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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:36:25 UTC

Update Date

2022-03-07 02:52:31 UTC

HMDB ID

HMDB0030373

Secondary Accession Numbers

HMDB30373

Metabolite Identification

Common Name

Citrusinine II

Description

Citrusinine II 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. Citrusinine II is found, on average, in the highest concentration within sweet oranges (Citrus sinensis). Citrusinine II has also been detected, but not quantified in, citrus. This could make citrusinine II a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Citrusinine II.

Structure

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

HMDB0030373
     RDKit          3D
Citrusinine II
 34 36  0  0  0  0  0  0  0  0999 V2000
   -2.6440    1.4694    1.8368 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2825    1.7108    0.4506 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9885    0.5142   -0.2238 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1067   -0.1436   -0.7683 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3708    0.4226   -0.6207 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9140   -1.3113   -1.4209 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6024   -1.8299   -1.5330 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4727   -3.0077   -2.1980 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5258   -1.1810   -1.0015 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7610   -1.6668   -1.0655 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9973   -2.7563   -1.6600 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8390   -1.0175   -0.5037 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1168   -1.5736   -0.5677 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1884   -0.9396    0.0268 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9496    0.2453    0.6768 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6566    0.8087    0.7410 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5496    1.9901    1.4277 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6067    0.1656    0.1406 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3390    0.6868    0.2215 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.2113    2.0113    0.7278 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7175    0.0441   -0.3199 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7090    1.2160    1.8904 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0680    0.6421    2.2565 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3645    2.3880    2.3857 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1517   -0.0665   -1.0183 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7371   -1.8588   -1.8591 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7334   -3.5528   -2.4095 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2273   -2.5077   -1.0950 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1866   -1.3520   -0.0112 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8000    0.7332    1.1414 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3635    2.4031    1.8417 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1513    2.0132    1.8130 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6301    2.6311    0.3663 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0747    2.6693    0.3315 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
  4  6  1  0
  6  7  2  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 16 18  2  0
 18 19  1  0
 19 20  1  0
 19 21  1  0
 21  3  1  0
 21  9  2  0
 18 12  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  5 25  1  0
  6 26  1  0
  8 27  1  0
 13 28  1  0
 14 29  1  0
 15 30  1  0
 17 31  1  0
 20 32  1  0
 20 33  1  0
 20 34  1  0
M  END


  Mrv0541 05061305112D          

 21 23  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    3.7125    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
    5.0013    2.0625    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
    3.5724    1.2375    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    0.8250    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
    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
    1.4289    2.4750    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
    4.2868    3.3000    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
    0.0000    2.4750    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
    1.4289    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  2  0  0  0  0
  5  3  1  0  0  0  0
  7  4  1  0  0  0  0
  8  5  2  0  0  0  0
  9  6  2  0  0  0  0
 10  6  1  0  0  0  0
 11  9  1  0  0  0  0
 12  7  2  0  0  0  0
 12  8  1  0  0  0  0
 13 11  2  0  0  0  0
 14  7  1  0  0  0  0
 14 11  1  0  0  0  0
 15 10  2  0  0  0  0
 15 13  1  0  0  0  0
 16  1  1  0  0  0  0
 16 12  1  0  0  0  0
 16 13  1  0  0  0  0
 17  8  1  0  0  0  0
 18  9  1  0  0  0  0
 19 10  1  0  0  0  0
 20 14  2  0  0  0  0
 21  2  1  0  0  0  0
 21 15  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0030373

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=C(O)C=C(O)C2=C1N(C)C1=C(C=CC=C1O)C2=O

> <INCHI_IDENTIFIER>
InChI=1S/C15H13NO5/c1-16-12-7(4-3-5-8(12)17)14(20)11-9(18)6-10(19)15(21-2)13(11)16/h3-6,17-19H,1-2H3

> <INCHI_KEY>
QEGXAAUCDUFHPJ-UHFFFAOYSA-N

> <FORMULA>
C15H13NO5

> <MOLECULAR_WEIGHT>
287.2674

> <EXACT_MASS>
287.079372531

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
28.0426024730331

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1,3,5-trihydroxy-4-methoxy-10-methyl-9,10-dihydroacridin-9-one

> <ALOGPS_LOGP>
2.41

> <JCHEM_LOGP>
2.7045876476666666

> <ALOGPS_LOGS>
-2.59

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.251503857291349

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.471196740921185

> <JCHEM_PKA_STRONGEST_BASIC>
-4.071848175878

> <JCHEM_POLAR_SURFACE_AREA>
90.23

> <JCHEM_REFRACTIVITY>
76.36430000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.36e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1,3,5-trihydroxy-4-methoxy-10-methylacridin-9-one

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0030373
     RDKit          3D
Citrusinine II
 34 36  0  0  0  0  0  0  0  0999 V2000
   -2.6440    1.4694    1.8368 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2825    1.7108    0.4506 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9885    0.5142   -0.2238 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1067   -0.1436   -0.7683 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3708    0.4226   -0.6207 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9140   -1.3113   -1.4209 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6024   -1.8299   -1.5330 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4727   -3.0077   -2.1980 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5258   -1.1810   -1.0015 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7610   -1.6668   -1.0655 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9973   -2.7563   -1.6600 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8390   -1.0175   -0.5037 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1168   -1.5736   -0.5677 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1884   -0.9396    0.0268 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9496    0.2453    0.6768 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6566    0.8087    0.7410 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5496    1.9901    1.4277 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6067    0.1656    0.1406 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3390    0.6868    0.2215 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.2113    2.0113    0.7278 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7175    0.0441   -0.3199 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7090    1.2160    1.8904 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0680    0.6421    2.2565 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3645    2.3880    2.3857 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1517   -0.0665   -1.0183 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7371   -1.8588   -1.8591 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7334   -3.5528   -2.4095 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2273   -2.5077   -1.0950 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1866   -1.3520   -0.0112 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8000    0.7332    1.1414 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3635    2.4031    1.8417 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1513    2.0132    1.8130 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6301    2.6311    0.3663 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0747    2.6693    0.3315 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
  4  6  1  0
  6  7  2  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 16 18  2  0
 18 19  1  0
 19 20  1  0
 19 21  1  0
 21  3  1  0
 21  9  2  0
 18 12  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  5 25  1  0
  6 26  1  0
  8 27  1  0
 13 28  1  0
 14 29  1  0
 15 30  1  0
 17 31  1  0
 20 32  1  0
 20 33  1  0
 20 34  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   6.930   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       9.336   3.850   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.668   2.310   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   1.540   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.334   3.850   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  C   UNK     0       2.667   4.620   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       8.002   6.160   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       0.000   4.620   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       5.335   0.000   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       2.667   6.160   0.000  0.00  0.00           O+0
CONECT    1   16                                                            
CONECT    2   21                                                            
CONECT    3    4    5                                                       
CONECT    4    3    7                                                       
CONECT    5    3    8                                                       
CONECT    6    9   10                                                       
CONECT    7    4   12   14                                                  
CONECT    8    5   12   17                                                  
CONECT    9    6   11   18                                                  
CONECT   10    6   15   19                                                  
CONECT   11    9   13   14                                                  
CONECT   12    7    8   16                                                  
CONECT   13   11   15   16                                                  
CONECT   14    7   11   20                                                  
CONECT   15   10   13   21                                                  
CONECT   16    1   12   13                                                  
CONECT   17    8                                                            
CONECT   18    9                                                            
CONECT   19   10                                                            
CONECT   20   14                                                            
CONECT   21    2   15                                                       
MASTER        0    0    0    0    0    0    0    0   21    0   46    0
END

COMPND    HMDB0030373
HETATM    1  C1  UNL     1      -2.644   1.469   1.837  1.00  0.00           C  
HETATM    2  O1  UNL     1      -2.282   1.711   0.451  1.00  0.00           O  
HETATM    3  C2  UNL     1      -1.988   0.514  -0.224  1.00  0.00           C  
HETATM    4  C3  UNL     1      -3.107  -0.144  -0.768  1.00  0.00           C  
HETATM    5  O2  UNL     1      -4.371   0.423  -0.621  1.00  0.00           O  
HETATM    6  C4  UNL     1      -2.914  -1.311  -1.421  1.00  0.00           C  
HETATM    7  C5  UNL     1      -1.602  -1.830  -1.533  1.00  0.00           C  
HETATM    8  O3  UNL     1      -1.473  -3.008  -2.198  1.00  0.00           O  
HETATM    9  C6  UNL     1      -0.526  -1.181  -1.002  1.00  0.00           C  
HETATM   10  C7  UNL     1       0.761  -1.667  -1.065  1.00  0.00           C  
HETATM   11  O4  UNL     1       0.997  -2.756  -1.660  1.00  0.00           O  
HETATM   12  C8  UNL     1       1.839  -1.017  -0.504  1.00  0.00           C  
HETATM   13  C9  UNL     1       3.117  -1.574  -0.568  1.00  0.00           C  
HETATM   14  C10 UNL     1       4.188  -0.940   0.027  1.00  0.00           C  
HETATM   15  C11 UNL     1       3.950   0.245   0.677  1.00  0.00           C  
HETATM   16  C12 UNL     1       2.657   0.809   0.741  1.00  0.00           C  
HETATM   17  O5  UNL     1       2.550   1.990   1.428  1.00  0.00           O  
HETATM   18  C13 UNL     1       1.607   0.166   0.141  1.00  0.00           C  
HETATM   19  N1  UNL     1       0.339   0.687   0.222  1.00  0.00           N  
HETATM   20  C14 UNL     1       0.211   2.011   0.728  1.00  0.00           C  
HETATM   21  C15 UNL     1      -0.718   0.044  -0.320  1.00  0.00           C  
HETATM   22  H1  UNL     1      -3.709   1.216   1.890  1.00  0.00           H  
HETATM   23  H2  UNL     1      -2.068   0.642   2.257  1.00  0.00           H  
HETATM   24  H3  UNL     1      -2.365   2.388   2.386  1.00  0.00           H  
HETATM   25  H4  UNL     1      -5.152  -0.066  -1.018  1.00  0.00           H  
HETATM   26  H5  UNL     1      -3.737  -1.859  -1.859  1.00  0.00           H  
HETATM   27  H6  UNL     1      -0.733  -3.553  -2.409  1.00  0.00           H  
HETATM   28  H7  UNL     1       3.227  -2.508  -1.095  1.00  0.00           H  
HETATM   29  H8  UNL     1       5.187  -1.352  -0.011  1.00  0.00           H  
HETATM   30  H9  UNL     1       4.800   0.733   1.141  1.00  0.00           H  
HETATM   31  H10 UNL     1       3.363   2.403   1.842  1.00  0.00           H  
HETATM   32  H11 UNL     1       0.151   2.013   1.813  1.00  0.00           H  
HETATM   33  H12 UNL     1      -0.630   2.631   0.366  1.00  0.00           H  
HETATM   34  H13 UNL     1       1.075   2.669   0.332  1.00  0.00           H  
CONECT    1    2   22   23   24
CONECT    2    3
CONECT    3    4    4   21
CONECT    4    5    6
CONECT    5   25
CONECT    6    7    7   26
CONECT    7    8    9
CONECT    8   27
CONECT    9   10   21   21
CONECT   10   11   11   12
CONECT   12   13   13   18
CONECT   13   14   28
CONECT   14   15   15   29
CONECT   15   16   30
CONECT   16   17   18   18
CONECT   17   31
CONECT   18   19
CONECT   19   20   21
CONECT   20   32   33   34
END

HMDB0030373
     RDKit          3D
Citrusinine II
 34 36  0  0  0  0  0  0  0  0999 V2000
   -2.6440    1.4694    1.8368 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2825    1.7108    0.4506 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9885    0.5142   -0.2238 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1067   -0.1436   -0.7683 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3708    0.4226   -0.6207 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9140   -1.3113   -1.4209 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6024   -1.8299   -1.5330 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4727   -3.0077   -2.1980 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5258   -1.1810   -1.0015 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7610   -1.6668   -1.0655 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9973   -2.7563   -1.6600 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8390   -1.0175   -0.5037 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1168   -1.5736   -0.5677 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1884   -0.9396    0.0268 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9496    0.2453    0.6768 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6566    0.8087    0.7410 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5496    1.9901    1.4277 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6067    0.1656    0.1406 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3390    0.6868    0.2215 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.2113    2.0113    0.7278 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7175    0.0441   -0.3199 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7090    1.2160    1.8904 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0680    0.6421    2.2565 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3645    2.3880    2.3857 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1517   -0.0665   -1.0183 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7371   -1.8588   -1.8591 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7334   -3.5528   -2.4095 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2273   -2.5077   -1.0950 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1866   -1.3520   -0.0112 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8000    0.7332    1.1414 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3635    2.4031    1.8417 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1513    2.0132    1.8130 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6301    2.6311    0.3663 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0747    2.6693    0.3315 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
  4  6  1  0
  6  7  2  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 16 18  2  0
 18 19  1  0
 19 20  1  0
 19 21  1  0
 21  3  1  0
 21  9  2  0
 18 12  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  5 25  1  0
  6 26  1  0
  8 27  1  0
 13 28  1  0
 14 29  1  0
 15 30  1  0
 17 31  1  0
 20 32  1  0
 20 33  1  0
 20 34  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
1,3,5-Trihydroxy-4-methoxy-10-methylacridone	HMDB

Chemical Formula

C₁₅H₁₃NO₅

Average Molecular Weight

287.2674

Monoisotopic Molecular Weight

287.079372531

IUPAC Name

1,3,5-trihydroxy-4-methoxy-10-methyl-9,10-dihydroacridin-9-one

Traditional Name

1,3,5-trihydroxy-4-methoxy-10-methylacridin-9-one

CAS Registry Number

86680-33-3

SMILES

COC1=C(O)C=C(O)C2=C1N(C)C1=C(C=CC=C1O)C2=O

InChI Identifier

InChI=1S/C15H13NO5/c1-16-12-7(4-3-5-8(12)17)14(20)11-9(18)6-10(19)15(21-2)13(11)16/h3-6,17-19H,1-2H3

InChI Key

QEGXAAUCDUFHPJ-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
8-hydroxyquinoline
Dihydroquinoline
Anisole
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Pyridine
Benzenoid
Heteroaromatic compound
Vinylogous acid
Vinylogous amide
Polyol
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: HMDB0030373)
Cytoplasm (HMDB: HMDB0030373)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0030373)

Source

Endogenous

Endogenous (HMDB: HMDB0030373)

Plant

Plant (HMDB: HMDB0030373)

Exogenous

Food

Food (HMDB: HMDB0030373)

Fruit

Citrus

Sweet orange (FooDB: FOOD00057)
Citrus (FooDB: FOOD00859)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	244 - 246 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	145.4 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.74 g/L	ALOGPS
logP	2.41	ALOGPS
logP	2.7	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Acidic)	8.47	ChemAxon
pKa (Strongest Basic)	-4.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	90.23 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	76.36 m³·mol⁻¹	ChemAxon
Polarizability	28.04 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]+	164.42	31661259
DarkChem	[M-H]-	164.293	31661259
DeepCCS	[M+H]+	166.742	30932474
DeepCCS	[M-H]-	164.384	30932474
DeepCCS	[M-2H]-	197.344	30932474
DeepCCS	[M+Na]+	172.835	30932474
AllCCS	[M+H]+	163.6	32859911
AllCCS	[M+H-H2O]+	159.9	32859911
AllCCS	[M+NH4]+	167.1	32859911
AllCCS	[M+Na]+	168.1	32859911
AllCCS	[M-H]-	166.5	32859911
AllCCS	[M+Na-2H]-	165.8	32859911
AllCCS	[M+HCOO]-	165.2	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Citrusinine II	COC1=C(O)C=C(O)C2=C1N(C)C1=C(C=CC=C1O)C2=O	3651.3	Standard polar	33892256
Citrusinine II	COC1=C(O)C=C(O)C2=C1N(C)C1=C(C=CC=C1O)C2=O	2472.0	Standard non polar	33892256
Citrusinine II	COC1=C(O)C=C(O)C2=C1N(C)C1=C(C=CC=C1O)C2=O	2925.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Citrusinine II,1TMS,isomer #1	COC1=C(O[Si](C)(C)C)C=C(O)C2=C1N(C)C1=C(O)C=CC=C1C2=O	2897.1	Semi standard non polar	33892256
Citrusinine II,1TMS,isomer #2	COC1=C(O)C=C(O[Si](C)(C)C)C2=C1N(C)C1=C(O)C=CC=C1C2=O	2950.4	Semi standard non polar	33892256
Citrusinine II,1TMS,isomer #3	COC1=C(O)C=C(O)C2=C1N(C)C1=C(O[Si](C)(C)C)C=CC=C1C2=O	2959.4	Semi standard non polar	33892256
Citrusinine II,2TMS,isomer #1	COC1=C(O[Si](C)(C)C)C=C(O[Si](C)(C)C)C2=C1N(C)C1=C(O)C=CC=C1C2=O	2822.4	Semi standard non polar	33892256
Citrusinine II,2TMS,isomer #2	COC1=C(O[Si](C)(C)C)C=C(O)C2=C1N(C)C1=C(O[Si](C)(C)C)C=CC=C1C2=O	2840.9	Semi standard non polar	33892256
Citrusinine II,2TMS,isomer #3	COC1=C(O)C=C(O[Si](C)(C)C)C2=C1N(C)C1=C(O[Si](C)(C)C)C=CC=C1C2=O	2973.8	Semi standard non polar	33892256
Citrusinine II,3TMS,isomer #1	COC1=C(O[Si](C)(C)C)C=C(O[Si](C)(C)C)C2=C1N(C)C1=C(O[Si](C)(C)C)C=CC=C1C2=O	2890.4	Semi standard non polar	33892256
Citrusinine II,1TBDMS,isomer #1	COC1=C(O[Si](C)(C)C(C)(C)C)C=C(O)C2=C1N(C)C1=C(O)C=CC=C1C2=O	3109.5	Semi standard non polar	33892256
Citrusinine II,1TBDMS,isomer #2	COC1=C(O)C=C(O[Si](C)(C)C(C)(C)C)C2=C1N(C)C1=C(O)C=CC=C1C2=O	3161.3	Semi standard non polar	33892256
Citrusinine II,1TBDMS,isomer #3	COC1=C(O)C=C(O)C2=C1N(C)C1=C(O[Si](C)(C)C(C)(C)C)C=CC=C1C2=O	3158.1	Semi standard non polar	33892256
Citrusinine II,2TBDMS,isomer #1	COC1=C(O[Si](C)(C)C(C)(C)C)C=C(O[Si](C)(C)C(C)(C)C)C2=C1N(C)C1=C(O)C=CC=C1C2=O	3263.7	Semi standard non polar	33892256
Citrusinine II,2TBDMS,isomer #2	COC1=C(O[Si](C)(C)C(C)(C)C)C=C(O)C2=C1N(C)C1=C(O[Si](C)(C)C(C)(C)C)C=CC=C1C2=O	3270.5	Semi standard non polar	33892256
Citrusinine II,2TBDMS,isomer #3	COC1=C(O)C=C(O[Si](C)(C)C(C)(C)C)C2=C1N(C)C1=C(O[Si](C)(C)C(C)(C)C)C=CC=C1C2=O	3365.1	Semi standard non polar	33892256
Citrusinine II,3TBDMS,isomer #1	COC1=C(O[Si](C)(C)C(C)(C)C)C=C(O[Si](C)(C)C(C)(C)C)C2=C1N(C)C1=C(O[Si](C)(C)C(C)(C)C)C=CC=C1C2=O	3496.7	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 - Citrusinine II GC-MS (Non-derivatized) - 70eV, Positive	splash10-0abc-0390000000-e73af68e7ef916cf1cae	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Citrusinine II GC-MS (3 TMS) - 70eV, Positive	splash10-0019-2101900000-19efd88a6e242dd31003	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Citrusinine II 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 - Citrusinine II 10V, Positive-QTOF	splash10-000i-0090000000-ae2fde22c567d6930e87	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Citrusinine II 20V, Positive-QTOF	splash10-000i-0090000000-98138ff58f36568aacf9	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Citrusinine II 40V, Positive-QTOF	splash10-00r2-1190000000-5d0f98e3e3bb87f011e7	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Citrusinine II 10V, Negative-QTOF	splash10-000i-0090000000-c641dd7336509b4563a8	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Citrusinine II 20V, Negative-QTOF	splash10-000i-0090000000-6e358e87d29ff301303b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Citrusinine II 40V, Negative-QTOF	splash10-0fk9-0090000000-c6167a35bf1294069c0d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Citrusinine II 10V, Positive-QTOF	splash10-000i-0090000000-653c66c5e9bde424725f	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Citrusinine II 20V, Positive-QTOF	splash10-000i-0090000000-653c66c5e9bde424725f	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Citrusinine II 40V, Positive-QTOF	splash10-00di-0390000000-4cc745526c195d8a37db	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Citrusinine II 10V, Negative-QTOF	splash10-000i-0090000000-b223092e1b230e39e4b1	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Citrusinine II 20V, Negative-QTOF	splash10-000i-0090000000-6177069510e3100d5d8a	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Citrusinine II 40V, Negative-QTOF	splash10-052f-0290000000-618c155c1577a1059efc	2021-09-22	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

FDB002222

KNApSAcK ID

C00024250

Chemspider ID

8192468

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10016895

PDB ID

Not Available

ChEBI ID

565534

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1819391

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 Citrusinine II (HMDB0030373)

MOL for HMDB0030373 (Citrusinine II)

3D MOL for HMDB0030373 (Citrusinine II)

3D SDF for HMDB0030373 (Citrusinine II)

3D-SDF for HMDB0030373 (Citrusinine II)

PDB for HMDB0030373 (Citrusinine II)

3D PDB for HMDB0030373 (Citrusinine II)

SMILES for HMDB0030373 (Citrusinine II)

INCHI for HMDB0030373 (Citrusinine II)

Structure for HMDB0030373 (Citrusinine II)

3D Structure for HMDB0030373 (Citrusinine II)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra