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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-13 11:40:03 UTC

Update Date

2021-09-14 15:47:01 UTC

HMDB ID

HMDB0041803

Secondary Accession Numbers

HMDB41803

Metabolite Identification

Common Name

2-Ethylidene-1,5-dimethyl-3,3-diphenylpyrrolidine

Description

2-Ethylidene-1,5-dimethyl-3,3-diphenylpyrrolidine, also known as EDDP, is a major inactive metabolite of the opioid methadone. Methadone is an opioid drug that is often used to treat addiction to other opioids, such as heroin, oxycodone or fentanyl. Methadone is metabolised in the liver and small intestine where it is converted to EDDP through N-demethylation and cyclization by CYP3A4 (PMID: 15501692 , 27320437 ). EDDP and methadone are eliminated through the kidneys. As such it is common to monitor the urine of patients in a clinical and forensic settings. EDDP is formed through N-desmethylmethadone reacting with itself and cyclizing through condensation of the secondary amine with the carbonyl group (PMID: 27320437 ). EDDP belongs to the family of compounds known as Diphenylmethanes. These are compounds containing a diphenylmethane moiety, which consists of a methane wherein two hydrogen atoms are replaced by two phenyl groups. EDDP is only found in individuals who have taken or been given methadone.

Structure

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

HMDB0041803
     RDKit          3D
2-Ethylidene-1,5-dimethyl-3,3-diphenylpyrrolidine
 44 46  0  0  0  0  0  0  0  0999 V2000
   -2.2948    0.0966   -2.6591 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0521    0.1766   -1.8805 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9818    0.0158   -0.5708 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0318   -0.2568    0.3376 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2777   -0.9034    0.0224 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6629    0.2216    1.6658 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2289   -0.6837    2.7495 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1704    0.1143    1.6794 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2616    0.1089    0.2164 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9247    1.3748   -0.0899 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8715    1.4762   -1.0947 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4582    2.6880   -1.3577 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1535    3.8378   -0.6640 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2134    3.7305    0.3315 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6116    2.5058    0.6065 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1443   -1.0661    0.0716 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2753   -1.1711    0.8301 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0883   -2.2747    0.6851 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7326   -3.2440   -0.2263 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5981   -3.1612   -1.0020 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7953   -2.0300   -0.8311 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9363    0.9594   -2.3234 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8088   -0.8808   -2.5705 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0690    0.3389   -3.7187 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1286    0.3859   -2.4532 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0930   -1.8986   -0.4328 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9762   -0.2741   -0.5718 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8474   -1.1186    0.9775 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0352    1.2320    1.8901 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0140   -1.7407    2.4674 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6423   -0.4762    3.6635 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2936   -0.4754    2.8846 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3301    0.8651    2.2815 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1023   -0.8738    2.1755 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1159    0.5662   -1.6450 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1940    2.7406   -2.1467 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6436    4.7932   -0.9013 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9635    4.6235    0.8843 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1270    2.5636    1.4190 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5743   -0.4121    1.5591 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0015   -2.3834    1.2812 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3606   -4.1214   -0.3548 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3374   -3.9446   -1.7189 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0797   -2.0246   -1.4664 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  3
  3  4  1  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
  5 26  1  0
  5 27  1  0
  5 28  1  0
  6 29  1  0
  7 30  1  0
  7 31  1  0
  7 32  1  0
  8 33  1  0
  8 34  1  0
 11 35  1  0
 12 36  1  0
 13 37  1  0
 14 38  1  0
 15 39  1  0
 17 40  1  0
 18 41  1  0
 19 42  1  0
 20 43  1  0
 21 44  1  0
M  END


  Mrv0541 09131211372D          

 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  0  0  0  0  0  0  0  0  0  0  0
  4  1  1  4  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
 11  7  1  0  0  0  0
 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
 16 15  1  0  0  0  0
 17 11  2  0  0  0  0
 17 12  1  0  0  0  0
 18 13  2  0  0  0  0
 18 14  1  0  0  0  0
 19  4  2  0  0  0  0
 20 15  1  0  0  0  0
 20 17  1  0  0  0  0
 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  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0041803

> <DATABASE_NAME>
hmdb

> <SMILES>
CC=C1N(C)C(C)CC1(C1=CC=CC=C1)C1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C20H23N/c1-4-19-20(15-16(2)21(19)3,17-11-7-5-8-12-17)18-13-9-6-10-14-18/h4-14,16H,15H2,1-3H3

> <INCHI_KEY>
AJRJPORIQGYFMT-UHFFFAOYSA-N

> <FORMULA>
C20H23N

> <MOLECULAR_WEIGHT>
277.4033

> <EXACT_MASS>
277.183049741

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
32.88408229640161

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-ethylidene-1,5-dimethyl-3,3-diphenylpyrrolidine

> <ALOGPS_LOGP>
5.26

> <JCHEM_LOGP>
4.629964395333333

> <ALOGPS_LOGS>
-4.36

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
9.640531803821883

> <JCHEM_POLAR_SURFACE_AREA>
3.24

> <JCHEM_REFRACTIVITY>
101.9382

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.20e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-ethylidene-1,5-dimethyl-3,3-diphenylpyrrolidine

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0041803
     RDKit          3D
2-Ethylidene-1,5-dimethyl-3,3-diphenylpyrrolidine
 44 46  0  0  0  0  0  0  0  0999 V2000
   -2.2948    0.0966   -2.6591 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0521    0.1766   -1.8805 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9818    0.0158   -0.5708 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0318   -0.2568    0.3376 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2777   -0.9034    0.0224 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6629    0.2216    1.6658 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2289   -0.6837    2.7495 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1704    0.1143    1.6794 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2616    0.1089    0.2164 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9247    1.3748   -0.0899 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8715    1.4762   -1.0947 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4582    2.6880   -1.3577 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1535    3.8378   -0.6640 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2134    3.7305    0.3315 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6116    2.5058    0.6065 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1443   -1.0661    0.0716 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2753   -1.1711    0.8301 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0883   -2.2747    0.6851 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7326   -3.2440   -0.2263 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5981   -3.1612   -1.0020 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7953   -2.0300   -0.8311 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9363    0.9594   -2.3234 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8088   -0.8808   -2.5705 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0690    0.3389   -3.7187 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1286    0.3859   -2.4532 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0930   -1.8986   -0.4328 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9762   -0.2741   -0.5718 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8474   -1.1186    0.9775 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0352    1.2320    1.8901 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0140   -1.7407    2.4674 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6423   -0.4762    3.6635 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2936   -0.4754    2.8846 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3301    0.8651    2.2815 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1023   -0.8738    2.1755 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1159    0.5662   -1.6450 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1940    2.7406   -2.1467 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6436    4.7932   -0.9013 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9635    4.6235    0.8843 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1270    2.5636    1.4190 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5743   -0.4121    1.5591 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0015   -2.3834    1.2812 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3606   -4.1214   -0.3548 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3374   -3.9446   -1.7189 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0797   -2.0246   -1.4664 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  3
  3  4  1  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
  5 26  1  0
  5 27  1  0
  5 28  1  0
  6 29  1  0
  7 30  1  0
  7 31  1  0
  7 32  1  0
  8 33  1  0
  8 34  1  0
 11 35  1  0
 12 36  1  0
 13 37  1  0
 14 38  1  0
 15 39  1  0
 17 40  1  0
 18 41  1  0
 19 42  1  0
 20 43  1  0
 21 44  1  0
M  END

HEADER    PROTEIN                                 13-SEP-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   13-SEP-12         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+0
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    HMDB0041803
HETATM    1  C1  UNL     1      -2.295   0.097  -2.659  1.00  0.00           C  
HETATM    2  C2  UNL     1      -1.052   0.177  -1.880  1.00  0.00           C  
HETATM    3  C3  UNL     1      -0.982   0.016  -0.571  1.00  0.00           C  
HETATM    4  N1  UNL     1      -2.032  -0.257   0.338  1.00  0.00           N  
HETATM    5  C4  UNL     1      -3.278  -0.903   0.022  1.00  0.00           C  
HETATM    6  C5  UNL     1      -1.663   0.222   1.666  1.00  0.00           C  
HETATM    7  C6  UNL     1      -2.229  -0.684   2.749  1.00  0.00           C  
HETATM    8  C7  UNL     1      -0.170   0.114   1.679  1.00  0.00           C  
HETATM    9  C8  UNL     1       0.262   0.109   0.216  1.00  0.00           C  
HETATM   10  C9  UNL     1       0.925   1.375  -0.090  1.00  0.00           C  
HETATM   11  C10 UNL     1       1.871   1.476  -1.095  1.00  0.00           C  
HETATM   12  C11 UNL     1       2.458   2.688  -1.358  1.00  0.00           C  
HETATM   13  C12 UNL     1       2.154   3.838  -0.664  1.00  0.00           C  
HETATM   14  C13 UNL     1       1.213   3.730   0.331  1.00  0.00           C  
HETATM   15  C14 UNL     1       0.612   2.506   0.606  1.00  0.00           C  
HETATM   16  C15 UNL     1       1.144  -1.066   0.072  1.00  0.00           C  
HETATM   17  C16 UNL     1       2.275  -1.171   0.830  1.00  0.00           C  
HETATM   18  C17 UNL     1       3.088  -2.275   0.685  1.00  0.00           C  
HETATM   19  C18 UNL     1       2.733  -3.244  -0.226  1.00  0.00           C  
HETATM   20  C19 UNL     1       1.598  -3.161  -1.002  1.00  0.00           C  
HETATM   21  C20 UNL     1       0.795  -2.030  -0.831  1.00  0.00           C  
HETATM   22  H1  UNL     1      -2.936   0.959  -2.323  1.00  0.00           H  
HETATM   23  H2  UNL     1      -2.809  -0.881  -2.570  1.00  0.00           H  
HETATM   24  H3  UNL     1      -2.069   0.339  -3.719  1.00  0.00           H  
HETATM   25  H4  UNL     1      -0.129   0.386  -2.453  1.00  0.00           H  
HETATM   26  H5  UNL     1      -3.093  -1.899  -0.433  1.00  0.00           H  
HETATM   27  H6  UNL     1      -3.976  -0.274  -0.572  1.00  0.00           H  
HETATM   28  H7  UNL     1      -3.847  -1.119   0.978  1.00  0.00           H  
HETATM   29  H8  UNL     1      -2.035   1.232   1.890  1.00  0.00           H  
HETATM   30  H9  UNL     1      -2.014  -1.741   2.467  1.00  0.00           H  
HETATM   31  H10 UNL     1      -1.642  -0.476   3.664  1.00  0.00           H  
HETATM   32  H11 UNL     1      -3.294  -0.475   2.885  1.00  0.00           H  
HETATM   33  H12 UNL     1       0.330   0.865   2.282  1.00  0.00           H  
HETATM   34  H13 UNL     1       0.102  -0.874   2.175  1.00  0.00           H  
HETATM   35  H14 UNL     1       2.116   0.566  -1.645  1.00  0.00           H  
HETATM   36  H15 UNL     1       3.194   2.741  -2.147  1.00  0.00           H  
HETATM   37  H16 UNL     1       2.644   4.793  -0.901  1.00  0.00           H  
HETATM   38  H17 UNL     1       0.963   4.624   0.884  1.00  0.00           H  
HETATM   39  H18 UNL     1      -0.127   2.564   1.419  1.00  0.00           H  
HETATM   40  H19 UNL     1       2.574  -0.412   1.559  1.00  0.00           H  
HETATM   41  H20 UNL     1       4.001  -2.383   1.281  1.00  0.00           H  
HETATM   42  H21 UNL     1       3.361  -4.121  -0.355  1.00  0.00           H  
HETATM   43  H22 UNL     1       1.337  -3.945  -1.719  1.00  0.00           H  
HETATM   44  H23 UNL     1      -0.080  -2.025  -1.466  1.00  0.00           H  
CONECT    1    2   22   23   24
CONECT    2    3    3   25
CONECT    3    4    9
CONECT    4    5    6
CONECT    5   26   27   28
CONECT    6    7    8   29
CONECT    7   30   31   32
CONECT    8    9   33   34
CONECT    9   10   16
CONECT   10   11   11   15
CONECT   11   12   35
CONECT   12   13   13   36
CONECT   13   14   37
CONECT   14   15   15   38
CONECT   15   39
CONECT   16   17   17   21
CONECT   17   18   40
CONECT   18   19   19   41
CONECT   19   20   42
CONECT   20   21   21   43
CONECT   21   44
END

HMDB0041803
     RDKit          3D
2-Ethylidene-1,5-dimethyl-3,3-diphenylpyrrolidine
 44 46  0  0  0  0  0  0  0  0999 V2000
   -2.2948    0.0966   -2.6591 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0521    0.1766   -1.8805 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9818    0.0158   -0.5708 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0318   -0.2568    0.3376 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2777   -0.9034    0.0224 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6629    0.2216    1.6658 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2289   -0.6837    2.7495 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1704    0.1143    1.6794 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2616    0.1089    0.2164 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9247    1.3748   -0.0899 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8715    1.4762   -1.0947 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4582    2.6880   -1.3577 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1535    3.8378   -0.6640 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2134    3.7305    0.3315 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6116    2.5058    0.6065 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1443   -1.0661    0.0716 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2753   -1.1711    0.8301 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0883   -2.2747    0.6851 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7326   -3.2440   -0.2263 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5981   -3.1612   -1.0020 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7953   -2.0300   -0.8311 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9363    0.9594   -2.3234 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8088   -0.8808   -2.5705 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0690    0.3389   -3.7187 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1286    0.3859   -2.4532 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0930   -1.8986   -0.4328 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9762   -0.2741   -0.5718 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8474   -1.1186    0.9775 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0352    1.2320    1.8901 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0140   -1.7407    2.4674 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6423   -0.4762    3.6635 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2936   -0.4754    2.8846 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3301    0.8651    2.2815 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1023   -0.8738    2.1755 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1159    0.5662   -1.6450 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1940    2.7406   -2.1467 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6436    4.7932   -0.9013 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9635    4.6235    0.8843 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1270    2.5636    1.4190 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5743   -0.4121    1.5591 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0015   -2.3834    1.2812 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3606   -4.1214   -0.3548 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3374   -3.9446   -1.7189 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0797   -2.0246   -1.4664 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  3
  3  4  1  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
  5 26  1  0
  5 27  1  0
  5 28  1  0
  6 29  1  0
  7 30  1  0
  7 31  1  0
  7 32  1  0
  8 33  1  0
  8 34  1  0
 11 35  1  0
 12 36  1  0
 13 37  1  0
 14 38  1  0
 15 39  1  0
 17 40  1  0
 18 41  1  0
 19 42  1  0
 20 43  1  0
 21 44  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
EDDP	HMDB
2-Ethylidene-1,5-dimethyl-3,3-diphenylpyrrolidine, perchlorate, (+-)-isomer	HMDB
2-Ethylidene-1,5-dimethyl-3,3-diphenylpyrrolidine, (e)-isomer	HMDB
2-Ethylidene-1,5-dimethyl-3,3-diphenylpyrrolidine, (Z)-isomer	HMDB
EDDP-3,3	HMDB
2-Ethylidene-1,5-dimethyl-3,3-diphenylpyrrolidine, perchlorate	HMDB
1,5-Dimethyl-3,3-diphenyl-2-ethylidenepyrrolidine	HMDB
2-Et-1,5-dime-3,3-DPP	HMDB
2-Ethylidene-1,5-dimethyl-3,3-diphenylpyrrolidine, (+-)-isomer	HMDB
EDPP	HMDB

Chemical Formula

C₂₀H₂₃N

Average Molecular Weight

277.4033

Monoisotopic Molecular Weight

277.183049741

IUPAC Name

2-ethylidene-1,5-dimethyl-3,3-diphenylpyrrolidine

Traditional Name

2-ethylidene-1,5-dimethyl-3,3-diphenylpyrrolidine

CAS Registry Number

30223-73-5

SMILES

CC=C1N(C)C(C)CC1(C1=CC=CC=C1)C1=CC=CC=C1

InChI Identifier

InChI=1S/C20H23N/c1-4-19-20(15-16(2)21(19)3,17-11-7-5-8-12-17)18-13-9-6-10-14-18/h4-14,16H,15H2,1-3H3

InChI Key

AJRJPORIQGYFMT-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-phenylpyrrolidine
Aralkylamine
N-alkylpyrrolidine
Pyrrole
Pyrrolidine
Tertiary amine
Tertiary aliphatic amine
Azacycle
Enamine
Organoheterocyclic compound
Amine
Hydrocarbon derivative
Organopnictogen compound
Organonitrogen compound
Organic nitrogen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

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	0.012 g/L	ALOGPS
logP	5.26	ALOGPS
logP	4.63	ChemAxon
logS	-4.4	ALOGPS
pKa (Strongest Basic)	9.64	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	3.24 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	101.94 m³·mol⁻¹	ChemAxon
Polarizability	32.88 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
DarkChem	[M+H]+	164.779	31661259
DarkChem	[M-H]-	167.91	31661259
DeepCCS	[M+H]+	168.279	30932474
DeepCCS	[M-H]-	165.921	30932474
DeepCCS	[M-2H]-	198.83	30932474
DeepCCS	[M+Na]+	174.373	30932474
AllCCS	[M+H]+	166.4	32859911
AllCCS	[M+H-H2O]+	162.7	32859911
AllCCS	[M+NH4]+	169.9	32859911
AllCCS	[M+Na]+	170.9	32859911
AllCCS	[M-H]-	176.8	32859911
AllCCS	[M+Na-2H]-	176.5	32859911
AllCCS	[M+HCOO]-	176.2	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
2-Ethylidene-1,5-dimethyl-3,3-diphenylpyrrolidine	CC=C1N(C)C(C)CC1(C1=CC=CC=C1)C1=CC=CC=C1	2958.4	Standard polar	33892256
2-Ethylidene-1,5-dimethyl-3,3-diphenylpyrrolidine	CC=C1N(C)C(C)CC1(C1=CC=CC=C1)C1=CC=CC=C1	2095.4	Standard non polar	33892256
2-Ethylidene-1,5-dimethyl-3,3-diphenylpyrrolidine	CC=C1N(C)C(C)CC1(C1=CC=CC=C1)C1=CC=CC=C1	2052.3	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-Ethylidene-1,5-dimethyl-3,3-diphenylpyrrolidine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0400-2490000000-f4f88e035ceeefacbfe1	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Ethylidene-1,5-dimethyl-3,3-diphenylpyrrolidine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Ethylidene-1,5-dimethyl-3,3-diphenylpyrrolidine 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-Ethylidene-1,5-dimethyl-3,3-diphenylpyrrolidine 10V, Positive-QTOF	splash10-004i-0090000000-3549c0cf470bb5da6d65	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Ethylidene-1,5-dimethyl-3,3-diphenylpyrrolidine 20V, Positive-QTOF	splash10-004r-2090000000-41c296555b689f42d8f9	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Ethylidene-1,5-dimethyl-3,3-diphenylpyrrolidine 40V, Positive-QTOF	splash10-0a6r-4490000000-aa9cff186721298bd676	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Ethylidene-1,5-dimethyl-3,3-diphenylpyrrolidine 10V, Negative-QTOF	splash10-004i-0090000000-a93ce53605da0af2b384	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Ethylidene-1,5-dimethyl-3,3-diphenylpyrrolidine 20V, Negative-QTOF	splash10-004i-0090000000-4e95e4f3b18a99b46953	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Ethylidene-1,5-dimethyl-3,3-diphenylpyrrolidine 40V, Negative-QTOF	splash10-08ir-4090000000-24dc59784ee89b478aba	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Ethylidene-1,5-dimethyl-3,3-diphenylpyrrolidine 10V, Negative-QTOF	splash10-004i-0090000000-c524df0015f139e69d14	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Ethylidene-1,5-dimethyl-3,3-diphenylpyrrolidine 20V, Negative-QTOF	splash10-056r-0190000000-a3239a29ff29fdb30074	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Ethylidene-1,5-dimethyl-3,3-diphenylpyrrolidine 40V, Negative-QTOF	splash10-0002-1690000000-c6cd75ed66d7c7df8825	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Ethylidene-1,5-dimethyl-3,3-diphenylpyrrolidine 10V, Positive-QTOF	splash10-004i-0090000000-42e8ca45e48cd8643b2f	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Ethylidene-1,5-dimethyl-3,3-diphenylpyrrolidine 20V, Positive-QTOF	splash10-004i-0090000000-3205c286438d06c44be1	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Ethylidene-1,5-dimethyl-3,3-diphenylpyrrolidine 40V, Positive-QTOF	splash10-0gb9-3890000000-8e58260d59973324d407	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane (predicted from logP)

Biospecimen Locations

Blood
Urine

Tissue Locations

Kidney
Liver

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

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

23254962

KEGG Compound ID

C16659

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

2-Ethylidene-1,5-dimethyl-3,3-diphenylpyrrolidine

METLIN ID

Not Available

PubChem Compound

5378015

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

Ferrari A, Coccia CP, Bertolini A, Sternieri E: Methadone--metabolism, pharmacokinetics and interactions. Pharmacol Res. 2004 Dec;50(6):551-9. doi: 10.1016/j.phrs.2004.05.002. [PubMed:15501692 ]
Dinis-Oliveira RJ: Metabolomics of methadone: clinical and forensic toxicological implications and variability of dose response. Drug Metab Rev. 2016 Nov;48(4):568-576. doi: 10.1080/03602532.2016.1192642. Epub 2016 Jun 20. [PubMed:27320437 ]

Showing metabocard for 2-Ethylidene-1,5-dimethyl-3,3-diphenylpyrrolidine (HMDB0041803)

MOL for HMDB0041803 (2-Ethylidene-1,5-dimethyl-3,3-diphenylpyrrolidine)

3D MOL for HMDB0041803 (2-Ethylidene-1,5-dimethyl-3,3-diphenylpyrrolidine)

3D SDF for HMDB0041803 (2-Ethylidene-1,5-dimethyl-3,3-diphenylpyrrolidine)

3D-SDF for HMDB0041803 (2-Ethylidene-1,5-dimethyl-3,3-diphenylpyrrolidine)

PDB for HMDB0041803 (2-Ethylidene-1,5-dimethyl-3,3-diphenylpyrrolidine)

3D PDB for HMDB0041803 (2-Ethylidene-1,5-dimethyl-3,3-diphenylpyrrolidine)

SMILES for HMDB0041803 (2-Ethylidene-1,5-dimethyl-3,3-diphenylpyrrolidine)

INCHI for HMDB0041803 (2-Ethylidene-1,5-dimethyl-3,3-diphenylpyrrolidine)

Structure for HMDB0041803 (2-Ethylidene-1,5-dimethyl-3,3-diphenylpyrrolidine)

3D Structure for HMDB0041803 (2-Ethylidene-1,5-dimethyl-3,3-diphenylpyrrolidine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra