NP-MRD: Showing NP-Card for 2,3-Epoxyrubescin H (NP0332509)

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Record Information

Version

2.0

Created at

2024-02-15 20:03:56 UTC

Updated at

2024-09-03 04:19:27 UTC

NP-MRD ID

NP0332509

Natural Product DOI

https://doi.org/10.57994/1762

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2,3-Epoxyrubescin H

Description

2,3-Epoxyrubescin H belongs to the class of organic compounds known as vitamin d and derivatives. Vitamin D and derivatives are compounds containing a secosteroid backbone, usually secoergostane or secocholestane. Based on a literature review very few articles have been published on 2,3-Epoxyrubescin H.

Structure

MOL SDF PDB SMILES InChI


  Mrv2104 02152420032D          

 32 40  0  0  1  0            999 V2000
    5.4824   -1.3486    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5015   -0.5238    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2481   -0.1486    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.9763    0.2392    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2764    0.6759    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.5731    1.1441    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.2455    1.6220    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3632    1.9588    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5309    2.0223    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7610   -0.1075    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.7292   -0.9319    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8418    0.7322    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1793    1.2501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3784    0.9127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4342    0.1363    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.9815   -0.5535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9555   -0.4818    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4334   -1.1636    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.2381   -1.2889    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5944   -1.1370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2253   -0.3758    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7310   -1.0364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6640    0.3673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0291    0.9416    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1476    1.7580    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2785    0.5819    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3958   -0.2373    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8057   -0.8139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9253   -1.6302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1859   -1.9961    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3906   -1.4060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0076   -0.6754    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  3  2  1  0  0  0  0
  3  4  1  1  0  0  0
  5  3  1  0  0  0  0
  5  4  1  1  0  0  0
  5  6  1  0  0  0  0
  6  7  1  1  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
 10  2  1  0  0  0  0
 10 11  1  1  0  0  0
 10 12  1  0  0  0  0
  6 12  1  0  0  0  0
 12 13  2  0  0  0  0
  9 13  1  0  0  0  0
 13 14  1  0  0  0  0
 15 14  1  0  0  0  0
 15 16  1  1  0  0  0
 17 15  1  0  0  0  0
 17 10  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  1  0  0  0
 17 19  1  1  0  0  0
 18 20  1  0  0  0  0
 21 20  1  0  0  0  0
 21 22  1  6  0  0  0
 21 23  1  0  0  0  0
 15 23  1  0  0  0  0
 14 23  1  0  0  0  0
 24 23  1  0  0  0  0
 24 25  1  1  0  0  0
 24 26  1  0  0  0  0
 27 26  1  0  0  0  0
 21 27  1  0  0  0  0
 27 28  1  6  0  0  0
 28 29  2  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
 28 32  1  0  0  0  0
M  END


  Mrv2104 02152420032D          

 32 40  0  0  1  0            999 V2000
    5.4824   -1.3486    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5015   -0.5238    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2481   -0.1486    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.9763    0.2392    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2764    0.6759    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.5731    1.1441    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.2455    1.6220    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3632    1.9588    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5309    2.0223    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7610   -0.1075    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.7292   -0.9319    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8418    0.7322    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1793    1.2501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3784    0.9127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4342    0.1363    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.9815   -0.5535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9555   -0.4818    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4334   -1.1636    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.2381   -1.2889    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5944   -1.1370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2253   -0.3758    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7310   -1.0364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6640    0.3673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0291    0.9416    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1476    1.7580    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2785    0.5819    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3958   -0.2373    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8057   -0.8139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9253   -1.6302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1859   -1.9961    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3906   -1.4060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0076   -0.6754    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  3  2  1  0  0  0  0
  3  4  1  1  0  0  0
  5  3  1  0  0  0  0
  5  4  1  1  0  0  0
  5  6  1  0  0  0  0
  6  7  1  1  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
 10  2  1  0  0  0  0
 10 11  1  1  0  0  0
 10 12  1  0  0  0  0
  6 12  1  0  0  0  0
 12 13  2  0  0  0  0
  9 13  1  0  0  0  0
 13 14  1  0  0  0  0
 15 14  1  0  0  0  0
 15 16  1  1  0  0  0
 17 15  1  0  0  0  0
 17 10  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  1  0  0  0
 17 19  1  1  0  0  0
 18 20  1  0  0  0  0
 21 20  1  0  0  0  0
 21 22  1  6  0  0  0
 21 23  1  0  0  0  0
 15 23  1  0  0  0  0
 14 23  1  0  0  0  0
 24 23  1  0  0  0  0
 24 25  1  1  0  0  0
 24 26  1  0  0  0  0
 27 26  1  0  0  0  0
 21 27  1  0  0  0  0
 27 28  1  6  0  0  0
 28 29  2  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
 28 32  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0332509

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@]12C3C4=C5[C@](C)(CO4)[C@H]4O[C@H]4C(=O)[C@]5(C)[C@@]11O[C@H]1C[C@@]1(C)[C@@H](C[C@@H](O)C231)C1=COC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C26H28O6/c1-21-10-30-15-17(21)23(3,19(28)16-20(21)31-16)26-14(32-26)8-22(2)12(11-5-6-29-9-11)7-13(27)25(22)18(15)24(25,26)4/h5-6,9,12-14,16,18,20,27H,7-8,10H2,1-4H3/t12-,13+,14-,16-,18?,20-,21-,22-,23+,24-,25?,26+/m0/s1

> <INCHI_KEY>
CAVCUONDZKLHSL-MOVHEPJRSA-N

> <FORMULA>
C26H28O6

> <MOLECULAR_WEIGHT>
436.504

> <EXACT_MASS>
436.188588622

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
60

> <JCHEM_AVERAGE_POLARIZABILITY>
44.94528063054455

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,2S,4S,6S,7R,9R,11S,16R,17R,19R)-7-(furan-3-yl)-9-hydroxy-1,6,11,16-tetramethyl-3,14,18-trioxaoctacyclo[11.7.1.0^{2,4}.0^{2,11}.0^{6,10}.0^{10,12}.0^{16,21}.0^{17,19}]henicos-13(21)-en-20-one

> <JCHEM_LOGP>
1.2568792619999987

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
9

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.61747185956676

> <JCHEM_PKA_STRONGEST_BASIC>
-2.7672890719180594

> <JCHEM_POLAR_SURFACE_AREA>
84.73

> <JCHEM_REFRACTIVITY>
111.82919999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2S,4S,6S,7R,9R,11S,16R,17R,19R)-7-(furan-3-yl)-9-hydroxy-1,6,11,16-tetramethyl-3,14,18-trioxaoctacyclo[11.7.1.0^{2,4}.0^{2,11}.0^{6,10}.0^{10,12}.0^{16,21}.0^{17,19}]henicos-13(21)-en-20-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 15-FEB-24   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   15-FEB-24         0                                  
HETATM    1  O   UNK     0      10.234  -2.517   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      10.270  -0.978   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      11.663  -0.277   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      13.022   0.446   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      11.716   1.262   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      10.403   2.136   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      11.658   3.028   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      10.011   3.656   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       8.458   3.775   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       8.887  -0.201   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.828  -1.740   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       9.038   1.367   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.801   2.333   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.306   1.704   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.410   0.254   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.566  -1.033   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       7.384  -0.899   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.409  -2.172   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       7.911  -2.406   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       4.843  -2.122   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.154  -0.702   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       3.231  -1.935   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       4.973   0.686   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       3.788   1.758   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       4.009   3.282   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       2.387   1.086   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       2.606  -0.443   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       1.504  -1.519   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       1.727  -3.043   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       0.347  -3.726   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      -0.729  -2.625   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -0.014  -1.261   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   10                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3    5                                                       
CONECT    5    3    4    6                                                  
CONECT    6    5    7    8   12                                             
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8   13                                                       
CONECT   10    2   11   12   17                                             
CONECT   11   10                                                            
CONECT   12   10    6   13                                                  
CONECT   13   12    9   14                                                  
CONECT   14   13   15   23                                                  
CONECT   15   14   16   17   23                                             
CONECT   16   15                                                            
CONECT   17   15   10   18   19                                             
CONECT   18   17   19   20                                                  
CONECT   19   18   17                                                       
CONECT   20   18   21                                                       
CONECT   21   20   22   23   27                                             
CONECT   22   21                                                            
CONECT   23   21   15   14   24                                             
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   27                                                       
CONECT   27   26   21   28                                                  
CONECT   28   27   29   32                                                  
CONECT   29   28   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   28                                                       
MASTER        0    0    0    0    0    0    0    0   32    0   80    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₆H₂₈O₆

Average Mass

436.5040 Da

Monoisotopic Mass

436.18859 Da

IUPAC Name

(1S,2S,4S,6S,7R,9R,11S,16R,17R,19R)-7-(furan-3-yl)-9-hydroxy-1,6,11,16-tetramethyl-3,14,18-trioxaoctacyclo[11.7.1.0^{2,4}.0^{2,11}.0^{6,10}.0^{10,12}.0^{16,21}.0^{17,19}]henicos-13(21)-en-20-one

Traditional Name

(1S,2S,4S,6S,7R,9R,11S,16R,17R,19R)-7-(furan-3-yl)-9-hydroxy-1,6,11,16-tetramethyl-3,14,18-trioxaoctacyclo[11.7.1.0^{2,4}.0^{2,11}.0^{6,10}.0^{10,12}.0^{16,21}.0^{17,19}]henicos-13(21)-en-20-one

CAS Registry Number

Not Available

SMILES

C[C@@]12C3C4=C5[C@](C)(CO4)[C@H]4O[C@H]4C(=O)[C@]5(C)[C@@]11O[C@H]1C[C@@]1(C)[C@@H](C[C@@H](O)C231)C1=COC=C1

InChI Identifier

InChI=1S/C26H28O6/c1-21-10-30-15-17(21)23(3,19(28)16-20(21)31-16)26-14(32-26)8-22(2)12(11-5-6-29-9-11)7-13(27)25(22)18(15)24(25,26)4/h5-6,9,12-14,16,18,20,27H,7-8,10H2,1-4H3/t12-,13+,14-,16-,18?,20-,21-,22-,23+,24-,25?,26+/m0/s1

InChI Key

CAVCUONDZKLHSL-MOVHEPJRSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
COSY NMR	[Proton, Proton] NMR Spectrum (2D, 600 MHz, CDCL3, experimental)	kngoto@p.kanazawa-u.ac.jp	Not Available	Not Available	2024-02-15	View Spectrum
1D NMR	Carbon¹³ NMR Spectrum (1D, 151 MHz, CDCL3, experimental)	kngoto@p.kanazawa-u.ac.jp	Not Available	Not Available	2024-02-15	View Spectrum
HMQC NMR	[Proton, Carbon¹³] NMR Spectrum (2D, 600 MHz, CDCL3, experimental)	kngoto@p.kanazawa-u.ac.jp	Not Available	Not Available	2024-02-15	View Spectrum
1D NMR	Proton NMR Spectrum (1D, 600 MHz, CDCL3, experimental)	kngoto@p.kanazawa-u.ac.jp	Not Available	Not Available	2024-02-15	View Spectrum
HMBC NMR	[Proton, Carbon¹³] NMR Spectrum (2D, 600 MHz, CDCL3, experimental)	kngoto@p.kanazawa-u.ac.jp	Not Available	Not Available	2024-02-15	View Spectrum
NOESY NMR	[Proton, Proton] NMR Spectrum (2D, 600 MHz, CDCL3, experimental)	kngoto@p.kanazawa-u.ac.jp	Not Available	Not Available	2024-02-15	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

Chemical Taxonomy

Description

This compound belongs to the class of organic compounds known as vitamin d and derivatives. These are compounds containing a secosteroid backbone, usually secoergostane or secocholestane.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Vitamin D and derivatives

Direct Parent

Vitamin D and derivatives

Alternative Parents

Substituents

Triterpenoid
Naphthofuran
Oxepane
Monosaccharide
Heteroaromatic compound
Furan
Dihydrofuran
Cyclic alcohol
Secondary alcohol
Ketone
Oxacycle
Organoheterocyclic compound
Ether
Oxirane
Dialkyl ether
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Alcohol
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	1.26	ChemAxon
pKa (Strongest Acidic)	14.62	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	84.73 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	111.83 m³·mol⁻¹	ChemAxon
Polarizability	44.95 Å³	ChemAxon
Number of Rings	9	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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

DOI: 10.3390/molecules29030651

Showing NP-Card for 2,3-Epoxyrubescin H (NP0332509)

MOL for NP0332509 (2,3-Epoxyrubescin H)

3D MOL for NP0332509 (2,3-Epoxyrubescin H)

3D SDF for NP0332509 (2,3-Epoxyrubescin H)

3D-SDF for NP0332509 (2,3-Epoxyrubescin H)

PDB for NP0332509 (2,3-Epoxyrubescin H)

3D PDB for NP0332509 (2,3-Epoxyrubescin H)

SMILES for NP0332509 (2,3-Epoxyrubescin H)

INCHI for NP0332509 (2,3-Epoxyrubescin H)

Structure for NP0332509 (2,3-Epoxyrubescin H)

3D Structure for NP0332509 (2,3-Epoxyrubescin H)