-N

> <FORMULA>
C30H32O6

> <MOLECULAR_WEIGHT>
488.58

> <EXACT_MASS>
488.21988875

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
68

> <JCHEM_AVERAGE_POLARIZABILITY>
54.71615824753292

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
10,14-dihydroxy-6,6,16,20,20-pentamethyl-15-(3-methylbut-2-en-1-yl)-7,21,23-trioxahexacyclo[11.8.1.1¹,¹⁹.0²,¹¹.0³,⁸.0¹⁷,²²]tricosa-2,4,8,10,13,15,17(22)-heptaen-12-one

> <ALOGPS_LOGP>
4.96

> <JCHEM_LOGP>
8.033575896333334

> <ALOGPS_LOGS>
-5.33

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.939834309415613

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.291516526396714

> <JCHEM_PKA_STRONGEST_BASIC>
-4.0747236054214495

> <JCHEM_POLAR_SURFACE_AREA>
85.22000000000001

> <JCHEM_REFRACTIVITY>
140.3509

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.27e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
10,14-dihydroxy-6,6,16,20,20-pentamethyl-15-(3-methylbut-2-en-1-yl)-7,21,23-trioxahexacyclo[11.8.1.1¹,¹⁹.0²,¹¹.0³,⁸.0¹⁷,²²]tricosa-2,4,8,10,13,15,17(22)-heptaen-12-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 23-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-APR-15         0                                  
HETATM    1  C   UNK     0      -2.659  -5.295   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.201  -3.825   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.698  -3.486   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.240  -2.016   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.262  -1.677   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.733  -0.206   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.695   0.932   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.248   0.132   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.763   1.655   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.369   1.965   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       5.638   0.628   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       5.996  -0.674   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       7.371   0.291   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       7.006   1.874   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.451   2.408   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       7.287   3.388   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.369  -1.039   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.875  -2.522   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.945  -3.670   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       4.456  -5.130   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       6.472  -3.402   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       7.484  -4.563   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       6.984  -6.020   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       8.995  -4.268   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       9.495  -2.811   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      11.006  -2.515   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      11.506  -1.059   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      12.853  -1.804   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      12.473   0.139   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      10.494   0.103   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       8.982  -0.193   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       8.483  -1.650   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       6.972  -1.945   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       2.327  -2.813   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0       1.849  -4.277   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0      -3.245  -2.693   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   36                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   34                                                  
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   17                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   14                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   17   33                                             
CONECT   13   12   14                                                       
CONECT   14   13   10   15   16                                             
CONECT   15   14                                                            
CONECT   16   14                                                            
CONECT   17   12    8   18                                                  
CONECT   18   17   19   34                                                  
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22   33                                                  
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25                                                       
CONECT   25   24   26   32                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28   29   30                                             
CONECT   28   27                                                            
CONECT   29   27                                                            
CONECT   30   27   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   25   33                                                  
CONECT   33   32   12   21                                                  
CONECT   34   18    5   35                                                  
CONECT   35   34                                                            
CONECT   36    2                                                            
MASTER        0    0    0    0    0    0    0    0   36    0   82    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₀H₃₂O₆

Average Mass

488.5800 Da

Monoisotopic Mass

488.21989 Da

IUPAC Name

10,14-dihydroxy-6,6,16,20,20-pentamethyl-15-(3-methylbut-2-en-1-yl)-7,21,23-trioxahexacyclo[11.8.1.1¹,¹⁹.0²,¹¹.0³,⁸.0¹⁷,²²]tricosa-2,4,8,10,13,15,17(22)-heptaen-12-one

Traditional Name

10,14-dihydroxy-6,6,16,20,20-pentamethyl-15-(3-methylbut-2-en-1-yl)-7,21,23-trioxahexacyclo[11.8.1.1¹,¹⁹.0²,¹¹.0³,⁸.0¹⁷,²²]tricosa-2,4,8,10,13,15,17(22)-heptaen-12-one

CAS Registry Number

Not Available

SMILES

CC(C)=CCC1=C(C)C2=C3C(=C1O)C(=O)C1=C(O)C=C4OC(C)(C)C=CC4=C1C31OC(C2)C(C)(C)O1

InChI Identifier

InChI=1S/C30H32O6/c1-14(2)8-9-16-15(3)18-12-21-29(6,7)36-30(35-21)24-17-10-11-28(4,5)34-20(17)13-19(31)22(24)27(33)23(25(18)30)26(16)32/h8,10-11,13,21,31-32H,9,12H2,1-7H3

InChI Key

IKVXOPKGYVAIGC-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
Harungana madagascariensis	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as naphthopyrans. Naphthopyrans are compounds containing a pyran ring fused to a naphthalene moiety. Furan is a 6 membered-ring non-aromatic ring with five carbon and one oxygen atoms. Naphthalene is a polycyclic aromatic hydrocarbon made up of two fused benzene rings.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Naphthopyrans

