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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 17:37:44 UTC

Update Date

2021-09-26 23:13:03 UTC

HMDB ID

HMDB0256988

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Pyrodone

Description

Pyrodone, also known as MGK-264, belongs to the class of organic compounds known as isoindolones. These are aromatic polycyclic compounds that an isoindole bearing a ketone. Based on a literature review very few articles have been published on Pyrodone. This compound has been identified in human blood as reported by (PMID: 31557052 ). Pyrodone is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Pyrodone is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.

Structure

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

HMDB0256988
     RDKit          3D
Pyrodone
 45 47  0  0  0  0  0  0  0  0999 V2000
   -4.9600    1.5098    2.3891 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7021    0.3534    1.4465 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2464    0.5192    0.9707 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8784   -0.5865    0.0198 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4709   -0.3969   -0.4573 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0381   -1.4771   -1.4156 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9145   -1.5158   -2.6485 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5192   -0.1590    0.6534 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8446    0.0127    0.2254 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4441    1.2413   -0.1115 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9110    2.3629    0.0469 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7684    0.9854   -0.6663 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9172    1.2981    0.2248 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1589    1.2199   -0.6211 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2458   -0.0481   -1.0162 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1791   -0.8592   -0.3301 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0842   -0.0381    0.9732 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8170   -0.5289   -0.8797 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8123   -1.0012    0.0692 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8385   -2.1450    0.6409 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2908    2.4081    1.8128 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0048    1.7178    2.9327 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7565    1.2978    3.1242 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7199   -0.5951    2.0317 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3949    0.3462    0.5992 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6663    0.4172    1.9381 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1617    1.5212    0.5593 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5872   -0.5651   -0.8419 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9973   -1.5498    0.5833 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5052    0.5412   -1.0945 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1954   -2.4544   -0.8857 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0037   -1.4060   -1.7297 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6579   -2.3401   -2.6091 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5021   -0.5663   -2.6426 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3246   -1.5143   -3.5856 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8574    0.7464    1.2514 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5294   -0.9934    1.3858 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9391    1.4882   -1.6414 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8535    2.1474    0.8576 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7793    2.0823   -0.8039 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9854   -0.4055   -1.7257 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4109   -1.8867   -0.1818 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1965   -0.2958    1.5499 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0348   -0.0786    1.5161 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6645   -0.8096   -1.9141 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  5  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
 19 20  2  0
 19  9  1  0
 18 12  1  0
 17 13  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  2 24  1  0
  2 25  1  0
  3 26  1  0
  3 27  1  0
  4 28  1  0
  4 29  1  0
  5 30  1  0
  6 31  1  0
  6 32  1  0
  7 33  1  0
  7 34  1  0
  7 35  1  0
  8 36  1  0
  8 37  1  0
 12 38  1  0
 13 39  1  0
 14 40  1  0
 15 41  1  0
 16 42  1  0
 17 43  1  0
 17 44  1  0
 18 45  1  0
M  END


  Mrv0541 04251301042D          

 20 22  0  0  0  0            999 V2000
   -1.2777   -2.4668    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6749   -1.9036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7762   -1.0848    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4982   -0.6855    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2049   -1.1111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1897   -1.9360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8965   -2.3615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9269   -0.7118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6336   -1.1374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3556   -0.7381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0623   -1.1637    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1351   -2.0602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5344   -1.3383    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0288   -0.7354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1278    0.0746    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1407   -0.9495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9807   -0.1341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9106   -1.6699    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6411   -2.0402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9362   -1.4148    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  5  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
  2 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
  3 14  1  0  0  0  0
 14 15  2  0  0  0  0
 13 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 12 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 16 20  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0256988

> <DATABASE_NAME>
hmdb

> <SMILES>
CCCCC(CC)CN1C(=O)C2C3CC(C=C3)C2C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C17H25NO2/c1-3-5-6-11(4-2)10-18-16(19)14-12-7-8-13(9-12)15(14)17(18)20/h7-8,11-15H,3-6,9-10H2,1-2H3

> <INCHI_KEY>
WLLGXSLBOPFWQV-UHFFFAOYSA-N

> <FORMULA>
C17H25NO2

> <MOLECULAR_WEIGHT>
275.3859

> <EXACT_MASS>
275.188529049

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
31.901719527907435

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-(2-ethylhexyl)-4-azatricyclo[5.2.1.0²,⁶]dec-8-ene-3,5-dione

> <ALOGPS_LOGP>
3.78

> <JCHEM_LOGP>
3.067988293

> <ALOGPS_LOGS>
-3.49

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
19.426669657119298

> <JCHEM_PKA_STRONGEST_BASIC>
-5.315084724247131

> <JCHEM_POLAR_SURFACE_AREA>
37.38

> <JCHEM_REFRACTIVITY>
79.6857

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.96e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-(2-ethylhexyl)-4-azatricyclo[5.2.1.0²,⁶]dec-8-ene-3,5-dione

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0256988
     RDKit          3D
Pyrodone
 45 47  0  0  0  0  0  0  0  0999 V2000
   -4.9600    1.5098    2.3891 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7021    0.3534    1.4465 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2464    0.5192    0.9707 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8784   -0.5865    0.0198 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4709   -0.3969   -0.4573 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0381   -1.4771   -1.4156 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9145   -1.5158   -2.6485 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5192   -0.1590    0.6534 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8446    0.0127    0.2254 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4441    1.2413   -0.1115 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9110    2.3629    0.0469 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7684    0.9854   -0.6663 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9172    1.2981    0.2248 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1589    1.2199   -0.6211 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2458   -0.0481   -1.0162 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1791   -0.8592   -0.3301 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0842   -0.0381    0.9732 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8170   -0.5289   -0.8797 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8123   -1.0012    0.0692 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8385   -2.1450    0.6409 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2908    2.4081    1.8128 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0048    1.7178    2.9327 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7565    1.2978    3.1242 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7199   -0.5951    2.0317 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3949    0.3462    0.5992 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6663    0.4172    1.9381 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1617    1.5212    0.5593 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5872   -0.5651   -0.8419 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9973   -1.5498    0.5833 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5052    0.5412   -1.0945 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1954   -2.4544   -0.8857 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0037   -1.4060   -1.7297 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6579   -2.3401   -2.6091 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5021   -0.5663   -2.6426 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3246   -1.5143   -3.5856 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8574    0.7464    1.2514 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5294   -0.9934    1.3858 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9391    1.4882   -1.6414 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8535    2.1474    0.8576 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7793    2.0823   -0.8039 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9854   -0.4055   -1.7257 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4109   -1.8867   -0.1818 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1965   -0.2958    1.5499 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0348   -0.0786    1.5161 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6645   -0.8096   -1.9141 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  5  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
 19 20  2  0
 19  9  1  0
 18 12  1  0
 17 13  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  2 24  1  0
  2 25  1  0
  3 26  1  0
  3 27  1  0
  4 28  1  0
  4 29  1  0
  5 30  1  0
  6 31  1  0
  6 32  1  0
  7 33  1  0
  7 34  1  0
  7 35  1  0
  8 36  1  0
  8 37  1  0
 12 38  1  0
 13 39  1  0
 14 40  1  0
 15 41  1  0
 16 42  1  0
 17 43  1  0
 17 44  1  0
 18 45  1  0
M  END

HEADER    PROTEIN                                 25-APR-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   25-APR-13         0                                  
HETATM    1  O   UNK     0      -2.385  -4.605   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      -1.260  -3.553   0.000  0.00  0.00           C+0
HETATM    3  N   UNK     0      -1.449  -2.025   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0      -2.797  -1.280   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -4.116  -2.074   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -4.087  -3.614   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -5.407  -4.408   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -5.464  -1.329   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -6.783  -2.123   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -8.130  -1.378   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -9.450  -2.172   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.252  -3.846   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.998  -2.498   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.054  -1.373   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       0.239   0.139   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       2.129  -1.772   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.831  -0.250   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.700  -3.117   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.063  -3.808   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       3.614  -2.641   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   12                                                  
CONECT    3    2    4   14                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    8                                                  
CONECT    6    5    7                                                       
CONECT    7    6                                                            
CONECT    8    5    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10                                                            
CONECT   12    2   13   18                                                  
CONECT   13   12   14   16                                                  
CONECT   14   13    3   15                                                  
CONECT   15   14                                                            
CONECT   16   13   17   20                                                  
CONECT   17   16   18                                                       
CONECT   18   17   12   19                                                  
CONECT   19   18   20                                                       
CONECT   20   19   16                                                       
MASTER        0    0    0    0    0    0    0    0   20    0   44    0
END

COMPND    HMDB0256988
HETATM    1  C1  UNL     1      -4.960   1.510   2.389  1.00  0.00           C  
HETATM    2  C2  UNL     1      -4.702   0.353   1.447  1.00  0.00           C  
HETATM    3  C3  UNL     1      -3.246   0.519   0.971  1.00  0.00           C  
HETATM    4  C4  UNL     1      -2.878  -0.587   0.020  1.00  0.00           C  
HETATM    5  C5  UNL     1      -1.471  -0.397  -0.457  1.00  0.00           C  
HETATM    6  C6  UNL     1      -1.038  -1.477  -1.416  1.00  0.00           C  
HETATM    7  C7  UNL     1      -1.914  -1.516  -2.648  1.00  0.00           C  
HETATM    8  C8  UNL     1      -0.519  -0.159   0.653  1.00  0.00           C  
HETATM    9  N1  UNL     1       0.845   0.013   0.225  1.00  0.00           N  
HETATM   10  C9  UNL     1       1.444   1.241  -0.112  1.00  0.00           C  
HETATM   11  O1  UNL     1       0.911   2.363   0.047  1.00  0.00           O  
HETATM   12  C10 UNL     1       2.768   0.985  -0.666  1.00  0.00           C  
HETATM   13  C11 UNL     1       3.917   1.298   0.225  1.00  0.00           C  
HETATM   14  C12 UNL     1       5.159   1.220  -0.621  1.00  0.00           C  
HETATM   15  C13 UNL     1       5.246  -0.048  -1.016  1.00  0.00           C  
HETATM   16  C14 UNL     1       4.179  -0.859  -0.330  1.00  0.00           C  
HETATM   17  C15 UNL     1       4.084  -0.038   0.973  1.00  0.00           C  
HETATM   18  C16 UNL     1       2.817  -0.529  -0.880  1.00  0.00           C  
HETATM   19  C17 UNL     1       1.812  -1.001   0.069  1.00  0.00           C  
HETATM   20  O2  UNL     1       1.839  -2.145   0.641  1.00  0.00           O  
HETATM   21  H1  UNL     1      -5.291   2.408   1.813  1.00  0.00           H  
HETATM   22  H2  UNL     1      -4.005   1.718   2.933  1.00  0.00           H  
HETATM   23  H3  UNL     1      -5.757   1.298   3.124  1.00  0.00           H  
HETATM   24  H4  UNL     1      -4.720  -0.595   2.032  1.00  0.00           H  
HETATM   25  H5  UNL     1      -5.395   0.346   0.599  1.00  0.00           H  
HETATM   26  H6  UNL     1      -2.666   0.417   1.938  1.00  0.00           H  
HETATM   27  H7  UNL     1      -3.162   1.521   0.559  1.00  0.00           H  
HETATM   28  H8  UNL     1      -3.587  -0.565  -0.842  1.00  0.00           H  
HETATM   29  H9  UNL     1      -2.997  -1.550   0.583  1.00  0.00           H  
HETATM   30  H10 UNL     1      -1.505   0.541  -1.094  1.00  0.00           H  
HETATM   31  H11 UNL     1      -1.195  -2.454  -0.886  1.00  0.00           H  
HETATM   32  H12 UNL     1      -0.004  -1.406  -1.730  1.00  0.00           H  
HETATM   33  H13 UNL     1      -2.658  -2.340  -2.609  1.00  0.00           H  
HETATM   34  H14 UNL     1      -2.502  -0.566  -2.643  1.00  0.00           H  
HETATM   35  H15 UNL     1      -1.325  -1.514  -3.586  1.00  0.00           H  
HETATM   36  H16 UNL     1      -0.857   0.746   1.251  1.00  0.00           H  
HETATM   37  H17 UNL     1      -0.529  -0.993   1.386  1.00  0.00           H  
HETATM   38  H18 UNL     1       2.939   1.488  -1.641  1.00  0.00           H  
HETATM   39  H19 UNL     1       3.853   2.147   0.858  1.00  0.00           H  
HETATM   40  H20 UNL     1       5.779   2.082  -0.804  1.00  0.00           H  
HETATM   41  H21 UNL     1       5.985  -0.405  -1.726  1.00  0.00           H  
HETATM   42  H22 UNL     1       4.411  -1.887  -0.182  1.00  0.00           H  
HETATM   43  H23 UNL     1       3.196  -0.296   1.550  1.00  0.00           H  
HETATM   44  H24 UNL     1       5.035  -0.079   1.516  1.00  0.00           H  
HETATM   45  H25 UNL     1       2.664  -0.810  -1.914  1.00  0.00           H  
CONECT    1    2   21   22   23
CONECT    2    3   24   25
CONECT    3    4   26   27
CONECT    4    5   28   29
CONECT    5    6    8   30
CONECT    6    7   31   32
CONECT    7   33   34   35
CONECT    8    9   36   37
CONECT    9   10   19
CONECT   10   11   11   12
CONECT   12   13   18   38
CONECT   13   14   17   39
CONECT   14   15   15   40
CONECT   15   16   41
CONECT   16   17   18   42
CONECT   17   43   44
CONECT   18   19   45
CONECT   19   20   20
END

HMDB0256988
     RDKit          3D
Pyrodone
 45 47  0  0  0  0  0  0  0  0999 V2000
   -4.9600    1.5098    2.3891 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7021    0.3534    1.4465 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2464    0.5192    0.9707 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8784   -0.5865    0.0198 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4709   -0.3969   -0.4573 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0381   -1.4771   -1.4156 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9145   -1.5158   -2.6485 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5192   -0.1590    0.6534 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8446    0.0127    0.2254 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4441    1.2413   -0.1115 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9110    2.3629    0.0469 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7684    0.9854   -0.6663 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9172    1.2981    0.2248 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1589    1.2199   -0.6211 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2458   -0.0481   -1.0162 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1791   -0.8592   -0.3301 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0842   -0.0381    0.9732 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8170   -0.5289   -0.8797 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8123   -1.0012    0.0692 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8385   -2.1450    0.6409 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2908    2.4081    1.8128 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0048    1.7178    2.9327 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7565    1.2978    3.1242 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7199   -0.5951    2.0317 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3949    0.3462    0.5992 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6663    0.4172    1.9381 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1617    1.5212    0.5593 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5872   -0.5651   -0.8419 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9973   -1.5498    0.5833 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5052    0.5412   -1.0945 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1954   -2.4544   -0.8857 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0037   -1.4060   -1.7297 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6579   -2.3401   -2.6091 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5021   -0.5663   -2.6426 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3246   -1.5143   -3.5856 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8574    0.7464    1.2514 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5294   -0.9934    1.3858 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9391    1.4882   -1.6414 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8535    2.1474    0.8576 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7793    2.0823   -0.8039 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9854   -0.4055   -1.7257 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4109   -1.8867   -0.1818 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1965   -0.2958    1.5499 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0348   -0.0786    1.5161 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6645   -0.8096   -1.9141 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  5  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
 19 20  2  0
 19  9  1  0
 18 12  1  0
 17 13  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  2 24  1  0
  2 25  1  0
  3 26  1  0
  3 27  1  0
  4 28  1  0
  4 29  1  0
  5 30  1  0
  6 31  1  0
  6 32  1  0
  7 33  1  0
  7 34  1  0
  7 35  1  0
  8 36  1  0
  8 37  1  0
 12 38  1  0
 13 39  1  0
 14 40  1  0
 15 41  1  0
 16 42  1  0
 17 43  1  0
 17 44  1  0
 18 45  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
N-Octylbicycloheptene dicarboximide	Kegg
MGK-264	HMDB
MGK 264	HMDB
N-(2-Ethylhexyl)-5-norbornene-2,3-dicarboxamide	HMDB
Ethylhexylbicycloheptene dicarboximide	HMDB

Chemical Formula

C₁₇H₂₅NO₂

Average Molecular Weight

275.3859

Monoisotopic Molecular Weight

275.188529049

IUPAC Name

4-(2-ethylhexyl)-4-azatricyclo[5.2.1.0²,⁶]dec-8-ene-3,5-dione

Traditional Name

4-(2-ethylhexyl)-4-azatricyclo[5.2.1.0²,⁶]dec-8-ene-3,5-dione

CAS Registry Number

Not Available

SMILES

CCCCC(CC)CN1C(=O)C2C3CC(C=C3)C2C1=O

InChI Identifier

InChI=1S/C17H25NO2/c1-3-5-6-11(4-2)10-18-16(19)14-12-7-8-13(9-12)15(14)17(18)20/h7-8,11-15H,3-6,9-10H2,1-2H3

InChI Key

WLLGXSLBOPFWQV-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as isoindolones. These are aromatic polycyclic compounds that an isoindole bearing a ketone.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Isoindoles and derivatives

Sub Class

Isoindolines

Direct Parent

Isoindolones

Alternative Parents

Substituents

Isoindolone
Carboxylic acid imide, n-substituted
Pyrrolidone
2-pyrrolidone
N-alkylpyrrolidine
Carboxylic acid imide
Dicarboximide
Pyrrolidine
Lactam
Carboxylic acid derivative
Azacycle
Organopnictogen compound
Organooxygen compound
Organonitrogen compound
Organic oxygen compound
Organic nitrogen compound
Carbonyl group
Organic oxide
Hydrocarbon derivative
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

isoindoles (CHEBI:81966 )
Insect repellents (C18795 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Source

Exogenous

Exogenous (PMID: 31557052)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

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

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	3.78	ALOGPS
logP	3.07	ChemAxon
logS	-3.5	ALOGPS
pKa (Strongest Acidic)	19.43	ChemAxon
pKa (Strongest Basic)	-5.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	37.38 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	79.69 m³·mol⁻¹	ChemAxon
Polarizability	31.9 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	171.193	30932474
DeepCCS	[M-H]-	168.835	30932474
DeepCCS	[M-2H]-	201.721	30932474
DeepCCS	[M+Na]+	177.287	30932474
AllCCS	[M+H]+	166.9	32859911
AllCCS	[M+H-H2O]+	163.6	32859911
AllCCS	[M+NH4]+	169.8	32859911
AllCCS	[M+Na]+	170.7	32859911
AllCCS	[M-H]-	172.6	32859911
AllCCS	[M+Na-2H]-	172.6	32859911
AllCCS	[M+HCOO]-	172.8	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.	5.7 minutes	32390414
Predicted by Siyang on May 30, 2022	18.2347 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.05 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2697.5 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	519.9 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	219.7 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	262.3 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	429.0 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	796.9 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	811.0 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	79.1 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1569.8 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	527.8 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	1708.3 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	488.1 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	462.6 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	398.7 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	418.5 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	8.4 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Pyrodone	CCCCC(CC)CN1C(=O)C2C3CC(C=C3)C2C1=O	3006.2	Standard polar	33892256
Pyrodone	CCCCC(CC)CN1C(=O)C2C3CC(C=C3)C2C1=O	2111.6	Standard non polar	33892256
Pyrodone	CCCCC(CC)CN1C(=O)C2C3CC(C=C3)C2C1=O	1989.1	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 - Pyrodone GC-MS (Non-derivatized) - 70eV, Positive	splash10-0694-9440000000-40454705bcde83d5fda4	2021-09-24	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Pyrodone GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-03xr-9510000000-d0247447731c32abc9a3	2014-10-20	Not Available	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pyrodone 10V, Positive-QTOF	splash10-004i-1490000000-95e5dd3401ddf362ec17	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pyrodone 20V, Positive-QTOF	splash10-01tc-6490000000-6c6aae6faad89269ac6b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pyrodone 40V, Positive-QTOF	splash10-0006-9100000000-21da35f03c4473badc52	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pyrodone 10V, Negative-QTOF	splash10-0229-0690000000-9b7810dfc603ba0831a7	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pyrodone 20V, Negative-QTOF	splash10-03di-1930000000-3c0254e457a0bf1672a7	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pyrodone 40V, Negative-QTOF	splash10-03dv-9700000000-8aa1972a3ea8b0afb560	2016-08-04	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	31557052	details

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

Not Available

KNApSAcK ID

Not Available

Chemspider ID

7934

KEGG Compound ID

C18795

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Machine Gun Kelly (musician)

METLIN ID

Not Available

PubChem Compound

8227

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1733511

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]

Showing metabocard for Pyrodone (HMDB0256988)

MOL for HMDB0256988 (Pyrodone)

3D MOL for HMDB0256988 (Pyrodone)

3D SDF for HMDB0256988 (Pyrodone)

3D-SDF for HMDB0256988 (Pyrodone)

PDB for HMDB0256988 (Pyrodone)

3D PDB for HMDB0256988 (Pyrodone)

SMILES for HMDB0256988 (Pyrodone)

INCHI for HMDB0256988 (Pyrodone)

Structure for HMDB0256988 (Pyrodone)

3D Structure for HMDB0256988 (Pyrodone)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra