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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-12 02:43:57 UTC

Update Date

2022-03-07 02:56:52 UTC

HMDB ID

HMDB0041087

Secondary Accession Numbers

HMDB41087

Metabolite Identification

Common Name

Furoparadine

Description

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

Structure

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

HMDB0041087
     RDKit          3D
Furoparadine
 36 39  0  0  0  0  0  0  0  0999 V2000
    3.3833   -1.8542    0.6848 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6391   -0.7713    1.1999 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2365    0.2470    0.3708 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2629    1.1604   -0.0198 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5513    0.9279    0.4529 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9663    2.2142   -0.8271 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6814    2.3876   -1.2556 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6819    1.4898   -0.8668 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6161    1.7590   -1.2410 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8290    2.7468   -1.9943 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6739    0.9868   -0.8190 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9630    1.2911   -1.1445 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2855    2.3216   -1.9532 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9773    0.4888   -0.6076 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6834   -0.5575    0.2151 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4584   -1.4207    0.8488 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7474   -2.2473    1.5574 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4072   -1.9521    1.4118 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3741   -0.8832    0.5493 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3684   -0.1071    0.0185 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0672   -0.3445    0.3498 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.2555   -1.6383    0.9076 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9642    0.4148   -0.0519 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3638   -1.7936   -0.4204 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4566   -1.6562    0.9510 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0747   -2.8371    1.0938 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3267    1.5093    0.2337 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7745    2.9025   -1.1145 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4476    3.2203   -1.8936 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8586    3.0127   -2.4513 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9974    0.7397   -0.8767 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2065   -3.0422    2.1619 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6795   -2.4903    1.9587 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5044   -1.7648    1.9014 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0747   -2.0034    0.1415 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4526   -2.4563    0.5286 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  4  6  1  0
  6  7  2  0
  7  8  1  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  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  1  0
 21 23  1  0
 23  3  1  0
 23  8  2  0
 20 11  1  0
 19 15  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  5 27  1  0
  6 28  1  0
  7 29  1  0
 13 30  1  0
 14 31  1  0
 17 32  1  0
 18 33  1  0
 22 34  1  0
 22 35  1  0
 22 36  1  0
M  END


  Mrv0541 05061312222D          

 23 26  0  0  0  0            999 V2000
    1.8611   -1.9655    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0571   -3.0070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2496   -0.0386    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8058   -0.6479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3811   -1.4641    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1893   -1.2981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2802    0.6488    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9736   -0.7469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5562   -0.2157    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5562   -1.4343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4744    0.8258    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5298   -0.1376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9182    0.2165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1678   -0.5698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8058   -1.0021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1124    0.3936    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2496   -1.6114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6116   -1.1791    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1124   -2.0436    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2249    1.6122    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8629    1.1799    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4991   -2.3977    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2811   -0.4783    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  2  0  0  0  0
  6  5  2  0  0  0  0
  8  5  1  0  0  0  0
  9  3  1  0  0  0  0
 10  4  1  0  0  0  0
 11  7  2  0  0  0  0
 12  7  1  0  0  0  0
 12  8  2  0  0  0  0
 13 11  1  0  0  0  0
 14  8  1  0  0  0  0
 14 13  2  0  0  0  0
 15  9  2  0  0  0  0
 16  9  1  0  0  0  0
 16 13  1  0  0  0  0
 17 10  2  0  0  0  0
 17 15  1  0  0  0  0
 18  1  1  0  0  0  0
 18 14  1  0  0  0  0
 18 15  1  0  0  0  0
 19 10  1  0  0  0  0
 20 11  1  0  0  0  0
 21 16  2  0  0  0  0
 22  2  1  0  0  0  0
 22 17  1  0  0  0  0
 23  6  1  0  0  0  0
 23 12  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0041087

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=C(O)C=CC2=C1N(C)C1=C(C(O)=CC3=C1C=CO3)C2=O

> <INCHI_IDENTIFIER>
InChI=1S/C17H13NO5/c1-18-14-8-5-6-23-12(8)7-11(20)13(14)16(21)9-3-4-10(19)17(22-2)15(9)18/h3-7,19-20H,1-2H3

> <INCHI_KEY>
YVQYEEOGMKSXAW-UHFFFAOYSA-N

> <FORMULA>
C17H13NO5

> <MOLECULAR_WEIGHT>
311.2888

> <EXACT_MASS>
311.079372531

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
30.82239110425333

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5,9-dihydroxy-10-methoxy-11-methyl-6H,11H-furo[2,3-c]acridin-6-one

> <ALOGPS_LOGP>
2.96

> <JCHEM_LOGP>
3.1672763699999997

> <ALOGPS_LOGS>
-2.67

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.28350157080984

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.380117607788558

> <JCHEM_PKA_STRONGEST_BASIC>
-2.30165455447051

> <JCHEM_POLAR_SURFACE_AREA>
83.14

> <JCHEM_REFRACTIVITY>
83.22449999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.71e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5,9-dihydroxy-10-methoxy-11-methylfuro[2,3-c]acridin-6-one

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0041087
     RDKit          3D
Furoparadine
 36 39  0  0  0  0  0  0  0  0999 V2000
    3.3833   -1.8542    0.6848 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6391   -0.7713    1.1999 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2365    0.2470    0.3708 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2629    1.1604   -0.0198 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5513    0.9279    0.4529 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9663    2.2142   -0.8271 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6814    2.3876   -1.2556 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6819    1.4898   -0.8668 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6161    1.7590   -1.2410 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8290    2.7468   -1.9943 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6739    0.9868   -0.8190 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9630    1.2911   -1.1445 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2855    2.3216   -1.9532 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9773    0.4888   -0.6076 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6834   -0.5575    0.2151 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4584   -1.4207    0.8488 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7474   -2.2473    1.5574 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4072   -1.9521    1.4118 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3741   -0.8832    0.5493 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3684   -0.1071    0.0185 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0672   -0.3445    0.3498 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.2555   -1.6383    0.9076 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9642    0.4148   -0.0519 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3638   -1.7936   -0.4204 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4566   -1.6562    0.9510 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0747   -2.8371    1.0938 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3267    1.5093    0.2337 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7745    2.9025   -1.1145 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4476    3.2203   -1.8936 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8586    3.0127   -2.4513 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9974    0.7397   -0.8767 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2065   -3.0422    2.1619 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6795   -2.4903    1.9587 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5044   -1.7648    1.9014 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0747   -2.0034    0.1415 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4526   -2.4563    0.5286 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  4  6  1  0
  6  7  2  0
  7  8  1  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  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  1  0
 21 23  1  0
 23  3  1  0
 23  8  2  0
 20 11  1  0
 19 15  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  5 27  1  0
  6 28  1  0
  7 29  1  0
 13 30  1  0
 14 31  1  0
 17 32  1  0
 18 33  1  0
 22 34  1  0
 22 35  1  0
 22 36  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       3.474  -3.669   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.107  -5.613   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.466  -0.072   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.504  -1.209   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.311  -2.733   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.820  -2.423   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.123   1.211   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.551  -1.394   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.038  -0.403   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.038  -2.677   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.619   1.541   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.589  -0.257   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.581   0.404   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.047  -1.064   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.504  -1.871   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.076   0.735   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.466  -3.008   0.000  0.00  0.00           C+0
HETATM   18  N   UNK     0       3.008  -2.201   0.000  0.00  0.00           N+0
HETATM   19  O   UNK     0      -2.076  -3.815   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       4.153   3.009   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       1.611   2.202   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       0.932  -4.476   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       7.991  -0.893   0.000  0.00  0.00           O+0
CONECT    1   18                                                            
CONECT    2   22                                                            
CONECT    3    4    9                                                       
CONECT    4    3   10                                                       
CONECT    5    6    8                                                       
CONECT    6    5   23                                                       
CONECT    7   11   12                                                       
CONECT    8    5   12   14                                                  
CONECT    9    3   15   16                                                  
CONECT   10    4   17   19                                                  
CONECT   11    7   13   20                                                  
CONECT   12    7    8   23                                                  
CONECT   13   11   14   16                                                  
CONECT   14    8   13   18                                                  
CONECT   15    9   17   18                                                  
CONECT   16    9   13   21                                                  
CONECT   17   10   15   22                                                  
CONECT   18    1   14   15                                                  
CONECT   19   10                                                            
CONECT   20   11                                                            
CONECT   21   16                                                            
CONECT   22    2   17                                                       
CONECT   23    6   12                                                       
MASTER        0    0    0    0    0    0    0    0   23    0   52    0
END

COMPND    HMDB0041087
HETATM    1  C1  UNL     1       3.383  -1.854   0.685  1.00  0.00           C  
HETATM    2  O1  UNL     1       2.639  -0.771   1.200  1.00  0.00           O  
HETATM    3  C2  UNL     1       2.237   0.247   0.371  1.00  0.00           C  
HETATM    4  C3  UNL     1       3.263   1.160  -0.020  1.00  0.00           C  
HETATM    5  O2  UNL     1       4.551   0.928   0.453  1.00  0.00           O  
HETATM    6  C4  UNL     1       2.966   2.214  -0.827  1.00  0.00           C  
HETATM    7  C5  UNL     1       1.681   2.388  -1.256  1.00  0.00           C  
HETATM    8  C6  UNL     1       0.682   1.490  -0.867  1.00  0.00           C  
HETATM    9  C7  UNL     1      -0.616   1.759  -1.241  1.00  0.00           C  
HETATM   10  O3  UNL     1      -0.829   2.747  -1.994  1.00  0.00           O  
HETATM   11  C8  UNL     1      -1.674   0.987  -0.819  1.00  0.00           C  
HETATM   12  C9  UNL     1      -2.963   1.291  -1.144  1.00  0.00           C  
HETATM   13  O4  UNL     1      -3.286   2.322  -1.953  1.00  0.00           O  
HETATM   14  C10 UNL     1      -3.977   0.489  -0.608  1.00  0.00           C  
HETATM   15  C11 UNL     1      -3.683  -0.558   0.215  1.00  0.00           C  
HETATM   16  O5  UNL     1      -4.458  -1.421   0.849  1.00  0.00           O  
HETATM   17  C12 UNL     1      -3.747  -2.247   1.557  1.00  0.00           C  
HETATM   18  C13 UNL     1      -2.407  -1.952   1.412  1.00  0.00           C  
HETATM   19  C14 UNL     1      -2.374  -0.883   0.549  1.00  0.00           C  
HETATM   20  C15 UNL     1      -1.368  -0.107   0.018  1.00  0.00           C  
HETATM   21  N1  UNL     1      -0.067  -0.345   0.350  1.00  0.00           N  
HETATM   22  C16 UNL     1       0.255  -1.638   0.908  1.00  0.00           C  
HETATM   23  C17 UNL     1       0.964   0.415  -0.052  1.00  0.00           C  
HETATM   24  H1  UNL     1       3.364  -1.794  -0.420  1.00  0.00           H  
HETATM   25  H2  UNL     1       4.457  -1.656   0.951  1.00  0.00           H  
HETATM   26  H3  UNL     1       3.075  -2.837   1.094  1.00  0.00           H  
HETATM   27  H4  UNL     1       5.327   1.509   0.234  1.00  0.00           H  
HETATM   28  H5  UNL     1       3.775   2.902  -1.114  1.00  0.00           H  
HETATM   29  H6  UNL     1       1.448   3.220  -1.894  1.00  0.00           H  
HETATM   30  H7  UNL     1      -2.859   3.013  -2.451  1.00  0.00           H  
HETATM   31  H8  UNL     1      -4.997   0.740  -0.877  1.00  0.00           H  
HETATM   32  H9  UNL     1      -4.207  -3.042   2.162  1.00  0.00           H  
HETATM   33  H10 UNL     1      -1.679  -2.490   1.959  1.00  0.00           H  
HETATM   34  H11 UNL     1       0.504  -1.765   1.901  1.00  0.00           H  
HETATM   35  H12 UNL     1       1.075  -2.003   0.142  1.00  0.00           H  
HETATM   36  H13 UNL     1      -0.453  -2.456   0.529  1.00  0.00           H  
CONECT    1    2   24   25   26
CONECT    2    3
CONECT    3    4    4   23
CONECT    4    5    6
CONECT    5   27
CONECT    6    7    7   28
CONECT    7    8   29
CONECT    8    9   23   23
CONECT    9   10   10   11
CONECT   11   12   12   20
CONECT   12   13   14
CONECT   13   30
CONECT   14   15   15   31
CONECT   15   16   19
CONECT   16   17
CONECT   17   18   18   32
CONECT   18   19   33
CONECT   19   20   20
CONECT   20   21
CONECT   21   22   23
CONECT   22   34   35   36
END

HMDB0041087
     RDKit          3D
Furoparadine
 36 39  0  0  0  0  0  0  0  0999 V2000
    3.3833   -1.8542    0.6848 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6391   -0.7713    1.1999 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2365    0.2470    0.3708 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2629    1.1604   -0.0198 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5513    0.9279    0.4529 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9663    2.2142   -0.8271 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6814    2.3876   -1.2556 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6819    1.4898   -0.8668 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6161    1.7590   -1.2410 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8290    2.7468   -1.9943 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6739    0.9868   -0.8190 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9630    1.2911   -1.1445 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2855    2.3216   -1.9532 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9773    0.4888   -0.6076 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6834   -0.5575    0.2151 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4584   -1.4207    0.8488 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7474   -2.2473    1.5574 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4072   -1.9521    1.4118 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3741   -0.8832    0.5493 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3684   -0.1071    0.0185 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0672   -0.3445    0.3498 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.2555   -1.6383    0.9076 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9642    0.4148   -0.0519 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3638   -1.7936   -0.4204 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4566   -1.6562    0.9510 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0747   -2.8371    1.0938 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3267    1.5093    0.2337 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7745    2.9025   -1.1145 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4476    3.2203   -1.8936 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8586    3.0127   -2.4513 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9974    0.7397   -0.8767 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2065   -3.0422    2.1619 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6795   -2.4903    1.9587 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5044   -1.7648    1.9014 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0747   -2.0034    0.1415 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4526   -2.4563    0.5286 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  4  6  1  0
  6  7  2  0
  7  8  1  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  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  1  0
 21 23  1  0
 23  3  1  0
 23  8  2  0
 20 11  1  0
 19 15  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  5 27  1  0
  6 28  1  0
  7 29  1  0
 13 30  1  0
 14 31  1  0
 17 32  1  0
 18 33  1  0
 22 34  1  0
 22 35  1  0
 22 36  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₁₇H₁₃NO₅

Average Molecular Weight

311.2888

Monoisotopic Molecular Weight

311.079372531

IUPAC Name

5,9-dihydroxy-10-methoxy-11-methyl-6H,11H-furo[2,3-c]acridin-6-one

Traditional Name

5,9-dihydroxy-10-methoxy-11-methylfuro[2,3-c]acridin-6-one

CAS Registry Number

161161-72-4

SMILES

COC1=C(O)C=CC2=C1N(C)C1=C(C(O)=CC3=C1C=CO3)C2=O

InChI Identifier

InChI=1S/C17H13NO5/c1-18-14-8-5-6-23-12(8)7-11(20)13(14)16(21)9-3-4-10(19)17(22-2)15(9)18/h3-7,19-20H,1-2H3

InChI Key

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

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0041087)
Cell membrane (HMDB: HMDB0041087)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0041087)

Source

Exogenous

Exogenous (HMDB: HMDB0041087)

Food

Food (HMDB: HMDB0041087)

Fruit

Citrus

Citrus (FooDB: FOOD00859)

Endogenous

Plant

Plant (HMDB: HMDB0041087)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0041087)

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	27.94 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	0.67 g/L	ALOGPS
logP	2.96	ALOGPS
logP	3.17	ChemAxon
logS	-2.7	ALOGPS
pKa (Strongest Acidic)	8.38	ChemAxon
pKa (Strongest Basic)	-2.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	83.14 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	83.22 m³·mol⁻¹	ChemAxon
Polarizability	30.82 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]+	171.671	31661259
DarkChem	[M-H]-	170.388	31661259
DeepCCS	[M+H]+	174.073	30932474
DeepCCS	[M-H]-	171.715	30932474
DeepCCS	[M-2H]-	205.633	30932474
DeepCCS	[M+Na]+	180.86	30932474
AllCCS	[M+H]+	169.8	32859911
AllCCS	[M+H-H2O]+	166.2	32859911
AllCCS	[M+NH4]+	173.1	32859911
AllCCS	[M+Na]+	174.1	32859911
AllCCS	[M-H]-	173.9	32859911
AllCCS	[M+Na-2H]-	173.0	32859911
AllCCS	[M+HCOO]-	172.1	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	5.86 minutes	32390414
Predicted by Siyang on May 30, 2022	10.8089 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.31 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1820.3 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	243.8 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	115.6 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	159.0 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	110.1 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	405.6 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	436.7 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	236.0 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	715.5 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	295.1 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1165.7 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	256.2 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	342.3 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	448.2 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	399.4 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	95.9 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Furoparadine	COC1=C(O)C=CC2=C1N(C)C1=C(C(O)=CC3=C1C=CO3)C2=O	3967.2	Standard polar	33892256
Furoparadine	COC1=C(O)C=CC2=C1N(C)C1=C(C(O)=CC3=C1C=CO3)C2=O	2656.1	Standard non polar	33892256
Furoparadine	COC1=C(O)C=CC2=C1N(C)C1=C(C(O)=CC3=C1C=CO3)C2=O	3224.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Furoparadine,1TMS,isomer #1	COC1=C(O[Si](C)(C)C)C=CC2=C1N(C)C1=C3C=COC3=CC(O)=C1C2=O	3221.6	Semi standard non polar	33892256
Furoparadine,1TMS,isomer #2	COC1=C(O)C=CC2=C1N(C)C1=C3C=COC3=CC(O[Si](C)(C)C)=C1C2=O	3284.5	Semi standard non polar	33892256
Furoparadine,2TMS,isomer #1	COC1=C(O[Si](C)(C)C)C=CC2=C1N(C)C1=C3C=COC3=CC(O[Si](C)(C)C)=C1C2=O	3288.4	Semi standard non polar	33892256
Furoparadine,1TBDMS,isomer #1	COC1=C(O[Si](C)(C)C(C)(C)C)C=CC2=C1N(C)C1=C3C=COC3=CC(O)=C1C2=O	3436.4	Semi standard non polar	33892256
Furoparadine,1TBDMS,isomer #2	COC1=C(O)C=CC2=C1N(C)C1=C3C=COC3=CC(O[Si](C)(C)C(C)(C)C)=C1C2=O	3463.1	Semi standard non polar	33892256
Furoparadine,2TBDMS,isomer #1	COC1=C(O[Si](C)(C)C(C)(C)C)C=CC2=C1N(C)C1=C3C=COC3=CC(O[Si](C)(C)C(C)(C)C)=C1C2=O	3661.1	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 - Furoparadine GC-MS (Non-derivatized) - 70eV, Positive	splash10-001j-0291000000-d5e8d8469b9fe20d1cba	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Furoparadine GC-MS (2 TMS) - 70eV, Positive	splash10-007o-2037900000-176e837e198fe5c57ad7	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Furoparadine 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 - Furoparadine 10V, Positive-QTOF	splash10-03di-0029000000-7a0500e607e4c0999510	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Furoparadine 20V, Positive-QTOF	splash10-03e9-0097000000-34dbb74117b6b96f1127	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Furoparadine 40V, Positive-QTOF	splash10-0fyc-0090000000-e5eaf832f2d8484c0887	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Furoparadine 10V, Negative-QTOF	splash10-03di-0009000000-6851417b876e1cc33305	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Furoparadine 20V, Negative-QTOF	splash10-03di-0049000000-fedf7172a8b9f809602c	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Furoparadine 40V, Negative-QTOF	splash10-00kr-0190000000-470e0cd1cccb8e347f3e	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Furoparadine 10V, Negative-QTOF	splash10-03di-0009000000-376db96becea5d318ee5	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Furoparadine 20V, Negative-QTOF	splash10-03di-0039000000-cd669f2db3273e58e1fb	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Furoparadine 40V, Negative-QTOF	splash10-01pc-0291000000-b1231bd13fc2542c2232	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Furoparadine 10V, Positive-QTOF	splash10-03di-0009000000-32b5d43e3f9f7708f611	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Furoparadine 20V, Positive-QTOF	splash10-03di-0009000000-32b5d43e3f9f7708f611	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Furoparadine 40V, Positive-QTOF	splash10-01ql-0090000000-66012ca13d5157fa032b	2021-09-24	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

FDB020965

KNApSAcK ID

C00024254

Chemspider ID

30777535

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

101680139

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1889421

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 Furoparadine (HMDB0041087)

MOL for HMDB0041087 (Furoparadine)

3D MOL for HMDB0041087 (Furoparadine)

3D SDF for HMDB0041087 (Furoparadine)

3D-SDF for HMDB0041087 (Furoparadine)

PDB for HMDB0041087 (Furoparadine)

3D PDB for HMDB0041087 (Furoparadine)

SMILES for HMDB0041087 (Furoparadine)

INCHI for HMDB0041087 (Furoparadine)

Structure for HMDB0041087 (Furoparadine)

3D Structure for HMDB0041087 (Furoparadine)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra