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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:35:17 UTC

Update Date

2022-03-07 02:52:27 UTC

HMDB ID

HMDB0030177

Secondary Accession Numbers

HMDB30177

Metabolite Identification

Common Name

Arborinine

Description

Arborinine 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. Based on a literature review a significant number of articles have been published on Arborinine.

Structure

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

HMDB0030177
     RDKit          3D
Arborinine
 36 38  0  0  0  0  0  0  0  0999 V2000
    3.5675   -2.5129    0.0882 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4827   -1.1318    0.2057 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3159   -0.4009    0.2527 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1050   -1.0847    0.1777 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0785   -0.3374    0.2262 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0535    1.0346    0.3441 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1364    1.7311    0.4198 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2600    3.0868    0.5378 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3196    0.9590    0.3695 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5357    1.6062    0.4415 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2076    2.0583   -0.7228 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2477    1.7160    0.3821 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3066    2.9860    0.4900 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4233    0.9924    0.3002 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6294    1.6969    0.3365 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8134    0.9992    0.2532 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8238   -0.3699    0.1356 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6069   -1.0622    0.1006 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4101   -0.3812    0.1831 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2442   -1.0581    0.1456 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1482   -2.5013    0.0386 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9511   -3.0766    0.8229 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2871   -2.8893   -0.9141 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6351   -2.8149    0.2442 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1001   -2.1612    0.0805 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6340    3.8158    0.5921 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0334    2.7334   -0.4603 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6270    1.1670   -1.2300 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5015    2.6325   -1.3545 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6230    2.7799    0.4294 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7658    1.5369    0.2804 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7615   -0.9331    0.0685 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6244   -2.1294    0.0044 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5232   -2.8530    0.9252 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5531   -2.7746   -0.8735 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0628   -3.0594    0.1338 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  7  9  2  0
  9 10  1  0
 10 11  1  0
  6 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  1  0
  9  3  1  0
 19 14  1  0
 20  5  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  4 25  1  0
  8 26  1  0
 11 27  1  0
 11 28  1  0
 11 29  1  0
 15 30  1  0
 16 31  1  0
 17 32  1  0
 18 33  1  0
 21 34  1  0
 21 35  1  0
 21 36  1  0
M  END


  Mrv0541 05061305032D          

 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    2.0625    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
    5.0013    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
    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
    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
    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
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    2.4750    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    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
    0.0000    0.8250    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
  7  5  1  0  0  0  0
  9  6  2  0  0  0  0
 10  7  2  0  0  0  0
 10  9  1  0  0  0  0
 11  8  2  0  0  0  0
 12  8  1  0  0  0  0
 13 11  1  0  0  0  0
 14  9  1  0  0  0  0
 14 13  1  0  0  0  0
 15 13  2  0  0  0  0
 16 12  2  0  0  0  0
 16 15  1  0  0  0  0
 17  1  1  0  0  0  0
 17 10  1  0  0  0  0
 17 11  1  0  0  0  0
 18 14  2  0  0  0  0
 19 15  1  0  0  0  0
 20  2  1  0  0  0  0
 20 12  1  0  0  0  0
 21  3  1  0  0  0  0
 21 16  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0030177

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=C(OC)C(O)=C2C(=O)C3=CC=CC=C3N(C)C2=C1

> <INCHI_IDENTIFIER>
InChI=1S/C16H15NO4/c1-17-10-7-5-4-6-9(10)14(18)13-11(17)8-12(20-2)16(21-3)15(13)19/h4-8,19H,1-3H3

> <INCHI_KEY>
ATBZZQPALSPNMF-UHFFFAOYSA-N

> <FORMULA>
C16H15NO4

> <MOLECULAR_WEIGHT>
285.2946

> <EXACT_MASS>
285.100107973

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
29.758501327149304

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1-hydroxy-2,3-dimethoxy-10-methyl-9,10-dihydroacridin-9-one

> <ALOGPS_LOGP>
2.61

> <JCHEM_LOGP>
3.1540470253333335

> <ALOGPS_LOGS>
-3.06

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.60642147319382

> <JCHEM_PKA_STRONGEST_BASIC>
-1.0530702231113596

> <JCHEM_POLAR_SURFACE_AREA>
59.000000000000014

> <JCHEM_REFRACTIVITY>
78.86569999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.49e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
arborinine

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0030177
     RDKit          3D
Arborinine
 36 38  0  0  0  0  0  0  0  0999 V2000
    3.5675   -2.5129    0.0882 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4827   -1.1318    0.2057 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3159   -0.4009    0.2527 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1050   -1.0847    0.1777 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0785   -0.3374    0.2262 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0535    1.0346    0.3441 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1364    1.7311    0.4198 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2600    3.0868    0.5378 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3196    0.9590    0.3695 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5357    1.6062    0.4415 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2076    2.0583   -0.7228 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2477    1.7160    0.3821 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3066    2.9860    0.4900 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4233    0.9924    0.3002 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6294    1.6969    0.3365 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8134    0.9992    0.2532 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8238   -0.3699    0.1356 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6069   -1.0622    0.1006 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4101   -0.3812    0.1831 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2442   -1.0581    0.1456 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1482   -2.5013    0.0386 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9511   -3.0766    0.8229 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2871   -2.8893   -0.9141 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6351   -2.8149    0.2442 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1001   -2.1612    0.0805 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6340    3.8158    0.5921 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0334    2.7334   -0.4603 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6270    1.1670   -1.2300 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5015    2.6325   -1.3545 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6230    2.7799    0.4294 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7658    1.5369    0.2804 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7615   -0.9331    0.0685 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6244   -2.1294    0.0044 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5232   -2.8530    0.9252 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5531   -2.7746   -0.8735 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0628   -3.0594    0.1338 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  7  9  2  0
  9 10  1  0
 10 11  1  0
  6 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  1  0
  9  3  1  0
 19 14  1  0
 20  5  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  4 25  1  0
  8 26  1  0
 11 27  1  0
 11 28  1  0
 11 29  1  0
 15 30  1  0
 16 31  1  0
 17 32  1  0
 18 33  1  0
 21 34  1  0
 21 35  1  0
 21 36  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       0.000   0.000   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       9.336   3.850   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.002   4.620   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.668   3.850   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.001   2.310   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   1.540   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.334   2.310   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       5.335   0.000   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       0.000   4.620   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       0.000   1.540   0.000  0.00  0.00           O+0
CONECT    1   17                                                            
CONECT    2   20                                                            
CONECT    3   21                                                            
CONECT    4    5    6                                                       
CONECT    5    4    7                                                       
CONECT    6    4    9                                                       
CONECT    7    5   10                                                       
CONECT    8   11   12                                                       
CONECT    9    6   10   14                                                  
CONECT   10    7    9   17                                                  
CONECT   11    8   13   17                                                  
CONECT   12    8   16   20                                                  
CONECT   13   11   14   15                                                  
CONECT   14    9   13   18                                                  
CONECT   15   13   16   19                                                  
CONECT   16   12   15   21                                                  
CONECT   17    1   10   11                                                  
CONECT   18   14                                                            
CONECT   19   15                                                            
CONECT   20    2   12                                                       
CONECT   21    3   16                                                       
MASTER        0    0    0    0    0    0    0    0   21    0   46    0
END

COMPND    HMDB0030177
HETATM    1  C1  UNL     1       3.568  -2.513   0.088  1.00  0.00           C  
HETATM    2  O1  UNL     1       3.483  -1.132   0.206  1.00  0.00           O  
HETATM    3  C2  UNL     1       2.316  -0.401   0.253  1.00  0.00           C  
HETATM    4  C3  UNL     1       1.105  -1.085   0.178  1.00  0.00           C  
HETATM    5  C4  UNL     1      -0.078  -0.337   0.226  1.00  0.00           C  
HETATM    6  C5  UNL     1      -0.053   1.035   0.344  1.00  0.00           C  
HETATM    7  C6  UNL     1       1.136   1.731   0.420  1.00  0.00           C  
HETATM    8  O2  UNL     1       1.260   3.087   0.538  1.00  0.00           O  
HETATM    9  C7  UNL     1       2.320   0.959   0.370  1.00  0.00           C  
HETATM   10  O3  UNL     1       3.536   1.606   0.442  1.00  0.00           O  
HETATM   11  C8  UNL     1       4.208   2.058  -0.723  1.00  0.00           C  
HETATM   12  C9  UNL     1      -1.248   1.716   0.382  1.00  0.00           C  
HETATM   13  O4  UNL     1      -1.307   2.986   0.490  1.00  0.00           O  
HETATM   14  C10 UNL     1      -2.423   0.992   0.300  1.00  0.00           C  
HETATM   15  C11 UNL     1      -3.629   1.697   0.337  1.00  0.00           C  
HETATM   16  C12 UNL     1      -4.813   0.999   0.253  1.00  0.00           C  
HETATM   17  C13 UNL     1      -4.824  -0.370   0.136  1.00  0.00           C  
HETATM   18  C14 UNL     1      -3.607  -1.062   0.101  1.00  0.00           C  
HETATM   19  C15 UNL     1      -2.410  -0.381   0.183  1.00  0.00           C  
HETATM   20  N1  UNL     1      -1.244  -1.058   0.146  1.00  0.00           N  
HETATM   21  C16 UNL     1      -1.148  -2.501   0.039  1.00  0.00           C  
HETATM   22  H1  UNL     1       2.951  -3.077   0.823  1.00  0.00           H  
HETATM   23  H2  UNL     1       3.287  -2.889  -0.914  1.00  0.00           H  
HETATM   24  H3  UNL     1       4.635  -2.815   0.244  1.00  0.00           H  
HETATM   25  H4  UNL     1       1.100  -2.161   0.080  1.00  0.00           H  
HETATM   26  H5  UNL     1       0.634   3.816   0.592  1.00  0.00           H  
HETATM   27  H6  UNL     1       5.033   2.733  -0.460  1.00  0.00           H  
HETATM   28  H7  UNL     1       4.627   1.167  -1.230  1.00  0.00           H  
HETATM   29  H8  UNL     1       3.501   2.633  -1.354  1.00  0.00           H  
HETATM   30  H9  UNL     1      -3.623   2.780   0.429  1.00  0.00           H  
HETATM   31  H10 UNL     1      -5.766   1.537   0.280  1.00  0.00           H  
HETATM   32  H11 UNL     1      -5.762  -0.933   0.068  1.00  0.00           H  
HETATM   33  H12 UNL     1      -3.624  -2.129   0.004  1.00  0.00           H  
HETATM   34  H13 UNL     1      -0.523  -2.853   0.925  1.00  0.00           H  
HETATM   35  H14 UNL     1      -0.553  -2.775  -0.873  1.00  0.00           H  
HETATM   36  H15 UNL     1      -2.063  -3.059   0.134  1.00  0.00           H  
CONECT    1    2   22   23   24
CONECT    2    3
CONECT    3    4    4    9
CONECT    4    5   25
CONECT    5    6    6   20
CONECT    6    7   12
CONECT    7    8    9    9
CONECT    8   26
CONECT    9   10
CONECT   10   11
CONECT   11   27   28   29
CONECT   12   13   13   14
CONECT   14   15   15   19
CONECT   15   16   30
CONECT   16   17   17   31
CONECT   17   18   32
CONECT   18   19   19   33
CONECT   19   20
CONECT   20   21
CONECT   21   34   35   36
END

HMDB0030177
     RDKit          3D
Arborinine
 36 38  0  0  0  0  0  0  0  0999 V2000
    3.5675   -2.5129    0.0882 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4827   -1.1318    0.2057 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3159   -0.4009    0.2527 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1050   -1.0847    0.1777 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0785   -0.3374    0.2262 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0535    1.0346    0.3441 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1364    1.7311    0.4198 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2600    3.0868    0.5378 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3196    0.9590    0.3695 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5357    1.6062    0.4415 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2076    2.0583   -0.7228 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2477    1.7160    0.3821 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3066    2.9860    0.4900 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4233    0.9924    0.3002 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6294    1.6969    0.3365 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8134    0.9992    0.2532 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8238   -0.3699    0.1356 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6069   -1.0622    0.1006 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4101   -0.3812    0.1831 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2442   -1.0581    0.1456 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1482   -2.5013    0.0386 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9511   -3.0766    0.8229 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2871   -2.8893   -0.9141 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6351   -2.8149    0.2442 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1001   -2.1612    0.0805 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6340    3.8158    0.5921 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0334    2.7334   -0.4603 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6270    1.1670   -1.2300 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5015    2.6325   -1.3545 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6230    2.7799    0.4294 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7658    1.5369    0.2804 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7615   -0.9331    0.0685 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6244   -2.1294    0.0044 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5232   -2.8530    0.9252 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5531   -2.7746   -0.8735 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0628   -3.0594    0.1338 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  7  9  2  0
  9 10  1  0
 10 11  1  0
  6 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  1  0
  9  3  1  0
 19 14  1  0
 20  5  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  4 25  1  0
  8 26  1  0
 11 27  1  0
 11 28  1  0
 11 29  1  0
 15 30  1  0
 16 31  1  0
 17 32  1  0
 18 33  1  0
 21 34  1  0
 21 35  1  0
 21 36  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
1-Hydroxy-2,3-dimethoxy-10-methyl-9(10H)-acridinone	HMDB
1-Hydroxy-2,3-dimethoxy-10-methyl-9-acridanone	HMDB
9(10H)-Acridinone, 1-hydroxy-2,3-dimethoxy-10-methyl- (9ci)	HMDB
9-Acridanone, 1-hydroxy-2,3-dimethoxy-10-methyl- (8ci)	HMDB
Arborinin	HMDB
Arbornine	HMDB

Chemical Formula

C₁₆H₁₅NO₄

Average Molecular Weight

285.2946

Monoisotopic Molecular Weight

285.100107973

IUPAC Name

1-hydroxy-2,3-dimethoxy-10-methyl-9,10-dihydroacridin-9-one

Traditional Name

arborinine

CAS Registry Number

5489-57-6

SMILES

COC1=C(OC)C(O)=C2C(=O)C3=CC=CC=C3N(C)C2=C1

InChI Identifier

InChI=1S/C16H15NO4/c1-17-10-7-5-4-6-9(10)14(18)13-11(17)8-12(20-2)16(21-3)15(13)19/h4-8,19H,1-3H3

InChI Key

ATBZZQPALSPNMF-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
Alkyl aryl ether
Pyridine
Benzenoid
Vinylogous amide
Vinylogous acid
Heteroaromatic compound
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

acridines (CHEBI:2804 )
Acridone alkaloids (C10643 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0030177)
Cell membrane (HMDB: HMDB0030177)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0030177)

Source

Endogenous

Endogenous (HMDB: HMDB0030177)

Plant

Plant (HMDB: HMDB0030177)

Exogenous

Food

Food (HMDB: HMDB0030177)

Herb and spice

Herbs and Spices (FooDB: FOOD00866)

Exogenous (HMDB: HMDB0030177)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	175 - 176 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	53.21 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	0.25 g/L	ALOGPS
logP	2.61	ALOGPS
logP	3.15	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Acidic)	10.61	ChemAxon
pKa (Strongest Basic)	-1.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	59 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	78.87 m³·mol⁻¹	ChemAxon
Polarizability	29.76 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]+	165.23	31661259
DarkChem	[M-H]-	166.831	31661259
DeepCCS	[M+H]+	169.255	30932474
DeepCCS	[M-H]-	166.897	30932474
DeepCCS	[M-2H]-	200.04	30932474
DeepCCS	[M+Na]+	175.348	30932474
AllCCS	[M+H]+	164.3	32859911
AllCCS	[M+H-H2O]+	160.6	32859911
AllCCS	[M+NH4]+	167.8	32859911
AllCCS	[M+Na]+	168.8	32859911
AllCCS	[M-H]-	169.8	32859911
AllCCS	[M+Na-2H]-	169.3	32859911
AllCCS	[M+HCOO]-	168.8	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	5.61 minutes	32390414
Predicted by Siyang on May 30, 2022	10.9858 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.36 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	29.2 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2097.2 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	252.0 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	121.9 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	171.4 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	104.7 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	406.3 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	400.9 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	74.1 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	745.3 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	351.0 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1072.6 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	268.8 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	322.1 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	411.0 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	329.8 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	22.2 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Arborinine	COC1=C(OC)C(O)=C2C(=O)C3=CC=CC=C3N(C)C2=C1	3692.5	Standard polar	33892256
Arborinine	COC1=C(OC)C(O)=C2C(=O)C3=CC=CC=C3N(C)C2=C1	2431.5	Standard non polar	33892256
Arborinine	COC1=C(OC)C(O)=C2C(=O)C3=CC=CC=C3N(C)C2=C1	3041.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Arborinine,1TMS,isomer #1	COC1=CC2=C(C(O[Si](C)(C)C)=C1OC)C(=O)C1=CC=CC=C1N2C	2813.4	Semi standard non polar	33892256
Arborinine,1TBDMS,isomer #1	COC1=CC2=C(C(O[Si](C)(C)C(C)(C)C)=C1OC)C(=O)C1=CC=CC=C1N2C	3009.9	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 - Arborinine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0ab9-0390000000-803471e2e8a5988be9f8	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Arborinine GC-MS (1 TMS) - 70eV, Positive	splash10-01vo-2189000000-03dfe780dd3b42767562	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Arborinine 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 - Arborinine 10V, Positive-QTOF	splash10-000i-0090000000-c63c8623e5bb7912d399	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Arborinine 20V, Positive-QTOF	splash10-000i-0090000000-5a0f9f711664318097ff	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Arborinine 40V, Positive-QTOF	splash10-0pbc-1490000000-e491bfb442d306352f77	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Arborinine 10V, Negative-QTOF	splash10-001i-0090000000-de7f067262a9fbcc9551	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Arborinine 20V, Negative-QTOF	splash10-001i-0090000000-b266cbd7783154b1d2bd	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Arborinine 40V, Negative-QTOF	splash10-03ea-1960000000-2f1f389ab18f674bb2d0	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Arborinine 10V, Negative-QTOF	splash10-001i-0090000000-2f3963fff4fc20651d85	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Arborinine 20V, Negative-QTOF	splash10-001i-0090000000-2f3963fff4fc20651d85	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Arborinine 40V, Negative-QTOF	splash10-000t-0980000000-94101d19da05717cfe30	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Arborinine 10V, Positive-QTOF	splash10-000i-0090000000-0bf5e9362c6f6d3b1570	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Arborinine 20V, Positive-QTOF	splash10-000i-0090000000-0bf5e9362c6f6d3b1570	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Arborinine 40V, Positive-QTOF	splash10-0ab9-0970000000-e741569944154b067889	2021-09-22	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane

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

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5281832

PDB ID

Not Available

ChEBI ID

375808

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1817681

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 Arborinine (HMDB0030177)

MOL for HMDB0030177 (Arborinine)

3D MOL for HMDB0030177 (Arborinine)

3D SDF for HMDB0030177 (Arborinine)

3D-SDF for HMDB0030177 (Arborinine)

PDB for HMDB0030177 (Arborinine)

3D PDB for HMDB0030177 (Arborinine)

SMILES for HMDB0030177 (Arborinine)

INCHI for HMDB0030177 (Arborinine)

Structure for HMDB0030177 (Arborinine)

3D Structure for HMDB0030177 (Arborinine)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra