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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:29:40 UTC

Update Date

2022-03-07 02:52:07 UTC

HMDB ID

HMDB0029322

Secondary Accession Numbers

HMDB29322

Metabolite Identification

Common Name

1-Hydroxy-3-methoxy-10-methylacridone

Description

1-Hydroxy-3-methoxy-10-methylacridone, also known as 1-hmma CPD, 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 very few articles have been published on 1-Hydroxy-3-methoxy-10-methylacridone.

Structure

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

HMDB0029322
     RDKit          3D
1-Hydroxy-3-methoxy-10-methylacridone
 32 34  0  0  0  0  0  0  0  0999 V2000
    5.1478    0.2625   -0.2288 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9237   -0.0502   -0.8474 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7072    0.0950   -0.1950 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5976    0.5466    1.0825 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3716    0.7015    1.7639 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4161    1.1669    3.0483 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2365    0.3635    1.0568 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9772    0.4845    1.6553 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1164    0.8919    2.8172 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1110    0.1368    0.9350 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3194    0.2614    1.5549 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4673   -0.0759    0.8791 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3541   -0.5324   -0.4129 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1285   -0.6695   -1.0718 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9916   -0.3280   -0.3835 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7972   -0.4410   -0.9579 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6323   -0.8953   -2.3068 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3190   -0.0978   -0.2430 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5289   -0.2325   -0.8640 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3379    1.3563   -0.2391 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9450   -0.3018   -0.7957 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1232   -0.1580    0.8054 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5180    0.8065    1.6163 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7502    1.3598    3.7205 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3675    0.6193    2.5590 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4358    0.0228    1.3725 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2624   -0.7982   -0.9440 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1006   -1.0366   -2.0820 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0557   -1.7885   -2.3669 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0280   -0.0701   -2.8197 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5026   -0.9973   -2.9288 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6136   -0.6021   -1.8914 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  2  0
 15 16  1  0
 16 17  1  0
 16 18  1  0
 18 19  2  0
 19  3  1  0
 18  7  1  0
 15 10  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  4 23  1  0
  6 24  1  0
 11 25  1  0
 12 26  1  0
 13 27  1  0
 14 28  1  0
 17 29  1  0
 17 30  1  0
 17 31  1  0
 19 32  1  0
M  END


  Mrv0541 02241215582D          

 19 21  0  0  0  0            999 V2000
   -2.8586    0.4135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8586   -0.4127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1438   -0.8260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4303   -0.4127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4303    0.4135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1438    0.8253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7154   -0.8260    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0021   -0.4127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0021    0.4135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7154    0.8253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7126   -0.8260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4262   -0.4127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4262    0.4135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7126    0.8253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7154    1.6517    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7126    1.6517    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1423   -0.8260    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8586   -0.4127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7154   -1.6517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  6  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  4  7  1  0  0  0  0
  5  6  2  0  0  0  0
  5 10  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 11  1  0  0  0  0
  9 10  1  0  0  0  0
  9 14  1  0  0  0  0
 10 15  2  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 12 17  1  0  0  0  0
 13 14  2  0  0  0  0
 14 16  1  0  0  0  0
 17 18  1  0  0  0  0
  7 19  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0029322

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=CC2=C(C(O)=C1)C(=O)C1=CC=CC=C1N2C

> <INCHI_IDENTIFIER>
InChI=1S/C15H13NO3/c1-16-11-6-4-3-5-10(11)15(18)14-12(16)7-9(19-2)8-13(14)17/h3-8,17H,1-2H3

> <INCHI_KEY>
OCUBFJMZYYIVBO-UHFFFAOYSA-N

> <FORMULA>
C15H13NO3

> <MOLECULAR_WEIGHT>
255.2686

> <EXACT_MASS>
255.089543287

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
26.74770717597406

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
2.74

> <JCHEM_LOGP>
3.311718290999999

> <ALOGPS_LOGS>
-2.83

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.041327265250542

> <JCHEM_PKA_STRONGEST_BASIC>
-1.42280750574405

> <JCHEM_POLAR_SURFACE_AREA>
49.77000000000001

> <JCHEM_REFRACTIVITY>
72.4025

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.79e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1-hydroxy-3-methoxy-10-methylacridin-9-one

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0029322
     RDKit          3D
1-Hydroxy-3-methoxy-10-methylacridone
 32 34  0  0  0  0  0  0  0  0999 V2000
    5.1478    0.2625   -0.2288 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9237   -0.0502   -0.8474 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7072    0.0950   -0.1950 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5976    0.5466    1.0825 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3716    0.7015    1.7639 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4161    1.1669    3.0483 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2365    0.3635    1.0568 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9772    0.4845    1.6553 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1164    0.8919    2.8172 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1110    0.1368    0.9350 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3194    0.2614    1.5549 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4673   -0.0759    0.8791 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3541   -0.5324   -0.4129 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1285   -0.6695   -1.0718 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9916   -0.3280   -0.3835 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7972   -0.4410   -0.9579 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6323   -0.8953   -2.3068 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3190   -0.0978   -0.2430 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5289   -0.2325   -0.8640 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3379    1.3563   -0.2391 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9450   -0.3018   -0.7957 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1232   -0.1580    0.8054 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5180    0.8065    1.6163 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7502    1.3598    3.7205 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3675    0.6193    2.5590 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4358    0.0228    1.3725 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2624   -0.7982   -0.9440 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1006   -1.0366   -2.0820 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0557   -1.7885   -2.3669 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0280   -0.0701   -2.8197 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5026   -0.9973   -2.9288 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6136   -0.6021   -1.8914 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  2  0
 15 16  1  0
 16 17  1  0
 16 18  1  0
 18 19  2  0
 19  3  1  0
 18  7  1  0
 15 10  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  4 23  1  0
  6 24  1  0
 11 25  1  0
 12 26  1  0
 13 27  1  0
 14 28  1  0
 17 29  1  0
 17 30  1  0
 17 31  1  0
 19 32  1  0
M  END

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      -5.336   0.772   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -5.336  -0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -4.002  -1.542   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.670  -0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.670   0.772   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -4.002   1.541   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0      -1.335  -1.542   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0      -0.004  -0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.004   0.772   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.335   1.541   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.330  -1.542   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.662  -0.770   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.662   0.772   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.330   1.541   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -1.335   3.083   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       1.330   3.083   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       3.999  -1.542   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       5.336  -0.770   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -1.335  -3.083   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5    7                                                  
CONECT    5    4    6   10                                                  
CONECT    6    1    5                                                       
CONECT    7    4    8   19                                                  
CONECT    8    7    9   11                                                  
CONECT    9    8   10   14                                                  
CONECT   10    5    9   15                                                  
CONECT   11    8   12                                                       
CONECT   12   11   13   17                                                  
CONECT   13   12   14                                                       
CONECT   14    9   13   16                                                  
CONECT   15   10                                                            
CONECT   16   14                                                            
CONECT   17   12   18                                                       
CONECT   18   17                                                            
CONECT   19    7                                                            
MASTER        0    0    0    0    0    0    0    0   19    0   42    0
END

COMPND    HMDB0029322
HETATM    1  C1  UNL     1       5.148   0.262  -0.229  1.00  0.00           C  
HETATM    2  O1  UNL     1       3.924  -0.050  -0.847  1.00  0.00           O  
HETATM    3  C2  UNL     1       2.707   0.095  -0.195  1.00  0.00           C  
HETATM    4  C3  UNL     1       2.598   0.547   1.083  1.00  0.00           C  
HETATM    5  C4  UNL     1       1.372   0.701   1.764  1.00  0.00           C  
HETATM    6  O2  UNL     1       1.416   1.167   3.048  1.00  0.00           O  
HETATM    7  C5  UNL     1       0.236   0.363   1.057  1.00  0.00           C  
HETATM    8  C6  UNL     1      -0.977   0.484   1.655  1.00  0.00           C  
HETATM    9  O3  UNL     1      -1.116   0.892   2.817  1.00  0.00           O  
HETATM   10  C7  UNL     1      -2.111   0.137   0.935  1.00  0.00           C  
HETATM   11  C8  UNL     1      -3.319   0.261   1.555  1.00  0.00           C  
HETATM   12  C9  UNL     1      -4.467  -0.076   0.879  1.00  0.00           C  
HETATM   13  C10 UNL     1      -4.354  -0.532  -0.413  1.00  0.00           C  
HETATM   14  C11 UNL     1      -3.129  -0.670  -1.072  1.00  0.00           C  
HETATM   15  C12 UNL     1      -1.992  -0.328  -0.384  1.00  0.00           C  
HETATM   16  N1  UNL     1      -0.797  -0.441  -0.958  1.00  0.00           N  
HETATM   17  C13 UNL     1      -0.632  -0.895  -2.307  1.00  0.00           C  
HETATM   18  C14 UNL     1       0.319  -0.098  -0.243  1.00  0.00           C  
HETATM   19  C15 UNL     1       1.529  -0.232  -0.864  1.00  0.00           C  
HETATM   20  H1  UNL     1       5.338   1.356  -0.239  1.00  0.00           H  
HETATM   21  H2  UNL     1       5.945  -0.302  -0.796  1.00  0.00           H  
HETATM   22  H3  UNL     1       5.123  -0.158   0.805  1.00  0.00           H  
HETATM   23  H4  UNL     1       3.518   0.806   1.616  1.00  0.00           H  
HETATM   24  H5  UNL     1       0.750   1.360   3.720  1.00  0.00           H  
HETATM   25  H6  UNL     1      -3.368   0.619   2.559  1.00  0.00           H  
HETATM   26  H7  UNL     1      -5.436   0.023   1.372  1.00  0.00           H  
HETATM   27  H8  UNL     1      -5.262  -0.798  -0.944  1.00  0.00           H  
HETATM   28  H9  UNL     1      -3.101  -1.037  -2.082  1.00  0.00           H  
HETATM   29  H10 UNL     1       0.056  -1.788  -2.367  1.00  0.00           H  
HETATM   30  H11 UNL     1      -0.028  -0.070  -2.820  1.00  0.00           H  
HETATM   31  H12 UNL     1      -1.503  -0.997  -2.929  1.00  0.00           H  
HETATM   32  H13 UNL     1       1.614  -0.602  -1.891  1.00  0.00           H  
CONECT    1    2   20   21   22
CONECT    2    3
CONECT    3    4    4   19
CONECT    4    5   23
CONECT    5    6    7    7
CONECT    6   24
CONECT    7    8   18
CONECT    8    9    9   10
CONECT   10   11   11   15
CONECT   11   12   25
CONECT   12   13   13   26
CONECT   13   14   27
CONECT   14   15   15   28
CONECT   15   16
CONECT   16   17   18
CONECT   17   29   30   31
CONECT   18   19   19
CONECT   19   32
END

HMDB0029322
     RDKit          3D
1-Hydroxy-3-methoxy-10-methylacridone
 32 34  0  0  0  0  0  0  0  0999 V2000
    5.1478    0.2625   -0.2288 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9237   -0.0502   -0.8474 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7072    0.0950   -0.1950 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5976    0.5466    1.0825 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3716    0.7015    1.7639 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4161    1.1669    3.0483 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2365    0.3635    1.0568 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9772    0.4845    1.6553 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1164    0.8919    2.8172 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1110    0.1368    0.9350 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3194    0.2614    1.5549 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4673   -0.0759    0.8791 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3541   -0.5324   -0.4129 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1285   -0.6695   -1.0718 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9916   -0.3280   -0.3835 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7972   -0.4410   -0.9579 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6323   -0.8953   -2.3068 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3190   -0.0978   -0.2430 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5289   -0.2325   -0.8640 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3379    1.3563   -0.2391 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9450   -0.3018   -0.7957 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1232   -0.1580    0.8054 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5180    0.8065    1.6163 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7502    1.3598    3.7205 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3675    0.6193    2.5590 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4358    0.0228    1.3725 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2624   -0.7982   -0.9440 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1006   -1.0366   -2.0820 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0557   -1.7885   -2.3669 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0280   -0.0701   -2.8197 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5026   -0.9973   -2.9288 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6136   -0.6021   -1.8914 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  2  0
 15 16  1  0
 16 17  1  0
 16 18  1  0
 18 19  2  0
 19  3  1  0
 18  7  1  0
 15 10  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  4 23  1  0
  6 24  1  0
 11 25  1  0
 12 26  1  0
 13 27  1  0
 14 28  1  0
 17 29  1  0
 17 30  1  0
 17 31  1  0
 19 32  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
1-Hydroxy-3-methoxy-10-methyl-9(10H)-acridinone	HMDB
1-Hydroxy-3-methoxy-10-methyl-9-acridanone	HMDB
1-Hydroxy-3-methoxy-N-methylacridone	HMDB
1-HMMA CPD	HMDB

Chemical Formula

C₁₅H₁₃NO₃

Average Molecular Weight

255.2686

Monoisotopic Molecular Weight

255.089543287

IUPAC Name

1-hydroxy-3-methoxy-10-methyl-9,10-dihydroacridin-9-one

Traditional Name

1-hydroxy-3-methoxy-10-methylacridin-9-one

CAS Registry Number

13161-83-6

SMILES

COC1=CC2=C(C(O)=C1)C(=O)C1=CC=CC=C1N2C

InChI Identifier

InChI=1S/C15H13NO3/c1-16-11-6-4-3-5-10(11)15(18)14-12(16)7-9(19-2)8-13(14)17/h3-8,17H,1-2H3

InChI Key

OCUBFJMZYYIVBO-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as acridones. These are acridines containing a ketone group attached to the C9 carbon atom of the acridine moiety.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Quinolines and derivatives

Sub Class

Benzoquinolines

Direct Parent

Acridones

Alternative Parents

Substituents

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

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0029322)
Cell membrane (HMDB: HMDB0029322)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0029322)

Source

Endogenous

Endogenous (HMDB: HMDB0029322)

Plant

Plant (HMDB: HMDB0029322)

Exogenous

Food

Food (HMDB: HMDB0029322)

Herb and spice

Herbs and Spices (FooDB: FOOD00866)

Exogenous (HMDB: HMDB0029322)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	174 - 176 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.38 g/L	ALOGPS
logP	2.74	ALOGPS
logP	3.31	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Acidic)	10.04	ChemAxon
pKa (Strongest Basic)	-1.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	49.77 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	72.4 m³·mol⁻¹	ChemAxon
Polarizability	26.75 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	159.848	31661259
DarkChem	[M-H]-	161.869	31661259
DeepCCS	[M+H]+	154.352	30932474
DeepCCS	[M-H]-	151.991	30932474
DeepCCS	[M-2H]-	185.462	30932474
DeepCCS	[M+Na]+	160.589	30932474
AllCCS	[M+H]+	156.7	32859911
AllCCS	[M+H-H2O]+	152.7	32859911
AllCCS	[M+NH4]+	160.4	32859911
AllCCS	[M+Na]+	161.5	32859911
AllCCS	[M-H]-	161.6	32859911
AllCCS	[M+Na-2H]-	160.9	32859911
AllCCS	[M+HCOO]-	160.4	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.	6.2 minutes	32390414
Predicted by Siyang on May 30, 2022	10.9393 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.28 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2136.1 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	290.6 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	128.2 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	179.6 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	143.0 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	424.5 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	408.3 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	76.3 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	743.9 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	354.2 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	1102.0 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	293.3 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	306.7 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	479.8 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	345.3 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	21.8 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
1-Hydroxy-3-methoxy-10-methylacridone	COC1=CC2=C(C(O)=C1)C(=O)C1=CC=CC=C1N2C	3425.5	Standard polar	33892256
1-Hydroxy-3-methoxy-10-methylacridone	COC1=CC2=C(C(O)=C1)C(=O)C1=CC=CC=C1N2C	2314.5	Standard non polar	33892256
1-Hydroxy-3-methoxy-10-methylacridone	COC1=CC2=C(C(O)=C1)C(=O)C1=CC=CC=C1N2C	2974.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
1-Hydroxy-3-methoxy-10-methylacridone,1TMS,isomer #1	COC1=CC(O[Si](C)(C)C)=C2C(=O)C3=CC=CC=C3N(C)C2=C1	2709.4	Semi standard non polar	33892256
1-Hydroxy-3-methoxy-10-methylacridone,1TBDMS,isomer #1	COC1=CC(O[Si](C)(C)C(C)(C)C)=C2C(=O)C3=CC=CC=C3N(C)C2=C1	2912.5	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 - 1-Hydroxy-3-methoxy-10-methylacridone GC-MS (Non-derivatized) - 70eV, Positive	splash10-056r-0590000000-4b98531d91b4e6c78394	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 1-Hydroxy-3-methoxy-10-methylacridone GC-MS (1 TMS) - 70eV, Positive	splash10-0229-3395000000-a537b1b3aafa3ea1fed6	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 1-Hydroxy-3-methoxy-10-methylacridone 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 - 1-Hydroxy-3-methoxy-10-methylacridone 10V, Positive-QTOF	splash10-0a4i-0090000000-80ed06fb9dfe19feccbd	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-Hydroxy-3-methoxy-10-methylacridone 20V, Positive-QTOF	splash10-0a4i-0090000000-cc0f8628ad35847c8c8c	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-Hydroxy-3-methoxy-10-methylacridone 40V, Positive-QTOF	splash10-0m2a-1590000000-35e97057748d63b207b8	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-Hydroxy-3-methoxy-10-methylacridone 10V, Negative-QTOF	splash10-0udi-0090000000-c69a58c240611255aabe	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-Hydroxy-3-methoxy-10-methylacridone 20V, Negative-QTOF	splash10-0udi-0090000000-2c9a2560a6ebf050d577	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-Hydroxy-3-methoxy-10-methylacridone 40V, Negative-QTOF	splash10-0bu1-2590000000-4a9a1bfadb34112f08ae	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-Hydroxy-3-methoxy-10-methylacridone 10V, Negative-QTOF	splash10-0udi-0090000000-9ae27670916c21ee015a	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-Hydroxy-3-methoxy-10-methylacridone 20V, Negative-QTOF	splash10-0udi-0090000000-9ae27670916c21ee015a	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-Hydroxy-3-methoxy-10-methylacridone 40V, Negative-QTOF	splash10-00di-0980000000-784fcff440f81d255ae7	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-Hydroxy-3-methoxy-10-methylacridone 10V, Positive-QTOF	splash10-0a4i-0090000000-2b12ce52c95b314953da	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-Hydroxy-3-methoxy-10-methylacridone 20V, Positive-QTOF	splash10-0a4i-0090000000-2b12ce52c95b314953da	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-Hydroxy-3-methoxy-10-methylacridone 40V, Positive-QTOF	splash10-0a4i-0950000000-531062178b9f772f0a66	2021-09-24	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

FDB000383

KNApSAcK ID

C00024230

Chemspider ID

4526466

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5377412

PDB ID

Not Available

ChEBI ID

725388

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 1-Hydroxy-3-methoxy-10-methylacridone (HMDB0029322)

MOL for HMDB0029322 (1-Hydroxy-3-methoxy-10-methylacridone)

3D MOL for HMDB0029322 (1-Hydroxy-3-methoxy-10-methylacridone)

3D SDF for HMDB0029322 (1-Hydroxy-3-methoxy-10-methylacridone)

3D-SDF for HMDB0029322 (1-Hydroxy-3-methoxy-10-methylacridone)

PDB for HMDB0029322 (1-Hydroxy-3-methoxy-10-methylacridone)

3D PDB for HMDB0029322 (1-Hydroxy-3-methoxy-10-methylacridone)

SMILES for HMDB0029322 (1-Hydroxy-3-methoxy-10-methylacridone)

INCHI for HMDB0029322 (1-Hydroxy-3-methoxy-10-methylacridone)

Structure for HMDB0029322 (1-Hydroxy-3-methoxy-10-methylacridone)

3D Structure for HMDB0029322 (1-Hydroxy-3-methoxy-10-methylacridone)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra