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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

HMDB0030374

Secondary Accession Numbers

HMDB30374

Metabolite Identification

Common Name

Citrusinine I

Description

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

Structure

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

HMDB0030374
     RDKit          3D
Citrusinine I
 37 39  0  0  0  0  0  0  0  0999 V2000
   -5.0399    0.1850   -0.3788 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8053   -0.5177   -0.4034 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6079    0.1702   -0.2860 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5715    1.5294   -0.1444 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3465    2.1401   -0.0333 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2699    3.5317    0.1152 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1764    1.4196   -0.0636 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0129    2.0872    0.0830 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0962    3.3333    0.2178 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1604    1.3571    0.0818 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3971    1.9472    0.2603 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5750    1.2401    0.2994 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5256   -0.1218    0.1556 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2891   -0.7575   -0.0285 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2770   -2.1395   -0.1591 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1271   -0.0354   -0.0694 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9174   -0.6738   -0.2211 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.9487   -2.0656   -0.5635 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2399    0.0326   -0.2123 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4386   -0.6118   -0.3214 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5762   -1.9845   -0.4558 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7321   -2.7070    0.7633 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0369    1.0528   -1.0647 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8639   -0.4853   -0.6645 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1866    0.5485    0.6740 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4511    2.1237   -0.1176 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1068    4.0764    0.1399 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4230    3.0420    0.3757 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5314    1.7574    0.4427 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3913   -0.7502    0.1749 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0961   -2.7017   -0.1353 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7853   -2.1748   -1.3762 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1151   -2.2420   -1.3196 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0691   -2.7937    0.1961 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1787   -3.6659    0.6234 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8006   -2.9878    0.9160 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3091   -2.1582    1.6192 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
 14 15  1  0
 14 16  2  0
 16 17  1  0
 17 18  1  0
 17 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  1  0
 20  3  1  0
 19  7  1  0
 16 10  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  4 26  1  0
  6 27  1  0
 11 28  1  0
 12 29  1  0
 13 30  1  0
 15 31  1  0
 18 32  1  0
 18 33  1  0
 18 34  1  0
 22 35  1  0
 22 36  1  0
 22 37  1  0
M  END


  Mrv0541 05061305112D          

 22 24  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
    0.0000    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    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
    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
    1.4289    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  4  2  0  0  0  0
  6  4  1  0  0  0  0
  8  5  1  0  0  0  0
  9  6  2  0  0  0  0
 10  7  2  0  0  0  0
 11  7  1  0  0  0  0
 12 10  1  0  0  0  0
 13  8  2  0  0  0  0
 13  9  1  0  0  0  0
 14 12  2  0  0  0  0
 15  8  1  0  0  0  0
 15 12  1  0  0  0  0
 16 11  2  0  0  0  0
 16 14  1  0  0  0  0
 17  1  1  0  0  0  0
 17 13  1  0  0  0  0
 17 14  1  0  0  0  0
 18  9  1  0  0  0  0
 19 10  1  0  0  0  0
 20 15  2  0  0  0  0
 21  2  1  0  0  0  0
 21 11  1  0  0  0  0
 22  3  1  0  0  0  0
 22 16  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0030374

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=C(OC)C2=C(C(O)=C1)C(=O)C1=C(N2C)C(O)=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C16H15NO5/c1-17-13-8(5-4-6-9(13)18)15(20)12-10(19)7-11(21-2)16(22-3)14(12)17/h4-7,18-19H,1-3H3

> <INCHI_KEY>
UTEAJHNFBCLZHN-UHFFFAOYSA-N

> <FORMULA>
C16H15NO5

> <MOLECULAR_WEIGHT>
301.294

> <EXACT_MASS>
301.095022595

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
30.23122656326995

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1,5-dihydroxy-3,4-dimethoxy-10-methyl-9,10-dihydroacridin-9-one

> <ALOGPS_LOGP>
2.49

> <JCHEM_LOGP>
2.8504817036666665

> <ALOGPS_LOGS>
-2.88

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
10.512757700894333

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.126281061705196

> <JCHEM_PKA_STRONGEST_BASIC>
-4.122950473480768

> <JCHEM_POLAR_SURFACE_AREA>
79.23

> <JCHEM_REFRACTIVITY>
80.8466

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.94e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1,5-dihydroxy-3,4-dimethoxy-10-methylacridin-9-one

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0030374
     RDKit          3D
Citrusinine I
 37 39  0  0  0  0  0  0  0  0999 V2000
   -5.0399    0.1850   -0.3788 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8053   -0.5177   -0.4034 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6079    0.1702   -0.2860 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5715    1.5294   -0.1444 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3465    2.1401   -0.0333 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2699    3.5317    0.1152 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1764    1.4196   -0.0636 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0129    2.0872    0.0830 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0962    3.3333    0.2178 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1604    1.3571    0.0818 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3971    1.9472    0.2603 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5750    1.2401    0.2994 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5256   -0.1218    0.1556 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2891   -0.7575   -0.0285 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2770   -2.1395   -0.1591 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1271   -0.0354   -0.0694 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9174   -0.6738   -0.2211 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.9487   -2.0656   -0.5635 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2399    0.0326   -0.2123 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4386   -0.6118   -0.3214 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5762   -1.9845   -0.4558 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7321   -2.7070    0.7633 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0369    1.0528   -1.0647 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8639   -0.4853   -0.6645 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1866    0.5485    0.6740 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4511    2.1237   -0.1176 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1068    4.0764    0.1399 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4230    3.0420    0.3757 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5314    1.7574    0.4427 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3913   -0.7502    0.1749 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0961   -2.7017   -0.1353 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7853   -2.1748   -1.3762 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1151   -2.2420   -1.3196 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0691   -2.7937    0.1961 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1787   -3.6659    0.6234 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8006   -2.9878    0.9160 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3091   -2.1582    1.6192 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
 14 15  1  0
 14 16  2  0
 16 17  1  0
 17 18  1  0
 17 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  1  0
 20  3  1  0
 19  7  1  0
 16 10  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  4 26  1  0
  6 27  1  0
 11 28  1  0
 12 29  1  0
 13 30  1  0
 15 31  1  0
 18 32  1  0
 18 33  1  0
 18 34  1  0
 22 35  1  0
 22 36  1  0
 22 37  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       0.000   6.160   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.001   6.930   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.336   2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.336   3.850   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       6.668   2.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.002   4.620   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.668   3.850   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.001   3.850   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  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM   17  N   UNK     0       5.335   4.620   0.000  0.00  0.00           N+0
HETATM   18  O   UNK     0       8.002   6.160   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       2.667   0.000   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       0.000   4.620   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       2.667   6.160   0.000  0.00  0.00           O+0
CONECT    1   17                                                            
CONECT    2   21                                                            
CONECT    3   22                                                            
CONECT    4    5    6                                                       
CONECT    5    4    8                                                       
CONECT    6    4    9                                                       
CONECT    7   10   11                                                       
CONECT    8    5   13   15                                                  
CONECT    9    6   13   18                                                  
CONECT   10    7   12   19                                                  
CONECT   11    7   16   21                                                  
CONECT   12   10   14   15                                                  
CONECT   13    8    9   17                                                  
CONECT   14   12   16   17                                                  
CONECT   15    8   12   20                                                  
CONECT   16   11   14   22                                                  
CONECT   17    1   13   14                                                  
CONECT   18    9                                                            
CONECT   19   10                                                            
CONECT   20   15                                                            
CONECT   21    2   11                                                       
CONECT   22    3   16                                                       
MASTER        0    0    0    0    0    0    0    0   22    0   48    0
END

COMPND    HMDB0030374
HETATM    1  C1  UNL     1      -5.040   0.185  -0.379  1.00  0.00           C  
HETATM    2  O1  UNL     1      -3.805  -0.518  -0.403  1.00  0.00           O  
HETATM    3  C2  UNL     1      -2.608   0.170  -0.286  1.00  0.00           C  
HETATM    4  C3  UNL     1      -2.572   1.529  -0.144  1.00  0.00           C  
HETATM    5  C4  UNL     1      -1.347   2.140  -0.033  1.00  0.00           C  
HETATM    6  O2  UNL     1      -1.270   3.532   0.115  1.00  0.00           O  
HETATM    7  C5  UNL     1      -0.176   1.420  -0.064  1.00  0.00           C  
HETATM    8  C6  UNL     1       1.013   2.087   0.083  1.00  0.00           C  
HETATM    9  O3  UNL     1       1.096   3.333   0.218  1.00  0.00           O  
HETATM   10  C7  UNL     1       2.160   1.357   0.082  1.00  0.00           C  
HETATM   11  C8  UNL     1       3.397   1.947   0.260  1.00  0.00           C  
HETATM   12  C9  UNL     1       4.575   1.240   0.299  1.00  0.00           C  
HETATM   13  C10 UNL     1       4.526  -0.122   0.156  1.00  0.00           C  
HETATM   14  C11 UNL     1       3.289  -0.757  -0.028  1.00  0.00           C  
HETATM   15  O4  UNL     1       3.277  -2.140  -0.159  1.00  0.00           O  
HETATM   16  C12 UNL     1       2.127  -0.035  -0.069  1.00  0.00           C  
HETATM   17  N1  UNL     1       0.917  -0.674  -0.221  1.00  0.00           N  
HETATM   18  C13 UNL     1       0.949  -2.066  -0.564  1.00  0.00           C  
HETATM   19  C14 UNL     1      -0.240   0.033  -0.212  1.00  0.00           C  
HETATM   20  C15 UNL     1      -1.439  -0.612  -0.321  1.00  0.00           C  
HETATM   21  O5  UNL     1      -1.576  -1.985  -0.456  1.00  0.00           O  
HETATM   22  C16 UNL     1      -1.732  -2.707   0.763  1.00  0.00           C  
HETATM   23  H1  UNL     1      -5.037   1.053  -1.065  1.00  0.00           H  
HETATM   24  H2  UNL     1      -5.864  -0.485  -0.664  1.00  0.00           H  
HETATM   25  H3  UNL     1      -5.187   0.549   0.674  1.00  0.00           H  
HETATM   26  H4  UNL     1      -3.451   2.124  -0.118  1.00  0.00           H  
HETATM   27  H5  UNL     1      -2.107   4.076   0.140  1.00  0.00           H  
HETATM   28  H6  UNL     1       3.423   3.042   0.376  1.00  0.00           H  
HETATM   29  H7  UNL     1       5.531   1.757   0.443  1.00  0.00           H  
HETATM   30  H8  UNL     1       5.391  -0.750   0.175  1.00  0.00           H  
HETATM   31  H9  UNL     1       4.096  -2.702  -0.135  1.00  0.00           H  
HETATM   32  H10 UNL     1       1.785  -2.175  -1.376  1.00  0.00           H  
HETATM   33  H11 UNL     1       0.115  -2.242  -1.320  1.00  0.00           H  
HETATM   34  H12 UNL     1       1.069  -2.794   0.196  1.00  0.00           H  
HETATM   35  H13 UNL     1      -1.179  -3.666   0.623  1.00  0.00           H  
HETATM   36  H14 UNL     1      -2.801  -2.988   0.916  1.00  0.00           H  
HETATM   37  H15 UNL     1      -1.309  -2.158   1.619  1.00  0.00           H  
CONECT    1    2   23   24   25
CONECT    2    3
CONECT    3    4    4   20
CONECT    4    5   26
CONECT    5    6    7    7
CONECT    6   27
CONECT    7    8   19
CONECT    8    9    9   10
CONECT   10   11   11   16
CONECT   11   12   28
CONECT   12   13   13   29
CONECT   13   14   30
CONECT   14   15   16   16
CONECT   15   31
CONECT   16   17
CONECT   17   18   19
CONECT   18   32   33   34
CONECT   19   20   20
CONECT   20   21
CONECT   21   22
CONECT   22   35   36   37
END

HMDB0030374
     RDKit          3D
Citrusinine I
 37 39  0  0  0  0  0  0  0  0999 V2000
   -5.0399    0.1850   -0.3788 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8053   -0.5177   -0.4034 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6079    0.1702   -0.2860 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5715    1.5294   -0.1444 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3465    2.1401   -0.0333 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2699    3.5317    0.1152 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1764    1.4196   -0.0636 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0129    2.0872    0.0830 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0962    3.3333    0.2178 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1604    1.3571    0.0818 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3971    1.9472    0.2603 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5750    1.2401    0.2994 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5256   -0.1218    0.1556 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2891   -0.7575   -0.0285 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2770   -2.1395   -0.1591 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1271   -0.0354   -0.0694 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9174   -0.6738   -0.2211 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.9487   -2.0656   -0.5635 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2399    0.0326   -0.2123 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4386   -0.6118   -0.3214 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5762   -1.9845   -0.4558 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7321   -2.7070    0.7633 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0369    1.0528   -1.0647 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8639   -0.4853   -0.6645 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1866    0.5485    0.6740 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4511    2.1237   -0.1176 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1068    4.0764    0.1399 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4230    3.0420    0.3757 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5314    1.7574    0.4427 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3913   -0.7502    0.1749 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0961   -2.7017   -0.1353 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7853   -2.1748   -1.3762 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1151   -2.2420   -1.3196 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0691   -2.7937    0.1961 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1787   -3.6659    0.6234 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8006   -2.9878    0.9160 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3091   -2.1582    1.6192 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
 14 15  1  0
 14 16  2  0
 16 17  1  0
 17 18  1  0
 17 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  1  0
 20  3  1  0
 19  7  1  0
 16 10  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  4 26  1  0
  6 27  1  0
 11 28  1  0
 12 29  1  0
 13 30  1  0
 15 31  1  0
 18 32  1  0
 18 33  1  0
 18 34  1  0
 22 35  1  0
 22 36  1  0
 22 37  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
1,5-Dihydroxy-3,4-dimethoxy-10-methyl-9(10H)-acridinone	HMDB
1,5-Dihydroxy-3,4-dimethoxy-10-methylacridone	HMDB
Citrusinine-I	HMDB, MeSH
Citrusinine I	MeSH

Chemical Formula

C₁₆H₁₅NO₅

Average Molecular Weight

301.294

Monoisotopic Molecular Weight

301.095022595

IUPAC Name

1,5-dihydroxy-3,4-dimethoxy-10-methyl-9,10-dihydroacridin-9-one

Traditional Name

1,5-dihydroxy-3,4-dimethoxy-10-methylacridin-9-one

CAS Registry Number

86680-32-2

SMILES

COC1=C(OC)C2=C(C(O)=C1)C(=O)C1=C(N2C)C(O)=CC=C1

InChI Identifier

InChI=1S/C16H15NO5/c1-17-13-8(5-4-6-9(13)18)15(20)12-10(19)7-11(21-2)16(22-3)14(12)17/h4-7,18-19H,1-3H3

InChI Key

UTEAJHNFBCLZHN-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
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: HMDB0030374)
Cytoplasm (HMDB: HMDB0030374)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0030374)

Source

Endogenous

Endogenous (HMDB: HMDB0030374)

Plant

Plant (HMDB: HMDB0030374)

Exogenous

Food

Food (HMDB: HMDB0030374)

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	206 - 207 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	66.79 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	0.39 g/L	ALOGPS
logP	2.49	ALOGPS
logP	2.85	ChemAxon
logS	-2.9	ALOGPS
pKa (Strongest Acidic)	9.13	ChemAxon
pKa (Strongest Basic)	-4.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	79.23 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	80.85 m³·mol⁻¹	ChemAxon
Polarizability	30.23 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]+	170.271	31661259
DarkChem	[M-H]-	170.288	31661259
DeepCCS	[M+H]+	173.707	30932474
DeepCCS	[M-H]-	171.349	30932474
DeepCCS	[M-2H]-	205.476	30932474
DeepCCS	[M+Na]+	180.982	30932474
AllCCS	[M+H]+	167.7	32859911
AllCCS	[M+H-H2O]+	164.1	32859911
AllCCS	[M+NH4]+	171.0	32859911
AllCCS	[M+Na]+	171.9	32859911
AllCCS	[M-H]-	172.1	32859911
AllCCS	[M+Na-2H]-	171.5	32859911
AllCCS	[M+HCOO]-	171.0	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Citrusinine I	COC1=C(OC)C2=C(C(O)=C1)C(=O)C1=C(N2C)C(O)=CC=C1	3700.6	Standard polar	33892256
Citrusinine I	COC1=C(OC)C2=C(C(O)=C1)C(=O)C1=C(N2C)C(O)=CC=C1	2510.2	Standard non polar	33892256
Citrusinine I	COC1=C(OC)C2=C(C(O)=C1)C(=O)C1=C(N2C)C(O)=CC=C1	2913.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Citrusinine I,1TMS,isomer #1	COC1=CC(O[Si](C)(C)C)=C2C(=O)C3=CC=CC(O)=C3N(C)C2=C1OC	2909.7	Semi standard non polar	33892256
Citrusinine I,1TMS,isomer #2	COC1=CC(O)=C2C(=O)C3=CC=CC(O[Si](C)(C)C)=C3N(C)C2=C1OC	2907.3	Semi standard non polar	33892256
Citrusinine I,2TMS,isomer #1	COC1=CC(O[Si](C)(C)C)=C2C(=O)C3=CC=CC(O[Si](C)(C)C)=C3N(C)C2=C1OC	2939.8	Semi standard non polar	33892256
Citrusinine I,1TBDMS,isomer #1	COC1=CC(O[Si](C)(C)C(C)(C)C)=C2C(=O)C3=CC=CC(O)=C3N(C)C2=C1OC	3113.1	Semi standard non polar	33892256
Citrusinine I,1TBDMS,isomer #2	COC1=CC(O)=C2C(=O)C3=CC=CC(O[Si](C)(C)C(C)(C)C)=C3N(C)C2=C1OC	3109.1	Semi standard non polar	33892256
Citrusinine I,2TBDMS,isomer #1	COC1=CC(O[Si](C)(C)C(C)(C)C)=C2C(=O)C3=CC=CC(O[Si](C)(C)C(C)(C)C)=C3N(C)C2=C1OC	3335.8	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 I GC-MS (Non-derivatized) - 70eV, Positive	splash10-05fr-0190000000-7ce6d1e07e0a6620d786	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Citrusinine I GC-MS (2 TMS) - 70eV, Positive	splash10-00e9-3026900000-4d76148c6845b2b1566b	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Citrusinine I 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 I 10V, Positive-QTOF	splash10-0udi-0009000000-be3182d1a976ceb1a6df	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Citrusinine I 20V, Positive-QTOF	splash10-0udi-0029000000-779c143ad834b42f2587	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Citrusinine I 40V, Positive-QTOF	splash10-0l0w-0190000000-6740b0cbf8270082bc87	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Citrusinine I 10V, Negative-QTOF	splash10-0udi-0009000000-696e87361a1033f85460	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Citrusinine I 20V, Negative-QTOF	splash10-0udi-0049000000-92f91c6e9558ede613b5	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Citrusinine I 40V, Negative-QTOF	splash10-0ue9-1090000000-b9192551271f60bdf1f5	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Citrusinine I 10V, Negative-QTOF	splash10-0udi-0009000000-8b5d8847eb6f812d58cb	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Citrusinine I 20V, Negative-QTOF	splash10-0udi-0029000000-1627d6cbc4238174f4b2	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Citrusinine I 40V, Negative-QTOF	splash10-00di-2490000000-bc323b892ce44162e502	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Citrusinine I 10V, Positive-QTOF	splash10-0udi-0009000000-0bc18c084a8f1a1da954	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Citrusinine I 20V, Positive-QTOF	splash10-0udi-0009000000-0bc18c084a8f1a1da954	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Citrusinine I 40V, Positive-QTOF	splash10-00di-0980000000-6ddcce8572f6148615bb	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

FDB002223

KNApSAcK ID

C00024249

Chemspider ID

4589521

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5487772

PDB ID

Not Available

ChEBI ID

542878

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1819401

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 I (HMDB0030374)

MOL for HMDB0030374 (Citrusinine I)

3D MOL for HMDB0030374 (Citrusinine I)

3D SDF for HMDB0030374 (Citrusinine I)

3D-SDF for HMDB0030374 (Citrusinine I)

PDB for HMDB0030374 (Citrusinine I)

3D PDB for HMDB0030374 (Citrusinine I)

SMILES for HMDB0030374 (Citrusinine I)

INCHI for HMDB0030374 (Citrusinine I)

Structure for HMDB0030374 (Citrusinine I)

3D Structure for HMDB0030374 (Citrusinine I)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra