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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2013-07-09 16:07:59 UTC

Update Date

2021-09-14 15:47:01 UTC

HMDB ID

HMDB0060931

Secondary Accession Numbers

HMDB60931

Metabolite Identification

Common Name

2-ethyl-1,5-dimethyl-3,3-diphenylpyrrolinium (EDDP)

Description

2-ethyl-1,5-dimethyl-3,3-diphenylpyrrolinium (EDDP) belongs to the class of organic compounds known as diphenylmethanes. Diphenylmethanes are compounds containing a diphenylmethane moiety, which consists of a methane wherein two hydrogen atoms are replaced by two phenyl groups. 2-ethyl-1,5-dimethyl-3,3-diphenylpyrrolinium (EDDP) is possibly neutral. Within humans, 2-ethyl-1,5-dimethyl-3,3-diphenylpyrrolinium (eddp) participates in a number of enzymatic reactions. In particular, 2-ethyl-1,5-dimethyl-3,3-diphenylpyrrolinium (eddp) can be biosynthesized from methadone; which is mediated by the enzymes cytochrome P450 2B6, cytochrome P450 2C19, cytochrome P450 2C8, cytochrome P450 2D6, cytochrome P450 3A4, and cytochrome P450 3A7. In addition, 2-ethyl-1,5-dimethyl-3,3-diphenylpyrrolinium (eddp) can be converted into 2-ethyl-5-methyl-3,3-diphenyl-1-pyrroline and formaldehyde; which is catalyzed by the enzyme cytochrome P450 3A7. In humans, 2-ethyl-1,5-dimethyl-3,3-diphenylpyrrolinium (eddp) is involved in methadone metabolism pathway.

Structure

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

HMDB0060931
     RDKit          3D
2-ethyl-1,5-dimethyl-3,3-diphenylpyrrolinium (EDDP)
 45 47  0  0  0  0  0  0  0  0999 V2000
   -2.4435    0.1655    2.6257 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1567    0.3574    1.9380 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9761   -0.1480    0.5686 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7736   -0.8402   -0.1423 N   0  0  0  0  0  4  0  0  0  0  0  0
   -3.0802   -1.2972    0.2704 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2080   -1.0955   -1.4678 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1828   -1.1341   -2.5603 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3667    0.1563   -1.5812 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3246    0.1443   -0.1978 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8132    1.5052    0.0132 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3445    1.9769    1.2055 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8045    3.2729    1.3789 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7484    4.1582    0.3474 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2366    3.7516   -0.8481 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7856    2.4667   -1.0043 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2963   -0.9205   -0.1902 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8096   -1.4386    1.0115 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7450   -2.4447    1.0229 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2013   -2.9689   -0.1633 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7343   -2.5001   -1.3680 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7837   -1.4769   -1.3548 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7927   -0.8732    2.7663 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2356    0.8997    2.3733 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2411    0.4656    3.7178 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9686    1.4786    1.9929 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4098   -0.0391    2.6786 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7650   -0.5087    0.6109 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6361   -1.6640   -0.6607 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0591   -2.2196    0.8747 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5737   -1.9719   -1.4767 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0886   -0.5319   -2.4542 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6882   -0.8014   -3.5075 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5117   -2.1794   -2.7572 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2469    0.1400   -2.4293 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1345    0.9853   -1.5729 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4213    1.3421    2.0512 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2126    3.5995    2.3292 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1160    5.1657    0.5134 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1985    4.4682   -1.6602 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3954    2.2306   -1.9965 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4593   -1.0267    1.9305 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0932   -2.7923    1.9863 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9355   -3.7593   -0.1656 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0983   -2.9178   -2.2879 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4877   -1.1801   -2.3606 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
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  4  5  1  0
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 20 44  1  0
 21 45  1  0
M  CHG  1   4   1
M  END


  Mrv0541 07091309072D          

 21 23  0  0  0  0            999 V2000
    4.4254    1.8247    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4629    0.6697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2577    0.6697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8123    2.3767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7042    4.4460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0164    4.4460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4492    3.6614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5112    4.6175    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2094    4.6175    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2713    3.6614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0013    3.0483    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0632    4.0044    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6574    4.0044    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7193    3.0483    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6928    2.1218    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9478    1.3372    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8082    3.2198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9123    3.2198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0277    2.1218    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3603    2.6067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7728    1.3372    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
  4  1  1  0  0  0  0
  7  5  2  0  0  0  0
  8  5  1  0  0  0  0
  9  6  2  0  0  0  0
 10  6  1  0  0  0  0
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 12  8  2  0  0  0  0
 13  9  1  0  0  0  0
 14 10  2  0  0  0  0
 16  2  1  0  0  0  0
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 20 18  1  0  0  0  0
 20 19  1  0  0  0  0
 21  3  1  0  0  0  0
 21 16  1  0  0  0  0
 21 19  2  0  0  0  0
M  CHG  1  21   1
M  END
> <DATABASE_ID>
HMDB0060931

> <DATABASE_NAME>
hmdb

> <SMILES>
CCC1=[N+](C)C(C)CC1(C1=CC=CC=C1)C1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C20H24N/c1-4-19-20(15-16(2)21(19)3,17-11-7-5-8-12-17)18-13-9-6-10-14-18/h5-14,16H,4,15H2,1-3H3/q+1

> <INCHI_KEY>
SCIYBRNSSXZMKG-UHFFFAOYSA-N

> <FORMULA>
C20H24N

> <MOLECULAR_WEIGHT>
278.4113

> <EXACT_MASS>
278.190874773

> <JCHEM_ACCEPTOR_COUNT>
0

> <JCHEM_AVERAGE_POLARIZABILITY>
33.13832822657019

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
1

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5-ethyl-1,2-dimethyl-4,4-diphenyl-3,4-dihydro-2H-pyrrol-1-ium

> <ALOGPS_LOGP>
0.40

> <JCHEM_LOGP>
1.5368735068615873

> <ALOGPS_LOGS>
-7.05

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_POLAR_SURFACE_AREA>
3.01

> <JCHEM_REFRACTIVITY>
110.96110000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.80e-05 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-ethyl-1,5-dimethyl-3,3-diphenyl-4,5-dihydropyrrol-1-ium

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0060931
     RDKit          3D
2-ethyl-1,5-dimethyl-3,3-diphenylpyrrolinium (EDDP)
 45 47  0  0  0  0  0  0  0  0999 V2000
   -2.4435    0.1655    2.6257 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1567    0.3574    1.9380 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9761   -0.1480    0.5686 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7736   -0.8402   -0.1423 N   0  0  0  0  0  4  0  0  0  0  0  0
   -3.0802   -1.2972    0.2704 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2080   -1.0955   -1.4678 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1828   -1.1341   -2.5603 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3667    0.1563   -1.5812 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3246    0.1443   -0.1978 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8132    1.5052    0.0132 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3445    1.9769    1.2055 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8045    3.2729    1.3789 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7484    4.1582    0.3474 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2366    3.7516   -0.8481 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7856    2.4667   -1.0043 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2963   -0.9205   -0.1902 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8096   -1.4386    1.0115 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7450   -2.4447    1.0229 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2013   -2.9689   -0.1633 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7343   -2.5001   -1.3680 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7837   -1.4769   -1.3548 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7927   -0.8732    2.7663 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2356    0.8997    2.3733 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2411    0.4656    3.7178 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9686    1.4786    1.9929 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4098   -0.0391    2.6786 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7650   -0.5087    0.6109 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6361   -1.6640   -0.6607 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0591   -2.2196    0.8747 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5737   -1.9719   -1.4767 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0886   -0.5319   -2.4542 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6882   -0.8014   -3.5075 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5117   -2.1794   -2.7572 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2469    0.1400   -2.4293 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1345    0.9853   -1.5729 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4213    1.3421    2.0512 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2126    3.5995    2.3292 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1160    5.1657    0.5134 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1985    4.4682   -1.6602 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3954    2.2306   -1.9965 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4593   -1.0267    1.9305 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0932   -2.7923    1.9863 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9355   -3.7593   -0.1656 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0983   -2.9178   -2.2879 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4877   -1.1801   -2.3606 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  1  0
  6  8  1  0
  8  9  1  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
  9 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
  9  3  1  0
 15 10  1  0
 21 16  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  2 25  1  0
  2 26  1  0
  5 27  1  0
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 15 40  1  0
 17 41  1  0
 18 42  1  0
 19 43  1  0
 20 44  1  0
 21 45  1  0
M  CHG  1   4   1
M  END

HEADER    PROTEIN                                 09-JUL-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   09-JUL-13         0                                  
HETATM    1  C   UNK     0       8.261   3.406   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.731   1.250   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.081   1.250   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.116   4.437   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.315   8.299   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.497   8.299   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.839   6.835   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.821   8.619   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.991   8.619   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.973   6.835   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.869   5.690   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.851   7.475   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.960   7.475   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.943   5.690   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.160   3.961   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.636   2.496   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.375   6.010   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.436   6.010   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.652   3.961   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.406   4.866   0.000  0.00  0.00           C+0
HETATM   21  N   UNK     0       5.176   2.496   0.000  0.00  0.00           N+1
CONECT    1    4                                                            
CONECT    2   16                                                            
CONECT    3   21                                                            
CONECT    4    1   19                                                       
CONECT    5    7    8                                                       
CONECT    6    9   10                                                       
CONECT    7    5   11                                                       
CONECT    8    5   12                                                       
CONECT    9    6   13                                                       
CONECT   10    6   14                                                       
CONECT   11    7   17                                                       
CONECT   12    8   17                                                       
CONECT   13    9   18                                                       
CONECT   14   10   18                                                       
CONECT   15   16   20                                                       
CONECT   16    2   15   21                                                  
CONECT   17   11   12   20                                                  
CONECT   18   13   14   20                                                  
CONECT   19    4   20   21                                                  
CONECT   20   15   17   18   19                                             
CONECT   21    3   16   19                                                  
MASTER        0    0    0    0    0    0    0    0   21    0   46    0
END

COMPND    HMDB0060931
HETATM    1  C1  UNL     1      -2.444   0.166   2.626  1.00  0.00           C  
HETATM    2  C2  UNL     1      -1.157   0.357   1.938  1.00  0.00           C  
HETATM    3  C3  UNL     1      -0.976  -0.148   0.569  1.00  0.00           C  
HETATM    4  N1  UNL     1      -1.774  -0.840  -0.142  1.00  0.00           N1+
HETATM    5  C4  UNL     1      -3.080  -1.297   0.270  1.00  0.00           C  
HETATM    6  C5  UNL     1      -1.208  -1.096  -1.468  1.00  0.00           C  
HETATM    7  C6  UNL     1      -2.183  -1.134  -2.560  1.00  0.00           C  
HETATM    8  C7  UNL     1      -0.367   0.156  -1.581  1.00  0.00           C  
HETATM    9  C8  UNL     1       0.325   0.144  -0.198  1.00  0.00           C  
HETATM   10  C9  UNL     1       0.813   1.505   0.013  1.00  0.00           C  
HETATM   11  C10 UNL     1       1.344   1.977   1.206  1.00  0.00           C  
HETATM   12  C11 UNL     1       1.805   3.273   1.379  1.00  0.00           C  
HETATM   13  C12 UNL     1       1.748   4.158   0.347  1.00  0.00           C  
HETATM   14  C13 UNL     1       1.237   3.752  -0.848  1.00  0.00           C  
HETATM   15  C14 UNL     1       0.786   2.467  -1.004  1.00  0.00           C  
HETATM   16  C15 UNL     1       1.296  -0.920  -0.190  1.00  0.00           C  
HETATM   17  C16 UNL     1       1.810  -1.439   1.012  1.00  0.00           C  
HETATM   18  C17 UNL     1       2.745  -2.445   1.023  1.00  0.00           C  
HETATM   19  C18 UNL     1       3.201  -2.969  -0.163  1.00  0.00           C  
HETATM   20  C19 UNL     1       2.734  -2.500  -1.368  1.00  0.00           C  
HETATM   21  C20 UNL     1       1.784  -1.477  -1.355  1.00  0.00           C  
HETATM   22  H1  UNL     1      -2.793  -0.873   2.766  1.00  0.00           H  
HETATM   23  H2  UNL     1      -3.236   0.900   2.373  1.00  0.00           H  
HETATM   24  H3  UNL     1      -2.241   0.466   3.718  1.00  0.00           H  
HETATM   25  H4  UNL     1      -0.969   1.479   1.993  1.00  0.00           H  
HETATM   26  H5  UNL     1      -0.410  -0.039   2.679  1.00  0.00           H  
HETATM   27  H6  UNL     1      -3.765  -0.509   0.611  1.00  0.00           H  
HETATM   28  H7  UNL     1      -3.636  -1.664  -0.661  1.00  0.00           H  
HETATM   29  H8  UNL     1      -3.059  -2.220   0.875  1.00  0.00           H  
HETATM   30  H9  UNL     1      -0.574  -1.972  -1.477  1.00  0.00           H  
HETATM   31  H10 UNL     1      -3.089  -0.532  -2.454  1.00  0.00           H  
HETATM   32  H11 UNL     1      -1.688  -0.801  -3.507  1.00  0.00           H  
HETATM   33  H12 UNL     1      -2.512  -2.179  -2.757  1.00  0.00           H  
HETATM   34  H13 UNL     1       0.247   0.140  -2.429  1.00  0.00           H  
HETATM   35  H14 UNL     1      -1.134   0.985  -1.573  1.00  0.00           H  
HETATM   36  H15 UNL     1       1.421   1.342   2.051  1.00  0.00           H  
HETATM   37  H16 UNL     1       2.213   3.600   2.329  1.00  0.00           H  
HETATM   38  H17 UNL     1       2.116   5.166   0.513  1.00  0.00           H  
HETATM   39  H18 UNL     1       1.199   4.468  -1.660  1.00  0.00           H  
HETATM   40  H19 UNL     1       0.395   2.231  -1.997  1.00  0.00           H  
HETATM   41  H20 UNL     1       1.459  -1.027   1.931  1.00  0.00           H  
HETATM   42  H21 UNL     1       3.093  -2.792   1.986  1.00  0.00           H  
HETATM   43  H22 UNL     1       3.936  -3.759  -0.166  1.00  0.00           H  
HETATM   44  H23 UNL     1       3.098  -2.918  -2.288  1.00  0.00           H  
HETATM   45  H24 UNL     1       1.488  -1.180  -2.361  1.00  0.00           H  
CONECT    1    2   22   23   24
CONECT    2    3   25   26
CONECT    3    4    4    9
CONECT    4    5    6
CONECT    5   27   28   29
CONECT    6    7    8   30
CONECT    7   31   32   33
CONECT    8    9   34   35
CONECT    9   10   16
CONECT   10   11   11   15
CONECT   11   12   36
CONECT   12   13   13   37
CONECT   13   14   38
CONECT   14   15   15   39
CONECT   15   40
CONECT   16   17   17   21
CONECT   17   18   41
CONECT   18   19   19   42
CONECT   19   20   43
CONECT   20   21   21   44
CONECT   21   45
END

HMDB0060931
     RDKit          3D
2-ethyl-1,5-dimethyl-3,3-diphenylpyrrolinium (EDDP)
 45 47  0  0  0  0  0  0  0  0999 V2000
   -2.4435    0.1655    2.6257 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1567    0.3574    1.9380 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9761   -0.1480    0.5686 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7736   -0.8402   -0.1423 N   0  0  0  0  0  4  0  0  0  0  0  0
   -3.0802   -1.2972    0.2704 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2080   -1.0955   -1.4678 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1828   -1.1341   -2.5603 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3667    0.1563   -1.5812 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3246    0.1443   -0.1978 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8132    1.5052    0.0132 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3445    1.9769    1.2055 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8045    3.2729    1.3789 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7484    4.1582    0.3474 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2366    3.7516   -0.8481 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7856    2.4667   -1.0043 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2963   -0.9205   -0.1902 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8096   -1.4386    1.0115 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7450   -2.4447    1.0229 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2013   -2.9689   -0.1633 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7343   -2.5001   -1.3680 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7837   -1.4769   -1.3548 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7927   -0.8732    2.7663 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2356    0.8997    2.3733 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2411    0.4656    3.7178 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9686    1.4786    1.9929 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4098   -0.0391    2.6786 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7650   -0.5087    0.6109 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6361   -1.6640   -0.6607 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0591   -2.2196    0.8747 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5737   -1.9719   -1.4767 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0886   -0.5319   -2.4542 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6882   -0.8014   -3.5075 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5117   -2.1794   -2.7572 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2469    0.1400   -2.4293 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1345    0.9853   -1.5729 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4213    1.3421    2.0512 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2126    3.5995    2.3292 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1160    5.1657    0.5134 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1985    4.4682   -1.6602 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3954    2.2306   -1.9965 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4593   -1.0267    1.9305 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0932   -2.7923    1.9863 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9355   -3.7593   -0.1656 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0983   -2.9178   -2.2879 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4877   -1.1801   -2.3606 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  1  0
  6  8  1  0
  8  9  1  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
  9 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
  9  3  1  0
 15 10  1  0
 21 16  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  2 25  1  0
  2 26  1  0
  5 27  1  0
  5 28  1  0
  5 29  1  0
  6 30  1  0
  7 31  1  0
  7 32  1  0
  7 33  1  0
  8 34  1  0
  8 35  1  0
 11 36  1  0
 12 37  1  0
 13 38  1  0
 14 39  1  0
 15 40  1  0
 17 41  1  0
 18 42  1  0
 19 43  1  0
 20 44  1  0
 21 45  1  0
M  CHG  1   4   1
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₂₀H₂₄N

Average Molecular Weight

278.4113

Monoisotopic Molecular Weight

278.190874773

IUPAC Name

5-ethyl-1,2-dimethyl-4,4-diphenyl-3,4-dihydro-2H-pyrrol-1-ium

Traditional Name

2-ethyl-1,5-dimethyl-3,3-diphenyl-4,5-dihydropyrrol-1-ium

CAS Registry Number

Not Available

SMILES

CCC1=[N+](C)C(C)CC1(C1=CC=CC=C1)C1=CC=CC=C1

InChI Identifier

InChI=1S/C20H24N/c1-4-19-20(15-16(2)21(19)3,17-11-7-5-8-12-17)18-13-9-6-10-14-18/h5-14,16H,4,15H2,1-3H3/q+1

InChI Key

SCIYBRNSSXZMKG-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as diphenylmethanes. Diphenylmethanes are compounds containing a diphenylmethane moiety, which consists of a methane wherein two hydrogen atoms are replaced by two phenyl groups.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Diphenylmethanes

Direct Parent

Diphenylmethanes

Alternative Parents

Substituents

Diphenylmethane
3-phenylpyrroline
Pyrroline
Pyrrole
Azacycle
Organoheterocyclic compound
Organic nitrogen compound
Organopnictogen compound
Hydrocarbon derivative
Organonitrogen compound
Organic cation
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (HMDB: HMDB0060931)

Organ

Kidney (HMDB: HMDB0060931)
Liver (HMDB: HMDB0060931)

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0060931)

Cellular substructure

Cytoplasm (HMDB: HMDB0060931)

Source

Endogenous

Endogenous (HMDB: HMDB0060931)

Process

Naturally occurring process

Biological process

Biochemical pathway

Drug action pathway

Methadone Action Pathway (PathBank: SMP0000408)

Metabolic pathway

Methadone Metabolism Pathway (PathBank: SMP0000624)

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
Water Solubility	2.8e-05 g/L	ALOGPS
logP	0.4	ALOGPS
logP	1.54	ChemAxon
logS	-7	ALOGPS
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	0	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	3.01 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	110.96 m³·mol⁻¹	ChemAxon
Polarizability	33.14 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	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	169.277	30932474
DeepCCS	[M-H]-	166.919	30932474
DeepCCS	[M-2H]-	200.703	30932474
DeepCCS	[M+Na]+	175.93	30932474
AllCCS	[M+H]+	167.3	32859911
AllCCS	[M+H-H2O]+	163.7	32859911
AllCCS	[M+NH4]+	170.7	32859911
AllCCS	[M+Na]+	171.6	32859911
AllCCS	[M-H]-	177.9	32859911
AllCCS	[M+Na-2H]-	177.9	32859911
AllCCS	[M+HCOO]-	178.0	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 √ó 2.1 mm; 1.7 Œºmparticle diameter). Predicted by Afia on May 17, 2022.	6.97 minutes	32390414
Predicted by Siyang on May 30, 2022	22.1576 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.69 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	3219.4 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	692.8 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	266.8 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	351.9 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	446.9 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	977.2 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	915.3 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	81.3 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1952.5 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	704.1 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	1829.2 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	467.6 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	491.4 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	369.6 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	413.7 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	8.2 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
2-ethyl-1,5-dimethyl-3,3-diphenylpyrrolinium (EDDP)	CCC1=[N+](C)C(C)CC1(C1=CC=CC=C1)C1=CC=CC=C1	2653.7	Standard polar	33892256
2-ethyl-1,5-dimethyl-3,3-diphenylpyrrolinium (EDDP)	CCC1=[N+](C)C(C)CC1(C1=CC=CC=C1)C1=CC=CC=C1	2054.7	Standard non polar	33892256
2-ethyl-1,5-dimethyl-3,3-diphenylpyrrolinium (EDDP)	CCC1=[N+](C)C(C)CC1(C1=CC=CC=C1)C1=CC=CC=C1	2032.2	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 2-ethyl-1,5-dimethyl-3,3-diphenylpyrrolinium (EDDP) GC-MS (Non-derivatized) - 70eV, Positive	splash10-01t9-2390000000-c69200da89f159d74b90	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-ethyl-1,5-dimethyl-3,3-diphenylpyrrolinium (EDDP) 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 - 2-ethyl-1,5-dimethyl-3,3-diphenylpyrrolinium (EDDP) 10V, Positive-QTOF	splash10-004i-0090000000-3818f8e469ce13075d7f	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-ethyl-1,5-dimethyl-3,3-diphenylpyrrolinium (EDDP) 20V, Positive-QTOF	splash10-004i-1190000000-d08f7200697a713a098e	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-ethyl-1,5-dimethyl-3,3-diphenylpyrrolinium (EDDP) 40V, Positive-QTOF	splash10-017l-4910000000-e88c5dd87f47f50aba74	2017-10-06	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm

Biospecimen Locations

Blood
Urine

Tissue Locations

Kidney
Liver

Pathways

Name	SMPDB/PathBank	KEGG
Methadone Action Pathway		Not Available
Methadone Metabolism Pathway		Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Normal	Not Available	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Normal	Not Available	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

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10110164

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

Not Available

Showing metabocard for 2-ethyl-1,5-dimethyl-3,3-diphenylpyrrolinium (EDDP) (HMDB0060931)

MOL for HMDB0060931 (2-ethyl-1,5-dimethyl-3,3-diphenylpyrrolinium (EDDP))

3D MOL for HMDB0060931 (2-ethyl-1,5-dimethyl-3,3-diphenylpyrrolinium (EDDP))

3D SDF for HMDB0060931 (2-ethyl-1,5-dimethyl-3,3-diphenylpyrrolinium (EDDP))

3D-SDF for HMDB0060931 (2-ethyl-1,5-dimethyl-3,3-diphenylpyrrolinium (EDDP))

PDB for HMDB0060931 (2-ethyl-1,5-dimethyl-3,3-diphenylpyrrolinium (EDDP))

3D PDB for HMDB0060931 (2-ethyl-1,5-dimethyl-3,3-diphenylpyrrolinium (EDDP))

SMILES for HMDB0060931 (2-ethyl-1,5-dimethyl-3,3-diphenylpyrrolinium (EDDP))

INCHI for HMDB0060931 (2-ethyl-1,5-dimethyl-3,3-diphenylpyrrolinium (EDDP))

Structure for HMDB0060931 (2-ethyl-1,5-dimethyl-3,3-diphenylpyrrolinium (EDDP))

3D Structure for HMDB0060931 (2-ethyl-1,5-dimethyl-3,3-diphenylpyrrolinium (EDDP))

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra