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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 18:37:40 UTC

Update Date

2022-03-07 02:53:52 UTC

HMDB ID

HMDB0033853

Secondary Accession Numbers

HMDB33853

Metabolite Identification

Common Name

Rutacridone epoxide

Description

Rutacridone epoxide 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 Rutacridone epoxide.

Structure

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

HMDB0033853
     RDKit          3D
Rutacridone epoxide
 41 45  0  0  0  0  0  0  0  0999 V2000
   -0.5114    1.2598    1.5116 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2986    0.4337    0.6390 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6684    0.4225    0.7199 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3043    1.1022    1.7313 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7038    1.0527    1.7898 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4576    0.3586    0.8871 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7777   -0.3044   -0.1014 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4133   -0.2817   -0.1934 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8196   -0.9856   -1.1971 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4949   -1.6241   -2.0298 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4460   -0.9945   -1.2973 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8664   -1.7268   -2.3076 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4881   -2.4536   -3.2637 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5360   -1.7167   -2.3490 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2834   -1.0289   -1.4480 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6710   -0.2892   -0.4233 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7249   -0.2679   -0.3503 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7247    0.2096    0.3922 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8597    0.4029   -0.6611 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1768    0.3632    0.0356 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5223    1.4330    1.0494 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9488   -0.8539    0.0655 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3355    0.1316   -0.8296 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6860   -0.8807   -1.3108 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1300    0.8332    2.4129 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2504    2.0350    1.9189 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1145    1.9995    0.9440 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7873    1.6514    2.4922 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2150    1.5923    2.5918 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5306    0.3319    0.9462 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3935   -0.8621   -0.8250 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4066   -2.6211   -3.4549 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0267   -2.2811   -3.1315 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1515   -0.7950    0.8601 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7920    0.8334    1.1887 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6603    1.2361   -1.3119 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6117    1.9504    1.3783 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0974    0.9682    1.8675 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2083    2.1939    0.5918 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5759   -1.7899   -0.3893 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7057   -1.0376    0.8616 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  2  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
 12 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 20 22  1  0
 22 23  1  0
 19 24  1  0
 17  2  1  0
 23 20  1  0
  8  3  1  0
 17 11  1  0
 24 15  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  4 28  1  0
  5 29  1  0
  6 30  1  0
  7 31  1  0
 13 32  1  0
 14 33  1  0
 18 34  1  0
 18 35  1  0
 19 36  1  0
 21 37  1  0
 21 38  1  0
 21 39  1  0
 22 40  1  0
 22 41  1  0
M  END


  Mrv0541 05061307242D          

 24 28  0  0  0  0            999 V2000
    2.0255    3.3760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5210    2.7905    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1879    1.4729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9384    2.2593    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6317    0.8636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1326    2.4364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0010    2.2891    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1019    0.1762    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9300    2.1759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8259    1.0407    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4086    1.5719    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5764    1.8271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9077   -0.0008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8524    0.9626    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1929    2.1231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4639    0.6085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2144    1.3948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2697    0.4314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5836    2.6794    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7706    2.0041    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1573   -0.7872    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5193   -0.3549    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8208    2.9937    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1010    1.3033    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  2  0  0  0  0
  5  3  1  0  0  0  0
  6  4  1  0  0  0  0
 10  5  2  0  0  0  0
 11  7  1  0  0  0  0
 12  6  2  0  0  0  0
 12 10  1  0  0  0  0
 13  8  2  0  0  0  0
 14  8  1  0  0  0  0
 14 11  2  0  0  0  0
 15  7  1  0  0  0  0
 16 13  1  0  0  0  0
 17 11  1  0  0  0  0
 17 16  2  0  0  0  0
 18 10  1  0  0  0  0
 18 16  1  0  0  0  0
 19  1  1  0  0  0  0
 19  9  1  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
 20 17  1  0  0  0  0
 21 13  1  0  0  0  0
 22 18  2  0  0  0  0
 23  9  1  0  0  0  0
 23 19  1  0  0  0  0
 24 14  1  0  0  0  0
 24 15  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0033853

> <DATABASE_NAME>
hmdb

> <SMILES>
CN1C2=CC=CC=C2C(=O)C2=C1C1=C(OC(C1)C1(C)CO1)C=C2O

> <INCHI_IDENTIFIER>
InChI=1S/C19H17NO4/c1-19(9-23-19)15-7-11-14(24-15)8-13(21)16-17(11)20(2)12-6-4-3-5-10(12)18(16)22/h3-6,8,15,21H,7,9H2,1-2H3

> <INCHI_KEY>
YXQGLAPCZDYVLL-UHFFFAOYSA-N

> <FORMULA>
C19H17NO4

> <MOLECULAR_WEIGHT>
323.3426

> <EXACT_MASS>
323.115758037

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
33.93682257451212

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5-hydroxy-11-methyl-2-(2-methyloxiran-2-yl)-1H,2H,6H,11H-furo[2,3-c]acridin-6-one

> <ALOGPS_LOGP>
3.10

> <JCHEM_LOGP>
3.533217153999999

> <ALOGPS_LOGS>
-3.06

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.28019271114787

> <JCHEM_PKA_STRONGEST_BASIC>
-4.1376264236035745

> <JCHEM_POLAR_SURFACE_AREA>
62.3

> <JCHEM_REFRACTIVITY>
88.7652

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.79e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
rutacridone epoxide

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0033853
     RDKit          3D
Rutacridone epoxide
 41 45  0  0  0  0  0  0  0  0999 V2000
   -0.5114    1.2598    1.5116 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2986    0.4337    0.6390 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6684    0.4225    0.7199 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3043    1.1022    1.7313 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7038    1.0527    1.7898 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4576    0.3586    0.8871 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7777   -0.3044   -0.1014 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4133   -0.2817   -0.1934 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8196   -0.9856   -1.1971 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4949   -1.6241   -2.0298 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4460   -0.9945   -1.2973 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8664   -1.7268   -2.3076 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4881   -2.4536   -3.2637 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5360   -1.7167   -2.3490 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2834   -1.0289   -1.4480 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6710   -0.2892   -0.4233 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7249   -0.2679   -0.3503 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7247    0.2096    0.3922 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8597    0.4029   -0.6611 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1768    0.3632    0.0356 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5223    1.4330    1.0494 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9488   -0.8539    0.0655 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3355    0.1316   -0.8296 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6860   -0.8807   -1.3108 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1300    0.8332    2.4129 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2504    2.0350    1.9189 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1145    1.9995    0.9440 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7873    1.6514    2.4922 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2150    1.5923    2.5918 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5306    0.3319    0.9462 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3935   -0.8621   -0.8250 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4066   -2.6211   -3.4549 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0267   -2.2811   -3.1315 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1515   -0.7950    0.8601 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7920    0.8334    1.1887 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6603    1.2361   -1.3119 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6117    1.9504    1.3783 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0974    0.9682    1.8675 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2083    2.1939    0.5918 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5759   -1.7899   -0.3893 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7057   -1.0376    0.8616 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  2  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
 12 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 20 22  1  0
 22 23  1  0
 19 24  1  0
 17  2  1  0
 23 20  1  0
  8  3  1  0
 17 11  1  0
 24 15  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  4 28  1  0
  5 29  1  0
  6 30  1  0
  7 31  1  0
 13 32  1  0
 14 33  1  0
 18 34  1  0
 18 35  1  0
 19 36  1  0
 21 37  1  0
 21 38  1  0
 21 39  1  0
 22 40  1  0
 22 41  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       3.781   6.302   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.439   5.209   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      13.417   2.749   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      12.952   4.217   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      12.379   1.612   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      11.448   4.548   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.602   4.273   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.790   0.329   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.736   4.062   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      10.875   1.943   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.363   2.934   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      10.409   3.411   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.294  -0.001   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.324   1.797   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.093   3.963   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.333   1.136   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       7.867   2.604   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       9.837   0.805   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.956   5.002   0.000  0.00  0.00           C+0
HETATM   20  N   UNK     0       8.905   3.741   0.000  0.00  0.00           N+0
HETATM   21  O   UNK     0       7.760  -1.469   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      10.303  -0.662   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       1.532   5.588   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       3.922   2.433   0.000  0.00  0.00           O+0
CONECT    1   19                                                            
CONECT    2   20                                                            
CONECT    3    4    5                                                       
CONECT    4    3    6                                                       
CONECT    5    3   10                                                       
CONECT    6    4   12                                                       
CONECT    7   11   15                                                       
CONECT    8   13   14                                                       
CONECT    9   19   23                                                       
CONECT   10    5   12   18                                                  
CONECT   11    7   14   17                                                  
CONECT   12    6   10   20                                                  
CONECT   13    8   16   21                                                  
CONECT   14    8   11   24                                                  
CONECT   15    7   19   24                                                  
CONECT   16   13   17   18                                                  
CONECT   17   11   16   20                                                  
CONECT   18   10   16   22                                                  
CONECT   19    1    9   15   23                                             
CONECT   20    2   12   17                                                  
CONECT   21   13                                                            
CONECT   22   18                                                            
CONECT   23    9   19                                                       
CONECT   24   14   15                                                       
MASTER        0    0    0    0    0    0    0    0   24    0   56    0
END

COMPND    HMDB0033853
HETATM    1  C1  UNL     1      -0.511   1.260   1.512  1.00  0.00           C  
HETATM    2  N1  UNL     1      -1.299   0.434   0.639  1.00  0.00           N  
HETATM    3  C2  UNL     1      -2.668   0.422   0.720  1.00  0.00           C  
HETATM    4  C3  UNL     1      -3.304   1.102   1.731  1.00  0.00           C  
HETATM    5  C4  UNL     1      -4.704   1.053   1.790  1.00  0.00           C  
HETATM    6  C5  UNL     1      -5.458   0.359   0.887  1.00  0.00           C  
HETATM    7  C6  UNL     1      -4.778  -0.304  -0.101  1.00  0.00           C  
HETATM    8  C7  UNL     1      -3.413  -0.282  -0.193  1.00  0.00           C  
HETATM    9  C8  UNL     1      -2.820  -0.986  -1.197  1.00  0.00           C  
HETATM   10  O1  UNL     1      -3.495  -1.624  -2.030  1.00  0.00           O  
HETATM   11  C9  UNL     1      -1.446  -0.995  -1.297  1.00  0.00           C  
HETATM   12  C10 UNL     1      -0.866  -1.727  -2.308  1.00  0.00           C  
HETATM   13  O2  UNL     1      -1.488  -2.454  -3.264  1.00  0.00           O  
HETATM   14  C11 UNL     1       0.536  -1.717  -2.349  1.00  0.00           C  
HETATM   15  C12 UNL     1       1.283  -1.029  -1.448  1.00  0.00           C  
HETATM   16  C13 UNL     1       0.671  -0.289  -0.423  1.00  0.00           C  
HETATM   17  C14 UNL     1      -0.725  -0.268  -0.350  1.00  0.00           C  
HETATM   18  C15 UNL     1       1.725   0.210   0.392  1.00  0.00           C  
HETATM   19  C16 UNL     1       2.860   0.403  -0.661  1.00  0.00           C  
HETATM   20  C17 UNL     1       4.177   0.363   0.036  1.00  0.00           C  
HETATM   21  C18 UNL     1       4.522   1.433   1.049  1.00  0.00           C  
HETATM   22  C19 UNL     1       4.949  -0.854   0.065  1.00  0.00           C  
HETATM   23  O3  UNL     1       5.335   0.132  -0.830  1.00  0.00           O  
HETATM   24  O4  UNL     1       2.686  -0.881  -1.311  1.00  0.00           O  
HETATM   25  H1  UNL     1      -0.130   0.833   2.413  1.00  0.00           H  
HETATM   26  H2  UNL     1      -1.250   2.035   1.919  1.00  0.00           H  
HETATM   27  H3  UNL     1       0.115   2.000   0.944  1.00  0.00           H  
HETATM   28  H4  UNL     1      -2.787   1.651   2.492  1.00  0.00           H  
HETATM   29  H5  UNL     1      -5.215   1.592   2.592  1.00  0.00           H  
HETATM   30  H6  UNL     1      -6.531   0.332   0.946  1.00  0.00           H  
HETATM   31  H7  UNL     1      -5.393  -0.862  -0.825  1.00  0.00           H  
HETATM   32  H8  UNL     1      -2.407  -2.621  -3.455  1.00  0.00           H  
HETATM   33  H9  UNL     1       1.027  -2.281  -3.131  1.00  0.00           H  
HETATM   34  H10 UNL     1       2.151  -0.795   0.860  1.00  0.00           H  
HETATM   35  H11 UNL     1       1.792   0.833   1.189  1.00  0.00           H  
HETATM   36  H12 UNL     1       2.660   1.236  -1.312  1.00  0.00           H  
HETATM   37  H13 UNL     1       3.612   1.950   1.378  1.00  0.00           H  
HETATM   38  H14 UNL     1       5.097   0.968   1.867  1.00  0.00           H  
HETATM   39  H15 UNL     1       5.208   2.194   0.592  1.00  0.00           H  
HETATM   40  H16 UNL     1       4.576  -1.790  -0.389  1.00  0.00           H  
HETATM   41  H17 UNL     1       5.706  -1.038   0.862  1.00  0.00           H  
CONECT    1    2   25   26   27
CONECT    2    3   17
CONECT    3    4    4    8
CONECT    4    5   28
CONECT    5    6    6   29
CONECT    6    7   30
CONECT    7    8    8   31
CONECT    8    9
CONECT    9   10   10   11
CONECT   11   12   12   17
CONECT   12   13   14
CONECT   13   32
CONECT   14   15   15   33
CONECT   15   16   24
CONECT   16   17   17   18
CONECT   18   19   34   35
CONECT   19   20   24   36
CONECT   20   21   22   23
CONECT   21   37   38   39
CONECT   22   23   40   41
END

HMDB0033853
     RDKit          3D
Rutacridone epoxide
 41 45  0  0  0  0  0  0  0  0999 V2000
   -0.5114    1.2598    1.5116 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2986    0.4337    0.6390 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6684    0.4225    0.7199 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3043    1.1022    1.7313 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7038    1.0527    1.7898 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4576    0.3586    0.8871 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7777   -0.3044   -0.1014 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4133   -0.2817   -0.1934 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8196   -0.9856   -1.1971 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4949   -1.6241   -2.0298 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4460   -0.9945   -1.2973 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8664   -1.7268   -2.3076 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4881   -2.4536   -3.2637 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5360   -1.7167   -2.3490 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2834   -1.0289   -1.4480 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6710   -0.2892   -0.4233 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7249   -0.2679   -0.3503 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7247    0.2096    0.3922 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8597    0.4029   -0.6611 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1768    0.3632    0.0356 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5223    1.4330    1.0494 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9488   -0.8539    0.0655 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3355    0.1316   -0.8296 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6860   -0.8807   -1.3108 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1300    0.8332    2.4129 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2504    2.0350    1.9189 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1145    1.9995    0.9440 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7873    1.6514    2.4922 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2150    1.5923    2.5918 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5306    0.3319    0.9462 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3935   -0.8621   -0.8250 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4066   -2.6211   -3.4549 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0267   -2.2811   -3.1315 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1515   -0.7950    0.8601 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7920    0.8334    1.1887 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6603    1.2361   -1.3119 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6117    1.9504    1.3783 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0974    0.9682    1.8675 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2083    2.1939    0.5918 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5759   -1.7899   -0.3893 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7057   -1.0376    0.8616 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  2  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
 12 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 20 22  1  0
 22 23  1  0
 19 24  1  0
 17  2  1  0
 23 20  1  0
  8  3  1  0
 17 11  1  0
 24 15  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  4 28  1  0
  5 29  1  0
  6 30  1  0
  7 31  1  0
 13 32  1  0
 14 33  1  0
 18 34  1  0
 18 35  1  0
 19 36  1  0
 21 37  1  0
 21 38  1  0
 21 39  1  0
 22 40  1  0
 22 41  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Rutacridon-epoxide	HMDB

Chemical Formula

C₁₉H₁₇NO₄

Average Molecular Weight

323.3426

Monoisotopic Molecular Weight

323.115758037

IUPAC Name

5-hydroxy-11-methyl-2-(2-methyloxiran-2-yl)-1H,2H,6H,11H-furo[2,3-c]acridin-6-one

Traditional Name

rutacridone epoxide

CAS Registry Number

77996-03-3

SMILES

CN1C2=CC=CC=C2C(=O)C2=C1C1=C(OC(C1)C1(C)CO1)C=C2O

InChI Identifier

InChI=1S/C19H17NO4/c1-19(9-23-19)15-7-11-14(24-15)8-13(21)16-17(11)20(2)12-6-4-3-5-10(12)18(16)22/h3-6,8,15,21H,7,9H2,1-2H3

InChI Key

YXQGLAPCZDYVLL-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
Coumaran
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
Pyridine
Benzenoid
Heteroaromatic compound
Vinylogous acid
Vinylogous amide
Dialkyl ether
Oxirane
Ether
Oxacycle
Azacycle
Organic oxygen compound
Organic nitrogen compound
Organonitrogen compound
Organooxygen compound
Hydrocarbon derivative
Organopnictogen compound
Organic oxide
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

acridines (CHEBI:8918 )
alkaloid antibiotic (CHEBI:8918 )
Acridone alkaloids (C10739 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cell membrane (HMDB: HMDB0033853)

Cellular substructure

Membrane (HMDB: HMDB0033853)

Source

Exogenous

Food

Food (HMDB: HMDB0033853)

Not Available

Nutrient (HMDB: HMDB0033853)

Physical Properties

State

Not Available

Experimental Molecular Properties

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

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.28 g/L	ALOGPS
logP	3.1	ALOGPS
logP	3.53	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Acidic)	10.28	ChemAxon
pKa (Strongest Basic)	-4.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	62.3 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	88.77 m³·mol⁻¹	ChemAxon
Polarizability	33.94 Å³	ChemAxon
Number of Rings	5	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]+	172.668	31661259
DarkChem	[M-H]-	170.471	31661259
DeepCCS	[M+H]+	168.33	30932474
DeepCCS	[M-H]-	165.972	30932474
DeepCCS	[M-2H]-	199.34	30932474
DeepCCS	[M+Na]+	174.567	30932474
AllCCS	[M+H]+	176.4	32859911
AllCCS	[M+H-H2O]+	172.9	32859911
AllCCS	[M+NH4]+	179.6	32859911
AllCCS	[M+Na]+	180.5	32859911
AllCCS	[M-H]-	184.0	32859911
AllCCS	[M+Na-2H]-	183.4	32859911
AllCCS	[M+HCOO]-	182.8	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Rutacridone epoxide	CN1C2=CC=CC=C2C(=O)C2=C1C1=C(OC(C1)C1(C)CO1)C=C2O	3882.9	Standard polar	33892256
Rutacridone epoxide	CN1C2=CC=CC=C2C(=O)C2=C1C1=C(OC(C1)C1(C)CO1)C=C2O	2653.9	Standard non polar	33892256
Rutacridone epoxide	CN1C2=CC=CC=C2C(=O)C2=C1C1=C(OC(C1)C1(C)CO1)C=C2O	3338.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Rutacridone epoxide,1TMS,isomer #1	CN1C2=CC=CC=C2C(=O)C2=C(O[Si](C)(C)C)C=C3OC(C4(C)CO4)CC3=C21	3121.0	Semi standard non polar	33892256
Rutacridone epoxide,1TBDMS,isomer #1	CN1C2=CC=CC=C2C(=O)C2=C(O[Si](C)(C)C(C)(C)C)C=C3OC(C4(C)CO4)CC3=C21	3313.2	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 - Rutacridone epoxide GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4i-9476000000-d04ba9b538989afef983	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Rutacridone epoxide GC-MS (1 TMS) - 70eV, Positive	splash10-0a4i-7309000000-7118cb758c950d801f70	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Rutacridone epoxide 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 - Rutacridone epoxide 10V, Positive-QTOF	splash10-00di-1009000000-710385ccd4c56e59a29f	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Rutacridone epoxide 20V, Positive-QTOF	splash10-00di-1039000000-413126f890f9ec962354	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Rutacridone epoxide 40V, Positive-QTOF	splash10-0a4i-9030000000-8d63a8c49978cde98ddb	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Rutacridone epoxide 10V, Negative-QTOF	splash10-00di-0019000000-6e5dff6fd4ceff255aec	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Rutacridone epoxide 20V, Negative-QTOF	splash10-00di-1029000000-9d1ff5df483311e4aa61	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Rutacridone epoxide 40V, Negative-QTOF	splash10-0a4i-9040000000-f1ef1e8588584eb77e99	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Rutacridone epoxide 10V, Negative-QTOF	splash10-00di-0009000000-991a74014b2b59c6013a	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Rutacridone epoxide 20V, Negative-QTOF	splash10-0006-0093000000-ecbd926c2895a4ed5320	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Rutacridone epoxide 40V, Negative-QTOF	splash10-01pc-0291000000-5d574c6e4c23e5778b28	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Rutacridone epoxide 10V, Positive-QTOF	splash10-00di-0009000000-c709cf6936a267877edb	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Rutacridone epoxide 20V, Positive-QTOF	splash10-00di-0009000000-e506f411a9ad652f3d0b	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Rutacridone epoxide 40V, Positive-QTOF	splash10-0a4l-1494000000-e6c25c1860b82ae5a2a2	2021-09-25	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

5281850

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for Rutacridone epoxide (HMDB0033853)

MOL for HMDB0033853 (Rutacridone epoxide)

3D MOL for HMDB0033853 (Rutacridone epoxide)

3D SDF for HMDB0033853 (Rutacridone epoxide)

3D-SDF for HMDB0033853 (Rutacridone epoxide)

PDB for HMDB0033853 (Rutacridone epoxide)

3D PDB for HMDB0033853 (Rutacridone epoxide)

SMILES for HMDB0033853 (Rutacridone epoxide)

INCHI for HMDB0033853 (Rutacridone epoxide)

Structure for HMDB0033853 (Rutacridone epoxide)

3D Structure for HMDB0033853 (Rutacridone epoxide)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra