NP-MRD: Showing NP-Card for 3,7-Dihydroxy-25-methoxycucurbita-5,23-dien-19-al (NP0335866)

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Record Information

Version

2.0

Created at

2024-09-11 03:37:10 UTC

Updated at

2024-09-11 03:37:11 UTC

NP-MRD ID

NP0335866

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3,7-Dihydroxy-25-methoxycucurbita-5,23-dien-19-al

Description

3,7-Dihydroxy-25-methoxycucurbita-5,23-dien-19-al belongs to the class of organic compounds known as cucurbitacins. These are polycyclic compounds containing the tetracyclic cucurbitane nucleus skeleton, 19-(10->9b)-abeo-10alanost-5-ene (also known as 9b-methyl-19-nor lanosta-5-ene), with a variety of oxygenation functionalities at different positions. Based on a literature review a small amount of articles have been published on 3,7-Dihydroxy-25-methoxycucurbita-5,23-dien-19-al.

Structure

MOL SDF PDB SMILES InChI


  Mrv2104 05262306092D          

 35 38  0  0  0  0            999 V2000
    3.2730    2.5638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0599    1.7667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2628    1.5537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0498    0.7565    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2541    0.5435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9984   -0.2412    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4836   -0.9078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9984   -1.5757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2138   -1.3200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4996   -1.7323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4996   -2.5569    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2142   -2.9693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9275   -2.5569    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6422   -2.9693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3568   -2.5569    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3568   -1.7323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6422   -1.3200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9275   -1.7323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2142   -1.3200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2142   -0.4954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4996   -0.0831    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2138   -0.4954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3002    0.3250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6700    1.1262    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4874    3.3595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0700    2.3494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3002   -2.1405    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1727   -3.6015    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1116   -3.6015    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4772    2.7768    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9275   -0.0831    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9275   -0.9078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0700   -2.9693    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2138   -2.9693    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4772    3.6015    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1 25  1  0  0  0  0
  1 26  1  0  0  0  0
  1 30  1  0  0  0  0
  2  3  2  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
  5 24  1  0  0  0  0
  6  7  1  0  0  0  0
  6 22  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 22  1  0  0  0  0
  9 27  1  0  0  0  0
 10 11  1  0  0  0  0
 10 19  1  0  0  0  0
 11 12  1  0  0  0  0
 11 34  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 13 18  1  0  0  0  0
 14 15  1  0  0  0  0
 14 28  1  0  0  0  0
 14 29  1  0  0  0  0
 15 16  1  0  0  0  0
 15 33  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 32  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 30 35  1  0  0  0  0
 31 32  2  0  0  0  0
M  END


  Mrv2104 05262306092D          

 35 38  0  0  0  0            999 V2000
    3.2730    2.5638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0599    1.7667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2628    1.5537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0498    0.7565    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2541    0.5435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9984   -0.2412    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4836   -0.9078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9984   -1.5757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2138   -1.3200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4996   -1.7323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4996   -2.5569    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2142   -2.9693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9275   -2.5569    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6422   -2.9693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3568   -2.5569    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3568   -1.7323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6422   -1.3200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9275   -1.7323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2142   -1.3200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2142   -0.4954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4996   -0.0831    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2138   -0.4954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3002    0.3250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6700    1.1262    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4874    3.3595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0700    2.3494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3002   -2.1405    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1727   -3.6015    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1116   -3.6015    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4772    2.7768    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9275   -0.0831    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9275   -0.9078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0700   -2.9693    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2138   -2.9693    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4772    3.6015    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1 25  1  0  0  0  0
  1 26  1  0  0  0  0
  1 30  1  0  0  0  0
  2  3  2  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
  5 24  1  0  0  0  0
  6  7  1  0  0  0  0
  6 22  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 22  1  0  0  0  0
  9 27  1  0  0  0  0
 10 11  1  0  0  0  0
 10 19  1  0  0  0  0
 11 12  1  0  0  0  0
 11 34  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 13 18  1  0  0  0  0
 14 15  1  0  0  0  0
 14 28  1  0  0  0  0
 14 29  1  0  0  0  0
 15 16  1  0  0  0  0
 15 33  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 32  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 30 35  1  0  0  0  0
 31 32  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0335866

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(C)(C)\C=C\CC(C)C1CCC2(C)C3C(O)C=C4C(CCC(O)C4(C)C)C3(CCC12C)C=O

> <INCHI_IDENTIFIER>
InChI=1/C31H50O4/c1-20(10-9-14-27(2,3)35-8)21-13-15-30(7)26-24(33)18-23-22(11-12-25(34)28(23,4)5)31(26,19-32)17-16-29(21,30)6/h9,14,18-22,24-26,33-34H,10-13,15-17H2,1-8H3/b14-9+

> <INCHI_KEY>
AEUOCNAZOMRXEC-NTEUORMPNA-N

> <FORMULA>
C31H50O4

> <MOLECULAR_WEIGHT>
486.737

> <EXACT_MASS>
486.37091009

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
85

> <JCHEM_AVERAGE_POLARIZABILITY>
57.73789434429416

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
4,7-dihydroxy-1-[(4E)-6-methoxy-6-methylhept-4-en-2-yl]-3a,6,6,11a-tetramethyl-1H,2H,3H,3aH,3bH,4H,6H,7H,8H,9H,9aH,9bH,10H,11H,11aH-cyclopenta[a]phenanthrene-9b-carbaldehyde

> <JCHEM_LOGP>
5.002126458666667

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
19.40840003979616

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.515565729569738

> <JCHEM_PKA_STRONGEST_BASIC>
-0.8703466571802405

> <JCHEM_POLAR_SURFACE_AREA>
66.76

> <JCHEM_REFRACTIVITY>
143.7415

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
4,7-dihydroxy-1-[(4E)-6-methoxy-6-methylhept-4-en-2-yl]-3a,6,6,11a-tetramethyl-1H,2H,3H,3bH,4H,7H,8H,9H,9aH,10H,11H-cyclopenta[a]phenanthrene-9b-carbaldehyde

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 26-MAY-23   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-MAY-23         0                                  
HETATM    1  C   UNK     0       6.110   4.786   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.712   3.298   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.224   2.900   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.826   1.412   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.341   1.015   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.864  -0.450   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.769  -1.695   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.864  -2.941   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.399  -2.464   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.933  -3.234   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.933  -4.773   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -2.267  -5.543   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -3.598  -4.773   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -4.932  -5.543   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -6.266  -4.773   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -6.266  -3.234   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -4.932  -2.464   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -3.598  -3.234   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -2.267  -2.464   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -2.267  -0.925   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -0.933  -0.155   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       0.399  -0.925   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       0.560   0.607   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       1.251   2.102   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       6.510   6.271   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       7.597   4.386   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       0.560  -3.996   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -5.922  -6.723   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -3.942  -6.723   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       4.624   5.183   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0      -3.598  -0.155   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      -3.598  -1.695   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      -7.597  -5.543   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0       0.399  -5.543   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0       4.624   6.723   0.000  0.00  0.00           C+0
CONECT    1    2   25   26   30                                             
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   24                                                  
CONECT    6    5    7   22                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   22   27                                             
CONECT   10    9   11   19                                                  
CONECT   11   10   12   34                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   18                                                  
CONECT   14   13   15   28   29                                             
CONECT   15   14   16   33                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   13   17   19                                                  
CONECT   19   10   18   20   32                                             
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22    6    9   21   23                                             
CONECT   23   22                                                            
CONECT   24    5                                                            
CONECT   25    1                                                            
CONECT   26    1                                                            
CONECT   27    9                                                            
CONECT   28   14                                                            
CONECT   29   14                                                            
CONECT   30    1   35                                                       
CONECT   31   32                                                            
CONECT   32   19   31                                                       
CONECT   33   15                                                            
CONECT   34   11                                                            
CONECT   35   30                                                            
MASTER        0    0    0    0    0    0    0    0   35    0   76    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₁H₅₀O₄

Average Mass

486.7370 Da

Monoisotopic Mass

486.37091 Da

IUPAC Name

4,7-dihydroxy-1-[(4E)-6-methoxy-6-methylhept-4-en-2-yl]-3a,6,6,11a-tetramethyl-1H,2H,3H,3aH,3bH,4H,6H,7H,8H,9H,9aH,9bH,10H,11H,11aH-cyclopenta[a]phenanthrene-9b-carbaldehyde

Traditional Name

4,7-dihydroxy-1-[(4E)-6-methoxy-6-methylhept-4-en-2-yl]-3a,6,6,11a-tetramethyl-1H,2H,3H,3bH,4H,7H,8H,9H,9aH,10H,11H-cyclopenta[a]phenanthrene-9b-carbaldehyde

CAS Registry Number

Not Available

SMILES

COC(C)(C)\C=C\CC(C)C1CCC2(C)C3C(O)C=C4C(CCC(O)C4(C)C)C3(CCC12C)C=O

InChI Identifier

InChI=1/C31H50O4/c1-20(10-9-14-27(2,3)35-8)21-13-15-30(7)26-24(33)18-23-22(11-12-25(34)28(23,4)5)31(26,19-32)17-16-29(21,30)6/h9,14,18-22,24-26,33-34H,10-13,15-17H2,1-8H3/b14-9+

InChI Key

AEUOCNAZOMRXEC-NTEUORMPNA-N

Experimental Spectra

Not Available

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 cucurbitacins. These are polycyclic compounds containing the tetracyclic cucurbitane nucleus skeleton, 19-(10->9b)-abeo-10alanost-5-ene (also known as 9b-methyl-19-nor lanosta-5-ene), with a variety of oxygenation functionalities at different positions.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Cucurbitacins

Direct Parent

Cucurbitacins

Alternative Parents

Substituents

Cucurbitacin skeleton
Triterpenoid
3-hydroxy-delta-5-steroid
3-hydroxysteroid
7-hydroxysteroid
Hydroxysteroid
Delta-5-steroid
Cyclic alcohol
Secondary alcohol
Ether
Dialkyl ether
Organooxygen compound
Hydrocarbon derivative
Carbonyl group
Aldehyde
Alcohol
Organic oxygen compound
Organic oxide
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic 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	5	ChemAxon
pKa (Strongest Acidic)	14.52	ChemAxon
pKa (Strongest Basic)	-0.87	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	66.76 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	143.74 m³·mol⁻¹	ChemAxon
Polarizability	57.74 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	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

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

Showing NP-Card for 3,7-Dihydroxy-25-methoxycucurbita-5,23-dien-19-al (NP0335866)

MOL for NP0335866 (3,7-Dihydroxy-25-methoxycucurbita-5,23-dien-19-al)

3D MOL for NP0335866 (3,7-Dihydroxy-25-methoxycucurbita-5,23-dien-19-al)

3D SDF for NP0335866 (3,7-Dihydroxy-25-methoxycucurbita-5,23-dien-19-al)

3D-SDF for NP0335866 (3,7-Dihydroxy-25-methoxycucurbita-5,23-dien-19-al)

PDB for NP0335866 (3,7-Dihydroxy-25-methoxycucurbita-5,23-dien-19-al)

3D PDB for NP0335866 (3,7-Dihydroxy-25-methoxycucurbita-5,23-dien-19-al)

SMILES for NP0335866 (3,7-Dihydroxy-25-methoxycucurbita-5,23-dien-19-al)

INCHI for NP0335866 (3,7-Dihydroxy-25-methoxycucurbita-5,23-dien-19-al)

Structure for NP0335866 (3,7-Dihydroxy-25-methoxycucurbita-5,23-dien-19-al)

3D Structure for NP0335866 (3,7-Dihydroxy-25-methoxycucurbita-5,23-dien-19-al)