Sub Class

Not Available

Direct Parent

Naphthopyrans

Alternative Parents

Substituents

Anthracene
Naphthopyran
2,2-dimethyl-1-benzopyran
Benzopyran
Isochromane
1-benzopyran
2-benzopyran
Aryl ketone
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Ketal
Pyran
Benzenoid
Vinylogous acid
Meta-dioxolane
Ketone
Ether
Oxacycle
Acetal
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Aldehyde
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	4.96	ALOGPS
logP	8.03	ChemAxon
logS	-5.3	ALOGPS
pKa (Strongest Acidic)	8.29	ChemAxon
pKa (Strongest Basic)	-4.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	85.22 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	140.35 m³·mol⁻¹	ChemAxon
Polarizability	54.72 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	Yes	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

102080583

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 10,14-dihydroxy-6,6,16,20,20-pentamethyl-15-(3-methylbut-2-en-1-yl)-7,21,23-trioxahexacyclo[11.8.1.1¹,¹⁹.0²,¹¹.0³,⁸.0¹⁷,²²]tricosa-2,4,8,10,13,15,17(22)-heptaen-12-one (NP0322017)

MOL for NP0322017 (10,14-dihydroxy-6,6,16,20,20-pentamethyl-15-(3-methylbut-2-en-1-yl)-7,21,23-trioxahexacyclo[11.8.1.1¹,¹⁹.0²,¹¹.0³,⁸.0¹⁷,²²]tricosa-2,4,8,10,13,15,17(22)-heptaen-12-one)

3D MOL for NP0322017 (10,14-dihydroxy-6,6,16,20,20-pentamethyl-15-(3-methylbut-2-en-1-yl)-7,21,23-trioxahexacyclo[11.8.1.1¹,¹⁹.0²,¹¹.0³,⁸.0¹⁷,²²]tricosa-2,4,8,10,13,15,17(22)-heptaen-12-one)

3D SDF for NP0322017 (10,14-dihydroxy-6,6,16,20,20-pentamethyl-15-(3-methylbut-2-en-1-yl)-7,21,23-trioxahexacyclo[11.8.1.1¹,¹⁹.0²,¹¹.0³,⁸.0¹⁷,²²]tricosa-2,4,8,10,13,15,17(22)-heptaen-12-one)

3D-SDF for NP0322017 (10,14-dihydroxy-6,6,16,20,20-pentamethyl-15-(3-methylbut-2-en-1-yl)-7,21,23-trioxahexacyclo[11.8.1.1¹,¹⁹.0²,¹¹.0³,⁸.0¹⁷,²²]tricosa-2,4,8,10,13,15,17(22)-heptaen-12-one)

PDB for NP0322017 (10,14-dihydroxy-6,6,16,20,20-pentamethyl-15-(3-methylbut-2-en-1-yl)-7,21,23-trioxahexacyclo[11.8.1.1¹,¹⁹.0²,¹¹.0³,⁸.0¹⁷,²²]tricosa-2,4,8,10,13,15,17(22)-heptaen-12-one)

3D PDB for NP0322017 (10,14-dihydroxy-6,6,16,20,20-pentamethyl-15-(3-methylbut-2-en-1-yl)-7,21,23-trioxahexacyclo[11.8.1.1¹,¹⁹.0²,¹¹.0³,⁸.0¹⁷,²²]tricosa-2,4,8,10,13,15,17(22)-heptaen-12-one)

SMILES for NP0322017 (10,14-dihydroxy-6,6,16,20,20-pentamethyl-15-(3-methylbut-2-en-1-yl)-7,21,23-trioxahexacyclo[11.8.1.1¹,¹⁹.0²,¹¹.0³,⁸.0¹⁷,²²]tricosa-2,4,8,10,13,15,17(22)-heptaen-12-one)

INCHI for NP0322017 (10,14-dihydroxy-6,6,16,20,20-pentamethyl-15-(3-methylbut-2-en-1-yl)-7,21,23-trioxahexacyclo[11.8.1.1¹,¹⁹.0²,¹¹.0³,⁸.0¹⁷,²²]tricosa-2,4,8,10,13,15,17(22)-heptaen-12-one)

Structure for NP0322017 (10,14-dihydroxy-6,6,16,20,20-pentamethyl-15-(3-methylbut-2-en-1-yl)-7,21,23-trioxahexacyclo[11.8.1.1¹,¹⁹.0²,¹¹.0³,⁸.0¹⁷,²²]tricosa-2,4,8,10,13,15,17(22)-heptaen-12-one)

3D Structure for NP0322017 (10,14-dihydroxy-6,6,16,20,20-pentamethyl-15-(3-methylbut-2-en-1-yl)-7,21,23-trioxahexacyclo[11.8.1.1¹,¹⁹.0²,¹¹.0³,⁸.0¹⁷,²²]tricosa-2,4,8,10,13,15,17(22)-heptaen-12-one)