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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:51 UTC

Update Date

2022-03-07 02:51:55 UTC

HMDB ID

HMDB0015257

Secondary Accession Numbers

HMDB15257

Metabolite Identification

Common Name

Anisindione

Description

Anisindione, also known as anisin indandione or miradon, belongs to the class of organic compounds known as indanediones. Indanediones are compounds containing an indane ring bearing two ketone groups. Anisindione is a drug which is used for the prophylaxis and treatment of venous thrombosis and its extension, the treatment of atrial fibrillation with embolization, the prophylaxis and treatment of pulmonary embolism, and as an adjunct in the treatment of coronary occlusion. Anisindione is an extremely weak basic (essentially neutral) compound (based on its pKa). A cyclic beta-diketone consisting of indane-1,3-dione having a 4-methoxyphenyl substituent at the 4-position.

Structure

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

HMDB0015257
     RDKit          3D
Anisindione
 31 33  0  0  0  0  0  0  0  0999 V2000
    5.8038   -0.0031    0.6026 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9170   -0.1862   -0.4722 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5511   -0.1230   -0.2647 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6443   -0.2982   -1.2987 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2735   -0.2336   -1.0844 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7760    0.0063    0.1618 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6401    0.0945    0.4994 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3772    1.1176   -0.2792 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9521    2.1471   -0.8661 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7874    0.6890   -0.2428 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9850    1.3809   -0.3933 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2079    0.7479   -0.3170 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2136   -0.6120   -0.0837 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0187   -1.3107    0.0679 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7893   -0.6712   -0.0093 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4015   -1.1431    0.1083 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9985   -2.2993   -0.0800 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7047    0.1790    1.1848 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0503    0.1159    0.9759 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8479   -0.1993    0.2674 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5452   -0.6568    1.4696 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6736    1.0389    0.9700 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0361   -0.4887   -2.2886 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5801   -0.3743   -1.9117 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8087    0.2928    1.5544 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9661    2.4351   -0.5738 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1528    1.2607   -0.4301 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1512   -1.1739   -0.0120 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0220   -2.3677    0.2491 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3490    0.3722    2.1930 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7195    0.2634    1.8373 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
  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  2  0
  6 18  1  0
 18 19  2  0
 19  3  1  0
 16  7  1  0
 15 10  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  4 23  1  0
  5 24  1  0
  7 25  1  0
 11 26  1  0
 12 27  1  0
 13 28  1  0
 14 29  1  0
 18 30  1  0
 19 31  1  0
M  END

1125
  Mrv0541 02231215162D          

 19 21  0  0  0  0            999 V2000
    4.1159    1.4482    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1159   -1.4482    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6412    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3412    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8597    0.6639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8597   -0.6639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1662    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5787    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5787   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4037    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4037   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8162    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0537   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  5  2  0  0  0  0
  2  6  2  0  0  0  0
  3 18  1  0  0  0  0
  3 19  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  1  0  0  0  0
  4  9  1  0  0  0  0
  5  7  1  0  0  0  0
  6  8  1  0  0  0  0
  7  8  1  0  0  0  0
  7 10  2  0  0  0  0
  8 11  2  0  0  0  0
  9 12  2  0  0  0  0
  9 13  1  0  0  0  0
 10 14  1  0  0  0  0
 11 15  1  0  0  0  0
 12 16  1  0  0  0  0
 13 17  2  0  0  0  0
 14 15  2  0  0  0  0
 16 18  2  0  0  0  0
 17 18  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0015257

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=CC=C(C=C1)C1C(=O)C2=CC=CC=C2C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C16H12O3/c1-19-11-8-6-10(7-9-11)14-15(17)12-4-2-3-5-13(12)16(14)18/h2-9,14H,1H3

> <INCHI_KEY>
XRCFXMGQEVUZFC-UHFFFAOYSA-N

> <FORMULA>
C16H12O3

> <MOLECULAR_WEIGHT>
252.2647

> <EXACT_MASS>
252.07864425

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
26.29842498591167

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-(4-methoxyphenyl)-2,3-dihydro-1H-indene-1,3-dione

> <ALOGPS_LOGP>
2.99

> <JCHEM_LOGP>
2.7232339989999996

> <ALOGPS_LOGS>
-4.30

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.5048360267316205

> <JCHEM_PKA_STRONGEST_BASIC>
-4.823885851129069

> <JCHEM_POLAR_SURFACE_AREA>
43.370000000000005

> <JCHEM_REFRACTIVITY>
71.69670000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.28e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
anisindione

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0015257
     RDKit          3D
Anisindione
 31 33  0  0  0  0  0  0  0  0999 V2000
    5.8038   -0.0031    0.6026 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9170   -0.1862   -0.4722 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5511   -0.1230   -0.2647 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6443   -0.2982   -1.2987 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2735   -0.2336   -1.0844 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7760    0.0063    0.1618 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6401    0.0945    0.4994 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3772    1.1176   -0.2792 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9521    2.1471   -0.8661 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7874    0.6890   -0.2428 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9850    1.3809   -0.3933 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2079    0.7479   -0.3170 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2136   -0.6120   -0.0837 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0187   -1.3107    0.0679 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7893   -0.6712   -0.0093 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4015   -1.1431    0.1083 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9985   -2.2993   -0.0800 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7047    0.1790    1.1848 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0503    0.1159    0.9759 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8479   -0.1993    0.2674 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5452   -0.6568    1.4696 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6736    1.0389    0.9700 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0361   -0.4887   -2.2886 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5801   -0.3743   -1.9117 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8087    0.2928    1.5544 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9661    2.4351   -0.5738 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1528    1.2607   -0.4301 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1512   -1.1739   -0.0120 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0220   -2.3677    0.2491 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3490    0.3722    2.1930 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7195    0.2634    1.8373 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
  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  2  0
  6 18  1  0
 18 19  2  0
 19  3  1  0
 16  7  1  0
 15 10  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  4 23  1  0
  5 24  1  0
  7 25  1  0
 11 26  1  0
 12 27  1  0
 13 28  1  0
 14 29  1  0
 18 30  1  0
 19 31  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 1125                                              
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0       7.683   2.703   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0       7.683  -2.703   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      14.264   0.000   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       8.104   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.205   1.239   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.205  -1.239   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.748   0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.748  -0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.644   0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.414   1.540   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.414  -1.540   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      10.414   1.334   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      10.414  -1.334   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.080   0.770   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.080  -0.770   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      11.954   1.334   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      11.954  -1.334   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      12.724   0.000   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      15.034  -1.334   0.000  0.00  0.00           C+0
CONECT    1    5                                                            
CONECT    2    6                                                            
CONECT    3   18   19                                                       
CONECT    4    5    6    9                                                  
CONECT    5    1    4    7                                                  
CONECT    6    2    4    8                                                  
CONECT    7    5    8   10                                                  
CONECT    8    6    7   11                                                  
CONECT    9    4   12   13                                                  
CONECT   10    7   14                                                       
CONECT   11    8   15                                                       
CONECT   12    9   16                                                       
CONECT   13    9   17                                                       
CONECT   14   10   15                                                       
CONECT   15   11   14                                                       
CONECT   16   12   18                                                       
CONECT   17   13   18                                                       
CONECT   18    3   16   17                                                  
CONECT   19    3                                                            
MASTER        0    0    0    0    0    0    0    0   19    0   42    0
END

COMPND    HMDB0015257
HETATM    1  C1  UNL     1       5.804  -0.003   0.603  1.00  0.00           C  
HETATM    2  O1  UNL     1       4.917  -0.186  -0.472  1.00  0.00           O  
HETATM    3  C2  UNL     1       3.551  -0.123  -0.265  1.00  0.00           C  
HETATM    4  C3  UNL     1       2.644  -0.298  -1.299  1.00  0.00           C  
HETATM    5  C4  UNL     1       1.274  -0.234  -1.084  1.00  0.00           C  
HETATM    6  C5  UNL     1       0.776   0.006   0.162  1.00  0.00           C  
HETATM    7  C6  UNL     1      -0.640   0.094   0.499  1.00  0.00           C  
HETATM    8  C7  UNL     1      -1.377   1.118  -0.279  1.00  0.00           C  
HETATM    9  O2  UNL     1      -0.952   2.147  -0.866  1.00  0.00           O  
HETATM   10  C8  UNL     1      -2.787   0.689  -0.243  1.00  0.00           C  
HETATM   11  C9  UNL     1      -3.985   1.381  -0.393  1.00  0.00           C  
HETATM   12  C10 UNL     1      -5.208   0.748  -0.317  1.00  0.00           C  
HETATM   13  C11 UNL     1      -5.214  -0.612  -0.084  1.00  0.00           C  
HETATM   14  C12 UNL     1      -4.019  -1.311   0.068  1.00  0.00           C  
HETATM   15  C13 UNL     1      -2.789  -0.671  -0.009  1.00  0.00           C  
HETATM   16  C14 UNL     1      -1.401  -1.143   0.108  1.00  0.00           C  
HETATM   17  O3  UNL     1      -0.999  -2.299  -0.080  1.00  0.00           O  
HETATM   18  C15 UNL     1       1.705   0.179   1.185  1.00  0.00           C  
HETATM   19  C16 UNL     1       3.050   0.116   0.976  1.00  0.00           C  
HETATM   20  H1  UNL     1       6.848  -0.199   0.267  1.00  0.00           H  
HETATM   21  H2  UNL     1       5.545  -0.657   1.470  1.00  0.00           H  
HETATM   22  H3  UNL     1       5.674   1.039   0.970  1.00  0.00           H  
HETATM   23  H4  UNL     1       3.036  -0.489  -2.289  1.00  0.00           H  
HETATM   24  H5  UNL     1       0.580  -0.374  -1.912  1.00  0.00           H  
HETATM   25  H6  UNL     1      -0.809   0.293   1.554  1.00  0.00           H  
HETATM   26  H7  UNL     1      -3.966   2.435  -0.574  1.00  0.00           H  
HETATM   27  H8  UNL     1      -6.153   1.261  -0.430  1.00  0.00           H  
HETATM   28  H9  UNL     1      -6.151  -1.174  -0.012  1.00  0.00           H  
HETATM   29  H10 UNL     1      -4.022  -2.368   0.249  1.00  0.00           H  
HETATM   30  H11 UNL     1       1.349   0.372   2.193  1.00  0.00           H  
HETATM   31  H12 UNL     1       3.720   0.263   1.837  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    6   24
CONECT    6    7   18
CONECT    7    8   16   25
CONECT    8    9    9   10
CONECT   10   11   11   15
CONECT   11   12   26
CONECT   12   13   13   27
CONECT   13   14   28
CONECT   14   15   15   29
CONECT   15   16
CONECT   16   17   17
CONECT   18   19   19   30
CONECT   19   31
END

HMDB0015257
     RDKit          3D
Anisindione
 31 33  0  0  0  0  0  0  0  0999 V2000
    5.8038   -0.0031    0.6026 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9170   -0.1862   -0.4722 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5511   -0.1230   -0.2647 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6443   -0.2982   -1.2987 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2735   -0.2336   -1.0844 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7760    0.0063    0.1618 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6401    0.0945    0.4994 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3772    1.1176   -0.2792 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9521    2.1471   -0.8661 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7874    0.6890   -0.2428 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9850    1.3809   -0.3933 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2079    0.7479   -0.3170 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2136   -0.6120   -0.0837 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0187   -1.3107    0.0679 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7893   -0.6712   -0.0093 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4015   -1.1431    0.1083 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9985   -2.2993   -0.0800 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7047    0.1790    1.1848 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0503    0.1159    0.9759 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8479   -0.1993    0.2674 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5452   -0.6568    1.4696 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6736    1.0389    0.9700 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0361   -0.4887   -2.2886 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5801   -0.3743   -1.9117 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8087    0.2928    1.5544 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9661    2.4351   -0.5738 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1528    1.2607   -0.4301 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1512   -1.1739   -0.0120 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0220   -2.3677    0.2491 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3490    0.3722    2.1930 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7195    0.2634    1.8373 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
  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  2  0
  6 18  1  0
 18 19  2  0
 19  3  1  0
 16  7  1  0
 15 10  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  4 23  1  0
  5 24  1  0
  7 25  1  0
 11 26  1  0
 12 27  1  0
 13 28  1  0
 14 29  1  0
 18 30  1  0
 19 31  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
2-(4-Methoxyphenyl)-1H-indene-1,3(2H)-dione	ChEBI
2-(4-Methoxyphenyl)indan-1,3-dione	ChEBI
2-(p-Methoxyphenyl)-1,3-indandione	ChEBI
2-(p-Methoxyphenyl)indane-1,3-dione	ChEBI
2-p-Anisyl-1,3-indandione	ChEBI
2-Para-anisyl-1,3-indandione	ChEBI
Anisin indandione	ChEBI
Anisindiona	ChEBI
Anisindionum	ChEBI
Miradon	Kegg

Chemical Formula

C₁₆H₁₂O₃

Average Molecular Weight

252.2647

Monoisotopic Molecular Weight

252.07864425

IUPAC Name

2-(4-methoxyphenyl)-2,3-dihydro-1H-indene-1,3-dione

Traditional Name

anisindione

CAS Registry Number

117-37-3

SMILES

COC1=CC=C(C=C1)C1C(=O)C2=CC=CC=C2C1=O

InChI Identifier

InChI=1S/C16H12O3/c1-19-11-8-6-10(7-9-11)14-15(17)12-4-2-3-5-13(12)16(14)18/h2-9,14H,1H3

InChI Key

XRCFXMGQEVUZFC-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as indanediones. Indanediones are compounds containing an indane ring bearing two ketone groups.

Kingdom

Super Class

Class

Sub Class

Direct Parent

Alternative Parents

Substituents

Indanedione
Phenoxy compound
Anisole
Methoxybenzene
Aryl alkyl ketone
Aryl ketone
Phenol ether
Alkyl aryl ether
1,3-diketone
Monocyclic benzene moiety
1,3-dicarbonyl compound
Ketone
Ether
Hydrocarbon derivative
Organic oxygen compound
Organooxygen compound
Organic oxide
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic compounds

External Descriptors

aromatic ketone (CHEBI:133809 )
beta-diketone (CHEBI:133809 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Excreta

Biofluid or Excreta

Urine (PMID: 21059682)

Cellular substructure

Membrane (HMDB: HMDB0015257)

Source

Exogenous

Exogenous (HMDB: HMDB0015257)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	156.5 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.013 g/L	Not Available
LogP	2.6	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.013 g/L	ALOGPS
logP	2.99	ALOGPS
logP	2.72	ChemAxon
logS	-4.3	ALOGPS
pKa (Strongest Acidic)	4.5	ChemAxon
pKa (Strongest Basic)	-4.8	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	43.37 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	71.7 m³·mol⁻¹	ChemAxon
Polarizability	26.3 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]+	159.369	31661259
DarkChem	[M-H]-	158.751	31661259
DeepCCS	[M+H]+	158.962	30932474
DeepCCS	[M-H]-	156.604	30932474
DeepCCS	[M-2H]-	189.49	30932474
DeepCCS	[M+Na]+	165.055	30932474
AllCCS	[M+H]+	157.5	32859911
AllCCS	[M+H-H2O]+	153.5	32859911
AllCCS	[M+NH4]+	161.1	32859911
AllCCS	[M+Na]+	162.2	32859911
AllCCS	[M-H]-	161.7	32859911
AllCCS	[M+Na-2H]-	161.0	32859911
AllCCS	[M+HCOO]-	160.4	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Anisindione	COC1=CC=C(C=C1)C1C(=O)C2=CC=CC=C2C1=O	3579.0	Standard polar	33892256
Anisindione	COC1=CC=C(C=C1)C1C(=O)C2=CC=CC=C2C1=O	2305.5	Standard non polar	33892256
Anisindione	COC1=CC=C(C=C1)C1C(=O)C2=CC=CC=C2C1=O	2321.9	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 - Anisindione GC-MS (Non-derivatized) - 70eV, Positive	splash10-0pi0-2970000000-3072f4dff3d83d6798e0	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Anisindione 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 - Anisindione 10V, Positive-QTOF	splash10-0udi-0090000000-9a00a2012741ee8d529d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Anisindione 20V, Positive-QTOF	splash10-0udi-0290000000-ae6d022536ede61e9a68	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Anisindione 40V, Positive-QTOF	splash10-0zfr-5970000000-697cb6e17075d45c94f8	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Anisindione 10V, Negative-QTOF	splash10-0udi-0090000000-1e24bd40cb0266b81059	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Anisindione 20V, Negative-QTOF	splash10-0udi-0090000000-db4a7df8621482e26e27	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Anisindione 40V, Negative-QTOF	splash10-000i-1490000000-17630a8bb2f337db9f2c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Anisindione 10V, Positive-QTOF	splash10-0udi-0090000000-8d91e33e4298322ba53d	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Anisindione 20V, Positive-QTOF	splash10-0udi-0690000000-5f01d86cb0ff3819b608	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Anisindione 40V, Positive-QTOF	splash10-004i-9510000000-c5661b94b65978419e91	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Anisindione 10V, Negative-QTOF	splash10-0udi-0090000000-aedd17caff57899b7eff	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Anisindione 20V, Negative-QTOF	splash10-0udi-0090000000-de3608db6e681e51eb8b	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Anisindione 40V, Negative-QTOF	splash10-0532-0940000000-2d549322c6ad1c2373b4	2021-10-11	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB01125	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB01125	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB01125

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

2112

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Anisindione

METLIN ID

Not Available

PubChem Compound

2197

PDB ID

Not Available

ChEBI ID

133809

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

CONNELL WF, MAYER GA: Evaluation of anticoagulant therapy with anisindione (miradon). Can Med Assoc J. 1959 May 15;80(10):785-90. [PubMed:13652026 ]

Enzymes

Enzyme Details

1. Vitamin K-dependent gamma-carboxylase

General function:: Involved in gamma-glutamyl carboxylase activity
Specific function:: Mediates the vitamin K-dependent carboxylation of glutamate residues to calcium-binding gamma-carboxyglutamate (Gla) residues with the concomitant conversion of the reduced hydroquinone form of vitamin K to vitamin K epoxide.
Gene Name:: GGCX
Uniprot ID:: P38435
Molecular weight:: 87560.065

References

Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]

Showing metabocard for Anisindione (HMDB0015257)

MOL for HMDB0015257 (Anisindione)

3D MOL for HMDB0015257 (Anisindione)

3D SDF for HMDB0015257 (Anisindione)

3D-SDF for HMDB0015257 (Anisindione)

PDB for HMDB0015257 (Anisindione)

3D PDB for HMDB0015257 (Anisindione)

SMILES for HMDB0015257 (Anisindione)

INCHI for HMDB0015257 (Anisindione)

Structure for HMDB0015257 (Anisindione)

3D Structure for HMDB0015257 (Anisindione)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

References