NP-MRD: Showing NP-Card for (+)-Akashin B (NP0068796)

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Record Information

Version

2.0

Created at

2022-04-28 14:03:06 UTC

Updated at

2022-04-28 14:03:06 UTC

NP-MRD ID

NP0068796

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(+)-Akashin B

Description

(+)-Akashin B is found in Streptomyces sp.GW48-1497.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282216032D          

 35 39  0  0  1  0            999 V2000
   -5.2008   -1.7916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2008   -0.9666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4863   -0.5541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7718   -0.9666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7718   -1.7916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4863   -2.2041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9872   -2.0465    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5023   -1.3791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6773   -1.3791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1923   -0.7116    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4077   -0.9666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4077   -1.7916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1923   -2.0465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4473   -2.8311    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3067   -2.2041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0212   -1.7916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0212   -0.9666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3067   -0.5541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7357   -2.2041    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -2.9872   -0.7116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7322    0.0730    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7322   -2.8311    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.2843   -3.4442    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.0293   -4.2288    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.2224   -4.4004    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6703   -3.7873    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.9253   -3.0027    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8634   -3.9588    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9674   -5.1850    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5195   -5.7981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3264   -5.6266    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2645   -6.5827    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5814   -4.8419    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0913   -3.2727    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9152   -0.5541    0.0000 Cl  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
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  4  5  1  0  0  0  0
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  9 13  1  0  0  0  0
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 11 18  1  0  0  0  0
 16 19  1  0  0  0  0
  8 20  1  0  0  0  0
  4 20  1  0  0  0  0
 20 21  2  0  0  0  0
 22  7  1  1  0  0  0
 22 23  1  0  0  0  0
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 26 27  1  0  0  0  0
 22 27  1  0  0  0  0
 26 28  1  1  0  0  0
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 30 32  1  0  0  0  0
 24 33  1  1  0  0  0
 23 34  1  6  0  0  0
  2 35  1  0  0  0  0
M  END

     RDKit          3D

 56 60  0  0  0  0  0  0  0  0999 V2000
    6.5296   -1.6167   -0.3557 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3943   -0.7000   -0.0920 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5975    0.3884    0.5006 O   0  0  0  0  0  0  0  0  0  0  0  0
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    2.9340   -0.2028   -0.2811 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2327    0.1879   -1.5467 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.1536    0.9637   -2.4649 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1760    1.0482   -1.2347 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1391    0.3213   -0.5566 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0024    1.1388   -0.4897 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3216    0.8546   -0.0973 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8422   -0.3344    0.1626 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2040   -0.5293    0.5686 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3969   -1.9490    0.6892 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5462   -2.6100    1.0552 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5377   -3.9858    1.1159 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3893   -4.6573    0.8112 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3660   -6.3979    0.8842 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -3.2470   -3.9907    0.4469 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2268   -2.5948    0.3769 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1937   -1.6072    0.0303 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0830   -1.9689   -0.2806 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1270    2.0953   -0.1038 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3258    2.2531    0.1827 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1993    3.1379   -0.5301 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4187    4.4958   -0.7112 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4007    5.3148   -1.1208 C   0  0  0  0  0  0  0  0  0  0  0  0
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 11 10  1  0
 21 12  1  0
 25 31  1  0
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  7 42  1  0
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M  END


  Mrv1652304282216032D          

 35 39  0  0  1  0            999 V2000
   -5.2008   -1.7916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2008   -0.9666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4863   -0.5541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7718   -0.9666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7718   -1.7916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4863   -2.2041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.5023   -1.3791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6773   -1.3791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.7357   -2.2041    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
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  1  2  2  0  0  0  0
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  8 20  1  0  0  0  0
  4 20  1  0  0  0  0
 20 21  2  0  0  0  0
 22  7  1  1  0  0  0
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 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 22 27  1  0  0  0  0
 26 28  1  1  0  0  0
 25 29  1  6  0  0  0
 29 30  1  0  0  0  0
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M  END
> <DATABASE_ID>
NP0068796

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H]1O[C@@H]([C@@H](O)[C@H](O)[C@H]1NC(C)=O)N1C2=CC=C(Cl)C=C2C(=O)\C1=C1/NC2=C(C=C(Cl)C=C2)C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C24H21Cl2N3O6/c1-9-17(27-10(2)30)22(33)23(34)24(35-9)29-16-6-4-12(26)8-14(16)21(32)19(29)18-20(31)13-7-11(25)3-5-15(13)28-18/h3-9,17,22-24,28,33-34H,1-2H3,(H,27,30)/b19-18+/t9-,17-,22+,23-,24-/m0/s1

> <INCHI_KEY>
SASZYHICLXZFCO-YFOBLGOOSA-N

> <FORMULA>
C24H21Cl2N3O6

> <MOLECULAR_WEIGHT>
518.35

> <EXACT_MASS>
517.0807408

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
56

> <JCHEM_AVERAGE_POLARIZABILITY>
50.49129001471833

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
N-[(2S,3R,4R,5S,6S)-6-[(E)-5,5'-dichloro-3,3'-dioxo-1H,1'H,3H,3'H-[2,2'-biindolylidene]-1-yl]-4,5-dihydroxy-2-methyloxan-3-yl]acetamide

> <ALOGPS_LOGP>
2.50

> <JCHEM_LOGP>
2.190628275

> <ALOGPS_LOGS>
-3.18

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.210031754107725

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.952666041679004

> <JCHEM_PKA_STRONGEST_BASIC>
-1.3422222146093463

> <JCHEM_POLAR_SURFACE_AREA>
128.20000000000002

> <JCHEM_REFRACTIVITY>
131.10509999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.42e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
N-[(2S,3R,4R,5S,6S)-6-[(E)-5,5'-dichloro-3,3'-dioxo-1'H-[2,2'-biindolylidene]-1-yl]-4,5-dihydroxy-2-methyloxan-3-yl]acetamide

> <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      -9.708  -3.344   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -9.708  -1.804   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -8.374  -1.034   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -7.041  -1.804   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -7.041  -3.344   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -8.374  -4.114   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0      -5.576  -3.820   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0      -4.671  -2.574   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -3.131  -2.574   0.000  0.00  0.00           C+0
HETATM   10  N   UNK     0      -2.226  -1.328   0.000  0.00  0.00           N+0
HETATM   11  C   UNK     0      -0.761  -1.804   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.761  -3.344   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -2.226  -3.820   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      -2.702  -5.285   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       0.573  -4.114   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.906  -3.344   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.906  -1.804   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.573  -1.034   0.000  0.00  0.00           C+0
HETATM   19 Cl   UNK     0       3.240  -4.114   0.000  0.00  0.00          Cl+0
HETATM   20  C   UNK     0      -5.576  -1.328   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      -5.100   0.136   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      -5.100  -5.285   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -6.131  -6.429   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -5.655  -7.894   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -4.148  -8.214   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -3.118  -7.070   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      -3.594  -5.605   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      -1.612  -7.390   0.000  0.00  0.00           C+0
HETATM   29  N   UNK     0      -3.673  -9.679   0.000  0.00  0.00           N+0
HETATM   30  C   UNK     0      -4.703 -10.823   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      -6.209 -10.503   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      -4.227 -12.288   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      -6.685  -9.038   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0      -7.637  -6.109   0.000  0.00  0.00           O+0
HETATM   35 Cl   UNK     0     -11.042  -1.034   0.000  0.00  0.00          Cl+0
CONECT    1    2    6                                                       
CONECT    2    1    3   35                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   20                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5    1                                                       
CONECT    7    5    8   22                                                  
CONECT    8    7    9   20                                                  
CONECT    9    8   10   13                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   18                                                  
CONECT   12   11   13   15                                                  
CONECT   13   12    9   14                                                  
CONECT   14   13                                                            
CONECT   15   12   16                                                       
CONECT   16   15   17   19                                                  
CONECT   17   16   18                                                       
CONECT   18   17   11                                                       
CONECT   19   16                                                            
CONECT   20    8    4   21                                                  
CONECT   21   20                                                            
CONECT   22    7   23   27                                                  
CONECT   23   22   24   34                                                  
CONECT   24   23   25   33                                                  
CONECT   25   24   26   29                                                  
CONECT   26   25   27   28                                                  
CONECT   27   26   22                                                       
CONECT   28   26                                                            
CONECT   29   25   30                                                       
CONECT   30   29   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30                                                            
CONECT   33   24                                                            
CONECT   34   23                                                            
CONECT   35    2                                                            
MASTER        0    0    0    0    0    0    0    0   35    0   78    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₄H₂₁Cl₂N₃O₆

Average Mass

518.3500 Da

Monoisotopic Mass

517.08074 Da

IUPAC Name

N-[(2S,3R,4R,5S,6S)-6-[(E)-5,5'-dichloro-3,3'-dioxo-1H,1'H,3H,3'H-[2,2'-biindolylidene]-1-yl]-4,5-dihydroxy-2-methyloxan-3-yl]acetamide

Traditional Name

N-[(2S,3R,4R,5S,6S)-6-[(E)-5,5'-dichloro-3,3'-dioxo-1'H-[2,2'-biindolylidene]-1-yl]-4,5-dihydroxy-2-methyloxan-3-yl]acetamide

CAS Registry Number

Not Available

SMILES

C[C@@H]1O[C@@H]([C@@H](O)[C@H](O)[C@H]1NC(C)=O)N1C2=CC=C(Cl)C=C2C(=O)\C1=C1/NC2=C(C=C(Cl)C=C2)C1=O

InChI Identifier

InChI=1S/C24H21Cl2N3O6/c1-9-17(27-10(2)30)22(33)23(34)24(35-9)29-16-6-4-12(26)8-14(16)21(32)19(29)18-20(31)13-7-11(25)3-5-15(13)28-18/h3-9,17,22-24,28,33-34H,1-2H3,(H,27,30)/b19-18+/t9-,17-,22+,23-,24-/m0/s1

InChI Key

SASZYHICLXZFCO-YFOBLGOOSA-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
Streptomyces sp.GW48-1497	Bacteria	KNApSAcK

Chemical Taxonomy

Classification

Not classified

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	2.5	ALOGPS
logP	2.19	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	7.95	ChemAxon
pKa (Strongest Basic)	-1.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	128.2 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	131.11 m³·mol⁻¹	ChemAxon
Polarizability	50.49 Å³	ChemAxon
Number of Rings	5	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

Not Available

References

General References

Not Available

Showing NP-Card for (+)-Akashin B (NP0068796)

MOL for NP0068796 ((+)-Akashin B)

3D MOL for NP0068796 ((+)-Akashin B)

3D SDF for NP0068796 ((+)-Akashin B)

3D-SDF for NP0068796 ((+)-Akashin B)

PDB for NP0068796 ((+)-Akashin B)

3D PDB for NP0068796 ((+)-Akashin B)

SMILES for NP0068796 ((+)-Akashin B)

INCHI for NP0068796 ((+)-Akashin B)

Structure for NP0068796 ((+)-Akashin B)

3D Structure for NP0068796 ((+)-Akashin B)