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Showing metabocard for 10-Methylacridone (HMDB0033000)

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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:53:10 UTC
Update Date2023-02-21 17:22:57 UTC
HMDB IDHMDB0033000
Secondary Accession Numbers
  • HMDB33000
Metabolite Identification
Common Name10-Methylacridone
Description10-Methylacridone belongs to the class of organic compounds known as acridones. These are acridines containing a ketone group attached to the C9 carbon atom of the acridine moiety. 10-Methylacridone has been detected, but not quantified in, citrus. This could make 10-methylacridone a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on 10-Methylacridone.
Structure
Data?1677000177
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0033000 (10-Methylacridone)

  Mrv0541 05061306512D          

 16 18  0  0  0  0            999 V2000
    2.8579    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    2.0625    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
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 C   0  0  0  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
    3.5724    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    2.4750    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  2  2  0  0  0  0
  5  3  2  0  0  0  0
  6  2  1  0  0  0  0
  7  3  1  0  0  0  0
  8  4  1  0  0  0  0
  9  5  1  0  0  0  0
 10  6  2  0  0  0  0
 11  7  2  0  0  0  0
 12  8  2  0  0  0  0
 12 10  1  0  0  0  0
 13  9  2  0  0  0  0
 13 11  1  0  0  0  0
 14 10  1  0  0  0  0
 14 11  1  0  0  0  0
 15  1  1  0  0  0  0
 15 12  1  0  0  0  0
 15 13  1  0  0  0  0
 16 14  2  0  0  0  0
M  END
Download

3D MOL for HMDB0033000 (10-Methylacridone)

HMDB0033000
     RDKit          3D
10-Methylacridone
 27 29  0  0  0  0  0  0  0  0999 V2000
    0.1525    2.4337    0.1885 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0203    1.0381    0.0742 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1276    0.2865    0.0302 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3686    0.8903    0.0873 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5506    0.1452    0.0424 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5363   -1.2205   -0.0607 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3039   -1.8245   -0.1180 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1125   -1.0866   -0.0737 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0878   -1.7535   -0.1376 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1133   -3.0078   -0.2325 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2460   -1.0103   -0.0948 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4871   -1.6079   -0.1558 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6613   -0.8921   -0.1171 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6070    0.4751   -0.0134 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3456    1.0926    0.0495 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1825    0.3753    0.0107 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7975    2.7706   -0.6763 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6669    3.0947    0.3809 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8079    2.6043    1.1028 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4092    1.9647    0.1660 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4834    0.6777    0.0914 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4638   -1.7735   -0.0935 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2658   -2.8960   -0.1991 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5357   -2.6842   -0.2375 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6376   -1.3518   -0.1643 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4868    1.1112    0.0231 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3018    2.1487    0.1273 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16  2  1  0
  8  3  1  0
 16 11  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  4 20  1  0
  5 21  1  0
  6 22  1  0
  7 23  1  0
 12 24  1  0
 13 25  1  0
 14 26  1  0
 15 27  1  0
M  END
Download

3D SDF for HMDB0033000 (10-Methylacridone)

  Mrv0541 05061306512D          

 16 18  0  0  0  0            999 V2000
    2.8579    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    2.0625    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
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 C   0  0  0  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
    3.5724    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    2.4750    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  2  2  0  0  0  0
  5  3  2  0  0  0  0
  6  2  1  0  0  0  0
  7  3  1  0  0  0  0
  8  4  1  0  0  0  0
  9  5  1  0  0  0  0
 10  6  2  0  0  0  0
 11  7  2  0  0  0  0
 12  8  2  0  0  0  0
 12 10  1  0  0  0  0
 13  9  2  0  0  0  0
 13 11  1  0  0  0  0
 14 10  1  0  0  0  0
 14 11  1  0  0  0  0
 15  1  1  0  0  0  0
 15 12  1  0  0  0  0
 15 13  1  0  0  0  0
 16 14  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0033000

> <DATABASE_NAME>
hmdb

> <SMILES>
CN1C2=CC=CC=C2C(=O)C2=CC=CC=C12

> <INCHI_IDENTIFIER>
InChI=1S/C14H11NO/c1-15-12-8-4-2-6-10(12)14(16)11-7-3-5-9-13(11)15/h2-9H,1H3

> <INCHI_KEY>
XUVKSPPGPPFPQN-UHFFFAOYSA-N

> <FORMULA>
C14H11NO

> <MOLECULAR_WEIGHT>
209.2432

> <EXACT_MASS>
209.084063979

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
22.741302818825268

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
10-methyl-9,10-dihydroacridin-9-one

> <ALOGPS_LOGP>
2.92

> <JCHEM_LOGP>
3.122954878333333

> <ALOGPS_LOGS>
-2.54

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
0.18964909881743686

> <JCHEM_POLAR_SURFACE_AREA>
20.310000000000002

> <JCHEM_REFRACTIVITY>
63.95840000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.02e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
10-methylacridin-9-one

> <JCHEM_VEBER_RULE>
1

$$$$
Download

3D-SDF for HMDB0033000 (10-Methylacridone)

HMDB0033000
     RDKit          3D
10-Methylacridone
 27 29  0  0  0  0  0  0  0  0999 V2000
    0.1525    2.4337    0.1885 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0203    1.0381    0.0742 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1276    0.2865    0.0302 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3686    0.8903    0.0873 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5506    0.1452    0.0424 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5363   -1.2205   -0.0607 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3039   -1.8245   -0.1180 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1125   -1.0866   -0.0737 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0878   -1.7535   -0.1376 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1133   -3.0078   -0.2325 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2460   -1.0103   -0.0948 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4871   -1.6079   -0.1558 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6613   -0.8921   -0.1171 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6070    0.4751   -0.0134 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3456    1.0926    0.0495 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1825    0.3753    0.0107 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7975    2.7706   -0.6763 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6669    3.0947    0.3809 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8079    2.6043    1.1028 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4092    1.9647    0.1660 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4834    0.6777    0.0914 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4638   -1.7735   -0.0935 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2658   -2.8960   -0.1991 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5357   -2.6842   -0.2375 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6376   -1.3518   -0.1643 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4868    1.1112    0.0231 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3018    2.1487    0.1273 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16  2  1  0
  8  3  1  0
 16 11  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  4 20  1  0
  5 21  1  0
  6 22  1  0
  7 23  1  0
 12 24  1  0
 13 25  1  0
 14 26  1  0
 15 27  1  0
M  END
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PDB for HMDB0033000 (10-Methylacridone)

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       5.335   6.160   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.336   2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.336   3.850   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.002   4.620   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.668   3.850   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   15  N   UNK     0       5.335   4.620   0.000  0.00  0.00           N+0
HETATM   16  O   UNK     0       5.335   0.000   0.000  0.00  0.00           O+0
CONECT    1   15                                                            
CONECT    2    4    6                                                       
CONECT    3    5    7                                                       
CONECT    4    2    8                                                       
CONECT    5    3    9                                                       
CONECT    6    2   10                                                       
CONECT    7    3   11                                                       
CONECT    8    4   12                                                       
CONECT    9    5   13                                                       
CONECT   10    6   12   14                                                  
CONECT   11    7   13   14                                                  
CONECT   12    8   10   15                                                  
CONECT   13    9   11   15                                                  
CONECT   14   10   11   16                                                  
CONECT   15    1   12   13                                                  
CONECT   16   14                                                            
MASTER        0    0    0    0    0    0    0    0   16    0   36    0
END
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3D PDB for HMDB0033000 (10-Methylacridone)

COMPND    HMDB0033000
HETATM    1  C1  UNL     1       0.153   2.434   0.189  1.00  0.00           C  
HETATM    2  N1  UNL     1      -0.020   1.038   0.074  1.00  0.00           N  
HETATM    3  C2  UNL     1       1.128   0.287   0.030  1.00  0.00           C  
HETATM    4  C3  UNL     1       2.369   0.890   0.087  1.00  0.00           C  
HETATM    5  C4  UNL     1       3.551   0.145   0.042  1.00  0.00           C  
HETATM    6  C5  UNL     1       3.536  -1.221  -0.061  1.00  0.00           C  
HETATM    7  C6  UNL     1       2.304  -1.825  -0.118  1.00  0.00           C  
HETATM    8  C7  UNL     1       1.112  -1.087  -0.074  1.00  0.00           C  
HETATM    9  C8  UNL     1      -0.088  -1.753  -0.138  1.00  0.00           C  
HETATM   10  O1  UNL     1      -0.113  -3.008  -0.233  1.00  0.00           O  
HETATM   11  C9  UNL     1      -1.246  -1.010  -0.095  1.00  0.00           C  
HETATM   12  C10 UNL     1      -2.487  -1.608  -0.156  1.00  0.00           C  
HETATM   13  C11 UNL     1      -3.661  -0.892  -0.117  1.00  0.00           C  
HETATM   14  C12 UNL     1      -3.607   0.475  -0.013  1.00  0.00           C  
HETATM   15  C13 UNL     1      -2.346   1.093   0.049  1.00  0.00           C  
HETATM   16  C14 UNL     1      -1.183   0.375   0.011  1.00  0.00           C  
HETATM   17  H1  UNL     1       0.798   2.771  -0.676  1.00  0.00           H  
HETATM   18  H2  UNL     1      -0.667   3.095   0.381  1.00  0.00           H  
HETATM   19  H3  UNL     1       0.808   2.604   1.103  1.00  0.00           H  
HETATM   20  H4  UNL     1       2.409   1.965   0.166  1.00  0.00           H  
HETATM   21  H5  UNL     1       4.483   0.678   0.091  1.00  0.00           H  
HETATM   22  H6  UNL     1       4.464  -1.773  -0.093  1.00  0.00           H  
HETATM   23  H7  UNL     1       2.266  -2.896  -0.199  1.00  0.00           H  
HETATM   24  H8  UNL     1      -2.536  -2.684  -0.238  1.00  0.00           H  
HETATM   25  H9  UNL     1      -4.638  -1.352  -0.164  1.00  0.00           H  
HETATM   26  H10 UNL     1      -4.487   1.111   0.023  1.00  0.00           H  
HETATM   27  H11 UNL     1      -2.302   2.149   0.127  1.00  0.00           H  
CONECT    1    2   17   18   19
CONECT    2    3   16
CONECT    3    4    4    8
CONECT    4    5   20
CONECT    5    6    6   21
CONECT    6    7   22
CONECT    7    8    8   23
CONECT    8    9
CONECT    9   10   10   11
CONECT   11   12   12   16
CONECT   12   13   24
CONECT   13   14   14   25
CONECT   14   15   26
CONECT   15   16   16   27
END
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SMILES for HMDB0033000 (10-Methylacridone)

CN1C2=CC=CC=C2C(=O)C2=CC=CC=C12
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INCHI for HMDB0033000 (10-Methylacridone)

InChI=1S/C14H11NO/c1-15-12-8-4-2-6-10(12)14(16)11-7-3-5-9-13(11)15/h2-9H,1H3
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Synonyms
ValueSource
10-Methyl-9(10H)-acridinoneHMDB
10-Methyl-9(10H)-acridinone, 9ciHMDB
10-Methyl-9(10H)-acridoneHMDB
10-Methyl-9-acridanoneHMDB
10-Methyl-9-acridanone, 8ciHMDB
10-Methylacridin-9(10H)-oneHMDB
10-MethylacridonHMDB
9(10H)-Acridinone, 10-methyl- (9ci)HMDB
9-Acridanone, 10-methyl- (8ci)HMDB
N-Methyl-9-acridoneHMDB
N-Methyl-acridoneHMDB
N-MethylacridoneHMDB
Chemical FormulaC14H11NO
Average Molecular Weight209.2432
Monoisotopic Molecular Weight209.084063979
IUPAC Name10-methyl-9,10-dihydroacridin-9-one
Traditional Name10-methylacridin-9-one
CAS Registry Number719-54-0
SMILES
CN1C2=CC=CC=C2C(=O)C2=CC=CC=C12
InChI Identifier
InChI=1S/C14H11NO/c1-15-12-8-4-2-6-10(12)14(16)11-7-3-5-9-13(11)15/h2-9H,1H3
InChI KeyXUVKSPPGPPFPQN-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as acridones. These are acridines containing a ketone group attached to the C9 carbon atom of the acridine moiety.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassQuinolines and derivatives
Sub ClassBenzoquinolines
Direct ParentAcridones
Alternative Parents
Substituents
  • Acridone
  • Dihydroquinolone
  • Dihydroquinoline
  • Pyridine
  • Benzenoid
  • Heteroaromatic compound
  • Vinylogous amide
  • Azacycle
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organooxygen compound
  • Organonitrogen compound
  • Organopnictogen compound
  • Organic oxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
Biological locationRoute of exposureSource
ProcessNot Available
Role
Biological role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point199 - 200 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility37.75 mg/L @ 25 °C (est)The Good Scents Company Information System
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular Locations
  • Membrane
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB010989
KNApSAcK IDC00052396
Chemspider ID62950
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound69751
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1157071
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .