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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:57:39 UTC

Update Date

2022-03-07 02:53:38 UTC

HMDB ID

HMDB0033247

Secondary Accession Numbers

HMDB33247

Metabolite Identification

Common Name

Aristolodione

Description

Grevilline D belongs to the class of organic compounds known as hydroquinones. Hydroquinones are compounds containing a hydroquinone moiety, which consists of a benzene ring with a hydroxyl groups at positions 1 and 4. Grevilline D is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Grevilline D has been detected, but not quantified in, mushrooms. This could make grevilline D a potential biomarker for the consumption of these foods.

Structure

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

HMDB0033247
     RDKit          3D
Aristolodione
 36 39  0  0  0  0  0  0  0  0999 V2000
    3.9050   -0.6937    0.7935 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0860   -0.5956   -0.4031 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7751   -0.9925   -0.3739 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5392   -2.3704   -0.5069 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5998   -3.2103   -0.6669 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2774   -2.8892   -0.4802 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8299   -2.0887   -0.3215 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6107   -0.7218   -0.1919 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7204    0.0825   -0.0345 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6273    1.4498    0.0973 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3514    1.9712    0.0588 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2821    3.3524    0.1494 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9659    3.9186    0.0727 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1033    3.1729   -0.0872 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0314    1.7669   -0.1784 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7960    1.1901   -0.0986 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6916   -0.1935   -0.2231 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0560   -0.4620   -0.0028 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1701    0.4374    0.1656 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2996   -1.8504   -0.1323 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4502   -2.3522   -0.1082 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1479   -2.7096   -0.2992 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2375   -3.9528   -0.4239 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3783   -0.1575    1.6037 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1564   -1.7205    1.0321 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8308   -0.1419    0.5433 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4741   -4.2028   -0.7656 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0981   -3.9703   -0.5852 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5036    2.0735    0.2231 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1668    3.9601    0.2749 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0583    4.9856    0.1402 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0963    3.6104   -0.1508 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9476    1.2726   -0.3521 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1600    1.1707   -0.6764 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1234   -0.1226    0.1902 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0736    0.9836    1.1390 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  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
  9 18  1  0
 18 19  1  0
 18 20  1  0
 20 21  2  0
 20 22  1  0
 22 23  2  0
 17  3  1  0
 22  7  1  0
 17  8  1  0
 16 11  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  5 27  1  0
  6 28  1  0
 10 29  1  0
 12 30  1  0
 13 31  1  0
 14 32  1  0
 15 33  1  0
 19 34  1  0
 19 35  1  0
 19 36  1  0
M  END


  Mrv0541 05061307002D          

 23 26  0  0  0  0            999 V2000
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  2  0  0  0  0
  5  3  1  0  0  0  0
  6  4  1  0  0  0  0
  9  5  2  0  0  0  0
  9  7  1  0  0  0  0
 10  6  2  0  0  0  0
 10  9  1  0  0  0  0
 11  8  2  0  0  0  0
 12  7  2  0  0  0  0
 13  8  1  0  0  0  0
 14 11  1  0  0  0  0
 14 12  1  0  0  0  0
 15 10  1  0  0  0  0
 15 14  2  0  0  0  0
 16 11  1  0  0  0  0
 17 13  2  0  0  0  0
 17 15  1  0  0  0  0
 18 16  1  0  0  0  0
 19  1  1  0  0  0  0
 19 12  1  0  0  0  0
 19 18  1  0  0  0  0
 20 13  1  0  0  0  0
 21 16  2  0  0  0  0
 22 18  2  0  0  0  0
 23  2  1  0  0  0  0
 23 17  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0033247

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=C(O)C=C2C(=O)C(=O)N(C)C3=CC4=CC=CC=C4C1=C23

> <INCHI_IDENTIFIER>
InChI=1S/C18H13NO4/c1-19-12-7-9-5-3-4-6-10(9)15-14(12)11(16(21)18(19)22)8-13(20)17(15)23-2/h3-8,20H,1-2H3

> <INCHI_KEY>
JGDZUWXHWYXMSD-UHFFFAOYSA-N

> <FORMULA>
C18H13NO4

> <MOLECULAR_WEIGHT>
307.3001

> <EXACT_MASS>
307.084457909

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
31.340239426751765

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
15-hydroxy-16-methoxy-10-methyl-10-azatetracyclo[7.7.1.0²,⁷.0¹³,¹⁷]heptadeca-1(17),2,4,6,8,13,15-heptaene-11,12-dione

> <ALOGPS_LOGP>
2.89

> <JCHEM_LOGP>
2.3333265559999994

> <ALOGPS_LOGS>
-3.96

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.925657359902802

> <JCHEM_PKA_STRONGEST_BASIC>
-4.560395109624618

> <JCHEM_POLAR_SURFACE_AREA>
66.84

> <JCHEM_REFRACTIVITY>
84.93539999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.38e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
15-hydroxy-16-methoxy-10-methyl-10-azatetracyclo[7.7.1.0²,⁷.0¹³,¹⁷]heptadeca-1(17),2,4,6,8,13,15-heptaene-11,12-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0033247
     RDKit          3D
Aristolodione
 36 39  0  0  0  0  0  0  0  0999 V2000
    3.9050   -0.6937    0.7935 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0860   -0.5956   -0.4031 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7751   -0.9925   -0.3739 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5392   -2.3704   -0.5069 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5998   -3.2103   -0.6669 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2774   -2.8892   -0.4802 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8299   -2.0887   -0.3215 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6107   -0.7218   -0.1919 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7204    0.0825   -0.0345 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6273    1.4498    0.0973 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3514    1.9712    0.0588 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2821    3.3524    0.1494 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9659    3.9186    0.0727 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1033    3.1729   -0.0872 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0314    1.7669   -0.1784 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7960    1.1901   -0.0986 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6916   -0.1935   -0.2231 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0560   -0.4620   -0.0028 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1701    0.4374    0.1656 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2996   -1.8504   -0.1323 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4502   -2.3522   -0.1082 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1479   -2.7096   -0.2992 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2375   -3.9528   -0.4239 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3783   -0.1575    1.6037 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1564   -1.7205    1.0321 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8308   -0.1419    0.5433 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4741   -4.2028   -0.7656 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0981   -3.9703   -0.5852 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5036    2.0735    0.2231 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1668    3.9601    0.2749 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0583    4.9856    0.1402 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0963    3.6104   -0.1508 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9476    1.2726   -0.3521 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1600    1.1707   -0.6764 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1234   -0.1226    0.1902 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0736    0.9836    1.1390 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  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
  9 18  1  0
 18 19  1  0
 18 20  1  0
 20 21  2  0
 20 22  1  0
 22 23  2  0
 17  3  1  0
 22  7  1  0
 17  8  1  0
 16 11  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  5 27  1  0
  6 28  1  0
 10 29  1  0
 12 30  1  0
 13 31  1  0
 14 32  1  0
 15 33  1  0
 19 34  1  0
 19 35  1  0
 19 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       1.334   3.850   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.002   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   19  N   UNK     0       1.334   2.310   0.000  0.00  0.00           N+0
HETATM   20  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      -1.334  -0.770   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      -1.334   2.310   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       5.335  -3.080   0.000  0.00  0.00           O+0
CONECT    1   19                                                            
CONECT    2   23                                                            
CONECT    3    4    5                                                       
CONECT    4    3    6                                                       
CONECT    5    3    9                                                       
CONECT    6    4   10                                                       
CONECT    7    9   12                                                       
CONECT    8   11   13                                                       
CONECT    9    5    7   10                                                  
CONECT   10    6    9   15                                                  
CONECT   11    8   14   16                                                  
CONECT   12    7   14   19                                                  
CONECT   13    8   17   20                                                  
CONECT   14   11   12   15                                                  
CONECT   15   10   14   17                                                  
CONECT   16   11   18   21                                                  
CONECT   17   13   15   23                                                  
CONECT   18   16   19   22                                                  
CONECT   19    1   12   18                                                  
CONECT   20   13                                                            
CONECT   21   16                                                            
CONECT   22   18                                                            
CONECT   23    2   17                                                       
MASTER        0    0    0    0    0    0    0    0   23    0   52    0
END

COMPND    HMDB0033247
HETATM    1  C1  UNL     1       3.905  -0.694   0.793  1.00  0.00           C  
HETATM    2  O1  UNL     1       3.086  -0.596  -0.403  1.00  0.00           O  
HETATM    3  C2  UNL     1       1.775  -0.992  -0.374  1.00  0.00           C  
HETATM    4  C3  UNL     1       1.539  -2.370  -0.507  1.00  0.00           C  
HETATM    5  O2  UNL     1       2.600  -3.210  -0.667  1.00  0.00           O  
HETATM    6  C4  UNL     1       0.277  -2.889  -0.480  1.00  0.00           C  
HETATM    7  C5  UNL     1      -0.830  -2.089  -0.322  1.00  0.00           C  
HETATM    8  C6  UNL     1      -0.611  -0.722  -0.192  1.00  0.00           C  
HETATM    9  C7  UNL     1      -1.720   0.082  -0.034  1.00  0.00           C  
HETATM   10  C8  UNL     1      -1.627   1.450   0.097  1.00  0.00           C  
HETATM   11  C9  UNL     1      -0.351   1.971   0.059  1.00  0.00           C  
HETATM   12  C10 UNL     1      -0.282   3.352   0.149  1.00  0.00           C  
HETATM   13  C11 UNL     1       0.966   3.919   0.073  1.00  0.00           C  
HETATM   14  C12 UNL     1       2.103   3.173  -0.087  1.00  0.00           C  
HETATM   15  C13 UNL     1       2.031   1.767  -0.178  1.00  0.00           C  
HETATM   16  C14 UNL     1       0.796   1.190  -0.099  1.00  0.00           C  
HETATM   17  C15 UNL     1       0.692  -0.194  -0.223  1.00  0.00           C  
HETATM   18  N1  UNL     1      -3.056  -0.462  -0.003  1.00  0.00           N  
HETATM   19  C16 UNL     1      -4.170   0.437   0.166  1.00  0.00           C  
HETATM   20  C17 UNL     1      -3.300  -1.850  -0.132  1.00  0.00           C  
HETATM   21  O3  UNL     1      -4.450  -2.352  -0.108  1.00  0.00           O  
HETATM   22  C18 UNL     1      -2.148  -2.710  -0.299  1.00  0.00           C  
HETATM   23  O4  UNL     1      -2.238  -3.953  -0.424  1.00  0.00           O  
HETATM   24  H1  UNL     1       3.378  -0.157   1.604  1.00  0.00           H  
HETATM   25  H2  UNL     1       4.156  -1.720   1.032  1.00  0.00           H  
HETATM   26  H3  UNL     1       4.831  -0.142   0.543  1.00  0.00           H  
HETATM   27  H4  UNL     1       2.474  -4.203  -0.766  1.00  0.00           H  
HETATM   28  H5  UNL     1       0.098  -3.970  -0.585  1.00  0.00           H  
HETATM   29  H6  UNL     1      -2.504   2.074   0.223  1.00  0.00           H  
HETATM   30  H7  UNL     1      -1.167   3.960   0.275  1.00  0.00           H  
HETATM   31  H8  UNL     1       1.058   4.986   0.140  1.00  0.00           H  
HETATM   32  H9  UNL     1       3.096   3.610  -0.151  1.00  0.00           H  
HETATM   33  H10 UNL     1       2.948   1.273  -0.352  1.00  0.00           H  
HETATM   34  H11 UNL     1      -4.160   1.171  -0.676  1.00  0.00           H  
HETATM   35  H12 UNL     1      -5.123  -0.123   0.190  1.00  0.00           H  
HETATM   36  H13 UNL     1      -4.074   0.984   1.139  1.00  0.00           H  
CONECT    1    2   24   25   26
CONECT    2    3
CONECT    3    4    4   17
CONECT    4    5    6
CONECT    5   27
CONECT    6    7    7   28
CONECT    7    8   22
CONECT    8    9    9   17
CONECT    9   10   18
CONECT   10   11   11   29
CONECT   11   12   16
CONECT   12   13   13   30
CONECT   13   14   31
CONECT   14   15   15   32
CONECT   15   16   33
CONECT   16   17   17
CONECT   18   19   20
CONECT   19   34   35   36
CONECT   20   21   21   22
CONECT   22   23   23
END

HMDB0033247
     RDKit          3D
Aristolodione
 36 39  0  0  0  0  0  0  0  0999 V2000
    3.9050   -0.6937    0.7935 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0860   -0.5956   -0.4031 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7751   -0.9925   -0.3739 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5392   -2.3704   -0.5069 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5998   -3.2103   -0.6669 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2774   -2.8892   -0.4802 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8299   -2.0887   -0.3215 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6107   -0.7218   -0.1919 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7204    0.0825   -0.0345 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6273    1.4498    0.0973 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3514    1.9712    0.0588 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2821    3.3524    0.1494 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9659    3.9186    0.0727 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1033    3.1729   -0.0872 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0314    1.7669   -0.1784 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7960    1.1901   -0.0986 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6916   -0.1935   -0.2231 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0560   -0.4620   -0.0028 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1701    0.4374    0.1656 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2996   -1.8504   -0.1323 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4502   -2.3522   -0.1082 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1479   -2.7096   -0.2992 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2375   -3.9528   -0.4239 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3783   -0.1575    1.6037 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1564   -1.7205    1.0321 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8308   -0.1419    0.5433 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4741   -4.2028   -0.7656 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0981   -3.9703   -0.5852 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5036    2.0735    0.2231 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1668    3.9601    0.2749 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0583    4.9856    0.1402 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0963    3.6104   -0.1508 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9476    1.2726   -0.3521 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1600    1.1707   -0.6764 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1234   -0.1226    0.1902 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0736    0.9836    1.1390 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  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
  9 18  1  0
 18 19  1  0
 18 20  1  0
 20 21  2  0
 20 22  1  0
 22 23  2  0
 17  3  1  0
 22  7  1  0
 17  8  1  0
 16 11  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  5 27  1  0
  6 28  1  0
 10 29  1  0
 12 30  1  0
 13 31  1  0
 14 32  1  0
 15 33  1  0
 19 34  1  0
 19 35  1  0
 19 36  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Piperadione	HMDB

Chemical Formula

C₁₈H₁₃NO₄

Average Molecular Weight

307.3001

Monoisotopic Molecular Weight

307.084457909

IUPAC Name

15-hydroxy-16-methoxy-10-methyl-10-azatetracyclo[7.7.1.0²,⁷.0¹³,¹⁷]heptadeca-1(17),2,4,6,8,13,15-heptaene-11,12-dione

Traditional Name

15-hydroxy-16-methoxy-10-methyl-10-azatetracyclo[7.7.1.0²,⁷.0¹³,¹⁷]heptadeca-1(17),2,4,6,8,13,15-heptaene-11,12-dione

CAS Registry Number

109771-09-7

SMILES

COC1=C(O)C=C2C(=O)C(=O)N(C)C3=CC4=CC=CC=C4C1=C23

InChI Identifier

InChI=1S/C18H13NO4/c1-19-12-7-9-5-3-4-6-10(9)15-14(12)11(16(21)18(19)22)8-13(20)17(15)23-2/h3-8,20H,1-2H3

InChI Key

JGDZUWXHWYXMSD-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as hydroquinones. Hydroquinones are compounds containing a hydroquinone moiety, which consists of a benzene ring with a hydroxyl groups at positions 1 and 4.

Kingdom

Super Class

Class

Sub Class

Direct Parent

Alternative Parents

Substituents

Catechol
Hydroquinone
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Dihydropyranone
Monocyclic benzene moiety
Pyran
Enol ester
Vinylogous acid
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Carboxylic acid ester
Cyclic ketone
Ketone
Lactone
Carboxylic acid derivative
Oxacycle
Organoheterocyclic compound
Enol
Monocarboxylic acid or derivatives
Hydrocarbon derivative
Organic oxygen compound
Carbonyl group
Organooxygen compound
Organic oxide
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cell membrane (HMDB: HMDB0033247)

Cellular substructure

Membrane (HMDB: HMDB0033247)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0033247)

Source

Exogenous

Food

Food (HMDB: HMDB0033247)

Herb and spice

Herbs and Spices (FooDB: FOOD00866)

Endogenous

Plant

Plant (HMDB: HMDB0033247)

Not Available

Nutrient (HMDB: HMDB0033247)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	273 - 276 °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	0.034 g/L	ALOGPS
logP	2.89	ALOGPS
logP	2.33	ChemAxon
logS	-4	ALOGPS
pKa (Strongest Acidic)	8.93	ChemAxon
pKa (Strongest Basic)	-4.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	66.84 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	84.94 m³·mol⁻¹	ChemAxon
Polarizability	31.34 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]+	169.248	31661259
DarkChem	[M-H]-	173.473	31661259
DeepCCS	[M-2H]-	208.253	30932474
DeepCCS	[M+Na]+	183.48	30932474
AllCCS	[M+H]+	169.7	32859911
AllCCS	[M+H-H2O]+	166.2	32859911
AllCCS	[M+NH4]+	173.0	32859911
AllCCS	[M+Na]+	174.0	32859911
AllCCS	[M-H]-	175.1	32859911
AllCCS	[M+Na-2H]-	174.2	32859911
AllCCS	[M+HCOO]-	173.4	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Aristolodione	COC1=C(O)C=C2C(=O)C(=O)N(C)C3=CC4=CC=CC=C4C1=C23	4555.1	Standard polar	33892256
Aristolodione	COC1=C(O)C=C2C(=O)C(=O)N(C)C3=CC4=CC=CC=C4C1=C23	2622.4	Standard non polar	33892256
Aristolodione	COC1=C(O)C=C2C(=O)C(=O)N(C)C3=CC4=CC=CC=C4C1=C23	3242.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Aristolodione,1TMS,isomer #1	COC1=C(O[Si](C)(C)C)C=C2C(=O)C(=O)N(C)C3=C2C1=C1C=CC=CC1=C3	3133.5	Semi standard non polar	33892256
Aristolodione,1TBDMS,isomer #1	COC1=C(O[Si](C)(C)C(C)(C)C)C=C2C(=O)C(=O)N(C)C3=C2C1=C1C=CC=CC1=C3	3343.6	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 - Aristolodione GC-MS (Non-derivatized) - 70eV, Positive	splash10-0kdl-0091000000-bde2ed4f899ce7ea22a7	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Aristolodione GC-MS (1 TMS) - 70eV, Positive	splash10-022i-3009000000-f1c3502fed1f4965e46b	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Aristolodione GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Aristolodione 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 - Aristolodione 10V, Positive-QTOF	splash10-0a4i-0009000000-442607d5f842a8a116fa	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Aristolodione 20V, Positive-QTOF	splash10-0a4i-0029000000-06ed9891f8f02b752dab	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Aristolodione 40V, Positive-QTOF	splash10-0fkc-1190000000-83e4be3f25d0c290ba66	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Aristolodione 10V, Negative-QTOF	splash10-0a4i-0009000000-f63b281a799602c0b714	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Aristolodione 20V, Negative-QTOF	splash10-0a4i-2039000000-b11b848101198b859e7e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Aristolodione 40V, Negative-QTOF	splash10-06yo-2090000000-553cb7e298794b6e21ae	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Aristolodione 10V, Negative-QTOF	splash10-0a4i-0009000000-df645bd3ab0689ee2835	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Aristolodione 20V, Negative-QTOF	splash10-0a4i-0029000000-d5907b0671277407b55f	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Aristolodione 40V, Negative-QTOF	splash10-000f-0090000000-e3800ada02025c7a0db5	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Aristolodione 10V, Positive-QTOF	splash10-0a4i-0009000000-49652812c5a1d233c09f	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Aristolodione 20V, Positive-QTOF	splash10-0a4i-0019000000-6822ff18beaf7db4bd9e	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Aristolodione 40V, Positive-QTOF	splash10-0f79-0091000000-04502d9a15a49e8076b5	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

FDB011265

KNApSAcK ID

Not Available

Chemspider ID

20124986

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

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 Aristolodione (HMDB0033247)

MOL for HMDB0033247 (Aristolodione)

3D MOL for HMDB0033247 (Aristolodione)

3D SDF for HMDB0033247 (Aristolodione)

3D-SDF for HMDB0033247 (Aristolodione)

PDB for HMDB0033247 (Aristolodione)

3D PDB for HMDB0033247 (Aristolodione)

SMILES for HMDB0033247 (Aristolodione)

INCHI for HMDB0033247 (Aristolodione)

Structure for HMDB0033247 (Aristolodione)

3D Structure for HMDB0033247 (Aristolodione)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra