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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-12 02:21:06 UTC

Update Date

2022-03-07 02:56:43 UTC

HMDB ID

HMDB0040769

Secondary Accession Numbers

HMDB40769

Metabolite Identification

Common Name

Dioxinoacrimarine A

Description

Dioxinoacrimarine A 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. Dioxinoacrimarine A has been detected, but not quantified in, citrus. This could make dioxinoacrimarine a a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Dioxinoacrimarine A.

Structure

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


  Mrv0541 05061312072D          

 38 43  0  0  0  0            999 V2000
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    2.6048   -3.1539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3854   -3.1539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6869   -1.0368    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.0647   -0.3475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9789   -0.6132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2546   -0.5034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

HMDB0040769
     RDKit          3D
Dioxinoacrimarine A
 61 66  0  0  0  0  0  0  0  0999 V2000
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M  END


  Mrv0541 05061312072D          

 38 43  0  0  0  0            999 V2000
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M  END
> <DATABASE_ID>
HMDB0040769

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=CC2=C(C(O)=C1)C(=O)C1=C(N2C)C2=C(OC(C)(CO2)\C=C\C2=C(O)C=CC3=C2OC(=O)C=C3)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C29H23NO8/c1-29(11-10-17-20(31)7-4-15-5-9-23(33)37-27(15)17)14-36-28-22(38-29)8-6-18-25(28)30(2)19-12-16(35-3)13-21(32)24(19)26(18)34/h4-13,31-32H,14H2,1-3H3/b11-10+

> <INCHI_KEY>
AEXHLHGCDOTWGS-ZHACJKMWSA-N

> <FORMULA>
C29H23NO8

> <MOLECULAR_WEIGHT>
513.4948

> <EXACT_MASS>
513.142366717

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_AVERAGE_POLARIZABILITY>
53.6731247312989

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
9-hydroxy-2-[(E)-2-(7-hydroxy-2-oxo-2H-chromen-8-yl)ethenyl]-7-methoxy-2,5-dimethyl-2,3,5,10-tetrahydro-1,4-dioxa-5-azatetraphen-10-one

> <ALOGPS_LOGP>
4.46

> <JCHEM_LOGP>
5.0061318230000005

> <ALOGPS_LOGS>
-4.81

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
10.036452838117203

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.798567332022252

> <JCHEM_PKA_STRONGEST_BASIC>
-4.194576691998951

> <JCHEM_POLAR_SURFACE_AREA>
114.76000000000002

> <JCHEM_REFRACTIVITY>
140.07099999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
7.95e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
9-hydroxy-2-[(E)-2-(7-hydroxy-2-oxochromen-8-yl)ethenyl]-7-methoxy-2,5-dimethyl-3H-1,4-dioxa-5-azatetraphen-10-one

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0040769
     RDKit          3D
Dioxinoacrimarine A
 61 66  0  0  0  0  0  0  0  0999 V2000
    7.9258    2.5564   -0.2478 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2993    1.2054   -0.3430 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2784    0.2416   -0.2862 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6001   -1.0823   -0.3751 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5635   -2.0401   -0.3165 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9338   -3.3443   -0.4092 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2481   -1.6591   -0.1724 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2142   -2.5681   -0.1097 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4359   -3.7931   -0.1845 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8964   -2.1873    0.0367 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8762   -3.1397    0.0985 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5588   -2.7726    0.2468 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2630   -1.4328    0.3341 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2911   -0.4812    0.2713 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6112   -0.8455    0.1227 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6193    0.0825    0.0630 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2554    1.4601    0.1522 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9111   -0.3029   -0.0807 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9450    0.6026   -0.1413 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9079    0.8205    0.3661 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3596    1.3260    0.0714 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4195    0.2852   -0.0785 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6756    0.0501   -1.5467 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6817    0.6672    0.6395 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8569    0.3885    0.1296 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1591    0.6820    0.6835 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4167    1.3156    1.8628 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3554    1.7425    2.6477 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7265    1.5386    2.2873 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8169    1.1385    1.5520 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5564    0.5003    0.3641 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6047    0.0744   -0.4194 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3190   -0.5606   -1.6018 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0182   -0.7576   -1.9779 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7405   -1.3522   -3.0852 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0533   -0.3443   -1.2172 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2697    0.2665   -0.0803 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0199   -0.9496    0.4842 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.8268    3.2043   -0.1370 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3896    2.9254   -1.1511 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3243    2.7426    0.6798 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.6296   -1.3847   -0.4880 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5195   -4.2144   -0.4070 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1840   -4.1838    0.0228 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2102   -3.5089    0.2924 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1094    2.1386    0.0520 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8110    1.7377    1.1347 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6021    1.7821   -0.7221 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7715    1.6590   -0.0764 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3492    1.9552   -0.8621 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6879    2.0075    0.9050 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3248    0.8333   -1.9915 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1295   -0.9701   -1.6256 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6994    0.0196   -2.0618 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6285    1.1739    1.5802 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8108   -0.1268   -0.8279 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4767    2.2148    3.5295 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8690    2.0482    3.2355 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8258    1.3193    1.8958 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.6464    0.2266   -0.1286 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0945   -0.9304   -2.2831 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
 14 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 22 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 27 29  1  0
 29 30  2  0
 30 31  1  0
 31 32  1  0
 32 33  2  0
 33 34  1  0
 34 35  2  0
 34 36  1  0
 36 37  1  0
 22 38  1  0
 19  3  1  0
 37 26  1  0
 18  7  1  0
 37 31  2  0
 15 10  1  0
 38 13  1  0
  1 39  1  0
  1 40  1  0
  1 41  1  0
  4 42  1  0
  6 43  1  0
 11 44  1  0
 12 45  1  0
 17 46  1  0
 17 47  1  0
 17 48  1  0
 19 49  1  0
 21 50  1  0
 21 51  1  0
 23 52  1  0
 23 53  1  0
 23 54  1  0
 24 55  1  0
 25 56  1  0
 28 57  1  0
 29 58  1  0
 30 59  1  0
 32 60  1  0
 33 61  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      -1.150  -5.336   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.862  -5.887   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      11.919  -5.887   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -6.882  -1.935   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -8.180  -4.266   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.854  -0.649   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -5.561  -1.145   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.342  -0.940   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -8.156  -5.806   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -2.846  -4.183   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.524  -3.392   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.887  -5.305   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       9.903  -3.559   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.830  -5.305   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -6.858  -3.475   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       9.399  -5.014   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -4.191  -3.434   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.862  -1.813   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.879  -4.141   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -4.215  -1.894   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       8.895  -2.395   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       1.838  -2.395   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -6.810  -6.555   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       7.383  -2.686   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       4.358  -3.268   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       6.374  -1.522   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -5.513  -4.224   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       2.846  -3.559   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -0.179  -4.141   0.000  0.00  0.00           C+0
HETATM   30  N   UNK     0       5.366  -4.432   0.000  0.00  0.00           N+0
HETATM   31  O   UNK     0      -2.894  -1.103   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0       9.399  -0.940   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0      -6.786  -8.095   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0       6.879  -0.067   0.000  0.00  0.00           O+0
HETATM   35  O   UNK     0      10.407  -6.178   0.000  0.00  0.00           O+0
HETATM   36  O   UNK     0       2.342  -5.014   0.000  0.00  0.00           O+0
HETATM   37  O   UNK     0      -5.489  -5.764   0.000  0.00  0.00           O+0
HETATM   38  O   UNK     0       0.326  -2.686   0.000  0.00  0.00           O+0
CONECT    1   29                                                            
CONECT    2   30                                                            
CONECT    3   35                                                            
CONECT    4    7   15                                                       
CONECT    5    9   15                                                       
CONECT    6    8   18                                                       
CONECT    7    4   20                                                       
CONECT    8    6   22                                                       
CONECT    9    5   23                                                       
CONECT   10   11   17                                                       
CONECT   11   10   29                                                       
CONECT   12   16   19                                                       
CONECT   13   16   21                                                       
CONECT   14   29   36                                                       
CONECT   15    4    5   27                                                  
CONECT   16   12   13   35                                                  
CONECT   17   10   20   27                                                  
CONECT   18    6   25   26                                                  
CONECT   19   12   24   30                                                  
CONECT   20    7   17   31                                                  
CONECT   21   13   24   32                                                  
CONECT   22    8   28   38                                                  
CONECT   23    9   33   37                                                  
CONECT   24   19   21   26                                                  
CONECT   25   18   28   30                                                  
CONECT   26   18   24   34                                                  
CONECT   27   15   17   37                                                  
CONECT   28   22   25   36                                                  
CONECT   29    1   11   14   38                                             
CONECT   30    2   19   25                                                  
CONECT   31   20                                                            
CONECT   32   21                                                            
CONECT   33   23                                                            
CONECT   34   26                                                            
CONECT   35    3   16                                                       
CONECT   36   14   28                                                       
CONECT   37   23   27                                                       
CONECT   38   22   29                                                       
MASTER        0    0    0    0    0    0    0    0   38    0   86    0
END

COMPND    HMDB0040769
HETATM    1  C1  UNL     1       7.926   2.556  -0.248  1.00  0.00           C  
HETATM    2  O1  UNL     1       8.299   1.205  -0.343  1.00  0.00           O  
HETATM    3  C2  UNL     1       7.278   0.242  -0.286  1.00  0.00           C  
HETATM    4  C3  UNL     1       7.600  -1.082  -0.375  1.00  0.00           C  
HETATM    5  C4  UNL     1       6.564  -2.040  -0.316  1.00  0.00           C  
HETATM    6  O2  UNL     1       6.934  -3.344  -0.409  1.00  0.00           O  
HETATM    7  C5  UNL     1       5.248  -1.659  -0.172  1.00  0.00           C  
HETATM    8  C6  UNL     1       4.214  -2.568  -0.110  1.00  0.00           C  
HETATM    9  O3  UNL     1       4.436  -3.793  -0.185  1.00  0.00           O  
HETATM   10  C7  UNL     1       2.896  -2.187   0.037  1.00  0.00           C  
HETATM   11  C8  UNL     1       1.876  -3.140   0.099  1.00  0.00           C  
HETATM   12  C9  UNL     1       0.559  -2.773   0.247  1.00  0.00           C  
HETATM   13  C10 UNL     1       0.263  -1.433   0.334  1.00  0.00           C  
HETATM   14  C11 UNL     1       1.291  -0.481   0.271  1.00  0.00           C  
HETATM   15  C12 UNL     1       2.611  -0.846   0.123  1.00  0.00           C  
HETATM   16  N1  UNL     1       3.619   0.083   0.063  1.00  0.00           N  
HETATM   17  C13 UNL     1       3.255   1.460   0.152  1.00  0.00           C  
HETATM   18  C14 UNL     1       4.911  -0.303  -0.081  1.00  0.00           C  
HETATM   19  C15 UNL     1       5.945   0.603  -0.141  1.00  0.00           C  
HETATM   20  O4  UNL     1       0.908   0.820   0.366  1.00  0.00           O  
HETATM   21  C16 UNL     1      -0.360   1.326   0.071  1.00  0.00           C  
HETATM   22  C17 UNL     1      -1.420   0.285  -0.079  1.00  0.00           C  
HETATM   23  C18 UNL     1      -1.676   0.050  -1.547  1.00  0.00           C  
HETATM   24  C19 UNL     1      -2.682   0.667   0.639  1.00  0.00           C  
HETATM   25  C20 UNL     1      -3.857   0.389   0.130  1.00  0.00           C  
HETATM   26  C21 UNL     1      -5.159   0.682   0.683  1.00  0.00           C  
HETATM   27  C22 UNL     1      -5.417   1.316   1.863  1.00  0.00           C  
HETATM   28  O5  UNL     1      -4.355   1.743   2.648  1.00  0.00           O  
HETATM   29  C23 UNL     1      -6.726   1.539   2.287  1.00  0.00           C  
HETATM   30  C24 UNL     1      -7.817   1.138   1.552  1.00  0.00           C  
HETATM   31  C25 UNL     1      -7.556   0.500   0.364  1.00  0.00           C  
HETATM   32  C26 UNL     1      -8.605   0.074  -0.419  1.00  0.00           C  
HETATM   33  C27 UNL     1      -8.319  -0.561  -1.602  1.00  0.00           C  
HETATM   34  C28 UNL     1      -7.018  -0.758  -1.978  1.00  0.00           C  
HETATM   35  O6  UNL     1      -6.741  -1.352  -3.085  1.00  0.00           O  
HETATM   36  O7  UNL     1      -6.053  -0.344  -1.217  1.00  0.00           O  
HETATM   37  C29 UNL     1      -6.270   0.267  -0.080  1.00  0.00           C  
HETATM   38  O8  UNL     1      -1.020  -0.950   0.484  1.00  0.00           O  
HETATM   39  H1  UNL     1       8.827   3.204  -0.137  1.00  0.00           H  
HETATM   40  H2  UNL     1       7.390   2.925  -1.151  1.00  0.00           H  
HETATM   41  H3  UNL     1       7.324   2.743   0.680  1.00  0.00           H  
HETATM   42  H4  UNL     1       8.630  -1.385  -0.488  1.00  0.00           H  
HETATM   43  H5  UNL     1       6.520  -4.214  -0.407  1.00  0.00           H  
HETATM   44  H6  UNL     1       2.184  -4.184   0.023  1.00  0.00           H  
HETATM   45  H7  UNL     1      -0.210  -3.509   0.292  1.00  0.00           H  
HETATM   46  H8  UNL     1       4.109   2.139   0.052  1.00  0.00           H  
HETATM   47  H9  UNL     1       2.811   1.738   1.135  1.00  0.00           H  
HETATM   48  H10 UNL     1       2.602   1.782  -0.722  1.00  0.00           H  
HETATM   49  H11 UNL     1       5.771   1.659  -0.076  1.00  0.00           H  
HETATM   50  H12 UNL     1      -0.349   1.955  -0.862  1.00  0.00           H  
HETATM   51  H13 UNL     1      -0.688   2.008   0.905  1.00  0.00           H  
HETATM   52  H14 UNL     1      -2.325   0.833  -1.991  1.00  0.00           H  
HETATM   53  H15 UNL     1      -2.129  -0.970  -1.626  1.00  0.00           H  
HETATM   54  H16 UNL     1      -0.699   0.020  -2.062  1.00  0.00           H  
HETATM   55  H17 UNL     1      -2.628   1.174   1.580  1.00  0.00           H  
HETATM   56  H18 UNL     1      -3.811  -0.127  -0.828  1.00  0.00           H  
HETATM   57  H19 UNL     1      -4.477   2.215   3.529  1.00  0.00           H  
HETATM   58  H20 UNL     1      -6.869   2.048   3.235  1.00  0.00           H  
HETATM   59  H21 UNL     1      -8.826   1.319   1.896  1.00  0.00           H  
HETATM   60  H22 UNL     1      -9.646   0.227  -0.129  1.00  0.00           H  
HETATM   61  H23 UNL     1      -9.095  -0.930  -2.283  1.00  0.00           H  
CONECT    1    2   39   40   41
CONECT    2    3
CONECT    3    4    4   19
CONECT    4    5   42
CONECT    5    6    7    7
CONECT    6   43
CONECT    7    8   18
CONECT    8    9    9   10
CONECT   10   11   11   15
CONECT   11   12   44
CONECT   12   13   13   45
CONECT   13   14   38
CONECT   14   15   15   20
CONECT   15   16
CONECT   16   17   18
CONECT   17   46   47   48
CONECT   18   19   19
CONECT   19   49
CONECT   20   21
CONECT   21   22   50   51
CONECT   22   23   24   38
CONECT   23   52   53   54
CONECT   24   25   25   55
CONECT   25   26   56
CONECT   26   27   27   37
CONECT   27   28   29
CONECT   28   57
CONECT   29   30   30   58
CONECT   30   31   59
CONECT   31   32   37   37
CONECT   32   33   33   60
CONECT   33   34   61
CONECT   34   35   35   36
CONECT   36   37
END

HMDB0040769
     RDKit          3D
Dioxinoacrimarine A
 61 66  0  0  0  0  0  0  0  0999 V2000
    7.9258    2.5564   -0.2478 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2993    1.2054   -0.3430 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2784    0.2416   -0.2862 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6001   -1.0823   -0.3751 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5635   -2.0401   -0.3165 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9338   -3.3443   -0.4092 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2481   -1.6591   -0.1724 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2142   -2.5681   -0.1097 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4359   -3.7931   -0.1845 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8964   -2.1873    0.0367 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8762   -3.1397    0.0985 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5588   -2.7726    0.2468 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2630   -1.4328    0.3341 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2911   -0.4812    0.2713 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6112   -0.8455    0.1227 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6193    0.0825    0.0630 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2554    1.4601    0.1522 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9111   -0.3029   -0.0807 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9450    0.6026   -0.1413 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9079    0.8205    0.3661 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3596    1.3260    0.0714 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4195    0.2852   -0.0785 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6756    0.0501   -1.5467 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6817    0.6672    0.6395 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8569    0.3885    0.1296 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1591    0.6820    0.6835 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4167    1.3156    1.8628 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3554    1.7425    2.6477 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7265    1.5386    2.2873 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8169    1.1385    1.5520 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5564    0.5003    0.3641 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6047    0.0744   -0.4194 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3190   -0.5606   -1.6018 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0182   -0.7576   -1.9779 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7405   -1.3522   -3.0852 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0533   -0.3443   -1.2172 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2697    0.2665   -0.0803 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0199   -0.9496    0.4842 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.8268    3.2043   -0.1370 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3896    2.9254   -1.1511 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3243    2.7426    0.6798 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.6296   -1.3847   -0.4880 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5195   -4.2144   -0.4070 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1840   -4.1838    0.0228 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2102   -3.5089    0.2924 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1094    2.1386    0.0520 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8110    1.7377    1.1347 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6021    1.7821   -0.7221 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7715    1.6590   -0.0764 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3492    1.9552   -0.8621 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6879    2.0075    0.9050 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3248    0.8333   -1.9915 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1295   -0.9701   -1.6256 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6994    0.0196   -2.0618 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6285    1.1739    1.5802 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8108   -0.1268   -0.8279 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4767    2.2148    3.5295 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8690    2.0482    3.2355 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8258    1.3193    1.8958 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.6464    0.2266   -0.1286 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0945   -0.9304   -2.2831 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
 14 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 22 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 27 29  1  0
 29 30  2  0
 30 31  1  0
 31 32  1  0
 32 33  2  0
 33 34  1  0
 34 35  2  0
 34 36  1  0
 36 37  1  0
 22 38  1  0
 19  3  1  0
 37 26  1  0
 18  7  1  0
 37 31  2  0
 15 10  1  0
 38 13  1  0
  1 39  1  0
  1 40  1  0
  1 41  1  0
  4 42  1  0
  6 43  1  0
 11 44  1  0
 12 45  1  0
 17 46  1  0
 17 47  1  0
 17 48  1  0
 19 49  1  0
 21 50  1  0
 21 51  1  0
 23 52  1  0
 23 53  1  0
 23 54  1  0
 24 55  1  0
 25 56  1  0
 28 57  1  0
 29 58  1  0
 30 59  1  0
 32 60  1  0
 33 61  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₂₉H₂₃NO₈

Average Molecular Weight

513.4948

Monoisotopic Molecular Weight

513.142366717

IUPAC Name

9-hydroxy-2-[(E)-2-(7-hydroxy-2-oxo-2H-chromen-8-yl)ethenyl]-7-methoxy-2,5-dimethyl-2,3,5,10-tetrahydro-1,4-dioxa-5-azatetraphen-10-one

Traditional Name

9-hydroxy-2-[(E)-2-(7-hydroxy-2-oxochromen-8-yl)ethenyl]-7-methoxy-2,5-dimethyl-3H-1,4-dioxa-5-azatetraphen-10-one

CAS Registry Number

158182-14-0

SMILES

COC1=CC2=C(C(O)=C1)C(=O)C1=C(N2C)C2=C(OC(C)(CO2)\C=C\C2=C(O)C=CC3=C2OC(=O)C=C3)C=C1

InChI Identifier

InChI=1S/C29H23NO8/c1-29(11-10-17-20(31)7-4-15-5-9-23(33)37-27(15)17)14-36-28-22(38-29)8-6-18-25(28)30(2)19-12-16(35-3)13-21(32)24(19)26(18)34/h4-13,31-32H,14H2,1-3H3/b11-10+

InChI Key

AEXHLHGCDOTWGS-ZHACJKMWSA-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
7-hydroxycoumarin
Hydroxycoumarin
Coumarin
Dihydroquinolone
Benzo-1,4-dioxane
Benzodioxane
Benzopyran
Dihydroquinoline
1-benzopyran
Anisole
Styrene
1-hydroxy-4-unsubstituted benzenoid
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
Pyranone
Pyran
Benzenoid
Para-dioxin
Pyridine
Vinylogous acid
Vinylogous amide
Heteroaromatic compound
Lactone
Azacycle
Ether
Oxacycle
Organic oxide
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	179 - 181 °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	0.008 g/L	ALOGPS
logP	4.46	ALOGPS
logP	5.01	ChemAxon
logS	-4.8	ALOGPS
pKa (Strongest Acidic)	7.8	ChemAxon
pKa (Strongest Basic)	-4.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	114.76 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	140.07 m³·mol⁻¹	ChemAxon
Polarizability	53.67 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	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]+	216.854	30932474
DeepCCS	[M-H]-	214.959	30932474
DeepCCS	[M-2H]-	248.199	30932474
DeepCCS	[M+Na]+	222.563	30932474
AllCCS	[M+H]+	221.6	32859911
AllCCS	[M+H-H2O]+	219.7	32859911
AllCCS	[M+NH4]+	223.5	32859911
AllCCS	[M+Na]+	224.0	32859911
AllCCS	[M-H]-	212.0	32859911
AllCCS	[M+Na-2H]-	212.1	32859911
AllCCS	[M+HCOO]-	212.3	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Dioxinoacrimarine A	COC1=CC2=C(C(O)=C1)C(=O)C1=C(N2C)C2=C(OC(C)(CO2)\C=C\C2=C(O)C=CC3=C2OC(=O)C=C3)C=C1	5821.7	Standard polar	33892256
Dioxinoacrimarine A	COC1=CC2=C(C(O)=C1)C(=O)C1=C(N2C)C2=C(OC(C)(CO2)\C=C\C2=C(O)C=CC3=C2OC(=O)C=C3)C=C1	4042.5	Standard non polar	33892256
Dioxinoacrimarine A	COC1=CC2=C(C(O)=C1)C(=O)C1=C(N2C)C2=C(OC(C)(CO2)\C=C\C2=C(O)C=CC3=C2OC(=O)C=C3)C=C1	5233.0	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Dioxinoacrimarine A,1TMS,isomer #1	COC1=CC(O[Si](C)(C)C)=C2C(=O)C3=CC=C4OC(C)(/C=C/C5=C(O)C=CC6=C5OC(=O)C=C6)COC4=C3N(C)C2=C1	4688.6	Semi standard non polar	33892256
Dioxinoacrimarine A,1TMS,isomer #2	COC1=CC(O)=C2C(=O)C3=CC=C4OC(C)(/C=C/C5=C(O[Si](C)(C)C)C=CC6=C5OC(=O)C=C6)COC4=C3N(C)C2=C1	4728.8	Semi standard non polar	33892256
Dioxinoacrimarine A,2TMS,isomer #1	COC1=CC(O[Si](C)(C)C)=C2C(=O)C3=CC=C4OC(C)(/C=C/C5=C(O[Si](C)(C)C)C=CC6=C5OC(=O)C=C6)COC4=C3N(C)C2=C1	4611.6	Semi standard non polar	33892256
Dioxinoacrimarine A,1TBDMS,isomer #1	COC1=CC(O[Si](C)(C)C(C)(C)C)=C2C(=O)C3=CC=C4OC(C)(/C=C/C5=C(O)C=CC6=C5OC(=O)C=C6)COC4=C3N(C)C2=C1	4867.6	Semi standard non polar	33892256
Dioxinoacrimarine A,1TBDMS,isomer #2	COC1=CC(O)=C2C(=O)C3=CC=C4OC(C)(/C=C/C5=C(O[Si](C)(C)C(C)(C)C)C=CC6=C5OC(=O)C=C6)COC4=C3N(C)C2=C1	4896.9	Semi standard non polar	33892256
Dioxinoacrimarine A,2TBDMS,isomer #1	COC1=CC(O[Si](C)(C)C(C)(C)C)=C2C(=O)C3=CC=C4OC(C)(/C=C/C5=C(O[Si](C)(C)C(C)(C)C)C=CC6=C5OC(=O)C=C6)COC4=C3N(C)C2=C1	5003.2	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 - Dioxinoacrimarine A GC-MS (Non-derivatized) - 70eV, Positive	splash10-001r-0110900000-e62e7f024ab1564518b9	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Dioxinoacrimarine A GC-MS (2 TMS) - 70eV, Positive	splash10-0006-0001029000-8e56a8928017f339d8f1	2017-10-06	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 - Dioxinoacrimarine A 10V, Positive-QTOF	splash10-03fs-0670390000-eefc269fe722e0d1f564	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dioxinoacrimarine A 20V, Positive-QTOF	splash10-00ds-0942710000-2a616c8257e25e9730a9	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dioxinoacrimarine A 40V, Positive-QTOF	splash10-0fi0-1590000000-492834f1c01c5e567f71	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dioxinoacrimarine A 10V, Negative-QTOF	splash10-03di-0010190000-842189e22ede48ff6c94	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dioxinoacrimarine A 20V, Negative-QTOF	splash10-03di-0130950000-bff730a74ba4f4479db4	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dioxinoacrimarine A 40V, Negative-QTOF	splash10-01dm-0291400000-d2f4668539a815b86be3	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dioxinoacrimarine A 10V, Positive-QTOF	splash10-03di-0000090000-a69c526893e2f0562b5f	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dioxinoacrimarine A 20V, Positive-QTOF	splash10-03ds-0513960000-969ee6fd96e1cf4fe893	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dioxinoacrimarine A 40V, Positive-QTOF	splash10-00ej-0951510000-db0150bf62091a1a695e	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dioxinoacrimarine A 10V, Negative-QTOF	splash10-03di-0000090000-9637a3d6c96105d420f1	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dioxinoacrimarine A 20V, Negative-QTOF	splash10-03di-0291240000-946664b885edd97a1a90	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dioxinoacrimarine A 40V, Negative-QTOF	splash10-03di-0755900000-76a0ea498ad2810dc3f1	2021-09-22	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB020585

KNApSAcK ID

C00052078

Chemspider ID

35015021

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

131752932

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 Dioxinoacrimarine A (HMDB0040769)

MOL for HMDB0040769 (Dioxinoacrimarine A)

3D MOL for HMDB0040769 (Dioxinoacrimarine A)

3D SDF for HMDB0040769 (Dioxinoacrimarine A)

3D-SDF for HMDB0040769 (Dioxinoacrimarine A)

PDB for HMDB0040769 (Dioxinoacrimarine A)

3D PDB for HMDB0040769 (Dioxinoacrimarine A)

SMILES for HMDB0040769 (Dioxinoacrimarine A)

INCHI for HMDB0040769 (Dioxinoacrimarine A)

Structure for HMDB0040769 (Dioxinoacrimarine A)

3D Structure for HMDB0040769 (Dioxinoacrimarine A)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra