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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-12 02:15:26 UTC

Update Date

2022-03-07 02:56:41 UTC

HMDB ID

HMDB0040683

Secondary Accession Numbers

HMDB40683

Metabolite Identification

Common Name

Grandisine III

Description

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

Structure

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

HMDB0040683
     RDKit          3D
Grandisine III
 34 36  0  0  0  0  0  0  0  0999 V2000
    3.4574   -1.5248    0.6204 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8881   -0.8325   -0.4843 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2129    0.3522   -0.3678 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9335    1.5550   -0.3893 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3165    1.4624   -0.5412 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2868    2.7496   -0.2654 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9284    2.8148   -0.1171 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1958    1.6408   -0.0946 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1694    1.7534    0.0715 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6781    2.9027    0.1805 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9442    0.6203    0.1148 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3137    0.6906    0.3033 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9852    1.8600    0.4339 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0442   -0.5193    0.3619 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4057   -1.7092    0.2356 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1415   -2.8954    0.2969 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0177   -1.7546    0.0447 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2957   -0.6057   -0.0174 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0707   -0.6801   -0.1859 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6709   -1.9742   -0.4615 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8506    0.4006   -0.2240 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5114   -1.2273    0.7928 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8898   -1.3825    1.5522 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4709   -2.6033    0.3592 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8340    2.3243   -0.5567 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8678    3.6637   -0.2855 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3969    3.7552   -0.0159 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7476    2.7712    0.4314 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0972   -0.4501    0.5068 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5180   -3.2831   -0.5488 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5571   -2.7335   -0.0196 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1566   -2.5792   -1.0074 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4249   -1.9705   -1.2710 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8645   -2.5913    0.4126 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
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
 12 14  1  0
 14 15  2  0
 15 16  1  0
 15 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  1  0
 19 21  1  0
 21  3  1  0
 21  8  2  0
 18 11  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  5 25  1  0
  6 26  1  0
  7 27  1  0
 13 28  1  0
 14 29  1  0
 16 30  1  0
 17 31  1  0
 20 32  1  0
 20 33  1  0
 20 34  1  0
M  END


  Mrv0541 05061312022D          

 21 23  0  0  0  0            999 V2000
    1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    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
    0.7145   -0.4125    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
   -0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    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
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    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
  7  5  2  0  0  0  0
  7  6  1  0  0  0  0
  8  3  1  0  0  0  0
  9  5  1  0  0  0  0
 10  4  1  0  0  0  0
 11  6  2  0  0  0  0
 12  9  2  0  0  0  0
 12 11  1  0  0  0  0
 13  8  2  0  0  0  0
 14  8  1  0  0  0  0
 14 12  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  9  1  0  0  0  0
 16 13  1  0  0  0  0
 17  7  1  0  0  0  0
 18 10  1  0  0  0  0
 19 11  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>
HMDB0040683

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=C(O)C=CC2=C1N(C)C1=C(C(O)=CC(O)=C1)C2=O

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

> <INCHI_KEY>
QNXGBYOUHGRJCI-UHFFFAOYSA-N

> <FORMULA>
C15H13NO5

> <MOLECULAR_WEIGHT>
287.2674

> <EXACT_MASS>
287.079372531

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
28.26356634854065

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1,3,6-trihydroxy-5-methoxy-10-methyl-9,10-dihydroacridin-9-one

> <ALOGPS_LOGP>
2.25

> <JCHEM_LOGP>
2.7045876476666666

> <ALOGPS_LOGS>
-2.56

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.628538598966607

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.938710753007417

> <JCHEM_PKA_STRONGEST_BASIC>
-3.5922698892864333

> <JCHEM_POLAR_SURFACE_AREA>
90.23

> <JCHEM_REFRACTIVITY>
76.36430000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.83e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1,3,6-trihydroxy-5-methoxy-10-methylacridin-9-one

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0040683
     RDKit          3D
Grandisine III
 34 36  0  0  0  0  0  0  0  0999 V2000
    3.4574   -1.5248    0.6204 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8881   -0.8325   -0.4843 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2129    0.3522   -0.3678 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9335    1.5550   -0.3893 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3165    1.4624   -0.5412 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2868    2.7496   -0.2654 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9284    2.8148   -0.1171 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1958    1.6408   -0.0946 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1694    1.7534    0.0715 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6781    2.9027    0.1805 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9442    0.6203    0.1148 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3137    0.6906    0.3033 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9852    1.8600    0.4339 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0442   -0.5193    0.3619 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4057   -1.7092    0.2356 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1415   -2.8954    0.2969 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0177   -1.7546    0.0447 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2957   -0.6057   -0.0174 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0707   -0.6801   -0.1859 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6709   -1.9742   -0.4615 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8506    0.4006   -0.2240 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5114   -1.2273    0.7928 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8898   -1.3825    1.5522 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4709   -2.6033    0.3592 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8340    2.3243   -0.5567 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8678    3.6637   -0.2855 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3969    3.7552   -0.0159 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7476    2.7712    0.4314 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0972   -0.4501    0.5068 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5180   -3.2831   -0.5488 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5571   -2.7335   -0.0196 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1566   -2.5792   -1.0074 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4249   -1.9705   -1.2710 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8645   -2.5913    0.4126 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
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
 12 14  1  0
 14 15  2  0
 15 16  1  0
 15 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  1  0
 19 21  1  0
 21  3  1  0
 21  8  2  0
 18 11  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  5 25  1  0
  6 26  1  0
  7 27  1  0
 13 28  1  0
 14 29  1  0
 16 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       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.668  -0.770   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       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM   16  N   UNK     0       2.667  -3.080   0.000  0.00  0.00           N+0
HETATM   17  O   UNK     0       8.002  -3.080   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      -2.667  -3.080   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       5.335   1.540   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       2.667   1.540   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
CONECT    1   16                                                            
CONECT    2   21                                                            
CONECT    3    4    8                                                       
CONECT    4    3   10                                                       
CONECT    5    7    9                                                       
CONECT    6    7   11                                                       
CONECT    7    5    6   17                                                  
CONECT    8    3   13   14                                                  
CONECT    9    5   12   16                                                  
CONECT   10    4   15   18                                                  
CONECT   11    6   12   19                                                  
CONECT   12    9   11   14                                                  
CONECT   13    8   15   16                                                  
CONECT   14    8   12   20                                                  
CONECT   15   10   13   21                                                  
CONECT   16    1    9   13                                                  
CONECT   17    7                                                            
CONECT   18   10                                                            
CONECT   19   11                                                            
CONECT   20   14                                                            
CONECT   21    2   15                                                       
MASTER        0    0    0    0    0    0    0    0   21    0   46    0
END

COMPND    HMDB0040683
HETATM    1  C1  UNL     1       3.457  -1.525   0.620  1.00  0.00           C  
HETATM    2  O1  UNL     1       2.888  -0.833  -0.484  1.00  0.00           O  
HETATM    3  C2  UNL     1       2.213   0.352  -0.368  1.00  0.00           C  
HETATM    4  C3  UNL     1       2.934   1.555  -0.389  1.00  0.00           C  
HETATM    5  O2  UNL     1       4.316   1.462  -0.541  1.00  0.00           O  
HETATM    6  C4  UNL     1       2.287   2.750  -0.265  1.00  0.00           C  
HETATM    7  C5  UNL     1       0.928   2.815  -0.117  1.00  0.00           C  
HETATM    8  C6  UNL     1       0.196   1.641  -0.095  1.00  0.00           C  
HETATM    9  C7  UNL     1      -1.169   1.753   0.071  1.00  0.00           C  
HETATM   10  O3  UNL     1      -1.678   2.903   0.180  1.00  0.00           O  
HETATM   11  C8  UNL     1      -1.944   0.620   0.115  1.00  0.00           C  
HETATM   12  C9  UNL     1      -3.314   0.691   0.303  1.00  0.00           C  
HETATM   13  O4  UNL     1      -3.985   1.860   0.434  1.00  0.00           O  
HETATM   14  C10 UNL     1      -4.044  -0.519   0.362  1.00  0.00           C  
HETATM   15  C11 UNL     1      -3.406  -1.709   0.236  1.00  0.00           C  
HETATM   16  O5  UNL     1      -4.142  -2.895   0.297  1.00  0.00           O  
HETATM   17  C12 UNL     1      -2.018  -1.755   0.045  1.00  0.00           C  
HETATM   18  C13 UNL     1      -1.296  -0.606  -0.017  1.00  0.00           C  
HETATM   19  N1  UNL     1       0.071  -0.680  -0.186  1.00  0.00           N  
HETATM   20  C14 UNL     1       0.671  -1.974  -0.462  1.00  0.00           C  
HETATM   21  C15 UNL     1       0.851   0.401  -0.224  1.00  0.00           C  
HETATM   22  H1  UNL     1       4.511  -1.227   0.793  1.00  0.00           H  
HETATM   23  H2  UNL     1       2.890  -1.383   1.552  1.00  0.00           H  
HETATM   24  H3  UNL     1       3.471  -2.603   0.359  1.00  0.00           H  
HETATM   25  H4  UNL     1       4.834   2.324  -0.557  1.00  0.00           H  
HETATM   26  H5  UNL     1       2.868   3.664  -0.285  1.00  0.00           H  
HETATM   27  H6  UNL     1       0.397   3.755  -0.016  1.00  0.00           H  
HETATM   28  H7  UNL     1      -3.748   2.771   0.431  1.00  0.00           H  
HETATM   29  H8  UNL     1      -5.097  -0.450   0.507  1.00  0.00           H  
HETATM   30  H9  UNL     1      -4.518  -3.283  -0.549  1.00  0.00           H  
HETATM   31  H10 UNL     1      -1.557  -2.733  -0.020  1.00  0.00           H  
HETATM   32  H11 UNL     1      -0.157  -2.579  -1.007  1.00  0.00           H  
HETATM   33  H12 UNL     1       1.425  -1.971  -1.271  1.00  0.00           H  
HETATM   34  H13 UNL     1       0.865  -2.591   0.413  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   27
CONECT    8    9   21   21
CONECT    9   10   10   11
CONECT   11   12   12   18
CONECT   12   13   14
CONECT   13   28
CONECT   14   15   15   29
CONECT   15   16   17
CONECT   16   30
CONECT   17   18   18   31
CONECT   18   19
CONECT   19   20   21
CONECT   20   32   33   34
END

HMDB0040683
     RDKit          3D
Grandisine III
 34 36  0  0  0  0  0  0  0  0999 V2000
    3.4574   -1.5248    0.6204 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8881   -0.8325   -0.4843 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2129    0.3522   -0.3678 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9335    1.5550   -0.3893 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3165    1.4624   -0.5412 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2868    2.7496   -0.2654 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9284    2.8148   -0.1171 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1958    1.6408   -0.0946 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1694    1.7534    0.0715 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6781    2.9027    0.1805 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9442    0.6203    0.1148 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3137    0.6906    0.3033 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9852    1.8600    0.4339 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0442   -0.5193    0.3619 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4057   -1.7092    0.2356 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1415   -2.8954    0.2969 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0177   -1.7546    0.0447 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2957   -0.6057   -0.0174 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0707   -0.6801   -0.1859 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6709   -1.9742   -0.4615 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8506    0.4006   -0.2240 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5114   -1.2273    0.7928 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8898   -1.3825    1.5522 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4709   -2.6033    0.3592 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8340    2.3243   -0.5567 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8678    3.6637   -0.2855 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3969    3.7552   -0.0159 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7476    2.7712    0.4314 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0972   -0.4501    0.5068 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5180   -3.2831   -0.5488 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5571   -2.7335   -0.0196 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1566   -2.5792   -1.0074 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4249   -1.9705   -1.2710 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8645   -2.5913    0.4126 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
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
 12 14  1  0
 14 15  2  0
 15 16  1  0
 15 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  1  0
 19 21  1  0
 21  3  1  0
 21  8  2  0
 18 11  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  5 25  1  0
  6 26  1  0
  7 27  1  0
 13 28  1  0
 14 29  1  0
 16 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
1,3,6-Trihydroxy-5-methoxy-10-methylacridine	HMDB

Chemical Formula

C₁₅H₁₃NO₅

Average Molecular Weight

287.2674

Monoisotopic Molecular Weight

287.079372531

IUPAC Name

1,3,6-trihydroxy-5-methoxy-10-methyl-9,10-dihydroacridin-9-one

Traditional Name

1,3,6-trihydroxy-5-methoxy-10-methylacridin-9-one

CAS Registry Number

Not Available

SMILES

COC1=C(O)C=CC2=C1N(C)C1=C(C(O)=CC(O)=C1)C2=O

InChI Identifier

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

InChI Key

QNXGBYOUHGRJCI-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
Vinylogous amide
Vinylogous acid
Heteroaromatic compound
Polyol
Ether
Azacycle
Organic oxygen compound
Organic nitrogen compound
Organooxygen compound
Organonitrogen compound
Hydrocarbon derivative
Organic oxide
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: HMDB0040683)
Cytoplasm (HMDB: HMDB0040683)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0040683)

Source

Exogenous

Food

Food (HMDB: HMDB0040683)

Fruit

Citrus

Citrus (FooDB: FOOD00859)

Endogenous

Plant

Plant (HMDB: HMDB0040683)

Not Available

Nutrient (HMDB: HMDB0040683)

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.78 g/L	ALOGPS
logP	2.25	ALOGPS
logP	2.7	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Acidic)	7.94	ChemAxon
pKa (Strongest Basic)	-3.6	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	28.26 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
DeepCCS	[M+H]+	165.383	30932474
DeepCCS	[M-H]-	163.026	30932474
DeepCCS	[M-2H]-	196.436	30932474
DeepCCS	[M+Na]+	171.702	30932474
AllCCS	[M+H]+	163.5	32859911
AllCCS	[M+H-H2O]+	159.8	32859911
AllCCS	[M+NH4]+	167.0	32859911
AllCCS	[M+Na]+	168.0	32859911
AllCCS	[M-H]-	166.3	32859911
AllCCS	[M+Na-2H]-	165.6	32859911
AllCCS	[M+HCOO]-	165.0	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Grandisine III	COC1=C(O)C=CC2=C1N(C)C1=C(C(O)=CC(O)=C1)C2=O	3675.7	Standard polar	33892256
Grandisine III	COC1=C(O)C=CC2=C1N(C)C1=C(C(O)=CC(O)=C1)C2=O	2477.0	Standard non polar	33892256
Grandisine III	COC1=C(O)C=CC2=C1N(C)C1=C(C(O)=CC(O)=C1)C2=O	3200.2	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Grandisine III,1TMS,isomer #1	COC1=C(O[Si](C)(C)C)C=CC2=C1N(C)C1=CC(O)=CC(O)=C1C2=O	2971.2	Semi standard non polar	33892256
Grandisine III,1TMS,isomer #2	COC1=C(O)C=CC2=C1N(C)C1=CC(O)=CC(O[Si](C)(C)C)=C1C2=O	2982.0	Semi standard non polar	33892256
Grandisine III,1TMS,isomer #3	COC1=C(O)C=CC2=C1N(C)C1=CC(O[Si](C)(C)C)=CC(O)=C1C2=O	3013.7	Semi standard non polar	33892256
Grandisine III,2TMS,isomer #1	COC1=C(O[Si](C)(C)C)C=CC2=C1N(C)C1=CC(O)=CC(O[Si](C)(C)C)=C1C2=O	2834.3	Semi standard non polar	33892256
Grandisine III,2TMS,isomer #2	COC1=C(O[Si](C)(C)C)C=CC2=C1N(C)C1=CC(O[Si](C)(C)C)=CC(O)=C1C2=O	2887.2	Semi standard non polar	33892256
Grandisine III,2TMS,isomer #3	COC1=C(O)C=CC2=C1N(C)C1=CC(O[Si](C)(C)C)=CC(O[Si](C)(C)C)=C1C2=O	2976.4	Semi standard non polar	33892256
Grandisine III,3TMS,isomer #1	COC1=C(O[Si](C)(C)C)C=CC2=C1N(C)C1=CC(O[Si](C)(C)C)=CC(O[Si](C)(C)C)=C1C2=O	2871.0	Semi standard non polar	33892256
Grandisine III,1TBDMS,isomer #1	COC1=C(O[Si](C)(C)C(C)(C)C)C=CC2=C1N(C)C1=CC(O)=CC(O)=C1C2=O	3233.2	Semi standard non polar	33892256
Grandisine III,1TBDMS,isomer #2	COC1=C(O)C=CC2=C1N(C)C1=CC(O)=CC(O[Si](C)(C)C(C)(C)C)=C1C2=O	3200.3	Semi standard non polar	33892256
Grandisine III,1TBDMS,isomer #3	COC1=C(O)C=CC2=C1N(C)C1=CC(O[Si](C)(C)C(C)(C)C)=CC(O)=C1C2=O	3245.0	Semi standard non polar	33892256
Grandisine III,2TBDMS,isomer #1	COC1=C(O[Si](C)(C)C(C)(C)C)C=CC2=C1N(C)C1=CC(O)=CC(O[Si](C)(C)C(C)(C)C)=C1C2=O	3310.3	Semi standard non polar	33892256
Grandisine III,2TBDMS,isomer #2	COC1=C(O[Si](C)(C)C(C)(C)C)C=CC2=C1N(C)C1=CC(O[Si](C)(C)C(C)(C)C)=CC(O)=C1C2=O	3371.1	Semi standard non polar	33892256
Grandisine III,2TBDMS,isomer #3	COC1=C(O)C=CC2=C1N(C)C1=CC(O[Si](C)(C)C(C)(C)C)=CC(O[Si](C)(C)C(C)(C)C)=C1C2=O	3411.3	Semi standard non polar	33892256
Grandisine III,3TBDMS,isomer #1	COC1=C(O[Si](C)(C)C(C)(C)C)C=CC2=C1N(C)C1=CC(O[Si](C)(C)C(C)(C)C)=CC(O[Si](C)(C)C(C)(C)C)=C1C2=O	3540.6	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 - Grandisine III GC-MS (Non-derivatized) - 70eV, Positive	splash10-0abl-0290000000-267d69d039a49a9a0c66	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Grandisine III GC-MS (3 TMS) - 70eV, Positive	splash10-0080-1012900000-67dc2acd4c46653b8c96	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Grandisine III 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 - Grandisine III 10V, Positive-QTOF	splash10-000i-0090000000-118145fb55879bf4c664	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Grandisine III 20V, Positive-QTOF	splash10-000i-0090000000-474b7160a5a09dd07464	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Grandisine III 40V, Positive-QTOF	splash10-024l-0190000000-4c5ccddf07f1a90e2cdc	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Grandisine III 10V, Negative-QTOF	splash10-000i-0090000000-99e9e57575174ed4c56a	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Grandisine III 20V, Negative-QTOF	splash10-000i-0090000000-745b178d7bb2355c3699	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Grandisine III 40V, Negative-QTOF	splash10-01r6-1290000000-11dbcf82e2cb6d389336	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Grandisine III 10V, Positive-QTOF	splash10-000i-0090000000-653c66c5e9bde424725f	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Grandisine III 20V, Positive-QTOF	splash10-000i-0090000000-653c66c5e9bde424725f	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Grandisine III 40V, Positive-QTOF	splash10-01ox-0390000000-10aa798811d92f00f89c	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Grandisine III 10V, Negative-QTOF	splash10-000i-0090000000-b223092e1b230e39e4b1	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Grandisine III 20V, Negative-QTOF	splash10-000i-0090000000-011c1b9c95f7b92a9e25	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Grandisine III 40V, Negative-QTOF	splash10-03kc-0090000000-c7fb12e1015a5ec2d954	2021-09-25	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

FDB020482

KNApSAcK ID

C00052297

Chemspider ID

4592122

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5494824

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 Grandisine III (HMDB0040683)

MOL for HMDB0040683 (Grandisine III)

3D MOL for HMDB0040683 (Grandisine III)

3D SDF for HMDB0040683 (Grandisine III)

3D-SDF for HMDB0040683 (Grandisine III)

PDB for HMDB0040683 (Grandisine III)

3D PDB for HMDB0040683 (Grandisine III)

SMILES for HMDB0040683 (Grandisine III)

INCHI for HMDB0040683 (Grandisine III)

Structure for HMDB0040683 (Grandisine III)

3D Structure for HMDB0040683 (Grandisine III)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra