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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 15:49:38 UTC

Update Date

2021-09-26 23:11:05 UTC

HMDB ID

HMDB0255882

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Obtusifolin

Description

2,8-dihydroxy-1-methoxy-3-methyl-9,10-dihydroanthracene-9,10-dione belongs to the class of organic compounds known as hydroxyanthraquinones. Hydroxyanthraquinones are compounds containing a hydroxyanthraquinone moiety, which consists of an anthracene bearing a quinone, and hydroxyl group. Based on a literature review very few articles have been published on 2,8-dihydroxy-1-methoxy-3-methyl-9,10-dihydroanthracene-9,10-dione. This compound has been identified in human blood as reported by (PMID: 31557052 ). Obtusifolin is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Obtusifolin is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.

Structure

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

HMDB0255882
     RDKit          3D
Obtusifolin
 33 35  0  0  0  0  0  0  0  0999 V2000
   -1.7820   -3.1215    0.2234 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6464   -1.9743    1.0362 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5872   -0.6908    0.5362 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7321    0.0582    0.3543 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9286   -0.5192    0.6883 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6891    1.3400   -0.1436 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9411    2.1125   -0.3245 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4665    1.8835   -0.4669 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3012    1.1309   -0.2855 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3656   -0.1350    0.2082 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8821   -0.8919    0.3836 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7894   -2.0663    0.8447 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1949   -0.3641    0.0579 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3763   -1.0515    0.2127 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3861   -2.3175    0.6995 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6086   -0.4638   -0.1286 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6314    0.8120   -0.6223 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4626    1.5143   -0.7839 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2480    0.9224   -0.4427 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0059    1.6769   -0.6177 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0780    2.8529   -1.0775 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3845   -2.8740   -0.7682 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2968   -3.9910    0.7048 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8632   -3.4049    0.1117 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7810    0.0079    0.5646 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7593    3.1606   -0.5591 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6363    1.6075   -1.0269 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4631    2.0820    0.6768 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3816    2.8969   -0.8653 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7538   -2.9648    1.0078 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5356   -1.0414    0.0076 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5776    1.2997   -0.8983 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4756    2.5138   -1.1702 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  1  0
  6  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  2  0
 14 15  1  0
 14 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 10  3  1  0
 19 13  1  0
 20  9  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  5 25  1  0
  7 26  1  0
  7 27  1  0
  7 28  1  0
  8 29  1  0
 15 30  1  0
 16 31  1  0
 17 32  1  0
 18 33  1  0
M  END


  Mrv1533004161504072D          

 21 23  0  0  0  0            999 V2000
    1.4289   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    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
    0.7145   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    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
    2.1434   -1.2375    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   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    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
    5.7158   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -3.7125    0.0000 O   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
    3.5724   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  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  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  2  0  0  0  0
 12 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
  3 21  1  0  0  0  0
  9 21  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0255882

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=C(O)C(C)=CC2=C1C(=O)C1=C(O)C=CC=C1C2=O

> <INCHI_IDENTIFIER>
InChI=1S/C16H12O5/c1-7-6-9-12(16(21-2)13(7)18)15(20)11-8(14(9)19)4-3-5-10(11)17/h3-6,17-18H,1-2H3

> <INCHI_KEY>
NYRXUBDGDSRBGB-UHFFFAOYSA-N

> <FORMULA>
C16H12O5

> <MOLECULAR_WEIGHT>
284.267

> <EXACT_MASS>
284.068473486

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
33

> <JCHEM_AVERAGE_POLARIZABILITY>
28.353113106380455

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2,8-dihydroxy-1-methoxy-3-methyl-9,10-dihydroanthracene-9,10-dione

> <ALOGPS_LOGP>
2.96

> <JCHEM_LOGP>
3.317325554999999

> <ALOGPS_LOGS>
-3.47

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.55798511047282

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.936147420002173

> <JCHEM_PKA_STRONGEST_BASIC>
-4.947860498878717

> <JCHEM_POLAR_SURFACE_AREA>
83.83000000000001

> <JCHEM_REFRACTIVITY>
76.6172

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.65e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2,8-dihydroxy-1-methoxy-3-methylanthracene-9,10-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0255882
     RDKit          3D
Obtusifolin
 33 35  0  0  0  0  0  0  0  0999 V2000
   -1.7820   -3.1215    0.2234 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6464   -1.9743    1.0362 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5872   -0.6908    0.5362 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7321    0.0582    0.3543 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9286   -0.5192    0.6883 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6891    1.3400   -0.1436 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9411    2.1125   -0.3245 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4665    1.8835   -0.4669 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3012    1.1309   -0.2855 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3656   -0.1350    0.2082 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8821   -0.8919    0.3836 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7894   -2.0663    0.8447 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1949   -0.3641    0.0579 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3763   -1.0515    0.2127 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3861   -2.3175    0.6995 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6086   -0.4638   -0.1286 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6314    0.8120   -0.6223 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4626    1.5143   -0.7839 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2480    0.9224   -0.4427 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0059    1.6769   -0.6177 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0780    2.8529   -1.0775 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3845   -2.8740   -0.7682 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2968   -3.9910    0.7048 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8632   -3.4049    0.1117 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7810    0.0079    0.5646 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7593    3.1606   -0.5591 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6363    1.6075   -1.0269 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4631    2.0820    0.6768 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3816    2.8969   -0.8653 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7538   -2.9648    1.0078 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5356   -1.0414    0.0076 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5776    1.2997   -0.8983 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4756    2.5138   -1.1702 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  1  0
  6  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  2  0
 14 15  1  0
 14 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 10  3  1  0
 19 13  1  0
 20  9  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  5 25  1  0
  7 26  1  0
  7 27  1  0
  7 28  1  0
  8 29  1  0
 15 30  1  0
 16 31  1  0
 17 32  1  0
 18 33  1  0
M  END

HEADER    PROTEIN                                 16-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   16-APR-15         0                                  
HETATM    1  C   UNK     0       2.667  -7.700   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       4.001  -6.930   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       1.334  -5.390   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       6.668  -0.770   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       8.002  -3.080   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       9.336  -2.310   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      10.669  -3.080   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      10.669  -4.620   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       9.336  -5.390   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       9.336  -6.930   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       8.002  -4.620   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.668  -5.390   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       6.668  -6.930   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   21                                                  
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8   10   21                                                  
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13   18                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   12   19                                                  
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19    3    9                                                  
MASTER        0    0    0    0    0    0    0    0   21    0   46    0
END

COMPND    HMDB0255882
HETATM    1  C1  UNL     1      -1.782  -3.122   0.223  1.00  0.00           C  
HETATM    2  O1  UNL     1      -1.646  -1.974   1.036  1.00  0.00           O  
HETATM    3  C2  UNL     1      -1.587  -0.691   0.536  1.00  0.00           C  
HETATM    4  C3  UNL     1      -2.732   0.058   0.354  1.00  0.00           C  
HETATM    5  O2  UNL     1      -3.929  -0.519   0.688  1.00  0.00           O  
HETATM    6  C4  UNL     1      -2.689   1.340  -0.144  1.00  0.00           C  
HETATM    7  C5  UNL     1      -3.941   2.112  -0.325  1.00  0.00           C  
HETATM    8  C6  UNL     1      -1.466   1.884  -0.467  1.00  0.00           C  
HETATM    9  C7  UNL     1      -0.301   1.131  -0.286  1.00  0.00           C  
HETATM   10  C8  UNL     1      -0.366  -0.135   0.208  1.00  0.00           C  
HETATM   11  C9  UNL     1       0.882  -0.892   0.384  1.00  0.00           C  
HETATM   12  O3  UNL     1       0.789  -2.066   0.845  1.00  0.00           O  
HETATM   13  C10 UNL     1       2.195  -0.364   0.058  1.00  0.00           C  
HETATM   14  C11 UNL     1       3.376  -1.052   0.213  1.00  0.00           C  
HETATM   15  O4  UNL     1       3.386  -2.318   0.700  1.00  0.00           O  
HETATM   16  C12 UNL     1       4.609  -0.464  -0.129  1.00  0.00           C  
HETATM   17  C13 UNL     1       4.631   0.812  -0.622  1.00  0.00           C  
HETATM   18  C14 UNL     1       3.463   1.514  -0.784  1.00  0.00           C  
HETATM   19  C15 UNL     1       2.248   0.922  -0.443  1.00  0.00           C  
HETATM   20  C16 UNL     1       1.006   1.677  -0.618  1.00  0.00           C  
HETATM   21  O5  UNL     1       1.078   2.853  -1.077  1.00  0.00           O  
HETATM   22  H1  UNL     1      -1.384  -2.874  -0.768  1.00  0.00           H  
HETATM   23  H2  UNL     1      -1.297  -3.991   0.705  1.00  0.00           H  
HETATM   24  H3  UNL     1      -2.863  -3.405   0.112  1.00  0.00           H  
HETATM   25  H4  UNL     1      -4.781   0.008   0.565  1.00  0.00           H  
HETATM   26  H5  UNL     1      -3.759   3.161  -0.559  1.00  0.00           H  
HETATM   27  H6  UNL     1      -4.636   1.607  -1.027  1.00  0.00           H  
HETATM   28  H7  UNL     1      -4.463   2.082   0.677  1.00  0.00           H  
HETATM   29  H8  UNL     1      -1.382   2.897  -0.865  1.00  0.00           H  
HETATM   30  H9  UNL     1       2.754  -2.965   1.008  1.00  0.00           H  
HETATM   31  H10 UNL     1       5.536  -1.041   0.008  1.00  0.00           H  
HETATM   32  H11 UNL     1       5.578   1.300  -0.898  1.00  0.00           H  
HETATM   33  H12 UNL     1       3.476   2.514  -1.170  1.00  0.00           H  
CONECT    1    2   22   23   24
CONECT    2    3
CONECT    3    4    4   10
CONECT    4    5    6
CONECT    5   25
CONECT    6    7    8    8
CONECT    7   26   27   28
CONECT    8    9   29
CONECT    9   10   10   20
CONECT   10   11
CONECT   11   12   12   13
CONECT   13   14   14   19
CONECT   14   15   16
CONECT   15   30
CONECT   16   17   17   31
CONECT   17   18   32
CONECT   18   19   19   33
CONECT   19   20
CONECT   20   21   21
END

HMDB0255882
     RDKit          3D
Obtusifolin
 33 35  0  0  0  0  0  0  0  0999 V2000
   -1.7820   -3.1215    0.2234 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6464   -1.9743    1.0362 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5872   -0.6908    0.5362 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7321    0.0582    0.3543 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9286   -0.5192    0.6883 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6891    1.3400   -0.1436 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9411    2.1125   -0.3245 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4665    1.8835   -0.4669 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3012    1.1309   -0.2855 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3656   -0.1350    0.2082 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8821   -0.8919    0.3836 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7894   -2.0663    0.8447 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1949   -0.3641    0.0579 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3763   -1.0515    0.2127 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3861   -2.3175    0.6995 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6086   -0.4638   -0.1286 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6314    0.8120   -0.6223 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4626    1.5143   -0.7839 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2480    0.9224   -0.4427 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0059    1.6769   -0.6177 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0780    2.8529   -1.0775 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3845   -2.8740   -0.7682 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2968   -3.9910    0.7048 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8632   -3.4049    0.1117 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7810    0.0079    0.5646 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7593    3.1606   -0.5591 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6363    1.6075   -1.0269 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4631    2.0820    0.6768 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3816    2.8969   -0.8653 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7538   -2.9648    1.0078 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5356   -1.0414    0.0076 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5776    1.2997   -0.8983 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4756    2.5138   -1.1702 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  1  0
  6  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  2  0
 14 15  1  0
 14 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 10  3  1  0
 19 13  1  0
 20  9  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  5 25  1  0
  7 26  1  0
  7 27  1  0
  7 28  1  0
  8 29  1  0
 15 30  1  0
 16 31  1  0
 17 32  1  0
 18 33  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₁₆H₁₂O₅

Average Molecular Weight

284.267

Monoisotopic Molecular Weight

284.068473486

IUPAC Name

2,8-dihydroxy-1-methoxy-3-methyl-9,10-dihydroanthracene-9,10-dione

Traditional Name

2,8-dihydroxy-1-methoxy-3-methylanthracene-9,10-dione

CAS Registry Number

Not Available

SMILES

COC1=C(O)C(C)=CC2=C1C(=O)C1=C(O)C=CC=C1C2=O

InChI Identifier

InChI=1S/C16H12O5/c1-7-6-9-12(16(21-2)13(7)18)15(20)11-8(14(9)19)4-3-5-10(11)17/h3-6,17-18H,1-2H3

InChI Key

NYRXUBDGDSRBGB-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as hydroxyanthraquinones. Hydroxyanthraquinones are compounds containing a hydroxyanthraquinone moiety, which consists of an anthracene bearing a quinone, and hydroxyl group.

Kingdom

Super Class

Class

Sub Class

Direct Parent

Hydroxyanthraquinones

Alternative Parents

Substituents

Hydroxyanthraquinone
Aryl ketone
Anisole
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Vinylogous acid
Ketone
Ether
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic compounds

External Descriptors

hydroxyanthraquinones (CHEBI:80880 )
Anthraquinone type (C17039 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Process

Not Available

Role

Not Available

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
logP	2.96	ALOGPS
logP	3.32	ChemAxon
logS	-3.5	ALOGPS
pKa (Strongest Acidic)	7.94	ChemAxon
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	83.83 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	76.62 m³·mol⁻¹	ChemAxon
Polarizability	28.35 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]+	166.856	30932474
DeepCCS	[M-H]-	164.498	30932474
DeepCCS	[M-2H]-	197.417	30932474
DeepCCS	[M+Na]+	172.949	30932474
AllCCS	[M+H]+	163.3	32859911
AllCCS	[M+H-H2O]+	159.6	32859911
AllCCS	[M+NH4]+	166.7	32859911
AllCCS	[M+Na]+	167.7	32859911
AllCCS	[M-H]-	166.4	32859911
AllCCS	[M+Na-2H]-	165.7	32859911
AllCCS	[M+HCOO]-	165.1	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Obtusifolin	COC1=C(O)C(C)=CC2=C1C(=O)C1=C(O)C=CC=C1C2=O	3911.9	Standard polar	33892256
Obtusifolin	COC1=C(O)C(C)=CC2=C1C(=O)C1=C(O)C=CC=C1C2=O	2545.3	Standard non polar	33892256
Obtusifolin	COC1=C(O)C(C)=CC2=C1C(=O)C1=C(O)C=CC=C1C2=O	2572.3	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 - Obtusifolin GC-MS (Non-derivatized) - 70eV, Positive	splash10-0bt9-0490000000-9f969849d0d586651286	2021-09-24	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Obtusifolin GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Obtusifolin GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Obtusifolin GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Obtusifolin GC-MS (TMS_2_1) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Obtusifolin GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Obtusifolin GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Obtusifolin GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	31557052	details

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

Not Available

KNApSAcK ID

Not Available

Chemspider ID

2340759

KEGG Compound ID

C17039

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

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

Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]

Showing metabocard for Obtusifolin (HMDB0255882)

MOL for HMDB0255882 (Obtusifolin)

3D MOL for HMDB0255882 (Obtusifolin)

3D SDF for HMDB0255882 (Obtusifolin)

3D-SDF for HMDB0255882 (Obtusifolin)

PDB for HMDB0255882 (Obtusifolin)

3D PDB for HMDB0255882 (Obtusifolin)

SMILES for HMDB0255882 (Obtusifolin)

INCHI for HMDB0255882 (Obtusifolin)

Structure for HMDB0255882 (Obtusifolin)

3D Structure for HMDB0255882 (Obtusifolin)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra