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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-12 02:47:41 UTC

Update Date

2022-03-07 02:56:54 UTC

HMDB ID

HMDB0041141

Secondary Accession Numbers

HMDB41141

Metabolite Identification

Common Name

Marshdine

Description

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

Structure

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

HMDB0041141
     RDKit          3D
Marshdine
 35 38  0  0  0  0  0  0  0  0999 V2000
    4.8512    1.1890    0.7267 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4807   -0.1134    1.0913 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1797   -0.6026    0.9440 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8570   -1.8790    1.3111 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5466   -2.3891    1.1689 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2755   -3.6652    1.5485 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5517   -1.5878    0.6457 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7496   -2.0146    0.4812 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0985   -3.1760    0.8021 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7457   -1.1953   -0.0441 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0416   -1.6476   -0.1929 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0451   -0.8539   -0.7054 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6838    0.4242   -1.0638 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3772    0.8822   -0.9146 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3799    0.0828   -0.4020 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1122    0.4986   -0.2424 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3088    1.8159   -0.6165 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8726   -0.3003    0.2740 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1660    0.1768    0.4239 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4143    2.1755   -1.3715 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7158    2.6322   -1.5609 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4747    1.4367   -1.6016 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4093    1.4720   -0.2525 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9302    1.3304    0.7561 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4072    1.8818    1.4864 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6068   -2.5366    1.7241 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5679   -4.2879    1.5931 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2984   -2.6577    0.0972 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0618   -1.2128   -0.8209 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2039    1.7168   -1.3129 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3833    2.4467   -1.1612 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7450    2.3093    0.2835 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4295    1.1871    0.1412 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8110    3.1760   -2.5223 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9967    3.2860   -0.7131 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
 19  3  1  0
 18  7  1  0
 15 10  1  0
 22 13  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  4 26  1  0
  6 27  1  0
 11 28  1  0
 12 29  1  0
 17 30  1  0
 17 31  1  0
 17 32  1  0
 19 33  1  0
 21 34  1  0
 21 35  1  0
M  END


  Mrv0541 05061312252D          

 22 25  0  0  0  0            999 V2000
    2.4510   -3.0759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2303   -2.9770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8377   -0.2846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0319   -0.4617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0625   -2.7218    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1179   -1.7584    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1228   -2.4086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8683   -2.5447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3939   -0.8939    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5063   -2.1125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5616   -1.1491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7823   -1.2480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7559   -1.3261    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1443   -1.6803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1996   -0.7168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3385   -1.8573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7005   -2.2895    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.8112   -0.3627    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4492    0.0695    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4245   -3.1540    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0310   -1.5887    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9309   -2.5746    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  2  0  0  0  0
  8  5  2  0  0  0  0
  8  6  1  0  0  0  0
  9  3  1  0  0  0  0
 10  5  1  0  0  0  0
 11  6  2  0  0  0  0
 12  4  1  0  0  0  0
 13 10  2  0  0  0  0
 13 11  1  0  0  0  0
 14  9  2  0  0  0  0
 15  9  1  0  0  0  0
 15 13  1  0  0  0  0
 16 12  2  0  0  0  0
 16 14  1  0  0  0  0
 17  1  1  0  0  0  0
 17 10  1  0  0  0  0
 17 14  1  0  0  0  0
 18 11  1  0  0  0  0
 19 15  2  0  0  0  0
 20  2  1  0  0  0  0
 20  8  1  0  0  0  0
 21  7  1  0  0  0  0
 21 12  1  0  0  0  0
 22  7  1  0  0  0  0
 22 16  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0041141

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=CC2=C(C(O)=C1)C(=O)C1=C(N2C)C2=C(OCO2)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C16H13NO5/c1-17-10-5-8(20-2)6-11(18)13(10)15(19)9-3-4-12-16(14(9)17)22-7-21-12/h3-6,18H,7H2,1-2H3

> <INCHI_KEY>
HIDPWENUZOGSOF-UHFFFAOYSA-N

> <FORMULA>
C16H13NO5

> <MOLECULAR_WEIGHT>
299.2781

> <EXACT_MASS>
299.079372531

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
30.097261506977347

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
7-hydroxy-9-methoxy-11-methyl-2H,6H,11H-[1,3]dioxolo[4,5-c]acridin-6-one

> <ALOGPS_LOGP>
2.04

> <JCHEM_LOGP>
2.9349517586666667

> <ALOGPS_LOGS>
-2.66

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.033557165062076

> <JCHEM_PKA_STRONGEST_BASIC>
-4.194581659474292

> <JCHEM_POLAR_SURFACE_AREA>
68.23

> <JCHEM_REFRACTIVITY>
78.16940000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.62e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
7-hydroxy-9-methoxy-11-methyl-2H-[1,3]dioxolo[4,5-c]acridin-6-one

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0041141
     RDKit          3D
Marshdine
 35 38  0  0  0  0  0  0  0  0999 V2000
    4.8512    1.1890    0.7267 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4807   -0.1134    1.0913 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1797   -0.6026    0.9440 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8570   -1.8790    1.3111 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5466   -2.3891    1.1689 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2755   -3.6652    1.5485 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5517   -1.5878    0.6457 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7496   -2.0146    0.4812 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0985   -3.1760    0.8021 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7457   -1.1953   -0.0441 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0416   -1.6476   -0.1929 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0451   -0.8539   -0.7054 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6838    0.4242   -1.0638 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3772    0.8822   -0.9146 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3799    0.0828   -0.4020 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1122    0.4986   -0.2424 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3088    1.8159   -0.6165 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8726   -0.3003    0.2740 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1660    0.1768    0.4239 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4143    2.1755   -1.3715 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7158    2.6322   -1.5609 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4747    1.4367   -1.6016 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4093    1.4720   -0.2525 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9302    1.3304    0.7561 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4072    1.8818    1.4864 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6068   -2.5366    1.7241 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5679   -4.2879    1.5931 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2984   -2.6577    0.0972 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0618   -1.2128   -0.8209 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2039    1.7168   -1.3129 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3833    2.4467   -1.1612 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7450    2.3093    0.2835 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4295    1.1871    0.1412 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8110    3.1760   -2.5223 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9967    3.2860   -0.7131 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
 19  3  1  0
 18  7  1  0
 15 10  1  0
 22 13  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  4 26  1  0
  6 27  1  0
 11 28  1  0
 12 29  1  0
 17 30  1  0
 17 31  1  0
 17 32  1  0
 19 33  1  0
 21 34  1  0
 21 35  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       4.575  -5.742   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      11.630  -5.557   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.430  -0.531   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.926  -0.862   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.583  -5.081   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.553  -3.282   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.229  -4.496   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.087  -4.750   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.469  -1.669   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.545  -3.943   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.515  -2.145   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.460  -2.330   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.011  -2.475   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.003  -3.137   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.973  -1.338   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.499  -3.467   0.000  0.00  0.00           C+0
HETATM   17  N   UNK     0       5.041  -4.274   0.000  0.00  0.00           N+0
HETATM   18  O   UNK     0       8.981  -0.677   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       6.439   0.130   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      10.126  -5.887   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       0.058  -2.966   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       1.738  -4.806   0.000  0.00  0.00           O+0
CONECT    1   17                                                            
CONECT    2   20                                                            
CONECT    3    4    9                                                       
CONECT    4    3   12                                                       
CONECT    5    8   10                                                       
CONECT    6    8   11                                                       
CONECT    7   21   22                                                       
CONECT    8    5    6   20                                                  
CONECT    9    3   14   15                                                  
CONECT   10    5   13   17                                                  
CONECT   11    6   13   18                                                  
CONECT   12    4   16   21                                                  
CONECT   13   10   11   15                                                  
CONECT   14    9   16   17                                                  
CONECT   15    9   13   19                                                  
CONECT   16   12   14   22                                                  
CONECT   17    1   10   14                                                  
CONECT   18   11                                                            
CONECT   19   15                                                            
CONECT   20    2    8                                                       
CONECT   21    7   12                                                       
CONECT   22    7   16                                                       
MASTER        0    0    0    0    0    0    0    0   22    0   50    0
END

COMPND    HMDB0041141
HETATM    1  C1  UNL     1       4.851   1.189   0.727  1.00  0.00           C  
HETATM    2  O1  UNL     1       4.481  -0.113   1.091  1.00  0.00           O  
HETATM    3  C2  UNL     1       3.180  -0.603   0.944  1.00  0.00           C  
HETATM    4  C3  UNL     1       2.857  -1.879   1.311  1.00  0.00           C  
HETATM    5  C4  UNL     1       1.547  -2.389   1.169  1.00  0.00           C  
HETATM    6  O2  UNL     1       1.275  -3.665   1.549  1.00  0.00           O  
HETATM    7  C5  UNL     1       0.552  -1.588   0.646  1.00  0.00           C  
HETATM    8  C6  UNL     1      -0.750  -2.015   0.481  1.00  0.00           C  
HETATM    9  O3  UNL     1      -1.098  -3.176   0.802  1.00  0.00           O  
HETATM   10  C7  UNL     1      -1.746  -1.195  -0.044  1.00  0.00           C  
HETATM   11  C8  UNL     1      -3.042  -1.648  -0.193  1.00  0.00           C  
HETATM   12  C9  UNL     1      -4.045  -0.854  -0.705  1.00  0.00           C  
HETATM   13  C10 UNL     1      -3.684   0.424  -1.064  1.00  0.00           C  
HETATM   14  C11 UNL     1      -2.377   0.882  -0.915  1.00  0.00           C  
HETATM   15  C12 UNL     1      -1.380   0.083  -0.402  1.00  0.00           C  
HETATM   16  N1  UNL     1      -0.112   0.499  -0.242  1.00  0.00           N  
HETATM   17  C13 UNL     1       0.309   1.816  -0.617  1.00  0.00           C  
HETATM   18  C14 UNL     1       0.873  -0.300   0.274  1.00  0.00           C  
HETATM   19  C15 UNL     1       2.166   0.177   0.424  1.00  0.00           C  
HETATM   20  O4  UNL     1      -2.414   2.175  -1.372  1.00  0.00           O  
HETATM   21  C16 UNL     1      -3.716   2.632  -1.561  1.00  0.00           C  
HETATM   22  O5  UNL     1      -4.475   1.437  -1.602  1.00  0.00           O  
HETATM   23  H1  UNL     1       4.409   1.472  -0.253  1.00  0.00           H  
HETATM   24  H2  UNL     1       5.930   1.330   0.756  1.00  0.00           H  
HETATM   25  H3  UNL     1       4.407   1.882   1.486  1.00  0.00           H  
HETATM   26  H4  UNL     1       3.607  -2.537   1.724  1.00  0.00           H  
HETATM   27  H5  UNL     1       0.568  -4.288   1.593  1.00  0.00           H  
HETATM   28  H6  UNL     1      -3.298  -2.658   0.097  1.00  0.00           H  
HETATM   29  H7  UNL     1      -5.062  -1.213  -0.821  1.00  0.00           H  
HETATM   30  H8  UNL     1       1.204   1.717  -1.313  1.00  0.00           H  
HETATM   31  H9  UNL     1      -0.383   2.447  -1.161  1.00  0.00           H  
HETATM   32  H10 UNL     1       0.745   2.309   0.283  1.00  0.00           H  
HETATM   33  H11 UNL     1       2.429   1.187   0.141  1.00  0.00           H  
HETATM   34  H12 UNL     1      -3.811   3.176  -2.522  1.00  0.00           H  
HETATM   35  H13 UNL     1      -3.997   3.286  -0.713  1.00  0.00           H  
CONECT    1    2   23   24   25
CONECT    2    3
CONECT    3    4    4   19
CONECT    4    5   26
CONECT    5    6    7    7
CONECT    6   27
CONECT    7    8   18
CONECT    8    9    9   10
CONECT   10   11   11   15
CONECT   11   12   28
CONECT   12   13   13   29
CONECT   13   14   22
CONECT   14   15   15   20
CONECT   15   16
CONECT   16   17   18
CONECT   17   30   31   32
CONECT   18   19   19
CONECT   19   33
CONECT   20   21
CONECT   21   22   34   35
END

HMDB0041141
     RDKit          3D
Marshdine
 35 38  0  0  0  0  0  0  0  0999 V2000
    4.8512    1.1890    0.7267 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4807   -0.1134    1.0913 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1797   -0.6026    0.9440 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8570   -1.8790    1.3111 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5466   -2.3891    1.1689 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2755   -3.6652    1.5485 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5517   -1.5878    0.6457 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7496   -2.0146    0.4812 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0985   -3.1760    0.8021 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7457   -1.1953   -0.0441 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0416   -1.6476   -0.1929 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0451   -0.8539   -0.7054 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6838    0.4242   -1.0638 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3772    0.8822   -0.9146 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3799    0.0828   -0.4020 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1122    0.4986   -0.2424 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3088    1.8159   -0.6165 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8726   -0.3003    0.2740 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1660    0.1768    0.4239 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4143    2.1755   -1.3715 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7158    2.6322   -1.5609 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4747    1.4367   -1.6016 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4093    1.4720   -0.2525 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9302    1.3304    0.7561 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4072    1.8818    1.4864 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6068   -2.5366    1.7241 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5679   -4.2879    1.5931 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2984   -2.6577    0.0972 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0618   -1.2128   -0.8209 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2039    1.7168   -1.3129 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3833    2.4467   -1.1612 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7450    2.3093    0.2835 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4295    1.1871    0.1412 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8110    3.1760   -2.5223 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9967    3.2860   -0.7131 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
 19  3  1  0
 18  7  1  0
 15 10  1  0
 22 13  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  4 26  1  0
  6 27  1  0
 11 28  1  0
 12 29  1  0
 17 30  1  0
 17 31  1  0
 17 32  1  0
 19 33  1  0
 21 34  1  0
 21 35  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
1-Hydroxy-3-methoxy-10-methyl-5,6-methylenedioxyacridone	HMDB
2-Hydroxy-2-(1-methoxy-1-methylethyl)-5-methylcyclohexanone	HMDB

Chemical Formula

C₁₆H₁₃NO₅

Average Molecular Weight

299.2781

Monoisotopic Molecular Weight

299.079372531

IUPAC Name

7-hydroxy-9-methoxy-11-methyl-2H,6H,11H-[1,3]dioxolo[4,5-c]acridin-6-one

Traditional Name

7-hydroxy-9-methoxy-11-methyl-2H-[1,3]dioxolo[4,5-c]acridin-6-one

CAS Registry Number

160927-87-7

SMILES

COC1=CC2=C(C(O)=C1)C(=O)C1=C(N2C)C2=C(OCO2)C=C1

InChI Identifier

InChI=1S/C16H13NO5/c1-17-10-5-8(20-2)6-11(18)13(10)15(19)9-3-4-12-16(14(9)17)22-7-21-12/h3-6,18H,7H2,1-2H3

InChI Key

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

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0041141)
Cytoplasm (HMDB: HMDB0041141)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0041141)

Source

Exogenous

Food

Food (HMDB: HMDB0041141)

Fruit

Citrus

Citrus (FooDB: FOOD00859)

Endogenous

Plant

Plant (HMDB: HMDB0041141)

Not Available

Nutrient (HMDB: HMDB0041141)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	210 - 213 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	10.03 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.66 g/L	ALOGPS
logP	2.04	ALOGPS
logP	2.93	ChemAxon
logS	-2.7	ALOGPS
pKa (Strongest Acidic)	10.03	ChemAxon
pKa (Strongest Basic)	-4.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	68.23 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	78.17 m³·mol⁻¹	ChemAxon
Polarizability	30.1 Å³	ChemAxon
Number of Rings	4	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]+	169.37	31661259
DarkChem	[M-H]-	169.868	31661259
DeepCCS	[M+H]+	171.69	30932474
DeepCCS	[M-H]-	169.332	30932474
DeepCCS	[M-2H]-	203.561	30932474
DeepCCS	[M+Na]+	178.959	30932474
AllCCS	[M+H]+	166.6	32859911
AllCCS	[M+H-H2O]+	162.9	32859911
AllCCS	[M+NH4]+	170.0	32859911
AllCCS	[M+Na]+	171.0	32859911
AllCCS	[M-H]-	171.7	32859911
AllCCS	[M+Na-2H]-	170.8	32859911
AllCCS	[M+HCOO]-	169.9	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Marshdine	COC1=CC2=C(C(O)=C1)C(=O)C1=C(N2C)C2=C(OCO2)C=C1	3611.0	Standard polar	33892256
Marshdine	COC1=CC2=C(C(O)=C1)C(=O)C1=C(N2C)C2=C(OCO2)C=C1	2701.8	Standard non polar	33892256
Marshdine	COC1=CC2=C(C(O)=C1)C(=O)C1=C(N2C)C2=C(OCO2)C=C1	3233.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Marshdine,1TMS,isomer #1	COC1=CC(O[Si](C)(C)C)=C2C(=O)C3=CC=C4OCOC4=C3N(C)C2=C1	2975.7	Semi standard non polar	33892256
Marshdine,1TBDMS,isomer #1	COC1=CC(O[Si](C)(C)C(C)(C)C)=C2C(=O)C3=CC=C4OCOC4=C3N(C)C2=C1	3137.1	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 - Marshdine GC-MS (Non-derivatized) - 70eV, Positive	splash10-00c1-0490000000-293b691dfa2bd1672e01	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Marshdine GC-MS (1 TMS) - 70eV, Positive	splash10-0ab9-3159000000-8f84025e4008371a70e2	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Marshdine 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 - Marshdine 10V, Positive-QTOF	splash10-0udi-0029000000-fefe302b3f4f55ede464	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Marshdine 20V, Positive-QTOF	splash10-0udi-0079000000-0f70ce2d82efe63d1c97	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Marshdine 40V, Positive-QTOF	splash10-0udl-0190000000-7053595912f4be3c3fc2	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Marshdine 10V, Negative-QTOF	splash10-0002-0090000000-87d4f8ea8de87d1a28b5	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Marshdine 20V, Negative-QTOF	splash10-0002-0090000000-0ca33c374a2efd6332f2	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Marshdine 40V, Negative-QTOF	splash10-00r5-3690000000-b4256b997b18ec85101f	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Marshdine 10V, Positive-QTOF	splash10-0udi-0009000000-4e7790846d848550c25a	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Marshdine 20V, Positive-QTOF	splash10-0udi-0009000000-4e7790846d848550c25a	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Marshdine 40V, Positive-QTOF	splash10-0uk9-0290000000-6f18e856ce02d0e0add6	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Marshdine 10V, Negative-QTOF	splash10-0002-0090000000-9de0712e4e64a21b3eca	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Marshdine 20V, Negative-QTOF	splash10-0002-0090000000-9de0712e4e64a21b3eca	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Marshdine 40V, Negative-QTOF	splash10-00xu-0290000000-2b74c2def58cd6379fb5	2021-09-23	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

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

FDB021027

KNApSAcK ID

C00024264

Chemspider ID

30777539

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

131753041

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1889911

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 Marshdine (HMDB0041141)

MOL for HMDB0041141 (Marshdine)

3D MOL for HMDB0041141 (Marshdine)

3D SDF for HMDB0041141 (Marshdine)

3D-SDF for HMDB0041141 (Marshdine)

PDB for HMDB0041141 (Marshdine)

3D PDB for HMDB0041141 (Marshdine)

SMILES for HMDB0041141 (Marshdine)

INCHI for HMDB0041141 (Marshdine)

Structure for HMDB0041141 (Marshdine)

3D Structure for HMDB0041141 (Marshdine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra