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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-12 01:54:38 UTC

Update Date

2022-03-07 02:56:34 UTC

HMDB ID

HMDB0040382

Secondary Accession Numbers

HMDB40382

Metabolite Identification

Common Name

Pummeline

Description

Pummeline 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. Pummeline has been detected, but not quantified in, citrus. This could make pummeline a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Pummeline.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HMDB0040382
     RDKit          3D
Pummeline
 33 35  0  0  0  0  0  0  0  0999 V2000
    5.2366   -0.1441    0.7096 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9746   -0.1327    1.3169 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8378   -0.0760    0.5246 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9282   -0.0309   -0.8479 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7851    0.0252   -1.6136 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7999    0.0729   -2.9917 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5634    0.0328   -0.9295 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5807    0.1016   -1.7097 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5019    0.1434   -2.9679 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7755    0.1212   -1.0534 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9305    0.2006   -1.8147 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1621    0.2339   -1.2075 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2932    0.1912    0.1449 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5276    0.2235    0.7981 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1357    0.1111    0.9151 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8879    0.0749    0.3341 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7454    0.0068    1.0466 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7968   -0.0854    2.4814 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4682   -0.0129    0.4425 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6207   -0.0676    1.1862 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3151    0.7032   -0.0271 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3734   -1.0735    0.0977 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0566   -0.0062    1.4300 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8962   -0.0392   -1.3327 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7037    0.0656   -3.4524 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8556    0.2360   -2.8866 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0824    0.2965   -1.8026 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0139   -0.6477    1.0026 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2410    0.0914    1.9710 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0291   -0.7917    2.9090 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7488   -0.6305    2.7702 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8115    0.8956    2.9618 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5601   -0.0892    2.2531 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  1  0
  5  7  2  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 13 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 17 19  1  0
 19 20  2  0
 20  3  1  0
 19  7  1  0
 16 10  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  4 24  1  0
  6 25  1  0
 11 26  1  0
 12 27  1  0
 14 28  1  0
 15 29  1  0
 18 30  1  0
 18 31  1  0
 18 32  1  0
 20 33  1  0
M  END


  Mrv0541 05061311482D          

 20 22  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
   -0.7145    2.0625    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
    4.2868    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
    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
    3.5724    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
    1.4289    0.8250    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
    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
    5.7158    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 O   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
    0.0000    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  2  0  0  0  0
  8  3  1  0  0  0  0
  8  5  2  0  0  0  0
  9  6  2  0  0  0  0
  9  7  1  0  0  0  0
 10  4  1  0  0  0  0
 11  5  1  0  0  0  0
 11 10  2  0  0  0  0
 12  6  1  0  0  0  0
 13  7  2  0  0  0  0
 14 12  2  0  0  0  0
 14 13  1  0  0  0  0
 15 10  1  0  0  0  0
 15 14  1  0  0  0  0
 16  1  1  0  0  0  0
 16 11  1  0  0  0  0
 16 12  1  0  0  0  0
 17  8  1  0  0  0  0
 18 13  1  0  0  0  0
 19 15  2  0  0  0  0
 20  2  1  0  0  0  0
 20  9  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0040382

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=CC2=C(C(O)=C1)C(=O)C1=C(C=C(O)C=C1)N2C

> <INCHI_IDENTIFIER>
InChI=1S/C15H13NO4/c1-16-11-5-8(17)3-4-10(11)15(19)14-12(16)6-9(20-2)7-13(14)18/h3-7,17-18H,1-2H3

> <INCHI_KEY>
ULFQWNWPHHCZAJ-UHFFFAOYSA-N

> <FORMULA>
C15H13NO4

> <MOLECULAR_WEIGHT>
271.268

> <EXACT_MASS>
271.084457909

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
27.75257699261755

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1,6-dihydroxy-3-methoxy-10-methyl-9,10-dihydroacridin-9-one

> <ALOGPS_LOGP>
2.34

> <JCHEM_LOGP>
3.0081529693333326

> <ALOGPS_LOGS>
-2.68

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
10.09404454582966

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.936436893414726

> <JCHEM_PKA_STRONGEST_BASIC>
-2.2383775039310247

> <JCHEM_POLAR_SURFACE_AREA>
70

> <JCHEM_REFRACTIVITY>
74.38340000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.67e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1,6-dihydroxy-3-methoxy-10-methylacridin-9-one

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0040382
     RDKit          3D
Pummeline
 33 35  0  0  0  0  0  0  0  0999 V2000
    5.2366   -0.1441    0.7096 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9746   -0.1327    1.3169 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8378   -0.0760    0.5246 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9282   -0.0309   -0.8479 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7851    0.0252   -1.6136 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7999    0.0729   -2.9917 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5634    0.0328   -0.9295 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5807    0.1016   -1.7097 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5019    0.1434   -2.9679 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7755    0.1212   -1.0534 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9305    0.2006   -1.8147 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1621    0.2339   -1.2075 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2932    0.1912    0.1449 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5276    0.2235    0.7981 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1357    0.1111    0.9151 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8879    0.0749    0.3341 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7454    0.0068    1.0466 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7968   -0.0854    2.4814 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4682   -0.0129    0.4425 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6207   -0.0676    1.1862 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3151    0.7032   -0.0271 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3734   -1.0735    0.0977 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0566   -0.0062    1.4300 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8962   -0.0392   -1.3327 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7037    0.0656   -3.4524 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8556    0.2360   -2.8866 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0824    0.2965   -1.8026 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0139   -0.6477    1.0026 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2410    0.0914    1.9710 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0291   -0.7917    2.9090 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7488   -0.6305    2.7702 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8115    0.8956    2.9618 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5601   -0.0892    2.2531 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  1  0
  5  7  2  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 13 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 17 19  1  0
 19 20  2  0
 20  3  1  0
 19  7  1  0
 16 10  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  4 24  1  0
  6 25  1  0
 11 26  1  0
 12 27  1  0
 14 28  1  0
 15 29  1  0
 18 30  1  0
 18 31  1  0
 18 32  1  0
 20 33  1  0
M  END

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      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       9.336   2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.002   4.620   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.336   3.850   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.334   3.850   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       6.668   3.850   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   16  N   UNK     0       5.335   4.620   0.000  0.00  0.00           N+0
HETATM   17  O   UNK     0      10.669   4.620   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       2.667   0.000   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       5.335   0.000   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       0.000   4.620   0.000  0.00  0.00           O+0
CONECT    1   16                                                            
CONECT    2   20                                                            
CONECT    3    4    8                                                       
CONECT    4    3   10                                                       
CONECT    5    8   11                                                       
CONECT    6    9   12                                                       
CONECT    7    9   13                                                       
CONECT    8    3    5   17                                                  
CONECT    9    6    7   20                                                  
CONECT   10    4   11   15                                                  
CONECT   11    5   10   16                                                  
CONECT   12    6   14   16                                                  
CONECT   13    7   14   18                                                  
CONECT   14   12   13   15                                                  
CONECT   15   10   14   19                                                  
CONECT   16    1   11   12                                                  
CONECT   17    8                                                            
CONECT   18   13                                                            
CONECT   19   15                                                            
CONECT   20    2    9                                                       
MASTER        0    0    0    0    0    0    0    0   20    0   44    0
END

COMPND    HMDB0040382
HETATM    1  C1  UNL     1       5.237  -0.144   0.710  1.00  0.00           C  
HETATM    2  O1  UNL     1       3.975  -0.133   1.317  1.00  0.00           O  
HETATM    3  C2  UNL     1       2.838  -0.076   0.525  1.00  0.00           C  
HETATM    4  C3  UNL     1       2.928  -0.031  -0.848  1.00  0.00           C  
HETATM    5  C4  UNL     1       1.785   0.025  -1.614  1.00  0.00           C  
HETATM    6  O2  UNL     1       1.800   0.073  -2.992  1.00  0.00           O  
HETATM    7  C5  UNL     1       0.563   0.033  -0.930  1.00  0.00           C  
HETATM    8  C6  UNL     1      -0.581   0.102  -1.710  1.00  0.00           C  
HETATM    9  O3  UNL     1      -0.502   0.143  -2.968  1.00  0.00           O  
HETATM   10  C7  UNL     1      -1.775   0.121  -1.053  1.00  0.00           C  
HETATM   11  C8  UNL     1      -2.930   0.201  -1.815  1.00  0.00           C  
HETATM   12  C9  UNL     1      -4.162   0.234  -1.207  1.00  0.00           C  
HETATM   13  C10 UNL     1      -4.293   0.191   0.145  1.00  0.00           C  
HETATM   14  O4  UNL     1      -5.528   0.223   0.798  1.00  0.00           O  
HETATM   15  C11 UNL     1      -3.136   0.111   0.915  1.00  0.00           C  
HETATM   16  C12 UNL     1      -1.888   0.075   0.334  1.00  0.00           C  
HETATM   17  N1  UNL     1      -0.745   0.007   1.047  1.00  0.00           N  
HETATM   18  C13 UNL     1      -0.797  -0.085   2.481  1.00  0.00           C  
HETATM   19  C14 UNL     1       0.468  -0.013   0.443  1.00  0.00           C  
HETATM   20  C15 UNL     1       1.621  -0.068   1.186  1.00  0.00           C  
HETATM   21  H1  UNL     1       5.315   0.703  -0.027  1.00  0.00           H  
HETATM   22  H2  UNL     1       5.373  -1.074   0.098  1.00  0.00           H  
HETATM   23  H3  UNL     1       6.057  -0.006   1.430  1.00  0.00           H  
HETATM   24  H4  UNL     1       3.896  -0.039  -1.333  1.00  0.00           H  
HETATM   25  H5  UNL     1       2.704   0.066  -3.452  1.00  0.00           H  
HETATM   26  H6  UNL     1      -2.856   0.236  -2.887  1.00  0.00           H  
HETATM   27  H7  UNL     1      -5.082   0.297  -1.803  1.00  0.00           H  
HETATM   28  H8  UNL     1      -6.014  -0.648   1.003  1.00  0.00           H  
HETATM   29  H9  UNL     1      -3.241   0.091   1.971  1.00  0.00           H  
HETATM   30  H10 UNL     1      -0.029  -0.792   2.909  1.00  0.00           H  
HETATM   31  H11 UNL     1      -1.749  -0.630   2.770  1.00  0.00           H  
HETATM   32  H12 UNL     1      -0.812   0.896   2.962  1.00  0.00           H  
HETATM   33  H13 UNL     1       1.560  -0.089   2.253  1.00  0.00           H  
CONECT    1    2   21   22   23
CONECT    2    3
CONECT    3    4    4   20
CONECT    4    5   24
CONECT    5    6    7    7
CONECT    6   25
CONECT    7    8   19
CONECT    8    9    9   10
CONECT   10   11   11   16
CONECT   11   12   26
CONECT   12   13   13   27
CONECT   13   14   15
CONECT   14   28
CONECT   15   16   16   29
CONECT   16   17
CONECT   17   18   19
CONECT   18   30   31   32
CONECT   19   20   20
CONECT   20   33
END

HMDB0040382
     RDKit          3D
Pummeline
 33 35  0  0  0  0  0  0  0  0999 V2000
    5.2366   -0.1441    0.7096 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9746   -0.1327    1.3169 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8378   -0.0760    0.5246 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9282   -0.0309   -0.8479 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7851    0.0252   -1.6136 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7999    0.0729   -2.9917 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5634    0.0328   -0.9295 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5807    0.1016   -1.7097 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5019    0.1434   -2.9679 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7755    0.1212   -1.0534 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9305    0.2006   -1.8147 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1621    0.2339   -1.2075 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2932    0.1912    0.1449 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5276    0.2235    0.7981 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1357    0.1111    0.9151 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8879    0.0749    0.3341 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7454    0.0068    1.0466 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7968   -0.0854    2.4814 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4682   -0.0129    0.4425 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6207   -0.0676    1.1862 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3151    0.7032   -0.0271 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3734   -1.0735    0.0977 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0566   -0.0062    1.4300 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8962   -0.0392   -1.3327 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7037    0.0656   -3.4524 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8556    0.2360   -2.8866 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0824    0.2965   -1.8026 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0139   -0.6477    1.0026 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2410    0.0914    1.9710 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0291   -0.7917    2.9090 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7488   -0.6305    2.7702 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8115    0.8956    2.9618 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5601   -0.0892    2.2531 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  1  0
  5  7  2  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 13 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 17 19  1  0
 19 20  2  0
 20  3  1  0
 19  7  1  0
 16 10  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  4 24  1  0
  6 25  1  0
 11 26  1  0
 12 27  1  0
 14 28  1  0
 15 29  1  0
 18 30  1  0
 18 31  1  0
 18 32  1  0
 20 33  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
1,6-Dihydroxy-3-methoxy-10-methylacridone	HMDB

Chemical Formula

C₁₅H₁₃NO₄

Average Molecular Weight

271.268

Monoisotopic Molecular Weight

271.084457909

IUPAC Name

1,6-dihydroxy-3-methoxy-10-methyl-9,10-dihydroacridin-9-one

Traditional Name

1,6-dihydroxy-3-methoxy-10-methylacridin-9-one

CAS Registry Number

145940-36-9

SMILES

COC1=CC2=C(C(O)=C1)C(=O)C1=C(C=C(O)C=C1)N2C

InChI Identifier

InChI=1S/C15H13NO4/c1-16-11-5-8(17)3-4-10(11)15(19)14-12(16)6-9(20-2)7-13(14)18/h3-7,17-18H,1-2H3

InChI Key

ULFQWNWPHHCZAJ-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.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Quinolines and derivatives

Sub Class

Benzoquinolines

Direct Parent

Acridones

Alternative Parents

Substituents

Acridone
Dihydroquinolone
Dihydroquinoline
Anisole
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Pyridine
Benzenoid
Heteroaromatic compound
Vinylogous acid
Vinylogous amide
Ether
Azacycle
Organic nitrogen compound
Organooxygen compound
Organonitrogen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Organopnictogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0040382)
Cytoplasm (HMDB: HMDB0040382)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0040382)

Source

Exogenous

Exogenous (HMDB: HMDB0040382)

Food

Food (HMDB: HMDB0040382)

Fruit

Citrus

Citrus (FooDB: FOOD00859)

Endogenous

Plant

Plant (HMDB: HMDB0040382)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0040382)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	235 - 240 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.57 g/L	ALOGPS
logP	2.34	ALOGPS
logP	3.01	ChemAxon
logS	-2.7	ALOGPS
pKa (Strongest Acidic)	7.94	ChemAxon
pKa (Strongest Basic)	-2.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	70 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	74.38 m³·mol⁻¹	ChemAxon
Polarizability	27.75 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	164.142	31661259
DarkChem	[M-H]-	165.558	31661259
DeepCCS	[M+H]+	165.147	30932474
DeepCCS	[M-H]-	162.789	30932474
DeepCCS	[M-2H]-	196.774	30932474
DeepCCS	[M+Na]+	171.951	30932474
AllCCS	[M+H]+	160.5	32859911
AllCCS	[M+H-H2O]+	156.6	32859911
AllCCS	[M+NH4]+	164.0	32859911
AllCCS	[M+Na]+	165.1	32859911
AllCCS	[M-H]-	164.3	32859911
AllCCS	[M+Na-2H]-	163.6	32859911
AllCCS	[M+HCOO]-	163.1	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Pummeline	COC1=CC2=C(C(O)=C1)C(=O)C1=C(C=C(O)C=C1)N2C	3675.7	Standard polar	33892256
Pummeline	COC1=CC2=C(C(O)=C1)C(=O)C1=C(C=C(O)C=C1)N2C	2345.8	Standard non polar	33892256
Pummeline	COC1=CC2=C(C(O)=C1)C(=O)C1=C(C=C(O)C=C1)N2C	3255.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Pummeline,1TMS,isomer #1	COC1=CC(O[Si](C)(C)C)=C2C(=O)C3=CC=C(O)C=C3N(C)C2=C1	2895.6	Semi standard non polar	33892256
Pummeline,1TMS,isomer #2	COC1=CC(O)=C2C(=O)C3=CC=C(O[Si](C)(C)C)C=C3N(C)C2=C1	2954.0	Semi standard non polar	33892256
Pummeline,2TMS,isomer #1	COC1=CC(O[Si](C)(C)C)=C2C(=O)C3=CC=C(O[Si](C)(C)C)C=C3N(C)C2=C1	2938.8	Semi standard non polar	33892256
Pummeline,1TBDMS,isomer #1	COC1=CC(O[Si](C)(C)C(C)(C)C)=C2C(=O)C3=CC=C(O)C=C3N(C)C2=C1	3117.4	Semi standard non polar	33892256
Pummeline,1TBDMS,isomer #2	COC1=CC(O)=C2C(=O)C3=CC=C(O[Si](C)(C)C(C)(C)C)C=C3N(C)C2=C1	3184.1	Semi standard non polar	33892256
Pummeline,2TBDMS,isomer #1	COC1=CC(O[Si](C)(C)C(C)(C)C)=C2C(=O)C3=CC=C(O[Si](C)(C)C(C)(C)C)C=C3N(C)C2=C1	3340.4	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Pummeline GC-MS (Non-derivatized) - 70eV, Positive	splash10-052f-0290000000-3717f4b6fc11e0cc6d73	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Pummeline GC-MS (2 TMS) - 70eV, Positive	splash10-0ukc-2039400000-d1b6b515c1bd9171952d	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Pummeline GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pummeline 10V, Positive-QTOF	splash10-00di-0090000000-eca309b0f1b261cc6cbb	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pummeline 20V, Positive-QTOF	splash10-00di-0090000000-733afcdb58288ea42308	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pummeline 40V, Positive-QTOF	splash10-03kc-0390000000-e8128418c4442c18c96e	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pummeline 10V, Negative-QTOF	splash10-00di-0090000000-e81356d1bfb10df2e7ec	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pummeline 20V, Negative-QTOF	splash10-00di-0090000000-85da2b1af04f0fa47ec5	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pummeline 40V, Negative-QTOF	splash10-0103-2490000000-6d5d1a77829dfe886f13	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pummeline 10V, Negative-QTOF	splash10-00di-0090000000-2e11bb63e0942d2d8a1c	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pummeline 20V, Negative-QTOF	splash10-00di-0090000000-2e11bb63e0942d2d8a1c	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pummeline 40V, Negative-QTOF	splash10-006x-2980000000-396178f448edd7dee957	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pummeline 10V, Positive-QTOF	splash10-00di-0090000000-d75dd06255504b226484	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pummeline 20V, Positive-QTOF	splash10-00di-0090000000-d75dd06255504b226484	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pummeline 40V, Positive-QTOF	splash10-00di-0890000000-aef8ab2e11ed43b96904	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB020114

KNApSAcK ID

C00052396

Chemspider ID

8643819

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10468408

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for Pummeline (HMDB0040382)

MOL for HMDB0040382 (Pummeline)

3D MOL for HMDB0040382 (Pummeline)

3D SDF for HMDB0040382 (Pummeline)

3D-SDF for HMDB0040382 (Pummeline)

PDB for HMDB0040382 (Pummeline)

3D PDB for HMDB0040382 (Pummeline)

SMILES for HMDB0040382 (Pummeline)

INCHI for HMDB0040382 (Pummeline)

Structure for HMDB0040382 (Pummeline)

3D Structure for HMDB0040382 (Pummeline)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra